KR20190140747A - Compound, photosensitive resin composition comprising the same, photo resist, color filter, and display device - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1, and a photosensitive resin composition, a photosensitive material, a color filter, and a display device comprising the same. The compound according to an embodiment of the present specification can be used as a color material in the photosensitive resin composition, and when used as the color material, there is an advantage that a contrast ratio can be improved.

Description

COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION COMPRISING THE SAME, PHOTO RESIST, COLOR FILTER, AND DISPLAY DEVICE}

The present specification relates to a compound and a photosensitive resin composition including the same. In addition, the present specification relates to a photosensitive material, a color filter, and a display device manufactured using the photosensitive resin composition.

In recent years, the performance of the color filter characterized by high brightness and high contrast ratio has been demanded. In addition, one of the main purposes of the display device development is to differentiate the display device performance through the improvement of color purity and to improve the productivity in the manufacturing process.

Since the pigment type conventionally used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, the light particles are aggregated in the color filter, resulting in poor dissolution and dispersibility, and multiple scattering of light occurs due to the aggregation of large particles. The scattering of the polarized light has been pointed out as a main factor for lowering the contrast ratio. Efforts have been made to improve the luminance and contrast ratio through ultrafine atomization and dispersion stabilization of pigments, but the degree of freedom in selecting colorants to implement color coordinates for high color purity display devices is limited. In addition, the pigment dispersion method using the already developed color material, especially pigment has reached the limit to improve the color purity, brightness and contrast ratio of the color filter using the same.

Accordingly, there is a demand for the development of a new color material that can improve color purity and improve color reproduction, brightness, and contrast ratio.

Korean Laid-Open Patent No. 2001-0009058

The present inventors aim to provide a compound, a photosensitive resin composition comprising the same, a photosensitive material prepared using the same, a color filter, and a display device.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

L is a direct bond; O; Or S,

A is a halogen group; Hydroxyl group; Sulfonic acid groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

Het is a substituted or unsubstituted heteroaryl group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Sulfonic acid groups; Or a sulfonate group,

r1 is an integer of 0 to 4, when r1 is 2 or more, R1 is the same or different,

r2 is an integer of 0 to 2, and when r2 is 2, R2 is the same or different.

An exemplary embodiment of the present specification, the compound represented by Formula 1; Binder resins; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition comprising a solvent.

An exemplary embodiment of the present specification provides a photosensitive material manufactured using the photosensitive resin composition.

An exemplary embodiment of the present specification provides a color filter including the photosensitive material.

An exemplary embodiment of the present specification provides a display device including the color filter.

The compound according to the exemplary embodiment of the present specification may be used as a color material in the photosensitive resin composition, and when used as a color material, there is an advantage that the contrast ratio may be improved.

Hereinafter, this specification is demonstrated in detail.

In this specification, when a member is located “on” another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

According to an exemplary embodiment of the present specification, a compound represented by Formula 1 is provided.

L in Formula 1 is O; Alternatively, in the case of S, the dipole momonet of the entire molecule is increased, and when the particles including the compound represented by Chemical Formula 1 are atomized, the particle size of the molecule can be further reduced, and an excellent contrast ratio can be obtained.

In addition, when Het of the general formula (1) is a heteroaryl group, the bonding angle is increased than that of the alkyl group, and the interaction between molecules (π-π stacking) is reduced, and when the particles are atomized, the particle size of the molecule may be further reduced. It is possible to obtain an excellent contrast ratio.

In addition, when Het of the said Formula (1) is a heterocyclic ring of 5 to 5 rings, molecular weight is smaller than the heterocyclic group of 8 or more rings. The photosensitive resin composition containing the compound when Het of the formula (1) is a 2 to 5 ring heteroaryl group, compared with the photosensitive resin composition containing the compound when Het of the formula (1) is an 8 or more ring heteroaryl group , The mass absorption coefficient of the compound according to the present specification contained in the same mass photosensitive resin composition is increased, and excellent contrast ratio can be obtained.

Examples of substituents of the compound represented by Formula 1 are described below, but are not limited thereto.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Means a site which is bonded to another substituent or binding moiety.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Sulfonic acid groups; Sulfonate groups; Nitrile group; Nitro group; Hydroxyl group; -COOH; Imide group; Amide group; An alkoxy group; Alkyl groups; Cycloalkyl group; Amine groups; Aryl group; Heteroaryl group; Acryloyl group; Acrylate group; It means that it is substituted with one or more substituents selected from the group comprising an anionic group and a heterocyclic group containing one or more of N, O, S or P atoms or have no substituents.

As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the ring refers to an aromatic or aliphatic ring in that adjacent groups can combine to form a “ring”. Specifically, the ring may be an aromatic ring, it may be an aryl group or a heteroaryl group. The following description may be applied to the aryl group and heteroaryl group.

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

In the present specification, the alkoxy group may be linear or branched chain, carbon number is not particularly limited, but may be 1 to 30, specifically 1 to 20, more specifically 1 to 10.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade Although there exist a tilt group etc., it is not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. According to another exemplary embodiment, the aryl group has 6 to 12 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perrylenyl group, triphenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the acryloyl group means a photopolymerizable unsaturated group, and for example, (meth) acryloyl group may be mentioned, but is not limited thereto.

In the present specification, the acrylate group refers to a photopolymerizable unsaturated group, and examples thereof include (meth) acrylate groups, but are not limited thereto.

In this specification, "(meth) acryloyl" represents at least 1 sort (s) chosen from the group which consists of acryloyl and methacryloyl. The description of '(meth) acrylate' also has the same meaning.

In the present specification, the sulfonic acid group is -SO ₃ H.

In one embodiment of the present specification, the sulfonate group may be represented by -SO ₃ M. M may be one of Group 1 metal elements of the periodic table. Specifically M may be Na.

In one embodiment of the present specification, L is a direct bond; O; Or S.

In one embodiment of the present specification, L is a direct bond.

In one embodiment of the present specification, L is O.

In one embodiment of the present specification, L is S.

In one embodiment of the present specification, A is a halogen group; Hydroxyl group; Sulfonic acid groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, A is a halogen group; Sulfonic acid groups; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, A is a halogen group; Sulfonic acid groups; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A is a halogen group; Sulfonic acid groups; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, A is a halogen group; Sulfonic acid groups; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, A is bromine (Br); Sulfonic acid groups; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted butyl group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, A is bromine (Br); Sulfonic acid groups; Ethyl group; Profile group; Isobutyl group; Or a phenyl group unsubstituted or substituted with a methyl group.

In one embodiment of the present specification, Het is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Het is a substituted or unsubstituted heteroaryl group having 2 to 5 rings.

In one embodiment of the present specification, Het is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Het is a substituted or unsubstituted heteroaryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Het is a substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted quinoline group; Or a substituted or unsubstituted isoquinoline group.

In one embodiment of the present specification, the substituted or unsubstituted dibenzofuranyl group may be represented by any one of the following substituents.

In one embodiment of the present specification, the substituted or unsubstituted dibenzopiophenyl group may be represented by the following substituents.

In one embodiment of the present specification, the substituted or unsubstituted carbazole group may be represented by any one of the following substituents.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Sulfonic acid groups; Or sulfonate groups.

In one embodiment of the present specification, R1 is hydrogen.

In one embodiment of the present specification, R2 is hydrogen; Sulfonic acid groups; Or sulfonate groups.

In one embodiment of the present specification, R2 is hydrogen; -SO ₃ H or -SO ₃ Na.

In one embodiment of the present specification, r1 is an integer of 0 to 4, when r1 is 2 or more, R1 is the same or different, r2 is an integer of 0 to 2, and when r2 is 2, R2 is the same or different. Do.

According to yet an embodiment of the present disclosure, Formula 1 may be represented by the following formula (2).

[Formula 2]

In Chemical Formula 2,

L, A, R1, R2, r1 and r2 are the same as defined in Chemical Formula 1,

X is O; S; Or NR ',

R 'is hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,

r3 is an integer of 0 to 4, when r3 is 2 or more, R3 is the same as or different from each other,

r4 is an integer of 0 to 3, and when r4 is 2 or more, R4 is the same as or different from each other.

In one embodiment of the present specification, R 'is hydrogen; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R 'is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R 'is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R 'is hydrogen; Or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, R 'is hydrogen; Or a substituted or unsubstituted phenyl group.

 In one embodiment of the present specification, R 'is hydrogen; Or a phenyl group substituted with a nitro group.

In one embodiment of the present specification, R3 is hydrogen, or an adjacent group may be bonded to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R3 is hydrogen, or an adjacent group may be bonded to form a substituted or unsubstituted aromatic ring.

In one embodiment of the present specification, R3 is hydrogen, or an adjacent group may be bonded to form a substituted or unsubstituted hetero ring including a substituted or unsubstituted benzene ring or O.

In one embodiment of the present specification, R3 is hydrogen, or an adjacent group may be bonded to form a hetero ring including a benzene ring or O.

According to yet an embodiment of the present disclosure, Formula 1 may be represented by the following formula (3).

[Formula 3]

In Chemical Formula 3,

L, A, R1, R2, r1 and r2 are the same as defined in Chemical Formula 1,

Y1 and Y2 are the same as or different from each other, and each independently CR '' or N,

R ″ is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

R5 and R6 are the same as or different from each other, and each independently hydrogen; Or deuterium,

r5 is an integer of 0 to 2, when r5 is 2, R5 is the same as or different from each other,

r6 is an integer of 0 to 3, and when r6 is 2 or more, R6 is the same or different from each other.

In one embodiment of the present specification, Y1 is N.

In one embodiment of the present specification, Y1 is CR ''.

In one embodiment of the present specification, Y2 is N.

In one embodiment of the present specification, Y2 is CR ''.

In one embodiment of the present specification, R ″ is hydrogen.

In one embodiment of the present specification, R5 and R6 are hydrogen.

According to yet an embodiment of the present disclosure, Formula 1 may be represented by any one of the following formula, but is not necessarily limited thereto.

In addition, according to an exemplary embodiment of the present specification, it is possible to provide a color material composition comprising the compound.

The color material composition may further include at least one of dyes and pigments in addition to the compound of Formula 1. For example, the colorant composition may include only the compound of Formula 1, but may include the compound of Formula 1 and one or more dyes, or may include the compound of Formula 1 and one or more pigments, or the compound of Formula 1 And at least one dye and at least one pigment.

According to one embodiment of the present specification, a resin composition including the color material composition may be provided.

According to an exemplary embodiment of the present specification, the resin composition is a compound represented by Formula 1; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.

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

The binder resin may use a copolymer resin of a polyfunctional monomer imparting mechanical strength and a monomer imparting alkali solubility, and may further include a binder generally used in the art.

Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate , p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1 , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate , Methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate It is, but is not limited thereto.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro styrene. It may be selected from the group consisting of, but is not limited to these.

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 imides are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.

Examples of the acid anhydride include maleic anhydride, methyl maleic anhydride, tetrahydro phthalic anhydride, and the like, but are not limited thereto.

The monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group. For example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate selected from the group consisting of Although it is preferable to use 1 or more types, it is not limited to these.

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

The polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.

The photoinitiator is not particularly limited as long as it is an initiator that generates radicals by light to trigger crosslinking. For example, the photoinitiator is selected from the group consisting of acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. It may be one or more kinds.

The acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, and the like.

As the biimidazole-based compound, 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.

The triazine compound is 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3- Hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4 -Bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} acetate, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, benzyl-2- {4- [ 2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6 -Yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionamide, 2,4-bis (trichloro Methyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-di Methylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but is not limited thereto. .

The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGII242), N-1919 (Adeca Co.), and the like.

The solvent is 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 , 1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl ah Cetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but may be It is not limited only.

According to one embodiment of the present specification, based on the total weight of solids in the resin composition, the content of the compound represented by Formula 1 is 5% by weight to 60% by weight, and the content of the binder resin is 1% by weight to 60 wt%, the content of the photoinitiator is 0.1 wt% to 20 wt%, and the content of the multifunctional monomer is 0.1 wt% to 50 wt%.

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 weight percentages based on solids and solids of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the resin composition may further include an antioxidant.

According to an exemplary embodiment of the present specification, the content of the antioxidant is 0.1% to 20% by weight based on the total weight of solids in the resin composition.

According to one embodiment of the present specification, the resin composition may include one or two or more additives selected from the group consisting of a photocrosslinking agent, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, a UV absorber, a dispersant, and a leveling agent. It includes.

According to an exemplary embodiment of the present specification, the content of the additive is 0.1% by weight to 20% by weight based on the total weight of solids in the resin composition.

The photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone 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-phenylacridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzo Coumarin-based compounds such as pyrano [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of can be used.

The curing accelerator is used to increase the curing and mechanical strength, 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), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio Nate) can be used one or more selected from the group consisting of.

As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents, such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, specifically, the silicone-based surfactant is BYK-Chemie's 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-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. (DaiNippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-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, etc. may be used, but is not limited thereto.

The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-butylphenol) or bis [3 , 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine System secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane System secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4 ' Phosphite-based secondary antioxidants such as -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, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.

The dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.

The leveling agent may be polymeric or nonpolymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.

According to one embodiment of the present specification, a photosensitive material manufactured using the resin composition is provided.

In more detail, the resin composition of this specification is apply | coated on a base material by a suitable method, and forms the photosensitive material of a thin film or a pattern form.

Although it does not restrict | limit especially as said coating method, A spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely. In addition, after forming a coating film, some residual solvent can be removed in some cases under reduced pressure.

The resin composition according to the present disclosure may be a pigment dispersion photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display device (TFT LCD) or an organic light emitting diode, It can be used for photosensitive material for forming overcoat layer, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed circuit board, photosensitive material for plasma display panel (PDP), and the like. There is no special place.

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

The color filter may be manufactured using a resin composition containing the compound represented by Chemical Formula 1. The resin composition may be applied onto a substrate to form a coating film, and the color filter may be formed by exposing, developing, and curing the coating film.

As a light source for curing the resin composition according to the present specification, for example, mercury vapor arc (arc), carbon arc, Xe arc, etc., which emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto.

When using the resin composition according to one embodiment of the present specification, it is possible to provide a color filter having a high contrast ratio.

The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the type 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 exemplary embodiment, the color filter may further include an overcoat layer.

A black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution caused by 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 specification may use black pigment or black dye as a colorant. For example, carbon black may be used alone, or carbon black and coloring pigments may be used. At this time, since coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.

Provided is a display device including a color filter according to the present specification.

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 thin film transistor. The liquid crystal display device may be any one of a liquid crystal display (LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

<Production example>

Preparation Example 1 Synthesis of Compound A

(1) Synthesis of Compound A-1

2-dibenzo [b, d] furanol (50 g, 271.7 mmol) was dissolved in AcOH (100 ml), iodine monochloride (48.4 g, 298.9 mmol) was added thereto, and the mixture was stirred at about 100 ° C. for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, and the organic layer was separated from the filtrate. The organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with ethanol to obtain the compound A-1 (58.9 g, 70%). .: MS [M] = 309.9

(2) Synthesis of Compound A-2

Compound A-1 (20 g, 64.5 mmol), 4-chloro-2-fluorophenylboronic acid (13.4 g, 77.4 mmol), Pd (t-Bu3P) 2 (0.066 g, 0.129 mmol) was added to a 2M aqueous K2CO3 solution ( 60 mL) and THF (200 mL) were stirred at reflux for about 4 hours. After the reaction was completed, the mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with Tol / EA to obtain Compound A-2 (13.3 g, 71%). ] = 312.0

(3) Synthesis of Compound A-3

Compound A-2 (20 g, 64.1 mmol) and K ₂ CO ₃ were dissolved in (17.7 g, 128.2 mmol) in MDAc (300 ml) and stirred at about 100 ° C. for 4 hours. After the reaction was cooled to room temperature, H2O (100 ml) was added and stirred for 1 hour, and filtered. The filtrate was dissolved in toluene, and the layers were separated. The organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized with EA / Hexane to obtain Compound A-3 (15.9 g, 85%).: MS [M] = 292.0

(4) Synthesis of Compound A-4

1-aminoanthraquinone (10 g, 44.83 mmol) was dissolved in dimethylformamide (200 ml), bromine (Br ₂ 7.5 g, 47.07 mmol) was added thereto, and the mixture was stirred at about 40 ° C for 1 hour. After the reaction, the mixture was cooled to room temperature, 300 ml of distilled water was added thereto, stirred, and filtered. After filtration the filtrate was dried and compound A-4 (8.5 g, 85%) was obtained: MS [M] = 285.9

(5) Synthesis of Compound A-5

Compound A-4 (10 g, 33.2 mmol) was dissolved in DMSO (300 ml), dissolved in 2M aqueous KOH solution (60 ml), and then added to CuO (0.13 g, 1.7 mmol), followed by stirring at about 90 ° C. for 12 hours. After the reaction, the mixture was cooled to room temperature and filtered. 500 ml of distilled water was stirred in the filtrate and filtered. After filtration the filtrate was dried. The dried product was dissolved in toluene, and the layers were separated, and the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with EA / Hexane to give compound A-5 (4.2 g, 42%). MS [M] = 331.1

(6) Synthesis of Compound A

Compound A-5 (10 g, 30.2 mmol) and Compound A-3 (9.7 g, 33.2 mmol), sodium tert-butoxide (8.7 g, 96.1 mmol), Pd (t-Bu ₃ P) ₂ (0.062 g, 0.12 mmol) was dissolved in xylene (300 ml) and stirred under reflux for about 6 hours. After the reaction was cooled to room temperature, H2O (100 ml) was added and stirred for 1 hour, and filtered. The filtrate was dissolved in toluene, and the layers were separated. The organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized with EA / Hexane to obtain Compound A (14.5 g, 82%).: MS [M] = 587.1

Preparation Example 2 Synthesis of Compound B

(1) Synthesis of Compound B-1

Sodium 1-amino-4-bromoanthraquinone-2-sulfonic acid salt (10 g, 24.7 mmol) and phenol (3.5 g, 37.05 mmol) were dissolved in DMSO (100 ml), dissolved in 2M aqueous KOH solution (80 ml), and then CuO (0.09 g, 1.23 mmol) was added and stirred at about 80 ° C for 12 hours. After the reaction, the mixture was cooled to room temperature and filtered. 500 ml of distilled water was stirred in the filtrate and filtered. After filtration the filtrate was dried. The dried product was dissolved in toluene, and the layers were separated. The organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with EA / Hexane to obtain Compound B-1 (3.6 g, 35%). MS [M] = 417.03

(2) Synthesis of Compound B

Compound B-1 (10 g, 24 mmol) and 1-chloro dibenzothiophene (6.28 g, 28.8 mmol) were added to sodium tert-butoxide (6.92 g, 72 mmol), Pd (t-Bu ₃ P) ₂ (0.062 g, 0.12 mmol) was dissolved in xylene (300 ml) and stirred at reflux for about 6 hours. After the reaction was cooled to room temperature, H ₂ O (100 ml) was added and stirred for 1 hour, and filtered. The filtrate was dissolved in toluene, and the layers were separated. The organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized with EA / Hexane to obtain Compound B (9.77 g, 68%).: MS [M] = 599.05

Preparation Example 3 Synthesis of Compound C

(1) Synthesis of Compound C-1

Dissolve 1-amino-4-bromoanthraquinone (10 g, 33.23 mmol) and phenol (4.69 g, 49.85 mmol) in DMSO (100 ml), dissolve in 2M aqueous KOH solution (80 ml), and then remove CuO (0.13 g, 1.66 mmol). It put and stirred at about 80 degreeC for 12 hours. After the reaction, the mixture was cooled to room temperature and filtered. 500 ml of distilled water was stirred in the filtrate and filtered. After filtration the filtrate was dried. The dried product was dissolved in toluene, and the layers were separated. The organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with EA / Hexane to give compound C-1 (3.76 g, 55%). MS [M] = 315.09

(2) Synthesis of Compound C

Compound C-1 (10 g, 31.7 mmol) and 8-bromoisoquinoline (7.87 g, 38.04 mmol) were dissolved in sodium tert-butoxide (9.14 g, 95.1 mmol), Pd (t-Bu ₃ P) ₂ (0.081 g , 0.16 mmol) was dissolved in xylene (300 ml) and stirred at reflux for about 12 hours. After the reaction was cooled to room temperature, H ₂ O (100 ml) was added and stirred for 1 hour, and filtered. The filtrate was dissolved in toluene and the layers were separated and the organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized with EA / Hexane to give the compound C (9.95 g, 71%) .: MS [M] = 442.13

Preparation Example 4 Synthesis of Compound D

(1) Synthesis of Compound D-1

1-amino-4-bromoanthraquinone (10 g, 33.23 mmol) and bis (pinacolato) diborane (12.67 g, 49.85 mmol), potassium acetic acid (9.78 g, 99.69 mmol), Pd (dba) ₂ (0.38 g, 0.66 mmol) and PCy ₃ (0.37 g, 1.33 mmol) were added, 1,4-dioxane (400 ml) was added thereto, and the mixture was stirred under reflux for about 12 hours. After the reaction was cooled to room temperature and filtered. The organic layer was separated from the filtrate, and the organic layer was distilled under reduced pressure and recrystallized with EA / Hexane to obtain Compound D-1 (8.47 g, 73%).: MS [M] = 349.15

(2) Synthesis of Compound D-2

Compound D-1 (10 g, 28.6 mmol) and 3.5 M aqueous NaOH solution (120 ml) were added thereto, stirred at 60 ° C. for 10 minutes, and 30 mass% hydrogen peroxide (9.72 g, 85.8 mmol) was added dropwise, followed by stirring for about 2 hours. . After the reaction was cooled to room temperature and neutralized with hydrochloric acid at 0 ℃ and filtered. The organic layer was separated from the filtrate, and the organic layer was distilled under reduced pressure and recrystallized with EA / Hexane to obtain Compound D-2 (5.67 g, 83%). MS [M] = 239.06

(3) Synthesis of Compound D-3

Compound D-2 (10 g, 41.83 mmol), 2-bromopropane (7.65 g, 62.7 mmol) and NaOH (5.02 g, 125.5 mmol) were dissolved in DMF (100 ml) and stirred at reflux for 24 hours and then cooled to room temperature. . The organic layer was separated into an aqueous layer, and the organic layer was distilled under reduced pressure, and then recrystallized with EA / Hexane to obtain Compound D-3 (8.70 g, 74%). MS [M] = 281.11

(4) Synthesis of Compound D

Compound D-3 (10 g, 35.57 mmol) and 3-bromodibenzofuran (10.5 g, 42.68 mmol) were dissolved in sodium tert-butoxide (10.3 g, 106.7 mmol), Pd (t-Bu ₃ P) ₂ (0.09 g , 0.18 mmol) was dissolved in xylene (300 ml) and stirred at reflux for about 12 hours. After the reaction was cooled to room temperature, H ₂ O (100 ml) was added and stirred for 1 hour, and filtered. The filtrate was dissolved in toluene, and the layers were separated and the organic layer was dried over magnesium sulfate, distilled under reduced pressure and recrystallized with EA / Hexane to obtain Compound D (12.1 g, 76%) .: MS [M] = 447.15

Comparative Compound 1

Comparative Compound 2

Comparative Example Compound 3

<Example>

Example 1

3.000 g of compound A, a copolymer of benzyl methacrylate and methacrylic acid with a binder resin (molar ratio 70:30, acid value 80 KOH mg / g, weight average molecular weight 12,000 measured by GPC), molecular weight distribution (PDI) 2.0 g, Solid content (SC) 25%, solvent propylene glycol monomethyl ether acetate (PGMEA) containing 29.480 g, photoinitiator as Igacure-369 2.000 g, polyfunctional monomer photopolymerizable DPHA ( Nippon Gunpowder) 7.370g, 17.650g of PGMEA (propylene glycol monomethyl ether acetate), 40.000g of MBDG (diethylene glycol butyl methyl ether), and 1.016g of DIC F-475 as an additive were mixed to prepare a photosensitive resin composition. Prepared.

Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that Compound A was changed to Compound B in Example 1.

Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that Compound A was changed to Compound C in Example 1.

Example 4

A photosensitive resin composition was prepared in the same manner as in Example 1, except that Compound A was changed to Compound D in Example 1.

Comparative Example 1

A photosensitive resin composition was manufactured in the same manner as in Example 1, except that Compound A was changed to Comparative Example Compound 1 in Example 1.

Comparative Example 2

A photosensitive resin composition was prepared in the same manner as in Example 1, except that Compound A was changed to Comparative Example Compound 2 in Example 1.

Comparative Example 3

A photosensitive resin composition was prepared in the same manner as in Example 1, except that Compound A was changed to Comparative Example Compound 3 in Example 1.

Experimental Example

Substrate Fabrication and Contrast Ratio Evaluation

The photosensitive resin compositions according to Examples 1 to 4 and Comparative Examples 1 to 3 were used for substrate preparation, respectively. Specifically, the photosensitive resin compositions according to Examples 1 to 4 and Comparative Examples 1 to 3 are spin coated on glass (5 × 5 cm ² ), and preheated at 100 ° C. for 100 seconds (prebake: PrB). Was carried out to form a film.

40 mJ / cm ² exposure amount was irradiated to the whole surface of the board | substrate using the exposure machine without the photo mask on the board | substrate which formed the film.

The exposed substrate was then developed for 60 seconds in a developer (KOH, 0.05%). Subsequently, the substrate was post-baked (PB) for 20 minutes at 230 ° C., and the contrast ratio was measured using a contrast ratio (CR) meter.

Contrast ratio was calculated by dividing the brightest white screen (full white) by the darkest black screen (full black) (full white brightness / full black brightness).

The higher the contrast, the easier it is to distinguish black and white, and the higher the number, the better the contrast. That means better clarity on the display.

Contrast ratio (C / R) was measured by placing a measurement sample in an enclosed space and irradiating constant light under the sample. Light passing through the sample was detected by the meter and measured. The maximum value (Full White) and the minimum value (Full Black) were measured as the maximum value was 3000 cd, the minimum value was investigated at 1 cd. The measured contrast ratios are listed in Table 1 below.

Contrast Ratio [C / R]
[Max / min] Maximum value [cd] Minimum value [cd] Example 1 17,444 209.33 0.012 Example 2 17,692 230.00 0.013 Example 3 19,848 218.33 0.011 Example 4 17,778 213.33 0.012 Comparative Example 1 11,800 920.4 0.078 Comparative Example 2 12,844 1053.2 0.082 Comparative Example 3 11,355 1112.8 0.098

Referring to Table 1, the contrast ratio of the color filter substrate formed using the photosensitive resin compositions of Examples 1 to 4 of the present invention is higher than that of the color filter substrate formed using the photosensitive resin compositions of Comparative Examples 1 to 3. It was confirmed that excellent. That is, it is confirmed that Examples 1 to 4 of the present invention are easier to distinguish black and white than Comparative Examples 1 to 3 and have good sharpness on the display.

Claims (11)

Compound represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
L is a direct bond; O; Or S,
A is a halogen group; Hydroxyl group; Sulfonic acid groups; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Het is a substituted or unsubstituted heteroaryl group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Sulfonic acid groups; Or a sulfonate group,
r1 is an integer of 0 to 4, when r1 is 2 or more, R1 is the same or different,
r2 is an integer of 0 to 2, and when r2 is 2, R2 is the same or different. The compound of claim 1, wherein Formula 1 is represented by Formula 2:
[Formula 2]

In Chemical Formula 2,
L, A, R1, R2, r1 and r2 are the same as defined in Chemical Formula 1,
X is O; S; Or NR ',
R 'is hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring,
r3 is an integer of 0 to 4, when r3 is 2 or more, R3 is the same as or different from each other,
r4 is an integer of 0 to 3, and when r4 is 2 or more, R4 is the same as or different from each other. The compound of claim 1, wherein Formula 1 is represented by Formula 3:
[Formula 3]

In Chemical Formula 3,
L, A, R1, R2, r1 and r2 are the same as defined in Chemical Formula 1,
Y1 and Y2 are the same as or different from each other, and each independently CR '' or N,
R ″ is hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
R5 and R6 are the same as or different from each other, and each independently hydrogen; Or deuterium,
r5 is an integer of 0 to 2, when r5 is 2, R5 is the same as or different from each other,
r6 is an integer of 0 to 3, and when r6 is 2 or more, R6 is the same as or different from each other. The compound of claim 1, wherein R 1 is hydrogen. The compound of claim 1, wherein Het is a 2 to 5 ring substituted or unsubstituted heteroaryl group. The compound of claim 1, wherein the compound represented by Formula 1 is represented by one of the following formulas:

. A compound of any one of claims 1 to 6; Binder resins; Polyfunctional monomers; Photoinitiators; And a photosensitive resin composition comprising a solvent. The method according to claim 7, wherein the content of the compound represented by the formula (1) based on the total weight of solids in the photosensitive resin composition is 5% by weight to 60% by weight,
The binder resin content is 1% by weight to 60% by weight,
The content of the photoinitiator is 0.1% by weight to 20% by weight,
The content of the multifunctional monomer is 0.1% by weight to 50% by weight of the photosensitive resin composition. The photosensitive material manufactured using the photosensitive resin composition of Claim 7. A color filter comprising the photosensitive material according to claim 9. Display device including a color filter according to claim 10.