KR102247290B1 - Binder resin, photosensitive resin composition, pothoresist, color filter and display device - Google Patents

Abstract

The present specification is a structure represented by Chemical Formula 1; A structure represented by Chemical Formula 2; And a binder resin, a photosensitive resin composition, a photosensitive material, a color filter, and a display device including the structure represented by Chemical Formula 3.

Description

Binder resin, photosensitive resin composition, photosensitive material, color filter, and display device {BINDER RESIN, PHOTOSENSITIVE RESIN COMPOSITION, POTHORESIST, COLOR FILTER AND DISPLAY DEVICE}

The present specification relates to a binder resin, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.

In the recent LCD TV market, higher contrast and brightness are required than before. Among these, in order to improve luminance, conventionally, a pigment that is well known in the past was used to refine the luminance, or by changing the dispersibility and dispersing aid to improve the luminance, but recently, the required luminance level has reached its limit. Thus, in recent years, efforts to improve luminance by applying dyes have been continued.

Dyes have a higher solubility than pigments, so a dispersant, a dispersant, etc. may not be used, and a molar absorption coefficient is high, so that a desired color can be obtained with a small amount of use, which is advantageous in increasing luminance. However, when developing with an alkali developer after exposure to form a pattern, the dye is often washed out due to its good solubility compared to the pigment, and during the post-heating process (typically 230℃ ~ 250℃) due to inferior heat resistance compared to the pigment, it is decomposed and sublimated and patterned. There is a disadvantage of causing discoloration of the pixels.

Chemical resistance also tends to be inferior to pigments. In the case of chemical resistance of the pigment type composition, it is generally possible to improve by introducing an unsaturated ethylenic reactor (introduction of a crosslinking site) in the binder resin. It will double.

Japanese Published Literature Special Publication Hei 9-87534

The present specification provides a binder resin, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.

An exemplary embodiment of the present specification is a structure represented by the following formula (1); A structure represented by the following formula (2); And it provides a binder resin including a structure represented by the following formula (3).

[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,

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

r4 is an integer from 0 to 5, and when r4 is 2 or more, R4 is the same or different,

L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,

A is a thermosetting group.

An exemplary embodiment of the present specification is the binder resin; Dye compounds; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing 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 use of the binder resin of the present specification can improve the processability and reliability of the photosensitive resin composition by supplementing the heat resistance problem that occurs during the post-heating process and improving chemical resistance.

Specifically, in the color filter manufacturing process, a crosslinked matrix is formed by a photocuring reaction during exposure to prevent the elution of the exposed dye during the development process, and a crosslinked matrix is formed once again by a thermal curing reaction during the postheating process. It is possible to improve the heat resistance and chemical resistance of the photosensitive resin composition.

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

In the present specification, when a member is positioned “on” another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary. For example, a structure represented by the following formula (1); A structure represented by the following formula (2); And the binder resin including the structure represented by the following formula (3) may further include a structure represented by the following formula (4).

는 다른 치환기 또는 결합부에 결합되는 부위를 의미할 수 있고, 본 명세서의 바인더 수지의 주쇄에 연결되는 부분을 의미할 수 있다. In this specification,

May mean a portion bonded to another substituent or a bonding portion, and may mean a portion connected to the main chain of the binder resin of the present specification.

According to an exemplary embodiment of the present specification, the structure represented by the following formula (1); A structure represented by the following formula (2); And it provides a binder resin including a structure represented by the following formula (3).

The use of the binder resin according to the exemplary embodiment of the present specification is used to improve the processability and reliability of the photosensitive resin composition composed of a dye alone or a dye-pigment mixture dispersion by supplementing the heat resistance problem of the dye compound that occurs during the post-heating process and also improving the chemical resistance. have.

The binder resin according to an exemplary embodiment of the present specification has a structure represented by the following formula (1) capable of heat curing; A structure represented by the following formula (2) capable of photocuring; And a structure represented by Formula 3 below which imparts developability to an alkaline developer.

As a result, a crosslinked matrix is formed by a photocuring reaction during exposure in the color filter manufacturing process to prevent elution of the exposed dye during the development process, and a crosslinked matrix is formed once again by a thermal curing reaction during the post-heating process. Heat resistance and chemical resistance of the photosensitive resin composition according to the exemplary embodiment of the present specification may be improved.

Unlike the conventional binder resin in which an unsaturated double bond group is introduced by heating addition reaction of a monomer such as methacrylic acid or acrylic acid to the epoxy group in the binder resin after completion of the binder polymerization reaction, the binder resin of the present invention is represented by the following formula (2). When the photocurable group is introduced, there is no alcohol group, so there is an effect of improving the dye elution problem during the development process. In addition, it is possible to spontaneously photocure without adding a separate photoinitiator for photocuring of the unsaturated double bonded group.

In the case of a conventional binder resin in which an unsaturated double bond group is introduced, it is difficult to introduce an acid group into the binder resin due to the possibility of gelation due to the reaction between the epoxy group and the acid period in the binder resin because the double bond introduction reaction is performed at a high temperature. Accordingly, the binder resin may remain as a residue during development, but in the case of the present invention, acid groups can be introduced into the binder resin, so there is no problem in developability.

In other words, the binder resin of the present invention is composed of a copolymer of three types of unsaturated double bonded monomers according to the roles of each of the thermosetting group, photocuring group, and alkali-soluble group.

The thermosetting group includes a monomer having a carboxylic acid group included in the dye or dye polymer or a group capable of curing with a binder resin (eg, epoxy, aziridine, oxazoline, etc.), and is directly bonded to the dye or bonded between the binder resin. By improving the heat resistance and chemical resistance of the dye.

The photocuring group includes a monomer containing a benzophenone group to improve heat resistance and chemical resistance by forming a matrix that can hold the dye more tightly by bonding between the binder resins during exposure or between the binder resin and the unsaturated double bond crosslinking agent. .

An alkali-soluble group (for example, methacrylic acid, acrylic acid, etc.) is introduced to impart developability of the composition to an alkali developer.

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; -OH; Carbonyl group; Ester group; -COOH; Imide group; Amide group; Alkoxy group; Alkyl group; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Arylalkyl group; Phosphine group; Sulfonate group; Amine group; Aryl group; Heteroaryl group; Silyl group; Boron group; Acryloyl group; Acrylate group; Ether group; And it means that it is substituted with one or more substituents selected from the group containing a heterocyclic group containing one or more of N, O, S, or P atoms, or does not have any substituents.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but the number of carbon atoms of the alkyl group may be 1 to 30. 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, n-oxy In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and particularly preferably a cyclopentyl group or a cyclohexyl group, but is not limited thereto. .

In the present specification, the alkylene group means that the alkane has two bonding sites. 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, for example, 1 to 30 carbon atoms. In addition, it may have 1 to 20 carbon atoms, and may have 1 to 10 carbon atoms.

In the present specification, the cycloalkyl group is not particularly limited, but according to an exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. 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, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 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. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the number of carbons is not particularly limited, but has 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl 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 to these.

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 alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

In the present specification, "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The notation of'(meth)acrylic acid' has the same meaning.

An exemplary embodiment of the present specification is a structure represented by the following formula (1); A structure represented by the following formula (2); And it provides a binder resin including a structure represented by the following formula (3).

[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,

R1 to R5 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group,

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

r4 is an integer from 0 to 5, and when r4 is 2 or more, R4 is the same or different,

L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,

A is a thermosetting group.

The photocurable group including the structure represented by Formula 2 in the present specification contributes to the improvement of heat resistance by providing a photoinitiator effect to the binder resin during the exposure process to cause a crosslinking reaction.

On the other hand, in the structure represented by Chemical Formula 2, when R3 or R4 is a hydroxy group (-OH), it functions as an ultraviolet absorber, not a photocuring function like the photocurable group of the present specification. That is, in the structure represented by Chemical Formula 2, when R3 or R4 is a hydroxy group (-OH), it is used for the purpose of improving pattern defects by absorbing ultraviolet rays reflected back when forming a color filter. In the structure represented by Formula 2, the case where R3 or R4 is a hydroxy group (-OH) may correspond to Comparative Example 2 to be described later.

Specifically, in the structure represented by Chemical Formula 2, when R3 or R4 is a hydroxy group (-OH), when the development process is performed using a photosensitive resin composition including the structure represented by Chemical Formula 2, during exposure Since the hydroxy group serves only as an ultraviolet absorber, exposure sensitivity may be lowered.

In the exemplary embodiment of the present specification, the thermosetting group is a binder resin having any one of the following structures.

In the above structure, R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted methyl group.

In the exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted methylene group.

In the exemplary embodiment of the present specification, L1 to L4 are methylene groups.

In the exemplary embodiment of the present specification, R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R11 to R18 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an exemplary embodiment of the present specification, R11 to R18 are hydrogen.

According to an exemplary embodiment of the present specification, Formula 1 may be represented by Formula 1-1 below, but is not limited thereto.

[Formula 1-1]

In an exemplary embodiment of the present specification, Formula 2 may be represented by Formula 2-1 below.

[Formula 2-1]

In Formula 2-1, R2 to R4, L3, r3, and r4 are as defined in Formula 2.

In the exemplary embodiment of the present specification, Formula 2 may be represented by Formula 2-2 below, but is not limited thereto.

[Formula 2-2]

In the exemplary embodiment of the present specification, Formula 3 may be represented by Formula 3-1 below, but is not limited thereto.

[Chemical Formula 3-1]

In the exemplary embodiment of the present specification, the binder resin further includes at least one of the structures represented by the following Chemical Formula 4 or 5.

[Formula 4]

[Formula 5]

In Formulas 4 and 5,

L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,

R41, R42, R51 and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,

r42 is an integer from 0 to 5, and when r42 is 2 or more, R42 is the same as or different from each other,

r52 is an integer from 0 to 11, and when r52 is 2 or more, R52 is the same as or different from each other.

In the exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted methylene group.

In the exemplary embodiment of the present specification, L5 is a methylene group.

In the exemplary embodiment of the present specification, L6 is a methylene group.

In the exemplary embodiment of the present specification, R41, R42, R51, and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, r42 is an integer of 0 to 5, when r42 is 2 or more, R42 is the same as or different from each other, r52 is an integer of 0 to 11, and r52 is 2 or more R52 is the same as or different from each other.

In the exemplary embodiment of the present specification, R41, R42, R51, and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, r42 is an integer of 0 to 5, when r42 is 2 or more, R42 is the same as or different from each other, r52 is an integer of 0 to 11, and r52 is 2 or more R52 is the same as or different from each other.

In the exemplary embodiment of the present specification, R41, R42, R51, and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, r42 is an integer of 0 to 5, when r42 is 2 or more, R42 is the same as or different from each other, r52 is an integer of 0 to 11, and r52 is 2 or more R52 is the same as or different from each other.

In an exemplary embodiment of the present specification, R41, R42, and R52 are hydrogen.

In the exemplary embodiment of the present specification, R51 is a substituted or unsubstituted methyl group.

In an exemplary embodiment of the present specification, R51 is a methyl group.

In an exemplary embodiment of the present specification, Chemical Formula 4 may be represented by Chemical Formula 4-1 below.

[Formula 4-1]

In an exemplary embodiment of the present specification, Chemical Formula 5 may be represented by Chemical Formula 5-1 below.

[Chemical Formula 5-1]

In the exemplary embodiment of the present specification, 10 to 90 mol% of the structure represented by Chemical Formula 1; 1 to 20 mol% of the structure represented by Chemical Formula 2; And it provides a binder resin containing 5 to 40 mol% of the structure represented by the formula (3).

100 mol%, which is the standard of mol% of each structure, means that all monomers included in the binder resin are included.

In addition, in the exemplary embodiment of the present specification, 10 to 80 mol% of the structure represented by Chemical Formula 1; 1 to 20 mol% of the structure represented by Chemical Formula 2; 5 to 40 mol% of the structure represented by Chemical Formula 3; And it provides a binder resin containing 10 to 50 mol% of the structure represented by the formula (4).

In another exemplary embodiment of the present specification, 10 to 80 mol% of the structure represented by Chemical Formula 1; 1 to 20 mol% of the structure represented by Chemical Formula 2; 5 to 40 mol% of the structure represented by Chemical Formula 3; And it provides a binder resin containing 10 to 50 mol% of the structure represented by the formula (5).

By satisfying the above range, the binder resin according to the exemplary embodiment of the present specification may have excellent thermosetting properties, photocurability, and alkali solubility properties.

Specifically, when the structure represented by Formula 1 is within the above range, sufficient thermal curing properties can be achieved, and stability of the binder resin itself can be secured.

When the structure represented by Chemical Formula 2 is within the above range, sufficient photo-curing properties may be exhibited, and a decrease in heat resistance of the resin may be prevented.

When the structure represented by Chemical Formula 3 is within the above range, sufficient developability may be ensured, and over-development may prevent pattern dropout from being caused.

When the structure represented by Chemical Formula 4 or 5 is within the above range, etching resistance may be improved, developability may be reduced, and thus a residue may be prevented from occurring.

In an exemplary embodiment of the present specification, the weight average molecular weight of the binder resin is 3,000 to 50,000. Preferably it may be 5,000 to 20,000.

When the weight average molecular weight of the binder resin is within the above range, sufficient heat resistance and chemical resistance may be ensured, and developability may be prevented from deteriorating.

The weight average molecular weight is one of average molecular weights whose molecular weight is not uniform and the molecular weight of a certain polymer material is used as a reference, and is a value obtained by averaging the molecular weights of component molecular species of a polymer compound having a molecular weight distribution by weight fraction.

The weight average molecular weight can be measured through Gel Permeation Chromatography (GPC) analysis.

According to an exemplary embodiment of the present specification, the acid value of the binder resin is 20 to 200 KOH mg/g.

When the acid value of the binder resin is within the above range, it is possible to prevent deterioration of developability, and it is possible to prevent over-development resulting in pattern dropout.

The acid value of the binder resin can be measured by titration with a 0.1N concentration of potassium hydroxide (KOH) methanol solution.

An exemplary embodiment of the present specification is the binder resin; Dye compounds; Polyfunctional monomers; Photoinitiators; And it provides a photosensitive resin composition containing a solvent.

The photosensitive resin composition may further include at least one of a pigment compound in addition to the dye compound. For example, the photosensitive resin composition may include only the dye compound, but may include the dye compound and at least one pigment compound.

The dye compound and the pigment compound may include a metal-complex-based compound; Azo-based compounds; Metal azo-based compounds; Quinophthalone-based compounds; Isoindoine-based compounds; Methine-based compounds; Phthalocyanine-based compounds; Metal phthalocyanine-based compounds; Porphyrin-based compounds; Metal porphyrin-based compounds; Tetra aza porphyrin-based compounds; Metal tetra aza porphyrin series compounds; Cyanine-based compounds; Xanthene-based compounds; Metal dipyrromethane series compounds; Boron dipyrromethane series compounds; Metal dipyrromethane series compounds; Anthraquinone-based compounds; Diketopyrrolopyrrole-based compounds; Triarylmethane series compounds; And one or more types may be selected from the group consisting of perylene-based compounds. Preferably, the dye compound may be a triarylmethane-based Blue dye.

The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, and specifically, 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, trishydroxyethyl isocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate It may be a species or a mixture of two or more. Preferably, the polyfunctional monomer may be dipentaerythritol hexaacrylate.

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

The acetophenone 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-hydroxycyclohexylphenyl ketone, 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, but is not limited thereto.

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, etc. , Is not limited thereto.

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

The oxime compound is 1,2-octadione,-1-(4-phenylthio)phenyl,-2-(o-benzoyloxime) (Shibagagi Co., Ltd., Shijii124), ethanone,-1-(9 -Ethyl)-6-(2-methylbenzoyl-3-yl)-,1-(O-acetyloxime)(CGI 242), N-1919 (Adeca), and the like, but are not limited thereto.

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, propene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxy Propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol may be one or more selected from the group consisting of monomethyl ether, but is not limited thereto.

In an exemplary embodiment of the present specification, based on the total weight of the photosensitive resin composition, the content of the binder resin is 3 to 10% by weight, the content of the dye compound is 1 to 5% by weight, and the polyfunctional monomer Is 3 to 10% by weight, the photoinitiator is 0.1 to 10% by weight, and the solvent is 65 to 90% by weight.

In an exemplary embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the dye compound is 4 to 20% by weight, the content of the binder resin is 20 to 50% by weight, and the multi-tube The content of the functional monomer is 20 to 50% by weight, and the content of the photoinitiator is 1 to 5% by weight.

When the content of the dye compound is within the above range, it is possible to prevent deterioration of the coloring power, and to prevent the pattern from dropping out due to insufficient transparent materials that may constitute the matrix.

When the content of the binder resin is within the above range, a phenomenon of insufficient developability can be prevented, and the viscosity of the photosensitive resin composition can be prevented from becoming too high.

When the content of the polyfunctional monomer is within the above range, the degree of crosslinking may be lowered to prevent the pattern from falling off, and the degree of crosslinking may be too high to prevent the pattern residue from remaining during development in the non-exposed part.

When the content of the photoinitiator is within the above range, it is possible to prevent the occurrence of pattern dropout due to decrease in exposure sensitivity, and as a result of excessive surface hardening during exposure, the pattern shape is reverse trapezoidal (trapezoidal pattern is common). Can be prevented.

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 basis of the solid content and the weight percent based on the solid content of each component can be measured by a general analysis means used in the art, such as liquid chromatography or gas chromatography.

According to an exemplary embodiment of the present specification, the photosensitive 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 photosensitive resin composition.

According to an exemplary embodiment of the present specification, the photosensitive resin composition comprises one or two or more additives selected from the group consisting of a photo-crosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent. Includes additionally.

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 photosensitive resin composition.

The photo-crosslinking 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, and 3,3,4,4-tetra(t-butylperoxycarbonyl)benzophenone; Fluorenone compounds, such as 9-fluorenone, 2-chloro-9-prorenone, and 2-methyl-9-fluorenone; Thioxanthone type 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, etc. 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 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 compounds such as pyrano[6,7,8-ij]-quinolizin-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; At least one selected from the group consisting of 2-benzoylmethylene and 3-methyl-b-naphthothiazoline may be used.

The curing accelerator is used to increase curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzooxazole, 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.

The adhesion promoter used in the present specification includes methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, and methacryloyloxy propyldimethoxysilane One or more of methacryloyl silane coupling agents such as may be selected and used, and one or more of octyltrimethoxy silane, dodecyltrimethoxy silane, octadecyltrimethoxy silane, etc. as an alkyl trimethoxy silane. You can choose and use it.

The surfactant is a silicone surfactant or a fluorine surfactant, and specifically, the silicone 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, etc. can be used. (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 are not limited thereto.

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-based 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 diethylester, 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 ester); Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-di-β-naphthyl-p-phenylenediamine Based secondary antioxidants; Thio such as dilauryldisulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane Based secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, 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 the present invention 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, pyrogarol, benzoquinone, 4,4-thiobis(3-methyl-6-t-butylphenol), 2,2- Methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine (phenothiazine) may include one or more selected from the group consisting of, but is not limited to these, and the technology in the art It may include those generally known in the field.

The dispersant may be used as a method of adding the pigment inside to the pigment in the form of surface treatment in advance, or adding it to the pigment outside. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric surfactants, and the like can be used. These may be used individually or in combination of two or more.

Specifically, the dispersant is polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, carboxylate, There may be at least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines, but is not limited thereto.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Including a compound, but not limited thereto, all those commonly used in the art may be used.

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

In more detail, the photosensitive resin composition of the present specification is applied on a substrate by an appropriate method to form a photosensitive material in the form of a thin film or pattern.

The coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like may be used, and generally, a spin coating method is widely used. In addition, after forming the coating film, a part of the residual solvent can be removed under reduced pressure in some cases.

Light sources for curing the photosensitive resin composition according to the present specification include, for example, mercury vapor arcs, carbon arcs, Xe arcs, etc. that emit light having a wavelength of 250 nm to 450 nm, but are not limited thereto. .

The photosensitive resin composition according to the present specification is a pigment dispersion 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 a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode. , Photosensitive material for overcoat layer formation, column spacer photosensitive material, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There is no particular limitation.

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

The color filter may include a thermosetting group having a structure represented by Chemical Formula 1; A photocurable group including the structure represented by Formula 2; And a photosensitive resin composition including a binder resin having a structure represented by Formula 3 above. A color filter may be formed by applying the photosensitive resin composition on a substrate to form a coating film, and exposing, developing, and curing the coating film.

The photosensitive resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance and chemical resistance, and there is no problem in developability, so that a color filter having high color reproducibility and high luminance and contrast ratio can be provided even by a curing process when manufacturing a color filter. I can.

The substrate may be a glass plate, a silicon wafer, and a plate made of a plastic substrate such as polyethersulfone (PES) or polycarbonate (PC), 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 grid-like black pattern called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving the contrast. Chrome can be used as a material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by etching treatment may be used. However, in consideration of the high cost of the process, high reflectance of chromium, and environmental pollution due to chromium waste, a resin black matrix using a pigment dispersion method capable of fine processing can be used.

The black matrix according to the exemplary embodiment of the present specification may use a black pigment or a black dye as a color material. For example, carbon black may be used alone or a mixture of carbon black and a colored pigment may be used.At this time, since a colored pigment having insufficient light-shielding property is mixed, the strength of the film or adhesion to the substrate decreases even if the amount of the color material is relatively increased. There is an advantage that does not work.

It provides a display device including the color filter according to the present specification.

The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), and a thin film transistor. It may be one of a thin film transistor (LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, examples will be described in detail in order to describe the present specification in detail. However, the embodiments according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The embodiments of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

<Example>

<Synthesis Example of Binder>

<Synthesis Example 1>

In the reaction vessel, benzophenone methacrylate represented by the following formula (2-2) / styrene represented by the following formula (4-1) / glycidyl methacrylate represented by the following formula (1-1) / represented by the following formula (3-1) The resulting methacrylic acid was added in an amount of 11, 31, 45, 13% by weight, respectively, based on the total weight of the solid content of the binder resin, and then mixed with a solvent (propylene glycol monomethyl ether acetate, Cas No. 108-65-6) and nitrogen. The temperature was raised to 60°C in an atmosphere. Then, 10 parts by weight of the thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) based on the total weight of the binder resin solid content was added and reacted for 16 hours to prepare a binder resin.

The prepared binder resin had an acid value of 85 KOH mg/g and a weight average molecular weight of 9,000.

[Formula 1-1]

[Formula 2-2]

[Chemical Formula 3-1]

[Formula 4-1]

<Synthesis Example 2>

In the reaction vessel, benzophenone methacrylate represented by the formula 2-2 structure / glycidyl methacrylate represented by the formula 1-1 / methacrylic acid represented by the formula 3-1, the total weight of the binder resin solid content Based on, each of 17, 70, 13% by weight was added and mixed with a solvent, and the temperature was raised to 60°C in a nitrogen atmosphere. Then, 10 parts by weight of the thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) based on the total weight of the binder resin solid content was added and reacted for 16 hours to prepare a binder resin.

The prepared binder resin had an acid value of 87 KOH mg/g and a weight average molecular weight of 9,500.

<Synthesis Example 3>

In the reaction vessel, benzophenone methacrylate represented by the structure of the formula 2-2 / cyclohexyl methacrylate represented by the structure of the following formula 5-1 / glycidyl methacrylate represented by the formula 1-1 / the above formula Methacrylic acid represented by 3-1 was added in an amount of 10, 41, 38, and 13% by weight, respectively, based on the total weight of the solid content of the binder resin, and then mixed with a solvent and heated to 60°C in a nitrogen atmosphere. Then, 10 parts by weight of the thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) based on the total weight of the binder resin solid content was added and reacted for 16 hours to prepare a binder resin.

The prepared binder resin had an acid value of 84 KOH mg/g and a weight average molecular weight of 9,200.

[Chemical Formula 5-1]

<Synthesis Example of Photosensitive Resin Composition>

<Example 1>

Triarylmethane blue dye 3 g and the binder resin prepared in Synthesis Example 1 6 g, dipentaerythritol hexaacrylate 6 g as a polyfunctional monomer, OXE-02 0.8 g as a photoinitiator, propylene glycol monomethyl as a solvent 84.2 g of ether acetate were mixed, and the mixture was stirred for 3 hours to prepare a photosensitive resin composition.

<Example 2>

A photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Synthesis Example 2 was used instead of the binder resin prepared in Synthesis Example 1.

<Example 3>

A photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Synthesis Example 3 was used instead of the binder resin prepared in Synthesis Example 1.

<Comparative Example>

<Comparative Synthesis Example 1>

Styrene represented by Chemical Formula 4-1/glycidyl methacrylate represented by Chemical Formula 1-1/methacrylic acid represented by Chemical Formula 3-1 in a reaction vessel based on the total weight of the solid content of the binder resin, respectively After adding 42, 45, 13% by weight, the mixture was mixed with a solvent, and the temperature was raised to 60°C in a nitrogen atmosphere. Then, 10 parts by weight of the thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) based on the total weight of the binder resin solid content was added and reacted for 16 hours to prepare a binder resin.

The prepared binder resin had an acid value of 88 KOH mg/g and a weight average molecular weight of 9,300.

<Comparative Synthesis Example 2>

In the reaction vessel, R3 in Formula 2 is a hydroxy group (-OH), r3 is 1, R4 is hydrogen, r4 is 0, L3 is a methylene group, and R2 is a methyl group. Styrene represented by Formula 4-1 / Glycidyl methacrylate represented by Formula 1-1 / Methacrylic acid represented by Formula 3-1 based on the total weight of the solid content of the binder resin, respectively, 11, 31, It was added at 45 and 13% by weight, mixed with a solvent, and heated to 60°C in a nitrogen atmosphere. Thereafter, 10 parts by weight of the thermal polymerization initiator v-65 (2,2'-Azobis (2,4-dimethylvaleronitrile) was added and reacted for 16 hours based on the total weight of the binder resin solid content to prepare a binder resin. The acid value of is 85 KOH mg/g, and the weight average molecular weight is 9,000.

<Comparative Example 1>

A photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Comparative Synthesis Example 1 was used instead of the binder resin prepared in Synthesis Example 1.

<Comparative Example 2>

A photosensitive resin composition was prepared in the same manner as in Example 1, except that 6 g of the binder resin prepared in Comparative Synthesis Example 2 was used instead of the binder resin prepared in Synthesis Example 1.

[Experimental Example]

Measurement of dye elution degree and chemical resistance result of photosensitive resin composition

In order to measure the degree of dye elution of the photosensitive resin compositions obtained in Examples 1 to 3 and Comparative Examples 1 and 2, the photosensitive resin composition was spin-coated on glass, followed by heat treatment at about 100° C. for 2 minutes ( prebake) to form a film.

^{After exposing the film with an energy of 50 to 100 mJ/cm 2} under a high pressure mercury lamp using a photomask, the pattern was developed using an aqueous KOH alkali solution and washed with deionized water.

At this time, the degree to which the blue color of the dye-based property appears was measured with the naked eye, and the results are shown in "Dye elution degree" in Table 1 below with the following symbols.

O: It doesn't come out at all.

△: Rising at the beginning of the developing process, but no longer rising after a certain period of time.

X: It continues to erupt throughout the entire process.

In addition, in order to observe the chemical resistance of the coloring composition, the glass substrate on which the pattern was formed was immersed in methylpyrrolidone (NMP), and then at 80°C, the degree of the color material emanating after 40 minutes was visually observed. The results are shown in "Methylpyrrolidone (NMP) chemical resistance results" in Table 1 below.

O: It doesn't come out at all.

△: It comes out a little.

X: It comes out dark or the pattern is peeled off from the glass substrate.

Degree of dye elution Methylpyrrolidone (NMP) chemical resistance results Example 1 O O Example 2 O O Example 3 O O Comparative Example 1 △ X Comparative Example 2 X X

According to Table 1, it was confirmed that Examples 1 to 3 showed excellent properties in dye elution and chemical resistance, whereas Comparative Examples 1 and 2 showed poor results in dye elution and chemical resistance.

Heat resistance evaluation of photosensitive resin composition

In order to confirm the heat resistance of the photosensitive resin composition, experiments were conducted in the following order.

(1) Luminance measurement after post-baking at 240℃ for 20 min

(2) Luminance measurement after additional baking at 240℃ for 60 min

(3) Measurement of luminance change width between (1)-(2)

(4) Brightness change rate (%) = (3)*100/(1) to confirm heat resistance

The smaller the luminance change rate, the better the heat resistance, and what was evaluated by the above procedure is shown in Table 2 below.

Luminance after post heat treatment
(One) Brightness after additional heat treatment
(2) Width of change
(3) Rate of change
(4) Example 1 11.7 11.4 0.3 2.6% Example 2 11.7 11.4 0.3 2.6% Example 3 11.7 11.3 0.4 3.4% Comparative Example 1 11.6 10.6 1.0 8.6% Comparative Example 2 11.5 10.0 1.5 13.0%

According to Table 2, in the case of Examples 1 to 3, the difference between the luminance after the post-heat treatment and the luminance after the additional heat treatment was small, and the heat resistance was excellent, whereas in Comparative Examples 1 and 2, the luminance change rate was 8 to 13% It can be seen that heat resistance is inferior to 3 compared to.

Measurement of the minimum pattern size remaining after the development process

Using the photosensitive resin compositions according to Examples 1 to 3 and Comparative Examples 1 and 2, the minimum pattern size remaining after the development process was measured. The results are shown in Table 3 below.

Minimum pattern size remaining after development process (μm) Example 1 10 Example 2 9 Example 3 10 Comparative Example 1 13 Comparative Example 2 25

According to Table 3, in Examples 1 to 3 and Comparative Example 1, there was no difference in the minimum pattern size remaining after the development process, whereas in Comparative Example 2, all patterns of less than 25 μm were eliminated.

This can be seen that in the case of the benzophenone monomer containing a hydroxy group (-OH) contained in the binder resin used in Comparative Example 2, it only serves as an ultraviolet absorber during exposure, resulting in a decrease in exposure sensitivity.

Claims (10)

10 to 90 mol% of the structure represented by the following formula (1); 1 to 20 mol% of the structure represented by the following formula (2); And a binder resin containing 5 to 40 mol% of the structure represented by the following formula (3):
[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,
R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
r3 is an integer from 0 to 4, and when r3 is 2 or more, R3 is the same as or different from each other,
r4 is an integer from 0 to 5, and when r4 is 2 or more, R4 is the same as or different from each other,
L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
A is a thermosetting group. The binder resin according to claim 1, wherein the thermosetting group has any one of the following structures:

.
In the above structure,
R ₁₁ to R ₁₈ are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group. The binder resin of claim 1, wherein the binder resin further comprises at least one of the structures represented by the following Chemical Formula 4 or 5:
[Formula 4]

[Formula 5]

In Formulas 4 and 5, L5 and L6 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
R41, R42, R51 and R52 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
r42 is an integer from 0 to 5, and when r42 is 2 or more, R42 is the same as or different from each other,
r52 is an integer from 0 to 11, and when r52 is 2 or more, R52 is the same as or different from each other. delete The binder resin according to claim 1, wherein the binder resin has a weight average molecular weight of 3,000 to 50,000. Binder resin; Dye compounds; Polyfunctional monomers; Photoinitiators; And as a photosensitive resin composition containing a solvent,
The binder resin has a structure represented by the following Chemical Formula 1; A structure represented by the following formula (2); And the photosensitive resin composition comprising a structure represented by the following formula (3):
[Formula 1]

[Formula 2]

[Formula 3]

In Formulas 1 to 3,
R1 to R5 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group,
r3 is an integer from 0 to 4, and when r3 is 2 or more, R3 is the same as or different from each other,
r4 is an integer from 0 to 5, and when r4 is 2 or more, R4 is the same as or different from each other,
L1 to L4 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
A is a thermosetting group. The method according to claim 6, based on the total weight of the solid content in the photosensitive resin composition, the content of the dye compound is 4 to 20% by weight, the content of the binder resin is 20 to 50% by weight, the content of the polyfunctional monomer Is 20 to 50% by weight, and the content of the photoinitiator is 1 to 5% by weight of the photosensitive resin composition. A photosensitive material manufactured using the photosensitive resin composition according to claim 6. A color filter comprising the photosensitive material according to claim 8. A display device comprising the color filter according to claim 9.