KR20200039356A - Compound, colorant composition, photosensitive resin composition, photoresist, color filter and display device - Google Patents

Abstract

The present specification provides a compound represented by chemical formula 1, a colorant composition comprising the same, a photosensitive resin composition, a photosensitive material, a color filter, and a display apparatus. The compound according to an embodiment of the present specification can be used as a color material to improve color reproduction, luminance, and contrast ratio.

Description

Compound, color material composition, photosensitive resin composition, photosensitive material, color filter and display device {COMPOUND, COLORANT COMPOSITION, PHOTOSENSITIVE RESIN COMPOSITION, PHOTORESIST, COLOR FILTER AND DISPLAY DEVICE}

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

In recent years, in color filters, performance characterized by high luminance and high contrast ratio is required. In addition, one of the main objectives of the development of a display device is to differentiate display device performance by improving color purity and improve productivity in a manufacturing process.

Since the pigment type used as a color material of a color filter existed in a color photoresist in a particle dispersion state, it was difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, aggregation and dispersibility are poor in a color filter, and multiple scattering of light occurs due to large particles aggregated. Scattering of the polarized light has been pointed out as a main factor that lowers the contrast ratio. Efforts are being made to improve the luminance and contrast ratio through ultra-fine atomization and dispersion stabilization of the pigment, but the degree of freedom is limited in selecting a color material for realizing color coordinates for a high-purity display device. In addition, the pigment dispersion method using a color material, especially a pigment, which has already been developed, has reached a limit in improving the color purity, brightness and contrast ratio of a color filter using the same.

Accordingly, there is a need to develop a new color material capable of increasing color purity to improve color reproduction, luminance and contrast ratio.

Korean Patent Publication No. 2001-0009058

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

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,

R9 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group, or adjacent substituents combine with each other to form a ring,

R 'is a substituted or unsubstituted aryl group,

M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure,

M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or M1 and M2 combine with each other to form a ring,

X is an anionic group,

a is 0 or 1,

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

X1 and X2 are the same as or different from each other, and each independently -O- or -NR-,

R is hydrogen; Or a substituted or unsubstituted alkylene group,

r7 and r8 are integers from 0 to 2, when r7 is 2, R7 is the same or different from each other, and when r8 is 2, R8 is the same or different from each other,

r9 and r10 are integers from 0 to 3, when r9 is 2 or more, R9 is the same or different from each other, and when R10 is 2 or more, R10 is the same or different from each other,

r11 is an integer from 0 to 5, and when r11 is 2 or more, R11 is the same as or different from each other,

r12 and r13 are integers from 0 to 4, and when r12 is 2 or more, R12 is the same or different from each other, and when r13 is 2 or more, R13 is the same or different from each other.

One embodiment of the present specification provides a color material composition comprising the compound.

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

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

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

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

The compound according to one embodiment of the present specification may be used as a color material in a photosensitive resin composition, and when used as a color material, has excellent heat resistance.

In addition, the compound according to the present specification can reduce the dispersion process by having excellent solubility in an organic solvent, and, unlike the conventional process of applying a pigment, a compound can be used as a colorant in an economical manner. .

In addition, the compound according to an exemplary embodiment of the present specification may be used as a color material to improve color reproduction, luminance, and contrast ratio.

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

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

In the present specification, when a part “includes” a certain component, this means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

One embodiment of the present specification provides the compound represented by Chemical Formula 1.

The compound represented by Formula 1 according to the present specification has excellent solubility in an organic solvent. Specifically, the aryl group substituted with N of the core structure of Formula 1 has a thio group represented by -S-R1 or -S-R2, and an alkylene group represented by L1 or L3 substituted by N By being substituted with hindered phenol, solubility can be increased due to bulky substituents.

Due to the increase in solubility, it is possible to prevent agglomeration between color materials, and through this, it is possible to increase the economic efficiency by reducing the amount of material required for color material dispersion.

In addition, when the aryl group substituted with N of the core structure of Formula 1 has a thio group represented by -S-R1 or -S-R2, the fluorescence intensity is higher than when the xanthene-based compound does not have a thio group. It can be reduced to improve the contrast ratio (CR, Contrast Ratio) without adding additional materials, and can have excellent heat resistance.

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

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

Means a site that is attached to another substituent or linkage.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group (-OH); Thiol group (-SH); -COOH; Carbonyl group; Ester groups; Imide group; Amide group; Anionic groups; Alkoxy groups; Alkyl groups; Cycloalkyl group; Alkenyl group; Cycloalkenyl group; Aryl group; Heterocyclic group; Silyl group; Alkyl sulfoxy group; Aryl sulfoxyl group; Boron group; Acryloyl group; Acrylate groups; Ether group; It means that it has been substituted with one or more substituents selected from the group containing heterocyclic groups and anionic groups 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 thio group may be represented by -S-R '' ', and the R' '' may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. When R '' is an alkyl group, it may be an alkylthio group, and when R '' 'is an aryl group, it may be an arylthio group. In the alkylthio group and the arylthio group, the description of 'alkyl group' of the present specification is applied to alkyl, and the description of 'aryl group' of the present specification is applied to aryl.

In the present specification, the anionic group may be represented by X, has a chemical bond with the structure of Formula 1, and the anionic group is not particularly limited, such as US Patent No. 7,939,644, Japanese Patent Publication No. 2006-003080, Japan Japanese Patent Application No. 2006-001917, Japanese Patent Application No. 2005-159926, Japanese Patent Application No. 2007-7028897, Japanese Patent Application No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Application No. 2005-111696, Japanese Patent Application No. Anions described in 2008-249663, Japanese Patent Publication No. 2014-199436 can be applied. Specific examples of the anionic group include trifluormethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluorethylsulfimide anion, tetraphenylborate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethane sulfonyl nilme suited _{^{to, SO 3 -, CO 2 -}} , SO 2 N - SO 2 CF 3, SO 2 N ^- SO ₂ CF ₂ CF _3, but include a halogen group such as fluorine group, an iodo group, a chlorine group, it is not limited thereto.

In the present specification, the anionic group may have an anion by itself, or may exist in the form of a complex with other cations. Therefore, the sum of the total charges of the compound molecules of the present invention may vary depending on the number of substituted anionic groups. Since the compound of the present invention has a cation in one amine group, the sum of the total charges of the molecule may have an anion to 0 as much as the number of substituted anionic groups minus one.

In this specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the nitrogen of the amide group may be substituted with hydrogen, a straight chain, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain or a branched chain, 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, the alkyl group may be a straight chain or a branched chain, and 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 are 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-ox Tilgi, and the like, but are 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 an exemplary 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, a 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 alkenyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 10 carbon atoms. As a specific example of the alkenyl group, an alkenyl group substituted with an aryl group such as a stylbenyl group or a styrenyl group is preferred, but is not limited thereto.

In the present specification, the cycloalkenyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary 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. Examples of the cycloalkenyl group include a cyclopentenylene group and a cyclohexenylene group, but are not limited to these.

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 one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylene group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the heterocyclic group is a heteroatom as a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but has 2 to 30 carbon atoms, and specifically 2 to 20 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol 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 Flags, etc., but are not limited to these.

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

In the present specification, the arylalkyl group means an alkyl group substituted with an aryl group, and the above description of the aryl group and the alkyl group may be applied to each.

In the present specification, the silyl group may be represented by the formula -SiY'Y''Y '' ', wherein Y', Y '' and Y '' 'are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. It is not limited to this.

In the present specification, the alkyl sulfoxy group includes methyl sulfoxy group, ethyl sulfoxyl group, propyl sulfoxyl group, butyl sulfoxyl group, but is not limited thereto. The alkyl group in the alkyl sulfoxy group can be applied to the description of the aforementioned alkyl group.

In the present specification, the aryl sulfoxy group includes benzene sulfoxy group, p-toluene sulfoxy group, and the like, but is not limited thereto. The aryl group in the aryl sulfoxy group may be applied to the aryl group described above.

In the present specification, the boron group may be represented by the formula -BY4Y5, wherein Y4 and Y5 are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. You can. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the ring refers to an aromatic, aliphatic or hetero ring in that adjacent groups may combine to form a “ring”. According to an example, the ring may be an aromatic or hetero ring, specifically, an aryl group or a heteroaryl group. The above description may be applied to the aryl group and heteroaryl group.

In the present specification, the alkylene group means that the alkane has two binding positions. The alkylene group may be straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, and more specifically 1 to 10 carbon atoms.

In the present specification, the acryloyl group means a photopolymerizable unsaturated group, and examples thereof include (meth) acryloyl group, but are not limited thereto.

In the present specification, the acrylate group means a photopolymerizable unsaturated group, for example, (meth) acrylate group, but is not limited thereto.

In the present specification, '(meth) acryloyl' refers to at least one selected from the group consisting of acryloyl and methacryloyl. The notation '(meth) acrylate' has the same meaning.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently an substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently 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, R1 and R2 are the same as or different from each other, and each independently 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, R1 and R2 are the same as or different from each other, and each independently 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, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently a methyl group; Or a phenyl group.

In one embodiment of the present specification, R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R3 to R8 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group of straight or branched chain.

In one embodiment of the present specification, R3 to R8 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 a straight chain or branched chain.

In one embodiment of the present specification, R3 to R8 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 a straight chain or branched chain.

In one embodiment of the present specification, R3 to R8 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 a straight chain or branched chain.

In one embodiment of the present specification, R3 to R8 are the same as or different from each other, and hydrogen; Or a substituted or unsubstituted tert-butyl group.

In one embodiment of the present specification, R3 to R6 are tert-butyl groups.

In one embodiment of the present specification, R7 and R8 are hydrogen.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group, or adjacent substituents combine with each other to form a ring, R 'is a substituted or unsubstituted aryl group, M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And a compound containing an ammonium structure, M1, M2 and Y are the same as or different from each other, and each independently substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or M1 and M2 combine with each other to form a ring.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or adjacent substituents combine with each other to form a ring, R 'is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And a compound containing an ammonium structure, M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or M1 and M2 combine with each other to form an aromatic or aliphatic ring.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or adjacent substituents combine with each other to form a ring, R 'is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And a compound containing an ammonium structure, M1, M2, and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or M1 and M2 combine with each other to form an aromatic or aliphatic ring.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or adjacent substituents combine with each other to form a ring, R 'is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And a compound containing an ammonium structure, M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted aryl group having 6 to 12 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, or M1 and M2 combine with each other to form an aromatic or aliphatic ring.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R9 to R13 are the same as or different from each other, and each independently hydrogen; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a methyl group.

In one embodiment of the present specification, R9 and R10 are hydrogen.

In one embodiment of the present specification, R11 is hydrogen; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; Or -SO ₂ NHY.

In one embodiment of the present specification, M is K ⁺ .

In one embodiment of the present specification, M1, M2, and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, M1, M2, and Y are the same as or different from each other, and each independently an substituted or unsubstituted ethyl group; Or a substituted or unsubstituted hexyl group.

In one embodiment of the present specification, M1, M2, and Y are the same as or different from each other, and each independently an ethyl group; Or a hexyl group substituted with an ethyl group.

In one embodiment of the present specification, M1 and M2 are ethyl groups.

In one embodiment of the present specification, Y is a hexyl group substituted with an ethyl group.

In one embodiment of the present specification, R12 is hydrogen; Or a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R12 is hydrogen; Or a methyl group.

In one embodiment of the present specification, R13 is hydrogen; SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R13 is hydrogen; SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R13 is hydrogen; SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a methyl group, the M is Na ⁺ or K ⁺ , and Y is a hexyl group substituted with an ethyl group.

In one embodiment of the present specification, the compound containing the ammonium structure may be a compound represented by the following Chemical Formula A or a unit represented by the following Chemical Formula B.

[Formula A]

[Formula B]

In Chemical Formula A,

Ra to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylalkyl group; -L-NHCO-Ri; Or -L-OCO-Ri, or two of Ra to Rd combine with each other to form a substituted or unsubstituted ring, wherein Ri is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group, the L is a substituted or unsubstituted alkylene group,

In the above formula B,

Rb to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, and Z is a substituted or unsubstituted alkylene group; A substituted or unsubstituted arylene group; -L-NHCO-; Or -L-OCO-, wherein L is a substituted or unsubstituted alkylene group, Re to Rg are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, in the formula A, Ra to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; -L-NHCO-Ri; Or -L-OCO-Ri, or two of Ra to Rd combine with each other to form a substituted or unsubstituted ring, wherein Ri is hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, and L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms,

In Formula B, Rb to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, and Z is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; -L-NHCO-; Or -L-OCO-, wherein L is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, Re to Rg 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.

According to an exemplary embodiment of the present specification, in the formula A, Ra to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms; -L-NHCO-Ri; Or -L-OCO-Ri, or two of Ra to Rd combine with each other to form a substituted or unsubstituted ring, wherein Ri is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms, and L is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms,

In Formula B, Rb to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, and Z is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; A substituted or unsubstituted arylene group having 6 to 20 carbon atoms; -L-NHCO-; Or -L-OCO-, wherein L is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, and Re to Rg 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 one embodiment of the present specification, X is an anionic group.

The anionic group is trifluormethanesulfonic acid anion, bis (trifluoromethylsulfonyl) imide anion, bistrifluormethanesulfimide anion, bisperfluoroethylsulfimide anion, tetraphenylborate anion, tetrakis ( 4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tristrifluoromethanesulfonyl methide and halogen group.

In one embodiment of the present specification, X may be a bistrifluormethanesulfonimide anion.

In one embodiment of the present specification, a is 0 or 1.

In one embodiment of the present specification, a is 0.

In one embodiment of the present specification, a is 1.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group.

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

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

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

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted ethylene group; Or a substituted or unsubstituted propylene group.

In one embodiment of the present specification, L1 to L4 are the same as or different from each other, and each independently a direct bond; Ethylene group; Or a propylene group.

In one embodiment of the present specification, L1 and L3 are the same as or different from each other, and each independently an ethylene group; Or a propylene group.

In one embodiment of the present specification, L2 and L4 are the same as or different from each other, and each independently a direct bond; Or an ethylene group.

In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently -O- or -NR-, and R is hydrogen; Or a substituted or unsubstituted alkylene group.

In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently -O- or -NR-, and R is hydrogen; Or a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently -O- or -NR-, and R is hydrogen; Or a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently -O- or -NR-, and R is hydrogen; Or a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently -O- or -NR-, and R is hydrogen.

In one embodiment of the present specification, X1 and X2 are -O-.

In one embodiment of the present specification, X1 and X2 are -NR-, and R is hydrogen.

In one embodiment of the present specification, r7 and r8 are integers from 0 to 2, and when r7 is 2, R7 is the same or different from each other, and when r8 is 2, R8 is the same or different from each other, and r9 and r10 are Is an integer from 0 to 3, when r9 is 2 or more, R9 is the same or different from each other, when R10 is 2 or more, R10 is the same or different from each other, r11 is an integer from 0 to 5, when r11 is 2 or more, R11 is R12 and r13 are the same or different from each other, and r12 is an integer of 0 to 4, and when r12 is 2 or more, R12 is the same or different from each other, and when r13 is 2 or more, R13 is the same or different from each other.

In an exemplary embodiment of the present specification, Formula 1 may be represented by the following structures, and the following structures represent isomers of Formula 1, and Formula 1 represents a representative structure. Isomer refers to molecules having the same molecular formula but different physical and chemical properties.

In the above structures, R1 to R13, X, a, L1 to L4, X1, X2, r7 to r13 are as defined in Chemical Formula 1.

The description of the isomers can be applied to all of the compounds described herein.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 2.

[Formula 2]

In Chemical Formula 2,

R1 to R13, X, a, L1 to L4, X1, X2, and r7 to r13 are as defined in Chemical Formula 1.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by Chemical Formula 3 below.

[Formula 3]

In Chemical Formula 3,

R1 to R10, R12, R13, X, a, L1 to L4, X1, X2, r7 to r10, r12 and r13 are as defined in Chemical Formula 1, Y is -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group, or adjacent substituents combine with each other to form a ring, R 'is a substituted or unsubstituted aryl group, M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And a compound containing an ammonium structure, M1, M2 and Y are the same as or different from each other, and each independently substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, M1 and M2 are bonded to each other to form a ring, R21 is hydrogen; Or deuterium, r21 is an integer from 0 to 4, and when r21 is 2 or more, R21 is the same as or different from each other.

In one embodiment of the present specification, R21 is hydrogen.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any of the following Chemical Formulas, but is not limited thereto.

In addition, an exemplary embodiment of the present specification provides a color material composition containing the compound.

One embodiment of the present specification provides a colorant composition further comprising at least one or more of dyes and pigments.

That is, the color material composition may further include at least one of dyes and pigments in addition to the compound of Formula 1 above. For example, the color material composition may include only the compound of Formula 1, but may include the compound of Formula 1 and one or more dyes, the compound of Formula 1 and one or more pigments, or the compound of Formula 1 , One or more dyes and one or more pigments.

In one embodiment of the present specification, the pigment and the dye are a metal prephthalocyanine pigment (dye), a metal phthalocyanine pigment (dye), a triarylmethane pigment (dye), xanthene pigment (dye), and azo pigment (Dye), metal azo pigment (dye), quinacridone pigment (dye), dioxazine pigment (dye), anthraquinone pigment (dye), quinophthalone pigment (dye), isoindoline pigment (dye) Dye), diketopyrrolopyrrole pigment (dye), (aza) porphyrin pigment (dye), cyanine pigment (dye), perylene pigment (dye), isoindolinone pigment (dye), perinone pigment (dye) Dyes), dianthraquinoline-based pigments (dyes) and one or more pigments (dyes) selected from the group consisting of anthrapyrimidine-based pigments (dyes).

The "pigment (dye)" means a pigment or dye.

One embodiment of the present specification provides a photosensitive resin composition comprising the color material composition.

According to an exemplary embodiment of the present specification, the photosensitive resin composition is a binder resin; Polyfunctional monomers; Photoinitiators; Additives and solvents.

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

Polyfunctional monomers that 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 ( Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydrofuryl (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 ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene 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 , Selected from the group consisting of 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, 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 include N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide. It can be, but is not limited to these.

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

The monomer that gives 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 It is preferable to use one or more, but is not limited to these.

In one embodiment of the present specification, the binder resin may be a copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30).

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

In one embodiment of the present specification, the acid value of the binder resin is 110 to 120 KOH mg / g, and the weight average molecular weight is 1,500 to 25,000.

In one embodiment of the present specification, the molecular weight distribution (PDI) of the binder resin may be 2.0.

The molecular weight distribution (PDI) is a polydispersity index (PDI), which is expressed by dividing the weight average molecular weight value by the number average molecular weight.

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

In one embodiment of the present specification, the weight average molecular weight may be measured by gel permeation chromatography (GPC), but is not limited thereto.

The polyfunctional monomer is a monomer that serves to form a photoresist phase by light, 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.

In an exemplary embodiment of the present specification, the multifunctional monomer may be dipentaerythritol hexa acrylate (DPHA).

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

The acetophenone-based compounds are 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, benzoinmethyl ether, benzoinethyl ether, benzoinisobutyl 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.

The biimidazole-based compound is 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. , But is not limited to this.

The triazine-based 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-di Methylaminophenyl) -1,3, -butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like. .

The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai, Shijii124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CG 242), N-1919 (Adeka), and the like.

In one embodiment of the present specification, the photoinitiator may be I-369 (BASF).

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 monomethyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxy part It may be one or more selected from the group consisting of acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but only It is not limited.

In one embodiment of the present specification, the solvent may be propylene glycol monomethyl ether acetate (PGMEA).

In one embodiment of the present specification, the content of the compound represented by Chemical Formula 1 based on the total weight of the photosensitive resin composition is 5% to 60% by weight, and the content of the binder resin is 1% to 60% by weight, The content of the photoinitiator is 0.1% to 20% by weight, the content of the multifunctional monomer is 0.1% to 50% by weight, the content of the additive is 0.1% to 10% by weight, and the content of the solvent is 10 It provides a photosensitive resin composition that is from 80% to 80% by weight.

Further, according to an exemplary embodiment of the present specification, based on the total weight of the solid content in the photosensitive resin composition, the content of the compound represented by Formula 1 is 5% to 60% by weight, the content of the binder resin is 1 Weight% to 60% by weight, the content of the photoinitiator is 0.1% to 20% by weight, the content of the multifunctional monomer is 0.1% to 50% by weight, the content of the additive is 0.1% to 10% by weight to be.

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

According to one embodiment of the present specification, the photosensitive resin composition is a photocrosslinker, a curing accelerator, an adhesion promoter, an antioxidant, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent selected from the group consisting of 1 or 2 The above additives are included.

According to an exemplary embodiment of the present specification, the photosensitive resin composition may include a surfactant.

According to an exemplary embodiment of the present specification, the content of the surfactant is 0.1% to 10% by weight based on the total weight of the photosensitive resin composition.

According to an exemplary embodiment of the present specification, the content of the surfactant is 0.1% to 10% by weight based on the total weight of solids in the photosensitive resin composition.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant, and specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-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. DIC is a fluorine-based surfactant. (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.

In one embodiment of the present specification, the surfactant may be F-475 of DIC Corporation.

The photocrosslinking agent 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; Florenone-based compounds, such as 9-Florenone, 2-Croro-9-Prorenone, and 2-methyl-9-Florenone; Thioxanthone series 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 compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptan-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-based compounds such as pyrano [6,7,8-ij] -quinolinazine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azide benzal acetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of;

The curing accelerator is used to increase 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.

Examples of the adhesion promoter include metaacrylic such as methacryloyloxy propyl trimethoxy silane, methacryloyloxy propyl dimethoxy silane, methacryloyloxy propyl triethoxy silane, and methacryloyloxy propyl dimethoxysilane. One or more of the silane silane coupling agents can be selected and used. As the alkyl trimethoxy silane, one or more of octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane can be used. have.

The antioxidant may be at least one 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-based thermal stabilizers such as phosphoric acid, trimethylphosphate or triethylphosphate; 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 esters such as hindered phenol primary antioxidants; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine Secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuramdisulfide tetrabis [methylene-3- (laurylthio) propionate] methane 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 ' And 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, and in the art Anything commonly used 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- Methylene bis (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 is not limited to sugar technology These may include those commonly known in the art.

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

Specifically, the dispersant is polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonic acid salts, carboxylic acid esters, carboxylic acid salts, There is 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 the polymeric leveling agent include polyethyleneimine, polyamideamine, amine and epoxide reaction products, and specific examples of the non-polymeric leveling agent include non-polymeric sulfur-containing and non-polymeric nitrogen-containing Compounds include, but are not limited to, all those commonly used in the art may be used.

According to an exemplary embodiment of the present specification, to provide a photosensitive material prepared using the photosensitive resin composition.

In more detail, the photosensitive resin composition of the present specification is coated on a substrate by an appropriate method and cured to form a thin film or patterned photosensitive material.

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

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

The photosensitive resin composition according to the present specification is a thin film transistor type liquid crystal display (TFT LCD) pigment dispersion type photosensitive material for manufacturing a color filter, a thin film transistor liquid crystal display device (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode , Can be used for photoresist for overcoat layer formation, column spacer photoresist, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photosensitive material for printed wiring board, photosensitive material for plasma display panel (PDP), etc. There are no restrictions.

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

The color filter may be manufactured by using the photosensitive resin composition containing the compound represented by Chemical Formula 1. 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 has an advantage of being excellent in heat resistance and excellent in transmittance, thereby improving luminance.

The substrate may be a glass plate, a silicon wafer, and a plastic-based plate such as polyethersulfone (PES) or polycarbonate (PC), and the type 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 grid called a black matrix can be arranged between color pixels of a color filter for the purpose of improving 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 may be used. However, considering the high cost of the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, it is possible to use a resin black matrix by a pigment dispersion method capable of fine processing.

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

It provides a display device including a 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), a thin film transistor It may be any one of a liquid crystal display (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (CRT).

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other 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 fully describe the present specification to those skilled in the art.

<Example>

<Synthesis Examples of Colorant Compound>

Synthesis Example 1: Synthesis of Compound 1

Intermediate 1 (1.40g, 2.0mmol) was dissolved in Chloroform (40ml), and triethylamine (1.02g, 10mmol) was slowly added dropwise. After reaction at room temperature (25 ° C), the reaction solution was quenched with H ₂ O. After separating the organic layer and treating with MgSO ₄ , the solvent was removed under reduced pressure. Compound 1 was obtained through column chromatography.

Ionization mode =: APCI +: m / z = 1163 [M + H] +, Exact Mass: 1162

Synthesis Example 2: Synthesis of Compound 2

In Synthesis Example 1, Compound 2 was obtained by the same method as Synthesis Example 1, except that Intermediate B was used instead of Intermediate A.

Ionization mode =: APCI +: m / z = 1219 [M + H] +, Exact Mass: 1218

Synthesis Example 3: Synthesis of Compound 3

In Synthesis Example 1, except for using Intermediate 2 instead of Intermediate 1 was prepared in the same manner as in Synthesis Example 1 to obtain compound 3.

Ionization mode =: APCI +: m / z = 1191 [M + H] +, Exact Mass: 1190

Synthesis Example 4: Synthesis of Compound 4

In Synthesis Example 2, Compound 4 was obtained by the same method as Synthesis Example 2, except that Intermediate 2 was used instead of Intermediate 1.

Ionization mode =: APCI +: m / z = 1247 [M + H] +, Exact Mass: 1246

Synthesis Example 5: Synthesis of Compound 5

In Synthesis Example 1, except for using Intermediate 3 instead of Intermediate 1 was prepared in the same manner as in Synthesis Example 1 to obtain compound 5.

Ionization mode =: APCI +: m / z = 1161 [M + H] +, Exact Mass: 1160

Synthesis Example 6: Synthesis of Compound 6

In Synthesis Example 2, it was prepared in the same manner as in Synthesis Example 2, except that Intermediate 3 was used instead of Intermediate 1, to obtain Compound 6.

Ionization mode =: APCI +: m / z = 1217 [M + H] +, Exact Mass: 1216

Synthesis Example 7: Synthesis of Compound 7

In Synthesis Example 1, except for using Intermediate 4 instead of Intermediate 1 was prepared in the same manner as in Synthesis Example 1 to obtain compound 7.

Ionization mode =: APCI +: m / z = 1189 [M + H] +, Exact Mass: 1188

Synthesis Example 8: Synthesis of Compound 8

In Synthesis Example 2, it was prepared in the same manner as in Synthesis Example 2, except that Intermediate 4 was used instead of Intermediate 1, to obtain Compound 8.

Ionization mode =: APCI +: m / z = 1245 [M + H] +, Exact Mass: 1244

Comparative compound 1

Comparative compound 2

Comparative compound 3

The comparative compound 1 is Basic blue7, Comparative compound 2 is Rhodamine 6G, Comparative compound 3 is Rhodamine B, and all are from TCI.

Example.

A photosensitive resin composition was prepared in the ratio shown in Table 1 below. The dosage unit of the compound listed in Table 1 is grams (g).

Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Comparative Example 1 Comparative Example 2 Comparative Example 3 Compound 1 5.554 - - - - - - - - - - Compound 2 - 5.554 - - - - - - - - - Compound 3 - - 5.554 - - - - - - - - Compound 4 - - - 5.554 - - - - - - - Compound 5 - - - - 5.554 - - - - - - Compound 6 - - - - - 5.554 - - - - - Compound 7 - - - - - - 5.554 - - - - Compound 8 - - - - - - - 5.554 - - - Comparative compound 1 - - - - - - - - 5.554 - - Comparative compound 2 - - - - - - - - - 5.554 - Comparative compound 3 - - - - - - - - - - 5.554 Binder resin (g) 10.376 Photoinitiator (g) 2.018 Additive (g) 1.016 Polyfunctional monomer (g) 12.443 Solvent (g) 68.593 Total content (g) 100 Binder Resin: Copolymer of benzyl methacrylate and methacrylic acid (molar ratio 70:30, acid value 113
KOH mg / g, weight average molecular weight 20,000 as measured by GPC, molecular weight distribution (PDI) 2.0,
25% solids (SC), including solvent PGMEA)
Photoinitiator: I-369 (BASF)
Multifunctional monomer: DPHA (Japanese Chemicals)
Solvent: PGMEA (Propylene Glycol Mnomethyl Ether Acetate)
Additive: DIC company F-475
* Evaluation after filtering of insoluble ingredients

Substrate production

The compound prepared by the above synthesis was spin coated on glass (5 cm × 5 cm) and subjected to prebake at 100 ° C. for 100 seconds to form a film. The distance between the substrate on which the film was formed and the photomask was set to 250 µm, and an exposure dose of 40 mJ / cm ² was investigated on the entire surface of the substrate using an exposure machine.

Thereafter, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-baked at 230 ° C for 20 minutes to produce a substrate.

Heat resistance evaluation

The prepared pre-heat treatment (prebake) substrate using a spectrometer (MCPD-Otsuka Co.) to obtain a transmittance spectrum of the visible light region in the range of 380nm to 780nm. In addition, a prebake substrate was additionally subjected to post bake at 230 ° C for 20 minutes to obtain a transmittance spectrum in the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, ΔEab was calculated using the obtained values E (L *, a *, b *) and shown in Table 2 below.

ΔEab (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2

△ Small Eab value means excellent color heat resistance.

The results of the heat resistance evaluation of the substrates prepared by Examples 1 to 8 and the substrates produced by Comparative Examples 1 and 3 are shown in Table 2 below. As shown in Table 2 below, it was confirmed that the substrates prepared by Examples 1 to 8 had small color change (ΔEab) compared to Comparative Examples 1 to 3.

△ Eab (PB-PrB) Example 1 1.24 Example 2 1.34 Example 3 1.38 Example 4 1.51 Example 5 0.97 Example 6 1.12 Example 7 1.04 Example 8 1.37 Comparative Example 1 27.48 Comparative Example 2 24.54 Comparative Example 3 19.20

Contrast ratio measurement

Using the contrast ratio measuring device (CT-1, ZOENTECH), the substrate produced according to the above substrate manufacturing method is used to put the produced substrate between the two polarizing plates and the luminance when the two polarizing plates are horizontal and the two polarizing plates. The brightness at this orthogonality was measured, and the contrast ratio was calculated by the following equation 1.

[Calculation formula 1]

Contrast Ratio = Luminance when two polarizers are horizontal / Luminance when two polarizers are vertical

The contrast ratio calculated by the above calculation formula 1 was calculated using the following calculation formula 2 to calculate the contrast ratio, and the results are shown in Table 3 below.

[Calculation formula 2]

Contrast Ratio Improvement Rate = {(Example Contrast Ratio-Comparative Example 3 Contrast Ratio) / Comparative Example 3} * 100

Contrast ratio improvement rate (%) Comparative Example 3 Example 1 314 Example 2 345 Example 3 280 Example 4 294 Example 5 480 Example 6 497 Example 7 455 Example 8 467

According to Table 3, it was confirmed that the contrast ratio of Examples 1 to 8 was improved by 280 to 497% compared to Comparative Example 3.

Claims (12)

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

In Chemical Formula 1,
R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R3 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group,
R9 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxy group; -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group, or adjacent substituents combine with each other to form a ring,
R 'is a substituted or unsubstituted aryl group,
M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure,
M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or M1 and M2 combine with each other to form a ring,
X is an anionic group,
a is 0 or 1,
L1 to L4 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted alkylene group,
X1 and X2 are the same as or different from each other, and each independently -O- or -NR-,
R is hydrogen; Or a substituted or unsubstituted alkylene group,
r7 and r8 are integers from 0 to 2, when r7 is 2, R7 is the same or different from each other, and when r8 is 2, R8 is the same or different from each other,
r9 and r10 are integers from 0 to 3, when r9 is 2 or more, R9 is the same or different from each other, and when R10 is 2 or more, R10 is the same or different from each other,
r11 is an integer from 0 to 5, and when r11 is 2 or more, R11 is the same as or different from each other,
r12 and r13 are integers from 0 to 4, and when r12 is 2 or more, R12 is the same or different from each other, and when r13 is 2 or more, R13 is the same or different from each other. The method according to claim 1, wherein Formula 1 is a compound represented by Formula 2:
[Formula 2]

In Chemical Formula 2,
R1 to R13, X, a, L1 to L4, X1, X2, and r7 to r13 are as defined in Chemical Formula 1. The method according to claim 1, wherein Formula 1 is a compound represented by Formula 3:
[Formula 3]

In Chemical Formula 3,
R1 to R10, R12, R13, X, a, L1 to L4, X1, X2, r7 to r10, r12 and r13 are as defined in Chemical Formula 1,
Y is -COOH; -COR '; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; Or a substituted or unsubstituted alkyl group, or adjacent substituents combine with each other to form a ring,
R 'is a substituted or unsubstituted aryl group,
M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure,
M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or M1 and M2 combine with each other to form a ring,
R21 is hydrogen; Or deuterium,
r21 is an integer from 0 to 4, and when r21 is 2 or more, R21 is the same as or different from each other. The method according to claim 1,
R3 to R6 are substituted or unsubstituted tert-butyl compounds. The method according to claim 1, wherein the compound represented by Formula 1 is a compound represented by any one of the following formula:

A color material composition comprising the compound according to claim 1. The method according to claim 6, Color material composition further comprising at least one or more of dyes and pigments. A compound according to claim 1; Binder resin; Polyfunctional monomers; Photoinitiators; Photosensitive resin composition comprising an additive and a solvent. The method according to claim 8, The content of the compound represented by Formula 1 based on the total weight of the photosensitive resin composition is 5% to 60% by weight,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1% to 20% by weight,
The content of the polyfunctional monomer is 0.1% to 50% by weight,
The content of the additive is 0.1% to 10% by weight,
The content of the solvent is 10 to 80% by weight of the photosensitive resin composition. A photosensitive material prepared using the photosensitive resin composition according to claim 8. A color filter comprising the photosensitive material according to claim 10. Display device comprising a color filter according to claim 11.