TW201936601A - Xanthene-based compound, colorant composition, photosensitive resin composition, photosensitive material, color filter and display device - Google Patents

Abstract

The invention provides a compound represented by chemical formula 1, a colorant composition including the same, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.

Description

Dibenzopyran-based compound, colorant composition, photo-sensitive resin composition, photoresist, color filter, and display device

The present application claims the benefit of the filing date of the Korean Patent Application No. 10-2018-0022076 filed on Jan. 23, 2018, to the Korean Patent Office, the entire contents of which is incorporated herein.
The present application claims the benefit of the filing date of the Korean Patent Application No. 10-2019-0001820 filed on Jan. 7, 2019 to the Korean Patent Office, the entire contents of which is incorporated herein.
The present specification relates to a dibenzopipen-based compound and a coloring agent composition and a photosensitive resin composition containing the dibenzopyran-based compound. Further, the present specification relates to a photosensitive material produced by using the photosensitive resin composition, a color filter, and a display device including the color filter.

Recently, for color filters, performance characterized by high brightness and high contrast ratio is required. In addition, one of the main purposes of the development of display elements is the differentiation of display element performance and the improvement of productivity in manufacturing steps due to the improvement in color purity.

Previously, the type of pigment used as a coloring agent of a color filter is present in a color dispersion in a particle-dispersed state, and therefore, it is difficult to adjust the brightness and the contrast ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, aggregation occurs in a color filter, dissolution and dispersibility are lowered, and multiple scattering of light is caused by aggregation of large particles. The scattering of such polarized light is a major cause of the decrease in the contrast ratio. In order to increase the brightness and the contrast ratio by ultrafine particle formation and dispersion stabilization of the pigment, efforts are being made continually, but the degree of freedom is limited in the selection of the coloring material for realizing the color coordinates of the high color purity display device. . In addition, pigment dispersion methods using developed color former materials, particularly pigments, have reached the limit in terms of improving the color purity, brightness, and contrast ratio of color filters using the same.

Accordingly, it is required to develop novel colorants that can improve color purity to enhance color reproduction, brightness, and contrast ratio.

[Problems to be solved by the invention]
The inventors of the present invention provide a dibenzopipelanic compound, a coloring matter composition including the same, a photosensitive resin composition, a photosensitive material produced by using the photosensitive resin composition, a color filter, and a containing device. A display device for a color filter.

[Means for solving the problem]
One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.
[Chemical Formula 1]

In the chemical formula 1,
R ₁ to R ₆ are the same or different from each other, and are independently selected from hydrogen, dihydrogen, halogen, nitro, substituted or unsubstituted, linear or branched alkyl having 1 to 30 carbon atoms, substituted. Or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted carbon number 2 to 30 a group consisting of monocyclic or polycyclic heteroaryl groups;
R ₇ to R ₁₁ are the same or different from each other, and are independently selected from hydrogen, heavy hydrogen, -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ Ra, -SO ₂ NRbRc, -SO ₂ NHRd, -COOH. , -COORa, -CONRd, substituted or unsubstituted alkyl or linear alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms or monocyclic or polycyclic And a substituted or unsubstituted group of 2 to 30 monocyclic or polycyclic heteroaryl groups;
Ra to Rd are the same or different from each other, and are independently selected from a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms. Or a polycyclic aryl group, and a substituted or unsubstituted group of 2 to 30 carbon monocyclic or polycyclic heteroaryl groups;
R _{12 is} selected from hydrogen, dihydrogen, substituted or unsubstituted, straight or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted, monocyclic or polycyclic having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and a dianhydride group containing a nitrogen atom;
R _{1 3} and R ₁₄ are each independently a substituted or unsubstituted, straight or branched alkyl group having 1 to 30 carbon atoms;
R ₁₅ and R ₁₆ are the same or different from each other, and are each independently selected from hydrogen, dihydrogen, -OH, substituted or unsubstituted, linear or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted. a substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms of a monocyclic or polycyclic group, or a mutual bond Forming a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms;
L ₁ and L ₂ are the same or different from each other, and are each independently selected from a linear or branched alkyl group having 2 to 30 carbon atoms which are directly bonded, substituted or unsubstituted, -L ₃ -OL ₄ -, _{-L 3 -SL 4 -, - L} 3 -NH-L 4 -, - L 3 -CO-L 4 -, - L 3 -COO-L 4 -, - L 3 -OCO-L 4 -, - L a group consisting of ₃ -NHCO-L ₄ - and -L ₃ -CONH-L ₄ -;
L ₃ and L ₄ are the same or different from each other, and are a substituted or unsubstituted alkyl or a branched alkyl group having 1 to 30 carbon atoms;
a is an integer of 0 or 1;
X is an anionic group.

One embodiment of the present specification provides a color former composition comprising the compound represented by Chemical Formula 1.

One embodiment of the present specification provides a photosensitive resin composition comprising the compound represented by Chemical Formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

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

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

An embodiment of the present specification provides a display device including the color filter.
[Effects of the Invention]

The dibenzopipelan compound of one embodiment of the present specification can be used as a coloring agent in a photosensitive resin composition, and can be used as a color spectrum filter from a light source as compared with the prior coloring agent. The absorption and transmission spectra are adjusted to improve color purity.

Further, the dibenzopipelan compound of one embodiment of the present specification can be used as a colorant material, and the reproduction, brightness, and contrast ratio can be improved.

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

In the present specification, when a component is "included" in a certain part, unless otherwise stated, the case means that other components may be included, and other components are not excluded.

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

In the chemical formula 1, when an alkyl phthalimide is substituted on a nitrogen atom, the dispersibility of the pigment can be improved, and the crystal transition of the pigment at a high temperature can be suppressed to stabilize the pigment at a high temperature. Thereby, the dispersibility and storage stability can be improved and the color change can be reduced by stabilizing the pigment.

Further, when R _{1 3} and R ₁₄ are an alkyl group, the maximum absorption wavelength (λmax) of the photosensitive material containing the compound of the chemical formula 1 exists in a region of 550 nm to 580 nm, and has a transmittance of 600 nm or more. Excellent and easy to realize the color of the red wavelength region.

The exemplification of the substituent of the compound represented by Chemical Formula 1 will be described below, but is not limited thereto.

In the present specification, the term "substituted or unsubstituted" means selected from the group consisting of heavy hydrogen, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, nonylalkyl, aryl, alkyl. Sulfonic acid oxy group, aryl sulfonic acid oxy group, boron group, alkyl amine group, aryl amine group, heteroaryl group, ether group, nitrile group, nitro group, hydroxyl group (-OH), carboxyl group (-COOH), One or more of -SO ₃ ^- , a sulfonic acid group, a sulfonate group, a sulfonate group, or a group containing one or more heterocyclic groups and an anionic group of an N atom, an O atom, an S atom or a P atom The substituent is substituted or does not have any substituent.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, and is preferably from 1 to 30. Specifically, it may be 1 to 20 or 1 to 10. Specific examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a hexyl group, and a heptyl group, but are not limited thereto.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, and is preferably 2 to 30. Specifically, it may be 2 to 20 or 2 to 10. The specific example is preferably an alkenyl group substituted with an aryl group such as a stylbenyl group or a styrenyl group, 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, and is preferably from 1 to 30. Specifically, it may be 1 to 20 or 1 to 10.

In the present specification, the cycloalkyl group is not particularly limited, and is preferably a carbon number of from 3 to 30, particularly preferably a cyclopentyl group or a cyclohexyl group. Specifically, it may be 3 to 20 or 3 to 10.

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

In the present specification, the sulfonic acid group may be represented by -SO ₃ H.

In the present specification, the sulfonate group is a salt with a monovalent cation, and the monovalent cation may be any one selected from the group consisting of Na ⁺ , K ⁺ and quaternary ammonium cations, but is not limited thereto. herein. Specific examples of the quaternary ammonium cation may be a tetraalkylammonium cation such as a tetramethylammonium cation, an ethyltrimethylammonium cation or a tetrapropylammonium cation, but are not limited thereto.

In the present specification, specific examples of the sulfonate group include alkylsulfonyl groups having 1 to 4 carbon atoms such as a methylsulfonyl group, an ethylsulfonyl group, and a hexylsulfonyl group, but are not limited thereto.

In the present specification, the sulfonylamino group may be expressed as -SO ₂ NRxRy, for example, Rx and Ry are the same or different from each other, and are independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms. A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

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

In the case where the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, and is preferably from 6 to 30 carbon atoms. Specifically, the carbon number may be 6 to 20 or 6 to 12. For example, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

In the case where the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, an anthracenyl group, a fluorenyl group, a fluorenyl group, a fluorenyl group or 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 carbon atoms is not particularly limited, and is preferably 2 to 30 carbon atoms. Examples of heterocyclic groups are: thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl, Pyridazinyl, quinolyl, isoquinolyl, fluorenyl, oxazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, benzothienyl, diphenyl And thiophenyl, benzofuranyl, dibenzofuranyl, etc., but not limited to these.

In the present specification, the description relating to the heterocyclic group may be applied to the heteroaryl group in addition to the aromatic group. The carbon number of the heteroaryl group is not particularly limited and may be 2 to 30. Specifically, it may be 2 to 20, and may be 2 to 10 in another embodiment.

In the present specification, alkylene refers to a position having two bonding sites on an alkane. The alkylene group may be a straight chain, a branched chain or a cyclic chain. The carbon number of the alkylene group is not particularly limited, and is, for example, 1 to 30 carbon atoms. Specifically, it may have a carbon number of 1 to 20, and in another embodiment, it may have a carbon number of 1 to 10.

In the present specification, an alkenyl group means a group having two bonding sites on an alkene. The alkenyl group may be a straight chain, a branched chain or a cyclic chain. The carbon number of the alkenyl group is not particularly limited, and is, for example, 2 to 30 carbon atoms. Specifically, it may be 2 to 20, and more specifically 2 to 10.

In the present specification, the anionic group has a chemical bond with the structure of the chemical formula 1, and the anionic group is not particularly limited, and for example, US Patent No. 7,939,644, Japanese Patent Laid-Open No. 2006-003080, and Japanese Patent Laid-Open No. 2006 -001917, Japanese Patent Laid-Open No. 2005-159926, Japanese Patent Laid-Open No. 2007-7028897, Japanese Patent Laid-Open No. 2005-071680, Korean Application Publication No. 2007-7000693, Japanese Patent Laid-Open No. 2005- An anion described in No. 111696, Japanese Patent Laid-Open No. 2008-249663, and Japanese Patent Laid-Open No. 2014-199436. Specific examples of the anionic group include an anion containing a compound selected from the group consisting of tungsten, molybdenum, rhenium, and phosphorus and oxygen, a trifluoromethanesulfonate anion, and a bis(trifluoromethyl group). Sulfhydryl)guanamine anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis(4-fluorophenyl)borate, tetrakis(pentafluoro Phenyl)borate, tris-trifluoromethanesulfonylmethylate, -SO ₃ ^- , -CO ₂ ^- , -SO ₂ N ^- SO ₂ CF ₃ , -SO ₂ N ^- SO ₂ CF ₂ CF ₃ , The halogen group is, for example, a fluorine group, an iodine group, a chlorine group or the like, but is not limited thereto.

In the present specification, the anionic group may have an anion itself, or may exist in the form of a wrong compound together with other cations. Therefore, the total charge of the entire molecule of the compound of the present invention can be changed depending on the number of substituted anionic groups. Since one amine group of the compound of the present invention has a cation, the total of the charges of the entire molecule may have a value from the anion to 0 corresponding to the value obtained by subtracting 1 from the number of substituted anionic groups.

According to the embodiment described above, in the chemical formula 1, the R ₁ to R ₆ may be the same or different from each other, and are each independently selected from hydrogen, dihydrogen, halogen, nitro, substituted or unsubstituted. a linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted single or multiple ring having 6 to 30 carbon atoms a aryl group of a ring, and a substituted or unsubstituted group of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to another embodiment of the present specification, the R ₁ to R ₆ may be the same or different from each other, and are independently selected from the group consisting of hydrogen, heavy hydrogen, halogen, nitro, substituted or unsubstituted carbon number 1 to a linear or branched alkyl group of 20, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic group; And a substituted or unsubstituted group of 2 to 20 carbon monocyclic or polycyclic heteroaryl groups.

According to still another embodiment of the present specification, the R ₁ to R ₆ may be the same or different from each other, and are independently selected from the group consisting of hydrogen, heavy hydrogen, halogen, nitro, substituted or unsubstituted carbon number 1 to a linear or branched alkyl group of 10, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms, And a substituted or unsubstituted group of 2 to 10 carbon monocyclic or polycyclic heteroaryl groups.

According to still another embodiment of the present specification, the R ₁ to R ₆ may be the same or different from each other, and each independently is hydrogen, a halogen group, or a substituted or unsubstituted linear or branched carbon number of 1 to 10. The alkyl group of the chain.

According to still another embodiment of the present specification, the R ₁ to R ₆ may be the same or different from each other, and are each independently hydrogen, a halogen group, or a substituted or unsubstituted methyl group.

According to still another embodiment of the present specification, the R ₁ to R ₆ may be the same or different from each other, and are each independently hydrogen, a halogen group, or a methyl group.

According to still another embodiment of the present specification, the R ₁ to R ₆ may be the same or different from each other, and are each independently hydrogen, fluorine, or a methyl group.

According to still another embodiment of the present specification, the R ₁ to R ₆ may be hydrogen.

According to another embodiment of the present specification, R ₁ and R _{4 may} be halogen or methyl, and R ₂ , R ₃ , R ₅ or R _{6 may} be hydrogen.

According to still another embodiment of the present specification, R ₁ and R _{4 may} be fluorine or methyl, and R ₂ , R ₃ , R ₅ or R _{6 may} be hydrogen.

Further, R ₇ to R ₁₁ are the same or different from each other, and are each independently selected from the group consisting of hydrogen, heavy hydrogen, -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ Ra, -SO ₂ NRbRc, -SO ₂ NHRd, -COOH, -COORa, -CONRd, substituted or unsubstituted alkyl or linear alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic ring having 6 to 30 carbon atoms An aryl group, and a substituted or unsubstituted group of 2 to 30 carbon monocyclic or polycyclic heteroaryl groups;
Ra to Rd are the same or different from each other, and are independently selected from a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms. Or a polycyclic aryl group, and a substituted or unsubstituted group of 2 to 30 carbon monocyclic or polycyclic heteroaryl groups.

According to another embodiment of the present specification, the R ₇ to R ₁₁ are the same or different from each other, and are independently selected from the group consisting of hydrogen, heavy hydrogen, -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ Ra, -SO ₂ NRbRc, -SO ₂ NHRd, -COOH, -COORa, -CONRd, substituted or unsubstituted, linear or branched alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted carbon number a monocyclic or polycyclic aryl group of 6 to 20, and a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms of a monocyclic or polycyclic group;
Ra to Rd are the same or different from each other, and are independently selected from a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted monocyclic ring having 6 to 20 carbon atoms. Or a polycyclic aryl group, and a substituted or unsubstituted group of 2 to 20 carbon monocyclic or polycyclic heteroaryl groups.

According to still another embodiment of the present specification, the R ₇ to R ₁₁ are the same or different from each other, and are independently selected from the group consisting of hydrogen, heavy hydrogen, -OH, -SO ₃ ^- , -SO ₃ H, -SO ₃ Ra, -SO ₂ NRbRc, -SO ₂ NHRd, -COOH, -COORa, -CONRd, substituted or unsubstituted alkyl or linear alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted carbon number a group of 6 to 12 monocyclic or polycyclic aryl groups, and a substituted or unsubstituted heterocyclic aryl group having 2 to 10 carbon atoms;
Ra to Rd are the same or different from each other, and are independently selected from a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted monocyclic ring having 6 to 12 carbon atoms. Or a polycyclic aryl group, and a substituted or unsubstituted group of 2 to 10 carbon monocyclic or polycyclic heteroaryl groups.

According to still another embodiment of the present specification, the R ₇ to R ₁₁ may be the same or different from each other, and are each independently hydrogen, -SO ₃ ^- , -SO ₃ H or -SO ₂ NHRd, and the Rd may be a A substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

According to an embodiment of the present specification, the R ₇ to R ₁₁ may be the same or different from each other, and are independently hydrogen, -SO ₃ ^- , -SO ₃ H or -SO ₂ NHRd, and the Rd may be substituted. Or unsubstituted propyl, substituted or unsubstituted butyl, substituted or unsubstituted pentyl, substituted or unsubstituted hexyl, or substituted or unsubstituted heptyl.

According to an embodiment of the present specification, the R ₇ to R ₁₁ may be the same or different from each other, and are independently hydrogen, -SO ₃ ^- , -SO ₃ H or -SO ₂ NHRd, and the Rd may be substituted. Or unsubstituted propyl, or substituted or unsubstituted hexyl.

According to an embodiment of the present specification, the R ₇ to R ₁₁ may be the same or different from each other, and are independently hydrogen, -SO ₃ ^- , -SO ₃ H or -SO ₂ NHRd, and the Rd may be B. A substituted hexyl group or a propyl group substituted or unsubstituted with an ethyl group.

Further, R ₁₂ may be optionally hydrogen, dihydrogen, substituted or unsubstituted, straight or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted monocyclic ring having 6 to 30 carbon atoms or A polycyclic aryl group, a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, and a dianhydride group containing a nitrogen atom.

According to another embodiment of the present specification, R ₁₂ may be optionally hydrogen, dihydrogen, substituted or unsubstituted, linear or branched alkyl having 1 to 20 carbon atoms, substituted or unsubstituted carbon. a group of 6 to 20 monocyclic or polycyclic aryl groups, substituted or unsubstituted heterocyclic aryl groups having 2 to 20 carbon atoms, and dianhydride groups containing a nitrogen atom; in.

According to still another embodiment of the present specification, R ₁₂ may be optionally hydrogen, dihydrogen, substituted or unsubstituted, linear or branched alkyl having 1 to 10 carbon atoms, substituted or unsubstituted carbon. a group consisting of 6 to 12 monocyclic or polycyclic aryl groups, substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 10 carbon atoms, and dianhydride groups containing a nitrogen atom in.

According to still another embodiment of the present specification, R ₁₂ may be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a branched or branched chain, or a dianhydride group containing a nitrogen atom.

According to still another embodiment of the present specification, R ₁₂ may be substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted Isopropyl, substituted or unsubstituted isobutyl, or dianhydride containing a nitrogen atom.

According to still another embodiment of the present specification, R ₁₂ may be a methyl group, an ethyl group, a propyl group, an isopropyl group, an isobutyl group, or a dianhydride group containing a nitrogen atom.

Further, R ₁₃ and R ₁₄ may be the same or different from each other, and each independently is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms.

When R ₁₃ and R ₁₄ are the same or different from each other and independently have a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in a straight or branched chain, light of a red wavelength region can be emitted when utilized When a color filter comprising a compound represented by the structure of the chemical formula 1 is produced to produce a color filter, a desired color can be selectively achieved.

Specifically, when R _{1 3} and R ₁₄ are an alkyl group, the maximum absorption wavelength (λmax) of the photosensitive material containing the compound of Chemical Formula 1 exists in a region of 550 nm to 580 nm, and is transmitted through 600 nm or more. The color is excellent and the color of the red wavelength region is easily realized.

According to another embodiment of the present specification, R ₁₃ and R ₁₄ may be the same or different from each other, and are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms in a straight or branched chain.

According to still another embodiment of the present specification, R ₁₃ and R ₁₄ may be the same or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms in a straight or branched chain.

According to still another embodiment of the present specification, R ₁₃ and R ₁₄ may be the same or different from each other, and are each independently a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, substituted or unsubstituted. Substituted propyl, or substituted or unsubstituted isopropyl.

According to still another embodiment of the present specification, R ₁₃ and R ₁₄ may be the same or different from each other, and are each independently a methyl group, an ethyl group, an ethyl group substituted by -OH, a propyl group, or an isopropyl group.

Further, R ₁₅ and R ₁₆ may be the same or different from each other, and are each independently selected from a hydrogen group, a hydrogen group, a -OH group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted chain. Or an unsubstituted group of 6 to 30 monocyclic or polycyclic aryl groups, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms or a polycyclic heteroaryl group, Or mutually bonded to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic ring having 2 to 30 carbon atoms; Heterocyclic.

According to another embodiment of the present specification, R ₁₅ and R ₁₆ may be the same or different from each other, and are independently selected from the group consisting of hydrogen, heavy hydrogen, -OH, substituted or unsubstituted straight chain having 1 to 20 carbon atoms or a branched chain alkyl group, a substituted or unsubstituted hexacyclic or polycyclic aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heterocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms a group consisting of groups or bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a substituted or unsubstituted carbon number 2 to 20 monocyclic or polycyclic heterocycles.

According to still another embodiment of the present specification, R ₁₅ and R ₁₆ may be the same or different from each other, and are independently selected from the group consisting of hydrogen, heavy hydrogen, -OH, substituted or unsubstituted straight chain having a carbon number of 1 to 10 or a branched chain alkyl group, a substituted or unsubstituted hexacyclic or polycyclic aryl group having 6 to 12 carbon atoms, and a substituted or unsubstituted heterocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms a group consisting of groups or bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms, or a substituted or unsubstituted carbon number 2 to 10 monocyclic or polycyclic heterocycles.

According to still another embodiment of the present specification, R ₁₅ and R ₁₆ may be bonded to each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms.

According to still another embodiment of the present specification, R ₁₅ and R ₁₆ may be bonded to each other to form a substituted or unsubstituted benzene ring.

According to still another embodiment of the present specification, R ₁₅ and R ₁₆ may be bonded to each other to form a methyl-substituted or unsubstituted benzene ring.

Further, L ₁ and L ₂ may be the same or different from each other, and are each independently selected from a substituted or unsubstituted alkyl or alkyl group having 2 to 30 carbon atoms, -L ₃ -OL ₄ -, - L ₃ -SL ₄ -, -L ₃ -NH-L ₄ -, -L ₃ -CO-L ₄ -, -L ₃ -COO-L ₄ -, -L ₃ -OCO-L ₄ -, -L ₃ a group consisting of -NHCO-L ₄ - and -L ₃ -CONH-L ₄ -;
L ₃ and L ₄ may be the same or different from each other and are a substituted or unsubstituted alkyl or a branched alkyl group having 1 to 30 carbon atoms.

When L ₁ and L ₂ of the same or different, each independently _{-L 3 -OL 4 -, - L} 3 -SL 4 -, - L 3 -NH-L 4 -, - L 3 -CO-L ₄ -, -L ₃ -COO-L ₄ -, -L ₃ -OCO-L ₄ -, -L ₃ -NHCO-L ₄ -, or -L ₃ -CONH-L ₄ -, and L ₃ and L ₄ When they are the same or different from each other, when they are substituted or unsubstituted, a straight or branched alkyl group having 1 to 30 carbon atoms, and when L ₁ and L ₂ are the same or different from each other, they are independently substituted. Or an unsubstituted alkyl or branched alkyl group having 2 to 30 carbon atoms may have the same or similar effects.

The reason is that, when the L ₁ and L ₂ of _{-L 3 -OL 4 -, - L} 3 -SL 4 -, - L 3 -NH-L 4 -, - L 3 -CO-L 4 -, - When L ₃ -COO-L ₄ -, -L ₃ -OCO-L ₄ -, -L ₃ -NHCO-L ₄ -, or -L ₃ -CONH-L ₄ -, is substituted or unsubstituted L ₃ and L _{4 of} a linear or branched alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other, and are each independently selected from a substituted or unsubstituted alkyl or alkyl group having 2 to 20 carbon atoms, L ₃ -OL ₄ -, -L ₃ -SL ₄ -, -L ₃ -NH-L ₄ -, -L ₃ -CO-L ₄ -, -L ₃ -COO-L ₄ -, -L ₃ -OCO a group consisting of -L ₄ -, -L ₃ -NHCO-L ₄ - and -L ₃ -CONH-L ₄ -;
L ₃ and L ₄ may be the same or different from each other, and are a substituted or unsubstituted alkyl or a branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other, and are each independently selected from a substituted or unsubstituted alkyl or alkyl group having from 2 to 10 carbon atoms, L ₃ -OL ₄ -, -L ₃ -SL ₄ -, -L ₃ -NH-L ₄ -, -L ₃ -CO-L ₄ -, -L ₃ -COO-L ₄ -, -L ₃ -OCO a group consisting of -L ₄ -, -L ₃ -NHCO-L ₄ - and -L ₃ -CONH-L ₄ -;
L ₃ and L ₄ may be the same or different from each other, and are a substituted or unsubstituted alkyl or a branched alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other, and are each independently a substituted or unsubstituted alkyl or a branched alkyl group having 2 to 10 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other, and are each independently a substituted or unsubstituted extended ethyl group or a substituted or unsubstituted extended propyl group.

In an embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other, and each independently is an ethyl group or a propyl group.

Further, in an embodiment of the present specification, a is an integer of 0 or 1.

In another embodiment of the present specification, a is zero.

In still another embodiment of the present specification, a is 1.

Further, in an embodiment of the present specification, X is an anionic group.

In an embodiment of the present specification, the X may be selected from the group consisting of at least one element and oxygen selected from the group consisting of tungsten, molybdenum, niobium, and phosphorus. An anion of the compound; an anion containing boron; an anion containing a sulfonic acid group; and an anion containing a halogen group.

In an embodiment of the present specification, the X may be selected from the group consisting of a compound containing at least one element selected from the group consisting of tungsten, molybdenum, rhenium, and phosphorus and oxygen. Anion; triflate anion, bis(trifluoromethylsulfonyl) decylamine anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion And tetrakis(4-fluorophenyl)borate, tetrakis(pentafluorophenyl)borate, tris-trifluoromethanesulfonylmethylate and a halogen group.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following structure, and the following structure represents the isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. The isomer refers to a molecule having mutually different physical properties/chemical properties although the molecular formula is the same.

In the structure, R ₁ to R ₁₆ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1.

According to another embodiment of the present specification, the chemical formula 1 is represented by the following Chemical Formula 2.

[Chemical Formula 2]

In the chemical formula 2,
R ₁ to R ₁₁ , R ₁₃ to R ₁₆ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1,
R ₁₇ and R ₁₈ are the same or different from each other, and are each independently selected from a straight or branched alkyl group having a hydrogen number, a hydrogen group, a hydroxyl group, a substituted or unsubstituted carbon number of 1 to 30, substituted or not. a substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms of a monocyclic or polycyclic group, or bonded to each other A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms is formed.

In one embodiment of the present specification, R ₁₇ and R ₁₈ are the same or different from each other, and are each independently selected from a straight or branched chain having a hydrogen number, a hydrogen group, a hydroxyl group, a substituted or unsubstituted carbon number of 1 to 20. Alkyl, substituted or unsubstituted mono or polycyclic aryl group having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms or monocyclic or polycyclic In the group, or bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, or a substituted or unsubstituted monocyclic ring having 2 to 20 carbon atoms Or a polycyclic heterocycle.

In one embodiment of the present specification, R ₁₇ and R ₁₈ are the same or different from each other, and are independently selected from a straight or branched chain having a hydrogen number, a hydrogen group, a hydroxyl group, a substituted or unsubstituted carbon number of 1 to 10. Alkyl, substituted or unsubstituted mono or polycyclic aryl group having 6 to 12 carbon atoms, and substituted or unsubstituted heterocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms In the group, or bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms, or a substituted or unsubstituted monocyclic ring having 2 to 10 carbon atoms Or a polycyclic heterocycle.

In one embodiment of the present specification, R ₁₇ and R ₁₈ may be bonded to each other to form a substituted or unsubstituted monocyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms.

According to another embodiment of the present specification, R ₁₇ and R ₁₈ may be bonded to each other to form a substituted or unsubstituted benzene ring.

According to still another embodiment of the present specification, R ₁₇ and R ₁₈ may be bonded to each other to form a methyl-substituted or unsubstituted benzene ring.

Further, according to still another embodiment of the present specification, the chemical formula 1 is represented by the following Chemical Formula 3.

[Chemical Formula 3]

In the chemical formula 3,
R ₁ to R ₁₄ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1,
R _{19 is} selected from hydrogen, dihydrogen, substituted or unsubstituted, linear or branched alkyl having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 30 carbon atoms, substituted Or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, monohalogen or polycyclic group, halogen group, nitro group, - a group consisting of COOH, -OH, sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd;
Rb to Rd are the same or different from each other, and each independently is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms;
m is an integer of 1 to 4, and when m is 2 or more, R _{19 is the} same or different from each other.

In another embodiment of the present specification, R _{19 is} selected from the group consisting of hydrogen, dihydrogen, substituted or unsubstituted C 1-20 linear or branched alkyl, substituted or unsubstituted carbon number. Alkoxy group of 1 to 20, substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms a group consisting of aryl, halo, nitro, -COOH, -OH, sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd;
Rb to Rd are the same or different and each independently is a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms;
m is an integer of 1 to 4, and when m is 2 or more, R _{19 is the} same or different from each other.

In still another embodiment of the present specification, R _{19 is} selected from the group consisting of hydrogen, heavy hydrogen, substituted or unsubstituted, linear or branched alkyl having 1 to 10 carbon atoms, substituted or unsubstituted carbon number. Alkoxy group of 1 to 10, substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 12 carbon atoms, substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 10 carbon atoms a group consisting of aryl, halo, nitro, -COOH, -OH, sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd;
Rb to Rd are the same or different and each independently is a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms;
m is an integer of 1 to 4, and when m is 2 or more, R _{19 is the} same or different from each other.

According to still another embodiment of the present specification, R ₁₉ is hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms in a straight or branched chain.

According to still another embodiment of the present specification, R ₁₉ is hydrogen or a substituted or unsubstituted methyl group.

According to still another embodiment of the present specification, R ₁₉ is hydrogen or methyl.

In an embodiment of the present specification, m may be an integer of 1 to 4, and when m is 2 or more, R ₁₉ may be the same or different from each other.

In an embodiment of the present specification, m may be an integer of 1 to 3, and when m is 2 or more, R ₁₉ may be the same or different from each other.

In an embodiment of the present specification, m may be an integer of 1 to 2, and when m is 2, R ₁₉ may be the same or different from each other.

In an embodiment of the present specification, m may be 1.

Further, according to still another embodiment of the present specification, the chemical formula 1 is represented by the following Chemical Formula 4.

[Chemical Formula 4]

In the chemical formula 4,
R ₁ to R ₁₁ , R ₁₃ , R ₁₄ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1,
R ₁₉ and R ₂₀ are the same or different from each other, and are independently selected from hydrogen, dihydrogen, substituted or unsubstituted C 1 to 30 linear or branched alkyl, substituted or unsubstituted carbon. Alkoxy groups of 1 to 30, substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted monocyclic or polycyclic rings having 2 to 30 carbon atoms a group consisting of heteroaryl, halo, nitro, -COOH, -OH, sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd;
Rb to Rd are the same or different from each other, and each independently is a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms;
m is an integer from 1 to 4;
n is an integer from 1 to 4;
When m is 2 or more, R _{19 is the} same or different from each other;
When n is 2 or more, R _{20 is the} same or different from each other.

In an embodiment of the present specification, R ₁₉ and R ₂₀ may be the same or different from each other, and are independently selected from a hydrogen or a heavy hydrogen, a substituted or unsubstituted linear or branched alkane having 1 to 20 carbon atoms. a substituted, unsubstituted or substituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted C 6-20 monocyclic or polycyclic aryl group, substituted or unsubstituted carbon number 2 to 20 monocyclic or polycyclic heteroaryl, halo, nitro, -COOH, -OH, sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd In the group
Rb to Rd may be the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R ₁₉ and R ₂₀ may be the same or different from each other, and are each independently selected from a hydrogen or a heavy hydrogen, a substituted or unsubstituted linear or branched alkyl having 1 to 10 carbon atoms. a substituted, unsubstituted or substituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a monocyclic or polycyclic ring group, a substituted or unsubstituted carbon number 2 to 10 monocyclic or polycyclic heteroaryl, halo, nitro, -COOH, -OH, sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd In the group
Rb to Rd may be the same or different from each other, and each independently is a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R ₁₉ and R ₂₀ may be the same or different from each other, and are each independently hydrogen or a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

According to another embodiment of the present specification, R ₁₉ and R ₂₀ are hydrogen or a substituted or unsubstituted methyl group.

According to still another embodiment of the present specification, R ₁₉ and R ₂₀ are hydrogen or a methyl group.

Further, the compound represented by Chemical Formula 1 may be represented by any one of the following chemical formulas, but is not necessarily limited thereto.

In the formula, X is as defined in the above Chemical Formula 1.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a maximum absorption wavelength of 557 nm to 570 nm. Specifically, the compound represented by Chemical Formula 1 has a maximum absorption wavelength of 557 nm to 560 nm.

In the case where the compound of the present specification satisfies the maximum absorption wavelength of the range, when a red color filter is applied, the color coordinates can be realized in a smaller amount.

With respect to the maximum absorption wavelength, the compound can be dissolved in propylene glycol monomethyl ether acetate (PGMEA) at a concentration of 10 ^-5 mol at 25 ° C, using ultraviolet (ultraviolet, UV ) - Visible spectrometer (SCINCO) to perform the measurement.

Additionally, an embodiment of the present specification provides a color former composition comprising the compound.

Further, according to an embodiment of the present specification, the colorant composition may further include at least one of a dye and a pigment.

For example, the colorant composition may include only the compound of the chemical formula 1, or may include the compound of the chemical formula 1 and one or more dyes, or a compound containing the chemical formula 1 and one or more pigments, or a A compound of Chemical Formula 1, one or more dyes, and one or more pigments.

The dye and pigment may be selected from one or more of the group consisting of a metal-complex compound, an azo compound, and a metal azo compound. , quinophthalone-based compound, isoindoline-based compound, methine-based compound, phthalocyanine-based compound, metal phthalocyanine-based compound, porphyrin (porphyrin) a compound, a metal porphyrin compound, a tetra aza porphyrin compound, a metal tetra aza porphyrin compound, a Cyanine compound, a xanthene-based compound, a metal dipyrromethane-based compound, a boron dipyrromethane-based compound, a metal dipyrromethane-based compound, Anthraquinone compound, diketopyrrolopyrrole compound, three It is composed of a triarylmethane compound and a perylene compound.

According to an embodiment of the present specification, the pigment further contained in addition to the compound of Chemical Formula 1 may be, for example, R254 (Pigment Red 254), but is not limited thereto. The R254 may be in the state of Millbase or may be commercially available. The polishing base refers to a state in which a dispersing agent, a binder, and the like are added to an undissolved coloring agent, and the composition is sufficiently dispersed.

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

According to an embodiment of the present specification, the photosensitive resin composition contains the compound represented by Chemical Formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

The photosensitive resin composition may further contain the pigment.

The binder resin is not particularly limited as long as it exhibits physical properties such as strength and developability of the film produced from the photosensitive resin composition.

The binder resin may be a copolymerized resin of a polyfunctional monomer imparting mechanical strength to the film and a monomer which imparts alkali solubility, and may further contain a binder which is generally used in the art.

The polyfunctional monomer which imparts mechanical strength to the film may be at least one of an unsaturated carboxylic acid ester, an aromatic vinyl group, an unsaturated ether, an unsaturated quinone imide, and an acid anhydride.

Specific examples of the unsaturated carboxylic acid esters may be selected from the group consisting of benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, (methyl) ) butyl acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, (methyl) Isobornyl acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, hydroxyethyl (meth)acrylate, (A) 2-hydroxypropyl acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, decyloctyloxy (meth)acrylate 2-hydroxypropyl ester, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy diethylene Alcohol (meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, benzene Oxydiethylene glycol (meth) acrylate, p-nonyl phenoxy Polyethylene glycol (meth) acrylate, p-nonyl phenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, (meth) acrylate -1,1,1,3,3,3-hexafluoroisopropyl ester, octafluoropentyl (meth)acrylate, heptadecafluoro(meth)acrylate, tribromophenyl (meth)acrylate, The α-hydroxymethyl methacrylate, α-hydroxyethyl methacrylate, α-hydroxypropyl methacrylate, and α-hydroxy methacrylate butyl ester are not limited thereto.

Specific examples of the aromatic vinyl group may be selected from the group consisting of styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxystyrene and ( Among the groups consisting of o-, m-, p-chlorostyrene, but 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 quinone imines may be selected from N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxybenzene The group consisting of butylenediamine and N-cyclohexylmethyleneimine is not limited to these.

The acid anhydride may be, but is not limited to, maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride or the like.

The base which imparts alkali solubility is not particularly limited as long as it contains an acid group, and for example, it is preferably selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, and antibutene. Diacid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono-2-((meth)propenyloxy)ethyl phthalate, succinic acid mono- One or more of the group consisting of 2-((meth)acrylenyloxy)ethyl ester and ω-carboxypolycaprolactone mono(meth)acrylate, but is not limited thereto.

According to an embodiment of the present specification, the binder resin has an acid value of 50 KOHmg/g to 130 KOHmg/g and a weight average molecular weight of 1,000 g/mol to 50,000 g/mol.

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

In an embodiment of the present specification, the binder resin may be benzyl methacrylate in mass ratio: N-phenyl maleimide: styrene: methacrylic acid = 55:9:11 : 25 copolymer.

The polyfunctional monomer is a monomer that functions to form a photoresist image by light, and specifically may be selected from the group consisting of propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, and neopentyl Alcohol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanurate Group consisting of trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate One or a mixture of two or more.

In an embodiment of the present specification, the polyfunctional monomer may be Dipentaerythritol hexaacrylate (DPHA).

The photoinitiator is not particularly limited as long as it is a radical generating radical to promote cross-linking by light, and may be, for example, selected from the group consisting of an acetophenone-based compound, a biimidazole-based compound, and a triazine-based compound. And one or more of the group consisting of lanthanide compounds.

The acetophenone-based compound is: 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane- 1-ketone, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether Benzoin, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholinyl-1-propan-1-one , 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-1-one, 2-(4-bromo-benzyl-2-dimethylamino 1-(4-morpholinylphenyl)-butan-1-one or 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropan-1-one It is not limited to these.

The biimidazole-based compound is: 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 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'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. It is not limited to these.

The triazine-based compound is: 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3 ,3-hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionate, ethyl-2-{4 -[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis( Trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl Phenylthio}acetate, benzyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 3-{chlorine -4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4-[2,4-bis(trichloromethyl)-all Triazin-6-yl]phenylthio}propanamine, 2,4-bis(trichloromethyl)-6-p-methoxystyryl-s-triazine, 2,4-bis(trichloromethane) 6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxybenzene The vinyl-s-triazine or the like is not limited thereto.

The lanthanide compounds are: 1,2-octanedione,-1-(4-phenylthio)phenyl,-2-(o-benzylidene fluorene) (Ciba-Geigy) Company, CGI124), Ethyl-1-(9-ethyl)-6-(2-methylbenzimid-3-yl)-, 1-(O-ethylindenyl) (CGI242), N -1919 (ADEKA), etc., is not limited to these.

In an embodiment of the present specification, the photoinitiator may be PBG-3057.

The solvent may be one or more selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1, 4-Dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl Ether, chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, Hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methyl Oxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, propylene glycol diethyl ether acetate, 3-methoxybutyl acetate, 3-ethoxy Ethyl propyl propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether are not limited thereto.

In an embodiment of the present specification, the solvent may be propylene glycol monomethyl ether acetate.

In one embodiment of the present specification, the content of the compound represented by the chemical formula 1 may be 5% by weight to 60% by weight based on the total weight of the photosensitive resin composition, and the binder resin is The content is from 1% by weight to 60% by weight, the content of the photoinitiator is from 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight, the content of the solvent It is 10% by weight to 80% by weight.

According to an embodiment of the present specification, the content of the compound represented by Chemical Formula 1 is 5% by weight to 60% by weight based on the total weight of the solid content in the photosensitive resin composition, and the binder The content of the resin is from 1% by weight to 60% by weight, the content of the photoinitiator is from 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer is from 0.1% by weight to 50% by weight.

The total weight of the solid component refers to the total weight of components other than the solvent in the photosensitive resin composition. The basis of the solid content and the weight % based on the solid content of each component can be measured by a usual analytical method used in the art, such as liquid chromatography or gas chromatography.

In an embodiment of the present specification, the photosensitive resin composition may further contain an additive.

According to one embodiment of the present specification, the photosensitive resin composition further comprises a photocrosslinking sensitizer, a curing accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and a dispersion. One or two or more additives in the group consisting of a agent, a secondary agent, and a leveling agent.

In the present specification, the additive may be a leveling agent and an auxiliary agent.

The photosensitive resin composition may further comprise the pigment, the leveling agent, and the adhesion aid.

In one embodiment of the present specification, the content of the compound represented by the chemical formula 1 may be 5% by weight to 60% by weight based on the total weight of the photosensitive resin composition, and the content of the pigment is 5 to 40% by weight, the content of the binder resin is 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the content of the polyfunctional monomer The content of the solvent is from 10% by weight to 80% by weight, the content of the additive is from 0.1% by weight to 20% by weight, and the content of the additive is from 0.1% by weight to 20% by weight.

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

The photocrosslinking sensitizer may be one or more selected from the group consisting of benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4- Bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3,3-dimethyl- a benzophenone compound such as 4-methoxybenzophenone or 3,3,4,4-tetrakis(t-butylperoxycarbonyl)benzophenone; 9-fluorenone, 2-chloro-9 Anthrone-based compounds such as anthrone and 2-methyl-9-fluorenone; thioxanthone, 2,4-diethylthiazinone, 2-chlorothiazepinone, 1-chloro-4- a thioxanthone compound such as propyloxy thioxanthone, isopropyl thioxanthone or diisopropyl thioxanthone; oxazepine such as xanthone or 2-methyloxaxanone; Ketone compounds; anthraquinone compounds such as hydrazine, 2-methyl hydrazine, 2-ethyl hydrazine, tert-butyl hydrazine, 2,6-dichloro-9,10-fluorene; 9-benzene Acridine such as pyridinium, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane), 1,3-bis(9-acridinyl)propane Compound; benzoin, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-dione, 9,10-phenanthrene Iso-dicarbonyl compound; 2,4,6-trimethylbenzimidyldiphenylphosphine oxide, bis(2,6-dimethoxybenzylidene)-2,4,4-trimethylpentyl a phosphine oxide compound such as phosphine oxide; methyl-4-(dimethylamino)benzoate, ethyl-4-(dimethylamino)benzoate, 2-n-butoxy B a benzoate compound such as -4-(dimethylamino)benzoate; 2,5-bis(4-diethylaminobenzylidene)cyclopentanone, 2,6-bis ( An amine-based synergist such as 4-diethylaminobenzylidene)cyclohexanone or 2,6-bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone; 3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin, 3-benzylidene- 7-(Diethylamino)coumarin, 3-benzylidene-7-methoxy-coumarin, 10,10-carbonyl bis[1,1,7,7-tetramethyl-2 , 3,6,7-tetrahydro-1H,5H,11H-C1]-benzopyrano[6,7,8-ij]-quinolizin-11-one and other coumarin compounds; 4-di A chalcone compound such as ethylaminochalcone or 4-azidobenzylideneacetophenone; 2-benzylidenemethylene, 3-methyl-b-naphthylthiazoline.

The hardening accelerator is used for the purpose of improving hardening and mechanical strength. Specifically, one or more selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and 2 may be used. -mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis(3-mercaptopropionate) , pentaerythritol-tris(3-mercaptopropionate), pentaerythritol-tetrakis(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2-mercaptoacetate) Ester) and trimethylolpropane-tris(3-mercaptopropionate).

The adhesion promoter used in the present specification may be selected from the group consisting of methacryl methoxy propyl trimethoxy decane, methacryl methoxy propyl dimethoxy decane, and methacryl methoxy propyl group. One or more kinds of methacryl decyl decane coupling agents such as triethoxy decane and methacryl methoxy propyl dimethoxy decane, and alkyl trimethoxy decane may be derived from octyl trimethoxy decane. One or more selected from the group consisting of dodecyltrimethoxydecane and octadecyltrimethoxydecane are used.

The surfactant is an anthrone-based surfactant or a fluorine-based surfactant. Specifically, an anthrone-based surfactant can be used: BYK-077, BYK-085 of BYK-Chemie. 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., fluorine-based surfactants can be used: DIC (DaiNippon Ink & Chemicals) company's 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., but not limited to these .

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

Specific examples of the antioxidant include a phosphate-based heat stabilizer such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol and octadecane; 3-(4-hydroxy-3,5-di-t-butylphenyl)propionate, tetra-bis[methylene-3-(3,5-di-t-butyl-4-hydroxyl) Phenyl)propionate]methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 3,5- Di-t-butyl-4-hydroxybenzyl phosphite, 2,2-thiobis(4-methyl-6-tert-butylphenol), 2,6-g, t-butyl Phenol 4,4'-butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or double [ 3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid]diol (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl) Hindered phenol such as butanoic acid]glycol ester) is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine Or an amine-based secondary antioxidant such as N,N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thio Sulfate, mercaptobenzothiazole or tetramethylthiuram disulfide tetras[methylene-3-(laurylthio)propionate]methane (Thio) secondary antioxidant; or three Phenyl phosphite, tris(nonylphenyl) phosphite, triisodecyl phosphite, bis(2,4-dibutylphenyl)pentaerythritol diphosphite (Bis(2,4-dibutylphenyl) ) Pentaerythritol Diphosphite) or (1,1'-biphenyl)-4,4'-diylbisphosphonic acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl] ester (( A phosphite-based secondary antioxidant such as 1,1'-Biphenyl)-4,4'-Diylbisphosphonous acid tetrakis [2,4-bis(1,1-dimethylethyl)phenyl] ester).

The ultraviolet absorber may be used: 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc., but It is not limited to these, and is generally available to users in the art.

The thermal polymerization preventing agent may, for example, comprise one or more selected from the group consisting of p-anisole, hydroquinone, pyrocatechol, and tert-butylcatechol. (tert-butyl catechol), N-nitrosophenylhydroxylamine ammonium salt, N-nitrosophenylhydroxylamine aluminum salt, p-methoxyphenol, di-tert-butyl-p-cresol, ortho-benzene Trisphenol, benzoquinone, 4,4-thiobis(3-methyl-6-tert-butylphenol), 2,2-methylenebis(4-methyl-6-tert-butylphenol) 2-mercaptoimidazole and phenothiazine, but not limited thereto, may be generally known in the art.

The dispersant may be used in a method of internally adding to a pigment in a form in which a pigment is surface-treated in advance or a method of externally adding it to a pigment. As the dispersing agent, a compound type, a nonionic, an anionic or a cationic dispersing agent can be used, and examples thereof include a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactant. These may be used separately or in combination of two or more.

Specifically, the dispersing agent is selected from the group consisting of polyalkylene glycols and esters thereof, polyoxyalkylene alkyl polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonates, sulfonates And one or more of the group consisting of a carboxylate, a carboxylate, a alkylguanamine alkylene oxide adduct, and an alkylamine, but is not limited thereto.

The leveling agent can be polymeric or non-polymeric. Specific examples of the polymer leveling agent include polyethyleneimine, polyamidamine, an amine and an epoxide reaction product, and specific examples of the non-polymeric leveling agent include a non-polymer sulfur-containing compound. And non-polymer nitrogen-containing compounds, but are not limited thereto, and are generally used by users in the art.

In an embodiment of the present specification, the leveling agent may be F-554.

The adjunct agent is not particularly limited and can be generally used by users in the art.

In an embodiment of the present specification, the adhesion aid may be KBM-503.

According to an embodiment of the present specification, a photosensitive material produced by using the photosensitive resin composition is provided.

More specifically, the photosensitive resin composition of the present specification is applied onto a substrate by an appropriate method and cured to form a photosensitive material in a film or pattern form.

The coating method is not particularly limited, and a spray method, a roll coating method, a spin coating method, or the like can be used, and a spin coating method is usually widely used. Further, after the coating film is formed, a part of the residual solvent can be removed under reduced pressure as the case may be.

The light source for curing the photosensitive resin composition of the present specification includes, for example, a mercury vapor arc (arc), a carbon arc, a Xe arc, or the like which disperses light having a wavelength of 250 nm to 450 nm, but is not limited thereto.

The photosensitive resin composition of the present specification can be used for a thin film transistor liquid crystal display (TFT LCD) color filter manufacturing pigment dispersion type photosensitive material, 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, a photosensitive material for forming an overcoat layer, a columnar spacer photosensitive material, a photocurable coating material, a photocurable ink, a photocurable adhesive, a printing plate, and printing. In the photosensitive material for a wiring board, a photosensitive material for a plasma display panel (PDP), etc., the use is not specifically limited.

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

The color filter can be produced using a photosensitive resin composition containing the compound represented by the above Chemical Formula 1. The photosensitive resin composition is applied onto a substrate to form a coating film, and the coating film is exposed, developed, and cured, whereby a color filter can be formed.

The photosensitive resin composition according to an embodiment of the present invention is excellent in heat resistance, and has little color change due to heat treatment. When a color filter is manufactured, a color reproduction rate, brightness, and brightness can be provided even by a hardening process. A high ratio color filter.

The substrate may be a glass plate, a ruthenium wafer, a plate of a plastic substrate such as polyether sulfone (PES) or polycarbonate (PC), and the like, and the kind thereof is not particularly limited.

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

According to another embodiment, the color filter may further comprise an outer coating.

Between the color pixels of the color filter, a lattice-like black pattern called a black matrix can be arranged for the purpose of enhancing contrast. The material of the black matrix can use chromium. In this case, the chromium can be vapor-deposited on the entire glass substrate, and a pattern can be formed by an etching process. However, in consideration of the high cost in the step, the high reflectance of chromium, and the environmental pollution caused by the chromium waste liquid, a resin black matrix using a pigment dispersion method capable of microfabrication can be used.

The black matrix of one embodiment of the present specification may use a black pigment or a black dye as a colorant. For example, carbon black may be used alone or in combination with a color pigment. In this case, since the coloring pigment having insufficient light-shielding property is mixed, there is an advantage that even if the amount of the colorant is relatively increased, the strength of the film or The adhesion of the substrate is also not lowered.

A display device including the color filter of the present specification is provided.

The display device may be a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), or a liquid crystal display device (Liquid Crystal Display, Any of LCD, Thin Film Transistor-Liquid Crystal Display (LCD-TFT) and Cathode Ray Tube (CRT).
[Examples]

Hereinafter, the embodiments to be specifically described in the specification will be described in detail. However, the embodiments of the present specification can be modified into various different 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 provide a more complete description of the present specification to those of ordinary skill in the art.

Manufacturing example.
[Production of Compound A]

To a solution of Phthalic anhydride (11.8 g (0.08 mol/1 eq), 80 ml of distilled water was added, and after stirring at room temperature for 30 minutes, N-Ethyl ethylenediamine (7.26 g) was added. 0.082 mol / 1.03 eq), and then the temperature was raised to 105 ° C while stirring. After reacting for 4 hours, it was cooled to normal temperature.
The distilled water was removed under reduced pressure, and acetone 60 mL was added thereto, and the mixture was stirred at normal temperature for 2 hours. The acetone was removed under reduced pressure and recrystallized from isopropyl alcohol (IPA) to give white powder (13.5 g). (Yield 77.37%)
Ionization mode: APCI+: m/z=219[M+H]+, exact molecular weight (Exact Mass): 218

[Manufacture of Compound B]

Add Phthalic anhydride 11.8 g (0.08 mol/1 eq) and N-isopropylethane-1,2-diamine 8.42 g (0.082 mol) /1.03 eq), which was produced by the same method as Compound A, to obtain 10.5 g of Compound B1. (yield 57%)
Ionization mode: APCI+: m/z = 233 [M + H] +, exact molecular weight: 232

[Manufacture of Compound C]

Phthalic anhydride 11.8 g (0.08 mol/1 eq) and 2-((2-aminoethyl)amino)ethane-1-ol (2-((2-aminoethyl)amino) Ethyl-1-ol) 8.54 g (0.082 mol / 1.03 eq) was produced by the same method as Compound A to obtain 12.3 g of Compound C. (yield is 65%)
Ionization mode: APCI+: m/z=235[M+H]+, exact molecular weight: 234

[Manufacture of Compound D]

Add Phthalic anhydride 11.8 g (0.08 mol/1 eq) and N-ethylpropane-1,3-diamine 8.38 g (0.082 mol/1.03) Eq) was produced by the same method as Compound A to obtain 14.2 g of Compound D. (yield 76.4%)
Ionization mode: APCI+: m/z = 233 [M + H] +, exact molecular weight: 232

[Manufacture of Compound E]

0.81 g (0.002 mol, 1 eq) of Dichlorosulfo fluorescein was dissolved in 30 mL of methanol (MeOH), and 1.04 g (0.01 mol, 5 eq) of diethylamine was added thereto. The reaction was carried out for 2 hours. The reaction was quenched by quenching with a 1 M aqueous solution of hydrochloric acid (HCl) and extracted with CH ₂ Cl ₂ .
The organic layer was separated and washed with brine, dried over Na ₂ SO ₄ , and reduced to remove solvent. Purification by Silica column chromatography (CH ₂ Cl ₂ : MeOH = 8:1) gave 0.52 g of Compound E. (yield 56%)

[Manufacture of Compound 1]

2 g (0.009 mol/3 eq) of Compound A was added to 25 mL of distilled water, and 1.24 g (0.009 mol/3 eq) of potassium carbonate (K ₂ CO ₃ ) was added while stirring. After stirring for 30 minutes while raising the temperature to 60 ° C, 1.22 g (0.003 mol / 1 eq) of dichlorosulfo fluorescein was added.
After stirring at 105 ° C for 24 hours, it was cooled to room temperature. The reaction was completed by quenching with a 0.1 M hydrochloric acid (HCl) aqueous solution, and the precipitate was thoroughly washed with distilled water, filtered under reduced pressure, and dried in an oven at 80 °C. Purification by Silica column chromatography (CH ₂ Cl ₂ : MeOH = 7:1) gave 1.1 g of Compound 1. (yield 47%)
Ionization mode: APCI+: m/z=769[M+H]+, exact molecular weight: 768

[Manufacture of Compound 2]

2.09 g (0.009 mol/3 eq) of Compound B, Dichlorosulfo fluorescein 1.22 g (0.003 mol/1 eq) was added, and the same procedure as Compound 1 was carried out to obtain 0.98 g of Compound 2 . (yield 41%)
Ionization mode: APCI+: m/z=797[M+H]+, exact molecular weight: 796

[Manufacture of Compound 3]

2.1 g (0.009 mol/3 eq) of Compound C, Dichlorosulfo fluorescein 1.22 g (0.003 mol/1 eq) was added, and the same procedure as Compound 1 was carried out to obtain 1.3 g of Compound 3 . (yield 54%)
Ionization mode: APCI+: m/z=801[M+H]+, exact molecular weight: 800

[Manufacture of Compound 4]

2.09 g (0.009 mol/3 eq) of Compound D, Dichlorosulfo fluorescein 1.22 g (0.003 mol/1 eq) was added, and the same procedure as Compound 1 was carried out to obtain 0.85 g of Compound 4. . (yield 36%)
Ionization mode: APCI+: m/z=797[M+H]+, exact molecular weight: 796

[Manufacture of Compound 5]

0.65 g (0.003 mol/3 eq) of Compound A and 0.52 g (0.001 mol/1 eq) of Compound E were added, and the same procedure as Compound 1 was carried out to obtain 0.25 g of Compound 5. (yield 40%)
Ionization mode: APCI+: m/z = 624 [M+H]+, exact molecular weight: 623

Compound of Comparative Example 1

Rhodamine 6G was used as the compound of Comparative Example 1.

Compound of Comparative Example 2

5 g (7.388 mmol) of Acid Red 289, 3.961 g (14.776 mmol) of N-(3-bromopropyl)phthalimide, 4.09 g (29.554 mmol) of K ₂ CO _{3 was} placed in 100 ml of N-Methyl Pyrrolidone (NMP) and stirred at 95 ° C for 12 hours. The reaction solution was cooled to normal temperature, and filtered under reduced pressure. The filtrate was added to 800 ml of ethyl acetate (Ethyl acetate). After stirring at room temperature for 30 minutes, the precipitate was filtered under reduced pressure to give the compound of Comparative Example 2.

Example.
[Manufacture of Example 1 of Photosensitive Resin Composition]
15 parts by weight of the previously produced compound 1, 33 parts by weight of the pigment R254, and 16 parts by weight of the binder A as a binder resin, 4.5 parts by weight based on 100 parts by weight based on the total weight of the photosensitive resin composition Polyfunctional monomer (Dipentaerythritol hexaacrylate), 0.3 parts by weight of leveling agent F-554, 0.15 parts by weight of the next auxiliary agent KBM-503, 0.5 part by weight of photoinitiator (PBG) -3057), 30.55 parts by weight of a solvent propylene glycol monomethyl ether acetate (PGMEA, Propylene Glycol Monomethyl Ether Acetate) was mixed to prepare a photosensitive resin composition of Example 1.
The binder A used as the binder resin is a copolymer having a mass ratio of benzyl methacrylate: N-phenyl maleimide: styrene: methacrylic acid = 55:9:11:25 .

[Production of Example 2 to Example 5 of Photosensitive Resin Composition]
The photosensitive resin composition was produced by the same method as Example 1 of the photosensitive resin composition except that the compound 1 of Example 1 of the photosensitive resin composition was changed to the compound of the following Table 1. Example 2 to Example 5.

[Table 1]

Comparative example.
[Production of Comparative Example 1 of Photosensitive Resin Composition]
A photosensitive resin composition was produced by the same method as in Example 1 of the photosensitive resin composition, except that the compound 1 of Example 1 of the photosensitive resin composition was changed to the compound of Comparative Example 1 (rhodamine 6G). Comparative Example 1 of the object.

[Production of Comparative Example 2 of Photosensitive Resin Composition]
Comparative Example 2 of the photosensitive resin composition was produced in the same manner as in Example 1 of the photosensitive resin composition, except that the compound 2 of Example 1 of the photosensitive resin composition was changed to the compound of Comparative Example 2.

Experimental example.
[Production of substrate]
The photosensitive resin composition produced by the above Comparative Example 1 and Examples 1 to 5 was spin-coated on glass (5 cm × 5 cm), and preheated at 100 ° C for 100 seconds (Prebake). To form a film.
The entire surface of the substrate was irradiated to the substrate on which the film was formed by using an exposure machine at an exposure amount of 40 mJ/cm ² . 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 prepare a substrate.

[Heat resistance evaluation]
For a Post bake (primary) substrate prepared under the above-described conditions, an absorption spectrum in a wavelength range of 380 nm to 780 nm was obtained using a spectrometer (MCPD, Otsuka Co., Ltd.).
Further, a post-bak (primary) substrate was additionally treated at 230 ° C for 60 minutes, and a transmittance spectrum was obtained by the same equipment and the same measurement range.
Using the values L*, a*, b* obtained from the absorption spectrum obtained by using the C light source as a backlight, ΔEab was calculated by the following calculation formula 1, and is shown in Table 2 below.

[Calculation 1]
ΔEab(L*, a*, b*)={(ΔL*) ² +(Δa*) ² +(Δb*) ² } ^1/2
A small ΔEab value means that the color change is small, indicating that the heat resistance is excellent.

[Table 2]

In Table 2, 60 minutes means that the post-heat treatment substrate is additionally treated at 230 ° C for 60 minutes, and 20 minutes means post-heat treatment (post bake) at 230 ° C for 20 minutes.

[Foreign object evaluation]
If the surface of the substrate produced in the 1 cm × 1 cm region has 15 or more foreign substances, it is denoted by X, and if it is 6 to 14 pieces, it is denoted by △, and if it is 5 or less, it is denoted by ○, and is indicated by ○. Table 3 below.

[table 3]

It is understood that, as in the chemical formula 1 of one embodiment of the present specification, in the case of a compound in which an alkylphthalimide is substituted on a nitrogen atom, the existing grinding base (Mill base) is not hindered. When it is mixed with the R254 polishing base (Mill base), the amount of foreign matter on the surface is small, and the pigment can be stabilized at a high temperature, and the color change caused by the additional heat treatment is small. The term "Mill base" refers to a state in which a dispersing agent, a binder, and the like are added to an undissolved coloring agent, and the composition is sufficiently dispersed.

[Determination of Luminance of Color Coordinates]
The photosensitive resin composition produced in the above Comparative Example 2 and Examples 1 to 5 was spin-coated on glass (5 cm × 5 cm), and preheated at 100 ° C for 100 seconds (Prebake). To form a film.
The entire surface of the substrate was irradiated to the substrate on which the film was formed by using an exposure machine at an exposure amount of 40 mJ/cm ² . 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 prepare a substrate.
The color coordinates (x, y) and the luminance (Y) of the produced substrate were measured using a spectroscope (MCPD, Otsuka Co., Ltd.), and are shown in Table 4 below.

[Table 4]

According to the above Table 4, it was confirmed that the substrates produced in Examples 1 to 5 had higher luminance than the substrates produced in Comparative Example 2, and exhibited excellent color characteristics.

[Measurement of Maximum Absorption Wavelength]
The compound of Comparative Example 2 and the compound 1 to the compound 5 were each dissolved in propylene glycol monomethyl ether acetate (PGMEA) at 25 ° C at a concentration of 10 ^-5 mol, using a UV-visible spectrometer (Sinko) The company) was used to determine the maximum absorption wavelength, which is shown in Table 5 below.

[table 5]

According to the above Table 5, it was confirmed that the maximum absorption wavelength of the compound 1 to the compound 5 was longer than that of the compound of Comparative Example 2, and the length of the compound 1 to 5 was longer than 5 nm to 8 nm, when red color filtering was applied. Color coordinates can be implemented in smaller quantities.

no

no

Claims (15)

A compound represented by the following Chemical Formula 1: [Chemical Formula 1] In the chemical formula 1, R ₁ to R ₆ are the same or different from each other, and are each independently selected from a straight or branched chain having 1 to 30 carbon atoms, such as hydrogen, a heavy hydrogen, a halogen group, a nitro group, a substituted or unsubstituted group. Alkyl, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted a group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; R ₇ to R ₁₁ are the same or different from each other, and are independently selected from hydrogen, dihydrogen, halogen, -OH, - SO ₃ ^- , -SO ₃ H, -SO ₃ Ra, -SO ₂ NRbRc, -SO ₂ NHRd, -COOH, -COORa, -CONRd, substituted or unsubstituted linear or branched carbon number 1 to 30 a chain alkyl group, a substituted or unsubstituted hexacyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms In the group formed; Ra to Rd are the same or different from each other, and are independently selected from a substituted or unsubstituted C 1 to 30 linear or branched alkyl group, a substituted or unsubstituted carbon. Number 6 to 30 Monocyclic group or polycyclic heteroaryl group consisting of cycloalkyl or aryl ring, and a substituted or unsubstituted carbon atoms of 2 to 30; R ₁₂ selected from the group consisting of hydrogen, heavy hydrogen, substituted or Unsubstituted alkyl or linear alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted C 6 to 30 monocyclic or polycyclic aryl group, substituted or unsubstituted carbon number a group consisting of 2 to 30 monocyclic or polycyclic heteroaryl groups, and a dianhydride group containing a nitrogen atom; R ₁₃ and R ₁₄ are the same or different from each other, and are independently substituted or unsubstituted. a linear or branched alkyl group having 1 to 30 carbon atoms; R ₁₅ and R ₁₆ are the same or different from each other, and are independently selected from hydrogen, dihydrogen, -OH, substituted or unsubstituted carbon number 1 to 30 A straight or branched alkyl group, a substituted or unsubstituted hexacyclic or polycyclic aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted monocyclic or polyhydric group having 2 to 30 carbon atoms a group of heteroaryl groups of a ring, or bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, or substituted or unsubstituted a monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms; L ₁ and L ₂ are the same or different from each other, and are each independently selected from a direct bond, a substituted or unsubstituted carbon number of 2 to 30 chain or branched alkylene _{chain, -L 3 -OL 4 -, -} L 3 -SL 4 -, - L 3 -NH-L 4 -, - L 3 -CO-L 4 -, - L 3 -COO -L ₄ -, -L ₃ -OCO-L ₄ -, -L ₃ -NHCO-L ₄ - and -L ₃ -CONH-L ₄ - are grouped; L ₃ and L ₄ are the same or different from each other And is a substituted or unsubstituted alkyl or a branched alkyl group having 1 to 30 carbon atoms; a is an integer of 0 or 1; and X is an anionic group. The compound according to claim 1, wherein the chemical formula 1 is represented by the following Chemical Formula 2: [Chemical Formula 2] In the chemical formula 2, R ₁ to R ₁₁ , R ₁₃ to R ₁₆ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1, and R ₁₇ and R ₁₈ are the same or different from each other, and independently Selected from a hydrogen or a heavy hydrogen, -OH, a substituted or unsubstituted alkyl group having a linear or branched carbon number of 1 to 30, a substituted or unsubstituted single ring or a plurality of carbon atoms of 6 to 30 a ring-containing aryl group, and a substituted or unsubstituted group of 2 to 30 carbon monocyclic or polycyclic heteroaryl groups, or bonded to each other to form a substituted or unsubstituted carbon number 6 to a monocyclic or polycyclic aromatic hydrocarbon ring of 30, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms. The compound according to claim 1, wherein the chemical formula 1 is represented by the following Chemical Formula 3: [Chemical Formula 3] In the chemical formula 3, R ₁ to R ₁₄ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1, and R _{19 is} selected from hydrogen, heavy hydrogen, substituted or unsubstituted carbon number 1 a linear or branched alkyl group of ～30, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, a halogen group, a nitro group, -COOH, -OH, -SO ₃ ^- , a sulfonic acid group, a sulfonate group, a group consisting of a sulfonate group, -SO ₂ NbRc and -SO ₂ NHRd; Rb to Rd are the same or different from each other, and are independently a substituted or unsubstituted linear or branched carbon number of 1 to 30; The alkyl group of the chain; m is an integer of 1 to 4, and when m is 2 or more, R _{19 is the} same or different from each other. The compound according to claim 1, wherein the chemical formula 1 is represented by the following Chemical Formula 4: [Chemical Formula 4] In the chemical formula 4, R ₁ to R ₁₁ , R ₁₃ , R ₁₄ , L ₁ , L ₂ , a and X are as defined in the above Chemical Formula 1, and R ₁₉ and R ₂₀ are the same or different from each other, independently of each other Selective hydrogen, heavy hydrogen, substituted or unsubstituted alkyl or linear alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or not a substituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, a halogen group, a nitro group, a -COOH group, a group consisting of -OH, -SO ₃ ^- , sulfonate, sulfonate, sulfonate, -SO ₂ NbRc and -SO ₂ NHRd; Rb to Rd are the same or different from each other, independently Rb ～Rd are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; m is an integer of 1 to 4; n is an integer of 1 to 4; and when m is 2 or more R _{19 is the} same or different from each other; when n is 2 or more, R _{20 is the} same or different from each other. The compound of claim 1, wherein the X is selected from the group consisting of at least one selected from the group consisting of tungsten, molybdenum, rhenium, and phosphorus. An anion of a compound of an element and oxygen; an anion containing boron; an anion containing a sulfonic acid group; and an anion containing a halogen group. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas: In the formula, X is as defined in the above Chemical Formula 1. The compound according to claim 1, wherein R ₁₃ and R ₁₄ are the same or different from each other, and each independently is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms in a straight or branched chain. A coloring agent composition comprising the compound according to any one of claims 1 to 7. The color former composition of claim 8, which further comprises at least one of a dye and a pigment. A photosensitive resin composition comprising the compound according to any one of claims 1 to 7, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. The photosensitive resin composition according to claim 10, wherein the content of the compound represented by Chemical Formula 1 is 5% by weight based on the total weight of the solid content in the photosensitive resin composition. 60% by weight, The content of the binder resin is from 1% by weight to 60% by weight, The content of the photoinitiator is from 0.1% by weight to 20% by weight, The content of the polyfunctional monomer is from 0.1% by weight to 50% by weight. The photosensitive resin composition according to claim 10, further comprising an additive. A photosensitive material produced by using the photosensitive resin composition as described in claim 10 of the patent application. A color filter comprising the photosensitive material according to claim 13 of the patent application. A display device comprising the color filter of claim 14 of the patent application.