TW201942255A - Quinophthalone-based compound, photosensitive resin composition, photoresist, color filter, and display device comprising the same - Google Patents

Abstract

Provided in the present specification are a compound represented by chemical formula 1, a photosensitive resin composition comprising same, a photosensitive material, a color filter, and a display device.

Description

Quinoline yellow compounds, photosensitive resin composition including the same, photoresist, color filter, and display device

This application claims the priority and rights of Korean Patent Application No. 10-2018-0039312 filed with the Korean Patent Office on April 4, 2018, and incorporates all its contents into this specification.
The present specification relates to a quinoline yellow-based compound and a photosensitive resin composition containing the quinoline yellow-based compound. In addition, the present specification relates to a photosensitive material manufactured using the photosensitive resin composition, a color filter, and a display device including the color filter.

Recently, a color filter is required to be characterized by high brightness and high contrast ratio. In addition, one of the main goals in the development of display devices is to differentiate the performance of display elements due to the improvement in color purity and to improve the productivity in manufacturing steps.

Previously, the type of pigment used in the coloring material of the color filter existed in the color photoresist in a dispersed state of particles, so it was difficult to adjust the brightness and contrast ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, aggregation in a color filter reduces solubility and dispersibility, and causes multiple scattering of light due to aggregation of large particles. The scattering of such polarized light becomes the main cause of the decrease in contrast ratio. Efforts are being made to improve brightness and contrast ratios by ultra-micronization and dispersion stabilization of pigments, but the degree of freedom in selecting coloring materials to achieve color coordinates for high-color purity display devices is limited. In addition, a pigment dispersion method using a developed coloring material, particularly a pigment, has reached a limit in terms of improving the color purity, brightness, and contrast ratio of a color filter using the color filter.

Therefore, it is required to develop a novel coloring material that can improve color purity to improve color reproduction, brightness, and contrast ratio.

[Problems to be Solved by the Invention]
The present inventors have provided a quinoline yellow-based compound having a novel structure, a photosensitive resin composition containing the quinoline yellow-based compound, a photosensitive material manufactured using the photosensitive resin composition, a color filter, and A display device including the color filter.
[Means for solving problems]

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

In the chemical formula 1,
At least one of R1 and R3 is represented by the following Chemical Formula 2 or Chemical Formula 3,
[Chemical Formula 2]



[Chemical Formula 3]



In the chemical formula 2 and the chemical formula 3,
Indicates a part connected to the chemical formula 1,
X is O or NH,
L is a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, a substituted or unsubstituted alkylene, or a substituted or unsubstituted alkylene,
M is a direct bond, substituted or unsubstituted alkylene, substituted or unsubstituted heteroalkyl, substituted or unsubstituted alkylene, substituted or unsubstituted alkylene Or a substituted or unsubstituted divalent dianhydride group containing a nitrogen atom,
In R1 and R3, which is not the above Chemical Formula 2 or Chemical Formula 3, R4, R41, and R42 are the same or different from each other, and are independently selected from hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, -COR, -COOR, amidino, amidino, anionic, sulfonic, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkane Group, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted In the group consisting of a substituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent groups may be bonded to each other to form a ring,
R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl,
r1 and r3 are integers of 1 to 4, and when r1 and r2 are 2 or more, the structures in parentheses () are the same or different,
r4 is an integer from 0 to 4, and when r4 is 2 or more, R4 is the same or different,
r2 is an integer from 0 to 2. When r2 is 2, R2 is the same or different.
r41 and r42 are integers of 0 to 3, and when r41 and r42 are 2 or more, the structures in parentheses () are the same or different.

One embodiment of the present specification provides a photosensitive resin composition including the compound represented by the chemical formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

An embodiment of the present specification provides a photosensitive material manufactured 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.
[Effect of the invention]

The compound according to an embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, and can reduce the dispersing step due to its excellent solubility in organic solvents. In different cases, compounds can be used as coloring materials in economical methods.

In addition, the quinoline yellow-based compound represented by Chemical Formula 1 according to one embodiment of the present specification can be used as a coloring material, and color reproduction, brightness, and contrast ratio can be improved.

Hereinafter, this specification will be described in more detail.

In this specification, when a certain component is “on” another component, the case includes not only a case where a certain component is in contact with another component, but also a case where there are other components between the two components.

In this specification, when a certain element is "included" in a certain part, as long as there is no particularly contrary description, the above-mentioned situation means that other constituent elements may be further included, and other constituent elements are not excluded.

According to an aspect of the present specification, a compound represented by the chemical formula 1 is provided.

According to one embodiment of the present specification, the compound represented by Chemical Formula 1 has excellent solubility in an organic solvent. Specifically, solubility is increased by the chemical formula 1 containing phthalimide linked by an ester group (—COOR).

The bulky (Bulky) substituents prevent intermolecular agglomeration, and the solubility of the solvent is further increased by freely rotating substituents in the chromophore. In particular, substitutions such as phthalimide are based on dispersing pigments and are mostly used as synergists.

By increasing the solubility, aggregation between the coloring materials can be prevented, thereby reducing the amount of material required for dispersion of the coloring material, thereby improving economic efficiency. In addition, it can improve the contrast ratio (CR) and can have excellent heat resistance.

Examples of the substituents of the compound represented by the chemical formula 1 are described below, but the present invention is not limited thereto.

In this manual, It refers to a site bonded to another substituent or a bonding site.

In the present specification, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, nitrile, nitro, hydroxyl, carbonyl, ester, carboxy, imidate, amido, Anionic, alkoxy, alkyl, cycloalkyl, alkenyl, cycloalkenyl, sulfonate, amine, aryl, heteroaryl, silyl, alkylsulfonyloxy, arylsulfonate One or more substitutions in the group consisting of an acidic oxy group, a boron group, an acrylofluorenyl group, an acrylate group, an ether group, a heterocyclic group containing one or more N, O, S, or P atoms, and an anionic group Group, or does not have any substituents.

In the present specification, an "adjacent" group may refer to a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent closest to the position of the substituent on the stereostructure, or to the substituent. Other substituents substituted on a substituted atom. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

In the present specification, adjacent groups may be bonded to form a "ring". Therefore, the ring refers to an aromatic ring or an aliphatic ring. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. As the aryl group and the heteroaryl group, descriptions to be described later can be applied. In addition, the ring may be an aliphatic ring, and the aliphatic ring means a ring other than an aromatic ring.

Examples of the halogen group in this specification are: fluorine, chlorine, bromine or iodine.

In the present specification, the carbonyl group may be represented by -COR ', and the R' may be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted Substituted aryl. The carbon number of the carbonyl group is not particularly limited, but it is preferably one having 1 to 30 carbon numbers. Specifically, it may be a compound having a structure such as the following, but it is not limited thereto.

In the present specification, the ester group may be represented by -COOR '', and R '' may be hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or Substituted or unsubstituted aryl. In the ester group, the oxygen of the ester group may be substituted by a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, although it may be a compound of the following structural formula, it is not limited to this.

In this specification, the carbon number of a fluorene imino group is not specifically limited, It is preferable that it is a carbon number of 1-30. Specifically, it may be a compound having a structure such as the following, but it is not limited thereto.

In the present specification, in the amidino group, the nitrogen of the amidino group may be substituted by hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, although it may be a compound of the following structural formula, it is not limited to this.

In this specification, the anionic group has a chemical bond with the structure of Chemical Formula 1. The anionic group is not particularly limited. 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- Anions described in 111696, Japanese Patent Laid-Open No. 2008-249663, and Japanese Patent Laid-Open No. 2014-199436. Specific examples of the anionic group include trifluoromethanesulfonate anion, bis (trifluoromethylsulfonyl) sulfonium anion, bistrifluoromethanesulfonimide anion, and bisperfluoroethylsulfonimide anion. , tetraphenyl borate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tri - trifluoromethanesulfonic methide _{^{acyl, SO 3 -, CO 2 -}} , SO ₂ N ^- SO ₂ CF ₃ , SO ₂ N ^- SO ₂ CF ₂ CF ₃ , and a halogen group such as a fluoro group, an iodo group, and a chloro group are not limited thereto.

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

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

In the present specification, the alkoxy group may be a straight chain or a branched chain, and the number of carbons is not particularly limited, and may be 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an embodiment, the carbon number of the alkyl group is 1 to 30. According to another aspect, the carbon number of the alkyl group is 1-20. According to still another aspect, the carbon number of the alkyl group is 1-10. Specific examples of the alkyl group include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, third butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, etc. But it is not limited to these. In the present specification, the cycloalkyl group is not particularly limited, but preferably one having 3 to 30 carbon atoms. Particularly preferred are cyclopentyl and cyclohexyl, but they are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has a carbon number of 3 to 60. According to an embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3-20. According to still another aspect, the carbon number of the cycloalkyl group is 3 to 6. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl, but are not limited to these.

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbons is not particularly limited, but is preferably 2 to 60. According to an embodiment, the carbon number of the alkenyl group is 2-30. According to another aspect, the carbon number of the alkenyl group is 2-20. According to another aspect, the carbon number of the alkenyl group is 2-10. Specific examples of the alkenyl group are preferably an alkenyl group substituted with an aryl group such as a stylbenyl group and a styrenyl group, but are not limited thereto.

In the present specification, the cycloalkenyl group is not particularly limited, and it is preferably one having 3 to 60 carbon atoms. According to one embodiment, the cycloalkenyl group has 3 to 30 carbon atoms. According to another aspect, the carbon number of the cycloalkenyl group is 3-20. According to another embodiment, the number of carbon atoms of the cycloalkenyl group is 3-6. Examples of cycloalkenyl are preferably cyclopentenyl and cyclohexenyl, but they are not limited to these.

In this specification, the aryl group is not particularly limited, but preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an embodiment, the carbon number of the aryl group is 6-30. According to an embodiment, the carbon number of the aryl group is 6-20. Regarding the aryl group, the monocyclic aryl group may be a phenyl group, a biphenyl group, a bitriphenyl group, and the like, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthracenyl, indenyl, phenanthryl, fluorenyl, fluorenyl, triphenyl, But not limited to these.

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

In the case where the fluorenyl group is substituted, it may be Isospiro ring, (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and other substituted fluorenyl groups. However, it is not limited to this.

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, but it is 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of heterocyclic groups are: thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl, Pyridazinyl, quinolinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, diphenyl A benzothienyl group, a benzofuranyl group, a dibenzofuranyl group, etc. are not limited to these.

In this specification, as for the heteroaryl group, in addition to being aromatic, the description related to the heterocyclic group can be applied.

In this specification, a silane group may be represented by a chemical formula of -SiY1Y2Y3, and Y1, Y2, and Y3 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, respectively. Specifically, the silyl group includes: Trimethylsilyl (TMS), triethylsilyl, third butyldimethylsilyl, vinyldimethylsilyl, propyldimethyl Silyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like are not limited to these.

In the present specification, the alkylsulfonic acid group includes, but is not limited to, a methylsulfonic acid group, an ethylsulfonic acid group, a propylsulfonic acid group, and a butylsulfonic acid group. As the alkyl group in the alkylsulfonic acid oxy group, the description related to the alkyl group can be applied.

In this specification, an arylsulfonic acid group includes a benzenesulfonic acid group, a p-toluenesulfonic acid group, and the like, but is not limited to these. As the aryl group in the arylsulfonic acid group, a description related to the aryl group can be applied.

In this specification, a boron group may be represented by a chemical formula of -BY4Y5, and Y4 and Y5 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, respectively. Specifically, the boron group includes a trimethylboryl group, a triethylboryl group, a third butyldimethylboryl group, a triphenylboronyl group, a phenylboronyl group, and the like, but is not limited thereto. some.

In this specification, an acrylfluorenyl group means a photopolymerizable unsaturated group, For example, a (meth) acrylfluorenyl group is mentioned, It is not limited to this.

In this specification, an acrylate group means a photopolymerizable unsaturated group, For example, a (meth) acrylate group is mentioned, It is not limited to this.

In the present specification, "(meth) acrylfluorenyl" means at least one selected from the group consisting of acrylfluorenyl and methacrylfluorenyl. The expression "(meth) acrylate" has the same meaning.

In this specification, an ether group may be represented by -COR '' '. The R '' 'is a substituted or unsubstituted alkyl group. The description of the alkyl group can be applied to the alkyl group.

In the present specification, the sulfonate group may be an alkylsulfonate group, a cycloalkylsulfonate group, or an arylsulfonate group. The "alkyl" may apply a description related to the alkyl group, the "cycloalkyl" may apply a description related to the cycloalkyl group, and the "aryl" may apply a description related to the aryl group instruction of.

In the present specification, the sulfonate group may be represented by the following chemical formula S, but is not limited thereto.
[Chemical Formula S]

In the chemical formula S, A may be a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

In this specification, the amine group may be selected from the group consisting of -NH ₂ , alkylamino, N-alkylarylamino, arylamino, N-arylheteroarylamine, and N-alkylheteroarylamine. The number of carbon atoms in the group consisting of a group and a heteroarylamino group is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino group, dimethylamino group, ethylamino group, diethylamino group, phenylamino group, naphthylamino group, biphenylamino group, anthracenylamino group, 9-methyl-anthrylamido, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenyl Biphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthryl Amino group, N-phenylfluorenylamino group, N-phenylbitriphenylamino group, N-phenanthrylamino group, N-biphenylfluorenylamino group, etc., but it is not limited to these .

In this specification, the carbon number of the dianhydride group containing a nitrogen atom is not specifically limited, It may be 4-30, Specifically, it may be 4-20, More specifically, it may be 4-15.

In the present specification, the dianhydride group containing a nitrogen atom may be represented by the following chemical formula N or chemical formula M, but is not limited thereto.
[Chemical Formula N]



[Chemical Formula M]

In the chemical formula N and the chemical formula M, B is -X-X'- or -X = X'-, X and X 'are CR ₁₁ R ₁₂ , R ₁₁ and R ₁₂ are the same or different from each other, and are each independently hydrogen , Deuterium, N or S, or adjacent groups are bonded to each other to form a ring, and Z1 to Z3 are the same or different from each other, and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, or A substituted or unsubstituted aryl group, or an adjacent group may be bonded to each other to form a ring.

In this specification, the description of the substituted or unsubstituted divalent dianhydride group containing a nitrogen atom may be applied to the dianhydride group containing a nitrogen atom in addition to the divalent group.

In the present specification, an alkylene group refers to a group having two bonding positions on an alkane. The alkylene group may be linear, branched, or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, and is, for example, 1 to 30 carbon atoms, specifically 1 to 20 carbon atoms, and more specifically 1 to 10 carbon atoms.

In the present specification, a heteroalkyl group refers to an alkane containing O, N, or S as a hetero atom having two bonding positions. The heteroalkyl group may be linear, branched, or cyclic. The number of carbon atoms of the heteroalkyl group is not particularly limited, and is, for example, 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.

In the present specification, an arylene group refers to a divalent group having two bonding positions on the aryl group. With regard to these groups, in addition to the divalent groups, the description of the aryl group can be applied.

In the present specification, a heteroaryl group refers to a divalent group having two bonding positions on the heteroaryl group. With regard to these groups, in addition to the divalent groups, the description of the heteroaryl group can be applied.

In one embodiment of the present specification, X is O or NH.

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

In one embodiment of the present specification, X is NH.

In addition, in one embodiment of the present specification, L of the chemical formula 1 may be a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, or a substituted or unsubstituted carbon group having 2 to 30 carbon atoms. Heteroalkyl, substituted or unsubstituted arylene having 6 to 30 carbons, or substituted or unsubstituted arylene having 2 to 30 carbons.

In an embodiment of the present specification, L of Chemical Formula 1 may be a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, and a substituted or unsubstituted alkylene group having 2 to 20 carbon atoms. Group, substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or substituted or unsubstituted arylene group having 2 to 20 carbon atoms.

In one embodiment of the present specification, L of the chemical formula 1 is a substituted or unsubstituted linear or branched chain alkylene having 1 to 30 carbon atoms.

In one embodiment of the present specification, L of the chemical formula 1 is a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L of the chemical formula 1 is a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L in Chemical Formula 1 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L in Chemical Formula 1 is substituted or unsubstituted propylene.

In one embodiment of the present specification, L of the chemical formula 1 is propylene.

In addition, in an embodiment of the present specification, M of the chemical formula 1 is a direct bond, a substituted or unsubstituted alkylene group, a substituted or unsubstituted heteroalkylene group, a substituted or unsubstituted Substituted arylene, substituted or unsubstituted heteroaryl, or substituted or unsubstituted divalent dianhydride containing a nitrogen atom.

In one embodiment of the present specification, M in the chemical formula 1 is a direct bond or a substituted or unsubstituted divalent dianhydride group containing a nitrogen atom.

In one embodiment of the present specification, M of the chemical formula 1 is a direct bond.

In one embodiment of the present specification, M in Chemical Formula 1 is a substituted or unsubstituted divalent dianhydride group containing a nitrogen atom.

In one embodiment of the present specification, M in the chemical formula 1 is a divalent dianhydride group containing a nitrogen atom.

In one embodiment of the present specification, M of the chemical formula 1 may be represented by the following chemical formula.

In one embodiment of the present specification, M of the chemical formula 1 may be represented by the following chemical formula.

In one embodiment of the present specification, at least one of R1 and R3 of the chemical formula 1 is represented by the chemical formula 2 or the chemical formula 3.

In an embodiment of the present specification, R1 of the chemical formula 1 is represented by the chemical formula 2 or the chemical formula 3.

In one embodiment of the present specification, R1 of the chemical formula 1 is represented by the chemical formula 2.

In one embodiment of the present specification, R1 of the chemical formula 1 is represented by the chemical formula 3.

In addition, in one embodiment of the present specification, one of R1 in the chemical formula 1 is not the chemical formula 2 or the chemical formula 3 is selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, and -COR. , -COOR, amidino, amidino, anionic, sulfonic, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted ring Alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted In the group consisting of a substituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent R1 groups may be bonded to each other to form a ring. R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl.

In an embodiment of the present specification, not one of the chemical formula 2 or the chemical formula 3 in R1 of the chemical formula 1 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted Alkyl groups, or adjacent R1, may be bonded to each other to form a ring, and R is hydrogen, or a substituted or unsubstituted alkyl group.

In an embodiment of the present specification, not one of the chemical formula 2 or the chemical formula 3 in R1 of the chemical formula 1 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted The alkyl group having 1 to 30 carbon atoms or adjacent R1 may be bonded to each other to form an aromatic ring. The R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In an embodiment of the present specification, not one of the chemical formula 2 or the chemical formula 3 in R1 of the chemical formula 1 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted An alkyl group having 1 to 20 carbon atoms, or adjacent R1 groups may be bonded to each other to form an aromatic ring. The R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In an embodiment of the present specification, not one of the chemical formula 2 or the chemical formula 3 in R1 of the chemical formula 1 is hydrogen, a halogen group, a nitro group, a hydroxyl group, -COOR, or a substituted or unsubstituted The alkyl group having 1 to 10 carbon atoms or adjacent R1 may be bonded to each other to form an aromatic ring. The R is hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In an embodiment of the present specification, in the R1 of the chemical formula 1, not the chemical formula 2 or the chemical formula 3 is hydrogen, F, Cl, Br, nitro, hydroxyl, -COOR, or substituted or unsubstituted. A substituted third butyl or adjacent R1 may be bonded to each other to form a substituted or unsubstituted benzene ring, wherein R is hydrogen, or a substituted or unsubstituted methyl group.

In an embodiment of the present specification, the one of R1 in the chemical formula 1 other than the chemical formula 2 or the chemical formula 3 is hydrogen, F, Cl, Br, nitro, hydroxyl, -COOR, or third butyl. Or, adjacent R1s may be bonded to each other to form a halogen group, a nitro group, or a benzene ring substituted or unsubstituted with a sulfonic group. The R is hydrogen or methyl.

In an embodiment of the present specification, the one of R1 in the chemical formula 1 other than the chemical formula 2 or the chemical formula 3 is hydrogen, F, Cl, Br, nitro, hydroxyl, -COOR, or third butyl. Or, adjacent R1s may be bonded to each other to form Br, a nitro group, or a benzene ring substituted or unsubstituted by a sulfonic group, wherein R is hydrogen or methyl.

In addition, in an embodiment of the present specification, the R2 is selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, -COR, -COOR, fluorenimine, fluorenamine, and anionic group. , Sulfonate, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or Unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl And a group consisting of a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent R1s may be bonded to each other to form a ring, and the R is hydrogen, deuterium, substituted or unsubstituted alkane Radical, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl.

In an embodiment of the present specification, the R2 is hydrogen or deuterium.

In one embodiment of the present specification, R 2 is hydrogen.

In addition, in an embodiment of the present specification, R3 of the chemical formula 1 is represented by the chemical formula 2 or the chemical formula 3.

In an embodiment of the present specification, R3 of the chemical formula 1 is represented by a chemical formula 2.

In an embodiment of the present specification, R3 of the chemical formula 1 is represented by the chemical formula 3.

In addition, in one embodiment of the present specification, one of R3 in the chemical formula 1 is not the chemical formula 2 or the chemical formula 3 is selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, and -COR. , -COOR, amidino, amidino, anionic, sulfonic, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted ring Alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted In the group consisting of a substituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent R1 groups may be bonded to each other to form a ring.
The R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl.

In an embodiment of the present specification, one of the R3 of the chemical formula 1 other than the chemical formula 2 or the chemical formula 3 is hydrogen, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted An aryl group, a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form a ring.

In an embodiment of the present specification, one of the R3 of the chemical formula 1 other than the chemical formula 2 or the chemical formula 3 is hydrogen, a substituted or unsubstituted sulfonate group, a substituted or unsubstituted An aryl group, a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form a ring.

In one embodiment of the present specification, R3 in Chemical Formula 1 is not the Chemical Formula 2 or the Chemical Formula 3 is hydrogen, a substituted or unsubstituted arylsulfonate group having 6 to 30 carbon atoms. A substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a dianhydride group containing a nitrogen atom, or adjacent R3 groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, R3 in Chemical Formula 1 is not the Chemical Formula 2 or the Chemical Formula 3 is hydrogen, a substituted or unsubstituted arylsulfonate group having 6 to 20 carbon atoms. A substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a dianhydride group containing a nitrogen atom, or adjacent R3 groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, R3 in Chemical Formula 1 is not the Chemical Formula 2 or the Chemical Formula 3 is hydrogen, a substituted or unsubstituted arylsulfonate group having 6 to 10 carbon atoms. , Phenyl, or a dianhydride group containing a nitrogen atom, or adjacent R3 may be bonded to each other to form a benzene ring or a pyridine ring.

In one embodiment of the present specification, not one of the chemical formula 2 or the chemical formula 3 in R3 of the chemical formula 1 is hydrogen.

In an embodiment of the present specification, in R3 of Chemical Formula 1, not the Chemical Formula 2 or the Chemical Formula 3 is a substituted or unsubstituted arylsulfonate group, and the substituted or unsubstituted The substituted arylsulfonate group may be represented by the following Chemical Formula S.
[Chemical Formula S]

In the chemical formula S, A is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, A of the chemical formula S is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, A of the chemical formula S is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A of the chemical formula S is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In an embodiment of the present specification, A of the chemical formula S is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, A of the chemical formula S is a phenyl group or a naphthyl group.

In one embodiment of the present specification, the chemical formula S may be represented by any one of the following chemical formulas.

In one embodiment of the present specification, not one of the chemical formula 2 or the chemical formula 3 in the R3 of the chemical formula 1 is a phenyl group.

In an embodiment of the present specification, one of R3 in Chemical Formula 1 other than the Chemical Formula 2 or the Chemical Formula 3 is a dianhydride group containing a nitrogen atom, and the dianhydride group containing a nitrogen atom may be represented by the following chemical formula N or the following chemical formula M.
[Chemical Formula N]



[Chemical Formula M]

In the chemical formula N and the chemical formula M, B is -X-X'- or -X = X'-, X and X 'are CR ₁₁ R ₁₂ , R ₁₁ and R ₁₂ are the same or different from each other, and are each independently hydrogen , Deuterium, N or S, or adjacent groups are bonded to each other to form a ring, and Z1 to Z3 are the same or different from each other, and are independently hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, A substituted or unsubstituted aryl group, or an adjacent group may be bonded to each other to form a ring.

In an embodiment of the present specification, B of the chemical formula N is -X-X'- or -X = X'-, X and X 'are CR ₁₁ R ₁₂ , R ₁₁ and R ₁₂ are the same or different from each other, Each is independently hydrogen, deuterium, N or S, or adjacent groups may be bonded to each other to form an aliphatic ring or an aromatic ring.

In an embodiment of the present specification, Z1 to Z3 of the chemical formula M are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Alternatively, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 to Z3 of the chemical formula M are the same or different from each other, and are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, Alternatively, substituted or unsubstituted aryl groups having 6 to 20 carbon atoms, or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, Z1 to Z3 of the chemical formula M may be independently bonded to adjacent groups to form an aromatic ring.

In an embodiment of the present specification, Z1 and Z2 of the chemical formula M may be bonded to each other to form an aromatic ring, and Z2 and Z3 may be bonded to each other to form an aromatic ring.

In an embodiment of the present specification, Z1 and Z2 of the chemical formula M may be bonded to each other to form a substituted or unsubstituted benzene ring, and Z2 and Z3 may be bonded to each other to form a substituted or unsubstituted benzene. ring.

In an embodiment of the present specification, Z1 and Z2 of the chemical formula M may be bonded to each other to form a benzene ring, and Z2 and Z3 may be bonded to each other to form a benzene ring.

In one embodiment of the present specification, the chemical formula N may be represented by any one of the following chemical formulas.

In the chemical formula, N1 to N18 are the same or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxyl group, -COR, -COOR, amidino group, amidino group, anion Sex group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted Substituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and In a group of substituted or unsubstituted dianhydride groups containing a nitrogen atom, adjacent groups may be bonded to each other to form a ring.
R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl,
n1 is an integer from 0 to 4, n2 is an integer from 0 to 2, n3 is an integer from 0 to 4, n8 is an integer from 0 to 8, n9 is an integer from 0 to 4, n10 is an integer from 0 to 4, and n11 is An integer from 0 to 2, n12 is an integer from 0 to 5, n13 is an integer from 0 to 2, n14 is an integer from 0 to 2, n15 is an integer from 0 to 4, n16 is an integer from 0 to 4, and n17 is an integer from 0 to 4. An integer of 3, n18 is an integer of 0 to 3,
When n1 to n18 are 2 or more, the structures in parentheses () are the same or different.

In one embodiment of the present specification, the N1 to N18 are hydrogen.

In one embodiment of the present specification, the chemical formula M may be represented by the following chemical formula M-1.
[Chemical Formula M-1]

In the chemical formula M-1, N19 and N20 are the same or different from each other, and are each independently selected from the group consisting of hydrogen, deuterium, halogen group, nitrile group, nitro group, hydroxyl group, -COR, -COOR, fluorenimine, and sulfonamide Group, anionic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkenyl group, substituted Or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl In the group consisting of a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent groups may be bonded to each other to form a ring,
R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl,
n19 and n20 are the same or different from each other, and are each independently an integer of 0 to 3. When n19 and n20 are 2 or more, the structures in parentheses () are the same or different.

In one embodiment of the present specification, N19 and N20 of the chemical formula M-1 are hydrogen.

In addition, in one embodiment of the present specification, the R4 is selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, -COR, -COOR, fluorenimine, fluorenamine, and anionic group. , Substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted Cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and substituted or In a group consisting of an unsubstituted dianhydride group containing a nitrogen atom, adjacent groups may be bonded to each other to form a ring.
The R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl.

In one embodiment of the present specification, R4 is hydrogen, or adjacent groups may be bonded to each other to form a ring.

In one embodiment of the present specification, R4 is hydrogen, or adjacent groups may be bonded to each other to form an aromatic ring.

In one embodiment of the present specification, R 4 is hydrogen, or adjacent groups may be bonded to each other to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, R4 is hydrogen, or adjacent groups may be bonded to each other to form a benzene ring.

In addition, in an embodiment of the present specification, the R41 and R42 are the same as or different from each other, and are independently selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, -COR, -COOR, and fluorene. Amino, amido, anionic, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted Alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, substituted or unsubstituted aryl, substituted or unsubstituted In the group consisting of a substituted heteroaryl group and a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent groups may be bonded to each other to form a ring,
The R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl.

In one embodiment of the present specification, R41 and R42 are hydrogen.

In one aspect of the present specification, r1 is an integer of 1 to 4.

In an embodiment of the present specification, r2 is an integer of 0 to 2.

In an embodiment of the present specification, r3 is an integer of 1 to 4.

In an embodiment of the present specification, r4 is an integer of 0 to 4.

In an embodiment of the present specification, the chemical formula 1 may be represented by the following structure, the following structure represents an isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. The so-called isomers are molecules having the same molecular formula but different physical / chemical properties from each other.

In the structure, R1 to R3 and r1 to r3 depend on the content.

The descriptions related to the isomers can be applied to all chemical formulas described in this specification.

According to another aspect of the present specification, the chemical formula 1 may be represented by the following chemical formula 4 or chemical formula 5.
[Chemical Formula 4]



[Chemical Formula 5]

In the chemical formula 4 and the chemical formula 5,
R2 to R4, R41, R42, L, M, r2 to r4, r41 and r42 are as defined in the chemical formula 1,
R5 is selected from the group consisting of hydrogen, deuterium, halo, nitrile, nitro, hydroxyl, -COR, -COOR, fluorenimine, fluorenimine, anionic group, substituted or unsubstituted alkoxy group, Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonic acid Ester groups, substituted or unsubstituted amine groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups,
R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl,
r5 is an integer of 0 to 3, and when r5 is 2 or more, R5 are the same or different from each other.

In this specification, R5 is hydrogen or deuterium.

In this specification, R5 is hydrogen.

According to another aspect of the present specification, the chemical formula 1 may be represented by the following chemical formula 6 or chemical formula 7.
[Chemical Formula 6]



[Chemical Formula 7]

In the chemical formula 6 and the chemical formula 7,
R1, R2, R4, R41, R42, L, M, r1, r2, r4, r41 and r42 are as defined in the chemical formula 1,
R6 is selected from the group consisting of hydrogen, deuterium, halo, nitrile, nitro, hydroxy, -COR, -COOR, fluorenimine, fluorenimine, anionic, substituted or unsubstituted alkoxy, Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonic acid Ester groups, substituted or unsubstituted amine groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heteroaryl groups,
R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl,
r6 is an integer of 0 to 3, and when r6 is 2 or more, R6 are the same or different from each other.

In this specification, R6 is hydrogen or deuterium.

In this specification, R6 is hydrogen.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 4-1 or chemical formula 5-1.
[Chemical Formula 4-1]



[Chemical Formula 5-1]

In the chemical formula 4-1 and the chemical formula 5-1,
R2 to R5, R41, R42, L, M, r2 to r5, r41, and r42 are as defined in Chemical Formula 4 and Chemical Formula 5.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 6-1 or chemical formula 7-1.
[Chemical Formula 6-1]



[Chemical Formula 7-1]

In the chemical formula 6-1 and the chemical formula 7-1,
R1, R2, R4, R6, R41, R42, L, M, r1, r2, r4, r6, r41, and r42 are as defined in the chemical formula 6 and the chemical formula 7.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-1.
[Chemical Formula 1-1]

In the chemical formula 1-1,
R1 to R3, r1 and r2 are as defined in the chemical formula 1,
R31 is hydrogen, deuterium, a substituted or unsubstituted sulfonate group, or a substituted or unsubstituted dianhydride group containing a nitrogen atom,
r3-1 is an integer of 0 to 3, and when r3-1 is 2 or more, R3 is the same or different.

In R31 of the chemical formula 1-1, the substituted or unsubstituted sulfonate group and the substituted or unsubstituted dianhydride group containing a nitrogen atom depend on the contents described above.

In an embodiment of the present specification, at least one of R3 may be represented by hydrogen, the following chemical formula S, chemical formula N, or chemical formula M.
[Chemical Formula S]



[Chemical Formula N]



[Chemical Formula M]

In the chemical formula S, chemical formula N and chemical formula M, Indicates a part connected to the chemical formula 1,
A is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group,
B is -X-X'- or -X = X'-,
X and X 'are CR ₁₁ R ₁₂ ,
R ₁₁ and R ₁₂ are the same or different from each other, and are each independently hydrogen, deuterium, N or S, or adjacent groups are bonded to each other to form a ring,
Z1 to Z3 are the same or different from each other, and are each independently hydrogen, deuterium, halo, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or adjacent groups may be bonded to each other. Form a ring.

In the chemical formula S, chemical formula N, and chemical formula M, A, B, and Z1 to Z3 depend on the contents described above.

According to another aspect of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas, but is not necessarily limited thereto.

Moreover, one aspect of this specification provides the coloring material composition containing the compound represented by the said chemical formula 1.

The coloring material composition may include at least one of a dye and a pigment in addition to the compound of Chemical Formula 1. For example, the coloring material composition may include only the compound of Chemical Formula 1, or the compound of Chemical Formula 1 and one or more dyes, or the compound of Chemical Formula 1 and one or more pigments, or The compound of Chemical Formula 1, one or more dyes, and one or more pigments are described.

One embodiment of the present specification provides a photosensitive resin composition including the coloring material composition.

One embodiment of the present specification provides a photosensitive resin composition including the compound represented by the chemical formula 1, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent.

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

The binder resin may be a copolymerized resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, and may further include a binder commonly used in the technical field.

The polyfunctional monomer that imparts mechanical strength to the film may be any one or more of unsaturated carboxylic acid esters, aromatic vinyls, unsaturated ethers, unsaturated sulfonimines, and acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters can 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, tertiary butyl (meth) acrylate, cyclohexyl (meth) acrylate, (meth) Isobornyl acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, (formyl) ) -2-hydroxypropyl acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, fluorenyl octyloxy (meth) acrylate- 2-hydroxypropyl ester, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy diethylene glycol Alcohol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, benzene Oxydiethylene glycol (meth) acrylate, p-nonylphenoxy Polyethylene glycol (meth) acrylate, p-nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, (meth) acrylic acid -1,1,1,3,3,3-hexafluoroisopropyl ester, octafluoropentyl (meth) acrylate, heptafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, α-Hydroxymethacrylate, α-Hydroxymethacrylate, α-Hydroxymethacrylate, and α-Hydroxymethacrylate are not limited to these.

Specific examples of the aromatic vinyls include free styrene, α-methylstyrene, (o-, m-, p-)-vinyltoluene, (o-, m-, p-)-methoxystyrene, and ( The group consisting of ortho, meta, and para) -chlorostyrene is not limited to these.

Specific examples of the unsaturated ethers may be selected from the group consisting of vinyl methyl ether, vinyl ether, and allyl glycidyl ether, but are not limited to these.

Specific examples of the unsaturated fluorene imines can be selected from N-phenylcis butylene diimide, N- (4-chlorophenyl) cis butylene diimide, and N- (4-hydroxybenzene Group), but is not limited to this group consisting of cis-butene diimide and N-cyclohexyl cis-butene diimide.

The acid anhydride includes maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride, and the like, but is not limited to these.

The monomer for imparting alkali solubility is not particularly limited as long as it contains an acid group. For example, it is preferable to use a monomer selected from (meth) acrylic acid, butenoic acid, itaconic acid, maleic acid, and fumaric acid. Diacid, monomethylmaleic acid, 5-norbornene-2-carboxylic acid, phthalic acid mono-2-((meth) acrylfluorenyloxy) ethyl ester, succinic acid mono- One or more members of the group consisting of 2-((meth) acrylfluorenyloxy) ethyl ester and ω-carboxy polycaprolactone mono (meth) acrylate are not limited thereto.

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

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

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

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

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

The photoinitiator is not particularly limited as long as it is an initiator that generates free radicals to promote cross-linking. For example, the photoinitiator may be selected from acetophenone-based compounds, biimidazole-based compounds, and triazine-based compounds. And one or more of the group consisting of oxime-based compounds.

The acetophenone-based compounds include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane- 1-ketone, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ether, benzoin isobutyl ether , Benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholinyl-1-propane-1-one 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butane-1-one, 2- (4-bromo-benzyl-2-dimethylamino) 1- (4-morpholinylphenyl) -butane-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinylpropane-1-one, etc. Is not limited to these.

The biimidazole-based compounds include: 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl)- 4,4 ', 5,5'-tetra (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. Is not limited to these.

The triazine-based compound includes: 3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 1,1,1,3,3 , 3-hexafluoroisopropyl-3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl-2- {4 -[2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis ( Trichloromethyl) -mesytriazin-6-yl] phenylthio} acetate, cyclohexyl-2- {4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl ] Benzylthio} acetate, benzyl-2- {4- [2,4-bis (trichloromethyl) -mesatriazin-6-yl] phenylthio} acetate, 3- {chloro -4- [2,4-bis (trichloromethyl) -mesytriazin-6-yl] phenylthio} propanoic acid, 3- {4- [2,4-bis (trichloromethyl) -isocyanate Triazin-6-yl] phenylthio} propanamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) ) -6- (1-p-dimethylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxybenzene Vinyl-mesytriazine and the like are not limited to these.

The oxime-based compounds are: 1,2-octanedione, 1- (4-phenylthio) phenyl, 2- (o-benzoylhydrazine) (Ciba-Geigy) Company, CGI124), ethyl ketone, -1- (9-ethyl) -6- (2-methylbenzylidene-3-yl)-, 1- (O-acetamidooxime) (CGI242), N-1919 (ADEKA) is not limited to these.

In an embodiment of the present specification, the photo-initiator may be I-369 (BASF).

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 ethyl 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, tertiary butanol, 2-ethoxypropanol, 2-methyl Oxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, propylene glycol ether acetate, 3-methoxybutyl acetate, 3-ethoxy Ethyl propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether are not limited thereto.

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

An embodiment of the present specification provides a photosensitive resin composition, wherein a content of the compound represented by the chemical formula 1 is 5 to 60% by weight based on a total weight of the photosensitive resin composition. The content of the binder resin is 1% to 60% by weight, the content of the photoinitiator is 0.1% to 20% by weight, and the content of the polyfunctional monomer is 0.1% to 50% by weight. The content of the additive is 0.1% to 10% by weight, and the content of the solvent is 10% to 80% by weight.

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

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

According to an embodiment of the present specification, the photosensitive resin composition may further include an additive.

According to an embodiment of the present specification, the photosensitive resin composition may further include a member selected from the group consisting of a photocrosslinking sensitizer, a hardening accelerator, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, One or two or more additives in a group consisting of a dispersant and a leveling agent.

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

In one aspect of the present specification, the additive may be a surfactant.

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

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

As the photocrosslinking sensitizer, one or more members selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4- Bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl benzoate, 3,3-dimethyl- Benzophenone compounds such as 4-methoxybenzophenone, 3,3,4,4-tetrakis (third butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9 -Fluorenone compounds such as fluorenone, 2-methyl-9-fluorenone; thioanthrone, 2,4-diethylthioxanthone, 2-chlorothiaxanthone, 1-chloro-4- Thioxanthone-based compounds such as propyloxythioxanthone, isopropylthioxanthone, and diisopropylthioxanthone; xanthracenes such as xanthone and 2-methylxanthone Ketone compounds; anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, third butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone and other anthraquinone compounds; 9-benzene Acridine, 1,7-bis (9-acridyl) heptane, 1,5-bis (9-acridylpentane), 1,3-bis (9-acridyl) propane, and other acridines Compounds; benzoin, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrene And other dicarbonyl compounds; 2,4,6-trimethylbenzylidenediphenylphosphine oxide, bis (2,6-dimethoxybenzylidene) -2,4,4-trimethylpentane Phosphine oxide compounds such as phosphine oxide; methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl Benzoate compounds such as methyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzylidene) cyclopentanone, 2,6-bis ( 4-diethylaminobenzylidene) cyclohexanone, 2,6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone and other amine synergists; 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzylidene- 7- (diethylamino) coumarin, 3-benzylidene-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2 , 3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinazin-11-one and other coumarin compounds; 4-di Chalcone compounds such as ethylaminochalcone, 4-azidobenzylideneacetophenone; 2-benzylidenemethylene, 3-methyl-b-naphthothiazoline.

The hardening accelerator is used to improve hardening and mechanical strength. Specifically, one or more members selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, and 2 -Mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate) , Pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tris (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate) Esters) and trimethylolpropane-tris (3-mercaptopropionate).

The adhesion promoter used in this specification may be selected from methacrylfluorenyloxypropyltrimethoxysilane, methacrylfluorenyloxypropyldimethoxysilane, and methacrylfluorenyloxypropyl One or more of methacrylfluorenylsilane coupling agents such as triethoxysilane, methacrylmethyloxypropyldimethoxysilane, and the like can be used. The alkyltrimethoxysilane can be obtained from octyltrimethoxysilane. , Dodecyltrimethoxysilane, octadecyltrimethoxysilane, etc., one or more are selected and used.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant can be used: BYK-077, BYK-085, 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: F-114, F-177, F-410, F-411, F-411 from Dainippon Ink & Chemicals (DIC) 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 it is not limited to these .

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

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 phosphoric acid-based thermal stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; 2,6-di-third-butyl-p-cresol, and octadecane 3- (4-hydroxy-3,5-di-tert-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-tert-butyl-4-hydroxy) Phenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-third-butyl-4-hydroxybenzyl) benzene, 3,5- Diethyl tertiary butyl-4-hydroxybenzyl phosphite, 2,2-thiobis (4-methyl-6-third butylphenol), 2,6-g, t-butyl Phenol 4,4'-butylene-bis (3-methyl-6-third butylphenol), 4,4'-thiobis (3-methyl-6-third butylphenol) or bis [ 3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) Hindered phenol such as butanoicacid] glycol ester) is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine Or N, N'-di-β-naphthyl-p-phenylenediamine, such as amine secondary antioxidants; dilauryl disulfide, dilauryl thiopropionate, distearyl thio Thio (Thio) secondary antioxidants such as esters, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or three Phenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) ) Pentaerythritol Diphosphite) or (1,1'-biphenyl) -4,4'-diylbisphosphonic acid tetra [2,4-bis (1,1-dimethylethyl) phenyl] ester (( Phosphite-based secondary antioxidants such as 1,1'-Biphenyl) -4,4'-Diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

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

The thermal polymerization inhibitor may include, for example, one or more members 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-third-butyl-p-cresol, o-benzene Triphenol, benzoquinone, 4,4-thiobis (3-methyl-6-third butylphenol), 2,2-methylenebis (4-methyl-6-third butylphenol) , 2-mercaptoimidazole, and phenothiazine, but are not limited to these, and may include those generally known in the technical field.

The dispersant may be used in a method of internally adding to the pigment or a method of externally adding to the pigment in a state where the pigment is surface-treated in advance. The dispersant may be a compound-type, nonionic, anionic or cationic dispersant, and examples thereof include fluorine-based, ester-based, cationic, anionic, non-ionic, and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, the dispersant is selected from the group consisting of polyalkylene glycols and their esters, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonate esters, and sulfonate salts. One or more of the group consisting of carboxylic acid esters, carboxylic acid salts, alkylamidoalkylene oxide adducts, and alkylamines, but is not limited thereto.

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

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

In more detail, the photosensitive resin composition of this specification can be apply | coated to a base material and hardened by an appropriate method, and a photosensitive material in the form of a film or a pattern can be manufactured.

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 generally widely used. In addition, after forming the coating film, a part of the residual solvent can be removed under reduced pressure as appropriate.

The light source for curing the photosensitive resin composition of the present specification includes, for example, mercury vapor arcs (arc), carbon arcs, Xe arcs, and the like that emit light having a wavelength of 250 nm to 450 nm, but it is not necessarily limited to these.

The photosensitive resin composition of this specification can be used in a thin film transistor-liquid crystal display (TFT LCD) color filter manufacturing pigment dispersion type photosensitive material, and a thin-film transistor liquid crystal display (TFT LCD). Photosensitive material for black matrix or organic light emitting diode, Photosensitive material for overcoat layer formation, Columnar spacer photosensitive material, Photocurable paint, Photocurable ink, Photocurable adhesive, Printing plate, Printing Among the photosensitive materials for wiring boards, and photosensitive materials for plasma display panels (PDP), the use thereof is not particularly limited.

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

The color filter can be produced using a photosensitive resin composition containing the compound represented by the chemical formula 1. The photosensitive resin composition is coated on a substrate to form a coating film, and the coating film is exposed, developed, and cured to produce a photosensitive material, and a color filter including the photosensitive material can be provided. sheet.

The photosensitive resin composition according to an embodiment of the present specification is excellent in heat resistance and has little color change due to heat treatment. When manufacturing a color filter, it can provide high color reproducibility, brightness, and contrast when using a hardening process. High color filter.

The substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (Polycarbonate, PC), and the like, and the type thereof is not particularly limited.

Specifically, the photosensitive resin composition according to an embodiment of the present specification may be spin-coated on glass (5 × 5 cm ² ) and subjected to prebake at 100 ° C. for 100 seconds to form a film. . The interval between the film-formed substrate and a photo mask was set to 250 um, and the entire surface of the substrate was irradiated with an exposure device at an exposure amount of 40 mJ / cm ² . Thereafter, the exposed substrate may be developed in a developing solution (potassium hydroxide (KOH), 0.05%) for 60 seconds, and subjected to postbake at 230 ° C for 20 minutes to prepare a substrate.

The heat resistance evaluation can be measured by a method described later. With respect to the substrate manufactured by the above-mentioned one aspect, a spectroscope was used to obtain a transmittance spectrum in a visible light range of 380 nm to 780 nm. In addition, a prebake substrate was additionally subjected to postbake for 20 minutes at 230 ° C, and transmittance spectra were obtained with the same equipment and measurement range.

The spectroscope may be a MCPD-Otsuka company, but is not limited thereto.

The obtained transmittance spectrum and the C light source backlight are used, and the obtained values E (L *, a *, b *) are used to calculate a color change (hereinafter ΔEab). A small ΔEab value indicates excellent color heat resistance. If it has a value of ΔEab <3, it can be used as a pigment for a color filter, and can be called a coloring material having excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.
[Calculation formula 1]

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

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

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

Between the color pixels of the color filter, a grid-like black pattern called a black matrix can be arranged for the purpose of improving contrast. The material of the black matrix can use chromium. In this case, a method can be used in which chromium is deposited on the entire glass substrate and a pattern is formed by an etching process. However, in consideration of the high cost of the steps, 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 fine processing can be used.

The black matrix may use a black pigment or a black dye as a coloring material. For example, carbon black can be used alone, or carbon black can be mixed with colored pigments. At this time, because colored pigments with insufficient light-shielding properties are mixed, it has the following advantages: Even if the amount of coloring material is relatively increased, the strength of the film or the substrate The adhesion is not reduced.

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

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

In the following, specific examples will be described for detailed description of the present specification. However, the embodiments of this specification can be modified into various forms, and the scope of this specification is not to be construed as being limited to the embodiments described below. The embodiments of the present specification are provided to explain to the person skilled in the art a more complete description of the present specification.

<Example>
<Synthesis Example of Colorant Compound>
Synthesis Example 1: Synthesis of Compound 1

In a 100 ml 2-neck-round bottom flask (Round Bottom Flask, RBF), 25 g of methyl benzoate (Methylbenzoate) and 2 g (12.642 mmol) of A-1, 1.873 g ( 12.642 mmol) of B-1 and stirred. Specifically, the reaction was carried out at 180 ° C for 12 hours.

Thereafter, 2.429 g (12.642 mmol) of D-1 was added, and an additional reaction was performed at 180 ° C for 12 hours. The resultant was cooled to normal temperature and precipitated in 250 g of methanol (MeOH). After stirring for 30 minutes, the precipitate was filtered under reduced pressure, and then dried in a vacuum oven at 80 ° C. to obtain Compound 1, and the next reaction was performed without additional separation.

In a 250 ml 2-neck-round bottom flask (Round Bottom Flask (RBF)), put 80 g of Dimethylformamide (DMF) and 5 g (10.813 mmol) of Intermediate 1.2.725 g (30.439 mmol) of sodium bicarbonate (NaHCO ₃ ) was heated to 50 ° C. and stirred to prepare a reaction solution.

Thereafter, 2.899 g (10.813 mmol) of E-1 was slowly added to the reaction solution, and the mixture was stirred at 120 ° C for 4 hours. After that, the reaction solution was cooled to normal temperature and precipitated in 1800 ml of distilled water (DI-Water). After the precipitation, the precipitate was filtered under reduced pressure and washed with water. The precipitate was dried under reduced pressure. 5.2 g (8.010 mmol) of compound 1 were obtained.
Ionization mode Atmospheric Pressure Chemical Ionization (APCI) +: m / z = 650 [M + H], Exact Mass: 649

Synthesis Example 2: Synthesis of Compound 2

A 250 ml 2-neck-round bottom flask (Round Bottom Flask, RBF) was placed with 100 ml of 6 M hydrochloric acid (HCl), and then 9.135 g (66.61 mmol) of A-2, The temperature was raised to 100 ° C. and stirred for 30 minutes to prepare a reaction solution 1. Thereafter, 9.34 g (133.21 mmol) of A-3 was slowly added to the reaction solution 1.

Then, it stirred at 100 degreeC for 2 hours. Then, the reaction solution was cooled to normal temperature, and the precipitate was filtered under reduced pressure. The precipitate was recrystallized using 250 ml of ethanol (EtOH). Thereafter, filtration was performed under reduced pressure to obtain 7.3 g (38.995 mmol) of A-4.

Then, 25 g of methyl benzoate (Methylbenzoate), 2.366 g (12.642 mmol) of A-4, and 1.873 g (12.642 mmol) of B-1 were added and stirred. Specifically, reaction was performed at 180 ° C. for 12 hours to produce a reaction solution 2.

Thereafter, the reaction solution 2 was cooled to normal temperature and precipitated in 250 g of MeOH. After stirring for 30 minutes, the precipitate was filtered under reduced pressure, and then dried in a vacuum oven at 80 ° C. to obtain Intermediate 2, and the next reaction was performed without additional separation.

In a 250 ml 2-neck-round bottom flask (Round Bottom Flask, RBF), put 80 g of Dimethylformamide (DMF), and put 3.431 g (10.813 mmol) of Intermediate 2 and 2.725 g (30.439 mmol) of sodium bicarbonate (NaHCO ₃ ) were heated to 50 ° C. and stirred to prepare a reaction solution 3.

Then, 2.899 g (10.813 mmol) of E-1 was slowly added to the reaction solution 3, and it stirred at 120 degreeC for 4 hours. The stirred solution was cooled to normal temperature and precipitated in 1800 ml of distilled water (DI-Water). The precipitate was filtered under reduced pressure and washed with water, and then the precipitate was dried under reduced pressure to obtain 3.577 g (7.090 mmol) of Compound 2.
Ionization mode APCI +: m / z = 505 [M + H], Exact Mass: 504

Synthesis Example 3: Synthesis of Compound 3

Add 25 g of Methylbenzoate, 2.366 g (12.642 mmol) of A-5, 1.873 g (12.642 mmol) of B-1, and stir. The reaction was performed at 180 ° C for 12 hours to prepare a reaction solution 1.

Thereafter, the reaction solution 1 was cooled to normal temperature, and precipitated in 250 g of methanol (MeOH). After stirring for 30 minutes, the precipitate was filtered under reduced pressure, and then dried in a vacuum oven at 80 ° C. to obtain Intermediate 2, and the next reaction was performed without additional separation.

In a 250 ml 2-neck-round bottom flask (Round Bottom Flask, RBF), put 80 g of Dimethylformamide (DMF), and put 3.431 g (10.813 mmol) of Intermediate 3 and 2.725 g (30.439 mmol) of sodium bicarbonate (NaHCO ₃ ) were heated to 50 ° C. and stirred to prepare a reaction solution 2.

Thereafter, 2.899 g (10.813 mmol) of E-1 was slowly added to the reaction solution 2 and stirred at 120 ° C for 4 hours. After stirring, cool to normal temperature (25 ° C) and precipitate in 1800 ml of distilled water (DI-Water). The precipitate was filtered under reduced pressure and washed with water. The precipitate was dried under reduced pressure to obtain 3.592 g (7.120 mmol) of Compound 3.
Ionization mode APCI +: m / z = 505 [M + H], Exact Mass: 504

Synthesis Example 4: Synthesis of Compound 4

In a 100 ml 2-neck-round bottom flask (Round Bottom Flask, RBF), 25 g of methyl benzoate (Methylbenzoate), 2.443 g (12.642 mmol) of A-6, 2.429 g ( 12.642 mmol) of D-1 was reacted at 180 ° C for 12 hours.

The resultant was cooled to normal temperature and precipitated in 250 g of methanol (MeOH). After stirring for 30 minutes, the precipitate was filtered under reduced pressure, and dried in a vacuum oven at 80 ° C. to obtain Intermediate 4, and the next reaction was performed without additional separation.

In a 250 ml 2-neck-round bottom flask (Round Bottom Flask, RBF), put 80 g of Dimethylformamide (DMF), and put 3.972 g (10.813 mmol) of Intermediate 4. 2.725 g (30.439 mmol) of sodium bicarbonate (NaHCO ₃ ) was heated to 50 ° C. and stirred.

Thereafter, 2.899 g (10.813 mmol) of E-1 was slowly added to the reaction solution, and stirred at 120 ° C for 4 hours. The reaction solution was cooled to normal temperature and precipitated in 1800 ml of distilled water (DI-Water). The precipitate was filtered under reduced pressure, washed with water, and dried under reduced pressure to obtain 5.127 g (9.245 mmol) of Compound 4.
Ionization mode APCI +: m / z = 555 [M + H], Exact Mass: 554

Synthesis Example 5: Synthesis of Compound 5

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 5, and Compound 5 was synthesized by the same method.
Ionization mode APCI +: m / z = 700 [M + H], Exact Mass: 699

Synthesis Example 6: Synthesis of Compound 6

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 6, and Compound 6 was synthesized by the same method.
Ionization mode APCI +: m / z = 600 [M + H], Exact Mass: 599

Synthesis Example 7: Synthesis of Compound 7

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 7, and Compound 7 was synthesized by the same method.
Ionization mode APCI +: m / z = 556 [M + H], Exact Mass: 555

Synthesis Example 8: Synthesis of Compound 8

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 8 and Compound 8 was synthesized by the same method.
Ionization mode APCI +: m / z = 654 [M + H], Exact Mass: 653

Synthesis Example 9: Synthesis of Compound 9

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 9 and Compound 9 was synthesized by the same method.
Ionization mode APCI +: m / z = 654 [M + H], Exact Mass: 653

Synthesis Example 10: Synthesis of Compound 10

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 10, and Compound 10 was synthesized by the same method.
Ionization mode APCI +: m / z = 700 [M + H], Exact Mass: 699

Synthesis Example 11: Synthesis of Compound 11

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 11 and Compound 11 was synthesized by the same method.
Ionization mode APCI +: m / z = 651 [M + H], Exact Mass: 650

Synthesis Example 12: Synthesis of Compound 12

In Synthesis Example 4, Intermediate 4 was changed to Intermediate 12, and Compound 12 was synthesized by the same method.
Ionization mode APCI +: m / z = 711 [M + H], Exact Mass: 710

Synthesis Example 13 to Synthesis Example 24: Synthesis of Compound 13 to Compound 24 Intermediate 1 to Intermediate 12 were used instead of E-1. And compound 13 to compound 24 were synthesized by the same method.

Compound 13: Ionization mode APCI +: m / z = 700 [M + H], Exact Mass: 699
Compound 14: Ionization mode APCI +: m / z = 555 [M + H], Exact Mass: 554
Compound 15: Ionization mode APCI +: m / z = 555 [M + H], Exact Mass: 554
Compound 16: Ionization mode APCI +: m / z = 605 [M + H], Exact Mass: 604
Compound 17: Ionization mode APCI +: m / z = 750 [M + H], Exact Mass: 749
Compound 18: Ionization mode APCI +: m / z = 650 [M + H], Exact Mass: 649
Compound 19: Ionization mode APCI +: m / z = 606 [M + H], Exact Mass: 605
Compound 20: Ionization mode APCI +: m / z = 704 [M + H], Exact Mass: 703
Compound 21: Ionization mode APCI +: m / z = 704 [M + H], Exact Mass: 703
Compound 22: Ionization mode APCI +: m / z = 750 [M + H], Exact Mass: 749
Compound 23: APCI + in ionization mode: m / z = 701 [M + H], Exact Mass: 700
Compound 24: Ionization mode APCI +: m / z = 761 [M + H], Exact Mass: 760

Compound of Comparative Example A coloring agent (PY138) of the following structural formula was obtained from BASF and used as a compound of Comparative Example.

<Production Example of Photosensitive Resin Composition>
Example 1
5.554 g of compound 1 as a binder resin, a copolymer of benzyl methacrylate and methacrylic acid (Molar ratio 70:30, acid value 113 KOHmg / g, and gel permeation chromatography (Gel Permeation) Chromatography (GPC) and a weight average molecular weight of 20,000 g / mol, a molecular weight distribution (PDI) of 2.0 g, a solid content (SC) of 25%, and a solvent containing Propylene glycol monomethyl ether acetate (PGMEA)) 10.376 g, I-369 (BASF) 2.018 g as a photoinitiator, 12.443 g DPHA (Nippon Kayaku) as a photopolymerizable compound, a polyfunctional monomer, and propylene glycol monomethyl ether acetate as a solvent 68.593 g of ester (PGMEA) and 1.016 g of DIC's F-475 as a surfactant were mixed as an additive to produce a photosensitive resin composition of Example 1.

Example 2 to Example 24
Except that the compound 1 in Example 1 was changed to the compounds 2 to 24, the photosensitive resin compositions of Examples 2 to 24 were produced with the same composition as the photosensitive resin composition of Example 1.

Comparative Example: 5.554 g of the compound PY138 of Comparative Example, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (Molar ratio 70:30, acid value 113 KOHmg / g, permeate layer Weight average molecular weight 20,000 g / mol, molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, including solvent Propylene glycol monomethyl ether acetate (PGMEA) ) 10.376 g, I-369 (BASF) 2.018 g as a photoinitiator, 12.443 g DPHA (Nippon Kayaku) as a photopolymerizable compound, a polyfunctional monomer, and PGMEA (polypropylene glycol mono) as a solvent 68.593 g of methyl ether acetate) and 1.016 g of DIC's F-475 as an additive were mixed to produce a photosensitive resin composition of a comparative example.

＜ Experimental example ＞
Solubility Evaluation Prepare Compound 1 to Compound 24 and Compound (PY138) of Comparative Example, and measure the solubility of 100 g of dimethylformamide (DMF) at 25 ° C and 1 atmosphere.述 表 1。 Table 1. A case where the solubility is 1% or more is represented as O, and a case where the solubility is less than 1% is represented as X.

[Table 1]

Referring to Table 1, it can be seen that the coloring materials of Compounds 1 to 24 of the present invention have higher solubility in organic solvents (dimethylformamide) than the compound (PY138) of the comparative example.

Generally, in the case of a pigment, it is necessary to disperse | distribute using a derivative, a dispersing agent, etc. without being dissolved in an organic solvent. However, in the case of dissolving in an organic solvent like Examples 1 to 24 of the present specification, a derivative or a dispersant is not required, the amount of use can be reduced, and commercial applications can be easily performed.

Production of Substrate The photosensitive resin compositions of Examples 1 to 24 were used in the production of a substrate, respectively. Specifically, the photosensitive resin compositions of Examples 1 to 24 were spin-coated on glass (5 × 5 cm ² ) and subjected to prebake at 100 ° C. for 100 seconds. Form a film.

The interval between the film-formed substrate and a photo mask was set to 250 um, and the entire surface of the substrate was irradiated with an exposure device 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 subjected to postbake at 230 ° C for 20 minutes to prepare a substrate.

The heat resistance evaluation was performed using a spectroscope (MCPD-Otsuka Co., Ltd.) on a substrate produced by the substrate production method to obtain a transmittance spectrum in a visible light range of 380 nm to 780 nm. In addition, a prebake substrate was additionally subjected to postbake for 20 minutes at 230 ° C, and transmittance spectra were obtained with the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, and using the obtained values E (L *, a *, b *), the color change (hereinafter ΔEab) was calculated using the following formula 1 and shown in the following table 2 in.

A small ΔEab value indicates excellent color heat resistance.

If it has a value of ΔEab <3, it can be used as a pigment for a color filter, and can be called a coloring material having excellent heat resistance.
[Formula 1]

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

[Table 2]

With reference to Table 2, it was confirmed that the difference (ΔEab) in the transmittance spectrum between the post-heat treatment and the pre-heat treatment of the color pattern substrate formed using the photosensitive resin composition of Examples 1 to 24 of the present invention. Less than 3, high color stability, very little, and excellent heat resistance.

no

no

Claims (14)

A compound represented by the following Chemical Formula 1: Chemical Formula 1 In the Chemical Formula 1, at least one of R1 and R3 is represented by the following Chemical Formula 2 or Chemical Formula 3, and Chemical Formula 2 Chemical formula 3 In the chemical formula 2 and the chemical formula 3, Represents a site connected to the chemical formula 1, X is O or NH, and L is a substituted or unsubstituted alkylene, a substituted or unsubstituted heteroalkyl, or a substituted or unsubstituted alkylene Or substituted or unsubstituted heteroaryl, M is a direct bond, substituted or unsubstituted alkylene, substituted or unsubstituted heteroalkyl, substituted or unsubstituted Of aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted divalent dianhydride containing a nitrogen atom, one of R1 and R3 is not one of the above Chemical Formula 2 or Chemical Formula 3 In the formula, R4, R41 and R42 are the same or different from each other, and are independently selected from the group consisting of hydrogen, deuterium, halogen, nitrile, nitro, hydroxyl, -COR, -COOR, imidate, amido, and sulfonic acid. Group, anionic group, substituted or unsubstituted alkoxy group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkenyl group, substituted Or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted amine, In the group consisting of a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, and a substituted or unsubstituted dianhydride group containing a nitrogen atom, adjacent groups may be bonded to each other to form Ring, wherein R is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl, and r1 and r3 are 1 to 4 When r1 and r2 are 2 or more, the structure in parentheses () is the same or different, r4 is an integer of 0 to 4, and when r4 is 2 or more, R4 is the same or different, and r2 is 0 to When r2 is 2, R2 is the same or different. When r41 and r42 are integers of 0 to 3, when r41 and r42 are 2 or more, the structure in parentheses () is the same or different. The compound according to item 1 of the scope of patent application, wherein the chemical formula 1 is represented by the following chemical formula 4 or chemical formula 5: Chemical formula 4 Chemical formula 5 In the chemical formulas 4 and 5, R2 to R4, R41, R42, L, M, r2 to r4, r41, and r42 are as defined in the chemical formula 1, and R5 is selected from the group consisting of hydrogen, deuterium, halogen, halogen, and nitrile. Nitro, hydroxy, -COR, -COOR, fluorenimine, fluorenimide, anionic, sulfonic, substituted or unsubstituted alkoxy, substituted or unsubstituted alkyl , Substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, substituted or unsubstituted In the group consisting of a substituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, the R is hydrogen, deuterium, a substituted or unsubstituted alkyl group , A substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, r5 is an integer of 0 to 3, and when r5 is 2 or more, R5 are the same or different from each other. The compound according to item 1 of the scope of patent application, wherein the chemical formula 1 is represented by the following chemical formula 6 or chemical formula 7: Chemical formula 6 Chemical formula 7 In the chemical formulas 6 and 7, R1, R2, R4, R41, R42, L, M, r1, r2, r4, r41, and r42 are as defined in the chemical formula 1, and R6 is selected from the group consisting of hydrogen, deuterium, Halo, nitrile, nitro, hydroxyl, -COR, -COOR, fluorenimine, fluorenamine, anionic, sulfonic, substituted or unsubstituted alkoxy, substituted or unsubstituted Substituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted sulfonate, In the group consisting of a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, the R is hydrogen, deuterium, substituted or unsubstituted For substituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl, r6 is an integer of 0 to 3, and when r6 is 2 or more, R6 are the same or different from each other. The compound according to item 1 of the scope of patent application, wherein the chemical formula 1 is represented by the following chemical formula 4-1 or chemical formula 5-1: Chemical formula 4-1 Chemical formula 5-1 In the chemical formulas 4-1 and 5-1, R2 to R5, R41, R42, L, M, r2 to r5, r41, and r42 are as defined in the chemical formulas 4 and 5. The compound according to item 1 of the scope of patent application, wherein the chemical formula 1 is represented by the following chemical formula 6-1 or chemical formula 7-1: Chemical formula 6-1 Chemical formula 7-1 In the chemical formulas 6-1 and 7-1, R1, R2, R4, R6, R41, R42, L, M, r1, r2, r4, r6, r41, and r42 are as described in the chemical formula 6 and the chemical formula 7. By definition. The compound according to item 1 of the scope of patent application, wherein the chemical formula 1 is represented by the following chemical formula 1-1: Chemical formula 1-1 In the chemical formula 1-1, R1 to R3, r1, and r2 are as defined in the chemical formula 1, and R31 is hydrogen, deuterium, a substituted or unsubstituted sulfonate group, or a substituted or unsubstituted In the substituted dianhydride group containing a nitrogen atom, r3-1 is an integer of 0 to 3, and when r3-1 is 2 or more, R3 is the same or different. The compound according to item 1 of the scope of patent application, wherein at least one of the R3 may be represented by hydrogen, the following chemical formula S, chemical formula N or chemical formula M: Chemical formula S Chemical formula N Chemical formula M In the chemical formula S, chemical formula N and chemical formula M, Represents a site connected to the chemical formula 1, A is a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl group, and B is -X-X '-Or -X = X'-, X and X' are CR ₁₁ R ₁₂ , R ₁₁ and R ₁₂ are the same or different from each other, and are independently hydrogen, deuterium, N or S, or adjacent groups are bonded to each other To form a ring, Z1 to Z3 are the same or different from each other, and are each independently hydrogen, deuterium, halogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, or adjacent groups may Bond to each other to form a ring. The compound according to item 1 of the scope of patent application, wherein the compound represented by Chemical Formula 1 is represented by any one of the following chemical formulas: . A photosensitive resin composition comprising the compound according to any one of claims 1 to 8 of the scope of patent application, a binder resin, a polyfunctional monomer, a photoinitiator, and a solvent. The photosensitive resin composition according to item 9 of the scope of application for a patent, wherein a content of the compound represented by the chemical formula 1 is 5% by weight to 5% by weight based on the total weight of solid components in the photosensitive resin composition. 60% by weight, The content of the binder resin is 1% to 60% by weight. The content of the photo-initiator is 0.1% to 20% by weight, The content of the polyfunctional monomer is 0.1 to 50% by weight. The photosensitive resin composition according to item 9 of the scope of patent application, further comprising an additive. A photosensitive material manufactured using the photosensitive resin composition as described in item 9 of the patent application range. A color filter includes the photosensitive material according to item 12 of the scope of patent application. A display device includes the color filter according to item 13 of the scope of patent application.