CN111527075B

CN111527075B - Xanthene compound, photosensitive resin composition containing same, photosensitive material, color filter, and display device

Info

Publication number: CN111527075B
Application number: CN201880084202.5A
Authority: CN
Inventors: 朴锺镐; 崔相雅; 李多美; 郑智惠; 梁承秦; 李永熙
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-04-05
Filing date: 2018-11-12
Publication date: 2024-03-15
Anticipated expiration: 2038-11-12
Also published as: JP6940231B2; CN111527075A; TW201943714A; JP2021508746A; TWI679200B; KR20190116897A; KR102156478B1

Abstract

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

Description

Xanthene compound, photosensitive resin composition containing same, photosensitive material, color filter, and display device

Technical Field

The present application claims priority from korean patent application No. 10-2018-0039901, filed in the korean patent office on the 05 th month of 2018, the entire contents of which are incorporated herein.

The present application claims priority from korean patent application No. 10-2018-0135550, filed to the korean patent office on 11/06 of 2018, the entire contents of which are incorporated herein.

The present invention relates to a xanthene compound and a photosensitive resin composition containing the same. The present disclosure also relates to a photosensitive material produced using the photosensitive resin composition, a color filter, and a display device including the same.

Background

In recent years, color filters are required to have performance characterized by high brightness and high contrast. In addition, one of the main purposes of display device development is to realize differentiation of display element performance and increase productivity of manufacturing process by improving color purity.

Since pigment types conventionally used as coloring materials for color filters exist in a color photoresist in a particle dispersed state, there is a difficulty in adjusting brightness and contrast by adjusting the size and distribution of pigment particles. In the case of pigment particles, the dissolution and dispersion properties are reduced by aggregation in the color filter, and multiple scattering of light occurs due to aggregated (aggregated) macroparticles (multiple scattering). Such scattering of polarized light is considered to be a major cause of reduced contrast. Although efforts have been continuously made to improve brightness and contrast by ultramicronization and dispersion stabilization of pigments, there is a limit in freedom in selection of colorants for realizing color coordinates for high color purity display devices. In addition, pigment dispersion methods using pigments, particularly pigments, which have been developed, have reached a limit in improving color purity, brightness, and contrast of color filters using the same.

Accordingly, development of a novel coloring material capable of improving color reproduction, brightness and contrast by improving color purity has been demanded.

Disclosure of Invention

Technical problem

The present inventors have aimed at providing a xanthene compound having a novel structure, a photosensitive resin composition containing the same, a photosensitive material produced using the same, a color filter, and a display device containing the same.

Solution to the problem

An embodiment of the present specification provides a compound represented by the following chemical formula 1.

[ chemical formula 1]

In the above-mentioned chemical formula 1,

l1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted alkylene group,

r1 and R2 are identical or different from each other and are each independently a dianhydride group containing a nitrogen atom,

r3 and R4 are the same or different from each other and are each independently a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

r5 to R12 are identical or different from each other and are each independently selected from hydrogen, deuterium, halogen radicals, -OH, -SO ₃ H、-SO ₃ M、-SO ₂ NM1M2、-SO ₂ NHY, -COOH, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl,

r13 to R17 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen radical, -OH, -SO ₃ ^- 、-SO ₃ H、-SO ₃ M、-SO ₂ NM1M2、-SO ₂ NHY, -COOH, an anionic group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

m is selected from Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure,

M1, M2 and Y are the same or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, at least one of R13 to R17 being an anionic group,

x is an anionic group and is preferably a hydroxyl group,

a is 0 or 1, and the number of the components is 1,

r5 and R6 are integers from 0 to 4, and when R5 is 2 or more, R5 is the same or different from each other, and when R6 is 2 or more, R6 is the same or different from each other.

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

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

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

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

Effects of the invention

The compound according to one embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, and by having solubility in an organic solvent, the dispersing step can be reduced, and the compound can be used as a coloring material in an economical manner, unlike the case where the dispersing step is required in the conventional pigment application. Further, by reducing the fluorescence intensity, the contrast can be improved without adding an additional pigment.

In addition, the xanthene compound according to one embodiment of the present specification is used as a coloring material, and thus color reproduction, brightness, and contrast can be improved.

Drawings

Fig. 1 is a graph showing the detected fluorescence intensities of substrates manufactured using the compounds according to some examples and comparative examples of the present specification.

FIG. 2 shows the vision of a compound according to an embodiment of the present disclosure

Fig. 3 shows transmittance of substrates manufactured using the compounds according to some examples and comparative examples of the present specification.

Detailed Description

The present specification will be described in more detail below.

In this specification, when it is stated that a certain member is located "on" another member, it includes not only the case where the certain member is in contact with the other member but also the case where another member exists between the two members.

In the present specification, when a certain component is indicated as being "included" in a certain portion, unless otherwise stated, it means that other components may be further included, and not excluded.

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

The present invention has excellent solubility in organic solvents by including the compound represented by the above chemical formula 1. Specifically, the above chemical formula 1 can increase the solubility in an organic solvent by substituting an aryl group substituted on nitrogen of a Xanthene (Xanthene) structure with a substituent containing sulfur (S) and containing a bulky substituent such as a dianhydride group containing a nitrogen atom.

In addition, in the case where the aryl group substituted on nitrogen of the xanthene structure in the above chemical formula 1 is substituted with a substituent containing sulfur (S), the fluorescence intensity is reduced as compared with the case where the aryl group is substituted with a substituent not containing sulfur (S), and an excellent contrast can be obtained even without adding an additional pigment.

This increases the solubility, thereby preventing aggregation between the coloring materials, and reducing the amount of material required for dispersing the coloring materials, thereby improving the economical efficiency.

In addition, contrast Ratio (CR) can be improved, and excellent heat resistance can be provided. In order to reduce luminescence (fluorescence or phosphorescence) of molecules, there are methods of reducing flatness within molecules or introducing molecules that absorb light. When a light-absorbing molecule is introduced, it is difficult to selectively absorb only light of an emission wavelength because all of light of the molecule that emits light and light of the outside are absorbed. Therefore, a substituent (bulk group) having a large steric hindrance is introduced to reduce the intramolecular planarity.

Non-radiative decay (non-radiative decay) can occur when molecules that absorb light in the ground state to become excited (excited) move energy in either a vibrational mode (vibration mode) or a rotational mode (rotation mode). That is, light emission can be reduced.

The larger the planarity, the more difficult the non-radiative decay becomes, and the more the intensity of luminescence increases, and the larger the substituent is introduced to reduce the planar area, the more the intensity of luminescence can be reduced by the non-radiative decay. For non-radiative decay, long alkyl (alkyl group), branched alkyl (branch ed alkyl group), alkoxy (alkxy group), amine group (amine group) may be introduced. However, alkyl (alkyl) has a disadvantage of insufficient heat resistance.

In the case of an alkoxy group (alkoxy) and an amine group (amine group), the molecule functions as an electron donating group (electron donating group), and the absorption wavelength of the molecule that absorbs light can be changed.

In contrast, when a molecule containing sulfur (S) is introduced, the action of the electron donating group (electron donating group) or the like is reduced in the molecule absorbing light, and heat resistance can be maintained.

When sulfur atoms (sulfur atoms) having a larger atomic size than carbon, nitrogen, and oxygen are introduced, the energy of the excited molecules moves to sulfur atoms (sulfur atoms) having various energy levels, and moves between the various energy levels of the sulfur atoms, that is, moves according to vibration mode (vibration mode) and rotation mode (rotation mode), and non-radiative decay (non-radiative decay) can occur. Due to such characteristics, the intensity of luminescence within the molecule can be reduced when sulfur atoms (sulfur atoms) are introduced.

When a molecule having luminescence is applied to a Liquid Crystal Display (LCD), a decrease in Contrast Ratio (CR) may occur, which may cause a problem of quality degradation. Accordingly, various methods have been adopted in an attempt to reduce the light emission.

In order to suppress the decrease in Contrast (CR), molecules that absorb luminescence are now put in. However, the color purity was decreased and the amount of the coloring material used was increased.

Examples of the substituent of the compound represented by the above chemical formula 1 are described below, but are not limited thereto.

In the present description of the invention,refers to a site of attachment to other substituents or binding sites.

In the present specification, the term "substituted or unsubstituted" means selected from deuterium; a halogen group; a nitrile group; a nitro group; -OH; a carbonyl group; an ester group; -COOH; an imide group; an amide group; an anionic group; an alkoxy group; an alkyl group; cycloalkyl; alkenyl groups; a cycloalkenyl group; an aralkyl group; a phosphine group; sulfonate; an amine group; an aryl group; heteroaryl; a silyl group; a boron base; an acryl group; an acrylate group; an ether group; a heterocyclic group containing 1 or more of N, O, S or P atoms and 1 or more of substituents in an anionic group may be substituted or may have no substituent.

In this specification, an "adjacent" group may represent a substituent substituted on an atom directly connected to an atom substituted with the substituent, a substituent closest to the substituent in steric structure, or another substituent substituted on an atom substituted with the substituent. For example, 2 substituents substituted in the ortho (ortho) position in the benzene ring and 2 substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the above-mentioned ring in which adjacent groups may be combined to form a "ring" means an aromatic or aliphatic ring. Specifically, the ring may be an aromatic ring, and may be an aryl group or a heteroaryl group. The above aryl and heteroaryl groups may be used as described below.

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

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

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

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 30. Specifically, the compound may have the following structure, but is not limited thereto.

In the present specification, in the amide group, nitrogen of the amide group may be substituted with 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, the compound may be a compound of the following structural formula, but is not limited thereto.

In the present specification, a phosphine group means an alkylphosphine group or arylphosphine group, and the alkylphosphine group means a phosphine group substituted with an alkyl group. The number of carbon atoms of the alkylphosphinyl group is not particularly limited, but is preferably 1 to 20. Examples of the alkylphosphine group include, but are not limited to, dimethylphosphine group, diethylphosphino group, di-n-propylphosphino group, diisopropylphosphino group, di-n-butylphosphino group, di-sec-butylphosphino group, di-tert-butylphosphino group, diisobutylphosphino group, tert-butylisopropylphosphino group, di-n-hexylphosphino group, di-n-octylphosphino group, di-n-methylphosphine group, and the like. The above arylphosphino group refers to a phosphino group substituted with an aryl group. The number of carbon atoms of the above arylphosphino group is not particularly limited, but is preferably 6 to 30. Examples of the above arylphosphino group include, but are not limited to, diphenylphosphino group, dibenzylphosphino group, methylphenylphosphino group, benzylhexylphosphino group, and bistrimethylsilylphosphino group.

In the present specification, the anionic group has a chemical bond with the structure of chemical formula 1, and the above chemical bond may be referred to as an ionic bond. The anionic group is not particularly limited, and for example, anions described in U.S. Pat. No. 7,939,644, japanese patent application laid-open No. 2006-003080, japanese patent application laid-open No. 2006-001917, japanese patent application laid-open No. 2005-159926, japanese patent application laid-open No. 2007-7028897, japanese patent application laid-open No. 2005-071680, korean application laid-open No. 2007-7000693, japanese patent application laid-open No. 2005-111696, japanese patent application laid-open No. 2008-249663, and Japanese patent application laid-open No. 2014-199436 can be used.

Specific examples of the anionic groups include trifluoromethanesulfonyl anions, bis (trifluoromethanesulfonyl) amide anions, bis (trifluoromethanesulfonyl) imide anions, bis (perfluoroethylsulfonyl) imide anions, tetraphenylborate anions, tetrakis (4-fluorophenyl) borate anions, tetrakis (pentafluorophenyl) borate anions, tris (trifluoromethanesulfonyl) methylated anions, SO ₃ ^- 、CO ₂ ^- 、SO ₂ N ^- SO ₂ CF ₃ 、SO ₂ N ^- SO ₂ CF ₂ CF ₃ Halogen groups, e.g., fluorine groups, iodine groups, chlorine groups, etc., but are not limited toThis is done.

In the present specification, the anionic group may itself have an anion, or may exist in a coordinated form together with other cations. Thus, the sum of the overall charges of the molecules of the compounds of the present invention may vary depending on the number of substituted anionic groups. For example, when the chemical formula 1 contains an ammonium structure, since the one ammonium structure has a cation, the sum of the overall charges of the molecules may have a value of 0 to an anion of a value obtained by subtracting 1 from the number of substituted anionic groups.

In the present specification, the above-mentioned alkoxy group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30, more preferably 1 to 20, and still more preferably 1 to 10.

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the above alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, and n-octyl. In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 30 carbon atoms is preferable, and cyclopentyl and cyclohexyl are particularly preferable, but the present invention is not limited thereto.

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

In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the alkenyl group has 2 to 30 carbon atoms. According to another embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group include, but are not limited to, alkenyl groups in which an aryl group such as a stilbene group (styryl) or styryl (styryl) is substituted.

In the present specification, the cycloalkenyl group is not particularly limited, but is preferably a cycloalkenyl group having 3 to 60 carbon atoms, and according to one embodiment, the cycloalkenyl group has 3 to 30 carbon atoms. According to another embodiment, the above cycloalkenyl group has a carbon number of 3 to 20. According to another embodiment, the above cycloalkenyl group has a carbon number of 3 to 6. As examples of the cycloalkenyl group, cyclopentenyl group and cyclohexenyl group are preferable, but not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthracenyl, indenyl, phenanthryl, pyrenyl, perylenyl, triphenyl, A group, a fluorenyl group, etc., but is not limited thereto.

In this specification, a fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure.

In the case where the fluorenyl group is substituted, it may be thatAn isospirofluorenyl group,(9, 9-dimethylfluorenyl) and +.>(9, 9-Di)Phenylfluorenyl), and the like. However, the present invention is not limited thereto.

In the present specification, specifically, the number of carbon atoms of the aryl portion of the above aralkyl group may be 6 to 30, and the number of carbon atoms of the alkyl portion may be 1 to 30. Specific examples thereof include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3, 5-dimethylbenzyl, α -methylbenzyl, α -dimethylbenzyl, α -methylphenyl benzyl, 1-naphthylbenzyl, 2-naphthylbenzyl, p-fluorobenzyl, 3, 5-difluorobenzyl, α -bistrifluoromethylbenzyl, p-methoxybenzyl, m-methoxybenzyl, α -phenoxybenzyl, α -benzyloxybenzyl, naphthylmethyl, naphthylethyl, naphthylisopropyl, pyrrolylmethyl, pyrrolylethyl, aminobenzyl, nitrobenzyl, cyanobenzyl, 1-hydroxy-2-phenylisopropyl, 1-chloro-2-phenylisopropyl and the like, but are not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a heteroatom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 30, specifically, 2 to 20. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, triazinyl, acridinyl, pyridazinyl, quinolinyl, isoquinolinyl, indolyl, carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, and the like, but are not limited thereto.

In this specification, the heteroaryl group is aromatic, and the above description of the heterocyclic group can be applied thereto.

In the present specification, the silyl group may be represented by the chemical formula-SiZ 1Z2Z3, and each of the above Z1, Z2 and Z3 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically, but not limited to, trimethylsilyl (TMS), triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like.

In the present specification, as alkylsulfonyl [ ]Alkylsulfoxy) includes methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, and the like, but is not limited thereto. The alkyl group in the above alkylsulfonyl group may be as described above with respect to the alkyl group.

In the present specification, the boron group may be represented by the formula of-BW 4W5, and each of the above W4 and W5 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Examples of the boron group include trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but are not limited thereto.

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

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

In the present specification, "(meth) acryl" means at least one selected from acryl and methacryl. The designation of "(meth) acrylate" also has the same meaning.

In this specification, the ether group may be represented by-COR. R is a substituted or unsubstituted alkyl group. The alkyl group may be any of the alkyl groups described above.

In the present specification, the sulfonate group may be an alkyl sulfonate group or an aryl sulfonate group. The above "alkyl" may be applied to the above description of alkyl groups, and the above "aryl" may be applied to the above description of aryl groups.

In the present specification, the amine group may be selected from the group consisting of-NH ₂ The alkyl amine group, the N-alkylaryl amine group, the aryl amine group, the N-arylheteroaryl amine group, the N-alkylheteroaryl amine group and the heteroaryl amine group are not particularly limited, but are preferably 1 to 30 in carbon number. Specific examples of the amine group include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a phenylamine group, a naphthylamino group, a biphenylamino group, an anthracenylamino group, a 9-methyl-anthracenylamino group, a diphenylamino group, an N-phenylnaphthylamino group, a xylylamino group, an N-phenyltolylamino group, a triphenylamino group, an N-phenylbiphenylamino group, an N-phenylnaphthylamino group, an N-biphenylnaphthylamino group, an N-naphthylfluorenylamino group, an N-phenylphenanthrylamino group, an N-biphenylphenanthrenylamino group, an N-phenylfluorenylamino group, an N-biphenylfluorenylamino group, and the like, but are not limited thereto.

In the present specification, the number of carbon atoms of the dianhydride group containing a nitrogen atom is not particularly limited, but may be 4 to 30, specifically 4 to 20, more specifically 4 to 15.

In the present specification, alkylene means a group having two binding sites on alkane (alkine). The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, and for example, the number of carbon atoms is 1 to 30, specifically 1 to 20, more specifically 1 to 10.

In the present specification, the heteroalkylene group means a group having two binding sites on an alkane (alkine) containing O, N or S as a hetero atom. The alkylene group may be linear, branched or cyclic. The number of carbon atoms of the alkylene group is not particularly limited, and for example, the number of carbon atoms is 2 to 30, specifically the number of carbon atoms is 2 to 20, more specifically the number of carbon atoms is 2 to 10.

In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and the above description of aryl groups can be applied.

In the present specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. They may be suitable for the description of heteroaryl groups described above, except that each is a 2-valent group.

In one embodiment of the present specification, each of the above L1 and L2 is the same or different from each other, and is independently a substituted or unsubstituted straight-chain or branched alkylene group.

In one embodiment of the present specification, L1 and L2 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted straight-chain or branched alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted straight-chain or branched alkylene group having 1 to 20 carbon atoms.

According to an embodiment of the present specification, L1 and L2 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted straight-chain or branched alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L1 and L2 of the above chemical formula 1 are the same or different from each other, and are each independently a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, a substituted or unsubstituted propylene group, or a substituted or unsubstituted butylene group.

In one embodiment of the present specification, L1 and L2 of the above chemical formula 1 are the same or different from each other, and each is independently methylene, ethylene, propylene or butylene.

In one embodiment of the present specification, R1 and R2 in the above chemical formula 1 are the same or different from each other, and each is independently a dianhydride group having 4 to 30 carbon atoms and containing a nitrogen atom.

In one embodiment of the present specification, R1 and R2 in the above chemical formula 1 are the same or different from each other, and each is independently a dianhydride group having 4 to 20 carbon atoms and containing a nitrogen atom.

In one embodiment of the present specification, R1 and R2 in the above chemical formula 1 are the same or different from each other, and each is independently a dianhydride group having 4 to 15 carbon atoms and containing a nitrogen atom.

In one embodiment of the present specification, the dianhydride group containing a nitrogen atom may be represented by any one of the following substituents.

Of the above-mentioned substituents, the group consisting of,represents a site to which L1 or L2 in the above chemical formula 1 is bonded,

x1, X2 and Y1 to Y3 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitro group, -OH, -SO ₃ H. -COOH, phosphino, anionic groups, substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups, or adjacent groups combine to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the above X1 and X2 may be combined with each other to form a substituted or unsubstituted ring.

In one embodiment of the present specification, X1 and X2 may be combined with each other to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

In one embodiment of the present specification, the above X1 and X2 may combine with each other to form a protected SO ₃ M or-SO ₂ NHY substituted or unsubstituted benzene ring, or substituted with-SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted naphthalene ring, and M and Y are as defined in chemical formula 1.

In one embodiment of the present specification, the above X1 and X2 may combine with each other to form a protected SO ₃ M or-SO ₂ NHY substituted or unsubstituted benzene ring, or substituted with-SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted naphthalene ring, M is selected from the group consisting of hydrogen, na, K, rb, cs, fr, and a moiety comprising an ammonium structure, and Y is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the above X1 and X2 may combine with each other to form a protected SO ₃ M or-SO ₂ NHY substituted or unsubstituted benzeneA ring, or be-SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted naphthalene ring, M is selected from the group consisting of hydrogen, na, K, rb, cs, fr, and a moiety comprising an ammonium structure, and Y is a substituted or unsubstituted n-hexyl.

In one embodiment of the present specification, the above X1 and X2 may combine with each other to form a protected SO ₃ M or-SO ₂ NHY substituted or unsubstituted benzene ring, or substituted with-SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted naphthalene ring, M is selected from the group consisting of hydrogen, na, K, rb, cs, fr, and a moiety comprising an ammonium structure, and Y is n-hexyl substituted with ethyl.

In one embodiment of the present disclosure, the above Y1 and Y2, and Y2 and Y3 may be combined to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Y1 and Y2, and Y2 and Y3 may be combined to form a substituted or unsubstituted benzene ring.

In one embodiment of the present specification, the above Y1 and Y2, and Y2 and Y3 may be combined to form an protected SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted benzene ring, and M and Y are as defined in chemical formula 1.

In one embodiment of the present specification, the above Y1 and Y2, and Y2 and Y3 may be combined to form an protected SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted benzene ring, and M is Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure, wherein Y is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the above Y1 and Y2, and Y2 and Y3 may be combined to form an protected SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted benzene ring, and M is Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure, wherein Y is a substituted or unsubstituted n-hexyl group.

In one embodiment of the present specification, the above Y1 and Y2, and Y2 and Y3 may be combined to form an protected SO ₃ M or-SO ₂ NHY is a substituted or unsubstituted benzene ring, and M is selected fromFrom Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure, wherein Y is an n-hexyl group substituted with an ethyl group.

Among the above-mentioned substituents, the amino group,represents a site to which L1 or L2 in the above chemical formula 1 is attached, X3 to X5 and Y4 are the same or different from each other, and are each independently hydrogen, deuterium, a halogen group, nitro, -OH, -SO ₃ H、-SO ₃ M、-SO ₂ NHY, -COOH, phosphino, an anionic group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, M and Y are as defined in chemical formula 1 above, x3 is an integer of 0 to 4, and x4, x5, and Y4 are integers of 0 to 6.

Among the above-mentioned substituents, the amino group,represents a site to which L1 or L2 in the above chemical formula 1 is attached, X3 to X5 and Y4 are the same or different from each other, and each is independently hydrogen, -SO ₃ M, or-SO ₂ NHY, where M and Y are as defined in chemical formula 1, x3 is an integer of 0 to 4, and x4, x5 and Y4 are integers of 0 to 6.

In one embodiment of the present specification, R3 and R4 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R3 and R4 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3 and R4 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3 and R4 of the above chemical formula 1 are the same or different from each other, and each is independently a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R3 and R4 of the above chemical formula 1 are the same or different from each other, and each is independently a methyl group, a methyl group substituted with a halogen group, or a phenyl group.

In one embodiment of the present specification, R3 and R4 of the above chemical formula 1 are the same or different from each other and are each independently methyl, trifluoromethyl (-CF) ₃ ) Or phenyl.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently selected from hydrogen, deuterium, halogen group, nitro group, hydroxyl group, -COR, -COOR, imide group, amide group, anionic group, substituted or unsubstituted alkoxy group of 1 to 30 carbon atoms, substituted or unsubstituted alkyl group of 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group of 3 to 30 carbon atoms, substituted or unsubstituted alkenyl group of 2 to 30 carbon atoms, substituted or unsubstituted cycloalkenyl group of 3 to 30 carbon atoms, substituted or unsubstituted sulfonate group, substituted or unsubstituted amino group of 1 to 30 carbon atoms, substituted or unsubstituted aryl group of 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group of 2 to 30 carbon atoms,

The above R is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently selected from hydrogen, deuterium, halogen group, -OH, -SO ₃ H、-SO ₃ M、-SO ₂ NM1M2、-SO ₂ NHY、-COOH, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, said M being selected from Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure, the above M1, M2 and Y being the same or different from each other, each independently selected from the group consisting of substituted or unsubstituted alkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY, or a substituted or unsubstituted alkyl group, wherein Y is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and Y is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and Y is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY, or a substituted or unsubstituted methyl group, wherein Y is a substituted or unsubstituted hexyl group.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY, or substituted or unsubstituted by halogen groupsMethyl, and Y is hexyl substituted or unsubstituted by ethyl.

In one embodiment of the present specification, R5 to R12 of the above chemical formula 1 are the same or different from each other and are each independently hydrogen, -SO ₂ NHY, or trifluoromethyl (-CF) ₃ ) The above Y is a hexyl group substituted with an ethyl group.

In one embodiment of the present specification, R5 in chemical formula 1 is hydrogen or trifluoromethyl.

In one embodiment of the present specification, R6 of the above chemical formula 1 is hydrogen, -SO ₂ NHY, or trifluoromethyl, where Y is hexyl substituted with ethyl.

In one embodiment of the present specification, R7 in chemical formula 1 is hydrogen.

In one embodiment of the present specification, R8 in chemical formula 1 is hydrogen.

In one embodiment of the present specification, R9 in chemical formula 1 is hydrogen.

In one embodiment of the present specification, R10 in chemical formula 1 is hydrogen.

In one embodiment of the present specification, R11 in chemical formula 1 is hydrogen.

In one embodiment of the present specification, R12 in chemical formula 1 is hydrogen.

In addition, in one embodiment of the present specification, R13 to R17 are the same or different from each other and are each independently hydrogen, deuterium, a halogen group, -OH, -SO ₃ ^- 、-SO ₃ H、-SO ₃ M、-SO ₂ NM1M2、-SO ₂ NHY, -COOH, an anionic group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, where M is selected from Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure, wherein M1, M2 and Y are the same or different from each other and are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heteroaryl group, and wherein at least one of R13 to R17 is an anionic group.

One of the specifications of the present specificationIn embodiments, R13 to R17 are the same or different from each other and are each independently hydrogen, -SO ₃ ^- 、-SO ₃ M or-SO ₂ NHY, M and Y are as defined above, and at least one of R13 to R17 is an anionic group.

In one embodiment of the present specification, R13 to R17 are the same or different from each other and are each independently hydrogen, -SO ₃ ^- 、-SO ₃ M, or-SO ₂ NHY, where M and Y are as defined above, and at least one of R13 to R17 is-SO ₃ ^- 。

In one embodiment of the present specification, R13 is-SO ₃ ^- 。

In one embodiment of the present specification, R4 is hydrogen.

In one embodiment of the present specification, R15 is hydrogen, -SO ₃ M or-SO ₂ NHY, M and Y are as defined above.

In one embodiment of the present disclosure, R16 is hydrogen.

In one embodiment of the present specification, R17 is hydrogen.

In one embodiment of the present specification, X is an anionic group.

In one embodiment of the present specification, X is selected from anions of a compound containing at least one element selected from tungsten, molybdenum, silicon and phosphorus and oxygen; a triflate anion; bis (trifluoromethylsulfonyl) amide anion; bis-trifluoromethanesulfonyl imide anions; biperfluoroethylsulfonimide anions; tetraphenyl borate anions; tetra (4-fluorophenyl) borate anions; tetra (pentafluorophenyl) borate anions; a tris (trifluoromethanesulfonyl) methylated anion; a halogen group.

In one embodiment of the present disclosure, X may be SO ₃ ^- 。

In one embodiment of the present specification, R5 and R6 are integers from 0 to 4, R5 is equal to or different from each other when R5 is 2 or more, and R6 is equal to or different from each other when R6 is 2 or more.

In one embodiment of the present specification, R5 and R6 are integers of 0 to 3, R5 is equal to or different from each other when R5 is 2 or more, and R6 is equal to or different from each other when R6 is 2 or more.

In one embodiment of the present specification, R5 and R6 are integers from 0 to 2, and when R5 is 2 or more, R5 is the same or different from each other, and when R6 is 2, R6 is the same or different from each other.

In one embodiment of the present description, r5 and r6 are 0 or 1.

In one embodiment of the present disclosure, r5 and r6 are 0.

In one embodiment of the present description, r5 and r6 are 1.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following structure, wherein the following structure represents an isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. Isomers refer to molecules of the same molecular formula but having different physical/chemical properties from each other.

In the above structure, L1, L2, R1 to R17, X, a, R5 and R6 are as defined in the above chemical formula 1.

The above description of the isomers is applicable to all of the xanthene dye structures described in the present specification.

In one embodiment of the present specification, the above-mentioned-SO ₃ M may represent-SO ₃ ^- And M ion binding or salt binding.

In one embodiment of the present specification, M is selected from Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure, which may comprise a unit represented by the following chemical formula a or by the following chemical formula B.

[ chemical formula A ]

[ chemical formula B ]

In the above-mentioned chemical formula a,

ra to Rd are the same or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, -L ₁ -NHCO-R, or-L ₂ OCO-R, or two of Ra to Rd, combine with each other to form a substituted or unsubstituted ring, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, L is ₁ And L ₂ In order to be substituted or unsubstituted alkylene groups,

in the above-mentioned chemical formula B, the amino acid,

rb to Rd are the same or different from each other and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, or substituted or unsubstituted aralkyl, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, Z is substituted or unsubstituted alkylene, substituted or unsubstituted arylene, -L ₃ -NHCO-, or-L ₄ OCO-, L as above ₃ And L ₄ Re to Rg are the same or different from each other and each independently hydrogen or a substituted or unsubstituted alkyl group.

According to an embodiment of the present specification, in the above chemical formula a, ra to Rd are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, -L ₁ -NHCO-R, or-L ₂ -OCO-R, or two of Ra to Rd, which are bonded to each other to form a substituted or unsubstituted ring, wherein R is hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms30, a substituted or unsubstituted aralkyl group, L as defined above ₁ And L ₂ Is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms,

in the above formula B, rb to Rd are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, or two of Rb to Rd are bonded to each other to form a substituted or unsubstituted ring, Z is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, -L ₃ -NHCO-, or-L ₄ OCO-, L as above ₃ And L ₄ Is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, re to Rg are the same or different from each other, and each is independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

According to an embodiment of the present specification, in the above chemical formula a, ra to Rd are the same or different from each other and are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 20 carbon atoms, -L ₁ -NHCO-R, or-L ₂ -OCO-R, or 2 of Ra to Rd are bonded to each other to form a substituted or unsubstituted ring, wherein R is hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 20 carbon atoms, and L is ₁ And L ₂ Is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms,

in the above chemical formula B, rb to Rd are the same or different from each other and each is independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 20 carbon atoms, or 2 of Rb to Rd are bonded to each other to form a substituted or unsubstituted ring, Z is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, -L ₃ -NHCO-, or-L ₄ OCO-, L as above ₃ And L ₄ Is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, re to Rg are the same or different from each other, and each is independently hydrogen or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, the above units refer to a repeating structure in which a monomer is contained in a polymer, and the above units may be contained in a main chain within the polymer to constitute the polymer.

In one embodiment of the present specification, the compound including the unit represented by the above chemical formula B may be a polymer.

When the compound containing the unit represented by the above chemical formula B is a polymer, the unit represented by the above chemical formula B may be contained in the range of 1 to 500.

In one embodiment of the present specification, the weight average molecular weight of the compound including the unit represented by the above chemical formula B may be 1000 to 10000, preferably 3000 to 8000, more preferably 5000 to 7000.

According to an embodiment of the present specification, the terminal of the compound including the unit represented by the above chemical formula B may be hydrogen, a halogen group, or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 2.

[ chemical formula 2]

In the above-mentioned chemical formula 2,

l1, L2, R1 to R17, X, a, R5 and R6 are as defined in chemical formula 1 above.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 3.

[ chemical formula 3]

In the above-mentioned chemical formula 3, a compound represented by formula 1,

l1, L2, R1 to R17, X, a, R5 and R6 are as defined in chemical formula 1 above.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 4.

[ chemical formula 4]

In the above-mentioned chemical formula 4, a compound represented by formula 1,

l1, L2, R1 to R17, X, a, R5 and R6 are as defined in chemical formula 1 above.

In one embodiment of the present specification, the dianhydride group having a nitrogen atom of the above chemical formula 1 may be a compound represented by any one of the following substituents.

Among the above-mentioned substituents, the amino group,represents a site to which L1 or L2 in the above chemical formula 1 is bonded,

x1, X2, Y1 to Y3 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, a nitro group, -OH, -SO ₃ H. -COOH, phosphino, anionic groups, substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups, or adjacent groups may combine to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the compound represented by the above chemical formula 1 may be represented by any one of the following chemical formulas.

/>

In the above chemical formula, M and Y are as defined in the above chemical formula 1.

In one embodiment of the present specification, a substituent in the ring of the above formula, for which a substitution position is not specified, means that it may be substituted on any part of carbon contained in the ring.

At the position ofIn (I)>Represented by-CF ₃ In substituted benzene rings other than by-SCH ₃ The substituted carbon may be substituted on any one of the remaining carbons, and specifically, may be represented by the following 4 structures.

As another example, inIn (I)>Represented by-SO ₂ The NHY-substituted naphthalene ring may be substituted on any one of carbons included in naphthalene, and specifically, may be represented by the following 6 structures.

In the above 6 structures, Y is the same as defined above.

In addition, according to an embodiment of the present specification, a coloring material composition including the above-described compound can be provided.

The coloring material composition may contain at least 1 of a dye and a pigment in addition to the compound of the chemical formula 1. For example, the coloring material composition may contain only the compound of the chemical formula 1, but may contain the compound of the chemical formula 1 and 1 or more dyes, or contain the compound of the chemical formula 1 and 1 or more pigments, or contain the compound of the chemical formula 1, 1 or more dyes and 1 or more pigments.

According to an embodiment of the present specification, a photosensitive resin composition including the above-described coloring material composition can be provided.

According to an embodiment of the present specification, the photosensitive resin composition may further include a compound represented by the chemical formula 1, a binder resin, a polyfunctional monomer, a photopolymerization initiator, and a solvent.

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

The binder resin may be a copolymer resin of a polyfunctional monomer imparting mechanical strength and an alkali-soluble monomer, and may further contain a binder commonly used in the art.

The polyfunctional monomer imparting mechanical strength to the film may be any one or more of unsaturated carboxylic acid esters, aromatic vinyl groups, unsaturated ethers, unsaturated imides, and acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxyethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxy (meth) acrylate, P-nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1, 3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl (α -hydroxymethyl) acrylate, ethyl (α -hydroxymethyl) acrylate, propyl (α -hydroxymethyl) acrylate, and butyl (α -hydroxymethyl) acrylate, but are not limited thereto.

Specific examples of the aromatic vinyl group include, but are not limited to, styrene, α -methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p) -chlorostyrene.

Specific examples of the unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.

Specific examples of the above-mentioned unsaturated imides may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide, but are not limited thereto.

Examples of the acid anhydride include, but are not limited to, maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride, and the like.

The alkali-solubility-imparting monomer is not particularly limited as long as it contains an acid group, and for example, one or more selected from (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono (2- ((meth) acryloyloxy) ethylphthalate, mono-2- ((meth) acryloyloxy) ethylsuccinate, and ω -carboxyl polycaprolactone mono (meth) acrylate is preferably used, but not limited thereto.

According to an embodiment of the present specification, the acid value of the above binder resin is 50 to 130KOHmg/g, and the weight average molecular weight is 1000 to 50000.

The polyfunctional monomer is a monomer that functions to form a photo-etching resist image by light, and specifically may be one or a mixture of two or more selected from propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 1, 6-hexanediol diacrylate, tetraethylene glycol methacrylate, diphenoxyethanol diacrylate, trihydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, and dipentaerythritol hexamethacrylate.

The photopolymerization initiator is not particularly limited as long as it is an initiator that triggers crosslinking by generating radicals by light, and may be, for example, one or more selected from acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds.

Examples of the acetophenone-based compound include, but are not limited to, 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, and 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropane-1-one.

Examples of the bisimidazole compound include 2, 2-bis (2-chlorophenyl) -4,4', 5' -tetraphenylbisimidazole and 2,2 '-bis (o-chlorophenyl) -4,4',5,5 '-tetrakis (3, 4, 5-trimethoxyphenyl) -1,2' -biimidazole, 2 '-bis (2, 3-dichlorophenyl) -4,4',5 '-tetraphenyl biimidazole, 2' -bis (o-chlorophenyl) -4, 5 '-tetraphenyl-1, 2' -biimidazole, and the like, but are not limited thereto.

The triazine compound may be 3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 1, 3-hexafluoroisopropyl-3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid ester, ethyl 2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetic acid ester, 2-epoxyethyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetic acid ester, cyclohexyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetic acid ester benzyl-2- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } acetic acid ester, 3- { chloro-4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanoic acid, 3- {4- [2, 4-bis (trichloromethyl) -s-triazin-6-yl ] phenylthio } propanamide, 2, 4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2, 4-bis (trichloromethyl) -6- (1-p-dimethylaminophenyl) -1, 3-butadiene-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, etc., but is not limited thereto.

Examples of the oxime-based compound include, but are not limited to, 1- (4-phenylthio) phenyl-1, 2-octanedione-2- (O-benzoyl oxime) (CIBA-GEIGY corporation, CGI 124), 1- (9-ethyl) -6- (2-methylbenzoyl-3-yl) -ethanone-1- (O-acetyl oxime) (CGI 242), and N-1919 (ADECA corporation).

The solvent is selected from acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, and 1, 4-diAlkane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1, 2-dichloroethane, 1-trichloroethane, 1, 2-trichloroethylene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tert-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, 3-ethoxypropyleneEthyl acetate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether.

In one embodiment of the present disclosure, the compound represented by the chemical formula 1 is contained in an amount of 5 to 60 wt%, the binder resin is contained in an amount of 1 to 60 wt%, the photopolymerization initiator is contained in an amount of 0.1 to 20 wt%, the polyfunctional monomer is contained in an amount of 0.1 to 50 wt%, and the solvent is contained in an amount of 10 to 80 wt%, based on the total weight of the photosensitive resin composition.

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

Specifically, in the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 5 to 50 wt%, the content of the binder resin is 1 to 50 wt%, the content of the photopolymerization initiator is 0.1 to 10 wt%, and the content of the polyfunctional monomer is 0.1 to 45 wt%, based on the total weight of solid components in the photosensitive resin composition.

The total weight of the solid components mentioned above means the sum of the total weights of the components other than the solvent in the resin composition. The basis of the solid content and the weight% of the solid content of each component can be measured by a general analytical means used in the field such as liquid chromatography or gas chromatography.

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

In one embodiment of the present specification, the photosensitive resin composition may further include an additive in an amount of 0.1 to 20 wt% based on the total weight of the photosensitive resin composition.

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

Specifically, the content of the additive is 0.1 to 10% by weight based on the total weight of the solid components in the photosensitive resin composition.

According to an embodiment of the present disclosure, the photosensitive resin composition further includes 1 or 2 or more additives selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.

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

According to an embodiment of the present disclosure, the photosensitive resin composition further includes 1 or 2 or more additives selected from the group consisting of a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a leveling agent.

The photocrosslinking sensitizer may be a benzophenone compound selected from the group consisting of benzophenone, 4-bis (dimethylamino) benzophenone, 4-bis (diethylamino) benzophenone, 2,4, 6-trimethylaminobenzophenone, methyl o-benzoylbenzoate, 3-dimethyl-4-methoxybenzophenone, and 3, 4-tetra (t-butylperoxycarbonyl) benzophenone; fluorenone compounds such as 9-fluorenone, 2-chloro-9-fluorenone, and 2-methyl-9-fluorenone; thioxanthone compounds such as thioxanthone, 2, 4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, and diisopropylthioxanthone; xanthone compounds such as xanthone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone, and 2, 6-dichloro-9, 10-anthraquinone; acridine compounds such as 9-phenylacridine, 1, 7-bis (9-acridinyl) heptane, 1, 5-bis (9-acridinyl pentane), and 1, 3-bis (9-acridinyl) propane; dicarbonyl compounds such as benzil, 1, 7-trimethyl-bicyclo [2, 1] heptane-2, 3-dione, and 9, 10-phenanthrenequinone; phosphine oxide compounds such as 2,4, 6-trimethylbenzoyl diphenyl phosphine oxide and bis (2, 6-dimethoxybenzoyl) -2, 4-trimethylpentylphosphine oxide; benzoate compounds such as methyl 4- (dimethylamino) benzoate, ethyl 4- (dimethylamino) benzoate, and 2-n-butoxyethyl-4- (dimethylamino) benzoate; amino synergists such as 2, 5-bis (4-diethylaminobenzylidene) cyclopentanone, 2, 6-bis (4-diethylaminobenzylidene) cyclohexanone, 2, 6-bis (4-diethylaminobenzylidene) -4-methyl-cyclopentanone, and the like; coumarin compounds such as 3, 3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7-methoxy-coumarin, and 10, 10-carbonylbis [1, 7-tetramethyl-2, 3,6, 7-tetrahydro-1 h,5h,11h-C1] -benzopyrano [6,7,8-ij ] -quinolizin-11-one; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzoyl acetophenone; and 1 or more of 3-methyl-b-naphthothiazoline.

The above-mentioned curing accelerator is used for curing and improving mechanical strength, and specifically, a curing accelerator selected from the group consisting of 2-mercaptobenzimidazole, 2-mercaptobenzothiazole may be usedMore than 1 of oxazole, 2, 5-dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate).

As the adhesion promoter used in the present specification, 1 or more kinds of methacryloyl silane coupling agents selected from methacryloxypropyl trimethoxysilane, methacryloxypropyl dimethoxy silane, methacryloxypropyl triethoxy silane, methacryloxypropyl dimethoxy silane and the like can be used, and as the alkyl trimethoxysilane, 1 or more kinds selected from octyl trimethoxysilane, dodecyl trimethoxysilane, octadecyl trimethoxysilane and the like can be used.

The above-mentioned surfactant is a silicon-based surfactant or a fluorine-based surfactant, and specifically, a silicon-based surfactant may be used, for example, BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307, BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-348, BYK-354, BYK-355, BYK-356, BYK-358, BYK-361, BYK-370, BYK-371, BYK-375, BYK-380, BYK-390, etc. as the fluorine-based surfactant, F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. of DIC (DaiNippon Ink & Chemicals) may be used, but are not limited thereto.

The antioxidant may be 1 or more selected from Hindered phenol (Hindered phenol) antioxidants, amine antioxidants, sulfur antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, and triethyl phosphate; such as 2, 6-di-tert-butyl-p-cresol, octadecyl-3- (4-hydroxy-3, 5-di-tert-butylphenyl) propionate, tetrakis [ methylene-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ] methane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-tert-butyl-4-hydroxybenzyl) benzene, diethyl 3, 5-di-tert-butyl-4-hydroxybenzyl phosphite, 2-thiobis (4-methyl-6-tert-butylphenol), 2,6-g, t-butylphenol 4,4' -butylidenebis (3-methyl-6-tert-butylphenol), 4' -thiobis (3-methyl-6-tert-butylphenol) or Bis [3,3-Bis- (4 ' -hydroxy-3' -t-butylphenyl) butyrate ] ethylene glycol ester (Bis [3, 3' -Bis- (4 ' -hydroxy-3' -t-phenolglucoside ] carboxylate); amine-based auxiliary antioxidants such as phenyl- α -naphthylamine, phenyl- β -naphthylamine, N '-diphenyl-p-phenylenediamine or N, N' -di- β -naphthyl-p-phenylenediamine; a sulfur-based auxiliary antioxidant such as dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzothiazole, or tetramethylthiuram disulfide tetrakis [ methylene-3- (laurylthio) propionate ] methane; or phosphite-based auxiliary antioxidants such as triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecyl phosphite, bis (2, 4-dibutylphenyl) pentaerythritol diphosphite (Bis (2, 4-ditbutylphenyl) Pentaerythritol Dip hosphite) or tetrakis [2,4-Bis (1, 1-dimethylethyl) phenyl ] phosphite ((1, 1 '-Biphenyl) -4,4' -Diylbisphosphonous acid tetrakis [2,4-Bis (1, 1-dimethylphenyl) phenyl ] ester).

As the ultraviolet absorber, 2- (3-tert-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone, and the like can be used, but are not limited thereto, and materials commonly used in the art can be used.

Examples of the thermal polymerization inhibitor include at least 1 selected from the group consisting of anisole, hydroquinone, catechol (pyrocatechol), t-butyl catechol (t-butyl catechol), ammonium salt of N-nitrosophenyl hydroxylamine, aluminum salt of N-nitrosophenyl hydroxylamine, p-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4-thiobis (3-methyl-6-t-butylphenol), 2-methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine (phenothiazine), but the thermal polymerization inhibitor generally known in the art may be included.

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

Specifically, the dispersant is 1 or more selected from polyalkylene glycols and esters thereof, polyoxyalkylene polyols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonates, carboxylic acid esters, carboxylates, alkylamide alkylene oxide adducts, and alkylamines, but is not limited thereto.

The leveling agent may be polymerizable or non-polymerizable. Specific examples of the polymerizable leveling agent include polyethyleneimine, polyamide-amine, and reaction products of amine and epoxide, and specific examples of the non-polymerizable leveling agent include a non-polymerizable sulfur-containing compound and a non-polymerizable nitrogen-containing compound, but the present invention is not limited thereto, and leveling agents commonly used in the field can be used.

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

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

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

Examples of the light source for curing the photosensitive resin composition according to the present specification include, but are not limited to, mercury vapor arc (arc), carbon arc, xe arc, and the like, which emit light having a wavelength of 250nm to 450 nm.

The photosensitive resin composition according to the present specification can be used for a pigment-dispersed photosensitive material for manufacturing a color filter of a thin film transistor liquid crystal display (TFT LCD), a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode, a photosensitive material for forming an overcoat layer, a photosensitive material for a column spacer, a photocurable coating, a photocurable ink, a photocurable adhesive, a printing plate, a photosensitive material for a printed wiring board, a photosensitive material for a Plasma Display Panel (PDP), and the like, but the use thereof is not particularly limited.

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

The color filter may be manufactured using a photosensitive resin composition including a compound represented by the chemical formula 1. The color filter can be formed by applying the photosensitive resin composition on a substrate to form a coating film, and exposing, developing and curing the coating film.

The photosensitive resin composition according to one embodiment of the present specification is excellent in heat resistance and little in color change due to heat treatment, and thus can provide a color filter having high color reproduction rate and high brightness and contrast even after a curing process in manufacturing the color filter.

The substrate may be a glass plate, a silicon wafer, a plastic substrate plate such as polyether sulfone (PES) or 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 can be applied to glass (5×5cm ² ) Spin coating (spin coating) was performed thereon, and a pre-bake treatment (prebake) was performed at 100℃for 100 seconds to form a film. The distance between the film-forming substrate and the photomask (photo mask) was set to 250 μm, and the entire surface of the substrate was irradiated with 40mJ/cm by an exposure machine ² Is a light exposure amount of (a). Then, the exposed substrate was developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and post-baking treatment (postrake) was performed at 230 ℃ for 20 minutes to produce a substrate.

The heat resistance evaluation may be performed by a method described below, and the substrate manufactured according to the above embodiment may be subjected to a spectrometer to obtain a transmittance spectrum in a visible light region ranging from 380nm to 780 nm. Further, the pre-baked (prebake) substrate was further subjected to post-baking (postrake) at 230 ℃ for 20 minutes, and a transmittance spectrum was obtained in the same apparatus and measurement range.

The spectrometer may be a spectrometer of the company MCPD-tsukamurella, but is not limited thereto.

The color change (hereinafter referred to as Δeab) is calculated using the transmittance spectrum obtained as described above and the C light source backlight, and using the obtained values E (L, a, b). A small ΔEab value indicates excellent color heat resistance. When Δeab <3, the pigment is used as a color filter pigment, and is said to be a coloring material having excellent heat resistance. Specifically, the expression of Δeab is calculated as follows.

[ calculation formula 1]

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

The contrast ratio can be measured by a method described below. The substrate manufactured by the substrate manufacturing method was placed between 2 polarizers by using a contrast measuring instrument, and the brightness when the 2 polarizers were horizontal and the brightness when the 2 polarizers were orthogonal were measured, and the contrast was calculated by the following expression 2.

[ calculation formula 2]

Contrast = brightness at 2-plate polarizer level/brightness at 2-plate polarizer perpendicular

The contrast measuring instrument may be a CT-1, ZOENTICH measuring instrument, but is not limited thereto.

Regarding the fluorescence intensity of the color filter according to an embodiment of the present specification, the fluorescence intensity can be measured by setting the excitation wavelength (excitation wavelength) to 545nm and the emission wavelength (emission wavelength) to 560nm to 720nm at normal temperature (25 ℃) using a Sinco FS-2 fluorescence measuring apparatus for the above-described substrate.

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

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

For the purpose of improving contrast, a lattice-like black pattern called a black matrix may be arranged between color pixels of the color filter. As a material of the black matrix, chromium may be used. In this case, chromium may be vapor deposited on the entire glass substrate and patterned by etching. However, in view of high cost in the process, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix obtained by a pigment dispersion method that can be micromachined can be used.

The black matrix may use a black pigment or a black dye as a coloring material. For example, carbon black alone or in combination with a coloring pigment may be used, and in this case, there is an advantage that the strength of the film or the adhesion to the substrate is not lowered even if the amount of the coloring material is relatively increased due to the mixing of a coloring pigment having insufficient light-shielding property.

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

The display device may be any one of a plasma display (Plasma Display Panel, PDP), a light emitting diode (Light Emitting Diode, LED), an organic light emitting element (Organic Light Emitting Diode, OLED), a liquid crystal display device (Liquid Crystal Display, LCD), a thin film transistor liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT), and a Cathode Ray Tube (CRT).

Modes for carrying out the invention

< example >

< synthetic example of Compound >

Synthesis example 1: synthesis of Compound 1

Synthesis of intermediate 1

5g (12.34 mmol) of A-1, 10.31g (74.03 mmol) of B-1 and 80g of N-Methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrosidone) are stirred in a 250ml two-necked round bottom flask (RBF, round Bottom Flask). After heating to 150℃and stirring for 4 hours, the reaction solution was cooled to room temperature, 800ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

Then, the obtained precipitate was filtered and washed under reduced pressure, and dried in a vacuum oven at 60℃for 12 hours, thereby obtaining 7g (11.46 mmol) of intermediate 1.

Ionization mode apci+: m/z=611 [ m+h ], exact Mass: 610

Synthesis of Compound 1

1.5g (2.46 mmol) of intermediate 1, 2.958g (9.82 mmol) of C-1, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes. The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography and dried in a vacuum oven at 60℃for 12 hours to give 1.3g (1.358 mmol) of compound 1.

Ionization mode apci+: m/z=957 [ m+h ], exact Mass: 956

Synthesis example 2: synthesis of Compound 2

Synthesis of intermediate 2

5g (12.34 mmol) of A-1, 14.90g (74.03 mmol) of B-2 and 80g of N-Methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrosidone) are stirred in a 250ml two-necked round bottom flask (RBF, round Bottom Flask). After heating to 150℃and stirring for 4 hours, the reaction solution was cooled to room temperature, 800ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

Then, the precipitate was filtered and washed with water under reduced pressure, and dried in a vacuum oven at 60℃for 12 hours, thereby obtaining 7.2g (9.80 mmol) of intermediate 2.

Ionization mode apci+: m/z=735 [ m+h ], exact Mass (Exact Mass): 734

Synthesis of Compound 2

1.808g (2.46 mmol) of intermediate 2, 2.958g (9.82 mmol) of C-1, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

Then, the obtained precipitate was filtered under reduced pressure and washed with water, separated by column chromatography, and dried in a vacuum oven at 60℃for 12 hours, whereby 1g (0.925 mmol) of compound 2 was obtained.

Ionization mode apci+: m/z=1081 [ m+h ], exact Mass: 1081

Synthesis example 3: synthesis of Compound 3

Synthesis of intermediate 3

5g (12.34 mmol) of A-1, 10.31g (74.03 mmol) of B-3 and 80g of N-Methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrosidone) are stirred in a 250ml two-necked round bottom flask (RBF, round Bottom Flask). After heating to 150℃and stirring for 4 hours, the reaction solution was cooled to room temperature, 800ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

Then, the precipitate was filtered and washed with water under reduced pressure, and dried in a vacuum oven at 60℃for 12 hours, thereby obtaining 6.8g (11.130 mmol) of intermediate 3.

Ionization mode apci+: m/z=611 [ m+h ], exact Mass: 610

Synthesis of Compound 3

1.502g (2.46 mmol) of intermediate 3, 2.958g (9.82 mmol) of C-1, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

Then, the precipitate was filtered under reduced pressure and washed with water, separated by column chromatography, and dried in a vacuum oven at 60℃for 12 hours, whereby 1.4g (1.463 mmol) of compound 3 was obtained.

Ionization mode apci+: m/z=957 [ m+h ], exact Mass: 956

Synthesis example 4: synthesis of Compound 4

Synthesis of intermediate 4

5g (12.34 mmol) of A-1, 10.31g (74.03 mmol) of B-4 and 80g of N-Methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrosidone) are stirred in a 250ml two-necked round bottom flask (RBF, round Bottom Flask). After heating to 150℃and stirring for 4 hours, the reaction solution was cooled to room temperature, 800ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

Then, the precipitate was filtered and washed with water under reduced pressure, and dried in a vacuum oven at 60℃for 12 hours, thereby obtaining 6.5g (10.64 mmol) of intermediate 4.

Ionization mode apci+: m/z=611 { m+h ], exact Mass (Exact Mass): 610

Synthesis of Compound 4

1.502g (2.46 mmol) of intermediate 4, 2.958g (9.82 mmol) of C-1, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography and dried in a vacuum oven at 60 ℃ for 12 hours to give 1.7g (1.776 mmol) of compound 4.

Ionization mode apci+: m/z=957 [ m+h ], exact Mass: 956

Synthesis example 5: synthesis of Compound 5

Synthesis of intermediate 5

In a 250ml two-necked round bottom flask (RBF, round Bottom Flask) were added 5g (12.34 mmol) of A-1, 14.30g (74.03 mmol) of B-5 and 80g of N-Methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrosidone) and stirred. After heating to 150℃and stirring for 4 hours, the reaction solution was cooled to room temperature, 800ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

Then, the precipitate was filtered and washed with water under reduced pressure, and dried in a vacuum oven at 60℃for 12 hours, thereby obtaining 7.2g (10.02 mmol) of intermediate 5.

Ionization mode apci+: m/z=719 [ m+h ], exact Mass (Exact Mass): 718

Synthesis of Compound 5

1.768g (2.46 mmol) of intermediate 5, 2.958g (9.82 mmol) of C-1, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography and dried in a vacuum oven at 60℃for 12 hours to give 2.1g (1.972 mmol) of compound 5.

Ionization mode apci+: m/z=1065 [ m+h ], exact Mass (Exact Mass): 1064

Synthesis example 6: synthesis of Compound 6

Synthesis of intermediate 6

In a 250ml two-necked round bottom flask (RBF, round Bottom Flask) were added 5g (12.34 mmol) of A-1, 15.33g (74.03 mmol) of B-6 and 80g of N-Methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrosidone) and stirred. After heating to 150℃and stirring for 4 hours, the reaction solution was cooled to room temperature, 800ml of 1M hydrochloric acid (HCl) was added and stirred for 30 minutes.

The precipitate was filtered and washed with water under reduced pressure and dried in a vacuum oven at 60℃for 12 hours, thus obtaining 7.4g (9.91 mmol) of intermediate 6.

Ionization mode apci+: m/z=747 [ m+h ], exact Mass (Exact Mass): 746

Synthesis of Compound 6

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1.837g (2.46 mmol) of intermediate 6, 2.958g (9.82 mmol) of C-1, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography and dried in a vacuum oven at 60℃for 12 hours, whereby 2.5g (2.287 mmol) of compound 6 was obtained.

Ionization mode apci+: m/z=1093 [ m+h ], exact Mass: 1092

Synthesis example 7: synthesis of Compound 7

Compound 7 was obtained by the same method as in the production of compound 1 above except that C-1 was changed to C-2.

Ionization mode apci+: m/z=985 [ m+h ], exact Mass: 984

Synthesis example 8: synthesis of Compound 8

Compound 8 was obtained by the same method as that for the production of compound 2 described above, except that C-1 was changed to C-2.

Ionization mode apci+: m/z=1109 [ m+h ], exact Mass: 1108

Synthesis example 9: synthesis of Compound 9

Compound 9 was obtained by the same method as in the production of compound 3 described above, except that C-1 was changed to C-2.

Ionization mode apci+: m/z=985 [ m+h ], exact Mass: 984

Synthesis example 10: synthesis of Compound 10

Compound 10 was obtained by the same method as in the production of compound 4 above except that C-1 was changed to C-2.

Ionization mode apci+: m/z=985 [ m+h ], exact Mass: 984

Synthesis example 11: synthesis of Compound 11

Compound 11 was obtained by the same method as that for the production of compound 5 described above, except that C-1 was changed to C-2.

Ionization mode apci+: m/z=1093 [ m+h ], exact Mass: 1092

Synthesis example 12: synthesis of Compound 12

Compound 12 was obtained by the same method as in the production of compound 6 above except that C-1 was changed to C-2.

Ionization mode apci+: m/z=1121 [ m+h ], exact Mass (Exact Mass): 1120

Synthesis examples 13 to 18: synthesis of Compounds 13 to 18

Compounds 13 to 18 shown below were obtained in the same manner except that C-1 was changed to C-3 in the production of compounds 1 to 6.

Compound 13: ionization mode apci+: m/z=1085 [ m+h ], exact Mass (Exact Mass): 1084

Compound 14: ionization mode apci+: m/z=1209 [ m+h ], exact Mass (Exact Mass): 1208

Compound 15: ionization mode apci+: m/z=1085 [ m+h ], exact Mass (Exact Mass): 1084

Compound 16: ionization mode apci+: m/z=1085 [ m+h ], exact Mass (Exact Mass): 1084

Compound 17: ionization mode apci+: m/z=1193 [ m+h ], exact Mass (Exact Mass): 1192

Compound 18: ionization mode apci+: m/z=1221 [ m+h ], exact Mass: 1220

Compound 1 was compared.

In a 100ml two-necked round bottom flask (RBF, round Bottom Flask), 1.414g (2.46 mmol) of S1, 1.21g (9.82 mmol) of bromopropane, 1.358g (9.82 mmol) of potassium carbonate (K ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography, and dried in a vacuum oven at 60 ℃ for 12 hours, to give comparative compound 1.

Ionization mode apci+: m/z=659 [ m+h ], exact Mass: 658

Comparative Compound 2

1.4234g (2.46 mmol) of S2, 3.094g (9.82 mmol) of C-2, 1.358g (9.82 mmol) of potassium carbonate (K) are combined in a 100ml two-necked round bottom flask (RBF, round Bottom Flask) ₂ CO ₃ ) To 30g of N-Methyl-2-pyrrolidone (NMP) was added and stirred. After the temperature was raised to 100℃and stirred for 6 hours, the reaction solution was cooled to room temperature, 500ml of distilled Water (DI-Water) was added and stirred for 30 minutes.

The precipitate was filtered under reduced pressure and washed with water, separated by column chromatography, and dried in a vacuum oven at 60 ℃ for 12 hours, to give comparative compound 2.

Ionization mode apci+: m/z=953 [ m+h ], exact Mass: 952

Comparative Compound 3

In Synthesis example 1, comparative compound 3 was synthesized by the same method as the synthesis of intermediate 1, using S3 and S4 instead of A-1 and B-1.

Comparative Compound 4

To 50g of 98% sulfuric acid at 10℃was added 3g (4.553 mmol) of comparative compound 1 for dissolution. Then, 0.807g (4.553 mmol) of N-hydroxymethylphthalimide (N-hydroxymethylphthalimide) was added thereto, and the temperature was raised to 45℃and stirred for 2 hours. The reaction solution was added to 500g of water to precipitate crystals, and the precipitate was filtered under reduced pressure to obtain comparative compound 4.

Example 1

5.554g of compound 1, 10.376g of a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113KOH mg/g, weight average molecular weight 20000g/mol as measured by Gel Permeation Chromatography (GPC), molecular weight distribution (PDI) 2.0g, solid content (S.C) 25%, containing solvent Polypropylene Glycol Monomethyl Ether Acetate (PGMEA)), 2.018g of I-369 (BASF corporation) as a photopolymerization initiator, 12.443g of DPHA (Japanese chemical) as a polyfunctional monomer, 68.593g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016g of F-475 as an additive were mixed to produce photosensitive resin composition 1.

Examples 2 to 18

In example 1, photosensitive resin compositions 2 to 18 were produced with the same composition except that compound 1 was changed to compounds 2 to 18.

Comparative example 1

5.554g of a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio: 70:30, acid value: 113KOH mg/g, weight average molecular weight: 20000g/mol as measured by Gel Permeation Chromatography (GPC), molecular weight distribution (PDI) 2.0g, solid content (S.C) 25%, containing solvent Polypropylene Glycol Monomethyl Ether Acetate (PGMEA)), 2.018g of I-369 (BASF corporation) as a photopolymerization initiator, 12.443g of DPHA (Japanese chemical), as a polyfunctional monomer, 68.593g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016g of F-475 as an additive of surfactant DIC were mixed to produce a photosensitive resin composition of comparative example 1.

Comparative examples 2 to 4

In comparative example 1, photosensitive resin compositions of comparative examples 2 to 4 were produced with the same composition except that comparative compound 1 was changed to comparative compounds 2 to 4, respectively.

< Experimental example >

Substrate fabrication

The photosensitive resin compositions according to examples 1 to 18 and comparative examples 1 to 4 described above were used for substrate production, respectively. Specifically, the photosensitive resin compositions according to examples 1 to 18 and comparative examples 1 to 4 described above were mixed in glass (5×5 cm) ² ) Spin coating (spin coating) was performed thereon, and a pre-bake treatment (prebake) was performed at 100℃for 100 seconds to form a film.

The distance between the film-forming substrate and the photomask (photo mask) was set to 250 μm, and the entire surface of the substrate was irradiated with 40mJ/cm by an exposure machine ² Is a light exposure amount of (a). Then, the exposed substrate was developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and post-baking treatment (post-baking) was performed at 230 ℃ for 20 minutes to produce a substrate.

Evaluation of Heat resistance

The substrate manufactured by the substrate manufacturing method described above was subjected to a spectrum of transmittance in the visible light region ranging from 380nm to 780nm by a spectrometer (MCPD-tsukamu corporation). Further, the pre-baked (prebake) substrate was further subjected to post-baking (post-baking) at 230 ℃ for 20 minutes, and a transmittance spectrum was obtained in the same equipment and measurement range.

The color change (hereinafter referred to as Δeab) was calculated using the obtained transmittance spectrum and the C light source backlight and using the obtained values E (L, a, b), and is shown in table 1 below.

A small ΔEab value indicates excellent color heat resistance.

When ΔEab < 3, the pigment can be used as a coloring material for color filters, and is said to have excellent heat resistance. Specifically, the expression of Δeab is calculated as follows.

[ calculation formula 1]

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

TABLE 1

	ΔEab (post-baking treatment-pre-baking treatment)
		Example 1	1.28
Example 2	1.27
		Example 3	0.85
Example 4	1.36
		Example 5	1.75
Example 6	0.94
		Example 7	1.45
Example 8	1.39
		Example 9	1.12
Example 10	1.47
		Example 11	1.68
Example 12	1.27
		Example 13	0.97
Example 14	1.54
		Example 15	1.98
Example 16	1.76
		Example 17	1.64
Example 18	1.44

Referring to table 1 above, the color pattern substrates formed using the photosensitive resin compositions of examples 1 to 18 of the present invention were confirmed to have high color stability and excellent heat resistance, with the difference (Δeab) between the transmission spectra after the post-baking treatment and the post-baking treatment being less than 3.

Contrast determination

The substrate manufactured by the substrate manufacturing method was placed between 2 polarizers using a contrast measuring instrument (CT-1, zoentech corporation), and the brightness at the level of 2 polarizers were measured, and the contrast was calculated by the following expression 2.

[ calculation formula 2]

The contrast improvement rate calculated by the above-described calculation formula 2 is calculated by the following calculation formula 3, and is shown in table 2 below.

[ calculation formula 3]

Contrast improvement ratio= (contrast of example-contrast of comparative example 1, 2 or 4)/contrast of comparative example 1, 2 or 4 ×100

TABLE 2

Referring to table 2 above, it was confirmed that the contrast of examples 1 to 18 was improved by 220.47% to 532.38% as compared with comparative example 1 above. Further, it was confirmed that the contrast of the above-described examples 1 to 18 was improved by 136.48% to 329.57% as compared with the above-described comparative example 2. Further, it was confirmed that the contrast of the above-described examples 1 to 18 was improved by 197.83% to 510.43% as compared with the above-described comparative example 4.

Determination of fluorescence intensity

The fluorescence intensity of the substrate manufactured by the substrate manufacturing method was measured by using a Sinco FS-2 fluorescence measuring apparatus at normal temperature (25 ℃) with an excitation wavelength (excitation wavelength) of 545nm and an emission wavelength (emission wavelength) of 560nm to 720nm, and is shown in FIG. 1.

From fig. 1, it was confirmed that the fluorescence intensities of examples 6, 7 and 12 according to one embodiment of the present specification were lower than those of comparative examples 1 and 2, and that excellent contrast was obtained without adding additional dye.

Transmittance evaluation

The substrate manufactured by the substrate manufacturing method was subjected to post-baking treatment (postrake) at 230 ℃ for 20 minutes by a spectrometer (MCPD-tsukamu corporation), thereby obtaining a transmittance spectrum in the visible light region ranging from 380nm to 780 nm.

Particularly, in the case of a blue color filter, it is possible to exhibit more excellent brightness in the case of a high maximum transmittance at 380nm to 480nm in the visual x, visual y, visual z directions.

Fig. 2 shows vision x, vision y, vision z.

TABLE 3

	Transmittance% (maximum transmittance at 380nm to 480 nm)
		Example 1	95.756
Example 7	92.906
		Example 13	95.721
Comparative example 3	88.528

Referring to Table 3, it is understood that the maximum transmittance at 380nm to 480nm was higher in examples 1, 7 and 13 than in comparative example 3.

As can be confirmed from fig. 3, the transmittance at 380nm to 480nm of examples 1, 7 and 13 according to an embodiment of the present specification is greater than that of comparative example 3, and more excellent brightness can be exhibited in the blue color filter.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1 described above, a compound having the formula,

l1 and L2 are the same or different from each other and each independently is a straight-chain or branched alkylene group having 1 to 20 carbon atoms,

r3 and R4 are the same or different and each independently is an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with a halogen group or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a halogen group,

r5 to R6 are identical to or different from each other and are each independently selected from hydrogen, deuterium, a halogen group, -SO ₂ NHY, or an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with a halogen group,

r7 to R12 are identical to or different from each other and are each independently selected from hydrogen or deuterium,

r13 to R17 are identical to or different from each other and are each independently hydrogen, deuterium, a halogen group, -SO ₃ ^- 、-SO ₃ M, -or-SO ₂ NHY，

The M is selected from Na ⁺ 、K ⁺ 、Rb ⁺ 、Cs ⁺ 、Fr ⁺ And a moiety comprising an ammonium structure,

y is an alkyl group having 1 to 20 carbon atoms,

at least one of R13 to R17 is-SO ₃ ^- ，

X is an anionic group and is preferably a hydroxyl group,

a is 0, and a is not shown,

r5 and R6 are integers of 0 to 4, R5 is the same as or different from each other when R5 is 2 or more, R6 is the same as or different from each other when R6 is 2 or more,

wherein the dianhydride group containing a nitrogen atom is represented by any one of the following substituents:

among the substituents, the substituents mentioned above are those,represents a site to which L1 or L2 in the chemical formula 1 is bonded,

X3 to X5 and Y4 are identical to or different from each other and are each independently hydrogen, deuterium, -SO ₃ M, or-SO ₂ NHY, where M and Y are as defined in chemical formula 1, x3 is an integer of 0 to 4, and x4, x5 and Y4 are integers of 0 to 6.

2. The compound according to claim 1, wherein,

the moiety comprising an ammonium structure comprises a unit represented by the following formula a or by the following formula B:

chemical formula A

Chemical formula B

In the chemical formula a, in which the amino acid is represented by the formula a,

ra to Rd are the same or different from each other and are each independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, aralkyl having 6 to 20 carbon atoms, -L ₁ -NHCO-R, or-L ₂ -OCO-R，

R is hydrogen, alkyl of 1 to 20 carbon atoms, aryl of 6 to 20 carbon atoms, or aralkyl of 6 to 20 carbon atoms,

the L is ₁ And L ₂ Is an alkylene group having 1 to 20 carbon atoms,

in the chemical formula B, in which the amino acid is represented by the formula,

rb to Rd are the same or different from each other and are each independently hydrogen, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 6 to 20 carbon atoms,

z is an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, -L ₃ -NHCO-, or-L ₄ -OCO-，

The L is ₃ And L ₄ Is an alkylene group having 1 to 20 carbon atoms,

re to Rg are the same or different from each other and are each independently hydrogen or an alkyl group having 1 to 20 carbon atoms.

3. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2:

chemical formula 2

In the chemical formula 2 described above, the chemical formula,

l1, L2, R1 to R17, X, a, R5 and R6 are as defined in the chemical formula 1.

4. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3:

chemical formula 3

In the chemical formula 3 described above, the chemical formula,

l1, L2, R1 to R17, X, a, R5 and R6 are as defined in the chemical formula 1.

5. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4:

chemical formula 4

In the chemical formula 4 described above, the chemical formula,

l1, L2, R1 to R17, X, a, R5 and R6 are as defined in the chemical formula 1.

6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas:

/>

in the chemical formula (II), in the formula (II),

m and Y are as defined in the chemical formula 1.

7. A photosensitive resin composition comprising the compound according to any one of claims 1 to 6, a binder resin, a polyfunctional monomer, a photopolymerization initiator, and a solvent.

8. The photosensitive resin composition according to claim 7, wherein the content of the compound represented by chemical formula 1 is 5 to 60% by weight based on the total weight of solid components in the photosensitive resin composition,

the content of the binder resin is 1 to 60 wt%,

the content of the photopolymerization initiator is 0.1 to 20 wt%,

the content of the polyfunctional monomer is 0.1 to 50% by weight.

9. The photosensitive resin composition according to claim 7, further comprising an additive.

10. A photosensitive material produced using the resin composition according to claim 7.

11. A color filter comprising the photosensitive material of claim 10.

12. A display device comprising the color filter of claim 11.