KR20190116897A - Xanthene-based compound photosensitive resin composition, photoresist, color filter, and display device comprising the same - Google Patents

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 apparatus comprising the same. A xanthene-based compound according to an embodiment of the present specification can be used as a color material to improve color reproduction, brightness, and a contrast ratio.

Description

Xanthene-based compound, photosensitive resin composition, photosensitive material, color filter, and display device including the same TECHNICAL FIELD

This application claims the benefit of the application date of Korean Patent Application No. 10-2018-0039901 filed with the Korea Intellectual Property Office on April 05, 2018, the entire contents of which are incorporated herein.

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

In recent years, the performance of the color filter characterized by high brightness and high contrast ratio has been demanded. In addition, one of the main purposes of the display device development is to differentiate the display device performance through the improvement of color purity and to improve the productivity in the manufacturing process.

Since the pigment type conventionally used as the color material of the color filter exists in the color photoresist in the state of particle dispersion, it is difficult to control the brightness and contrast ratio according to the pigment particle size and distribution control. In the case of pigment particles, the light particles are aggregated in the color filter, resulting in poor dissolution and dispersibility, and multiple scattering of light occurs due to the aggregation of large particles. The scattering of the polarized light has been pointed out as a main factor for decreasing the contrast ratio. Efforts have been made to improve the luminance and contrast ratio through ultrafine atomization and dispersion stabilization of pigments, but the degree of freedom in selecting colorants to implement color coordinates for high color purity display devices is limited. In addition, the pigment dispersion method using the already developed color material, especially pigment has reached the limit to improve the color purity, brightness and contrast ratio of the color filter using the same.

Accordingly, there is a demand for the development of a new color material that can improve color purity and improve color reproduction, brightness, and contrast ratio.

Korean Laid-Open Patent No. 2001-0009058

The present inventors provide a xanthene compound having a novel structure, a photosensitive resin composition comprising the same, a photosensitive material manufactured using the same, a color filter, and a display device including the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

L1 and L2 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,

R1 and R2 are the same or different from each other, and each independently a dianhydride group containing a nitrogen atom,

R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

R5 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; -OH; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; -COOH; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,

R13 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; -OH; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; -COOH; Anionic group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

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

M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group, at least one of R13 to R17 is an anionic group,

X is an anionic group,

a is 0 or 1,

r5 and r6 are integers of 0 to 4, and when R5 is 2 or more, R5 is the same or different from each other. When r6 is 2 or more, R6 is the same or different from each other.

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

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

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

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

The compound according to one embodiment of the present specification may be used as a colorant in the photosensitive resin composition, and may have a solubility in an organic solvent, thereby reducing a dispersing process, unlike when a conventional pigment is applied, a dispersion process may be required. Compounds can be used as colorants in an economical way. In addition, by reducing the fluorescence intensity, the contrast ratio can be improved without additionally adding a dye.

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

1 is a view showing the detected fluorescence intensity of a substrate prepared using a compound according to some embodiments and comparative examples of the present specification.
Figure 2 illustrates the ligation of the compound according to one embodiment of the present specification.
Figure 3 shows the transmittance of the substrate prepared using the compound according to some examples and comparative examples of the present specification.

Hereinafter, this specification is demonstrated in detail.

In this specification, when a member is located “on” another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

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

The present invention has excellent solubility in organic solvents by including the compound represented by the formula (1). Specifically, Chemical Formula 1 is an organic solvent, in which an aryl group substituted with nitrogen having a xanthene structure is substituted with a substituent including sulfur (S), and includes a bulky substituent such as a dianhydride group containing a nitrogen atom. Solubility in

In addition, when the aryl group substituted in the nitrogen of the xanthene structure is substituted with a substituent containing sulfur (S), the formula 1 is reduced in fluorescence intensity than when substituted with a substituent containing no sulfur (S), further dye Excellent contrast ratio can be obtained without adding.

As a result, the solubility is increased, so that aggregation between color materials can be prevented, and economic efficiency can be improved by reducing the amount of material required for dispersing the color materials.

In addition, contrast ratio (CR) can be improved and excellent heat resistance can be obtained. In order to reduce the light emission (fluorescence or phosphorescence) of the molecule, there is a method of reducing the planarity in the molecule or introducing a molecule to absorb the light emission. When a molecule that absorbs light emission is introduced, it is difficult to selectively absorb only light of an emission wavelength because it absorbs both light and external light of a desired light emitting molecule. Thus, in order to reduce the planarity in the molecule, a bulky group having a steric hindrance is introduced.

Non-radiative decay occurs when a molecule that absorbs light in the ground state and enters an excited state transfers energy through a vibration mode or a rotation mode. Can happen. That is, the emission can be reduced.

The greater the planarity, the more difficult the radiant radiation is, so that the intensity of light emission increases, and as the planar area is reduced by introducing a large substituent, the intensity of light emission can be reduced through the non-radiative radiation. Longer alkyl groups, branched alkyl groups, alkoxy groups and amine groups can be introduced for non-radiative radiation. However, alkyl has a disadvantage in that heat resistance is insufficient.

In addition, alkoxy and amine groups can act as electron donation groups to change the absorption wavelength of light absorbing molecules.

In contrast, when a molecule including sulfur (S) is introduced, a role of an electron donating group in the light absorbing molecule may be reduced, and heat resistance may be maintained.

When introducing a sulfur atom having a larger atomic size than carbon, nitrogen, and oxygen, the energy of the excited molecule is transferred to a sulfur atom having various energy levels. Non-radiative decay may occur while moving, ie moving along a vibration mode, a rotation mode. Due to these characteristics, the introduction of sulfur atoms can reduce the intensity of luminescence in the molecule.

When a light emitting molecule is applied to a liquid crystal display (LCD), it may cause a decrease in contrast ratio (CR), which may be a problem of deterioration of quality. Therefore, various approaches have been taken to reduce the light emission.

Currently, molecules are absorbed to absorb light emission in order to suppress a decrease in contrast ratio (CR). However, there is a decrease in color purity and an increase in colorant usage.

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

및

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

And

Means a site which is bonded to another substituent or binding moiety.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; -OH; Carbonyl group; Ester group; -COOH; Imide group; Amide group; Anionic group; An alkoxy group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Cycloalkenyl group; Arylalkyl group; Phosphine groups; Sulfonate groups; Amine group; Aryl group; Heteroaryl group; Silyl groups; Boron group; Acryloyl group; Acrylate group; Ether group; It means that it is substituted with one or more substituents selected from the group comprising an anionic group and a heterocyclic group containing one or more of N, O, S or P atoms or have no substituents.

As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, the ring refers to an aromatic or aliphatic ring in that adjacent groups can combine to form a “ring”. Specifically, the ring may be an aromatic ring, it may be an aryl group or a heteroaryl group. The following description may be applied to the aryl group and heteroaryl group.

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

In the present specification, the carbonyl group may be represented by -COR, and R is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group. Although carbon number of the said carbonyl group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

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

In the present specification, the phosphine group means an alkyl phosphine group or an aryl phosphine group, and the alkyl phosphine group means a phosphine group substituted with an alkyl group. Although carbon number of the said alkyl phosphine group is not specifically limited, It is preferable that it is 1-20. Examples of the alkylphosphine group include dimethylphosphine group, diethylphosphine group, di-n-propylphosphine group, diisopropylphosphine group, di-n-butylphosphine group, di-sec-butylphosphine group and di-tert. -Butyl phosphine group, diisobutyl phosphine group, tert- butyl isopropyl phosphine group, di-n-hexyl phosphine group, di-n-octyl phosphine group, di-n- mesyl phosphine group and the like, but is not limited thereto . The arylphosphine group refers to a phosphine group substituted with an aryl group. Although carbon number of the said aryl phosphine group is not specifically limited, It is preferable that it is 6-30. Examples of the arylphosphine group include, but are not limited to, a diphenylphosphine group, a dibenzylphosphine group, a methylphenylphosphine group, a benzylhexylphosphine group, a bistrimethylsilylphosphine group, and the like.

In the present specification, the anionic group has a chemical bond with the structure of Formula 1, and the chemical bond may mean an ionic bond. The anionic group is not particularly limited, and for example, US Patent No. 7,939,644, Japanese Patent Laid-Open No. 2006-003080, Japanese Patent Laid-Open 2006-001917, Japanese Patent Laid-Open No. 2005-159926, Japanese Patent Laid-Open No. 2007-7028897, Japan The anions described in Japanese Patent Application Laid-Open No. 2005-071680, Korean Patent Application Publication No. 2007-7000693, Japanese Patent Application No. 2005-111696, Japanese Patent Application No. 2008-249663, and Japanese Patent Application No. 2014-199436 can be applied.

Specific examples of the anionic group include trifluoromethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethane sulfonyl nilme suited _{^{to, SO 3 -, CO 2 -}} , SO 2 N - SO 2 CF 3, SO 2 N ^- SO ₂ CF ₂ CF _3, but include a halogen group such as fluorine group, an iodo group, a chlorine group, it is not limited thereto.

In the present specification, the anionic group may have an anion per se, or may exist in complex form with other cations. Therefore, the sum of the total charge of the compound molecules of the present invention may vary depending on the number of substituted anionic groups. For example, if Formula 1 includes an ammonium structure, the total charge of the molecule may have a value from an anion to 0 minus 1 from the number of substituted anionic groups since the ammonium structure has a cation. have.

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

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group and n-jade And the like, but are not limited thereto. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and particularly preferably cyclopentyl group and cyclohexyl group, but is not limited thereto. .

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

In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 60. According to an exemplary embodiment, the alkyl group has 2 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 2 to 10 carbon atoms. Specific examples of the alkenyl group include, but are not limited to, alkenyl groups substituted with aryl groups such as stylbenyl and styrenyl groups.

In the present specification, the cycloalkenyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Examples of the cycloalkenyl group include, but are not limited to, a cyclopentenylene group and a cyclohexenylene group.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perrylenyl group, triphenyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group). However, the present invention is not limited thereto.

In the present specification, the arylalkyl group may specifically include an aryl portion having 6 to 30 carbon atoms and an alkyl portion having 1 to 30 carbon atoms. Specific examples include benzyl group, p-methylbenzyl group, m-methylbenzyl group, p-ethylbenzyl group, m-ethylbenzyl group, 3,5-dimethylbenzyl group, α-methylbenzyl group, α, α-dimethylbenzyl Group, α, α-methylphenylbenzyl group, 1-naphthylbenzyl group, 2-naphthylbenzyl group, p-fluorobenzyl group, 3,5-difluorobenzyl group, α, α-ditrifluoromethylbenzyl group , p-methoxybenzyl group, m-methoxybenzyl group, α-phenoxybenzyl group, α-benzyl groupoxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, pyrrole Ethyl group, aminobenzyl group, nitrobenzyl group, cyanobenzyl group, 1-hydroxy-2-phenyl isopropyl group, 1-chloro-2-phenyl isopropyl group and the like, but is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N or S as a hetero atom, and the carbon number is not particularly limited, but is 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridil group, pyridazine group , Quinolinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran And the like, but are not limited thereto.

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

In the present specification, the silyl group may be represented by a chemical formula of -SiZ1Z2Z3, wherein Z1, Z2 and Z3 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group (TMS), triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It is not limited to this.

In the present specification, the alkyl sulfoxy group includes methyl sulfoxy group, ethyl sulfoxy group, propyl sulfoxy group, butyl sulfoxy group, and the like, but is not limited thereto. The alkyl group in the alkyl sulfoxy group may be applied to the description of the alkyl group described above.

In the present specification, the boron group may be represented by the formula of -BW4W5, wherein W4 and W5 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.

In the present specification, the acryloyl group means a photopolymerizable unsaturated group, and for example, (meth) acryloyl group may be mentioned, but is 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 this specification, "(meth) acryloyl" represents at least 1 sort (s) chosen from the group which consists of acryloyl and methacryloyl. The description of '(meth) acrylate' also has the same meaning.

In the present specification, the ether group may be represented by -COR. R is a substituted or unsubstituted alkyl group. The alkyl group may be applied to the description of the alkyl group described above.

In the present specification, the sulfonate group may be an alkylsulfonate group or an arylsulfonate group. The description of the aforementioned alkyl group may be applied to the 'alkyl', and the description of the aforementioned aryl group may be applied to the 'aryl'.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-alkylarylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. A diphenylamine group, an N-phenylnaphthylamine group, a tolylamine group, an N-phenyltolylamine group, a triphenylamine group, and an N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenyl amine group and the like, but is not limited thereto.

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

In the present specification, an alkylene group means that there are two bonding positions in an alkane. The alkylene group may be straight, branched or cyclic. Although carbon number of an alkylene group is not specifically limited, For example, it is C1-C30, Specifically, 1-20, More specifically, it is 1-10.

In the present specification, the heteroalkylene group means that there are two bonding positions in an alkane including O, N or S as a hetero atom. The heteroalkylene group may be linear, branched or cyclic. Although carbon number of a heteroalkylene group is not specifically limited, For example, it is C2-C30, Specifically, it is C2-C20, More specifically, it is C2-C10.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkylene group.

In one embodiment of the present specification, L1 and L2 of Chemical Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkylene group having 1 to 30 carbon atoms.

In one embodiment of the present specification, L1 and L2 of Chemical Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkylene group having 1 to 20 carbon atoms.

In one embodiment of the present specification, L1 and L2 of Chemical Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted linear or branched alkylene group having 1 to 10 carbon atoms.

In one embodiment of the present specification, L1 and L2 of Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted methylene group; Substituted or unsubstituted ethylene group; Substituted or unsubstituted propylene group; Or a substituted or unsubstituted butylene group.

In one embodiment of the present specification, L1 and L2 of Formula 1 are the same as or different from each other, and each independently methylene group; Ethylene group; Propylene group; Or butylene group.

In an exemplary embodiment of the present specification, R1 and R2 of the general formula (1) are the same as or different from each other, and each independently an dianhydride group including a nitrogen atom having 4 to 30 carbon atoms.

In one embodiment of the present specification, R1 and R2 of the general formula (1) are the same as or different from each other, and each independently a dianhydride group containing a nitrogen atom of 4 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2 of the general formula (1) are the same as or different from each other, and each independently a dianhydride group containing a nitrogen atom of 4 to 15 carbon atoms.

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

는 상기 화학식 1에 연결되는 부위를 나타내고, In the substituent,

Represents a site linked to the formula (1),

X1, X2 and Y1 to Y3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; -OH; -SO ₃ H ;; -COOH; Phosphine groups; Anionic group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine to form a substituted or unsubstituted ring.

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

In one embodiment of the present specification, X1 and X2 are bonded to each other to form a substituted or unsubstituted benzene ring; Or a substituted or unsubstituted naphthalene ring.

In one embodiment of the present specification, X1 and X2 are combined with each other -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY; Or -SO ₃ M; Or it may form a substituted or unsubstituted naphthalene ring with -SO ₂ NHY, wherein M and Y are as defined in the formula (1).

In one embodiment of the present specification, X1 and X2 are combined with each other -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY; Or -SO ₃ M; Or a naphthalene ring unsubstituted or substituted with -SO ₂ NHY, wherein M is hydrogen; Na; K; Rb; Cs; Fr; And it is selected from the group consisting of a compound containing an ammonium structure, wherein Y is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, X1 and X2 are combined with each other -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY; Or -SO ₃ M; Or a naphthalene ring unsubstituted or substituted with -SO ₂ NHY, wherein M is hydrogen; Na; K; Rb; Cs; Fr; And it is selected from the group consisting of a compound containing an ammonium structure, wherein Y is a substituted or unsubstituted n-hexyl group.

In one embodiment of the present specification, X1 and X2 are combined with each other -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY; Or -SO ₃ M; Or a naphthalene ring unsubstituted or substituted with -SO ₂ NHY, wherein M is hydrogen; Na; K; Rb; Cs; Fr; And it is selected from the group consisting of a compound containing an ammonium structure, wherein Y is an n-hexyl group substituted with an ethyl group.

In one embodiment of the present specification, the Y1 and Y2; And Y2 and Y3 may combine to form a substituted or unsubstituted ring.

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

In one embodiment of the present specification, the Y1 and Y2; And Y2 and Y3 combine to form -SO ₃ M; Or it may form a substituted or unsubstituted benzene ring with -SO ₂ NHY, wherein M and Y are as defined in the formula (1).

In one embodiment of the present specification, the Y1 and Y2; And Y2 and Y3 combine to form -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY, wherein M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure, wherein Y is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, the Y1 and Y2; And Y2 and Y3 combine to form -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY, wherein M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure, wherein Y is a substituted or unsubstituted n-hexyl group.

In one embodiment of the present specification, the Y1 and Y2; And Y2 and Y3 combine to form -SO ₃ M; Or a benzene ring unsubstituted or substituted with -SO ₂ NHY, wherein M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure, wherein Y is an n-hexyl group substituted with an ethyl group.

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

는 상기 화학식 1에 연결되는 부위를 나타내고, X3 내지 X5 및 Y4는 서로 같거나 상이하고 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; -OH; -SO₃H;; -SO₃M; -SO₂NHY; -COOH; 포스핀기; 음이온성기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이며, 상기 M 및 Y는 상기 화학식 1에서 정의한 바와 같고, x3는 0 내지 4의 정수, x4, x5 및 y4는 0 내지 6의 정수이다. In the substituent,

Represents a moiety linked to Formula 1, X3 to X5 and Y4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; -OH; -SO ₃ H ;; -SO ₃ M; -SO ₂ NHY; -COOH; Phosphine groups; Anionic group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, wherein M and Y are as defined in Formula 1, x3 is an integer of 0 to 4, x4, x5 and y4 is an integer of 0 to 6.

는 상기 화학식 1에 연결되는 부위를 나타내고, X3 내지 X5 및 Y4는 서로 같거나 상이하고 각각 독립적으로 수소; -SO₃M; 또는 -SO₂NHY이며, 상기 M 및 Y는 상기 화학식 1에서 정의한 바와 같고, x3는 0 내지 4의 정수, x4, x5 및 y4는 0 내지 6의 정수이다. In the substituent,

Represents a moiety linked to Formula 1, X3 to X5 and Y4 are the same as or different from each other, and each independently hydrogen; -SO ₃ M; Or -SO ₂ NHY, wherein M and Y are as defined in Formula 1, x3 is an integer of 0 to 4, x4, x5 and y4 is an integer of 0 to 6.

In one embodiment of the present specification, R3 and R4 of Formula 1 are the same as or different from each other, each independently represent 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 Formula 1 are the same as or different from each other, each independently represent 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 Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R3 and R4 of Formula 1 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R3 and R4 of Formula 1 are the same as or different from each other, and each 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 Formula 1 are the same as or different from each other, and each independently a methyl group; Trifluoromethyl group (-CF ₃ ); Or a phenyl group.

In one embodiment of the present specification, R5 to R12 of Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Hydroxyl group; -COR; -COOR; Imide group; Amide group; Anionic group; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms; Substituted or unsubstituted sulfonate group; A substituted or unsubstituted amine group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms,

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 Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; -OH; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; -COOH; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group, wherein M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound comprising an ammonium structure, wherein M1, M2 and Y are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group.

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

In one embodiment of the present specification, R5 to R12 of Formula 1 are the same as or different from each other, and 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 Formula 1 are the same as or different from each other, and 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 Formula 1 are the same as or different from each other, and 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 Formula 1 are the same as or different from each other, and each independently hydrogen; -SO ₂ NHY; Or a substituted or unsubstituted methyl group, and Y is a hexyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R5 to R12 of Formula 1 are the same as or different from each other, and each independently hydrogen; -SO ₂ NHY; Or a methyl group unsubstituted or substituted with a halogen group, and Y is a hexyl group unsubstituted or substituted with an ethyl group.

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

In one embodiment of the present specification, R5 of Chemical Formula 1 is hydrogen; Or a trifluoromethyl group.

In one embodiment of the present specification, R6 of Chemical Formula 1 is hydrogen; -SO ₂ NHY; Or a trifluoromethyl group, and Y is a hexyl group substituted with an ethyl group.

In one embodiment of the present specification, R7 of Formula 1 is hydrogen.

In one embodiment of the present specification, R8 of Formula 1 is hydrogen.

In one embodiment of the present specification, R9 of Formula 1 is hydrogen.

In one embodiment of the present specification, R10 of Formula 1 is hydrogen.

In one embodiment of the present specification, R11 of Formula 1 is hydrogen.

In one embodiment of the present specification, R12 of Formula 1 is hydrogen.

In addition, in an exemplary embodiment of the present specification, R13 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; -OH; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; -COOH; Anionic group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, wherein M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound comprising an ammonium structure, wherein M1, M2 and Y are the same as or different from each other, each independently represent a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group, at least one of the R13 to R17 is an anionic group.

In one embodiment of the present specification, R13 to R17 are the same as or different from each other, and each independently hydrogen; -SO ₃ ^-; -SO ₃ M; Or —SO ₂ NHY, wherein M and Y are as defined above and at least one of R 13 to R 17 is an anionic group.

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

In one embodiment of this disclosure, R13 is -SO ₃ ^- a.

In one embodiment of the present specification, R14 is hydrogen.

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

In one embodiment of the present specification, 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 an anion of a compound containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus; Trifluoromethanesulfonic acid anion; Bis (trifluoromethylsulfonyl) amide anion; Bistrifluoromethanesulfonimide anion; Bisperfluoroethylsulfonimide anion; Tetraphenylborate anion; Tetrakis (4-fluorophenyl) borate; Tetrakis (pentafluorophenyl) borate; Tristrifluoromethanesulfonylmethide; And it is a compound selected from the group consisting of halogen groups.

In one embodiment of the present specification, X may be SO ₃ ⁻ .

In addition, in an exemplary embodiment of the present specification, r5 and r6 are integers of 0 to 4, when r5 is 2 or more, R5 is the same as or different from each other, and when r6 is 2 or more, R6 is the same as or different from each other.

In one embodiment of the present specification, r5 and r6 are integers of 0 to 3, when r5 is 2 or more, R5 is the same as or different from each other, and when r6 is 2 or more, R6 is the same or different from each other.

In one embodiment of the present specification, r5 and r6 are integers of 0 to 2, when r5 is 2, R5 is the same as 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 specification, r5 and r6 are 0 or 1.

In one embodiment of the present specification, r5 and r6 are zero.

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

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

In the above structures, L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1.

The description of the isomers can be applied to all of the xanthene dye structures described herein.

In one embodiment of the present specification, -SO ₃ M may mean that -SO ₃ ^- and M is an ionic bond or a salt bond.

In one embodiment of the present specification, M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And a compound including an ammonium structure, and the compound including the ammonium structure may include a unit represented by the following Formula A or represented by the following Formula B.

[Formula A]

[Formula B]

In Chemical Formula A,

Ra to Rd are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; -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 group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group,

L ₁ and L ₂ is a substituted or unsubstituted alkylene group,

In Chemical Formula B,

Rb to Rd are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring,

Z is a substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; -L ₃ -NHCO-; Or -L ₄ -OCO-,

L ₃ and L ₄ is a substituted or unsubstituted alkylene group,

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

According to an exemplary embodiment of the present specification, in the general formula A, Ra to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; -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, wherein R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, wherein L ₁ and L ₂ is a substituted or unsubstituted alkylene group,

In Formula B, Rb to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, 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-, wherein L ₃ and L ₄ is a substituted or unsubstituted alkylene group, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, and Re to Rg are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula A, Ra to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms; -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, wherein R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms, wherein L ₁ and L ₂ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms,

In Formula B, Rb to Rd are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, Z is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; Substituted or unsubstituted arylene group having 6 to 20 carbon atoms; -L ₃ -NHCO-; Or -L ₄ -OCO-, wherein L ₃ and L ₄ is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, and Re to Rg are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, the unit means a repeating structure in which the monomer is included in the polymer, and the unit may be included in the main chain in the polymer to constitute the polymer.

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

When the compound including the unit represented by the formula (B) is a polymer, the compound represented by the formula (B) may include within 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 Formula (B) may be 1000 to 10,000, preferably 3,000 to 8,000, more preferably 5,000 to 7,000.

According to an exemplary embodiment of the present specification, the terminal of the compound containing a unit represented by the formula (B) is hydrogen; Halogen group; Or a substituted or unsubstituted alkyl group.

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

[Formula 2]

In Chemical Formula 2,

L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1.

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

[Formula 3]

In Chemical Formula 3,

L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1.

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

[Formula 4]

In Chemical Formula 4,

L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1.

In one embodiment of the present specification, the dianhydride group including the nitrogen atom of Formula 1 may be a compound represented by any one of the following substituents.

는 상기 화학식 1에 연결되는 부위를 나타내고, In the substituent,

Represents a site linked to the formula (1),

X1, X2, Y1 to Y3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; -OH; -SO ₃ H ;; -COOH; Phosphine groups; Anionic group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups may be bonded to form a substituted or unsubstituted ring.

In one embodiment of the present specification, the compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas.

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

In one embodiment of the present specification, the substituent in the ring of the formula is not specified means that the substituent may be substituted for any portion of the carbon included in the ring.

에 있어서,

는 -CF₃로 치환된 벤젠 고리에 있어서, -SCH₃로 치환된 탄소를 제외한 나머지 탄소 중 어느 하나에 치환될 수 있다는 것을 의미하며, 구체적으로 하기 4개의 구조로 표시될 수 있다.for example,

To

Means that in the benzene ring substituted with -CF ₃ , it may be substituted with any one of carbons other than the carbon substituted with -SCH ₃ , and may be represented by the following four structures.

에 있어서,

는 -SO₂NHY로 치환된 나프탈렌 고리에 있어서, 나프탈렌에 포함되는 탄소 중 어느 하나에 치환될 수 있다는 것을 의미하며, 구체적으로 하기 6개의 구조로 표시될 수 있다.As another example,

To

In the naphthalene ring substituted with -SO ₂ NHY, it means that can be substituted with any one of the carbon included in the naphthalene, it can be represented by the following six structures.

In the above six structures, Y is as defined above.

In addition, according to an exemplary embodiment of the present specification, it is possible to provide a color material composition comprising the compound.

The color material composition may further include at least one of dyes and pigments in addition to the compound of Formula 1. For example, the colorant composition may include only the compound of Formula 1, but may include the compound of Formula 1 and one or more dyes, or may include the compound of Formula 1 and one or more pigments, or the compound of Formula 1 And at least one dye and at least one pigment.

According to an exemplary embodiment of the present specification, it is possible to provide a photosensitive resin composition comprising the color material composition.

According to an exemplary embodiment of the present specification, the photosensitive resin composition is a compound represented by Formula 1; Binder resins; Polyfunctional monomers; Photoinitiators; And a solvent may be further included.

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

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

Polyfunctional monomers to impart the mechanical strength of the membrane include unsaturated carboxylic acid esters; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl ( Meta) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetra Hydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl ( Meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxy CD-ethyleneglycol (Meth) acrylate, methoxy triethylene glycol (meth) acrylate, methoxy tripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate , p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1 , 1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate , Methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate and butyl α-hydroxymethyl acrylate It is, but is not limited thereto.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o, m, p) -vinyl toluene, (o, m, p) -methoxy styrene, and (o, m, p) -chloro styrene. It may be selected from the group consisting of, but is not limited to these.

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

Specific examples of the unsaturated imides are selected from the group consisting of N-phenyl maleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexyl maleimide It may be, but is not limited to these.

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

The monomer which imparts the alkali solubility is not particularly limited as long as it contains an acid group. For example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene-2-carboxylic acid, mono 2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxy polycaprolactone mono (meth) acrylate selected from the group consisting of Although it is preferable to use 1 or more types, it is not limited to these.

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

The polyfunctional monomer is a monomer that forms a photoresist image by light, specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethyleneglycol methacrylate, bisphenoxy ethylalcohol diacrylate, trishydroxyethylisocyanurate trimethacrylate, trimethyl 1 selected from the group consisting of propane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate Species or a mixture of two or more thereof.

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

The acetophenone-based compound is 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl-2-morpholino-1-propan-1-one, 2-benzyl-2-dimethylamino -1- (4-morpholinophenyl) -butan-1-one, 2- (4-bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, and the like.

As the biimidazole-based compound, 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4 , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4, 4 ', 5,5'-tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole, It is not limited to this.

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

The oxime-based compound is 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Shibagai Co., Shijiai 124), ethanone, -1- (9 -Ethyl) -6- (2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGII242), N-1919 (Adeca Co.), and the like.

The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 , 1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2 Ethoxy propanol, 2-methoxy propanol, 3-methoxy butanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl ah Cetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, but may be It is not limited only.

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

According to an exemplary embodiment of the present specification, based on the total weight of solids in the photosensitive resin composition, the content of the compound represented by Formula 1 is 5% by weight to 60% by weight, the content of the binder resin is 1% by weight To 60% by weight, the content of the photoinitiator is 0.1% to 20% by weight, and the content of the multifunctional monomer is 0.1% to 50% by weight.

Specifically, the photosensitive resin composition is based on the total weight of solids in the photosensitive resin composition, the content of the compound represented by Formula 1 is 5% by weight to 50% by weight, the content of the binder resin is 1% by weight to 50 Wt%, the content of the photoinitiator is 0.1% to 10% by weight, and the content of the multifunctional monomer is 0.1% to 45% by weight.

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

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

In one embodiment of the present specification, based on the total weight of the photosensitive resin composition, the additive may further comprise 0.1% by weight to 20% by weight.

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

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

According to one embodiment of the present specification, the photosensitive resin composition is 1 or 2 selected from the group consisting of photocrosslinking sensitizers, curing accelerators, antioxidants, adhesion promoters, surfactants, thermal polymerization inhibitors, ultraviolet absorbers, dispersants, and leveling agents. The above additive is further included.

The photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoyl Benzophenone compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorenone compounds such as 9-florenone, 2-chloro-9-prorenone, and 2-methyl-9-florenone; Thioxanthones such as thioxanthone, 2,4-diethyl thioxanthone, 2-chloro thioxanthone, 1-chloro-4-propyloxy thioxanthone, isopropyl thioxanthone and diisopropyl thioxanthone compound; Xanthone compounds such as xanthone and 2-methylxanthone; Anthraquinone compounds such as anthraquinone, 2-methyl anthraquinone, 2-ethyl anthraquinone, t-butyl anthraquinone and 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane Acridine-based compounds; Dicarbonyl compounds such as benzyl, 1,7,7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione, 9,10-phenanthrenequinone; Phosphine oxide compounds such as 2,4,6-trimethylbenzoyl diphenylphosphine oxide and bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentyl phosphine oxide; Benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate and 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4- Amino synergists such as methyl-cyclopentanone; 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3 -Benzoyl-7-methoxy-coumarin, 10,10-carbonylbis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzo Coumarin-based compounds such as pyrano [6,7,8-ij] -quinolizine-11-one; Chalcone compounds such as 4-diethylamino chalcone and 4-azidebenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; one or more selected from the group consisting of can be used.

The curing accelerator is used to increase the curing and mechanical strength, specifically 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), penta Erythritol-tetrakis (2-mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropio Nate) can be used one or more selected from the group consisting of.

As the adhesion promoter used in the present specification, methacryloyloxy propyltrimethoxy silane, methacryloyloxy propyldimethoxy silane, methacryloyloxy propyltriethoxy silane, methacryloyloxy propyldimethoxysilane One or more types of methacryloyl silane coupling agents, such as these, can be selected and used, and at least 1 type can be selected from octyl trimethoxy silane, dodecyl trimethoxy silane, and octadecyl trimethoxy silane as an alkyl trimethoxy silane. You can choose to use it.

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

The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, thio antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include phosphoric acid thermal stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di-t-butyl-4-hydroxy Benzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl-6-t-butylphenol) or bis [3 , 3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p-phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine System secondary antioxidants; Thio such as dilauryl disulfide, dilaurylthiopropionate, distearylthiopropionate, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane System secondary antioxidants; Or triphenyl phosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-ditbutylphenyl) Pentaerythritol Diphosphite or (1, 1'-biphenyl) -4,4'-diylbisphosphonoic acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4 ' Phosphite-based secondary antioxidants such as -diylbisphosphonous acid tetrakis [2,4-bis (1,1-dimethylethyl) phenyl] ester).

As the ultraviolet absorbent, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxy benzophenone, etc. may be used, but is not limited thereto. All commonly used ones can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt and N-nitrosophenylhydroxy Amine aluminum salt, p-methoxyphenol, di-t-butyl-p-cresol, pyroggarol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2- It may include one or more selected from the group consisting of methylenebis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole and phenothiazine, but is not limited thereto. It may include those generally known in the art.

The dispersant may be used as a method of internally adding to the pigment in the form of surface treatment of the pigment in advance or externally adding to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant may be used, and examples thereof include fluorine, ester, cationic, anionic, nonionic and amphoteric surfactants. These can be used individually or in combination of 2 or more types.

Specifically, the dispersant may be polyalkylene glycol and esters thereof, polyoxyalkylene polyhydric alcohols, ester alkylene oxide adducts, alcohol alkylene oxide adducts, sulfonic acid esters, sulfonate salts, carboxylic acid esters, carboxylate salts, At least one selected from the group consisting of alkylamide alkylene oxide adducts and alkylamines is not limited thereto.

The leveling agent may be polymeric or nonpolymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamine, reaction products of amines and epoxides, and specific examples of nonpolymeric leveling agents include non-polymeric sulfur-containing and non-polymeric nitrogen-containing. Including but not limited to the compounds, all generally used in the art can be used.

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

In more detail, the photosensitive resin composition of this specification is apply | coated and hardened | cured by a suitable method on a base material, and forms the photosensitive material of a thin film or a pattern form.

Although it does not restrict | limit especially as said coating method, A spray method, a roll coating method, a spin coating method, etc. can be used, Generally, a spin coating method is used widely. In addition, after forming a coating film, some residual solvent can be removed in some cases under reduced pressure.

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

The photosensitive resin composition according to the present disclosure is a pigment-dispersed photosensitive material for manufacturing a thin film transistor liquid crystal display device (TFT LCD) color filter, a thin film transistor liquid crystal display device (TFT LCD) or a photosensitive material for forming a black matrix of an organic light emitting diode. Photoresist for forming overcoat layer, column spacer photoresist, photocurable paint, photocurable ink, photocurable adhesive, printing plate, photoresist for printed circuit board, photoresist for plasma display panel (PDP), etc. There is no restriction in particular.

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

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

The photosensitive resin composition according to the exemplary embodiment of the present specification is excellent in heat resistance, so that there is little change in color by heat treatment, thereby providing a color filter having high color reproducibility and high luminance and contrast ratio even during the curing process during the manufacture of the color filter. Can be.

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

Specifically, the photosensitive resin composition according to one embodiment of the present specification may be spincoated on glass (5 × 5 cm ² ), and prebake at 100 ° C. for 100 seconds to form a film. . The distance between the substrate on which the film is formed and the photo mask is set to 250 um, and 40 mJ / cm ² exposure dose is irradiated to the entire surface of the substrate using an exposure machine. Thereafter, the exposed substrate may be developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and postbake at 230 ° C. for 20 minutes to prepare a substrate.

The heat resistance evaluation can be measured by the method described below. Using a spectrometer, the substrate manufactured according to the exemplary embodiment of the present invention obtains a transmittance spectrum of a visible light region in the range of 380 nm to 780 nm. In addition, the prebake substrate is further postbake at 230 ° C. for 20 minutes to obtain transmittance spectra in the same equipment and measurement range.

The spectrometer may be that of MCPD-Otsuka, but is not limited thereto.

Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter, ΔEab) is calculated using the obtained values E (L *, a *, b *). A small ΔEab value indicates excellent color heat resistance. When ΔEab <3, it can be used as a color filter dye, and it can be said that it is a color material having excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.

[Calculation 1]

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

The contrast ratio can be measured by the method described below. The substrate produced according to the substrate manufacturing method was measured using a contrast ratio measuring device, and the luminance produced when two polarizing plates were orthogonal and the luminance when two polarizing plates were orthogonal to each other. To calculate the contrast ratio by the following formula (2).

[Calculation 2]

Contrast ratio = luminance when two polarizing plates are horizontal / luminance when two polarizing plates are vertical

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

Fluorescence intensity of the color filter according to an exemplary embodiment of the present specification is the substrate using the Sinco FS-2 fluorescence measuring apparatus at room temperature (25 ℃), the excitation wavelength of 545nm, emission wavelength of 560nm to 720nm It can be measured.

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

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

A black pattern on a lattice called a black matrix can be disposed between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material of the black matrix. In this case, a method of depositing chromium over the entire glass substrate and forming a pattern by etching may be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution caused by chromium waste liquid, a resin black matrix by a pigment dispersion method capable of fine processing can be used.

The black matrix may use a black pigment or a black dye as a colorant. For example, carbon black may be used alone, or carbon black and coloring pigments may be used. At this time, since coloring pigments lacking light shielding properties may be mixed, even if the amount of colorant is increased, the strength of the film or the adhesion to the substrate may be reduced. There is no advantage.

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

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

Hereinafter, the present invention will be described in detail with reference to Examples. However, the embodiments according to the present disclosure may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

<Example>

Synthesis Example of Compound

Synthesis Example 1 Synthesis of Compound 1

Synthesis of Intermediate 1

A-1 5g (12.34mmol), B-1 10.31g (74.03mmol) and N-methyl-2-pyrrolidone (NMP, N-Methyl-) in 250ml 2-neck Round Bottom Flask (RBF) 2-pyrrolidone) 80g was added and stirred. The mixture was heated to 150 ° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, and then poured into 800 ml of 1M hydrochloric acid (HCl) and stirred for 30 minutes.

The precipitate thus obtained was filtered and washed with water under reduced pressure, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 7 g (11.46 mmol) of an intermediate 1.

Ionization mode APCI +: m / z = 611 {M + H], Exact Mass: 610

Synthesis of Compound 1

In a 100 ml 2-neck Round Bottom Flask (RBF), 1.5 g (2.46 mmol) of intermediate 1, 2.958 g (9.82 mmol) of C-1 and 1.358 g (9.82 mmol) of potassium carbonate (K ₂ CO ₃ ) were added to N. -30 g of methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was stirred. After heating to 100 ° C. and stirring for 6 hours, the reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes. The precipitate was filtered and washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 1.3 g (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

A-1 5g (12.34mmol), B-2 14.90g (74.03mmol) and N-methyl-2-pyrrolidone (NMP, N-Methyl-) in 250ml 2-neck Round Bottom Flask (RBF) 2-pyrrolidone) 80g was added and stirred. The mixture was heated to 150 ° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, and then poured into 800 ml of 1M hydrochloric acid (HCl) and stirred for 30 minutes.

The precipitate was then filtered and washed with water under reduced pressure and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 7.2 g (9.80 mmol) of intermediate 2.

Ionization mode APCI +: m / z = 735 {M + H], Exact Mass: 734

Synthesis of Compound 2

1.100g (2.46mmol) of intermediate 2, 2.958g (9.82mmol) of C-1, 1.358g (9.82mmol) of potassium carbonate (K ₂ CO ₃ ) were added to a 100ml 2-neck Round Bottom Flask (RBF). 30 g of methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was added thereto and stirred. The mixture was heated to 100 ° C. and stirred for 6 hours. The reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate thus obtained was filtered and washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain compound 2, 1 g (0.925 mmol).

Ionization mode APCI +: m / z = 1081 [M + H], Exact Mass: 1081

Synthesis Example 3 Synthesis of Compound 3

Synthesis of Intermediate 3

A-1 5g (12.34mmol), B-3 1 10.31g (74.03mmol) and N-methyl-2-pyrrolidone (NMP, N-Methyl) in 250ml 2-neck Round Bottom Flask (RBF) -2-pyrrolidone) 80g was added and stirred. The mixture was heated to 150 ° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, and then poured into 800 ml of 1M hydrochloric acid (HCl) and stirred for 30 minutes.

Thereafter, the precipitate was filtered and washed with water under reduced pressure, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 6.8 g (11.130 mmol) of an intermediate 3.

Ionization mode APCI +: m / z = 611 {M + H], Exact Mass: 610

Synthesis of Compound 3

100 ml 2-neck Round Bottom Flask (RBF), Intermediate 3 1.502g (2.46mmol), C-1 2.958g (9.82mmol), Potassium Carbonate (K ₂ CO ₃ ) 1.358 g (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. After heating to 100 ° C. and stirring for 6 hours, the reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was then filtered and washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 1.4 g (1.463 mmol) of compound 3.

Ionization Mode APCI +: m / z = 957 [M + H], Exact Mass: 956

Synthesis Example 4 Synthesis of Compound 4

Synthesis of Intermediate 4

A-1 5g (12.34mmol), B-4 1 10.31g (74.03mmol) and N-methyl-2-pyrrolidone (NMP, N-Methyl) in 250ml 2-neck Round Bottom Flask (RBF) -2-pyrrolidone) 80g was added and stirred. The mixture was heated to 150 ° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, and then poured into 800 ml of 1M hydrochloric acid (HCl) and stirred for 30 minutes.

Thereafter, the precipitate was filtered and washed with water under reduced pressure, dried in a vacuum oven at 60 ° C. for 12 hours to obtain 6.5 g (10.64 mmol) of an intermediate 4.

Ionization mode APCI +: m / z = 611 {M + H], Exact Mass: 610

Synthesis of Compound 4

In a 100 ml 2-neck Round Bottom Flask (RBF), Intermediate 4 1.502 g (2.46 mmol), C-1 2.958 g (9.82 mmol) and potassium carbonate (K ₂ CO ₃ ) 1.358 g (9.82 mmol) were added to N. 30 g of methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was added thereto and stirred. After heating to 100 ° C. and stirring for 6 hours, the reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered, washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 1.7 g (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

A-1 5g (12.34mmol), B-5 14.30g (74.03mmol) and N-methyl-2-pyrrolidone (NMP, N-Methyl-) in 250ml 2-neck Round Bottom Flask (RBF) 2-pyrrolidone) 80g was added and stirred. The mixture was heated to 150 ° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, and then poured into 800 ml of 1M hydrochloric acid (HCl) and stirred for 30 minutes.

Thereafter, the precipitate was filtered and washed with water under reduced pressure, dried in a vacuum oven at 60 ° C. for 12 hours to obtain 7.2 g (10.02 mmol) of an intermediate 5.

Ionization mode APCI +: m / z = 719 {M + H], Exact Mass: 718

Synthesis of Compound 5

In a 100 ml 2-neck Round Bottom Flask (RBF), intermediate 5 1.768 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1.358 g (9.82 mmol) N 30 g of methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was added thereto and stirred. After heating to 100 ° C. and stirring for 6 hours, the reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

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

Ionization mode APCI +: m / z = 1065 [M + H], Exact Mass: 1064

Synthesis Example 6 Synthesis of Compound 6

Synthesis of Intermediate 6

A-1 5g (12.34mmol), B-6 15.33g (74.03mmol) and N-methyl-2-pyrrolidone (NMP, N-Methyl-) in 250ml 2-neck Round Bottom Flask (RBF) 2-pyrrolidone) 80g was added and stirred. The mixture was heated to 150 ° C. and stirred for 4 hours. The reaction solution was cooled to room temperature, and then poured into 800 ml of 1M hydrochloric acid (HCl) and stirred for 30 minutes.

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

Ionization mode APCI +: m / z = 747 {M + H], Exact Mass: 746

Synthesis of Compound 6

100 ml 2-neck Round Bottom Flask (RBF), Intermediate 6 1.837g (2.46mmol), C-1 2.958g (9.82mmol), Potassium Carbonate (K ₂ CO ₃ ) 1.358g (9.82mmol) N -30 g of methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was added and stirred. The mixture was heated to 100 ° C. and stirred for 6 hours. The reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered, washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 2.5 g (2.287 mmol) of compound 6.

Ionization mode APCI +: m / z = 1093 [M + H], Exact Mass: 1092

Synthesis Example 7 Synthesis of Compound 7

In the preparation of Compound 1, C-1 was changed to C-2, and otherwise, Compound 7 was obtained by the same method.

Ionization Mode APCI +: m / z = 985 [M + H], Exact Mass: 984

Synthesis Example 8 Synthesis of Compound 8

In the preparation of Compound 2, C-1 was changed to C-2, and Compound 8 was obtained through the same method except for the above.

Ionization mode APCI +: m / z = 1109 [M + H], Exact Mass: 1108

Synthesis Example 9 Synthesis of Compound 9

In the preparation of Compound 3, C-1 was changed to C-2, and Compound 9 was obtained through the same method except for the above.

Ionization Mode APCI +: m / z = 985 [M + H], Exact Mass: 984

Synthesis Example 10 Synthesis of Compound 10

In the preparation of Compound 4, C-1 was changed to C-2, and Compound 10 was obtained by the same method except for the above.

Ionization Mode APCI +: m / z = 985 [M + H], Exact Mass: 984

Synthesis Example 11 Synthesis of Compound 11

In the preparation of Compound 5, C-1 was changed to C-2, and Compound 11 was obtained through the same method except for the above.

Ionization mode APCI +: m / z = 1093 [M + H], Exact Mass: 1092

Synthesis Example 12 Synthesis of Compound 12

In the preparation of Compound 6, C-1 was changed to C-2, and Compound 12 was obtained through the same method except for the above.

Ionization mode APCI +: m / z = 1121 [M + H], Exact Mass: 1120

Synthesis Examples 13 to 18 Synthesis of Compounds 13 to 18

In the preparation of compounds 1 to 6, C-1 was changed to C-3, and compounds 13 to 18 were obtained through the same method except for the following.

Compound 13: Ionization Mode APCI +: m / z = 1085 [M + H], Exact Mass: 1084

Compound 14: Ionization Mode APCI +: m / z = 1209 [M + H], Exact Mass: 1208

Compound 15: Ionization Mode APCI +: m / z = 1085 [M + H], Exact Mass: 1084

Compound 16: Ionization Mode APCI +: m / z = 11085 [M + H], Exact Mass: 1084

Compound 17: Ionization Mode APCI +: m / z = 1193 [M + H], Exact Mass: 1192

Compound 18: Ionization Mode APCI +: m / z = 1221 [M + H], Exact Mass: 1220

Comparative Compound 1.

S1 1.414 g (2.46 mmol), bromopropane 1.21 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1.358 g (9.82 mmol) in a 100 ml 2-neck Round Bottom Flask (NB) 30 g of 2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was added thereto and stirred. After heating to 100 ° C. and stirring for 6 hours, the reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered, washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain Comparative Compound 1.

Ionization mode APCI +: m / z = 659 [M + H], Exact Mass: 658

Comparative Compound 2

S2 1.4234g (2.46mmol), C-2 3.094g (9.82mmol), potassium carbonate (K ₂ CO ₃ ) 1.358g (9.82mmol) in 100ml 2-neck Round Bottom Flask 30 g of methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) was added thereto and stirred. After heating to 100 ° C. and stirring for 6 hours, the reaction solution was cooled to room temperature, and then poured into 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered, washed with water under reduced pressure, separated through column chromatography, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain Comparative Compound 2.

Ionization Mode APCI +: m / z = 953 [M + H], Exact Mass: 952

Comparative Compound 3

In the same manner as in the synthesis of Intermediate 1 in Synthesis Example 1, Comparative Compound 3 was synthesized using S3 and S4 instead of A-1 and B-1.

Comparative Compound 4

3 g (4.553 mmol) of Comparative Compound 1 was dissolved in 50 g of 10% 98% sulfuric acid. Thereafter, 0.807 g (4.553 mmol) of N-hydroxymethylphthalimide was added thereto, and the temperature was raised to 45 ° C. and stirred for 2 hours. The reaction solution was added to 500 g of water to precipitate crystals, and the precipitate was filtered under reduced pressure to obtain Comparative Compound 4.

Example 1

5.554 g of compound 1, a copolymer of benzyl methacrylate and methacrylic acid with a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, gel permeation chromatography (GPC) measured by weight average molecular weight 20,000 g / mol, molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent polypropylene glycol monomethyl ether acetate (PGMEA) 10.376 g, photoinitiator as I-369 (BASF) 2.018 g, polyfunctional monomer Photosensitive resin composition 1 was prepared by mixing 12.443 g of DPHA, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of DIC F-475 with an additive surfactant.

Examples 2-18

In Example 1, the compound 1 was changed into the compound 2-18, and the photosensitive resin composition 2-18 was respectively manufactured by the same composition except that.

Comparative Example 1

5.554 g of Comparative Compound 1, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average molecular weight 20,000 g measured by gel permeation chromatography (GPC)) / mol, molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent polypropylene glycol monomethyl ether acetate (PGMEA) 10.376 g, photoinitiator as I-369 (BASF) 2.018 g, polyfunctional monomer The photosensitive resin composition of Comparative Example 1 was prepared by mixing 12.443 g of DPHA, 68.593 g of solvent PGMEA (polypropylene glycol monomethyl ether acetate), and 1.016 g of DIC F-475 as an additive surfactant. .

Comparative Examples 2 to 4

In Comparative Example 1, Comparative Compound 1 was changed to Comparative Compounds 2 to 4, except that the photosensitive resin compositions of Comparative Examples 2 to 4 were prepared with the same composition.

Experimental Example

PCB Fabrication

The photosensitive resin composition concerning Examples 1-18 and Comparative Examples 1-4 was used for the board | substrate preparation, respectively. Specifically, the photosensitive resin composition according to Examples 1 to 18 and Comparative Examples 1 to 4 was spin coated on glass (5 × 5 cm ² ), and prebake at 100 ° C. for 100 seconds. To form a film.

The distance between the substrate on which the film was formed and the photo mask was set to 250 um, and the exposure amount of 40 mJ / cm ² was irradiated on the entire surface of the substrate using an exposure machine. Thereafter, the exposed substrate was developed in a developer (potassium hydroxide (KOH), 0.05%) for 60 seconds, and postbake at 230 ° C. for 20 minutes to prepare a substrate.

Heat resistance rating

The substrate produced according to the substrate manufacturing method was obtained using a spectrometer (MCPD-Otsuka Co., Ltd.) to obtain a transmittance spectrum of the visible light range of 380nm to 780nm. In addition, the prebake substrate was further postbake at 230 ° C. for 20 minutes to obtain transmittance spectra in the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter, ΔEab) was calculated 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, it can be used as a color filter dye, and it can be said that it is a color material having excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.

[Calculation 1]

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

ΔEab (Post Heat Treatment-Heat 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, the color pattern substrate formed by using the photosensitive resin compositions of Examples 1 to 18 of the present invention, the difference between the transmittance spectrum (ΔEab) after the post-heat treatment and post-heat treatment is less than 3, the color stability It was confirmed that the heat resistance was very high because it is very small.

Contrast Ratio Measurement

The substrate produced according to the substrate manufacturing method was put in between the two polarizing plates using a contrast ratio measuring instrument (CT-1, ZOENTECH Co., Ltd.) and the brightness when two polarizing plates are horizontal and two polarizing plates The brightness | luminance in this orthogonality was measured, and the contrast ratio was computed by following formula (2).

[Calculation 2]

Contrast ratio = luminance when two polarizing plates are horizontal / luminance when two polarizing plates are vertical

Contrast ratio calculated by the above formula 2 was calculated by the following formula 3 contrast ratio improvement, it is shown in Table 2 below.

[Calculation 3]

Contrast ratio improvement rate = (Example contrast ratio-Comparative example 1, 2 or 4 contrast ratio) / Comparative example 1, 2 or 4 contrast ratio * 100)

Contrast ratio improvement rate (%) Based on Comparative Example 1 Based on Comparative Example 2 Comparative Example 4 Standard Example 1 511.75 316.8 510.21 Example 2 494.10 305.87 471.21 Example 3 319.60 197.85 300.46 Example 4 332.66 205.93 314.57 Example 5 352.59 218.27 331.67 Example 6 532.38 329.57 510.43 Example 7 384.80 238.21 329.81 Example 8 355.13 219.84 329.47 Example 9 282.61 174.95 244.93 Example 10 303.05 187.6 286.42 Example 11 335.79 207.87 308.78 Example 12 401.65 248.64 377.56 Example 13 324.43 200.84 209.47 Example 14 300.17 185.82 254.38 Example 15 220.47 136.48 197.83 Example 16 230.29 142.56 201.49 Example 17 256.39 158.72 223.83 Example 18 335.48 207.68 319.52

Referring to Table 2, compared with Comparative Example 1, it was confirmed that the contrast ratio of Examples 1 to 18 was improved 220.47% to 532.38%. In addition, it was confirmed that the contrast ratio of Examples 1 to 18 was improved by 136.48% to 329.57% compared to Comparative Example 2. In addition, it was confirmed that the contrast ratio of Examples 1 to 18 was improved from 197.83% to 510.43% compared to Comparative Example 4.

Fluorescence intensity measurement

The substrate prepared according to the substrate fabrication method was measured at room temperature (25 ° C.) using a Sinco FS-2 fluorescence measuring instrument, and the fluorescence intensity was measured at an excitation wavelength of 545 nm and an emission wavelength of 560 nm to 720 nm. It was.

According to Figure 1, the fluorescence intensity of Examples 6, 7 and 12 according to one embodiment of the present specification was lower than Comparative Examples 1 and 2, it was confirmed that excellent contrast ratio can be obtained without adding additional dye.

Permeability Evaluation

Using a spectrometer (MCPD-Otsuka Co., Ltd.), the substrate prepared according to the above substrate manufacturing method was used to obtain a transmittance spectrum of visible region in the range of 380 nm to 780 nm for a substrate post-baked at 230 ° C. for 20 minutes.

In particular, the blue color filter may exhibit better luminance when the maximum transmittance is high at 380 nm to 480 nm at luminous x, luminous y, and luminous z.

Fig. 2 shows the luminous sense x, luminous sensitivity and luminous sensitivity z.

Permeability%
(% Maximum transmittance from 380nm to 480nm) Example 1 95.756 Example 7 92.906 Example 13 95.721 Comparative Example 3 88.528

Referring to Table 3, it can be seen that the maximum transmittance at 380nm ~ 480nm of Examples 1 and 7, 13 compared with the Comparative Example 3.

According to FIG. 3, it was confirmed that the transmittance at 380 nm to 480 nm of Examples 1, 7 and 13 according to one embodiment of the present specification was greater than that of Comparative Example 3, thereby indicating better luminance in the blue color filter.

Claims (14)

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

In Chemical Formula 1,
L1 and L2 are the same as or different from each other, and each independently a substituted or unsubstituted alkylene group,
R1 and R2 are the same or different from each other, and each independently a dianhydride group containing a nitrogen atom,
R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
R5 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; -OH; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; -COOH; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted cycloalkenyl group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
R13 to R17 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; -OH; -SO ₃ ^-; -SO ₃ H; -SO ₃ M; -SO ₂ NM1M2; -SO ₂ NHY; -COOH; Anionic group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure,
M1, M2 and Y are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; And it is selected from the group consisting of a substituted or unsubstituted heteroaryl group,
At least one of the R13 to R17 is an anionic group,
X is an anionic group,
a is 0 or 1,
r5 and r6 are integers of 0 to 4, and when R5 is 2 or more, R5 is the same or different from each other. When r6 is 2 or more, R6 is the same or different from each other. The method of claim 1, wherein X is an anion of a compound containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon and phosphorus; Trifluoromethanesulfonic acid anion; Bis (trifluoromethylsulfonyl) amide anion; Bistrifluoromethanesulfonimide anion; Bisperfluoroethylsulfonimide anion; Tetraphenylborate anion; Tetrakis (4-fluorophenyl) borate; Tetrakis (pentafluorophenyl) borate; Tristrifluoromethanesulfonylmethide; And halogen groups. The method according to claim 1, wherein M is Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; And it is selected from the group consisting of a compound containing an ammonium structure,
The compound including the ammonium structure is a compound comprising a unit represented by the following formula (A) or a formula (B):
[Formula A]

[Formula B]

In Chemical Formula A,
Ra to Rd are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted arylalkyl group; -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 group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group,
L ₁ and L ₂ is a substituted or unsubstituted alkylene group,
In Chemical Formula B,
Rb to Rd are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group, or two of Rb to Rd combine with each other to form a substituted or unsubstituted ring,
Z is a substituted or unsubstituted alkylene group; Substituted or unsubstituted arylene group; -L ₃ -NHCO-; Or -L ₄ -OCO-,
L ₃ and L ₄ is a substituted or unsubstituted alkylene group,
Re to Rg are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted alkyl group. The compound of claim 1, wherein Formula 1 is represented by Formula 2:
[Formula 2]

In Chemical Formula 2,
L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1. The compound of claim 1, wherein Formula 1 is represented by Formula 3:
[Formula 3]

In Chemical Formula 3,
L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1. The compound of claim 1, wherein Formula 1 is represented by Formula 4:
[Formula 4]

In Chemical Formula 4,
L1, L2, R1 to R17, X, a, r5 and r6 are the same as defined in Chemical Formula 1. The compound of claim 1, wherein the dianhydride group containing the nitrogen atom is represented by any one of the following substituents:

In the substituent,

Represents a site linked to the formula (1),
X1, X2 and Y1 to Y3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; -OH; -SO ₃ H ;; -COOH; Phosphine groups; Anionic group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent groups combine to form a substituted or unsubstituted ring. The compound of claim 1, wherein the compound represented by Formula 1 is represented by one of the following formulas:

In the above formula,
M and Y are as defined in the formula (1). A compound of any one of claims 1-8; Binder resins; Polyfunctional monomers; Photoinitiators; And a photosensitive resin composition comprising a solvent. The method according to claim 9, wherein the content of the compound represented by Formula 1 based on the total weight of solids in the photosensitive resin composition is 5% by weight to 60% by weight,
The binder resin content is 1% by weight to 60% by weight,
The content of the photoinitiator is 0.1% by weight to 20% by weight,
The content of the multifunctional monomer is 0.1% by weight to 50% by weight of the photosensitive resin composition. The photosensitive resin composition of Claim 9 which further contains an additive. The photosensitive material manufactured using the resin composition of Claim 9. A color filter comprising the photosensitive material according to claim 12. Display device including a color filter according to claim 13.

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