JP6940231B2 - Xanthene compounds, photosensitive resin compositions containing them, photosensitive materials, color filters, and display devices. - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0039901 filed with the Korean Patent Office on April 5, 2018, the entire contents of which are incorporated herein by reference.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0135250 filed with the Korean Patent Office on November 6, 2018, the entire contents of which are incorporated herein by reference.

The present specification relates to xanthene compounds and photosensitive resin compositions containing them. The present specification also relates to a photosensitive material, a color filter, and a display device including the photosensitive material produced by using the photosensitive resin composition.

Recently, color filters are required to have high brightness and high brightness / dark ratio. Further, one of the main purposes of developing a display device is to differentiate the performance of display elements by improving the color purity and to improve the productivity in the manufacturing process.

Conventionally, the pigment type used as a color material of a color filter exists in a color photoresist in a particle-dispersed state, so that it is difficult to adjust the brightness and the light-dark ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, they aggregate in the color filter to reduce their solubility and dispersibility, and the large particles that are agglomerated cause multiple scattering of light. Such scattering of polarized light is considered to be the main cause of lowering the light-dark ratio. Efforts are being made to improve the brightness and contrast ratio by ultra-fine graining and stabilizing the dispersion of pigments, but the degree of freedom in selecting a color material for realizing color coordinates for a high color purity display device is limited. Further, the pigment dispersion method using a color material already developed, particularly a pigment, has reached a limit in improving the color purity, brightness and light-dark ratio of a color filter using the same.

As a result, there is a need for the development of new color materials that improve color purity, color reproduction, brightness, and light-dark ratio.

The present inventors intend to provide a xanthene-based compound having a novel structure, a photosensitive resin composition containing the same, a photosensitive material produced by using the xanthene compound, a color filter, and a display device containing the same.

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

[Chemical formula 1]

In the chemical formula 1,
L1 and L2 are the same or different from each other and are independently substituted or unsubstituted alkylene groups.
R1 and R2 are dianhydride groups containing nitrogen atoms, which are the same or different from each other and are independent of each other.
R3 and R4 are the same or different from each other and are independently substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups, respectively.
R5 to R12 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; -OH; -SO ₃ H; -SO ₃ M; -SO ₂ NM1 M2; -SO ₂ NHY; -COOH; substitution or From unsubstituted alkyl groups; substituted or unsubstituted cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted cycloalkenyl groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heteroaryl groups Selected from the group
R13~R17, equal to or different from each other, each independently, hydrogen, deuterium, ^{_{halogen; -OH; -SO 3 -; -SO}} 3 H; -SO 3 M; -SO 2 NM1M2; -SO 2 NHY; -COOH; anionic group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.
The M is selected from the group consisting of compounds containing ^{Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ^{+; and ammonium structures.}
The M1, M2 and Y are the same or different from each other and are independently selected from the group consisting of substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heteroaryl groups. At least one of R13 to R17 is an anionic group and
X is an anionic group,
a is 0 or 1 and
r5 and r6 are integers from 0 to 4 and
When r5 is 2 or more, R5 are the same or different from each other.
When r6 is 2 or more, R6 are the same or different from each other.

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

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

One embodiment of the present specification provides a color filter containing the photosensitive material.

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

The compound according to one embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, can reduce the dispersion step by having solubility in an organic solvent, and can be dispersed when a conventional pigment is applied. The compound can be used as a colorant in an economical way, as opposed to having to go through a process. Further, by reducing the fluorescence intensity, the light-dark ratio can be improved without adding an additional dye.

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

It is a figure which shows the detected fluorescence intensity of the substrate manufactured using the compound by a part of Examples and Comparative Examples of this specification. It shows the visual feeling of the compound which concerns on one Embodiment of this specification. It shows the permeability of the substrate produced by using the compound according to a part of Examples and Comparative Examples of this specification.

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

As used herein, when one member is located "above" another member, this is not only when one member is in contact with another member, but also between the two members. Including the case where the member of is present.

In the present specification, when a component is referred to as "contains" a component, this means that the other component can be further included rather than excluding the other component unless otherwise specified. do.

According to one embodiment of the present specification, the compound represented by the chemical formula 1 is provided.

The present invention has excellent solubility in an organic solvent by containing the compound represented by the chemical formula 1. Specifically, in the above chemical formula 1, the aryl group substituted with nitrogen in the Xanthene structure is substituted with a substituent containing sulfur (S), and the volume is large such as a dianhydride group containing a nitrogen atom. By including a substituent, the solubility in an organic solvent can be increased.

Further, when the aryl group in which the chemical formula 1 is substituted with nitrogen having a xanthene structure is substituted with a substituent containing sulfur (S), the fluorescence intensity is lower than when it is substituted with a substituent containing no sulfur (S). Therefore, an excellent light-dark ratio can be obtained without adding an additional dye.

By increasing the solubility due to this, it is possible to prevent agglutination between the coloring materials from occurring, and by reducing the amount of the material required for dispersing the coloring materials, it is possible to improve economic efficiency.

In addition, the light-dark ratio (CR, Contrast Ratio) can be improved, and excellent heat resistance can be obtained. In order to reduce the luminescence (fluorescence or phosphorescence) of a molecule, there is a method of reducing the flatness in the molecule or introducing a molecule that absorbs the luminescence. When a molecule that absorbs light emission is introduced, it is difficult to selectively absorb only the light having an emission wavelength because it absorbs the light of the desired light emitting molecule and all the external light. Therefore, in order to reduce the flatness in the molecule, a substituent (bulky group) having a large steric hindrance is introduced.

When a molecule that has absorbed light in the ground state and has become an excited state transfers energy in a vibration mode or a rotation mode, non-radiation (non-) Radiative decay) can occur. That is, the light emission can be reduced.

The greater the flatness, the more difficult non-radiant radiation is and the higher the intensity of light emission, and the more the flat area is reduced by introducing a large substituent, the more the intensity of light emission due to non-radiant radiation can be reduced. For non-radiative radiation, long alkyl groups, branched alkyl groups, alkoxy groups, amine groups can be introduced. However, in the case of alkyl, there is a drawback that the heat resistance is insufficient.

Then, in the case of alkoxy and amine groups, they can act as electron donating groups to change the absorption wavelength of light-absorbing molecules.

On the other hand, when a molecule containing sulfur (S) is introduced, the role of an electron donating group in the molecule that absorbs light is reduced, and heat resistance can be maintained.

When a sulfur atom (sulfur atom), which has a larger atomic size than carbon, nitrogen, and oxygen, is introduced, the energy of the excited molecule is transferred to the sulfur atom (sulfur atom) having various energy levels, and the sulfur atom becomes Non-radiative decay can occur while moving through various energy levels, i.e., moving in vibration mode, rotation mode. Due to such properties, when a sulfur atom (sulfur atom) is introduced, the intensity of light emission in the molecule can be reduced.

When a molecule having light emission is applied to a liquid crystal display (LCD), it may cause a decrease in the contrast ratio (CR), which may cause a problem of quality deterioration. Therefore, we take various approaches on how to reduce luminescence.

Currently, in order to suppress the decrease in the light-dark ratio (CR, Contrast Ratio), a molecule that absorbs light emission is introduced. However, the color purity has decreased and the amount of coloring material used has increased.

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

および

は、他の置換基または結合部に結合する部位を意味する。 In the present specification

and

Means a site that binds to another substituent or bond.

As used herein, the term "substituted or unsubstituted" refers to a heavy hydrogen; halogen group; nitrile group; nitro group; -OH; carbonyl group; ester group; -COOH; imide group; amide group; anionic group. Alkoxy group; alkyl group; cycloalkyl group; alkenyl group; cycloalkenyl group; arylalkyl group; phosphine group; sulfonate group; amine group; aryl group; heteroaryl group; silyl group; boron group; acryloyl group; acrylate group; Ether group; substituted with one or more substituents selected from the group containing a heterocyclic group containing one or more of N, O, S, or P atoms and an anionic group, or any It also means that it does not have a substituent.

As used herein, the "adjacent" group is a substituent substituted with an atom in which the substituent is directly linked to the substituted atom, a substituent located sterically closest to the substituent, or the said one. It can mean another substituent in which the substituent is substituted with the substituted atom. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted on the same carbon in the aliphatic ring are interpreted as "adjacent" groups to each other.

In the present specification, the said ring means an aromatic or aliphatic ring in that adjacent groups may be combined to form a "ring". Specifically, the ring may be an aromatic ring, or may be an aryl group or a heteroaryl group. The description below can be applied to the aryl group and the heteroaryl group.

Examples of halogen groups herein include fluorine, chlorine, bromine, or iodine.

As used herein, the carbonyl group may be represented by -COR, where R is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or unsubstituted. It may be an aryl group of. The carbon number of the carbonyl group is not particularly limited, but those having 1 to 30 carbon atoms are preferable. Specifically, it may be a compound having the following structure, but is not limited thereto.

As used herein, the ester group may be represented by −COOR, where R is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or unsubstituted. It may be an aryl group of. In the ester group, the oxygen of the ester group may be substituted with a linear, branched or ring-chain alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

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

As used herein, the amide group may have the nitrogen of the amide group substituted with hydrogen, a linear, branched or ring alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. .. Specifically, it may be a compound having the following structural formula, but is not limited thereto.

As used herein, the phosphine group means an alkylphosphine group or an arylphosphine group, and the alkylphosphine group means a phosphine group substituted with an alkyl group. The number of carbon atoms of the alkylphosphine group is not particularly limited, but those of 1 to 20 are preferable. Examples of the alkylphosphine group include a dimethylphosphine group, a diethylphosphine group, a di-n-propylphosphine group, a diisopropylphosphine group, a di-n-butylphosphine group, a di-sec-butylphosphine group, and a di-tert-butyl group. There are, but are not limited to, a phosphine group, a diisobutylphosphine group, a tert-butylisopropylphosphine group, a di-n-hexylphosphine group, a di-n-octylphosphine group, a di-n-methylphosphine group and the like. The arylphosphine group means a phosphine group substituted with an aryl group. The number of carbon atoms of the arylphosphine group is not particularly limited, but those of 6 to 30 are preferable. Examples of the arylphosphine group include, but are not limited to, a diphenylphosphine group, a dibenzylphosphine group, a methylphenylphosphine group, a benzylhexylphosphine group, and a bistrimethylsilylphosphine group.

In the present specification, the anionic group has a chemical bond with the structure of Chemical Formula 1, and the chemical bond can mean an ionic bond. The anionic group is not particularly limited, and for example, US Pat. No. 7,939,644, Japanese Patent Application Laid-Open No. 2006-003080, Japanese Patent Application Laid-Open No. 2006-001917, Japanese Patent Application Laid-Open No. 2005-001917. No. 159926, Japanese Patent Application Laid-Open No. 2007-70288897, Japanese Patent Application Laid-Open No. 2005-071680, Korean Application Publication No. 2007-70000693, Japanese Patent Application Laid-Open No. 2005-111696, Japanese Patent Application Laid-Open No. 2008-249663 No., the anion described in Japanese Patent Application Laid-Open No. 2014-199436 can be applied.

Specific examples of the anionic group include trifluolmethanesulfonic acid anion, bis (trifluoromethylsulfonyl) amide anion, bistrifluolmethanesulfonimide anion, bisperfluoroethylsulfonimide anion, and tetra. Phenylborate anion, tetrax (4-fluorophenyl) borate, tetrax (pentafluorophenyl) borate, tristrifluoromethanesulfonylmethide, SO ₃ ⁻ , CO ₂ ⁻ , SO ₂ N ⁻ SO ₂ CF ₃ , SO ₂ N ⁻ SO ₂ CF ₂ CF ₃ There are, but are not limited to, halogen groups such as fluorine groups, iodine groups, and chlorine groups.

As used herein, anionic groups can have anions themselves or may be present in complex compound form with other cations. Therefore, the total charge of the entire compound molecule of the present invention can change depending on the number of substituted anionic groups. For example, if the chemical formula 1 includes an ammonium structure, one of the ammonium structures has a cation, so that the total charge of the entire molecule is an anion obtained by subtracting 1 from the number of substituted anionic groups. It can have a value from ion to 0.

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

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 1 to 60 are preferable. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another 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 and n-heptyl group. There are, but are not limited to, n-octyl groups. In the present specification, the cycloalkyl group is not particularly limited, but one having 3 to 30 carbon atoms is preferable, and a cyclopentyl group and a cyclohexyl group are particularly preferable, but the cycloalkyl group is not limited thereto.

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

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

In the present specification, the cycloalkenyl group is not particularly limited, but one having 3 to 60 carbon atoms is preferable, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. 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 one having 6 to 60 carbon atoms is preferable, and a monocyclic aryl group or a polycyclic aryl group may be used. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, an indenyl group, a phenanthrenyl group, a pyrenyl group, a peryleneyl group, a triphenyl group, a chrysenyl group, a fluorenyl group or the like, but is limited thereto. is not it.

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

などのスピロフルオレニル基、

（９，９−ジメチルフルオレニル基）、および

（９，９−ジフェニルフルオレニル基）などの置換されたフルオレニル基になってもよい。ただし、これに限定されるものではない。 If 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-diphenylfluorenyl group). However, the present invention is not limited to this.

In the present specification, specifically, the aryl alkyl group may have an aryl moiety having 6 to 30 carbon atoms and an alkyl moiety 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-fluorbenzyl group, 3,5-difluorbenzyl group, α, α-ditrifluoromethylbenzyl group , P-methoxybenzyl group, m-methoxybenzyl group, α-phenoxybenzyl group, α-benzyloxybenzyl group, naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, pyrrolylethyl group, aminobenzyl group, nitrobenzyl There are, but are not limited to, a group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group, and the like.

In the present specification, the heterocyclic group is a heterocyclic group containing O, N, or S as a hetero atom, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 30, specifically, the number of carbon atoms. 2 to 20. Examples of heterocyclic groups include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxidazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acrizyl group, imidazole group and quinolinyl. Groups, isoquinoline groups, indol groups, carbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, benzofuranyl groups, dibenzofuran groups, etc., but are limited to these. It's not something.

In the present specification, the above-mentioned description of the heterocyclic group is applicable except that the heteroaryl group is aromatic.

In the present specification, the silyl group may be represented by the chemical formula of −SiZ1Z2Z3, and Z1, Z2 and Z3 are hydrogen; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group, respectively. May be good. Specifically, the silyl group includes a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like. However, it is not limited to these.

In the present specification, the alkylsulfoxy group includes, but is not limited to, a methylsulfoxy group, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group and the like. As the alkyl group in the alkyl sulfoxy group, the above-mentioned description regarding the alkyl group can be applied.

In the present specification, the boron group may be represented by the chemical formula of −BW4W5, and the W4 and W5 may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, respectively. .. Specific examples of the boron group include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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

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

As used herein, the term "(meth) acryloyl" refers to at least one selected from the group consisting of acryloyl and meta-acryloyl. The notation of "(meth) acrylate" has the same meaning.

As used herein, the ether group may be represented by −COR. The R is a substituted or unsubstituted alkyl group. As for the alkyl group, the above-mentioned description of the alkyl group can be applied.

As used herein, the sulfonate group may be an alkyl sulfonate group or an aryl sulfonate group. The above-mentioned description regarding the alkyl group can be applied to the "alkyl", and the above-mentioned description regarding the aryl group can be applied to the "aryl".

As used herein, the amine group consists of -NH ₂ ; alkylamine group; N-alkylarylamine group; arylamine group; N-arylheteroarylamine group; N-alkylheteroarylamine group and heteroarylamine group. It may be selected from the group, and the number of carbon atoms is not particularly limited, but those of 1 to 30 are preferable. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9-methyl-anthrasenylamine group, and a diphenylamine group. N-phenylnaphthylamine group, ditrilamine group, N-phenyltrilamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N- Phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group However, it is not limited to these.

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

As used herein, an alkylene group means an alkane having two bonding positions. The alkylene group may be a straight chain, a branched chain or a ring chain. The carbon number of the alkylene group is not particularly limited, but is, for example, 1 to 30, specifically 1 to 20, and more specifically 1 to 10.

As used herein, a heteroalkylene group means an alkane containing O, N, or S as a hetero atom having two bond positions. The heteroalkylene group may be a straight chain, a branched chain or a ring chain. The number of carbon atoms of the heteroalkylene group is not particularly limited, but is, for example, 2 to 30 carbon atoms, specifically 2 to 20 carbon atoms, and more specifically 2 to 10 carbon atoms.

As used herein, an arylene group means an aryl group having two bonding positions, that is, a divalent group. The above description of the aryl group is applicable, except that each of these is a divalent group.

As used herein, a heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the above-mentioned description of the heteroaryl group is applicable.

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

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

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

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

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

In one embodiment of the specification, L1 and L2 of Chemical Formula 1 are the same or different from each other and are independently methylene group; ethylene group; propylene group; or butylene group.

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

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

In one embodiment of the specification, R1 and R2 of Chemical Formula 1 are dianhydride groups that are identical or different from each other and each independently contain a nitrogen atom having 4 to 15 carbon atoms.

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

は、前記化学式１に連結される部位を示し、
Ｘ１、Ｘ２およびＹ１〜Ｙ３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトロ基；−ＯＨ；−ＳＯ_３Ｈ；−ＣＯＯＨ；ホスフィン基；陰イオン性基；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であるか、隣接する基は、結合して置換もしくは非置換の環を形成する。 In the substituent

Indicates a site linked to the above chemical formula 1.
X1, X2 and Y1 to Y3 are the same or different from each other and are independent of each other: hydrogen; heavy hydrogen; halogen group; nitro group; -OH; -SO ₃ H; -COOH; phosphine group; anionic group; substituted or An unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent groups are bonded to form a substituted or unsubstituted ring.

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

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

In one embodiment of the present specification, the X1 and X2, _-SO 3 M combine with each other; or a substituted or unsubstituted benzene ring with _-SO 2 NHY; with or _-SO 2 NHY; or _-SO 3 M Substituted or unsubstituted naphthalene rings may be formed, and M and Y are as defined in the chemical formula 1.

In one embodiment of the present specification, the X1 and X2, _-SO 3 M combine with each other; or a substituted or unsubstituted benzene ring with _-SO 2 NHY; with or _-SO 2 NHY; or _-SO 3 M Substituted or unsubstituted naphthalene rings may be formed, the M being selected from the group consisting of compounds containing hydrogen; Na; K; Rb; Cs; Fr; and ammonium structures, and the Y being substituted or unsubstituted. It is a substituted alkyl group.

In one embodiment of the present specification, the X1 and X2, _-SO 3 M combine with each other; or a substituted or unsubstituted benzene ring with _-SO 2 NHY; with or _-SO 2 NHY; or _-SO 3 M Substituted or unsubstituted naphthalene rings may be formed, the M being selected from the group consisting of compounds containing hydrogen; Na; K; Rb; Cs; Fr; and ammonium structures, and the Y being substituted or unsubstituted. It is a substituted n-hexyl group.

In one embodiment of the present specification, the X1 and X2, _-SO 3 M combine with each other; or a substituted or unsubstituted benzene ring with _-SO 2 NHY; with or _-SO 2 NHY; or _-SO 3 M Substituted or unsubstituted naphthalene rings may be formed, and the M is selected from the group consisting of compounds containing hydrogen; Na; K; Rb; Cs; Fr; and an ammonium structure, and the Y is an ethyl group. It is a substituted n-hexyl group.

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

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

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

In one embodiment of the specification, the Y1 and Y2; and Y2 and Y3 may combine to form a -SO ₃ M; or -SO ₂ NHY substituted or unsubstituted benzene ring. Is ^{selected from the group consisting of Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; and compounds containing ammonium structures, where Y is a substituted or unsubstituted alkyl group.

In one embodiment of the specification, the Y1 and Y2; and Y2 and Y3 may combine to form a -SO ₃ M; or -SO ₂ NHY substituted or unsubstituted benzene ring. Is ^{selected from the group consisting of Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; and compounds containing ammonium structures, where Y is a substituted or unsubstituted n-hexyl group.

In one embodiment of the specification, the Y1 and Y2; and Y2 and Y3 may combine to form a -SO ₃ M; or -SO ₂ NHY substituted or unsubstituted benzene ring. Is ^{selected from the group consisting of Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; and compounds containing an ammonium structure, where Y is an ethyl group substituted n-hexyl group.

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

は、前記化学式１に連結される部位を示し、Ｘ３〜Ｘ５およびＹ４は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトロ基；−ＯＨ；−ＳＯ_３Ｈ；；−ＳＯ_３Ｍ；−ＳＯ_２ＮＨＹ；−ＣＯＯＨ；ホスフィン基；陰イオン性基；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であり、前記ＭおよびＹは、前記化学式１で定義した通りであり、ｘ３は、０〜４の整数、ｘ４、ｘ５およびｙ４は、０〜６の整数である。 In the substituent

Indicates a site linked to the chemical formula 1, and X3 to X5 and Y4 are the same or different from each other, and are independently hydrogen; heavy hydrogen; halogen group; nitro group; -OH; -SO ₃ H ;;-. SO ₃ M; -SO ₂ NHY; -COOH; phosphine group; anionic group; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group, wherein M and Y are defined by the above chemical formula 1. As described above, x3 is an integer of 0 to 4, and x4, x5 and y4 are integers of 0 to 6.

は、前記化学式１に連結される部位を示し、Ｘ３〜Ｘ５およびＹ４は、互いに同一または異なり、それぞれ独立に、水素；−ＳＯ_３Ｍ；または−ＳＯ_２ＮＨＹであり、前記ＭおよびＹは、前記化学式１で定義した通りであり、ｘ３は、０〜４の整数、ｘ４、ｘ５およびｙ４は、０〜６の整数である。 In the substituent

Indicates a site linked to the chemical formula 1, where X3 to X5 and Y4 are the same or different from each other and are independently hydrogen; -SO ₃ M; or -SO ₂ NHY, where M and Y are. As defined in Chemical Formula 1, x3 is an integer of 0 to 4, and x4, x5 and y4 are integers of 0 to 6.

In one embodiment of the present specification, R3 and R4 of Chemical Formula 1 are identical or different from each other and are independently substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms; or substituted or substituted with 6 to 30 carbon atoms. It is an unsubstituted aryl group.

In one embodiment of the present specification, R3 and R4 of Chemical Formula 1 are identical or different from each other and are independently substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; or substituted or substituted with 6 to 20 carbon atoms. It is an unsubstituted aryl group.

In one embodiment of the present specification, R3 and R4 of Chemical Formula 1 are identical or different from each other and are independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms; or substituted or substituted with 6 to 20 carbon atoms. It is an unsubstituted aryl group.

In one embodiment of the specification, R3 and R4 of Chemical Formula 1 are the same or different from each other and are independently substituted or unsubstituted methyl groups; or substituted or unsubstituted phenyl groups.

In one embodiment of the specification, R3 and R4 of Chemical Formula 1 are the same or different from each other and are independently methyl groups; methyl groups substituted with halogen groups; or phenyl groups.

In one embodiment of the specification, R3 and R4 of Chemical Formula 1 are the same or different from each other and are independently methyl groups; trifluolmethyl groups (-CF ₃ ); or phenyl groups.

In one embodiment of the present specification, R5 to R12 of the chemical formula 1 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitro group; hydroxy group; -COR; -COOR; imide group; Amid group; anionic group; substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms. Substituent or unsubstituted alkenyl group having 2 to 30 carbon atoms; Substituent or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms; Substituent or unsubstituted sulfonate group; Substituent or unsubstituted amine having 1 to 30 carbon atoms Selected from the group consisting of a group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

The R is a 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. be.

In one embodiment of the specification, the R5 to R12 of the chemical formula 1 are identical or different from each other and independently of each other, hydrogen; heavy hydrogen; halogen group; -OH; -SO ₃ H; -SO ₃ M; -SO. ₂ NM1M2; -SO ₂ NHY; -COOH; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted cycloalkenyl group; substituted or unsubstituted Selected from the group consisting of aryl groups; and substituted or unsubstituted heteroaryl groups, said M is selected from the group consisting of Na ⁺ ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; and compounds containing ammonium structures. , M1, M2 and Y are the same or different from each other and are independently selected from the group consisting of substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heteroaryl groups. ..

In one embodiment of the present specification, R5 to R12 of Chemical Formula 1 are the same or different from each other and are independently hydrogen; -SO ₂ NHY; or substituted or unsubstituted alkyl groups, wherein Y is substituted. Alternatively, it is an unsubstituted alkyl group.

In one embodiment of the specification, R5 to R12 of Chemical Formula 1 are the same or different from each other and are independently hydrogen; -SO ₂ NHY; or substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms. , 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 Chemical Formula 1 are the same or different from each other and are independently hydrogen; -SO ₂ NHY; or substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms. , Y is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

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

In one embodiment of the specification, R5 to R12 of Chemical Formula 1 are the same or different from each other and are independently hydrogen; -SO ₂ NHY; or substituted or unsubstituted methyl groups, where Y is carbon. It is a hexyl group substituted or unsubstituted with several 1 to 10 carbon atoms.

In one embodiment of the present specification, R5 to R12 of Chemical Formula 1 _{are methyl groups that are identical or different from each other and are independently substituted or unsubstituted with hydrogen; -SO 2} NHY; or a halogen group, and the Y Is a hexyl group substituted or unsubstituted with an ethyl group.

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

In one embodiment of the specification, R5 of Chemical Formula 1 is hydrogen; or a trifluormethyl group.

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

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

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

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

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

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

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

Further, in one embodiment of the present specification, R13～R17, equal to or different from each other, each independently, hydrogen, deuterium, ^{_{halogen; -OH; -SO 3 -; -SO}} 3 H; -SO 3 M -SO ₂ NM1M2; -SO ₂ NHY; -COOH; anionic group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted A heteroaryl group, the M is ^{selected from the group consisting of compounds containing Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; and ammonium structures, the M1, M2 and Y being the same or different from each other. , Each independently selected from the group consisting of substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heteroaryl groups, and at least one of the above R13 to R17 is negative. It is an ionic group.

In one embodiment herein, R13～R17, equal to or different from each other, each independently, ^{_{hydrogen; -SO 3 -; -SO 3 M}} ; a or _-SO 2 NHY, wherein M and Y are previously As defined in the above, at least one of R13 to R17 is an anionic group.

In one embodiment herein, R13～R17, equal to or different from each other, each independently, ^{_{hydrogen; -SO 3 -; -SO 3 M}} ; a or _-SO 2 NHY, wherein M and Y are previously are as defined, at least one of said R13~R17 is, -SO ₃ ^- is.

In one embodiment herein, R13 is, -SO ₃ ^- is.

In one embodiment of the specification, R14 is hydrogen.

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

In one embodiment of the specification, R16 is hydrogen.

In one embodiment of the specification, R17 is hydrogen.

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

In one embodiment of the specification, X is an anion of a compound containing at least one element and oxygen selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus; a trifluolmethanesulfonic acid anion; Bis (trifluoromethylsulfonyl) amide anion; bistrifluolmethanesulfonimide anion; bisperfluoroethylsulfonimide anion; tetraphenylborate anion; tetrakis (4-fluorophenyl) borate; tetrakis (pentafluorophenyl) ) Bolate; tristrifluoromethanesulfonylmethide; and a compound selected from the group consisting of halogen groups.

In one embodiment herein, X is, SO ₃ ^- may be.

Further, in one embodiment of the present specification, r5 and r6 are integers of 0 to 4, and when r5 is 2 or more, R5 are the same or different from each other, and when r6 is 2 or more, R6 are mutual. Same or different.

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

In one embodiment of the specification, r5 and r6 are integers from 0 to 2, and if r5 is 2, then R5 is the same or different from each other, and if r6 is 2, then R6 is the same or different from each other.

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

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

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

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

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

The description of the isomer is applicable to all of the xanthene dye structures described herein.

In one embodiment of the present specification, the -SO 3 _M is, -SO ₃ ^- can mean to that M is an ion or salt linkage.

In one embodiment of the present specification, the M is ^{selected from the group consisting of Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ⁺ ; and a compound containing an ammonium structure, and the compound containing the ammonium structure is described below. It can contain a unit represented by the chemical formula A or represented by the following chemical formula B.

[Chemical formula A]

[Chemical formula B]

In the chemical formula A,
Ra to Rd are the same or different from each other, and independently of each other, 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, wherein the R is hydrogen; substituted or substituted or An unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted arylalkyl group, wherein L ₁ and L ₂ are substituted or unsubstituted alkylene groups.

In the chemical formula B,
Rb to Rd are the same or different from each other and are independently hydrogen; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted arylalkyl group. Or, two of Rb to Rd combine with each other to form a substituted or unsubstituted ring, where Z is a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; -L _3- NHCO. -; Or -L _4- OCO-, wherein L ₃ and L ₄ are substituted or unsubstituted alkylene groups, and Re to Rg are the same or different from each other and are independently hydrogen; or substituted or non-substituted. It is a substituted alkyl group.

According to one embodiment of the present specification, in the chemical formula A, Ra to Rd are the same or different from each other, and are independently hydrogen; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms; 1 to 1 carbon atoms. 30-substituted or unsubstituted alkenyl groups; 6-30 carbon-substituted or unsubstituted aryl groups; 6-30 carbon-substituted or unsubstituted arylalkyl groups; -L _1- NHCO-R; or -L _2- OCO-R or two of Ra to Rd are bonded to each other to form a substituted or unsubstituted ring, and the R is a hydrogen; a substituted or unsubstituted alkyl having 1 to 30 carbon atoms. A group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, wherein L ₁ and L ₂ are substituted or substituted having 1 to 30 carbon atoms. It is an unsubstituted alkylene group and

In the chemical formula B, Rb to Rd are the same or different from each other, and independently, hydrogen; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms; carbon. Substituted or unsubstituted aryl group of number 6 to 30; or substituted or unsubstituted arylalkyl group of carbon number 6 to 30, or two of Rb to Rd are bonded to each other and substituted or unsubstituted. Forming a ring, Z is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; -L _3- NHCO-; or -L _4- OCO-. L ₃ and L ₄ are substituted or unsubstituted alkylene groups having 1 to 30 carbon atoms, and Re to Rg are the same or different from each other, and are independently hydrogen; or 1 to 30 carbon atoms. It is a substituted or unsubstituted alkyl group.

According to one embodiment of the present specification, in the chemical formula A, Ra to Rd are the same or different from each other, and are independently hydrogen; substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; 1 to 1 carbon atoms. 20-substituted or unsubstituted alkenyl groups; 6-20 carbon-substituted or unsubstituted aryl groups; 6-20 carbon-substituted or unsubstituted arylalkyl groups; -L _1- NHCO-R; or -L _2- OCO-R or two of Ra to Rd are bonded to each other to form a substituted or unsubstituted ring, and the R is a hydrogen; a substituted or unsubstituted alkyl having 1 to 20 carbon atoms. A group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted arylalkyl group having 6 to 20 carbon atoms, wherein L ₁ and L ₂ are substituted or substituted having 1 to 20 carbon atoms. It is an unsubstituted alkylene group and

In the chemical formula B, Rb to Rd are the same or different from each other, and independently, hydrogen; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms; carbon. Substituted or unsubstituted aryl group of number 6 to 20; or substituted or unsubstituted arylalkyl group of carbon number 6 to 20, or two of Rb to Rd are bonded to each other and substituted or unsubstituted. Forming a ring, Z is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; -L _3- NHCO-; or -L _4- OCO-. L ₃ and L ₄ are substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms, and Re to Rg are the same or different from each other and are independently hydrogen; or 1 to 20 carbon atoms. It is a substituted or unsubstituted alkyl group.

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

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

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

In one embodiment of the present specification, the weight average molecular weight of the compound containing the unit represented by the chemical formula B may be 1000 to 10000, preferably 3,000 to 8,000, and more preferably 3,000 to 8,000. It is 5,000 to 7,000.

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

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

[Chemical formula 2]

In the chemical formula 2,
L1, L2, R1 to R17, X, a, r5 and r6 are as defined in the above chemical formula 1.

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

[Chemical formula 3]

In the chemical formula 3,
L1, L2, R1 to R17, X, a, r5 and r6 are as defined in the above chemical formula 1.

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

[Chemical formula 4]

In the chemical formula 4,
L1, L2, R1 to R17, X, a, r5 and r6 are as defined in the above chemical formula 1.

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

は、前記化学式１に連結される部位を示し、
Ｘ１、Ｘ２、Ｙ１〜Ｙ３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；ニトロ基；−ＯＨ；−ＳＯ_３Ｈ；；−ＣＯＯＨ；ホスフィン基；陰イオン性基；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であるか、隣接する基は、結合して置換もしくは非置換の環を形成してもよい。 In the substituent

Indicates a site linked to the above chemical formula 1.
X1, X2, Y1 to Y3 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitro group; -OH; -SO ₃ H ;; -COOH; phosphine group; anionic group; substitution. Alternatively, it may be an 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 the chemical formula 1 may be represented by any one of the following chemical formulas.

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

In one embodiment of the present specification, a substituent in the ring of the chemical formula whose substitution position is not specified means that any portion of carbon contained in the ring may be substituted.

において、

for example,

In

Means that the benzene ring substituted with -CF ₃ may be substituted with any one of the remaining carbons excluding the carbon substituted with _{-SCH 3, specifically, the following.} It may be represented by the four structures of.

において、

は、−ＳＯ_２ＮＨＹで置換されたナフタレン環において、ナフタレンに含まれる炭素のうちのいずれか１つに置換されてよいことを意味し、具体的には、下記の６つの構造で表されてもよい。 As another example

In

Means that the naphthalene ring substituted with -SO ₂ NHY may be substituted with any one of the carbons contained in naphthalene, and specifically, it is represented by the following six structures. May be good.

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

Further, according to one embodiment of the present specification, a color material composition containing the compound can be provided.

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

According to one embodiment of the present specification, it is possible to provide a photosensitive resin composition containing the coloring material composition.

According to one embodiment of the present specification, the photosensitive resin composition may further contain the compound represented by the chemical formula 1, a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent.

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

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

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

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl (meth) acrylate. , T-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (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, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl Ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1, , 1,1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate , Ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate, and butyl α-hydroxymethyl acrylate may be selected from the group, but is not limited thereto.

Specific examples of the aromatic vinyls include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p) -chloro. It may be selected from the group consisting of styrene, 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 may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. , Not limited to these.

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

The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group, and for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2- Selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, ω-carboxypolycaprolactone mono (meth) acrylate. It is preferable to use one or more, but the present invention is not limited to these.

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

The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light, and specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6 -Hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethyl alcohol diacrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, penta It may be one or a mixture of two or more selected from the group consisting of erythritol tetramethacrylate and dipentaerythritol hexamethacrylate.

The photoinitiator is not particularly limited as long as it is an initiator that promotes cross-linking by generating radicals with light, but is, for example, from the group consisting of an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound. It may be one or more selected.

The acetphenone compounds are 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 4- (2-). Hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, 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-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, 2-( 4-Bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one And are not limited to these.

Examples of the biimidazole compound include 2,2-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 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 and the like, but not limited to these.

The triazine compounds are 3-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2-{4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, cyclohexyl-2-{4- [ 2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} Acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazine-6-yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s -Triazine-6-yl] phenylthio} propionamide, 2,4-bis (trichloromethyl) -6-p-methoxystyryl-s-triazine, 2,4-bis (trichloromethyl) -6- (1-p-) Dimethylaminophenyl) -1,3-butadienyl-s-triazine, 2-trichloromethyl-4-amino-6-p-methoxystyryl-s-triazine, and the like, but not limited to these.

The oxime compounds are 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigy, CGI124), etanone, -1- (9-ethyl) -6. -(2-Methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGI242), N-1919 (Adeka Corporation) and the like, and are not limited thereto.

The solvents used are 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, and 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-trichloroethane, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl One or more selected from the group consisting of ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether. There may be, but it is not limited to this.

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

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

Specifically, the photosensitive resin composition has a content of the compound represented by the chemical formula 1 of 5% by weight to 50% by weight based on the total weight of the solid content in the photosensitive resin composition. The content of the binder resin is 1% by weight to 50% by weight, the content of the photoinitiator is 0.1% by weight to 10% by weight, and the content of the polyfunctional monomer is 0. It is 1% by weight to 45% by weight.

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

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

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

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

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

According to one embodiment of the present specification, the photosensitive resin composition comprises a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and the like. It additionally comprises one or more additives selected from the group consisting of dispersants and leveling agents.

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

According to one embodiment of the present specification, the photosensitive resin composition comprises a photocrosslinking sensitizer, a curing accelerator, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant, and a dispersant. It additionally comprises one or more additives selected from the group consisting of leveling agents.

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

The photocrosslinking sensitizer includes benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3, Benzophenone compounds such as 3-dimethyl-4-methoxybenzophenone, 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 -Fluolenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone; xanthone, 2-methylxanthone and the like. Xanthone compounds; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butyl anthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylaclydin, 1,7-bis ( Acrydin compounds such as 9-acrydinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7,7-trimethyl-bicyclo [2] , 2,1] Dicarbonyl compounds such as heptane-2,3-dione, 9,10-phenanthrenquinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4 , 4-trimethylpentylphosphine oxide and other phosphine oxide compounds; methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate and the like. Benzoate compounds; 2,5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl -Amino synergists such as 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-carboni Rubis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolidine-11-one, etc. One or more selected from the group consisting of chalcone compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene and 3-methyl-b-naphthiazoline; can be used. ..

As the curing accelerator, it is used to enhance curing and mechanical strength, and specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-Thiazazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2) -Selected from the group consisting of pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) 1 More than seeds can be used.

Adhesion promoters used herein include metaacryloylsilane coupling agents such as metaacryloyloxypropyltrimethoxysilane, metaacryloyloxypropyldimethoxysilane, metaacryloyloxypropyltriethoxysilane, and metaacryloyloxypropyldimethoxysilane. One or more of them can be selected and used, and as the alkyltrimethoxysilane, one or more can be selected and used from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like. ..

The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant is BYK-077, BYK-085, BYK-300, BYK of BYK-Chemie. -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 can be used, and as the fluorine-based surfactant, F-114, F-177, F-410, F-411, F-450, F-493, F of DIC (Dai Nippon Inc & Chemicals) can be used. -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. can be used, but are limited thereto. is not it.

The antioxidant is one or more selected from the group consisting of a hidden phenolic antioxidant, an amine-based antioxidant, a thio-based antioxidant, and a phosphine-based antioxidant. It may be, but it is not limited to this.

Specific examples of the antioxidant are phosphate-based heat 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-hydroxybenzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzyl phosphite 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'-tart-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-) Hindered phenyl primary antioxidants such as 3'-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-phenylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p- Amine-based secondary antioxidants such as phenylenediamine, or N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzo Thio-based secondary antioxidants such as thiazole, or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, Bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Phenaerythritol Diphosphite, or (1,1'-biphenyl) -4,4'-diylbisphosphonoate tetrakis [2, 4-Bis (1,1-Dimethylethyl) Phenyl] Ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous aci Examples thereof include phosphite-based secondary antioxidants such as d tetrakis [2,4-bis (1,1-dimethyl) phenyl] ester).

As the ultraviolet absorber, 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole, alkoxybenzophenone and the like can be used, but the ultraviolet absorber is not limited thereto. Anything commonly used in the industry can be used.

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, and N-nitrosophenyl hydroxyamine aluminum salt. , P-methoxyphenol, di-t-butyl-p-cresol, pyrogallol, benzoquinone, 4,4-thiobis (3-methyl-6-t-butylphenol), 2,2-methylenebis (4-methyl-6-t) It can include, but is not limited to, one or more selected from the group consisting of −butylphenol), 2-mercaptoimidazole, and phenothiazine, but is generally known in the art. Can include those that are.

The dispersant can be used by a method of internally adding the pigment to the pigment in a form of surface treatment in advance, or a method of externally adding the pigment to the pigment. As the dispersant, a compound type, nonionic, anionic or cationic dispersant can be used, and a fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, amphoteric surfactant can be used. Activators and the like can be mentioned. These can be used individually or in combination of two or more.

Specifically, the dispersant includes polyalkylene glycol and its ester, polyoxyalkylene polyhydric alcohol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonate, carboxylic acid ester, and carboxylic acid. There is, but is not limited to, one or more selected from the group consisting of salts, alkylamide alkylene oxide adducts, and alkylamines.

The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamideamines, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymeric sulfur-containing and Any commonly used in the art can be used, including but not limited to non-polymer nitrogen-containing compounds.

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

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

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

Examples of the light source for curing the photosensitive resin composition according to the present specification include mercury vapor arc (arc), carbon arc, and Xe arc that emit light having a wavelength of 250 nm to 450 nm, but these are not necessarily the same. Not limited to.

The photosensitive resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film liquid crystal display (TFT LCD) color filter, a thin film liquid crystal display (TFT LCD), or a photosensitive material for forming a black matrix of an organic light emitting diode. , Photosensitive material for overcoat layer formation, Column spacer photosensitive material, Photocurable paint, Photocurable ink, Photocurable adhesive, Printing plate, Photosensitive material for printing wiring board, Photosensitive material for plasma display panel (PDP), etc. It can be used for, and there are no particular restrictions on its use.

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

The color filter is produced by using a photosensitive resin composition containing the compound represented by the chemical formula 1. A color filter can be formed by applying the photosensitive resin composition onto a substrate to form a coating film, and exposing, developing, and curing the coating film.

The photosensitive resin composition according to one embodiment of the present specification has excellent heat resistance, little color change due to heat treatment, high color reproduction rate even during manufacturing of a color filter and a curing process, and brightness and lightness and darkness. A color filter having a high ratio can be provided.

The substrate may be a glass plate, a silicon wafer, a plate of a plastic base material such as polyethersulfone (PES) or polycarbonate (PC), and the type thereof is not particularly limited. No.

Specifically, the photosensitive resin composition according to one embodiment of the present specification ^{is spin-coated on glass (5 × 5 cm 2} ) and preheated (prebake) at 100 ° C. for 100 seconds to form a film. Can be formed. The distance between the substrate on which the film is formed and the photomask (photomask) is set to 250 um, and the entire surface of the substrate is irradiated with an exposure amount ^{of 40 mJ / cm 2 using an exposure device.} After that, the exposed substrate can be developed in a developing solution (potassium hydroxide (KOH), 0.05%) for 60 seconds and then heat-treated (postbake) at 230 ° C. for 20 minutes to prepare a substrate.

The heat resistance evaluation is measured by a method described later. The substrate produced by the above embodiment is used with a spectroscope to obtain a transmittance spectrum in the visible light region in the range of 380 nm to 780 nm. Further, the preheat treatment (prebake) substrate is additionally heat-treated (postbake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum with the same equipment and measurement range.

The spectroscope may be manufactured by MCPD-Otsuka, but is not limited thereto.

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

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

The light-dark ratio is measured by a method described later. Using a light-dark ratio measuring device, the substrate produced by the method for producing the substrate is inserted between the two polarizing plates, and the brightness when the two polarizing plates are horizontal and the brightness of the two polarizing plates are displayed. The brightness when the polarizing plates are orthogonal to each other is measured, and the light-dark ratio is calculated by the following formula 2.

[Calculation formula 2]
Brightness / darkness ratio = brightness when two polarizing plates are horizontal / brightness when two polarizing plates are vertical

The light-dark ratio measuring device may be made by CT-1, ZOENTEC, but is not limited thereto.

The fluorescence intensity of the color filter according to one embodiment of the present specification is such that the substrate is fluorescent using Sinco's FS-2 fluorescence measurement equipment at room temperature (25 ° C.), with an excitation wavelength of 545 nm and an extrusion wavelength of 560 nm to 720 nm. The strength can be measured.

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

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

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

The black matrix can use a black pigment or a black dye as a coloring material. For example, carbon black can be used alone or a mixture of carbon black and a coloring pigment can be used. At this time, since the coloring pigment having insufficient light-shielding property is mixed, the amount of the coloring material is relatively large. There is an advantage that the strength of the film or the adhesion to the substrate does not decrease even if the amount is increased.

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

The display device includes a plasma display panel (Plasma Display Panel, PDP), a light emitting diode (Light Emitting Device, LED), an organic light emitting element (Organic Light Emitting Device, OLED), a liquid crystal display device (Liquid Crystal Display), and a liquid crystal display device (Liquid Crystal Display). It may be any one of a liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, LCD-TFT) and a cathode line tube (Casode Ray Tube, CRT).

<Example>

<Example of compound synthesis>

Synthesis Example 1: Synthesis of Compound 1

Synthesis of intermediate 1

A-15 g (12.34 mmol), B-1 10.31 g (74.03 mmol) and N-methyl-2-pyrrolidone (NMP, N) in a 250 ml 2-neck round bottom flask (RBF, Round Bottom Flask). −Methyl-2-pyrrolidone) 80 g was added and stirred. The temperature was raised to 150 ° C. and the mixture was stirred for 4 hours, the reaction solution was cooled to room temperature, placed in 800 ml of 1M hydrochloric acid (HCl), and stirred for 30 minutes.

Then, the obtained precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 17 g (11.46 mmol) of the intermediate.

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

Synthesis of compound 1

Intermediate 1 1.5 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1 in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask) .358 g (9.82 mmol) was added to N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) in an amount of 30 g, and the mixture was stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes. The precipitate was filtered and washed with water under reduced pressure, separated by 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

In a 250 ml 2-neck round bottom flask (RBF, Round Bottom Flask), A-15 g (12.34 mmol), B-2 14.90 g (74.03 mmol) and N-methyl-2-pyrrolidone (NMP, N). −Methyl-2-pyrrolidone) 80 g was added and stirred. The temperature was raised to 150 ° C. and the mixture was stirred for 4 hours, the reaction solution was cooled to room temperature, placed in 800 ml of 1M hydrochloric acid (HCl), and stirred for 30 minutes.

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

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

Synthesis of compound 2

Intermediate 2 1.808 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1 in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask) .358 g (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

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

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

Synthesis Example 3: Synthesis of Compound 3

Synthesis of intermediate 3

In a 250 ml 2-neck round bottom flask (RBF, Round Bottom Flask), A-15 g (12.34 mmol), B-3 10.31 g (74.03 mmol) and N-methyl-2-pyrrolidone (NMP, N). −Methyl-2-pyrrolidone) 80 g was added and stirred. The temperature was raised to 150 ° C. and the mixture was stirred for 4 hours, the reaction solution was cooled to room temperature, placed in 800 ml of 1M hydrochloric acid (HCl), and stirred for 30 minutes.

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

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

Synthesis of compound 3

Intermediate 3 1.502 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1 in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask) .358 g (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

Then, the precipitate was filtered and washed with water under reduced pressure, separated by 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

In a 250 ml 2-neck round bottom flask (RBF, Round Bottom Flask), A-15 g (12.34 mmol), B-4 10.31 g (74.03 mmol) and N-methyl-2-pyrrolidone (NMP, N). −Methyl-2-pyrrolidone) 80 g was added and stirred. The temperature was raised to 150 ° C. and the mixture was stirred for 4 hours, the reaction solution was cooled to room temperature, placed in 800 ml of 1M hydrochloric acid (HCl), and stirred for 30 minutes.

Then, the precipitate was filtered under reduced pressure, washed with water, and dried in a vacuum oven at 60 ° C. for 12 hours to obtain 46.5 g (10.64 mmol) of the intermediate.

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

Synthesis of compound 4

Intermediate 4 1.502 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1 in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask) .358 g (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered under reduced pressure, washed with water, separated by 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

In a 250 ml 2-neck round bottom flask (RBF, Round Bottom Flask), A-15 g (12.34 mmol), B-5 14.30 g (74.03 mmol) and N-methyl-2-pyrrolidone (NMP, N). −Methyl-2-pyrrolidone) 80 g was added and stirred. The temperature was raised to 150 ° C. and the mixture was stirred for 4 hours, the reaction solution was cooled to room temperature, placed in 800 ml of 1M hydrochloric acid (HCl), and stirred for 30 minutes.

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

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

Synthesis of compound 5

Intermediate 5 1.768 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1 in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask) .358 g (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered under reduced pressure, washed with water, separated by 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

In a 250 ml 2-neck round bottom flask (RBF, Round Bottom Flask), A-15 g (12.34 mmol), B-6 15.33 g (74.03 mmol) and N-methyl-2-pyrrolidone (NMP, N). −Methyl-2-pyrrolidone) 80 g was added and stirred. The temperature was raised to 150 ° C. and the mixture was stirred for 4 hours, the reaction solution was cooled to room temperature, placed in 800 ml of 1M hydrochloric acid (HCl), and stirred for 30 minutes.

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 6,7.4 g (9.91 mmol) of the intermediate.

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

Synthesis of compound 6

Intermediate 6 1.837 g (2.46 mmol), C-1 2.958 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1 in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask) .358 g (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered under reduced pressure, washed with water, separated by 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 production of the compound 1, C-1 was changed to C-2, and compound 7 was obtained by the same method except for the above.

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

Synthesis Example 8: Synthesis of Compound 8

In the production of the compound 2, C-1 was changed to C-2, and compound 8 was obtained by 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 production of the compound 3, C-1 was changed to C-2, and compound 9 was obtained by 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 production of the compound 4, C-1 was changed to C-2, and the 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 production of the compound 5, C-1 was changed to C-2, and compound 11 was obtained by 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 production of the compound 6, C-1 was changed to C-2, and compound 12 was obtained by the same method except for the above.

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

Synthesis Examples 13-18: Synthesis of Compounds 13-18

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

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 = 1085 [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

In a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask), S1 1.414 g (2.46 mmol), bromotropic 1.21 g (9.82 mmol), 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. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered under reduced pressure, washed with water, separated by 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 1.4234 g (2.46 mmol), C-2 3.094 g (9.82 mmol), potassium carbonate (K ₂ CO ₃ ) 1.358 g in a 100 ml 2-neck round bottom flask (RBF, Round Bottom Flask). (9.82 mmol) was added to 30 g of N-methyl-2-pyrrolidone (NMP, N-Methyl-2-pyrrolidone) and stirred. The temperature was raised to 100 ° C. and the mixture was stirred for 6 hours, the reaction solution was cooled to room temperature, then placed in 500 ml of distilled water (DI-Water) and stirred for 30 minutes.

The precipitate was filtered under reduced pressure, washed with water, separated by 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 Synthesis Example 1, Comparative Compound 3 was synthesized using S3 and S4 instead of A-1 and B-1 in the same manner as in the synthesis of Intermediate 1.

Comparative compound 4

13 g (4.553 mmol) of the comparative compound was added to 50 g of 98% sulfuric acid at 10 ° C. and dissolved. Then, 0.807 g (4.553 mmol) of N-hydroxymethylphthalimide was added, the temperature was raised to 45 ° C., and the mixture was 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 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) included) 10.376 g, as photoinitiator I-369 (BASF) 2.018 g, DPHA (Nippon Kayaku), a polyfunctional monomer, 12.443 g, solvent PGMEA (polypropylene glycol monomethyl ether acetate), 68.593 g, and DIC's F-475, 1.016 g as an additive surfactant. Was mixed to produce a photosensitive resin composition 1.

Examples 2-18

In Example 1, Compound 1 was changed to Compounds 2 to 18, and photosensitive resin compositions 2 to 18 were produced with the same composition other than 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, measured by gel permeation chromatography (GPC), 000 g / mol, molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent polypropylene glycol monomethyl ether acetate (PGMEA) included) 10.376 g, as a photoinitiator I-369 (BASF) ) 2.018 g, DPHA (Nippon Kayaku) 12.443 g as a polyfunctional monomer, solvent PGMEA (polypropylene glycol monomethyl ether acetate) 68.593 g, and DIC's F-475 as an additive surfactant, 1. 016 g was mixed to produce a photosensitive resin composition of Comparative Example 1.

Comparative Examples 2-4

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

<Experimental example>

Substrate preparation

The photosensitive resin compositions according to Examples 1 to 18 and Comparative Examples 1 to 4 were used for preparing the substrate, respectively. Specifically, the photosensitive resin compositions according to Examples 1 to 18 and Comparative Examples 1 to 4 ^{are spin coated on glass (5 × 5 cm 2} ) and preheated at 100 ° C. for 100 seconds. ) Was applied to form a film.

The distance between the substrate on which the film was formed and the photomask (photomask) was set to 250 um, and the entire surface of the substrate was irradiated with an exposure amount ^{of 40 mJ / cm 2 using an exposure device.} Then, the exposed substrate was developed in a developing solution (potassium hydroxide (KOH), 0.05%) for 60 seconds, and then heat-treated (postbake) at 230 ° C. for 20 minutes to prepare a substrate.

Heat resistance evaluation

A transmittance spectrum in the visible light region in the range of 380 nm to 780 nm was obtained from the substrate produced by the method for producing the substrate using a spectroscope (MCPD-Otsuka Co., Ltd.). Further, the preheat-treated (prebake) substrate was additionally subjected to post-heat treatment (postbake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum with the same equipment and measurement range.

Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter referred to as ΔEab) was calculated using the obtained values E (L *, a *, b *) and shown in Table 1 below. ..

A small ΔEab value means that the color heat resistance is excellent.

When it has a value of ΔEab <3, it can be used as a dye for a color filter, and it can be said that it is a coloring material having excellent heat resistance. Specifically, the formula for calculating ΔEab is as follows.

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

Referring to Table 1 above, the color pattern substrate formed by using the photosensitive resin compositions of Examples 1 to 18 of the present invention has a transmittance spectrum difference (ΔEab) of less than 3 between the post-heat treatment and the post-heat treatment. Therefore, it was confirmed that the color stability was high and very little, and the heat resistance was excellent.

Measurement of light-dark ratio

Using a light-dark ratio measuring device (CT-1, ZOENTICH), the substrate produced by the method for producing the substrate is inserted between the two polarizing plates, and the two polarizing plates are horizontal. The brightness at the time and the brightness when the two polarizing plates were orthogonal to each other were measured, and the light-dark ratio was calculated by the following formula 2.

[Calculation formula 2]
Brightness / darkness ratio = brightness when two polarizing plates are horizontal / brightness when two polarizing plates are vertical

The light-dark ratio calculated by the above formula 2 is shown in Table 2 below after calculating the light-dark ratio improvement rate by the following formula 3.

[Calculation formula 3]
Light-dark ratio improvement rate = (light-dark ratio of Examples-light-dark ratio of Comparative Examples 1, 2 or 4) / light-dark ratio of Comparative Examples 1, 2 or 4 * 100)

With reference to Table 2, it was confirmed that the light-dark ratio of Examples 1 to 18 was improved by 220.47% to 532.38% as compared with Comparative Example 1. Further, it was confirmed that the light-dark ratio of Examples 1 to 18 was improved by 136.48% to 329.57% as compared with Comparative Example 2. Furthermore, it was confirmed that the light-dark ratio of Examples 1 to 18 was improved by 197.83% to 510.43% as compared with Comparative Example 4.

Measurement of fluorescence intensity

Using the FS-2 fluorescence measurement equipment manufactured by Sinco, the fluorescence intensity of the substrate produced by the method for producing the substrate was measured at room temperature (25 ° C.) with an excitation wavelength of 545 nm and an excitation wavelength of 560 nm to 720 nm. Shown in 1.

According to FIG. 1, the fluorescence intensities of Examples 6, 7 and 12 according to one embodiment of the present specification are lower than those of Comparative Examples 1 and 2 and have an excellent light-dark ratio without the addition of additional dyes. Was able to be confirmed.

Transparency evaluation

The substrate produced by the method for producing the substrate was subjected to postbake at 230 ° C. for 20 minutes using a spectroscope (MCPD-Otsuka) in the visible light region in the range of 380 nm to 780 nm. A transmittance spectrum was obtained.

In particular, in the case of a blue color filter, better brightness can be exhibited when the maximum transmittance at 380 nm to 480 nm is high in terms of visual sense x, visual sense y, and visual sense z.

FIG. 2 shows the visual sense x, the visual sense y, and the visual sense z.

With reference to Table 3, it can be seen that the maximum transmittance of Examples 1 and 7 and 13 at 380 nm to 480 nm is higher than that of Comparative Example 3.

According to FIG. 3, the transmittances of Examples 1, 7 and 13 according to one embodiment of the present specification at 380 nm to 480 nm are larger than those of Comparative Example 3 and show better brightness in the blue color filter. I was able to confirm.

Claims (14)

Compound represented by the following chemical formula 1:
[Chemical formula 1]

In the chemical formula 1,
L1 and L2 are the same or different from each other and are independently substituted or unsubstituted alkylene groups.
R1 and R2 are dianhydride groups containing nitrogen atoms, which are the same or different from each other and are independent of each other.
R3 and R4 are the same or different from each other and are independently substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups, respectively.
R5 to R12 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; -OH; -SO ₃ H; -SO ₃ M; -SO ₂ NM1 M2; -SO ₂ NHY; -COOH; substitution or From unsubstituted alkyl groups; substituted or unsubstituted cycloalkyl groups; substituted or unsubstituted alkenyl groups; substituted or unsubstituted cycloalkenyl groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heteroaryl groups Selected from the group
R13~R17, equal to or different from each other, each independently, hydrogen, deuterium, ^{_{halogen; -OH; -SO 3 -; -SO}} 3 H; -SO 3 M; -SO 2 NM1M2; -SO 2 NHY; -COOH; anionic group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.
The M is selected from the group consisting of compounds containing ^{Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ^{+; and ammonium structures.}
The M1, M2 and Y are the same or different from each other and are independently selected from the group consisting of substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; and substituted or unsubstituted heteroaryl groups.
At least one of R13 to R17 is an anionic group.
X is an anionic group,
a is 0 or 1 and
r5 and r6 are integers from 0 to 4 and
When r5 is 2 or more, R5 are the same or different from each other.
When r6 is 2 or more, R6 are the same or different from each other. The X is an anion of a compound containing at least one element and oxygen selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus; a trifluolmethanesulfonic acid anion; a bis (trifluoromethylsulfonyl) amide. Anion; Bistrifluolmethanesulfonimide Anion; Bisperfluolethylsulfonimide Anion; Tetraphenylborate Anion; Tetrakiss (4-fluorophenyl) borate; Tetrakiss (pentafluorophenyl) borate; Tristrifluoromethanesulfonylmethi D; and one selected from the group consisting of halogen groups,
The compound according to claim 1. The M is selected from the group consisting of compounds containing ^{Na +} ; K ⁺ ; Rb ⁺ ; Cs ⁺ ; Fr ^{+; and ammonium structures.}
The compound containing an ammonium structure comprises a unit represented by the following chemical formula A or a unit represented by the following chemical formula B.
The compound according to claim 1 or 2.
[Chemical formula A]

[Chemical formula B]

In the chemical formula A,
Ra to Rd are the same or different from each other, and independently of each other, 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 a hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted arylalkyl group.
The L ₁ and L ₂ are substituted or unsubstituted alkylene groups.
In the chemical formula B,
Rb to Rd are the same or different from each other and are independently hydrogen; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; or 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; a substituted or unsubstituted arylene group; -L _3- NHCO-; or -L _4- OCO-.
The L ₃ and L ₄ are substituted or unsubstituted alkylene groups.
Re to Rg are hydrogen; or substituted or unsubstituted alkyl groups, which are the same or different from each other and are independent of each other. The chemical formula 1 is represented by the following chemical formula 2.
The compound according to any one of claims 1 to 3.
[Chemical formula 2]

In the chemical formula 2,
L1, L2, R1 to R17, X, a, r5 and r6 are as defined in the above chemical formula 1. The chemical formula 1 is represented by the following chemical formula 3.
The compound according to any one of claims 1 to 3.
[Chemical formula 3]

In the chemical formula 3,
L1, L2, R1 to R17, X, a, r5 and r6 are as defined in the above chemical formula 1. The chemical formula 1 is represented by the following chemical formula 4.
The compound according to any one of claims 1 to 3.
[Chemical formula 4]

In the chemical formula 4,
L1, L2, R1 to R17, X, a, r5 and r6 are as defined in the above chemical formula 1. The dianhydride group containing a nitrogen atom is represented by any one of the following substituents.
The compound according to any one of claims 1 to 6.

In the substituent

Indicates a site linked to the above chemical formula 1.
X1, X2 and Y1 to Y3 are the same or different from each other and are independent of each other, hydrogen; heavy hydrogen; halogen group; nitro group; -OH; -SO ₃ H ;; -COOH; phosphine group; anionic group; substitution. Alternatively, an unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent groups are bonded to form a substituted or unsubstituted ring. The compound represented by the chemical formula 1 is represented by any one of the following chemical formulas.
The compound according to claim 1:

In the chemical formula
M and Y are as defined in Chemical Formula 1. The compound according to any one of claims 1 to 8.
Binder resin;
Polyfunctional monomer;
Photosensitivity resin composition comprising a photoinitiator; and a solvent. Based on the total weight of the solid content in the photosensitive resin composition,
The content of the compound represented by the chemical 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% by weight to 20% by weight.
The content of the polyfunctional monomer is 0.1% by weight to 50% by weight.
The photosensitive resin composition according to claim 9. Including additional additives,
The photosensitive resin composition according to claim 9 or 10. A photosensitive material produced by using the photosensitive resin composition according to any one of claims 9 to 11. A color filter containing the photosensitive material according to claim 12. A display device including the color filter according to claim 13.

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