JP2020512429A - Xanthene compound, coloring material composition, photosensitive resin composition, photosensitive material, color filter and display device - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1, a coloring material composition containing the same, a photosensitive resin composition, a photosensitive material, a color filter, and a display device.

Description

  This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0022076 filed with the Korean Patent Office on February 23, 2018, the entire contents of which are incorporated herein.

  This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0001820 filed with the Korean Patent Office on January 7, 2019, the entire contents of which are incorporated herein.

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

  Recently, a color filter is required to have a performance characterized by high brightness and high contrast ratio. Further, one of the main purposes of developing a display element is to differentiate display element performance by improving color purity and improve productivity in a manufacturing process.

  Conventionally, since the pigment type used as a color material of a color filter exists in a color photoresist in a particle dispersed state, it has been difficult to adjust the brightness and contrast ratio by adjusting the size and distribution of the pigment particles. In the case of pigment particles, aggregation and dissolution and dispersibility of pigment particles are reduced, and large particles that are aggregated cause multiple scattering of light. Such scattering of polarized light is considered to be the main cause of lowering the contrast ratio. Although efforts are being made to improve the brightness and the contrast ratio by stabilizing the ultrafine particles and stabilizing the dispersion of the pigment, the degree of freedom is limited in the selection of the color material for realizing the color coordinates for the high color purity display device. In addition, the already developed color material, especially the pigment dispersion method using a pigment, has reached the limit to improve the color purity, brightness and contrast ratio of the color filter using the color material.

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

  The present inventors intend to provide a xanthene-based compound, a color material composition containing the same, a photosensitive resin composition, a photosensitive material manufactured using the same, a color filter, and a display device including the same.

前記化学式１において、
Ｒ_１〜Ｒ_６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；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数１〜３０のアルコキシ基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；および置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基からなる群より選択され、
Ｒ_７〜Ｒ_１１は、互いに同一または異なり、それぞれ独立に、水素；重水素；−ＯＨ；−ＳＯ_３ ⁻；−ＳＯ_３Ｈ；−ＳＯ_３Ｒａ；−ＳＯ_２ＮＲｂＲｃ；−ＳＯ_２ＮＨＲｄ；−ＣＯＯＨ；−ＣＯＯＲａ；−ＣＯＮＨＲｄ；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；および置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基からなる群より選択され、
Ｒａ〜Ｒｄは、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；および置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基からなる群より選択され、
Ｒ_１２は、水素；重水素；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基；および窒素原子を含む二無水物基からなる群より選択され、
Ｒ_１３およびＲ_１４は、それぞれ独立に、置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基であり、
Ｒ_１５およびＲ_１６は、互いに同一または異なり、それぞれ独立に、水素；重水素；−ＯＨ；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；および置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基からなる群より選択されるか、互いに結合して置換もしくは非置換の炭素数６〜３０の単環もしくは多環の芳香族炭化水素環；または置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロ環を形成し、
Ｌ_１およびＬ_２は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換の炭素数２〜３０の直鎖もしくは分枝鎖のアルキレン基；−Ｌ_３−Ｏ−Ｌ_４−；−Ｌ_３−Ｓ−Ｌ_４−；−Ｌ_３−ＮＨ−Ｌ_４−；−Ｌ_３−ＣＯ−Ｌ_４−；−Ｌ_３−ＣＯＯ−Ｌ_４−；−Ｌ_３−ＯＣＯ−Ｌ_４−；−Ｌ_３−ＮＨＣＯ−Ｌ_４−；および−Ｌ_３−ＣＯＮＨ−Ｌ_４−からなる群より選択され、
Ｌ_３およびＬ_４は、互いに同一または異なり、置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキレン基であり、
ａは、０または１の整数であり、
Ｘは、陰イオン性基である。 One embodiment of the present specification provides a compound represented by Chemical Formula 1 below.
[Chemical formula 1]

In Chemical Formula 1,
R _{1 to} R ₆ are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a nitro group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; An unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic group having 2 to 30 carbon atoms Selected from the group consisting of heteroaryl groups,
R ₇ to R _11, equal to or different from each other, each independently, hydrogen, ^{_{deuterium; -OH; -SO 3 -; -SO}} 3 H; -SO 3 Ra; -SO 2 NRbRc; -SO 2 NHRd; - COOH; -COORa; -CONHRd; substituted or unsubstituted C1-C30 linear or branched alkyl group; substituted or unsubstituted C6-C30 monocyclic or polycyclic aryl group; and Selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
Ra to Rd are the same or different from each other, and each independently, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 6 to 30 carbon atoms. A cyclic aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
R ₁₂ is hydrogen; deuterium; a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted, monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; and a dianhydride group containing a nitrogen atom,
R ₁₃ and R ₁₄ are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
R ₁₅ and R ₁₆ are the same or different from each other, and each independently, hydrogen; deuterium; -OH; a substituted or unsubstituted C 1 to C 30 straight or branched chain alkyl group; a substituted or unsubstituted A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or substituted by bonding to each other. Or an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms,
L ₁ and _{L 2,} equal to or different from each other, each independently, a direct bond; an alkylene group having a linear or branched substituted or unsubstituted _{C2-30; -L 3 -O-L 4 -} ; _{-L 3 -S-L 4 -;} - L 3 -NH-L 4 -; - L 3 -CO-L 4 -; - L 3 -COO-L 4 -; - L 3 -OCO-L 4 -; -L _{3 -NHCO-L 4} -; and _-L 3 _{-CONH-L 4} - is selected from the group consisting of,
L ₃ and L ₄ are the same or different from each other, and are a substituted or unsubstituted C _{1 to} C 30 linear or branched alkylene group,
a is an integer of 0 or 1,
X is an anionic group.

  One embodiment of the present specification provides a coloring material composition including the compound represented by Chemical Formula 1.

  One embodiment of the present specification provides a photosensitive resin composition including a compound represented by the above Chemical Formula 1, a binder resin, a polyfunctional monomer, a 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 including the photosensitive material.

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

  The xanthene-based compound according to one embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, and, as compared with conventional coloring materials, the spectrum emitted from a light source and the absorption and transmission spectra of a color filter are harmonized. With this, color purity can be increased.

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

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

  In this specification, when a portion is “comprising” a component, this means that other components can be included rather than excluding other components unless specifically stated to the contrary. To do.

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

  In the above Chemical Formula 1, when the alkyl phthalimide is substituted for the nitrogen atom, the dispersibility of the pigment can be enhanced, and the crystal transition of the pigment can be suppressed at high temperature to stabilize the pigment at high temperature. As a result, it is possible to improve the dispersibility and storage stability and reduce color change by stabilizing the pigment.

When R ₁₃ and R ₁₄ are alkyl groups, the photosensitive material containing the compound of Formula 1 has a maximum absorption wavelength (λmax) in the range of 550 to 580 nm and has excellent transmittance at 600 nm or more and has a red wavelength. There is an advantage that it is easy to realize the color of the area.

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

In the present specification, the term "substituted or unsubstituted" means deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; silyl group; aryl group; alkylsulfoxy group; arylsulfoxy group. ; boron group; alkylamine group; arylamine group; a heteroaryl group, an ether group, a nitrile group, a nitro group, hydroxy group (-OH); a carboxyl group (-COOH); - ^{SO 3-;} sulfonic acid; sulfonic acid Ester group; sulfonate group; substituted with one or more substituents selected from the group including a heterocyclic group containing at least one of N, O, S, or P atoms and an anionic group , Or means that it does not have any substituents.

  In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but one having 1 to 30 is preferable. Specifically, it may be 1 to 20, or 1 to 10. Specific examples include, but are not limited to, methyl group, ethyl group, propyl group, isopropyl group, butyl group, t-butyl group, pentyl group, hexyl group, and heptyl group.

  In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specifically, it may be 2 to 20, or 2 to 10. As a specific example, an alkenyl group substituted with an aryl group such as a stilbenyl group (stylbenyl) and a styrenyl group (styrenyl) is preferable, but not limited thereto.

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

  In the present specification, the cycloalkyl group is not particularly limited, but those having 3 to 30 carbon atoms are preferable, and cyclopentyl group and cyclohexyl group are particularly preferable. Specifically, it may be 3 to 20, or 3 to 10.

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

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

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

  In the present specification, specific examples of the sulfonate group include, but are not limited to, alkylsulfonyl having 1 to 4 carbon atoms such as methanesulfonyl, ethanesulfonyl and hexanesulfonyl.

In the present specification, the sulfonamide group may be represented as —SO ₂ NRxRy, for example, Rx and Ry are the same or different from each other, and each independently have a substituted or unsubstituted carbon number of 1 to 30. A straight chain or branched chain alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic hetero group having 2 to 30 carbon atoms It is an aryl group.

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

  When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but one having 6 to 30 carbon atoms is preferable. Specifically, it may have 6 to 20 carbon atoms or 6 to 12 carbon atoms. For example, the monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group and the like.

  When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but one having 10 to 30 carbon atoms is preferable. Specifically, the polycyclic aryl group may be, but is not limited to, a naphthyl group, anthryl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like.

  In the present specification, the heterocyclic group is a heterocyclic group containing O, N, or S as a heteroatom, and the carbon number is not particularly limited, but the one having 2 to 30 carbon atoms is preferable. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, triazine group, acridyl group, pyridazine group, quinolinyl group. Group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, dibenzofuran group, but not limited to these. Not something.

  In the present specification, the description of the heterocyclic group described above is applicable, except that the heteroaryl group is aromatic. The carbon number of the heteroaryl group is not particularly limited, but may be 2 to 30. Specifically, it may be 2 to 20, or 2 to 10 in another embodiment.

  In the present specification, an alkylene group means one having two bonding positions in an alkane. The alkylene group may be linear, branched or cyclic. The carbon number of the alkylene group is not particularly limited, but is, for example, 1 to 30 carbon atoms. Specifically, it may have 1 to 20 carbon atoms, and in yet another embodiment, it may have 1 to 10 carbon atoms.

  In the present specification, an alkenylene group means an alkene having two bonding positions. The alkenylene group may be linear, branched or cyclic. The carbon number of the alkenylene group is not particularly limited, but it is, for example, 2 to 30 carbon atoms. Specifically, it may be 2 to 20, or more specifically, 2 to 10.

In the present specification, the anionic group has a chemical bond with the structure of Chemical Formula 1, and the anionic group is not particularly limited. For example, US Pat. No. 7,939,644, Japanese Patent Open 2006-003080, Japanese Unexamined Patent Publication No. 2006-001917, Japanese Unexamined Patent Publication No. 2005-159926, Japanese Unexamined Patent Publication No. 2007-7028897, Japanese Unexamined Patent Publication No. 2005-071680, Korean application publication. The anions described in JP-A-2007-7000693, JP-A-2005-111696, JP-A-2008-249663 and JP-A-2014-199436 are applicable. Specific examples of the anionic group include anions of compounds containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus; trifluoromethanesulfonate anion, bis. (Trifluoromethylsulfonyl) amide anion, bistrifluoromethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrakis (4-fluorophenyl) borate, tetrakis (pentafluorophenyl) borate, tris trifluoromethanesulfonyl ^{_{methide, -SO 3 -, -CO 2 -}} , -SO 2 N - SO 2 CF 3, -SO 2 N - SO 2 CF 2 CF 3, halogen, such as fluorine group, iodine There are groups, chlorine groups, etc. Not intended to be only limited.

  As used herein, anionic groups may have anions themselves or may be present in the form of complex compounds with other cations. Therefore, the total charge of the entire compound molecule of the present invention can be changed depending on the number of substituted anionic groups. Since the compound of the present invention has a cation in one amine group, the total charge of the entire molecule is from the number of the substituted anionic groups minus one, from anion to zero. Can have the value of

According to the above-described embodiment, in the Chemical Formula 1, R _{1 to} R ₆ are the same or different from each other and each independently represent hydrogen; deuterium; a halogen group; a nitro group; a substituted or unsubstituted carbon number 1 to 30 straight-chain or branched-chain alkyl group; substituted or unsubstituted C1-C30 alkoxy group; substituted or unsubstituted C6-C30 monocyclic or polycyclic aryl group; and substituted or non-substituted It may be selected from the group consisting of substituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.

According to another embodiment of the present specification, R _{1 to} R ₆ are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a nitro group; 20 straight-chain or branched-chain alkyl group; substituted or unsubstituted C 1-20 alkoxy group; substituted or unsubstituted C 6-20 monocyclic or polycyclic aryl group; and substituted or non-substituted It may be selected from the group consisting of substituted C2-C20 monocyclic or polycyclic heteroaryl groups.

According to another embodiment of the present specification, R _{1 to} R ₆ are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a nitro group; A linear or branched alkyl group having 10; a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms; and substituted or non-substituted It may be selected from the group consisting of substituted monocyclic or polycyclic heteroaryl groups having 2 to 10 carbon atoms.

According to another embodiment of the present specification, R _{1 to} R ₆ are the same or different from each other and each independently represent hydrogen; a halogen group; or a substituted or unsubstituted straight chain having 1 to 10 carbon atoms or It may be a branched chain alkyl group.

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

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

According to another embodiment of the present specification, R _{1 to} R ₆ may be the same or different from each other, each independently being hydrogen; fluorine; or a methyl group.

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

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

According to another embodiment of the present specification, R ₁ and R ₄ are fluorine; or a methyl group, and R ₂ , R ₃ , R ₅ , or R ₆ may be hydrogen.

_Further, R 7 _{to R 11,} equal to or different from each other, each independently, hydrogen, ^{_{deuterium; -OH; -SO 3 -; -SO}} 3 H; -SO 3 Ra; -SO 2 NRbRc; -SO 2 NHRd -COOH; -COORa; -CONHRd; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
Ra to Rd are the same or different from each other, and each independently, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 6 to 30 carbon atoms. A cyclic aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to another embodiment of the present specification, R _{7 to} R ₁₁ are the same or different from each other and each independently represent hydrogen; deuterium; —OH; —SO ₃ ^— ; —SO ₃ H; _{3 Ra; -SO 2 NRbRc; -SO} 2 NHRd; -COOH; -COORa; -CONHRd; substituted or unsubstituted carbon atoms, alkyl group of straight or branched chain substituted or unsubstituted C 1-20 6 to 20 monocyclic or polycyclic aryl group; and a substituted or unsubstituted C2 to C20 monocyclic or polycyclic heteroaryl group,
Ra to Rd are the same or different from each other, and each independently, a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic alkyl group having 6 to 20 carbon atoms. A cyclic aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.

According to another embodiment of the present specification, R _{7 to} R ₁₁ are the same or different from each other and each independently represent hydrogen; deuterium; —OH; —SO ₃ ^— ; —SO ₃ H; _{3 Ra; -SO 2 NRbRc; -SO} 2 NHRd; -COOH; -COORa; -CONHRd; alkyl substituted or unsubstituted straight or branched chain having 1 to 10 carbon atoms; a substituted or unsubstituted carbon atoms A monocyclic or polycyclic aryl group having 6 to 12; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms,
Ra to Rd are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic alkyl group having 6 to 12 carbon atoms. A cyclic aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms.

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

According to one embodiment of the present specification, R _{7 to} R ₁₁ are the same or different from each other, and each independently, may be hydrogen; —SO ₃ ⁻ ; —SO ₃ H; or —SO ₂ NHRd. Rd may be a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted pentyl group; a substituted or unsubstituted hexyl group; or a substituted or unsubstituted heptyl group. Good.

According to one embodiment of the present specification, R _{7 to} R ₁₁ are the same or different from each other, and each independently, may be hydrogen; —SO ₃ ⁻ ; —SO ₃ H; or —SO ₂ NHRd. However, Rd may be a substituted or unsubstituted propyl group; or a substituted or unsubstituted hexyl group.

According to one embodiment of the present specification, R _{7 to} R ₁₁ are the same or different from each other, and each independently, may be hydrogen; —SO ₃ ⁻ ; —SO ₃ H; or —SO ₂ NHRd. However, Rd may be a hexyl group substituted with an ethyl group; or a propyl group substituted or unsubstituted with an ethyl group.

R ₁₂ is hydrogen; deuterium; a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted, monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. A group; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; and a dianhydride group containing a nitrogen atom.

According to another embodiment of the present specification, R ₁₂ is hydrogen; deuterium; substituted or unsubstituted C1-C20 straight chain or branched chain alkyl group; substituted or unsubstituted carbon number 6 to 20 monocyclic or polycyclic aryl groups; substituted or unsubstituted C2 to C20 monocyclic or polycyclic heteroaryl groups; and a dianhydride group containing a nitrogen atom, Good.

According to another embodiment of the present specification, R ₁₂ is hydrogen; deuterium; substituted or unsubstituted C 1-10 linear or branched alkyl group; substituted or unsubstituted carbon number A monocyclic or polycyclic aryl group having 6 to 12; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms; and a dianhydride group containing a nitrogen atom. Good.

According to another embodiment of the present specification, R ₁₂ is a substituted or unsubstituted C 1-10 linear or branched alkyl group; or a dianhydride group containing a nitrogen atom, Good.

According to another embodiment of the present specification, R ₁₂ is a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted isopropyl group; a substituted Alternatively, it may be an unsubstituted isobutyl group; or a dianhydride group containing a nitrogen atom.

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

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

When R ₁₃ and R ₁₄ are the same or different from each other and each independently have a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms, they can emit light in the red wavelength region. Therefore, when a color filter is manufactured using a photosensitive material including the compound represented by the structure of Chemical Formula 1, a desired color can be selectively realized.

Specifically, when R ₁₃ and R ₁₄ are alkyl groups, the maximum absorption wavelength (λmax) of the photosensitive material containing the compound of Chemical Formula 1 exists in the range of 550 to 580 nm, and the transmittance at 600 nm or more is excellent. It is easy to realize colors in the red wavelength range.

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

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

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

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

R ₁₅ and R ₁₆ are the same or different from each other, and each independently, hydrogen; deuterium; —OH; a substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or bonded to each other. To form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms. .

According to another embodiment of the present specification, R ₁₅ and R ₁₆ are the same or different from each other and each independently represent hydrogen; deuterium; —OH; a substituted or unsubstituted straight chain having 1 to 20 carbon atoms. Or a branched chain alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms or a substituted or unsubstituted monocyclic ring having 2 to 20 carbon atoms selected from the group consisting of A polycyclic hetero ring may be formed.

According to another embodiment of the present specification, R ₁₅ and R ₁₆ are the same or different from each other, and each independently, hydrogen; deuterium; —OH; a substituted or unsubstituted straight chain having 1 to 10 carbon atoms. Or a branched chain alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 12 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms, or a substituted or unsubstituted monocyclic ring having 2 to 10 carbon atoms selected from the group consisting of A polycyclic hetero ring may be formed.

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

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

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

In addition, L ₁ and L ₂ are the same or different from each other, and each independently, a substituted or unsubstituted alkylene group having 2 to 30 carbon atoms or a branched chain; -L ₃ -O-L ₄ -;- _{L 3 -S-L 4 -;} - L 3 -NH-L 4 -; - L 3 -CO-L 4 -; - L 3 -COO-L 4 -; - L 3 -OCO-L 4 -; - L ₃ —NHCO-L ₄ —; and —L ₃ —CONH-L ₄ —,
L ₃ and L ₄ may be the same or different from each other, and may be a substituted or unsubstituted linear or branched alkylene group having 1 to 30 carbon atoms.

Wherein _{L 1} and _{L 2} equal to or different from each other, each _{independently, -L 3 -O-L 4 -} ; - L 3 -S-L 4 -; - L 3 -NH-L 4 -; - L 3 - _{CO-L 4 -; - L} 3 -COO-L 4 -; - L 3 -OCO-L 4 -; - L 3 -NHCO-L 4 -; or _-L 3 _{-CONH-L 4} - a and, L ₃ and L ₄ are the same or different from each other, and are a substituted or unsubstituted straight-chain or branched alkylene group having 1 to 30 carbon atoms, and L ₁ and L ₂ are the same or different from each other, and are independent of each other. In addition, in the case of a substituted or non-substituted linear or branched alkylene group having 2 to 30 carbon atoms, the same or similar effect can be obtained.

This is the _{L 1} and _{L 2 -L 3 -O-L 4 -;} - L 3 -S-L 4 -; - L 3 -NH-L 4 -; - L 3 -CO-L 4 -; _{-L 3 -COO-L 4 -;} - L 3 -OCO-L 4 -; - L 3 -NHCO-L 4 -; or _-L 3 _{-CONH-L 4} - in the case of a substituted or unsubstituted carbon This is because it contains L ₃ and L ₄ , which are linear or branched alkylene groups of the numbers 1 to 30.

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other, and are each independently a substituted or unsubstituted C ₂ to C 20 linear or branched alkylene group; -L _{3- O-L 4 -; - L} 3 -S-L 4 -; - L 3 -NH-L 4 -; - L 3 -CO-L 4 -; - L 3 -COO-L 4 -; - L 3 - _{OCO-L 4 -; - L} 3 -NHCO-L 4 -; and _-L 3 _{-CONH-L 4} - is selected from the group consisting of,
L ₃ and L ₄ may be the same or different from each other, and may be a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, which is linear or branched.

In one embodiment of the present specification, L ₁ and L _2, equal to or different from each other, each independently, an alkylene group having a linear or branched substituted or unsubstituted C2-10; -L ₃ - _{O-L 4 -; - L} 3 -S-L 4 -; - L 3 -NH-L 4 -; - L 3 -CO-L 4 -; - L 3 -COO-L 4 -; - L 3 - _{OCO-L 4 -; - L} 3 -NHCO-L 4 -; and _-L 3 _{-CONH-L 4} - is selected from the group consisting of,
L ₃ and L ₄ may be the same or different from each other, and may be a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms which is linear or branched.

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other, and each independently, may be a substituted or unsubstituted C 2-10 straight-chain or branched-chain alkylene group. .

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

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other, and each independently, may be an ethylene group; or a propylene group.

  In one embodiment of the present specification, a is an integer of 0 or 1.

  In another embodiment herein, a is 0.

  In another embodiment herein, a is 1.

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

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

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

前記構造において、Ｒ_１〜Ｒ_１６、Ｌ_１、Ｌ_２、ａおよびＸは、前記化学式１で定義した通りである。 In one embodiment of the present specification, Formula 1 may be represented by the following structure, and the structure below represents an isomer of Formula 1, and Formula 1 represents a representative structure. . Isomers mean molecules having the same molecular formula but different physical / chemical properties.

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

前記化学式２において、
Ｒ_１〜Ｒ_１１、Ｒ_１３〜Ｒ_１６、Ｌ_１、Ｌ_２、ａおよびＸは、前記化学式１で定義した通りであり、
Ｒ_１７およびＲ_１８は、互いに同一または異なり、それぞれ独立に、水素；重水素；ヒドロキシ基；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；および置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基を含む群より選択されるか、互いに結合して置換もしくは非置換の炭素数６〜３０の単環もしくは多環の芳香族炭化水素環；または置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロ環を形成する。 According to another embodiment of the present specification, Formula 1 is represented by Formula 2 below.
[Chemical formula 2]

In the chemical formula 2,
R _{1 to} R ₁₁ , R _{13 to} R ₁₆ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1,
R ₁₇ and R ₁₈ are the same or different from each other, and each independently, hydrogen; deuterium; a hydroxy group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or substituted by bonding to each other Alternatively, it forms an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R ₁₇ and R ₁₈ are the same or different from each other, and each independently, hydrogen; deuterium; a hydroxy group; a substituted or unsubstituted straight or branched chain having 1 to 20 carbon atoms. An alkyl group; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms. Or a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 20 carbon atoms. Form a ring.

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

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

According to another embodiment herein, R ₁₇ and R ₁₈ may combine with each other to form a substituted or unsubstituted benzene ring.

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

前記化学式３において、
Ｒ_１〜Ｒ_１４、Ｌ_１、Ｌ_２、ａおよびＸは、前記化学式１で定義した通りであり、
Ｒ_１９は、水素；重水素；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数１〜３０のアルコキシ基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基；ハロゲン基；ニトロ基；−ＣＯＯＨ；−ＯＨ；スルホン酸基；スルホン酸エステル基；スルホン酸塩基；−ＳＯ_２ＮＲｂＲｃ；および−ＳＯ_２ＮＨＲｄからなる群より選択され、
Ｒｂ〜Ｒｄは、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基であり、
ｍは、１〜４の整数であり、ｍが２以上の場合、Ｒ_１９は、互いに同一または異なる。 In addition, according to another embodiment of the present specification, Formula 1 is represented by Formula 3 below.
[Chemical formula 3]

In Chemical Formula 3,
R _{1 to} R ₁₄ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1,
R ₁₉ is hydrogen; deuterium; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted carbon A monocyclic or polycyclic aryl group of 6 to 30; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group of 2 to 30 carbon atoms; a halogen group; a nitro group; -COOH; -OH; a sulfonic acid group ; sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
m is an integer of 1 to 4, and when m is 2 or more, R _19's are the same or different from each other.

In another embodiment of the present specification, R ₁₉ is hydrogen; deuterium; a substituted or unsubstituted C 1 to C 20 straight or branched chain alkyl group; a substituted or unsubstituted C 1 to C 1 20 alkoxy group; substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; halogen group; nitro group; -COOH; -OH; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd are the same or different and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms,
m is an integer of 1 to 4, and when m is 2 or more, R _19's are the same or different from each other.

In another embodiment of the present specification, R ₁₉ is hydrogen; deuterium; a substituted or unsubstituted C1-C10 straight chain or branched chain alkyl group; a substituted or unsubstituted C1-C1 10 alkoxy group; substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 12 carbon atoms; substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 10 carbon atoms; halogen group; nitro group; -COOH; -OH; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd are the same or different and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms,
m is an integer of 1 to 4, and when m is 2 or more, R _19's are the same or different from each other.

According to another embodiment of the present specification, R ₁₉ is hydrogen; or a substituted or unsubstituted C 1-10 linear or branched alkyl group.

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

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

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

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

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

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

前記化学式４において、
Ｒ_１〜Ｒ_１１、Ｒ_１３、Ｒ_１４、Ｌ_１、Ｌ_２、ａおよびＸは、前記化学式１で定義した通りであり、
Ｒ_１９およびＲ_２０は、互いに同一または異なり、それぞれ独立に、水素；重水素；置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基；置換もしくは非置換の炭素数１〜３０のアルコキシ基；置換もしくは非置換の炭素数６〜３０の単環もしくは多環のアリール基；置換もしくは非置換の炭素数２〜３０の単環もしくは多環のヘテロアリール基；ハロゲン基；ニトロ基；−ＣＯＯＨ；−ＯＨ；スルホン酸基；スルホン酸エステル基；スルホン酸塩基；−ＳＯ_２ＮＲｂＲｃ；および−ＳＯ_２ＮＨＲｄからなる群より選択され、
Ｒｂ〜Ｒｄは、互いに同一または異なり、それぞれ独立に、置換もしくは非置換の炭素数１〜３０の直鎖もしくは分枝鎖のアルキル基であり、
ｍは、１〜４の整数であり、
ｎは、１〜４の整数であり、
ｍが２以上の場合、Ｒ_１９は、互いに同一または異なり、
ｎが２以上の場合、Ｒ_２０は、互いに同一または異なる。 In addition, according to another embodiment of the present specification, Formula 1 is represented by Formula 4 below.
[Chemical formula 4]

In Chemical Formula 4,
R _{1 to} R ₁₁ , R ₁₃ , R ₁₄ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1,
R ₁₉ and R ₂₀ are the same or different from each other, and independently of each other, hydrogen; deuterium; a substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; a substituted or unsubstituted C 1 An alkoxy group having 30 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; a halogen group; a nitro group; -COOH; -OH; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
m is an integer of 1 to 4,
n is an integer of 1 to 4,
When m is 2 or more, R _19's are the same or different from each other,
When n is 2 or more, R _20's are the same or different from each other.

In one embodiment of the present specification, R ₁₉ and R ₂₀ are the same or different from each other, and independently, hydrogen; deuterium; a substituted or unsubstituted C 1-20 linear or branched alkyl group. A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 2 to 20 carbon atoms heteroaryl group ring; a halogen group; a nitro group; -COOH; -OH; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd may be the same or different from each other, and each independently, may be a substituted or unsubstituted linear or branched alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R ₁₉ and R ₂₀ are the same or different from each other, and independently, hydrogen; deuterium; a substituted or unsubstituted C 1-10 linear or branched alkyl group. A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 12 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 2 to 10 carbon atoms heteroaryl group ring; a halogen group; a nitro group; -COOH; -OH; a sulfonic acid group; a sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd may be the same as or different from each other, and each independently, may be a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms.

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

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

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

前記化学式中、Ｘは、前記化学式１で定義した通りである。 The compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas, but is not necessarily limited thereto.

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

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

  When the compound according to the present specification satisfies the maximum absorption wavelength in the above range, the color coordinates can be realized with a smaller amount when the red color filter is applied.

The maximum absorption wavelength can be measured by dissolving the compound in propylene glycol monomethyl ether acetate (PGMEA) at a concentration of 10 ⁻⁵ mol at 25 ° C. and using a UV-visible spectrometer (SCINCO).

  Further, one embodiment of the present specification provides a coloring material composition containing the compound.

  Furthermore, according to one embodiment of the present specification, the coloring material composition may further include at least one of a dye and a pigment.

  For example, the coloring material composition may include only the compound of Chemical Formula 1, but may include the compound of Chemical Formula 1 and one or more dyes, or the compound of Chemical Formula 1 and one or more pigments. Or may include the compound of Formula 1, the one or more dyes, and the one or more pigments.

  The dyes and pigments include metal-complex compounds; azo compounds; metal azo compounds; quinophthalone compounds; isoindoline compounds; methine. (Methine) type compound; Phthalocyanine type compound; Metal phthalocyanine type compound; Porphyrin type compound; Metal porphyrin type compound; Tetraazaporphyrin metal Tetraazaporphyrin compounds; Cyanine compounds; Xanthene compounds; metal dipyrromethene compounds; boron dipyrromethene compounds; anthraquinone compounds; anthraquinone compounds; One or more compounds may be selected from the group consisting of triarylmethane-based compounds; and perylene-based compounds.

  According to an embodiment of the present specification, the pigment further included in addition to the compound of Chemical Formula 1 may be, for example, R254 (Pigment Red 254), but is not limited thereto. The R254 is in a Millbase state and may be a commercially available product. The mill base means a state in which an insoluble coloring material is well dispersed in the composition by adding a dispersant and a binder.

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

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

  The photosensitive resin composition may further include the pigment.

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

  The binder resin may be a copolymer resin of a polyfunctional monomer that imparts mechanical strength to the film and a monomer that imparts alkali solubility, and may further include a binder generally used in the art. Good.

  The polyfunctional monomer that imparts mechanical strength to the film is at least one of unsaturated carboxylic acid esters; aromatic vinyls; unsaturated ethers; unsaturated imides; and acid anhydrides. It 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, 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- Droxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytri Propylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxy polyethylene glycol (meth) acrylate, p-nonylphenoxy polypropylene glycol (meth) acrylate, glycidyl ( (Meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafluor Isopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl It may be selected from the group consisting of acrylate and butyl α-hydroxymethyl acrylate, 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 thereto.

  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. However, the present invention is not limited to these.

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

  The alkali-solubility-imparting monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, and 5-norbornene-2-. 1 selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethyl phthalate, mono-2-((meth) acryloyloxy) ethyl succinate, and ω-carboxypolycaprolactone mono (meth) acrylate. It is preferable to use one or more types, but the present invention is not limited thereto.

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

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

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

  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 Erythritol tetramethacrylate, and dipentaerythritol May be one or a mixture of two or more selected from the group consisting of hexamethylene methacrylate.

  In an embodiment of the present specification, the polyfunctional monomer may be dipentaerythritol hexaacrylate.

  The photoinitiator is not particularly limited as long as it is an initiator that promotes crosslinking by generating radicals by light, for example, selected from the group consisting of acetophenone compounds, biimidazole compounds, triazine compounds, and oxime compounds. One or more types may be used.

  The acetophenone-based compound may be 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-propan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2- ( 4-Bromo-benzyl-2-dimethylamino-1 (4-morpholinophenyl) - butan-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholino-1-one include, but are not limited to.

  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' -Tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like, but not limited thereto.

  The triazine-based compound is 3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 1,1,1,3,3,3-hexafluoroisopropyl. -3- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionate, ethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazine -6-yl] phenylthio} acetate, 2-epoxyethyl-2- {4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, cyclohexyl-2- {4- [ 2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} acetate, benzyl-2- {4- [2,4-bis (trichloromethyl) ) -S-Triazin-6-yl] phenylthio} acetate, 3- {chloro-4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio} propionic acid, 3- {4- [2,4-bis (trichloromethyl) -s-triazin-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, etc. , But not limited to these.

  Examples of the oxime compound include 1,2-octadione, -1- (4-phenylthio) phenyl, -2- (o-benzoyloxime) (Ciba Geigy, CGI124), ethanone, -1- (9-ethyl) -6. -(2-methylbenzoyl-3-yl)-, 1- (O-acetyloxime) (CGI242), N-1919 (Adeka) and the like, but not limited thereto.

  In one embodiment herein, the photoinitiator may be PBG-3057.

  The solvent is acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether. , Diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethene, hexane, heptane, octane, cyclohexane, Benzene, toluene, xylene, methanol, ethanol, isopropanol Propanol, butanol, t-butanol, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3- It may be one or more selected from the group consisting of ethoxy propionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether, but is not limited thereto. Not a thing.

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

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

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

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

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

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

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

  The photosensitive resin composition may further include the pigment; the leveling agent; and the adhesion aid.

  In one embodiment of the present specification, the content of the compound represented by Chemical Formula 1 is 5 wt% to 60 wt% and the content of the pigment is based on the total weight of the photosensitive resin composition. 5% to 40% by weight, the content of the binder resin is 1% to 60% by weight, the content of the photoinitiator is 0.1% to 20% by weight, and the polyfunctional monomer is Content of 0.1 wt% to 50 wt%, content of the solvent is 10 wt% to 80 wt%, content of the additive is 0.1 wt% to 20 wt%. May be.

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

  The photocrosslinking sensitizer is benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3,4. Benzophenone-based compounds such as 3-dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9 -Fluorenone compounds such as fluorenone; thioxanthone compounds such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone and diisopropylthioxanthone; Xanthone compounds such as montone and 2-methylxanthone; anthraquinone compounds such as anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, t-butylanthraquinone, 2,6-dichloro-9,10-anthraquinone; 9-phenylacridine Acridine compounds such as 1,7-bis (9-acridinyl) heptane, 1,5-bis (9-acridinylpentane), and 1,3-bis (9-acridinyl) propane; benzyl, 1,7, Dicarbonyl compounds such as 7-trimethyl-bicyclo [2,2,1] heptane-2,3-dione and 9,10-phenanthrenequinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6- Dimethoxybenzoyl) -2,4,4-trimethylpentylpho Phosphine oxide compounds such as fin oxide; benzoate compounds such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate; 2 , 5-bis (4-diethylaminobenzal) cyclopentanone, 2,6-bis (4-diethylaminobenzal) cyclohexanone, 2,6-bis (4-diethylaminobenzal) -4-methyl-cyclopentanone, etc. 3,3-carbonylvinyl-7- (diethylamino) coumarin, 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 3-benzoyl-7- (diethylamino) coumarin, 3-benzoyl-7. -Methoxy-coumarin, 10,10-carbonyl Such as rubis [1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H-C1] -benzopyrano [6,7,8-ij] -quinolidin-11-one. One or more selected from the group consisting of coumarin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzalacetophenone; 2-benzoylmethylene, 3-methyl-b-naphthothiazoline; .

  The curing accelerator is used to enhance curing and mechanical strength, and specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2). -Mercaptoacetate), pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate). It is possible to use one or more selected.

  Examples of the adhesion promoter used in the present specification include methacryloyloxy coupling agents such as methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, and methacryloyloxypropyldimethoxysilane. 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, and 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 or the like can be used, and as the fluorine-based surfactant, IC (Dai Nippon Ink & Chemicals) F-114, F-177, F-410, F-411, F-450, F-493, F-494, F-443, F-444, F-445, F-446. , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F. -486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF-1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF. , TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc. can be used. However, the present invention is not limited to these.

  The antioxidant is one or more selected from the group consisting of hindered phenolic antioxidants, amine antioxidants, thiol antioxidants, and phosphine antioxidants. However, the present invention is not limited to this.

  Specific examples of the antioxidant include phosphoric acid-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-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4 -Methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol) Nol), 4,4′-thiobis (3-methyl-6-t-butylphenol), or bis [3,3-bis- (4′-hydroxy-3′-tert-butylphenyl) butanoic acid] glycol ester ( Hindered phenol-based primary antioxidants such as Bis [3,3-bis- (4'-hydroxy-3'-tert-butylphenyl) butanoicacid] glycol ester; phenyl-α-naphthylamine, phenyl Amine secondary antioxidants such as -β-naphthylamine, N, N'-diphenyl-p-phenylenediamine, or N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl Thiopropionate, distearyl thiopropionate, Thio type secondary antioxidants such as captobenzothiazole or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite Phyto, bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Pentaerythritol Diphosphite, or tetrakis [1,1'-biphenyl) -4,4'-diylbisphosphonate [] 2,4-bis (1,1-dimethylethyl) phenyl] ester ((1,1′-Biphenyl) -4,4′-Diylbisphosphonous acid tetrakis [2, -bis (1,1-dimethylethyl) phenyl] ester phosphite secondary antioxidant such as) and the like.

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

  Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxyamine 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). -Butylphenol), 2-mercaptoimidazole, and phenothiazine, but is not limited thereto and is generally known in the art. It can include those are.

  The dispersant can be used by a method of internally adding to the pigment in the form of surface-treating the pigment in advance or an external method of adding to the pigment. As the dispersant, a compound type, nonionic, anionic, or cationic dispersant can be used. Fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, amphoteric interfaces Activator etc. are mentioned. These may be used alone or in combination of two or more.

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

  The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamidoamine, and reaction products of amine and epoxide. Specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing compounds. And any non-polymeric nitrogen-containing compound, including but not limited to those commonly used in the art.

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

  The adhesion aid is not particularly limited, and any of those commonly used in the art can be used.

  In one embodiment herein, the adhesion aid may be KBM-503.

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

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

  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 generally, the spin coating method is widely used. In addition, after forming the coating film, the residual solvent can be partially removed under reduced pressure in some cases.

  Examples of the light source for curing the photosensitive resin composition according to the present specification include a mercury vapor arc (arc) that emits light having a wavelength of 250 nm to 450 nm, a carbon arc, and a Xe arc, but this is not always necessary. Not limited to

  The photosensitive resin composition according to the present specification is a pigment dispersion type photosensitive material for manufacturing a thin film transistor liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film transistor liquid crystal display (TFT LCD) or an organic light emitting diode, Overcoat layer forming photosensitive material, column spacer photosensitive material, photo-curable paint, photo-curable ink, photo-curable adhesive, printing plate, printed wiring board photosensitive material, plasma display panel (PDP) photosensitive material, etc. It can be used and its application is not particularly limited.

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

  The color filter may be manufactured using a photosensitive resin composition including the compound represented by 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 is excellent in heat resistance, has a small change in color due to heat treatment, has a high color reproducibility even during a curing process during the production of a color filter, and has a high brightness and a light-dark ratio. It is possible to provide a high color filter.

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

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

  According to another embodiment, the color filter may further 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 the 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 etching can be used. However, in consideration of high process cost, high reflectance of chromium, and environmental pollution due to chromium waste liquid, it is possible to use a resin black matrix by a pigment dispersion method that allows fine processing.

  The black matrix according to one embodiment of the present specification may use a black pigment or a black dye as a coloring material. For example, carbon black may be used alone, or carbon black and a coloring pigment may be mixed and 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 adhesiveness to the substrate does not decrease even if the value increases.

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

  The display device includes a plasma display panel (PDP), a light emitting diode (LED), an organic light emitting diode (OLED), a liquid crystal display (LCD), a liquid crystal display device, and a liquid crystal display device (LCD). It may be one of a liquid crystal display device (Thin FIlm Transistor-Liquid Crystal Display, LCD-TFT) and a cathode ray tube (Cathode Ray Tube, CRT).

  Hereinafter, the present specification will be described in detail with reference to Examples. However, the embodiments according to the present specification can be modified into various different forms, and the scope of the present specification is not construed as being limited to the embodiments described below. The examples herein are provided to those of ordinary skill in the art to more fully describe the present specification.

  Manufacturing example.

[Production of Compound A]

  80 ml of distilled water was added to 11.8 g (0.08 mol / 1 eq) of phthalic anhydride (Phthalic anhydride), and after stirring at room temperature for 30 minutes, N-ethylethylenediamine (N-ethylethylenediamine) 7.26 g (0.082 mol / 0.082 mol / eq) After adding 1.03 eq), the temperature was raised to 105 ° C. with stirring. After reacting for 4 hours, it was cooled to room temperature.

  The pressure was reduced to remove distilled water, 60 mL of acetone was added, and the mixture was stirred at room temperature for 2 hours. Acetone was removed under reduced pressure and recrystallized from isopropyl alcohol (IPA) to obtain 13.5 g of white powder. (Yield 77.37%)

  Ionization mode: APCI +: m / z = 219 [M + H] +, Exact Mass: 218

[Production of Compound B]

  Phthalic anhydride 11.8 g (0.08 mol / 1 eq) and N-isopropylethane-1,2-diamine (N-isopropyethane-1,2-diamine) 8.42 g (0.082 mol / 1. 03eq) was added and the compound A was manufactured in the same manner as for the compound A to obtain 10.5 g of the compound B. (Yield 57%)

  Ionization mode: APCI +: m / z = 233 [M + H] +, Exact Mass: 232

[Production of Compound C]

  Phthalic anhydride 11.8 g (0.08 mol / 1 eq) and 2-((2-aminoethyl) amino) ethan-1-ol (2-((2-aminoethyl) amino) ethane-1- ol) (8.52 g, 0.082 mol / 1.03 eq) was added, and the compound A was produced in the same manner as for the compound A to obtain 12.3 g of the compound C. (Yield 65%)

  Ionization mode: APCI +: m / z = 235 [M + H] +, Exact Mass: 234

[Production of Compound D]

  Phthalic anhydride 11.8 g (0.08 mol / 1 eq) and N-ethylpropane-1,3-diamine (N-ethylpropane-1,3-diamine) 8.38 g (0.082 mol / 1. 03eq) was added and the compound A was manufactured in the same manner as for the compound A to obtain 14.2 g of the compound D. (Yield 76.4%)

  Ionization mode: APCI +: m / z = 233 [M + H] +, Exact Mass: 232

[Production of Compound E]

Dichlorosulfofluorescein 0.81 g (0.002 mol, 1 eq) was dissolved in methanol (MeOH) 30 mL, diethylamine (Diethylamine) 1.04 g (0.01 mol, 5 eq) was added, and then reacted at room temperature for 2 hours. Let The reaction was quenched by quenching with a 1 M aqueous hydrochloric acid (HCl) solution, and extracted with CH ₂ Cl ₂ .

The organic layer was separated, washed with brine, dried over Na ₂ SO ₄ , and depressurized to remove the solvent. Purification by silica column chromatography (CH ₂ Cl ₂ : MeOH = 8: 1) provided 0.52 g of compound E. (Yield 56%)

[Production of Compound 1]

Compound A2g a (0.009 mol / 3 eq) were placed in distilled water 25 mL, stirring potassium carbonate _{(K 2} CO 3) add 1.24g (0.009mol / 3eq). After stirring for 30 minutes while raising the temperature to 60 ° C., 1.22 g (0.003 mol / 1 eq) of dichlorosulfofluorescein was added.

After stirring at 105 ° C. for 24 hours, cool to room temperature. The reaction was terminated by quenching with a 0.1 M hydrochloric acid (HCl) aqueous solution, and the precipitate was filtered under reduced pressure while sufficiently washing with distilled water and dried in an oven at 80 ° C. Purification by silica column chromatography (Silica column chromatography) (CH ₂ Cl ₂ : MeOH = 7: 1) provided 1.1 g of Compound 1. (Yield 47%)

  Ionization mode: APCI +: m / z = 769 [M + H] +, Exact Mass: 768

[Production of Compound 2]

  Compound B (2.09 g, 0.009 mol / 3 eq) and dichlorosulfofluorescein (1.22 g, 0.003 mol / 1 eq) were added, and the same procedure as in Compound 1 was repeated to obtain Compound 2 (0.98 g). (Yield 41%)

  Ionization mode: APCI +: m / z = 797 [M + H] +, Exact Mass: 796

[Production of Compound 3]

  2.1 g (0.009 mol / 3 eq) of compound C and 1.22 g (0.003 mol / 1 eq) of dichlorosulfofluorescein were added, and the same procedure as for compound 1 was performed to obtain 1.3 g of compound 3. (Yield 54%)

  Ionization mode: APCI +: m / z = 801 [M + H] +, Exact Mass: 800

[Production of Compound 4]

  Compound D (2.09 g, 0.009 mol / 3 eq) and dichlorosulfofluorescein (1.22 g, 0.003 mol / 1 eq) were added thereto, and Compound D (0.85 g) was obtained by the same procedure as for Compound 1. (36% yield)

  Ionization mode: APCI +: m / z = 797 [M + H] +, Exact Mass: 796

[Production of Compound 5]

  Compound A (0.65 g, 0.003 mol / 3 eq) and compound E (0.52 g, 0.001 mol / 1 eq) were added, and the mixture was produced in the same manner as for compound 1 to obtain compound 0.25 g. (Yield 40%)

  Ionization mode: APCI +: m / z = 624 [M + H] +, Exact Mass: 623

Compound of Comparative Example 1.

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

Compound of Comparative Example 2.

Acid Red289 5g (7.388mmol), N- (3- bromopropyl) phthalimide 3.961g _{(14.776mmol),} placed _K 2 CO 3 4.09 g of (29.554Mmol) in NMP100ml, 12 hours at 95 ° C. It was stirred. The reaction solution was cooled to room temperature and filtered under reduced pressure. The filtrate was added to 800 ml Ethylacetae. The mixture was allowed to stir at room temperature for 30 minutes, and the precipitate was filtered under reduced pressure to obtain the compound of Comparative Example 2.

  Example.

[Production of Example 1 of Photosensitive Resin Composition]
15 parts by weight of the compound 1 prepared above, 33 parts by weight of pigment R254, 16 parts by weight of binder A as a binder resin, and 4.5 parts by weight of a polyfunctional monomer (Dipentaerythritol hexaacrylate) based on 100 parts by weight of the total weight of the photosensitive resin composition. Parts by weight, leveling agent F-554 0.3 parts by weight, adhesion aid KBM-503 0.15 parts by weight, photoinitiator (PBG-3057) 0.5 parts by weight, solvent propylene glycol monomethyl ether acetate (PGMEA, Propylene). Example 1 of the photosensitive resin composition was manufactured by mixing 30.55 parts by weight of Glycol monomethyl ether acetate).

  The binder A used as the binder resin is a copolymer having a mass ratio of benzyl methacrylate; N-phenylmaleimide; styrene; methacrylic acid = 55: 9: 11: 25.

[Production of Examples 2 to 5 of Photosensitive Resin Composition]
Example 2 of the photosensitive resin composition was carried out in the same manner as in Example 1 of the photosensitive resin composition except that the compound 1 of Example 1 of the photosensitive resin composition was changed to the compound shown in Table 1 below. 5 was produced.

  Comparative example.

[Production of Comparative Example 1 of Photosensitive Resin Composition]
Comparative Example 1 of the photosensitive resin composition in the same manner as in Example 1 of the photosensitive resin composition except that the compound of Example 1 of the photosensitive resin composition was changed to the compound of Comparative Example 1 (Rhodamine 6G). Was manufactured.

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

  Experimental example.

[Fabrication of substrate]
The photosensitive resin compositions prepared in Comparative Example 1 and Examples 1 to 5 were spin-coated on glass (5 cm × 5 cm) and pre-baked at 100 ° C. for 100 seconds to form a film. It was

The substrate on which the film was formed was irradiated with an exposure amount of 40 mJ / cm ^{2 on} the entire surface of the substrate using an exposure device. Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-heated at 230 ° C. for 20 minutes to prepare a substrate.

[Heat resistance evaluation]
Using the spectroscope (MCPD, Otsuka Co.), the post-heat treatment (Post bake once) substrate produced under the above conditions was used to obtain an absorption spectrum in the wavelength range of 380 to 780 nm.

  Further, the post-heat treatment substrate (Post bake once) was additionally treated at 230 ° C. for 60 minutes to obtain a transmittance spectrum in the same equipment and the same measurement range.

Using the values L *, a *, and b * obtained from the absorption spectrum obtained by using the C light source as a backlight, ΔEab was calculated by the following calculation formula 1 and shown in Table 2 below.
[Calculation formula 1]
ΔEab (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2
A small ΔEab value means that there is little change in color, which means that the heat resistance is excellent.

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

[Foreign material evaluation]
The number of foreign matters on the surface of the 1 × 1 cm area of the manufactured substrate is 15 or more, X is indicated, Δ is 6 to 14, and 5 or less is indicated by ◯, and shown in Table 3 below.

  As shown in Formula 1 according to an embodiment of the present specification, in the case of a compound in which an alkylphthalimide is substituted on a nitrogen atom, the compound does not interfere with the dispersibility of an existing Millbase and is mixed with R254 Millbase. It was found that when used for a long time, there were few foreign substances on the surface, the pigment could be stabilized at high temperature, and the color change due to additional heat treatment was small. The mill base means a state in which an insoluble coloring material is well dispersed in the composition by adding a dispersant and a binder.

[Measurement of luminance of color coordinates]
The photosensitive resin compositions prepared in Comparative Example 2 and Examples 1 to 5 were spin-coated on glass (5 cm × 5 cm) and pre-baked at 100 ° C. for 100 seconds to form a film. It was

The substrate on which the film was formed was irradiated with an exposure amount of 40 mJ / cm ^{2 on} the entire surface of the substrate using an exposure device. Then, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and post-heated at 230 ° C. for 20 minutes to prepare a substrate.

Color coordinates (x, y) and luminance (Y) of the manufactured substrate were measured using a spectroscope (MCPD, Otsuka Co., Ltd.) and shown in Table 4 below.

  According to Table 4, it can be confirmed that the substrates manufactured in Examples 1 to 5 have higher brightness and excellent color characteristics than the substrates manufactured in Comparative Example 2.

[Measurement of maximum absorption wavelength]
The compound of Comparative Example 2 and the compounds 1 to 5 were dissolved in propylene glycol monomethyl ether acetate (PGMEA) at a temperature of 25 ° C. at a concentration of 10 ⁻⁵ mol, and the maximum absorption wavelength was measured using a UV-visible spectrometer (SCINCO). Was measured and is shown in Table 5 below.

  According to Table 5, the maximum absorption wavelengths of Compounds 1 to 5 are 5 to 8 nm longer than the maximum absorption wavelength of the compound of Comparative Example 2, and when the red color filter is applied, the color coordinates are reduced in a smaller amount. I was able to confirm that it could be realized.

Claims (15)

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

In Chemical Formula 1,
R _{1 to} R ₆ are the same or different from each other, and each independently, hydrogen; deuterium; a halogen group; a nitro group; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; An unsubstituted alkoxy group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic group having 2 to 30 carbon atoms Selected from the group consisting of heteroaryl groups,
R ₇ to R _11, equal to or different from each other, each independently, hydrogen, deuterium, ^{_{halogen; -OH; -SO 3 -; -SO}} 3 H; -SO 3 Ra; -SO 2 NRbRc; -SO 2 NHRd; -COOH; -COORa; -CONHRd; substituted or unsubstituted C1-C30 linear or branched alkyl group; substituted or unsubstituted C6-C30 monocyclic or polycyclic aryl A group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
Ra to Rd are the same or different from each other, and each independently, a substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic group having 6 to 30 carbon atoms. A cyclic aryl group; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms,
R ₁₂ is hydrogen; deuterium; a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted, monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; and a dianhydride group containing a nitrogen atom,
R ₁₃ and R ₁₄ are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
R ₁₅ and R ₁₆ are the same or different from each other, and each independently, hydrogen; deuterium; -OH; a substituted or unsubstituted C 1 to C 30 straight or branched chain alkyl group; a substituted or unsubstituted A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or substituted by bonding to each other. Or an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms,
L ₁ and _{L 2,} equal to or different from each other, each independently, a direct bond; an alkylene group having a linear or branched substituted or unsubstituted _{C2-30; -L 3 -O-L 4 -} ; _{-L 3 -S-L 4 -;} - L 3 -NH-L 4 -; - L 3 -CO-L 4 -; - L 3 -COO-L 4 -; - L 3 -OCO-L 4 -; -L _{3 -NHCO-L 4} -; and _-L 3 _{-CONH-L 4} - is selected from the group consisting of,
L ₃ and L ₄ are the same or different from each other, and are a substituted or unsubstituted C _{1 to} C 30 linear or branched alkylene group,
a is an integer of 0 or 1,
X is an anionic group. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2:
[Chemical formula 2]

In the chemical formula 2,
R _{1 to} R ₁₁ , R _{13 to} R ₁₆ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1,
R ₁₇ and R ₁₈ are the same or different from each other, and independently of each other, hydrogen; deuterium; -OH; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted A monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms, or substituted by bonding to each other Alternatively, it forms an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic ring having 2 to 30 carbon atoms. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3:
[Chemical formula 3]

In Chemical Formula 3,
R _{1 to} R ₁₄ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1,
R ₁₉ is hydrogen; deuterium; a substituted or unsubstituted C1-C30 linear or branched alkyl group; a substituted or unsubstituted C1-C30 alkoxy group; a substituted or unsubstituted carbon monocyclic or polycyclic heteroaryl group or a substituted or unsubstituted 2 to 30 carbon atoms; number 6-30 monocyclic or polycyclic aryl group a halogen group; a nitro group; -COOH; -OH; -SO ₃ ^-; it is selected from the group consisting of and _-SO 2 NHRd,; sulfonic acid group; a sulfonic acid ester group; _sulfonate; -SO 2 NRbRc
Rb to Rd are the same or different from each other, and are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
m is an integer of 1 to 4, and when m is 2 or more, R _19's are the same or different from each other. The compound of claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4:
[Chemical formula 4]

In Chemical Formula 4,
R _{1 to} R ₁₁ , R ₁₃ , R ₁₄ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1,
R ₁₉ and R ₂₀ are the same or different from each other, and independently of each other, hydrogen; deuterium; a substituted or unsubstituted C 1 to C 30 linear or branched alkyl group; a substituted or unsubstituted C 1 An alkoxy group having 30 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; a halogen group; a nitro ^{_{group; -COOH; -OH; -SO 3 -}} ; sulfonic acid group; a sulfonic acid ester group; _sulfonate; is selected from the group consisting of and _-SO 2 NHRd,; _-SO 2 NRbRc
Rb to Rd are the same or different from each other, and each independently, Ra to Rd are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms,
m is an integer of 1 to 4,
n is an integer of 1 to 4,
When m is 2 or more, R _19's are the same or different from each other,
When n is 2 or more, R _20's are the same or different from each other.   X is an anion of a compound containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus; an anion containing boron; an anion containing a sulfonate group; and a halogen. The compound according to any one of claims 1 to 4, which is selected from the group consisting of anions containing groups. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas:

In the above chemical formula, X is as defined in the above chemical formula 1. R ₁₃ and R ₁₄ are the same or different from each other, and each independently represent a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 10 carbon atoms. The described compound.   A coloring material composition comprising the compound according to claim 1.   The coloring material composition according to claim 8, further comprising at least one of a dye and a pigment.   A photosensitive resin composition comprising the compound according to claim 1; a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent. The content of the compound represented by Chemical Formula 1 is 5 wt% to 60 wt% based on the total weight of solids in the photosensitive resin composition,
The content of the binder resin is 1% to 60% by weight,
The content of the photoinitiator is 0.1% to 20% by weight,
The photosensitive resin composition according to claim 10, wherein the content of the polyfunctional monomer is 0.1% by weight to 50% by weight.   The photosensitive resin composition according to claim 10, further comprising an additive.   A photosensitive material produced using the photosensitive resin composition according to claim 10.   A color filter comprising the photosensitive material according to claim 13.   A display device comprising the color filter according to claim 14.