JP6828923B2 - Xanthene compounds, color material compositions, photosensitive resin compositions, photosensitive materials, color filters and display devices - Google Patents

Description

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

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

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

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

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

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

The present inventors intend to provide a xanthene compound, a color material composition containing the xanthene compound, a photosensitive resin composition, a photosensitive material produced by using the xanthene compound, 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 the following chemical formula 1.
[Chemical formula 1]

In the chemical formula 1,
R _{1 to} R ₆ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitro group; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or substituted. Alkoxy groups having 1 to 30 carbon atoms unsubstituted; aryl groups having 6 to 30 carbon atoms substituted or unsubstituted; and monocyclic or polycyclic aryl groups having 2 to 30 carbon atoms substituted or unsubstituted. 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 linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and Selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.
Ra to Rd are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic groups having 6 to 30 carbon atoms. Selected from the group consisting of ring aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.
R ₁₂ is hydrogen; heavy hydrogen; 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; Selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms; and dianhydride groups containing a nitrogen atom.
R ₁₃ and R ₁₄ are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms.
R ₁₅ and R ₁₆ are identical or different from each other and independently of each other: hydrogen; hydrocarbons; -OH; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted. Selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms, or bonded to each other and substituted. Alternatively, an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
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 linear or branched alkylene groups having 1 to 30 carbon atoms that are identical or different from each other and are substituted or unsubstituted.
a is an integer of 0 or 1 and
X is an anionic group.

One embodiment of the present specification provides a colorant composition containing the compound represented by the chemical formula 1.

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

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

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

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

The xanthene compound according to one embodiment of the present specification can be used as a coloring material in a photosensitive resin composition, and has a harmony between a spectrum emitted from a light source and an absorption and transmission spectrum of a color filter as compared with a conventional coloring material. Therefore, the color purity can be increased.

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

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

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

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

In the chemical formula 1, when the nitrogen atom is substituted with alkyl phthalimide, the dispersibility of the pigment can be enhanced, the crystal transition of the pigment can be suppressed at a high temperature, and the pigment can be stabilized at a high temperature. This makes it possible to improve dispersibility and storage stability and reduce color change by stabilizing the pigment.

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 region of 550 to 580 nm, and the transmittance is excellent at 600 nm or more, and the 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 the chemical formula 1 will be described below, but the present invention is not limited thereto.

As used herein, the term "substituted or unsubstituted" refers to a heavy hydrogen; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a silyl group; an aryl group; an alkylsulfoxi group; an arylsulfoxi group. Boron group; alkylamine group; arylamine group; heteroaryl group; ether group; nitrile group; nitro group; hydroxy group (-OH); carboxy group (-COOH); -SO ^3- ; sulfonic acid group; sulfonic acid Is it substituted with one or more substituents selected from the group containing heterocyclic groups and anionic groups containing one or more of the ester group; sulfonic acid base; N, O, S, or P atoms? , Or does not have any substituents.

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

In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 2 to 30 are preferable. Specifically, it may be 2 to 20 or 2 to 10. As a specific example, an alkenyl group in which an aryl group such as a stylbenyl group or a styrenyl group is substituted is preferable, but the alkenyl group is not limited thereto.

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

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

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

In this specification, the sulfonic acid group may be represented by -SO ₃ H.

In the present specification, each sulfonic acid base is a salt with a monovalent cation, and the monovalent cation is any one selected from the group containing Na ⁺ , K ⁺ , and quaternary ammonium cations. There may be one, but it is not limited to this. Specific examples of the quaternary ammonium cation may be, but are not limited to, tetraalkylammonium cations such as tetramethylammonium cation, ethyltrimethylammonium cation, and tetrapropylammonium cation.

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

In the present specification, the sulfonamide group may be expressed as -SO ₂ NRxRy, and for example, Rx and Ry are the same or different from each other, and each independently has 1 to 30 substituted or unsubstituted carbon atoms. Linear or branched alkyl group; substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or substituted or unsubstituted monocyclic or polycyclic aryl group having 2 to 30 carbon atoms. It is an aryl group.

As used herein, 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 those having 6 to 30 carbon atoms are preferable. Specifically, it may have 6 to 20 carbon atoms or 6 to 12 carbon atoms. For example, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto.

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

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

In the present specification, the above-mentioned description of the heterocyclic group is applicable except that the heteroaryl group is aromatic. The number of carbon atoms 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 other embodiments.

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

As used herein, an alkenylene group means an alkene having two binding positions. The alkenylene group may be a straight chain, a branched chain or a ring chain. The carbon number of the alkenylene group is not particularly limited, but is, for example, 2 to 30 carbon atoms. Specifically, it may be 2 to 20, and more specifically, it may be 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, Japan Kai No. 2006-003080, Japanese Patent Application Laid-Open No. 2006-001917, Japanese Patent Application Laid-Open No. 2005-159926, Japanese Patent Application Laid-Open No. 2007-70288897, Japanese Patent Application Laid-Open No. 2005-071680, Korean application published The anions described in Japanese Patent Application Laid-Open No. 2007-7000393, Japanese Patent Application Laid-Open No. 2005-111696, Japanese Patent Application Laid-Open No. 2008-249663, and Japanese Patent Application Laid-Open No. 2014-199436 can be applied. Specific examples of the anionic group include an anion of a compound containing oxygen and at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus; a trifluolmethanesulfonic acid anion, a bis. (Trifluoromethylsulfonyl) amide anion, bistrifluolmethanesulfonimide anion, bisperfluoroethylsulfonimide anion, tetraphenylborate anion, tetrax (4-fluorophenyl) borate, tetrax (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., but they are not limited to these.

As used herein, anionic groups can have anions by 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 according to the number of substituted anionic groups. Since one amine group of the compound of the present invention has a cation, the total charge of the entire molecule is from the anion to 0, which is the number of substituted anionic groups minus one. Can have a value of.

According to the above-described embodiment, in Formula 1, wherein R ₁ to R _6, equal to or different from each other, each independently, hydrogen, deuterium, halogen, nitro groups, substituted or unsubstituted carbon atoms 1 30 linear or branched alkyl groups; substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted It may be selected from the group consisting of monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms for substitution.

According to another embodiment of the present specification, the R _{1 to} R ₆ are the same as or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitro group; substituted or unsubstituted carbon number 1 to 1. 20 linear or branched alkyl groups; substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; and substituted or unsubstituted It may be selected from the group consisting of a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms for substitution.

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

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

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

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

According to another embodiment of the present specification, the R ₁ to R _6, equal to or different from each other, each independently, hydrogen; fluorine; or a methyl group.

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

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

According to another embodiment of the specification, the R ₁ and R ₄ may be 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 groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms. And selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.
Ra to Rd are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic groups having 6 to 30 carbon atoms. It is selected from the group consisting of ring aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.

According to another embodiment of the present specification, the _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 20 carbon atoms; substituted or unsubstituted carbon number Selected from the group consisting of 6 to 20 monocyclic or polycyclic aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 20 carbon atoms.
Ra to Rd are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted monocyclic or polycyclic groups having 6 to 20 carbon atoms. It is selected from the group consisting of ring aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 20 carbon atoms.

According to another embodiment of the present specification, the _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 10 carbon atoms; substituted or unsubstituted carbon number Selected from the group consisting of 6-12 monocyclic or polycyclic aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2-10 carbon atoms.
Ra to Rd are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 10 carbon atoms; substituted or unsubstituted monocyclic or polycyclic groups having 6 to 12 carbon atoms. It is selected from the group consisting of ring aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 10 carbon atoms.

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

According to one embodiment of the present specification, the _R 7 _{to R 11,} equal to or different from each other, each independently, _hydrogen; ^-SO 3 -; may be or _-SO 2 NHRd; _-SO 3 H However, the Rd may be an ethyl group-substituted hexyl group; or an ethyl group-substituted or unsubstituted propyl group.

In addition, R ₁₂ is hydrogen; heavy hydrogen; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms. It may be selected from the group consisting of 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 herein, R ₁₂ is hydrogen; deuterium; substituted or unsubstituted carbon atoms, alkyl group of straight or branched chain substituted or unsubstituted C 1-20 Selected from the group consisting of 6-20 monocyclic or polycyclic aryl groups; substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 20 carbon atoms; and dianhydride groups containing nitrogen atoms. May be good.

According to another embodiment herein, R ₁₂ is hydrogen; deuterium, alkyl group substituted or unsubstituted straight or branched chain having 1 to 10 carbon atoms; a substituted or unsubstituted carbon atoms Selected from the group consisting of 6-12 monocyclic or polycyclic aryl groups; substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 10 carbon atoms; and dianhydride groups containing nitrogen atoms. May be good.

According to another embodiment herein, R ₁₂ represents an alkyl group of straight or branched chain having 1 to 10 carbon atoms substituted or unsubstituted; a dianhydride group containing or nitrogen atom May be good.

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

According to another embodiment herein, R ₁₂ is a methyl group; or a dianhydride group containing or nitrogen atom; ethyl; propyl; isopropyl; isobutyl.

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

The R ₁₃ and R ₁₄ may emit light in the red wavelength region when they are the same or different from each other and independently have a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms. When a color filter is produced from a photosensitive material containing a compound represented by the structure of the 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 the chemical formula 1 exists in the region of 550 to 580 nm, and the transmittance is excellent at 600 nm or more. It is easy to realize colors in the red wavelength region.

According to another embodiment of the specification, R ₁₃ and R ₁₄ are the same or different from each other and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms. There may be.

According to another embodiment of the specification, R ₁₃ and R ₁₄ are the same or different from each other and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 10 carbon atoms. There may be.

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

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

In addition, R ₁₅ and R ₁₆ are the same or different from each other, and independently, hydrogen; hydrocarbon; -OH; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or non-substituted. Selected from the group consisting of substituted monocyclic or polycyclic aryl groups with 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups with 2 to 30 carbon atoms, or bonded to each other. A substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms 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 independently, hydrogen; hydrocarbon; -OH; substituted or unsubstituted linear having 1 to 20 carbon atoms. Alternatively, from branched alkyl groups; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 20 carbon atoms. A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted or bonded to each other; or a monocyclic ring having 2 to 20 carbon atoms substituted or unsubstituted or Polycyclic heterocycles 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 independently, hydrogen; hydrocarbon; -OH; substituted or unsubstituted linear having 1 to 10 carbon atoms. Alternatively, from branched alkyl groups; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 12 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 10 carbon atoms. A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms substituted or unsubstituted or bonded to each other; or a monocyclic ring having 2 to 10 carbon atoms substituted or unsubstituted or Polycyclic heterocycles 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 specification, R ₁₅ and R ₁₆ may combine with 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 methyl group substituted or unsubstituted benzene ring.

Further, L ₁ and L ₂ are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkylene groups having 2 to 30 carbon atoms; −L ₃ −OL 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 substituted or unsubstituted linear or branched alkylene groups 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 the case of a linear or branched alkylene group having 1 to 30 carbon atoms substituted or unsubstituted, and the above 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 linear or branched alkylene group having 2 to 30 carbon atoms which is substituted or unsubstituted, 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 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 independently substituted or unsubstituted linear or branched alkylene groups having 2 to 20 carbon atoms; −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 substituted or unsubstituted linear or branched alkylene groups having 1 to 20 carbon atoms.

In one embodiment of the specification, L ₁ and L ₂ are the same or different from each other and are independently substituted or unsubstituted linear or branched alkylene groups having 2 to 10 carbon atoms; −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 substituted or unsubstituted linear or branched alkylene groups having 1 to 10 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ may be the same or different from each other, and may be independently substituted or unsubstituted linear or branched alkylene groups having 2 to 10 carbon atoms. ..

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

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

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

In another embodiment of the specification, a is 0.

In another embodiment of the specification, a is 1.

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

In one embodiment of the specification, the 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; It may be selected from the group consisting of anions containing an acid group; and anions containing a halogen group.

In one embodiment of the specification, the 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; a trifluolmethanesulfonic acid anion. Bis (trifluoromethylsulfonyl) amide anion; bistrifluolmethanesulfonimide anion; bisperfluoroethylsulfonimide anion; tetraphenylborate anion; tetrakis (4-fluorophenyl) borate; tetrakis (pentafluoro) It may be selected from the group consisting of 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, the chemical formula 1 may be represented by the following structure, the following structure represents an isomer of the chemical formula 1, and the chemical formula 1 represents a representative structure. .. An isomer means a molecule having the same molecular formula but having different physical / chemical properties from each other.

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

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, 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 above.
R ₁₇ and R ₁₈ are identical or different from each other, and independently of each other, hydrogen; hydrocarbons; hydroxy groups; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted. Selected from the group containing monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms, or bonded to each other and substituted. Alternatively, an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.

In one embodiment of the specification, R ₁₇ and R ₁₈ are identical or different from each other and independently of hydrogen; hydrocarbons; hydroxy groups; substituted or unsubstituted linear or branched chains having 1 to 20 carbon atoms. Alkyl groups; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic aryl groups having 2 to 20 carbon atoms selected from the group containing A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted by binding to each other; or a monocyclic or polycyclic heterocyclic ring having 2 to 20 carbon atoms substituted or unsubstituted. Form a ring.

In one embodiment of the specification, R ₁₇ and R ₁₈ are identical or different from each other and independently of hydrogen; hydrocarbons; hydroxy groups; substituted or unsubstituted linear or branched chains having 1 to 10 carbon atoms. Alkyl groups; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 12 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic aryl groups having 2 to 10 carbon atoms selected from the group containing A monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 12 carbon atoms substituted or unsubstituted by binding to each other; or a monocyclic or polycyclic heterocyclic ring having 2 to 10 carbon atoms substituted or unsubstituted. 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 of the specification, 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 methyl group substituted or unsubstituted benzene ring.

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。 Further, according to another embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 3.
[Chemical formula 3]

In the chemical formula 3,
R _{1 to} R ₁₄ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1 above.
R ₁₉ is hydrogen; heavy hydrogen; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; substituted or unsubstituted carbon. Monocyclic or polycyclic aryl group of number 6 to 30; substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; halogen group; nitro group; -COOH; -OH; sulfonic acid group Selected from the group consisting of sulfonic acid ester groups; sulfonic acid bases; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd are linear or branched alkyl groups having 1 to 30 carbon atoms, which are identical or different from each other and are independently substituted or unsubstituted.
m is an integer of 1 to 4, and when m is 2 or more, R ₁₉ is the same as or different from each other.

In another embodiment of the specification, R ₁₉ is hydrogen; dehydrogen; substituted or unsubstituted linear or branched alkyl groups with 1 to 20 carbon atoms; substituted or unsubstituted carbon atoms 1 to 20. 20 alkoxy groups; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 20 carbon atoms; substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 20 carbon atoms; halogen groups; nitro Groups; -COOH; -OH; sulfonic acid groups; sulfonic acid ester groups; sulfonic acid bases; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd are the same or different, independently substituted or substituted linear or branched alkyl groups having 1 to 20 carbon atoms.
m is an integer of 1 to 4, and when m is 2 or more, R ₁₉ is the same as or different from each other.

In another embodiment of the specification, R ₁₉ is hydrogen; dehydrogen; substituted or unsubstituted linear or branched alkyl groups having 1 to 10 carbon atoms; substituted or unsubstituted carbon atoms 1 to 10. 10 alkoxy groups; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 12 carbon atoms; substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 10 carbon atoms; halogen groups; nitro Groups; -COOH; -OH; sulfonic acid groups; sulfonic acid ester groups; sulfonic acid bases; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd are the same or different, independently substituted or substituted linear or branched alkyl groups having 1 to 10 carbon atoms.
m is an integer of 1 to 4, and when m is 2 or more, R ₁₉ is the same as or different from each other.

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

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

According to another embodiment herein, R ₁₉ is hydrogen; or 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 from 1-2, when m is 2, R ₁₉ may be the same or different from each other.

In one embodiment of the 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。 Further, according to another embodiment of the present specification, the chemical formula 1 is represented by the following chemical formula 4.
[Chemical formula 4]

In the 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 above.
R ₁₉ and R ₂₀ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon number 1 Alkyl groups to 30; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms; halogen groups; Selected from the group consisting of nitro group; -COOH; -OH; sulfonic acid group; sulfonic acid ester group; sulfonic acid base; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd are linear or branched alkyl groups having 1 to 30 carbon atoms, which are identical or different from each other and are independently substituted or unsubstituted.
m is an integer of 1 to 4 and
n is an integer of 1 to 4 and
When m is 2 or more, R ₁₉ are the same or different from each other.
When n is 2 or more, R _20s are the same or different from each other.

In one embodiment of the specification, R ₁₉ and R ₂₀ are the same or different from each other and are independent of each other, hydrogen; heavy hydrogen; substituted or unsubstituted, linear or branched alkyl groups having 1 to 20 carbon atoms. 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. Selected from the group consisting of heteroaryl groups of rings; halogen groups; nitro groups; -COOH; -OH; sulfonic acid groups; sulfonic acid ester groups; sulfonic acid bases; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd may be the same or different from each other, and may be substituted or unsubstituted linear or branched alkyl groups having 1 to 20 carbon atoms, respectively.

In one embodiment of the specification, R ₁₉ and R ₂₀ are the same or different from each other and independently of each other, hydrogen; heavy hydrogen; substituted or unsubstituted, linear or branched alkyl groups having 1 to 10 carbon atoms. An alkoxy group having 1 to 10 carbon atoms substituted or unsubstituted; a monocyclic or polycyclic aryl group having 6 to 12 carbon atoms substituted or unsubstituted; a monocyclic or polycyclic or polycyclic group having 2 to 10 carbon atoms substituted or unsubstituted. Selected from the group consisting of heteroaryl groups of rings; halogen groups; nitro groups; -COOH; -OH; sulfonic acid groups; sulfonic acid ester groups; sulfonic acid bases; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd may be the same or different from each other, and may be substituted or unsubstituted linear or branched alkyl groups having 1 to 10 carbon atoms, respectively.

In one embodiment of the specification, R ₁₉ and R ₂₀ are hydrogen; or substituted or unsubstituted linear or branched alkyl groups having 1 to 10 carbon atoms, which are the same or different from each other and are independent of each other. ..

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

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

前記化学式中、Ｘは、前記化学式１で定義した通りである。 Further, the compound represented by the chemical formula 1 may be represented by any one of the following chemical formulas, but the compound is not necessarily limited to this.

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

In one embodiment of the specification, the compound represented by Chemical Formula 1 has a maximum absorption wavelength of 557 nm to 570 nm. Specifically, the compound represented by the 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, color coordinates can be realized in a smaller amount when a 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).

Moreover, one embodiment of this specification provides a color material composition containing the said compound.

Further, according to one embodiment of the specification, the colorant composition may further comprise at least one of a dye and a pigment.

For example, the coloring material composition may contain only the compound of the chemical formula 1, but may contain the compound of the chemical formula 1 and one or more dyes, or the compound of the chemical formula 1 and one or more pigments. It may contain the compound of the above chemical formula 1, one or more dyes, and one or more pigments.

The dyes and pigments are metal-complex-based compounds; azo-based compounds; metal-azo-based compounds; quinophothalone-based compounds; isoindoline-based compounds; methine. (Methine) -based compounds; phthalocyanine-based compounds; metal phthalocyanine-based compounds; porphyrin-based compounds; metal porphyrin-based compounds; tetraazaporphyrin-based compounds; tetraazaporphyrin-based compounds; Tetra azaporphyrin (metal terra aza porphyrin) -based compounds; cyanine-based compounds; Xanthene-based compounds; metal dipyrromethane-based compounds; boron dipyrromethene-based compounds. Compounds; one or more may be selected from the group consisting of diketopyrrolopyrrole-based compounds; triarylmethane-based compounds; and perylene-based compounds.

According to one embodiment of the present specification, the pigment further contained in addition to the compound of Chemical Formula 1 may be, for example, R254 (Pigment Red254), but is not limited thereto. The R254 is in a Millbase state and may be commercially available. The mill base means a state in which an insoluble coloring material is well dispersed on the composition by adding a dispersant, a binder and the like.

One embodiment of the present specification provides a photosensitive resin composition containing the colorant composition.

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

The photosensitive resin composition may further contain 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 by the photosensitive resin composition.

As the binder resin, a copolymer resin of a polyfunctional monomer that imparts mechanical strength of the film and a monomer that imparts alkali solubility can be used, and even if a binder generally used in the art is included. Good.

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

Specific examples of the unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, and isobutyl (meth) acrylate. , T-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, hydroxyethyl (meth) acrylate , 2-Hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate , 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl Ether (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, glycidyl (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1, , 1,1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, methyl α-hydroxymethyl acrylate , Ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate, and butyl α-hydroxymethyl acrylate may be selected from the group, but is not limited thereto.

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

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

Specific examples of the unsaturated imides may be selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide, and N-cyclohexylmaleimide. , Not limited to these.

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

The monomer that imparts alkali solubility is not particularly limited as long as it contains an acid group, and for example, (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethylmaleic acid, 5-norbornene-2- 1 selected from the group consisting of carboxylic acid, mono-2-((meth) acryloyloxy) ethylphthalate, mono-2-((meth) acryloyloxy) ethylsuccinate, ω-carboxypolycaprolactone mono (meth) acrylate 1 It is preferable to use more than seeds, but it is not limited to these.

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

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

In one 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, respectively.

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

In one 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 cross-linking by generating radicals with light, but is selected from the group consisting of, for example, an acetophenone-based compound, a biimidazole-based compound, a triazine-based compound, and an oxime-based compound. It may be one or more kinds.

The acetphenone compounds are 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-1-one, 4- (2-). Hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, benzoinmethyl ether, benzoin ethyl ether, benzoin isobutyl ether, benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-Methyl- (4-methylthio) Phenyl-2-morpholino-1-propane-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, 2-( 4-Bromo-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane-1-one, or 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one And are not limited to these.

Examples of the biimidazole compound include 2,2-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (o-chlorophenyl) -4,4'. , 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4', 5,5' -Tetraphenyl biimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like, but not limited to these.

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

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

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

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

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

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

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

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

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

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

As used herein, the additives may be leveling agents and adhesion aids.

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

In one embodiment of the present specification, the content of the compound represented by the chemical formula 1 is 5% by weight to 60% by weight, and the content of the pigment is based on the total weight of the photosensitive resin composition. The content of the binder resin is 5% by weight to 40% by weight, the content of the binder resin is 1% by weight to 60% by weight, the content of the photoinitiator is 0.1% by weight to 20% by weight, and the polyfunctional monomer. The content of the above is 0.1% by weight to 50% by weight, the content of the solvent is 10% by weight to 80% by weight, and the content of the additive is 0.1% by weight to 20% by weight. You may.

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

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

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-Tiasazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate), pentaerythritol-tetrakis (2) -Selected from the group consisting of pentaerythritol-tris (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) 1 More than seeds can be used.

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

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

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

Specific examples of the antioxidant are 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-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4) -Methyl-6-t-butylphenol), 2,6-g, t-butylphenol 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- 6-t-butylphenol), or bis [3,3-bis- (4'-hydroxy-3'-tart-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy-) Hindered phenolic primary antioxidants such as 3'-tert-butylphenyl) butanoicacid] glycol ester); phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p- Phenylene diamine, or amine-based secondary antioxidants such as N, N'-di-β-naphthyl-p-phenylene diamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzo Thio-based secondary antioxidants such as thiazole, or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, Bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) pentaerythritol diphosphite, or (1,1'-biphenyl) -4,4'-diylbisphosphonasate tetrakis 4-Bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous ac Examples thereof include phosphite-based secondary antioxidants such as id tetrakis [2,4-bis (1,1-dimethyl) phenyl] ester).

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

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, N-nitrosophenylhydroxyamine ammonium salt, and 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) It can include, but is not limited to, one or more selected from the group consisting of −butylphenol), 2-mercaptoimidazole, and phenothiazine, but is generally known in the art. Can include those that are.

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

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

The leveling agent may be polymeric or non-polymeric. Specific examples of the polymeric leveling agent include polyethyleneimine, polyamideamine, and the reaction product of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymeric sulfur. And non-polymeric nitrogen-containing compounds, including, but not limited to, all commonly used in the art.

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

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

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

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

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

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

Examples of the light source for curing the photosensitive resin composition according to the present specification include a mercury steam arc (arc), a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm. Not limited to.

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

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

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

The photosensitive resin composition according to one embodiment of the present specification is excellent in heat resistance, has little color change due to heat treatment, has a high color reproduction rate even during the manufacturing and curing process of a color filter, and has a brightness and a light-dark ratio. Can provide a high color filter.

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

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

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

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

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

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

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

Hereinafter, in order to specifically explain the present specification, examples will be given and described in detail. However, the examples according to the present specification can be transformed into various different forms, and the scope of the present specification is not construed as being limited to the examples described below. The examples herein are provided to provide a more complete description of the specification to those with average knowledge in the art.

Production example.

[Production of Compound A]

Add 80 ml of distilled water to 11.8 g (0.08 mol / 1 eq) of phthalic anhydride, stir for 30 minutes at room temperature, and then 7.26 g (0.082 mol / 0.082 mol /) of N-Ethylethylenediamine. 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.

Distilled water was removed under reduced pressure, 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 give 13.5 g of white powder. (Yield 77.37%)

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

[Production of compound B]

11.8 g (0.08 mol / 1 eq) of phthalic anhydride (0.08 mol / 1 eq) and 8.42 g (0.082 mol / 1.) of N-isopropylethane-1,2-diamine. 03eq) was added and produced in the same manner as in Compound A to obtain 10.5 g of 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) ethane-1-ol (2-((2-aminoethyl) amineo) ether-1- ol) 8.54 g (0.082 mol / 1.03 eq) was added and produced in the same manner as in Compound A to obtain 12.3 g of 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-ethylpropan-1,3-diamine (N-ethyl compound-1,3-diamine) 8.38 g (0.082 mol / 1. 03eq) was added and produced in the same manner as in Compound A to obtain 14.2 g of Compound D. (Yield 76.4%)

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

[Production of Compound E]

0.81 g (0.002 mol, 1 eq) of dichloromethane (Dichlorosulfofluorescein) is dissolved in 30 mL of methanol (MeOH), 1.04 g (0.01 mol, 5 eq) of diethylamine (Diethylamine) is added, and then the reaction is carried out at room temperature for 2 hours. I let you. The reaction was terminated by quenching with a 1M aqueous hydrochloric acid (HCl) solution, and the mixture was 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) gave 0.52 g of compound E. (Yield 56%)

[Production of Compound 1]

2 g (0.009 mol / 3 eq) of compound A is placed in 25 mL of distilled water, and 1.24 g (0.009 mol / 3 eq) of potassium carbonate (K ₂ CO ₃ ) is added with stirring. 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 aqueous hydrochloric acid (HCl) solution, and the precipitate was filtered under reduced pressure while being thoroughly washed with distilled water and dried in an oven at 80 ° C. Purification by silica column chromatography (CH ₂ Cl ₂ : MeOH = 7: 1) gave 1.1 g of compound. (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 production as in Compound 1 was carried out to obtain Compound 2 0.98 g. (Yield 41%)

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

[Production of Compound 3]

Compound C 2.1 g (0.009 mol / 3 eq) and Dichlorosulfofluorescein (1.22 g (0.003 mol / 1 eq)) were added, and the same production as in Compound 1 was carried out to obtain Compound 3 1.3 g. (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 to obtain Compound 4 0.85 g. (Yield 36%)

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 produced in the same manner as in Compound 1 to obtain Compound 5 0.25 g. (Yield 40%)

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

The compound of Comparative Example 1.

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

Compound of Comparative Example 2.

Add 289 5 g (7.388 mmol) of Acid Red, 3.961 g (14.776 mmol) of N- (3-bromopropyl) phthalimide, and 4.09 g (29.554 mmol) of K ₂ CO _{3 to} 100 ml of NMP at 95 ° C. for 12 hours. Stirred. The reaction solution was cooled to room temperature and filtered under reduced pressure. The filtrate was added to 800 ml of Ethylacetae. The mixture was stirred at room temperature for 30 minutes and the precipitate was filtered under reduced pressure to give the compound of Comparative Example 2.

Example.

[Production of Example 1 of Photosensitive Resin Composition]
Based on the total weight of 100 parts by weight of the photosensitive resin composition, 15 parts by weight of the previously produced compound, 254 33 parts by weight of the pigment R, 16 parts by weight of the binder A as the binder resin, and 4.5 parts by weight of the dipentaerythritol hexaacrylate. Parts by weight, leveling agent F-554 0.3 parts by weight, adhesive auxiliary KBM-503 0.15 parts by weight, photoinitiator (PBG-3057) 0.5 parts by weight, solvent propylene glycol monomethyl ether acetate (PGMEA, Plasticene) Example 1 of the photosensitive resin composition was produced by mixing 30.55 parts by weight of Glycol monomer 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.

[Manufacturing of Examples 2 to 5 of the photosensitive resin composition]
Examples 2 to 2 of the photosensitive resin composition 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 compounds shown in Table 1 below. 5 was manufactured.

Comparative example.

[Manufacturing 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). Manufactured.

[Manufacturing 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.

[Preparation of substrate]
The photosensitive resin compositions produced in Comparative Examples 1 and 1 to 5 were spin-coated on glass (5 cm × 5 cm) and preheated (Prebake) 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. After that, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and then heat-treated (Post-bake) at 230 ° C. for 20 minutes to prepare a substrate.

[Heat resistance evaluation]
An absorption spectrum in the wavelength range of 380 to 780 nm was obtained using a spectroscope (MCPD, Otsuka Co., Ltd.) on the post-heat treatment (Post bake 1 time) substrate prepared under the above conditions.

In addition, 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 with the C light source as the backlight, ΔEab was calculated by the following formula 1 and shown in Table 2 below.
[Calculation formula 1]
ΔEab (L *, a *, b *) = {(ΔL *) ² + (Δa *) ² + (Δb *) ² } ^1/2
When the ΔEab value is small, it means that there is little color change, and it means that the heat resistance is excellent.

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

[Foreign matter evaluation]
If the number of foreign substances on the surface of the 1 × 1 cm region of the produced substrate is 15 or more, it is indicated as X, if it is 6 to 14, it is indicated as Δ, and if it is 5 or less, it is indicated as ○, and is shown in Table 3 below.

In the case of a compound in which an alkylphthalimide is substituted for a nitrogen atom as in the above chemical formula 1 according to one embodiment of the present specification, the compound is mixed with R254 millbase without interfering with the dispersibility of the existing millbase. It was found that there were few foreign substances on the surface, the pigment could be stabilized at high temperature, and there was little color change due to additional heat treatment. The Millbase means a state in which an insoluble coloring material is well dispersed on the composition by adding a dispersant, a binder and the like.

[Measurement of brightness of color coordinates]
The photosensitive resin compositions produced in Comparative Examples 2 and 1 to 5 were spin-coated on glass (5 cm × 5 cm) and preheated (Prebake) 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. After that, the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds, and then heat-treated (Post-bake) at 230 ° C. for 20 minutes to prepare a substrate.

The produced substrate was measured in color coordinates (x, y) and brightness (Y) using a spectroscope (MCPD, Otsuka), and is shown in Table 4 below.

According to Table 4, it was confirmed that the substrates produced by Examples 1 to 5 had higher brightness and exhibited excellent color characteristics than the substrates produced by Comparative Example 2.

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

According to Table 5, the maximum absorption wavelengths of the compounds 1 to 5 are extended by 5 to 8 nm from the maximum absorption wavelengths of the compounds of Comparative Example 2, and when the Red color filter is applied, the color coordinates can be adjusted with a smaller amount. I was able to confirm that it could be achieved.

Claims (15)

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

In the chemical formula 1,
R _{1 to} R ₆ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; nitro group; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or substituted. Alkoxy groups having 1 to 30 carbon atoms unsubstituted; aryl groups having 6 to 30 carbon atoms substituted or unsubstituted; and monocyclic or polycyclic aryl groups having 2 to 30 carbon atoms substituted or unsubstituted. 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 linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic aryl having 6 to 30 carbon atoms. Groups; and selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.
Ra to Rd are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic groups having 6 to 30 carbon atoms. Selected from the group consisting of ring aryl groups; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms.
R ₁₂ is hydrogen; heavy hydrogen; 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; Selected from the group consisting of substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms; and dianhydride groups containing a nitrogen atom.
R ₁₃ and R ₁₄ are linear or branched alkyl groups having 1 to 30 carbon atoms, which are identical or different from each other and are independently substituted or unsubstituted.
R ₁₅ and R ₁₆ are identical or different from each other and independently of each other: hydrogen; hydrocarbons; -OH; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted. Selected from the group consisting of monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms, or bonded to each other and substituted. Alternatively, an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed.
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 linear or branched alkylene groups having 1 to 30 carbon atoms that are identical or different from each other and are substituted or unsubstituted.
a is an integer of 0 or 1 and
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 above.
R ₁₇ and R ₁₈ are the same or different from each other, and independently of each other, hydrogen; hydrocarbons; -OH; substituted or unsubstituted linear or branched alkyl groups having 1 to 30 carbon atoms; substituted or unsubstituted. Selected from the group containing monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; and substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms, or bonded to each other and substituted. Alternatively, an unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocycle having 2 to 30 carbon atoms is formed. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 3.
[Chemical formula 3]

In the chemical formula 3,
R _{1 to} R ₁₄ , L ₁ , L ₂ , a and X are as defined in Chemical Formula 1 above.
R ₁₉ is hydrogen; heavy hydrogen; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; substituted or unsubstituted carbon. Monocyclic or polycyclic aryl group of number 6 to 30; substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; halogen group; nitro group; -COOH; -OH; -SO ₃ ^- ; Sulfonic acid group; Sulfonic acid ester group; Sulfonic acid base; -SO ₂ NRbRc; and -SO ₂ NHRd.
Rb to Rd are linear or branched alkyl groups having 1 to 30 carbon atoms, which are identical or different from each other and are independently substituted or unsubstituted.
m is an integer of 1 to 4, and when m is 2 or more, R ₁₉ is the same as or different from each other. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 4.
[Chemical formula 4]

In the 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 above.
R ₁₉ and R ₂₀ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; substituted or unsubstituted carbon number 1 Alkax groups of ~ 30; substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms; substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 2 to 30 carbon atoms; halogen groups; 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~Rd, equal to or different from each other, in their respective independently, a linear or branched alkyl group having a substituted or unsubstituted 1 to 30 carbon atoms,
m is an integer of 1 to 4 and
n is an integer of 1 to 4 and
When m is 2 or more, R ₁₉ are the same or different from each other.
When n is 2 or more, R _20s are the same or different from each other. The 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 sulfonic acid 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 a group. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas:

In the chemical formula, X is as defined in the chemical formula 1. According to any one of claims 1 to 5, R ₁₃ and R ₁₄ are the same or different from each other, and are independently substituted or unsubstituted linear or branched alkyl groups having 1 to 10 carbon atoms. The compound described. A color material composition containing the compound according to any one of claims 1 to 7. The color 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 any one of claims 1 to 7, a binder resin; a polyfunctional monomer; a photoinitiator; and a solvent. Based on the total weight of the solid content in the photosensitive resin composition, the content of the compound represented by the chemical formula 1 is 5% by weight to 60% by weight.
The content of the binder resin is 1% by weight to 60% by weight.
The content of the photoinitiator is 0.1% by weight to 20% by weight.
The 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 or 11, further comprising an additive. A photosensitive material produced by using the photosensitive resin composition according to any one of claims 10 to 12. A color filter containing the photosensitive material according to claim 13. A display device including the color filter according to claim 14.