JP2021517921A - Compounds, colorant compositions, photosensitive materials, color filters and display devices - Google Patents

Abstract

The present specification provides a compound containing a triarylmethane dye monomer; a (meth) acrylic acid monomer; and a structure represented by Chemical Formula 1, a colorant composition, a photosensitive material, a color filter and a display device.

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-010491 filed with the Korean Intellectual Property Office on September 6, 2018, the entire contents of which are incorporated herein by reference.

The present specification relates to compounds, colorant compositions, photosensitive materials, color filters and display devices.

At present, a pigment dispersion method using a pigment as a colorant is generally applied in order to realize a color filter. However, in the case of a pigment dispersion, not only the pigment exists in a particle state and scatters light, but also the surface area of the pigment rapidly increases due to the miniaturization of the pigment, which deteriorates the dispersion stability and causes non-uniform pigment. Particles are generated. Therefore, in order to achieve the recently required high brightness, high light-dark ratio and high resolution, it has recently been considered to use a dye instead of a pigment as a colorant.

In general, dyes have the advantage of being more transparent than pigments. However, there is a drawback that the heat resistance is insufficient as compared with the pigment. Further, it has a drawback that it has better solubility in an organic solvent than existing pigments and has insufficient chemical resistance.

The present specification seeks to provide compounds, colorant compositions, photosensitive materials, color filters and display devices.

One embodiment of the present specification provides a compound comprising a triarylmethane dye monomer; a (meth) acrylic acid monomer; and a structure represented by the following chemical formula 1.

[Chemical formula 1]

は、他のモノマーまたは結合部に連結される部分を意味し、
Ｘ'は、ＯまたはＮＨであり、
Ｌ１およびＬ２は、互いに同一または異なり、それぞれ独立して、直接結合；置換もしくは非置換のアルキレン基；−Ｃ（＝Ｏ）−；または−Ｌ３−Ｏ（Ｃ＝Ｏ）−であり、
Ｌ３は、置換もしくは非置換のアルキレン基であり、
Ｒ１〜Ｒ３は、互いに同一または異なり、それぞれ独立して、水素；ヒドロキシ基；置換もしくは非置換のアルキル基であり、
ｒ２は、０〜４の整数であり、ｒ２が２以上の場合、Ｒ２は、互いに同一または異なり、ｒ３は、０〜５の整数であり、ｒ３が２以上の場合、Ｒ３は、互いに同一または異なる。 In the chemical formula 1,

Means the part that is linked to another monomer or bond,
X'is O or NH,
L1 and L2 are the same or different from each other and are independently bonded; substituted or unsubstituted alkylene groups; -C (= O)-; or -L3-O (C = O)-.
L3 is a substituted or unsubstituted alkylene group.
R1 to R3 are hydrogen; hydroxy groups; substituted or unsubstituted alkyl groups, which are the same or different from each other and are independent of each other.
r2 is an integer from 0 to 4, and if r2 is 2 or more, R2 is the same or different from each other, r3 is an integer from 0 to 5, and if r3 is 2 or more, R3 is the same or different from each other. different.

One embodiment of the specification provides a colorant composition comprising said compound; binder resin; polyfunctional monomer; photoinitiator; and solvent.

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

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

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

The compound according to one embodiment of the present specification can be used as a coloring material in a colorant composition, and when a color filter is produced using the colorant composition, it is excellent in chemical resistance and heat resistance.

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

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

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

は、他のモノマー、他の置換基または結合部に連結される部分を意味する。 In the present specification

Means a moiety linked to another monomer, other substituent or bond.

は、他の結合部に連結される部分を意味する。 In the present specification

Means a portion connected to another joint.

As used herein, the "linkage" of the linked portions may be one that leads to a single bond or a double bond between atoms.

The binding portion means a portion connected between chemical formulas or chemical structures.

As used herein, the term "monomer" means a monomer or a unit, and means a unit molecule or a repeating structure forming a polymer.

In the present specification, the structure represented by the chemical formula 1 can mean a monomer having a structure represented by the chemical formula 1.

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

When the compound according to one embodiment of the present specification contains a triarylmethane dye monomer; a (meth) acrylic acid monomer; and a structure represented by the above chemical formula 1, heat resistance and chemical resistance can be improved. Specifically, when the structure represented by the chemical formula 1 is introduced into the triarylmethane dye, the structure represented by the chemical formula 1 promotes a radical reaction and is colored as the exposure process proceeds. The bond between the binder resin, the compound, and the polyfunctional monomer in the agent composition is more activated than when the structure represented by the chemical formula 1 is not introduced, the degree of curing of the film is increased, and heat resistance is increased. And chemical resistance is improved.

Specifically, the structure represented by the chemical formula 1 is preferably, but is not limited to, a BPMA (benzophenone monomer) monomer.

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

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

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 the number of carbon atoms of the alkyl group may be 1 to 30. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group and n-heptyl group. There are, but are not limited to, n-octyl groups.

In the present specification, the cycloalkyl group is not particularly limited, but one having 3 to 30 carbon atoms is preferable, and a cyclopentyl group and a cyclohexyl group are particularly preferable, but the cycloalkyl group is not limited thereto.

As used herein, an alkylene group means an alkane having two bonding positions. As for the alkane, the above-mentioned description regarding the alkyl group is applied. 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 may be, for example, 1 to 30 carbon atoms. Further, the number of carbon atoms may be 1 to 20, or the number of carbon atoms may be 1 to 10.

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

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

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

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

As used herein, the term "aryl" in the "triarylmethane dye" is applicable to the description of the aryl group and / or the description of the heterocyclic group.

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

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

As used herein, the anionic group has a chemical bond with the triarylmethane dye monomer, and the chemical bond can mean an ionic bond. The anionic group is not particularly limited, and for example, US Pat. No. 7,939,644, JP-A-2006-003080, JP-A-2006-001917, JP-A-2005-159926, JP-A-2007-70288897. , JP-A-2005-071680, Korean Application Publication No. 2007-70000693, JP-A-2005-111696, JP-A-2008-249663, JP-A-2014-199436 can be applied.

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

As used herein, anionic groups can have anions 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.

As used herein, the term "(meth) acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The notation "(meth) acrylic acid" has the same meaning.

As used herein, (meth) acrylic acid or (meth) acrylic acid may be represented by methacrylic acid.

One embodiment of the present specification provides a compound comprising a triarylmethane dye monomer; a (meth) acrylic acid monomer; and a structure represented by the following chemical formula 1.

[Chemical formula 1]

は、他のモノマーまたは結合部に連結される部分を意味し、
Ｘ'は、ＯまたはＮＨであり、
Ｌ１およびＬ２は、互いに同一または異なり、それぞれ独立して、直接結合；置換もしくは非置換のアルキレン基；−Ｃ（＝Ｏ）−；または−Ｌ３−Ｏ（Ｃ＝Ｏ）−であり、
Ｌ３は、置換もしくは非置換のアルキレン基であり、
Ｒ１〜Ｒ３は、互いに同一または異なり、それぞれ独立して、水素；ヒドロキシ基；置換もしくは非置換のアルキル基であり、
ｒ２は、０〜４の整数であり、ｒ２が２以上の場合、Ｒ２は、互いに同一または異なり、
ｒ３は、０〜５の整数であり、ｒ３が２以上の場合、Ｒ３は、互いに同一または異なる。 In the chemical formula 1,

Means the part that is linked to another monomer or bond,
X'is O or NH,
L1 and L2 are the same or different from each other and are independently bonded; substituted or unsubstituted alkylene groups; -C (= O)-; or -L3-O (C = O)-.
L3 is a substituted or unsubstituted alkylene group.
R1 to R3 are hydrogen; hydroxy groups; substituted or unsubstituted alkyl groups, which are the same or different from each other and are independent of each other.
r2 is an integer from 0 to 4, and when r2 is 2 or more, R2 are the same or different from each other.
r3 is an integer from 0 to 5, and when r3 is 2 or more, R3 is the same as or different from each other.

In one embodiment of the specification, X'is O.

In one embodiment of the specification, X'is NH.

In one embodiment of the specification, L1 is a direct bond; a substituted or unsubstituted alkylene group; or −C (= O) −.

In one embodiment of the specification, L1 is a direct bond; a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms; or −C (= O) −.

In one embodiment of the specification, L1 is a direct bond; a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms; or −C (= O) −.

In one embodiment of the specification, L1 is a direct bond; a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; or −C (= O) −.

In one embodiment of the specification, L1 is a direct binding.

In one embodiment of the specification, L1 is a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; or a substituted or unsubstituted propylene group.

In one embodiment of the specification, L1 is a methylene group; an ethylene group; or a propylene group.

In one embodiment of the specification, L1 is −C (= O) −.

In one embodiment of the specification, L2 is a direct binding; -C (= O)-; or -L3-O (C = O)-.

In one embodiment of the specification, L2 is a direct binding.

In one embodiment of the specification, L2 is −C (= O) −.

In one embodiment of the specification, L2 is −L3-O (C = O) −.

In one embodiment of the specification, L3 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms.

In one embodiment of the specification, L3 is a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms.

In one embodiment of the specification, L3 is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms.

In one embodiment of the specification, L3 is a substituted or unsubstituted methylene group.

In one embodiment of the specification, L3 is a methylene group.

In one embodiment of the specification, R1 to R3 are hydrogen; hydroxy groups; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the present specification, R1 to R3 are hydrogen; hydroxy groups; substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the present specification, R1 to R3 are hydrogen; hydroxy groups; substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the specification, R1 to R3 are the same or different from each other and are independently hydrogen; hydroxy groups; substituted or unsubstituted methyl groups.

In one embodiment of the specification, R1 is hydrogen; or a methyl group.

In one embodiment of the specification, R2 is hydrogen.

In one embodiment of the specification, R3 is a methyl group substituted with a hydrogen; hydroxy group; or amine group.

According to one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-1.

[Chemical formula 1-1]

は、他のモノマーまたは結合部に連結される部分を意味し、
Ｘ'、Ｌ１、Ｌ２、Ｒ１〜Ｒ３、ｒ２およびｒ３は、前記化学式１で定義した通りである。 In the chemical formula 1-1

Means the part that is linked to another monomer or bond,
X', L1, L2, R1 to R3, r2 and r3 are as defined in the above chemical formula 1.

In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following structures, but is not limited thereto. The chemical formula 1 forms a portion to be polymerized from any one of the following structures.

In one embodiment of the present specification, the triarylmethane dye monomer provides a compound represented by the following chemical formula 2.

[Chemical formula 2]

［化学式Ａ−２］

［化学式Ａ−３］

前記化学式Ａ−１〜前記化学式Ａ−３において、

は、他のモノマーまたは結合部に連結される部分を意味し、

は、前記化学式２のＡに連結される部分を意味し、
Ｚは、ＮまたはＣＲであり、
前記Ｒは、水素；または置換もしくは非置換のアルキル基であり、
Ｒ４〜Ｒ６は、互いに同一または異なり、それぞれ独立して、水素；重水素；または置換もしくは非置換のアルキル基であり、
Ｒ１５およびＲ１６は、互いに同一または異なり、それぞれ独立して、水素；重水素；置換もしくは非置換のアルキル基；または置換もしくは非置換のアリール基であり、
Ｘは、陰イオン性基であり、
Ｘ３〜Ｘ６は、互いに同一または異なり、それぞれ独立して、水素；重水素；ハロゲン基；ヒドロキシ基；−ＣＯＯＨ；置換もしくは非置換のアルコキシ基；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
ｘ３は、０〜３の整数であり、ｘ３が２以上の場合、Ｘ３は、互いに同一または異なり、
ｘ４は、０〜１０の整数であり、ｘ４が２以上の場合、Ｘ４は、互いに同一または異なり、
ｘ５は、０〜４の整数であり、ｘ５が２以上の場合、Ｘ５は、互いに同一または異なり、
ｘ６は、０〜４の整数であり、ｘ６が２以上の場合、Ｘ６は、互いに同一または異なり、
Ｂは、置換もしくは非置換のアリール基；または置換もしくは非置換のアルキル基である。 In the chemical formula 2,
R11 to R14 are identical or different from each other and independently of each other, a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted alkoxy group. ,
X1 and X2 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; hydroxy group; -COOH; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkyl group. Cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.
x1 and x2 are integers from 0 to 4 and
When x1 is 2 or more, X1 are the same or different from each other.
When x2 is 2 or more, X2 are the same or different from each other.
A is represented by any one of the following chemical formulas A-1 to A-3.
[Chemical formula A-1]

[Chemical formula A-2]

[Chemical formula A-3]

In the chemical formulas A-1 to A-3,

Means the part that is linked to another monomer or bond,

Means the portion connected to A of the above chemical formula 2.
Z is N or CR
The R is hydrogen; or a substituted or unsubstituted alkyl group.
R4 to R6 are the same or different from each other and are independently hydrogen; deuterium; or substituted or unsubstituted alkyl groups.
R15 and R16 are the same or different from each other and are independently hydrogen; deuterium; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups.
X is an anionic group,
X3 to X6 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; hydroxy group; -COOH; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkyl group. Cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.
x3 is an integer from 0 to 3, and when x3 is 2 or more, x3 are the same or different from each other.
x4 is an integer from 0 to 10, and when x4 is 2 or more, x4 are the same or different from each other.
x5 is an integer from 0 to 4, and when x5 is 2 or more, x5 is the same as or different from each other.
x6 is an integer from 0 to 4, and when x6 is 2 or more, x6 are the same or different from each other.
B is a substituted or unsubstituted aryl group; or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R11 to R14 are the same or different from each other and are independently substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups.

In one embodiment of the present specification, R11 to R14 are identical or different from each other and are independent of each other and are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms; or substituted or unsubstituted having 6 to 30 carbon atoms. It is an aryl group.

In one embodiment of the present specification, R11 to R14 are identical or different from each other and are independent of each other and are substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; or substituted or unsubstituted having 6 to 20 carbon atoms. It is an aryl group.

In one embodiment of the present specification, R11 to R14 are identical or different from each other and are independent of each other and are substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms; or substituted or unsubstituted having 6 to 12 carbon atoms. It is an aryl group.

In one embodiment of the specification, R11 to R14 are the same or different from each other and independently of each other, a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; or a substitution. Alternatively, it is an unsubstituted phenyl group.

In one embodiment of the present specification, R11 to R14 are the same or different from each other, and independently of each other, methyl group; ethyl group; ethyl group substituted with alkoxy group; isopropyl group; n-propyl group; phenyl group; Alternatively, it is a phenyl group substituted with a methyl group.

In one embodiment of the specification, Z is N.

In one embodiment of the specification, Z is CR.

In one embodiment of the specification, R is a hydrogen; or a substituted or unsubstituted alkyl group.

In one embodiment of the specification, R is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the specification, R is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the specification, R is hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the specification, R is hydrogen.

In one embodiment of the specification, R4 to R6 are the same or different from each other and are independently hydrogen; deuterium; or substituted or unsubstituted alkyl groups.

In one embodiment of the specification, R4 to R6 are the same or different from each other and are independently hydrogen; deuterium; or substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms.

In one embodiment of the specification, R4 to R6 are hydrogen; deuterium; or substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the specification, R4 to R6 are the same or different from each other and are independently hydrogen; deuterium; or substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms.

In one embodiment of the specification, R4 to R6 are substituted or unsubstituted methyl groups.

In one embodiment of the specification, R4 to R6 are methyl groups.

In one embodiment of the specification, R15 and R16 are the same or different from each other and are independently hydrogen; deuterium; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups.

In one embodiment of the specification, R15 and R16 are the same or different from each other and independently of hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms; or 6 to 30 carbon atoms. It is a substituted or unsubstituted aryl group.

In one embodiment of the specification, R15 and R16 are the same or different from each other and independently of hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; or 6 to 20 carbon atoms. It is a substituted or unsubstituted aryl group.

In one embodiment of the specification, R15 and R16 are the same or different from each other and independently of hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms; or 6 to 12 carbon atoms. It is a substituted or unsubstituted aryl group.

In one embodiment of the specification, R15 is a substituted or unsubstituted ethyl group.

In one embodiment of the specification, R15 is an ethyl group.

In one embodiment of the specification, R16 is a substituted or unsubstituted phenyl group.

In one embodiment of the specification, R16 is a halogen group substituted or unsubstituted phenyl group.

In one embodiment of the specification, R16 is a fluorine-substituted or unsubstituted phenyl group.

In one embodiment of the specification, X may be a bistrifluolmethanesulfonimide anion.

In one embodiment of the specification, X1 and X2 are the same or different from each other and are independent of each other: hydrogen; heavy hydrogen; halogen group; hydroxy group; -COOH; substituted or unsubstituted alkoxy group; substituted or unsubstituted. Alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

In one embodiment of the specification, X1 and X2 are the same or different from each other and are independently hydrogen; halogen groups; or substituted or unsubstituted alkyl groups.

In one embodiment of the specification, X1 and X2 are hydrogen; halogen groups; or substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, which are the same or different from each other and are independent of each other.

In one embodiment of the specification, X1 and X2 are hydrogen; halogen groups; or substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the specification, X1 and X2 are hydrogen; halogen groups; or substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, which are the same or different from each other and are independent of each other.

In one embodiment of the specification, X1 and X2 are the same or different from each other and are independently hydrogen; halogen groups; or substituted or unsubstituted methyl groups.

In one embodiment of the specification, X1 and X2 are the same or different from each other and are independently hydrogen; fluorine; chlorine; or methyl groups.

In one embodiment of the specification, X3 to X6 are the same or different from each other and are independent of each other: hydrogen; heavy hydrogen; halogen group; hydroxy group; -COOH; substituted or unsubstituted alkoxy group; substituted or unsubstituted. Alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.

In one embodiment of the specification, X3 to X6 are hydrogen; -COOH; or substituted or unsubstituted alkyl groups that are identical or different from each other and are independent of each other.

In one embodiment of the specification, X3 to X6 are hydrogen; -COOH; or substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the specification, X3 to X6 are hydrogen; -COOH; or substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the specification, X3 to X6 are hydrogen; -COOH; or substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, which are the same as or different from each other and are independent of each other.

In one embodiment of the specification, X3 to X6 are the same or different from each other and are independently hydrogen; -COOH; or substituted or unsubstituted methyl groups.

In one embodiment of the specification, X3 to X6 are the same or different from each other and are independent hydrogen; -COOH; or methyl groups.

In one embodiment of the specification, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the specification, B is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the specification, B is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; or an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted.

In one embodiment of the specification, B is a substituted or unsubstituted phenyl group.

In one embodiment of the specification, B is a phenyl group.

In one embodiment of the present specification, the chemical formula 2 may be represented by any one of the following chemical formulas 2-1 to 2-3.

[Chemical formula 2-1]

[Chemical formula 2-2]

[Chemical formula 2-3]

In the chemical formulas 2-1 to 2-3.
R11 to R16, R4 to R6, X1 to X6, x1 to x6, Z, X and B are as defined in the above chemical formula 2.

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

[Chemical formula 2-1-1]

In the chemical formula 2-1-1,
R11 to R14, R4, X1 to X4, x1 to x4, Z and X are as defined in the above chemical formula 2.

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

[Chemical formula 2-2-1]

In the chemical formula 2-2-1
R11 to R14, R5, X1, X2, X5, x1, x2, x5, X and B are as defined in the above chemical formula 2.

In one embodiment of the present specification, the chemical formula 2-3 may be represented by the following chemical formula 2-3-1.

[Chemical formula 2-3-1]

In the chemical formula 2-3-1,
R11 to R16, R6, X1, X2, X6, x1, x2, x6 and X are as defined in the above chemical formula 2.

In one embodiment of the present specification, the chemical formula 2 may be represented by any one of the following structures, but is not limited thereto.

In the structure, X is as defined in Chemical Formula 2. Specifically, X is as defined by the chemical formulas A-1 to A-3.

In the present specification, the (meth) acrylic acid monomer may be represented by the following chemical formula B.

[Chemical formula B]

In the chemical formula B,
T1 is a hydrogen; -COOH; substituted or unsubstituted alkyl group; or a substituted or unsubstituted alkoxy group.
T2 is a hydrogen; or a substituted or unsubstituted alkyl group.
M is a direct bond; or a substituted or unsubstituted alkylene group.

In one embodiment of the specification, T1 is hydrogen; -COOH; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms.

In one embodiment of the specification, T1 is hydrogen; -COOH; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.

In one embodiment of the specification, T1 is hydrogen; -COOH; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms.

In one embodiment of the specification, T1 may be hydrogen; -COOH; or any one of the following structures:

In one embodiment of the present specification, the structure represented by the chemical formula B may be represented by any one of the following structures, but is not limited thereto.

One embodiment of the present specification is represented by the triarylmethane dye monomer 55 to 99% by weight; the (meth) acrylic acid monomer 1 to 30% by weight; and the chemical formula 1 based on the total weight of the compound. A compound containing 1 to 50% by weight of a structure is provided. One embodiment of the present specification is represented by the triarylmethane dye monomer 55 to 98% by weight; the (meth) acrylic acid monomer 1 to 30% by weight; and the chemical formula 1 based on the total weight of the compound. A compound containing 1 to 20% by weight of a structure is provided.

Preferably, it contains 70% by weight of the triarylmethane dye monomer; 20% by weight of the (meth) acrylic acid monomer; and 5% by weight of the structure represented by the chemical formula 1 based on the total weight of the compound.

The triarylmethane-based polymer dye may consist of a bond between the triarylmethane-based dye and another monomer. A sufficient color can be exhibited only when the content of the triarylmethane dye is 50% by weight or more, and an appropriate color can be exhibited with a small content when preferably 70% by weight or more.

In one embodiment of the present specification, the weight average molecular weight of the compound is 5,000 g / mol to 35,000 g / mol. It may be preferably from 15,000 g / mol to 30,000 g / mol.

When the compound satisfies the range of the weight average molecular weight, it can have an appropriate development time and heat resistance.

When the weight average molecular weight of the compound is less than 5,000 g / mol, the amount of the coloring material removed by the developing solution increases, and the color change due to heat becomes large. When the weight average molecular weight of the compound exceeds 35,000 g / mol, the developing time increases.

The weight average molecular weight is one of the average molecular weights in which the molecular weight is not uniform and the molecular weight of a certain polymer substance is used as a reference, and the molecular weights of the component molecular species of the polymer compound having a molecular weight distribution are averaged by weight. It is a value obtained by

The weight average molecular weight is measured by high performance liquid chromatography (HPLC) analysis.

In one embodiment of the present specification, the number average molecular weight of the compound may be 20 to 32. When the compound satisfies the range of the number average molecular weight, it can have an appropriate development time and heat resistance.

The number average molecular weight means an average molecular weight obtained by averaging the molecular weights of component molecular species of a polymer compound having a molecular weight distribution by a fractional fraction or a mole fraction.

The number average molecular weight is measured by high performance liquid chromatography (HPLC) analysis.

In one embodiment of the specification, the dispersity of the compound may be 2-3. Specifically, the dispersity may be 2.28 to 2.97.

The degree of dispersion is a polydispersity index (PDI; Poly Dispersity Index), which is expressed by dividing the value of the weight average molecular weight by the number average molecular weight.

In one embodiment of the specification, the compound can include one or more triarylmethane dye monomers.

In one embodiment of the present specification, the (meth) acrylic acid monomer may contain one or more (meth) acrylic acid monomers.

In one embodiment of the specification, the compound may further comprise a thermosetting monomer.

The thermosetting monomer may be, but is not limited to, glycidyl methacrylate, oxetane, or M-100.

The glycidyl methacrylate may be represented by the following structure.

The oxetane may be represented by the following structure.

The M-100 may be represented by the following structure.

In one embodiment of the specification, the compound may further comprise a styrene monomer, if desired.

One embodiment of the specification provides a colorant composition comprising said compound; binder resin; polyfunctional monomer; photoinitiator; and solvent.

In one embodiment of the specification, the colorant composition may further comprise one or more of pigments and dyes.

For example, the colorant 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 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; quinophthalone-based compounds; isoindone-based compounds; methine. (Methine) -based compounds; Phthalocyanine-based compounds; Metall phthalocyanine-based compounds; Porphyrin-based compounds; Metal porphyrin-based compounds; Tetraazaporphyrin-based compounds; Tetra azaporphyrin (metal terra aza porphyrin) -based compounds; cyanine-based compounds; Xanthene-based compounds; metal dipyrromethane-based compounds; boron dipyrrometen (boron dipyramine) -based compounds. One or more may be selected from the group consisting of a system compound; a diketopyrrolopyrol system compound; a triarylmethane system compound; and a perylene system compound.

Specifically, the pigment may be a phthalocyanine compound, or may be B15: 6, G7, G58, G59, or G36.

Specifically, the dye may be a xanthene-based compound, a metal-complex-based compound, or a quinophthalone-based compound.

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 colorant composition.

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

The polyfunctional monomer that imparts mechanical strength to the film 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 vinyl monomers include styrene, α-methylstyrene, (o, m, p) -vinyltoluene, (o, m, p) -methoxystyrene, and (o, m, p). ) -Choose from the group consisting of chlorostyrene, but is not limited to these.

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

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

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

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

In one embodiment of the specification, the polyfunctional monomer may be specifically dipentaerythritol hexaacrylate.

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 g / mol 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 is a copolymer resin (copolymer) of a monomer selected from the group consisting of methacrylic acid, glycidyl methacrylic acid, styrene, cyclohexyl methacrylate, and methacrylate. ) May be.

Specifically, the binder resin may be a copolymer in which methacrylic acid, glycidyl methacrylic acid, and styrene are 13, 52, and 35% by weight, respectively, based on the total weight of the copolymer. ..

Further, the binder resin may contain 45, 30 and 25% by weight of cyclohexyl methacrylate, methacrylate and methacrylic acid, respectively, based on the total weight of the copolymer.

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

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

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

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

The oxime compounds include 1,2-octadion-1- (4-phenylthio) phenyl-2- (o-benzoyloxime) (Ciba Geigy, CGI124) and ethanone-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, but is not limited to, SPI-03.

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 methyl ether acetate, propylene glycol ethyl One or more selected from the group consisting of ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether. There may be, but it is not limited to this.

Specifically, the solvent may be propylene glycol monomethyl ether acetate or diacetone alcohol.

In one embodiment of the present specification, the content of the compound is 1 to 50% by weight; the content of the binder resin is 5 to 40% by weight; the polyfunctionality is based on the total weight of the colorant composition. Provided are colorant compositions in which the content of the monomer is 5-40% by weight; the content of the photoinitiator is 1-10% by weight; and the content of the solvent is 30-80% by weight.

In one embodiment of the present specification, the content of the compound is 1 to 50% by weight and the content of the binder resin is 5 to 40% by weight based on the total weight of the solid content in the colorant composition. %, The content of the polyfunctional monomer is 5 to 40% by weight, and the content of the photoinitiator is 1 to 10% by weight.

When each component contained in the colorant composition satisfies the above range, the compound, the binder resin, and the polyfunctional monomer in the colorant composition can be bonded to each other by radical polymerization to form a hard film. ..

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

According to one embodiment of the specification, the colorant composition may further comprise one or more selected from the group consisting of leveling agents, antioxidants, adhesion aids, and surfactants.

According to one embodiment of the specification, the colorant composition may further comprise an antioxidant.

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

According to one embodiment of the present specification, the colorant composition is a photocrosslinking / reducing agent, a curing accelerator, an adhesion aid, an adhesion accelerator, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, a dispersant. , And one or more additives selected from the group consisting of leveling agents.

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

The photocrosslinking agents include benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3,3. Benzophenone compounds such as −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-phenylacrine, 1,7-bis (9) Acrydin compounds such as −acridinyl) heptane, 1,5-bis (9-acridinylpentane), 1,3-bis (9-acridinyl) propane; benzyl, 1,7,7-trimethyl-bicyclo [2, 2,1] Dicarbonyl compounds such as heptane-2,3-dione, 9,10-phenanthrenquinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4 Phosphine oxide compounds such as 4-trimethylpentylphosphine oxide; benzoates such as methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate System 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-Thiadiazole, 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.

As the adhesion accelerator used in the present specification, one or more of metaacryloylsilane coupling agents such as metaacryloyloxypropyltrimethoxysilane, metaacryloyloxypropyldimethoxysilane, and metaacryloyloxypropyltriethoxysilane are used. It can be selected and used, and as the alkyltrimethoxysilane, one or more kinds can be selected and used from octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like.

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

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

Specific examples of the antioxidants include phosphate-based heat stabilizers such as phosphoric acid, trimethyl phosphate, or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-). Hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2 , 4,6-Tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4) -Methyl-6-t-butylphenol), 2,6-g, t-butylphenol, 4,4'-butylidene-bis (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl) -6-t-butylphenol) or bis [3,3-bis- (4'-hydroxy-3'-tart-butylphenyl) butanoic acid] glycol ester (Bis [3,3-bis- (4'-hydroxy) -3'-tert-butylphenyl) butanoicacid] glycol ester) -based primary antioxidants; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N, N'-diphenyl-p -Amine-based secondary antioxidants such as phenylenediamine or N, N'-di-β-naphthyl-p-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercapto Thio-based secondary antioxidants such as benzothiazole, 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) Phenollythritol Diphosphite), or (1,1'-biphenyl) -4,4'-diylbisphosphonasate tetrakis [ 2,4-Bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous Examples thereof include phosphite-based secondary antioxidants such as acid tetrakis [2,4-bis (1,1-dimethylyl) phenyl] ester).

Specifically, as the antioxidant, Songnox 1010 can be used, but the antioxidant is not limited thereto.

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, and 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 polymer-based 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-containing. And, but not limited to, all commonly used in the art can be used, including, but not limited to, non-polymer nitrogen-containing compounds.

Specifically, the leveling agent may be F-554, but is not limited thereto.

KBM-503 can be used as the adhesive aid, but the adhesive is not limited to this, and all commonly used adhesives in the art can be used.

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

More specifically, the colorant composition of the present specification is applied onto the substrate by an appropriate method to form a thin film or photosensitive material in the form of 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 colorant composition according to the present specification include a mercury vapor arc (arc), a carbon arc, and an Xe arc that emit light having a wavelength of 250 nm to 450 nm. Not exclusively.

The colorant composition according to the present specification includes a pigment-dispersed photosensitive material for manufacturing a thin film liquid crystal display (TFT LCD) color filter, a photosensitive material for forming a black matrix of a thin film liquid crystal display (TFT LCD) or an organic light emitting diode, and an overcoat. Used for coating 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. 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 colorant composition containing the triarylmethane dye monomer; (meth) acrylic acid monomer; and a compound containing a structure represented by the following chemical formula 1. A color filter can be formed by applying the colorant composition onto a substrate to form a coating film, and exposing, developing, and curing the coating film.

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

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

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

A grid-like black pattern called a black matrix can be arranged between the color pixels of the color filter for the purpose of improving contrast. Chromium can be used as the material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used. However, in consideration of high cost in the process, high reflectance of chromium, and environmental pollution by chromium waste liquid, a resin black matrix 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 it is not construed that the scope of the present specification is 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.

<Example>

<Example of compound synthesis>

1. 1. Synthesis of intermediate compounds

(1) Synthesis of compound of Chemical Formula 1-1

To 0.220 mol (53 g, 1 eq) of N- (4-hydroxycyclohexyl) -1-naphthylamine and 0.242 mol (1.1 eq) of triethylamine, 50 mL of dichloromethane was added and dissolved by stirring. Then, 0.242 mol (20.8 g, 1.1 eq) of methacrylic anhydride was added, and the temperature was raised to 40 ° C. for maintenance. After stirring for about 6 hours, distilled water was added to separate the organic layer. After adding 20 mL of saturated sodium chloride solution and stirring, the mixture was stirred for 30 minutes. After the layer separation, the organic layer was dried under reduced pressure and purified to obtain a chemical formula 1-1 0.17 mol, 53 g (yield 77%).

(2) Production of compound of Chemical Formula 1-2

Similar to Chemical Formula 1-1, using 4- (isoquinolin-5-ylamino) cyclohexane-1-ol 0.220 mol (53 g, 1 eq) and methacrylic anhydride 0.242 mol (20.8 g, 1.1 eq). The compound of Chemical Formula 1-2 was produced by the method to obtain 0.15 mol, 46.5 g (yield 68%) of the compound.

Ionization mode: APCI +: m / z = 308 [M + H] +, Exact Mass: 308

(3) Production of compounds of Chemical Formula 1-3

Under a nitrogen atmosphere, 0.06 mol (15 g, 1 eq) of 4,4-difluorobenzophenone and 0.29 mol (40 g, 5 eq) of N-isopropylaniline were placed in a flask, and the mixture was stirred at room temperature for about 48 hours. After completion of the reaction, distilled water was added and 50 mL of saturated sodium chloride solution was added to separate the organic layer. After layer separation, the organic layer was dried under reduced pressure and purified by column chromatography (methylene chloride: methanol = 15: 1) to obtain Chemical Formula 1-3 15 g (0.03 mol). (Yield 50%)

Ionization mode: APCI +: m / z = 448 [M + H] +, Exact Mass: 448

(4) Production of compounds of Chemical Formula 1-4

To 100 g of toluene, 0.249 mol (48 g, 1 eq) of N, N-diethylaminobenzoic acid was added and stirred. Then, 0.4 mol (47 g, 1.6 eq) of thionyl chloride was added dropwise, the temperature was raised to 80 ° C., and then the reaction was carried out for 1 hour. After the reaction, the mixture was distilled under reduced pressure to remove thionyl chloride and toluene to obtain N, N-diethylaminobenzoyl chloride. 0.31 mmol (0.04 g) of anhydrous aluminum chloride and 120 g of dichloroethane are stirred, cooled and maintained at 5 ° C. or lower. The N, N-diethylaminobenzoyl chloride obtained above was dissolved in 120 g of dichloroethane, added dropwise, and then stirred for 30 minutes. 0.249 mol (40.6 g) of N, N-diethylmetatoluidine was added dropwise to the reaction mixture, and the mixture was stirred at room temperature for 4 hours. After the reaction is completed by adding ice water, a sodium hydroxide solution is added to bring the pH to 11 or higher, and then filtration is performed with diatomaceous earth to remove insoluble matter. The organic layer obtained by layer separation was concentrated under reduced pressure and purified by column chromatography (dichloromethane: methanol = 10: 1) to obtain chemical formula 1-4 0.075 mol (25.4 g). (Yield 30%)

Ionization mode: APCI +: m / z = 338 [M + H] +, Exact Mass: 338

(5) Production of compound of Chemical Formula 1-5

0.03 mol (13.4 g, 1 eq) of the compound of Chemical Formula 1-3 was added to 140 g of chloroform and stirred. Then, 0.045 mol (6.9 g, 1.5 eq) of phosphorus oxychloride was added, and the mixture was stirred for about 15 minutes. 0.001 mol of 4-Methoxyxy phenyl and chemical formula 1-1 0.03 mol (9.3 g, 1 eq) were added, the temperature was raised to 60 ° C., and the mixture was refluxed for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, distilled water was added, and the mixture was stirred. After layer separation, the compound obtained by proceeding with concentration under reduced pressure was purified by column chromatography (methylene chloride: methanol: ethyl acetate = 6: 1: 2), and the chemical formula was 1-5 0.025 mol, 19.4 g (19.4 g). The yield was 83%).

Ionization mode: APCI +: m / z = 740 [M + H] +, Exact Mass: 740

(6) Production of compound of Chemical Formula 1-6

Chemical formula 1-3 0.03 mol (13.4 g, 1 eq) and chemical formula 1-2 0.03 mol (9.3 g, 1 eq) are added. -6 0.02 mol, 15.5 g (yield 66.7%) was obtained.

Ionization mode: APCI +: m / z = 741 [M + H] +, Exact Mass: 741

(7) Production of compound of Chemical Formula 1-7

Chemical formula 1-4 0.03 mol (10.1 g, 1 eq) and chemical formula 1-1 0.03 mol (9.3 g, 1 eq) are added. -7 0.023 mol, 15.3 g (yield 76.7%) was obtained.

Ionization mode: APCI +: m / z = 630 [M + H] +, Exact Mass: 630

2. Synthesis of triarylmethane blue dye compounds

(1) Synthesis example 1: Synthesis of chemical formula I

After dissolving 0.01 mol (7.8 g) of the compound of Chemical Formula 1-5 in 50 g of MeOH, 0.011 mol of lithium bistrifluolmethanesulfonimide was added in a 20% aqueous solution to replace the salt. After filtration, the obtained compound was dissolved in chloroform, washed with water and concentrated under reduced pressure to obtain 9.2 g (yield 90%) of Chemical Formula I 0.009 mol.

Ionization mode: APCI +: m / z = 740 [M + H] +, Exact Mass: 740

(2) Synthesis example 2: Synthesis of Chemical Formula II

A compound of Chemical Formula 1-6 (0.01 mol, 7.7 g) was added, and the mixture was produced in the same manner as in Synthesis Example 1 to obtain Chemical Formula II 0.008 mol, 10.2 g (yield 80%).

Ionization mode: APCI +: m / z = 741 [M + H] +, Exact Mass: 741

(3) Synthesis Example 3: Synthesis of Chemical Formula III

A compound of Chemical Formula 1-7 (0.01 mol, 6.7 g) was added, and the mixture was produced in the same manner as in Synthesis Example 1 to obtain Chemical Formula III (0.0082 mol, 7.5 g (yield 82%)).

Ionization mode: APCI +: m / z = 630 [M + H] +, Exact Mass: 630

3. 3. Synthesis of triarylmethane polymer compounds

(Synthesis Example 1) Synthesis of Compound A

A 50 mL flask is provided with a reflux cooling device, and benzophenone methacrylate represented by the structure of Chemical Formula A-1, methacrylic acid, and a dye represented by Chemical Formula I are prepared in a nitrogen atmosphere based on the total weight of the compound to be produced. After adding 5, 20 and 75% by weight, respectively, the mixture was mixed with a mixed solution of the solvent propylene glycol monomethyl ether acetate and diacetone alcohol 1: 1 and the temperature was raised to 60 ° C. Then, 10 parts by weight of the thermal polymerization initiator V-65 (2,2-Azobis (2,4-dimethylvalerontile)) was added based on the total weight of the polymer, and the mixture was refluxed for 16 hours to complete the polymerization reaction. A triarylmethane dye polymer compound A having a number average molecular weight of 26,546 and a dispersity of 2.57 was obtained.

(Synthesis Example 2) Synthesis of Compound B

After adding 10, 15, and 75% by weight of the benzophenone methacrylate represented by the structure of the chemical formula A-1, the methacrylic acid, and the dye represented by the chemical formula I based on the total weight of the produced compound, respectively. A dye polymer compound B having a number average molecular weight of 20,911 and a dispersity of 2.35 was obtained by the same method as in Synthesis Example 1.

(Synthesis Example 3) Synthesis of Compound C

Benzoylphenylmethacrylamide represented by the structure of Chemical Formula A-2, methacrylic acid, and the dye represented by Chemical Formula I were added in an amount of 5, 20 and 75% by weight, respectively, based on the total weight of the compound to be produced. After that, it was produced by the same method as in Synthesis Example 1 to obtain a triarylmethane dye polymer compound C having a number average molecular weight of 22,350 and a dispersity of 2.28.

(Synthesis Example 4) Synthesis of Compound D

After adding 5, 20 and 75% by weight of the benzophenone methacrylate represented by the structure of Chemical Formula A-1, the methacrylic acid and the dye represented by Chemical Formula II based on the total weight of the compound to be produced, respectively. The dye polymer compound D having a number average molecular weight of 26,879 and a dispersity of 2.69 was obtained by the same method as in Synthesis Example 1.

(Synthesis Example 5) Synthesis of Compound E

After adding 5, 20, 75% by weight of the benzophenone methacrylate represented by the structure of Chemical Formula A-1, the methacrylic acid, and the dye represented by Chemical Formula III based on the total weight of the compound to be produced, respectively. A dye polymer compound E having a number average molecular weight of 24,369 and a dispersity of 2.55 was obtained by the same method as in Synthesis Example 1.

(Synthesis Example 6) Synthesis of Compound F

Benzoylphenylmethacrylamide represented by the structure of Chemical Formula A-2, methacrylic acid, and the dye represented by Chemical Formula II were added in an amount of 10, 25, and 65% by weight, respectively, based on the total weight of the compound to be produced. After that, it was produced by the same method as in Synthesis Example 1 to obtain a triarylmethane dye polymer compound F having a number average molecular weight of 31,250 and a dispersion degree of 2.97.

(Synthesis Example 7) Synthesis of Compound G

After adding 15, 25, 55% by weight of the benzophenone methacrylate represented by the structure of Chemical Formula A-1, the methacrylic acid, and the dye represented by Chemical Formula III based on the total weight of the compound to be produced, respectively. A triarylmethane dye polymer compound G having a number average molecular weight of 30,956 and a dispersity of 2.88 was obtained by the same method as in Synthesis Example 1.

(Synthesis Example 8) Synthesis of Compound H

Benzophenone methacrylate, methacrylic acid, styrene, and dyes represented by Chemical Formula II having the structure of Chemical Formula A-1 are 5, 15, 15, and 70% by weight, respectively, based on the total weight of the compounds produced. After the addition, it was produced in the same manner as in Synthesis Example 1 to obtain a dye polymer compound H having a number average molecular weight of 21,287 and a dispersion degree of 2.39.

(Synthesis Example 9) Synthesis of Compound I

Benzophenone methacrylate, methacrylic acid, styrene, glycidyl methacrylate, which are represented by the structure of Chemical Formula A-1, and dyes, which are represented by Chemical Formula I, are used as 5, 15, 10, and 5, respectively, based on the total weight of the compounds produced. After adding 5, 70% by weight, it was produced in the same manner as in Synthesis Example 1 to obtain a dye polymer compound I having a number average molecular weight of 30.257 and a dispersion degree of 2.89.

(Synthesis Example 10) Synthesis of Compound J

Metaacrylic acid, styrene, glycidyl methacrylate, and the dye represented by Chemical Formula I were added in an amount of 15, 10, 15, and 60% by weight, respectively, based on the total weight of the compound to be produced, and then the same as in Synthesis Example 1. The dye polymer compound J having a number average molecular weight of 28,775 and a dispersity of 2.92 was obtained by the method.

(Synthesis Example 11) Synthesis of compound K

Metaacrylic acid and the dye represented by Chemical Formula I were added in an amount of 25 and 75% by weight, respectively, based on the total weight of the compound to be produced, and then produced by the same method as in Synthesis Example 1 to have a number average molecular weight. A dye polymer compound K having 21,584 and a dispersity of 2.21 was obtained.

The degree of dispersion is a polydispersity index (PDI; Poly Dispersity Index), and is represented by a value obtained by dividing a value of weight average molecular weight by a number average molecular weight. The weight average molecular weight and the number average molecular weight were measured by high performance liquid chromatography (HPLC) analysis.

[Production of Example 1 of Colorant Composition]

Based on 100 parts by weight of the total weight of the colorant composition, 24.32 parts by weight of the compound A, 5.86 parts by weight of the binder resin A, 17.88 parts by weight of the binder resin B, and the polyfunctional monomer dipentaerythritol hexaacrylate. 13.28 parts by weight, leveling agent F-554 0.6 parts by weight, adhesion aid KBM-503 0.07 parts by weight, phenolic antioxidant Songnox 1010 0.88 parts by weight, photoinitiator SPI-03 0.87 Example 1 was produced by mixing 22.87 parts by weight of the solvent propylene glycol monomethyl ether acetate and 13.37 parts by weight of diacetone alcohol.

The binder resin A is a copolymer having contents of methacrylic acid, glycidyl methacrylic acid, and styrene of 13, 52, and 35% by weight, respectively, based on the total weight of the binder resin A.

The binder resin B is a copolymer in which the contents of cyclohexyl methacrylate, methacrylate, and methacrylic acid are 45, 30, and 25% by weight, respectively, based on the total weight of the binder resin B.

[Production of Examples 2 to 8 of Colorant Composition]

Examples 2 to the colorant composition in the same manner as in Example 1 of the colorant composition, except that compound A of Example 1 of the colorant composition was applied to each of the compounds listed in Table 1 below. 8 was manufactured.

[Production of Comparative Example 1 of Colorant Composition]

Comparative Example 1 of the colorant composition was produced in the same manner as in Example 1 of the colorant composition, except that compound A was changed to compound J in Example 1 of the colorant composition.

[Production of Comparative Example 2 of Colorant Composition]

Comparative Example 2 of the colorant composition was produced in the same manner as in Example 1 of the colorant composition, except that compound A was changed to compound K in Example 1 of the colorant composition.

[Production of Comparative Example 3 of Colorant Composition]

The same applies in Comparative Example 2 of the colorant composition, except that the content of the initiator SPI-03 was changed to 0.77 parts by weight and 0.10 parts by weight of the benzophenone methacrylate represented by the structure of Chemical Formula A-1. Comparative Example 3 of the colorant composition was produced by the method of.

[Production of Comparative Example 4 of Colorant Composition]

In Comparative Example 2 of the colorant composition, except that the content of the initiator SPI-03 was changed to 0.77 parts by weight and 0.10 parts by weight of benzoylphenylmethacrylamide represented by the structure of Chemical Formula A-2. , And Comparative Example 4 of the colorant composition was produced by the same method.

Experimental example

[Preparation of substrate]

The colorant compositions produced in Examples 1 to 8 and Comparative Examples 1 to 4 are spin-coated on glass (5 cm × 5 cm) and preheated (Prebake) at 105 ° C. for 70 seconds to form a film. rice field. ^{The film was exposed to an energy of 40 mJ / cm 2} under a high-pressure mercury lamp using a photomask, and then the pattern was developed with a KOH alkaline aqueous solution and washed with distilled water. After removing the distilled water, a post-heat treatment (Postbake) was performed at 240 ° C. for 20 minutes to obtain a color pattern.

[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 (Postbake 1 time) substrate prepared under the above conditions.

Further, the post-heat treatment substrate (Postbake once) was additionally treated at 240 ° C. for 60 minutes to obtain a transmittance spectrum in the same measurement range with the same apparatus.

Using the values L *, a *, and b * obtained from the absorption spectrum obtained with the C light source as the backlight, "ΔEab (heat resistance)" was calculated by the following formula 1 and shown in Table 2 below. Indicated.

[Calculation formula 1]

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

When the ΔEab (heat resistance) value is small, it means that there is little color change, and it means that the heat resistance is excellent.

[Chemical resistance evaluation]

After cutting the substrate that had been subjected to one post-heat treatment to 1 cm × 5 cm, the absorption spectrum in the wavelength range of 380 to 780 nm was measured using a spectroscope (MCPD, Otsuka Co., Ltd.).

After obtaining the spectrum, it was immersed in 16 g of N-methyl-2-pyrrolidone solvent, left at room temperature for 10 minutes, and then washed thoroughly with distilled water. A transmittance spectrum was obtained in the same device and in the same measurement range.

The calculation formula 1 was applied to the spectra before and after immersion, and "ΔEab (chemical resistance)" was shown in Table 2 below. A small Eab (chemical resistance) value means that there is little color change, and it means that the chemical resistance is excellent.

According to Table 2, the ΔEab (heat resistance) and ΔEab (chemical resistance) values of Examples 1 to 8 are smaller than those of Comparative Examples 1 to 4, and therefore, according to one embodiment of the present specification. It was confirmed that it is possible to obtain a colorant composition and a color filter having excellent heat resistance and chemical resistance by using such a compound.

Claims (12)

Triarylmethane dye monomer;
(Met) Acrylic acid monomer; and a compound containing a structure represented by the following chemical formula 1:
[Chemical formula 1]

In the chemical formula 1,

Means the part that is linked to another monomer or bond,
X'is O or NH,
L1 and L2 are the same or different from each other and are independently bonded; substituted or unsubstituted alkylene groups; -C (= O)-; or -L3-O (C = O)-.
L3 is a substituted or unsubstituted alkylene group.
R1 to R3 are hydrogen; hydroxy groups; substituted or unsubstituted alkyl groups, which are the same or different from each other and are independent of each other.
r2 is an integer from 0 to 4, and when r2 is 2 or more, R2 are the same or different from each other.
r3 is an integer from 0 to 5, and when r3 is 2 or more, R3 is the same as or different from each other. The triarylmethane dye monomer is represented by the following chemical formula 2.
The compound according to claim 1:
[Chemical formula 2]

In the chemical formula 2,
R11 to R14 are identical or different from each other and independently of each other, a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted alkoxy group. ,
X1 and X2 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; hydroxy group; -COOH; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkyl group. Cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.
x1 and x2 are integers from 0 to 4 and
When x1 is 2 or more, X1 are the same or different from each other.
When x2 is 2 or more, X2 are the same or different from each other.
A is represented by any one of the following chemical formulas A-1 to A-3.
[Chemical formula A-1]

[Chemical formula A-2]

[Chemical formula A-3]

In the chemical formulas A-1 to A-3,

Means the part that is linked to another monomer or bond,

Means the portion connected to A of the above chemical formula 2.
Z is N or CR
The R is hydrogen; or a substituted or unsubstituted alkyl group.
R4 to R6 are the same or different from each other and are independently hydrogen; deuterium; or substituted or unsubstituted alkyl groups.
R15 and R16 are the same or different from each other and are independently hydrogen; deuterium; substituted or unsubstituted alkyl groups; or substituted or unsubstituted aryl groups.
X is an anionic group,
X3 to X6 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; hydroxy group; -COOH; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkyl group. Cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group.
x3 is an integer from 0 to 3, and when x3 is 2 or more, x3 are the same or different from each other.
x4 is an integer from 0 to 10, and when x4 is 2 or more, x4 are the same or different from each other.
x5 is an integer from 0 to 4, and when x5 is 2 or more, x5 is the same as or different from each other.
x6 is an integer from 0 to 4, and when x6 is 2 or more, x6 are the same or different from each other.
B is a substituted or unsubstituted aryl group; or a substituted or unsubstituted alkyl group. Based on the total weight of the compound
55-99% by weight of the triarylmethane dye monomer;
1 to 30% by weight of the (meth) acrylic acid monomer; and 1 to 50% by weight of the structure represented by the chemical formula 1.
Including,
The compound according to claim 1 or 2. The weight average molecular weight of the compound is 5,000 g / mol to 35,000 g / mol.
The compound according to any one of claims 1 to 3. The compound further comprises a thermosetting monomer.
The compound according to any one of claims 1 to 4. The compound according to any one of claims 1 to 5;
Binder resin;
Polyfunctional monomer;
A colorant composition comprising a photoinitiator; and a solvent. The colorant composition further comprises one or more of pigments and dyes.
The colorant composition according to claim 6. Based on the total weight of solids in the colorant composition,
The content of the compound is 1 to 50% by weight.
The content of the binder resin is 5 to 40% by weight.
The content of the polyfunctional monomer is 5 to 40% by weight, and the content is 5 to 40% by weight.
The content of the photoinitiator is 1-10% by weight.
The colorant composition according to claim 6 or 7. It further comprises one or more selected from the group consisting of leveling agents, antioxidants, adhesive aids, and surfactants.
The colorant composition according to any one of claims 6 to 8. A photosensitive material produced by using the colorant composition according to any one of claims 6 to 9. A color filter containing the photosensitive material according to claim 10. A display device including the color filter according to claim 11.