JP6915767B2 - Compounds, polymers, color material compositions, resin compositions, color filters and display devices - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0071745 filed with the Korean Intellectual Property Office on June 22, 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. 10-2019-0055682 filed with the Korean Intellectual Property Office on May 13, 2019, the entire contents of which are incorporated herein by reference.

The present specification relates to compounds, polymers, colorant compositions, resin compositions, color filters and display devices.

Recently, as a light source for a liquid crystal display (LCD), instead of the existing cold cathode fluorescent lamp (CCFL), a self-luminous LED (light emitting diode) or OLED (organic light emitting diode) element that is neither driven nor liquid crystal is often used. Has been done. When the LED or OLED is used as a light source, red, green, and blue light is emitted by itself, so that a separate color filter is not required. Therefore, in order to manufacture thin film displays, flexible displays, and the like, products that use self-luminous light as a unit pixel, such as LEDs and OLEDs from which color filters have been removed, have been developed and produced.

However, in the case of a display using LEDs and OLEDs as unit pixels, it is difficult to increase the area, and it is not possible to match or adjust the required color coordinates using the light emitted from the LED or OLED light source. Not easy. Therefore, in order to realize a desired hue, a light source and an appropriate color filter are required, and a pigment dispersion method using a pigment as a colorant is generally applied.

However, in the case of a pigment dispersion liquid, not only the pigment exists in a particle state and scatters light, but also the pigment surface area rapidly increases due to the miniaturization of the pigment, which deteriorates the dispersion stability and causes non-uniform pigment particles. Has the drawback of being generated.

Therefore, the use of dyes as colorants has been studied in order to achieve high brightness, high brightness ratio and high resolution. Among them, xanthene dyes are often used as red colorants. Generally, xanthene dyes have a good gradient slope and high absorbance in the range of 500 nm to 550 nm, and are effective for color characteristics, but pigments. It has the disadvantages of reduced chemical resistance and low heat resistance due to its higher solubility.

The present specification provides compounds, polymers, colorant compositions, resin compositions, color filters and display devices.

The present specification provides a compound represented by the following chemical formula 1.

[Chemical formula 1]

［化学式１−Ｂ］

前記化学式１−Ａおよび化学式１−Ｂにおいて、
前記Ｑ１およびＱ２は、互いに同一または異なり、それぞれ独立に、Ｏ；またはＮＨであり、
Ｌ１０１およびＬ１０２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アルキレン基；または置換もしくは非置換のアリーレン基であり、
Ｒ１０１〜Ｒ１０５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アルキル基；または置換もしくは非置換のシクロアルキル基であり、
Ｒ１０６は、下記の構造およびカルボン酸基（−ＣＯＯＨ）の中から選択されるいずれか１つであり、

前記構造において、
Ｌ２０１は、直接結合；またはＯであり、
Ｒ２０１〜Ｒ２０３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アルキル基；置換もしくは非置換のアルケニル基；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環基であり、
ｒ２０２は、１〜３の整数であり、
ｒ２０３は、１〜５の整数であり、
前記ｒ２０２が２以上の時、Ｒ２０２は、互いに同一または異なり、ｒ２０３が２以上の時、Ｒ２０３は、互いに同一または異なり、

は、連結される部位を意味し、
前記Ａｒ１およびＡｒ２のうちの少なくとも１つが前記化学式１−Ａで表される場合、前記Ｘ１およびＸ２のうちの少なくとも１つは、前記化学式１−Ｂで表され、
前記Ａｒ１およびＡｒ２のうちの少なくとも１つが前記化学式１−Ｂで表される場合、Ｘ１およびＸ２のうちの少なくとも１つは、前記化学式１−Ａで表される。 In the chemical formula 1,
L1 to L4 are the same or different from each other, and are independently bonded to each other; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group.
Ar1 and Ar2 are the same or different from each other and are independently hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or unsubstituted aryl group, or the following chemical formula. 1-A; or represented by the following chemical formula 1-B,
R1 to R3 are the same or different from each other, and independently of each other, hydrogen; deuterium; hydroxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or It is an unsubstituted heterocyclic group and
r1 and r2 are integers 1-3, respectively,
r3 is an integer of 1 to 4 and
When r1 is 2 or more, R1 is the same or different from each other, when r2 is 2 or more, R2 is the same or different from each other, and when r3 is 2 or more, R3 is the same or different from each other.
X1 and X2 are the same or different from each other and are represented by the following chemical formulas 1-A or 1-B, respectively.
[Chemical formula 1-A]

[Chemical formula 1-B]

In the chemical formulas 1-A and 1-B,
The Q1 and Q2 are the same or different from each other and are independently O; or NH.
L101 and L102 are the same or different from each other and are independently bonded; substituted or unsubstituted alkylene groups; or substituted or unsubstituted arylene groups, respectively.
R101 to R105 are the same or different from each other, and are independently hydrogen; deuterium; hydroxy group; substituted or unsubstituted alkyl group; or substituted or unsubstituted cycloalkyl group.
R106 is any one selected from the following structures and carboxylic acid groups (-COOH).

In the structure
L201 is a direct bond; or O,
R201 to R203 are the same or different from each other, and independently of each other, hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted hetero. It is a ring group
r202 is an integer from 1 to 3 and
r203 is an integer of 1 to 5 and
When r202 is 2 or more, R202 is the same or different from each other, and when r203 is 2 or more, R203 is the same or different from each other.

Means the part to be connected,
When at least one of the Ar1 and Ar2 is represented by the chemical formula 1-A, at least one of the X1 and X2 is represented by the chemical formula 1-B.
When at least one of Ar1 and Ar2 is represented by the chemical formula 1-B, at least one of X1 and X2 is represented by the chemical formula 1-A.

According to another embodiment of the present specification, a polymer containing the compound represented by the chemical formula 1 as a monomer is provided.

According to another embodiment of the present specification, there is provided a colorant composition containing the compound represented by the above chemical formula 1.

According to another embodiment of the present specification, there is provided a resin composition containing the colorant composition.

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

Further, according to one embodiment of the present specification, a display device including the color filter is provided.

The compound represented by Chemical Formula 1 according to one embodiment of the present specification has excellent solubility in a solvent, and has excellent heat resistance and chemical resistance.

Further, according to one embodiment of the present specification, the color material composition containing the compound represented by the chemical formula 1 has a characteristic of having higher brightness than the case where an existing pigment is used.

Further, according to one embodiment of the present specification, a color filter having excellent heat resistance and chemical resistance can be produced by using a color material composition containing the compound represented by the chemical formula 1.

Further, according to one embodiment of the present specification, when the coloring material composition containing the compound represented by the chemical formula 1 is used, it is not necessary to proceed with the dispersion step which is always necessary when applying the existing pigment. It has the effect of cost reduction.

Recently, as a light source for a liquid crystal display (LCD), instead of the existing cold cathode fluorescent lamp (CCFL), a self-luminous LED (light emitting diode) or OLED (organic light emitting diode) element that is neither driven nor liquid crystal is often used. Has been done. When the LED or OLED is used as a light source, red, green, and blue light is emitted by itself, so that a separate color filter is not required. Therefore, in order to manufacture thin film displays, flexible displays, and the like, products that use self-luminous light as a unit pixel, such as LEDs and OLEDs from which color filters have been removed, have been developed and produced.

However, in the case of a display using LEDs and OLEDs as unit pixels, it is difficult to increase the area, and it is not possible to match or adjust the required color coordinates using the light emitted from the LED or OLED light source. Not easy. Therefore, in order to realize a desired hue, a light source and an appropriate color filter are required, and a pigment dispersion method using a pigment as a colorant is generally applied.

However, in the case of a pigment dispersion liquid, not only the pigment exists in a particle state and scatters light, but also the pigment surface area rapidly increases due to the miniaturization of the pigment, which deteriorates the dispersion stability and causes non-uniform pigment particles. Has the drawback of being generated.

Therefore, the use of dyes as colorants has been studied in order to achieve high brightness, high brightness ratio and high resolution. Among them, xanthene dyes are often used as red colorants. Generally, xanthene dyes have a good gradient slope and high absorbance in the range of 500 nm to 550 nm, which is effective for color characteristics, but pigments. It has the disadvantages of reduced chemical resistance and low heat resistance due to its higher solubility.

However, the compound represented by the chemical formula 1 of the present specification not only improves heat resistance by containing an antioxidant, but also contains a crosslinkable group, which is a weak point of the dye, that is, dye transfer and elution. Has the effect of suppressing. Therefore, a color filter having excellent heat resistance and chemical resistance can be produced by using a color material composition containing the compound represented by the chemical formula 1 of the present specification.

Further, when the color material composition containing the compound represented by the chemical formula 1 of the present specification is used, it is not necessary to proceed with the dispersion step which is always necessary when applying the existing pigment, so that there is an effect of cost reduction.

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

The present specification provides the compound represented by the chemical formula 1.

When the xanthene dye represented by the chemical formula 1 has a reactive group represented by the substituent R106 of the chemical formula 1, the xanthene dyes can react with each other by radical or heat. Further, the xanthene dye represented by the chemical formula 1 can react with the polymerizable compound, the alkali-soluble resin and the like contained in the resin composition of the present specification. When the reaction occurs, the xanthene dye is firmly fixed in the cured film, resulting in improved heat resistance and chemical resistance.

In the present specification, examples of substituents will be described below, but the present invention is not limited thereto.

は、連結される部位を意味する。 In the present specification

Means the site to be connected.

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent, and the position to be substituted is the position where the hydrogen atom is substituted, that is, the substituent can be substituted. The position is not limited, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" refers to heavy hydrogen; halogen group; nitrile group; alkyl group; cycloalkyl group; amine group; silyl group; boron group; phosphine oxide group; aryl group; and N. , O, S, Se, and one or more substituents selected from the group consisting of heterocyclic groups containing one or more of the Si atoms, or 2 of the above exemplified substituents. It means that the above substituents are substituted with linked substituents or have no 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 1 to 50 is preferable, and 1 to 30 is more preferable. Further, it may be 1 to 20 or 1 to 10. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl. , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- There are, but are not limited to, propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but one having 3 to 60 carbon atoms is preferable, and 3 to 30 carbon atoms are more preferable. Further, it may be 3 to 20 or 3 to 10. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethyl. Cyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

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 40 are preferable, and those of 2 to 30 are more preferable. Further, it may be 2 to 20, 2 to 10. Specifically, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3- Butadienyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl, 2,2-Bis (diphenyl-1-yl) Vinyl-1-yl, stillbenyl group, styrenyl group and the like, but are not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but those having 6 to 50 carbon atoms are preferable, and 6 to 30 carbon atoms are more preferable. Further, it may be 6 to 20 or 6 to 12. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarter phenyl 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 50 carbon atoms are preferable, and 10 to 30 carbon atoms are more preferable. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a peryleneyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, or the like, but is limited thereto. It's not a thing.

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

In the present specification, the silyl group may be represented by the chemical formula of −SiY1Y2Y3, and Y1, Y2 and Y3 are hydrogen; substituted or unsubstituted alkyl group; or substituted or unsubstituted aryl group, respectively. May be good. Specifically, the silyl group includes a trimethylsilyl group (TMS), a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like. However, it is not limited to these.

In the present specification, the boron group may be represented by the chemical formula of −BY4Y5, and Y4 and Y5 may be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, respectively. .. Specific examples of the boron group include, but are not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

In the present specification, the heterocyclic group contains one or more of N, O, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 60. Those of 2 to 30 are preferable, and those of 2 to 30 are more preferable. Further, it may be 2 to 20. Examples of heterocyclic groups include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, pteridine group, pyridazine. Group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pteridine group, pyridopyrimidine group, pyridopyrimidine group, pyridopyrazine group, pyrazinenopyrazine group Group, indole group, pyrido indole group, indenopyrimidine (5H-indeno pyrimidine), carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group , Benzofuran group, dibenzofuran group, phenanthroline, thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group and the like, but are not limited thereto.

In the present specification, the heteroaryl group may be selected from the examples of the heterocyclic group except that it is aromatic, but is not limited thereto.

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

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

In one embodiment of the specification, L1 to L4 are the same or different from each other and are independently bonded; substituted or unsubstituted alkylene groups; or substituted or unsubstituted allylene groups.

In one embodiment of the specification, L1 to L4 are identical or different from each other and are independently bonded to each other; substituted or unsubstituted alkylene groups having 1 to 30 carbon atoms; or substituted or non-substituted with 6 to 30 carbon atoms. It is a substituted arylene group.

In one embodiment of the present specification, L1 to L4 are identical or different from each other and are independently bonded to each other; substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms; or substituted or non-substituted with 6 to 20 carbon atoms. It is a substituted arylene group.

In one embodiment of the specification, L1 to L4 are identical or different from each other and are independently bonded to each other; substituted or unsubstituted alkylene groups having 1 to 10 carbon atoms; or substituted or non-substituted with 6 to 12 carbon atoms. It is a substituted arylene group.

In one embodiment of the present specification, L1 to L4 are the same or different from each other and are independently bonded to each other; a substituted or unsubstituted methylene group; a substituted or unsubstituted ethylene group; or a substituted or unsubstituted propylene group. Is.

In one embodiment of the specification, L1 to L4 are the same or different from each other and are independently bonded; methylene group; ethylene group; or propylene group.

In one embodiment of the specification, L1 to L4 are direct bonds.

In one embodiment of the specification, Ar1 and Ar2 are identical or different from each other and independently of each other: hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or unsubstituted. It is an aryl group of, or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and independently, hydrogen; hydrocarbon; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or substituted with 3 to 30 carbon atoms, respectively. It is an unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and independently, hydrogen; hydrocarbon; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or substituted with 3 to 20 carbon atoms, respectively. It is an unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.

In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and independently, hydrogen; hydrocarbon; substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; substituted or substituted with 3 to 10 carbon atoms, respectively. It is an unsubstituted cycloalkyl group; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.

In one embodiment of the specification, Ar1 and Ar2 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 substituted or substituted. It is an unsubstituted phenyl group or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.

In one embodiment of the specification, Ar1 and Ar2 are the same or different from each other and are independent of each other, a methyl group substituted or unsubstituted with a phenyl group; an ethyl group; a propyl group substituted or unsubstituted with a hydroxy group; an isopropyl group. It is a phenyl group or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.

In one embodiment of the specification, Ar1 is a phenyl group-substituted or unsubstituted methyl group; an ethyl group; a hydroxy group-substituted ethyl group; a propyl group; an isopropyl group; or a phenyl group, or the following chemical formula. 1-A; or represented by the following chemical formula 1-B.

In one embodiment of the specification, Ar2 is a methyl group substituted or unsubstituted with a phenyl group; an ethyl group; a propyl group; an isopropyl group; or a phenyl group, or the following chemical formula 1-A; or the following chemical formula 1-. It is represented by B.

In one embodiment of the specification, Ar1 and Ar2 are methyl groups substituted with phenyl groups.

In one embodiment of the specification, R1 to R3 are the same or different from each other and independently of each other: hydrogen; heavy hydrogen; hydroxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or An unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R1 to R3 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; 3 to 30 carbon atoms. Substituent or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 to R3 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; hydroxy group; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; 3 to 20 carbon atoms. Substituent or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In one embodiment of the present specification, R1 to R3 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; hydroxy group; substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; 3 to 10 carbon atoms. Substituent or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group having 6 to 12 carbon atoms; or substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In one embodiment of the specification, R1 to R3 are hydrogen.

In one embodiment of the specification, r1 and r2 are integers 1-3, respectively, r3 is an integer 1-4, and when r1 is 2 or greater, R1 is the same or different from each other. When r2 is 2 or more, R2 is the same or different from each other, and when r3 is 2 or more, R3 is the same or different from each other.

In one embodiment of the specification, r1 is an integer of 1-3.

In one embodiment of the specification, r1 is 3.

In one embodiment of the specification, r2 is an integer of 1-3.

In one embodiment of the specification, r2 is 3.

In one embodiment of the specification, r3 is an integer of 1-4.

In one embodiment of the specification, r3 is 4.

In one embodiment of the specification, X1 and X2 are the same or different from each other and are represented by the following chemical formulas 1-A or 1-B, respectively.

[Chemical formula 1-A]

[Chemical formula 1-B]

In the chemical formulas 1-A and 1-B,
The Q1 and Q2 are the same or different from each other and are independently O; or NH.

In one embodiment of the specification, Q1 and Q2 are O, respectively.

In one embodiment of the specification, Q1 and Q2 are NH, respectively.

In one embodiment of the specification, L101 and L102 are the same or different from each other and are independently bonded; substituted or unsubstituted alkylene groups; or substituted or unsubstituted allylene groups, respectively.

In one embodiment of the specification, L101 and L102 are the same or different from each other and are independently bonded to each other; substituted or unsubstituted alkylene groups having 1 to 30 carbon atoms; or substituted or non-substituted with 6 to 30 carbon atoms. It is a substituted arylene group.

In one embodiment of the specification, L101 and L102 are the same or different from each other and are independently bonded to each other; substituted or unsubstituted alkylene groups having 1 to 20 carbon atoms; or substituted or non-substituted with 6 to 20 carbon atoms. It is a substituted arylene group.

In one embodiment of the specification, L101 and L102 are the same or different from each other and are independently bonded to each other; substituted or unsubstituted alkylene groups having 1 to 10 carbon atoms; or substituted or non-substituted with 6 to 12 carbon atoms. It is a substituted arylene group.

In one embodiment of the specification, L101 and L102 are the same or different from each other and are independently bonded; substituted or unsubstituted methylene groups; or substituted or unsubstituted ethylene groups, respectively.

In one embodiment of the specification, L101 and L102 are the same or different from each other and are independently bonded; methylene group; or ethylene group, respectively.

In one embodiment of the specification, R101 to R105 are the same or different from each other and are independently hydrogen; deuterium; hydroxy groups; substituted or unsubstituted alkyl groups; or substituted or unsubstituted cycloalkyl groups. ..

In one embodiment of the present specification, R101 to R105 are the same as or different from each other, and independently, hydrogen; deuterium; hydroxy group; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or 3 to 3 carbon atoms. 30 substituted or unsubstituted cycloalkyl groups.

In one embodiment of the present specification, R101 to R105 are the same as or different from each other, and independently, hydrogen; deuterium; hydroxy group; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or 3 to 3 carbon atoms. 20 substituted or unsubstituted cycloalkyl groups.

In one embodiment of the present specification, R101 to R105 are the same as or different from each other, and independently, hydrogen; deuterium; hydroxy group; substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or 3 to 10 carbon atoms. It is a 10-substituted or unsubstituted cycloalkyl group.

In one embodiment of the specification, R101 to R105 are the same or different from each other and are independently hydrogen; hydroxy groups; or substituted or unsubstituted tert-butyl groups.

In one embodiment of the specification, R101 to R105 are the same or different from each other and are independently hydrogen; hydroxy groups; or tert-butyl groups.

In one embodiment of the specification, R103 is a hydroxy group.

In one embodiment of the specification, R102 and R104 are the same or different from each other and are independently substituted or unsubstituted tert-butyl groups.

In one embodiment of the specification, R102 and R104 are tert-butyl groups.

In one embodiment of the specification, R106 is any one of the following structures and carboxylic acid groups (-COOH).

In the structure
L201 is a direct bond; or O.

In one embodiment of the specification, L201 is a direct binding.

In one embodiment of the specification, L201 is O.

In one embodiment of the specification, R201-R203 are the same or different from each other and independently of each other: hydrogen; dehydrogen; substituted or unsubstituted alkyl group; substituted or unsubstituted alkenyl group; substituted or unsubstituted aryl. Group; or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R201 to R203 are the same or different from each other, and independently, hydrogen; hydrocarbon; substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; substituted or substituted with 2 to 30 carbon atoms. An unsubstituted alkenyl group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R201 to R203 are the same or different from each other, and independently, hydrogen; hydrocarbon; substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; substituted or substituted with 2 to 20 carbon atoms. An unsubstituted alkenyl group; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In one embodiment of the present specification, R201 to R203 are the same or different from each other, and independently, hydrogen; hydrocarbon; substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; substituted or substituted with 2 to 10 carbon atoms. An unsubstituted alkenyl group; a substituted or unsubstituted aryl group having 6 to 12 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In one embodiment of the specification, R201-R203 are the same or different from each other and are independently hydrogen; substituted or unsubstituted methyl groups; or substituted or unsubstituted ethylene groups.

In one embodiment of the present specification, R201 to R203 are the same or different from each other and are independently hydrogen; methyl group; or ethylene group.

In one embodiment of the specification, R201 is an ethylene group substituted with a methyl group.

In one embodiment of the specification, R202 is hydrogen.

In one embodiment of the specification, R203 is hydrogen; or a methyl group.

In one embodiment of the present specification, r202 is an integer of 1 to 3, r203 is an integer of 1 to 5, and when r202 is 2 or more, R202 is the same as or different from each other, and r203 is 2. At the above times, R203 are the same as or different from each other.

In one embodiment of the present specification, when at least one of the Ar1 and Ar2 is represented by the chemical formula 1-A, at least one of the X1 and X2 is represented by the chemical formula 1-B. When at least one of the Ar1 and Ar2 is represented by the chemical formula 1-B, at least one of X1 and X2 is represented by the chemical formula 1-A.

In one embodiment of the specification, when the Ar1 is represented by the chemical formula 1-A, at least one of the X1 and X2 is represented by the chemical formula 1-B.

In one embodiment of the specification, when the Ar2 is represented by the chemical formula 1-B, at least one of the X1 and X2 is represented by the chemical formula 1-A.

In one embodiment of the specification, the Ar1 and Ar2 are identical or different from each other and independently, hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or unsubstituted. In the case of the aryl group of, at least one of the X1 and X2 is represented by the chemical formula 1-A, and the rest of the X1 and X2 not represented by the chemical formula 1-A is represented by the chemical formula 1-B. expressed.

In one embodiment of the specification, the Ar1 and Ar2 are identical or different from each other and independently, hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; or substituted or unsubstituted. In the case of the aryl group of, at least one of the X1 and X2 is represented by the chemical formula 1-B, and the rest of the X1 and X2 not represented by the chemical formula 1-B is represented by the chemical formula 1-A. expressed.

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

[Chemical formula 1-1]

In the chemical formula 1-1
L1 to L4, Ar1, Ar2, R1 to R3, r1 to r3, X1 and X2 are as defined in the above chemical formula 1.

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

[Chemical formula 2]

In the chemical formula 2,
The definitions for L1 to L4, Ar1, Ar2, R1 to R3, r1 to r3, Q1, Q2, L101, L102, and R101 to R106 are the same as those defined in Chemical Formula 1.

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

[Chemical formula 3]

In the chemical formula 3,
The definitions for L1 to L4, Ar1, Ar2, R1 to R3, r1 to r3, Q1, L101, and R101 to R105 are the same as those defined in Chemical Formula 1.

According to one example, in the chemical formula 3, at least one of Ar1 and Ar2 may be represented by the chemical formula 1-B.

In one embodiment of the present specification, the compound represented by the chemical formula 1 is any one selected from the following compounds.

One embodiment of the present specification provides a polymer containing the compound represented by the chemical formula 1 as a monomer.

The monomer means a substance that becomes a unit when a polymer compound is produced by a chemical reaction.

The polymer means a compound made by polymerizing the monomer, and means a polymer compound.

In one embodiment of the present specification, the polymer contains the compound represented by the chemical formula 1 as a monomer, and may further contain another monomer. For example, the monomer contained in the binder resin described below and / or the polyfunctional monomer described below may be further contained as a monomer.

In one embodiment of the present specification, the weight average molecular weight of the polymer containing the compound represented by Chemical Formula 1 as a monomer may be 5,000 g / mol to 30,000 g / mol.

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 can be measured by Gel Permeation Chromatography (GPC) analysis.

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

In one embodiment of the specification, the colorant composition further comprises at least one of a dye and a pigment.

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

According to one embodiment of the present specification, the dye is one or more dyes selected from a xanthene dye, a cyanine dye, an anthraquinone dye, and an azaporphyrin dye, and the pigment is a blue pigment or a purple pigment. Is.

The xanthene dye, cyanine dye, anthraquinone dye, and azaporphyrin dye are not particularly limited as long as they are used in the art.

The blue pigment is not limited as long as it is used in the art, and among them, a copper phthalocyanine-based blue pigment can be included. Examples of the copper phthalocyanine-based blue pigment include compounds classified as pigments in the Color Index (The Society of Dyers and Colorists Publishing). As a specific example, C.I. I. Blue pigments (Color Index Pigment Blue) 1, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60 and the like can be mentioned.

The purple pigment is not limited as long as it is used in the art, and is classified as a pigment in the Color Index (The Society of Dyers and Colorists Publishing). I. Examples include Color Index Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 and the like.

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

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

In one embodiment of the specification, the resin composition may further comprise an additive.

The additive may be any one selected from the group consisting of leveling agents; and adhesion aids.

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 resin composition.

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

The polyfunctional monomer that imparts mechanical strength to the film 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, o-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.

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 may be a copolymer having a mass ratio of benzyl methacrylate; N-phenylmaleimide; styrene; methacrylic acid = 55: 9: 11: 25.

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

In one embodiment of the specification, the polyfunctional monomer is dipentaerythritol hexaacrylate.

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-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 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 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, diacetone alcohol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate , Propropylene glycol ethyl 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 one or more types, but the present invention is not limited to this.

In one embodiment of the specification, the solvent may be diacetone alcohol.

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

The resin composition may further contain 0.01% by weight to 20% by weight of the leveling agent and 0.01% by weight to 20% by weight of the adhesion aid based on the total weight of the resin composition.

According to one embodiment of the present specification, the content of the compound represented by the chemical formula 1 is 0.5% by weight to 90% by weight based on the total weight of the solid content in the resin composition. The content of the binder resin is 1% by weight to 50% by weight, the content of the photoinitiator is 0.1% by weight to 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 in the resin composition. The weight% reference based on the solid content and the solid content of each component can be measured by common analytical means used in the art, such as liquid chromatography or gas chromatography.

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

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 resin composition.

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

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.

The photocrosslinked 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-phenanthrenquinone; 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,6-dimethoxybenzoyl) -2,4 , 4-trimethylpentylphosphine oxide and other phosphine oxide compounds; methyl-4- (dimethylamino) benzoate, ethyl-4- (dimethylamino) benzoate, 2-n-butoxyethyl-4- (dimethylamino) benzoate and the like. 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. ..

As the curing accelerator, it is used to enhance curing and mechanical strength, and specifically, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1, 3,4-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.

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

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

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

Specific examples of the antioxidant are phosphate-based heat stabilizers such as phosphoric acid, trimethyl phosphate, or triethyl phosphate; 2,6-di-t-butyl-p-cresol, octadecyl-3- (4-). Hydroxy-3,5-di-t-butylphenyl) propionate, tetrabis [methylene-3- (3,5-di-t-butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2 , 4,6-Tris (3,5-di-t-butyl-4-hydroxybenzyl) benzene, 3,5-di-t-butyl-4-hydroxybenzyl phosphite diethyl ester, 2,2-thiobis (4) -Methyl-6-t-butylphenol), 2,6-di-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-phenylenediamine; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionate, mercaptobenzo Thio-based secondary antioxidants such as thiazole, or tetramethylthiuram disulfide tetrabis [methylene-3- (laurylthio) propionate] methane; or triphenylphosphite, tris (nonylphenyl) phosphite, triisodecylphosphite, Bis (2,4-dibutylphenyl) pentaerythritol diphosphite (Bis (2,4-dibutylphenyl) Phenollythritol Diphosphite), or (1,1'-biphenyl) -4,4'-diylbisphosphonoate tetrakis [2] , 4-Bis (1,1-dimethylethyl) phenyl] ester ((1,1'-Biphenyl) -4,4'-Diylbisphosphonous aci Examples thereof include phosphite-based secondary antioxidants such as d tetrakis [2,4-bis (1,1-dimethyl) phenyl] ester).

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

Examples of the thermal polymerization inhibitor include p-anisole, hydroquinone, pyrocatechol, t-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.

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

In one embodiment of the present specification, the color filter can be produced by using a resin composition containing the color material composition.

In one embodiment of the present specification, the resin composition is applied onto a substrate to form a coating film, and the coating film is exposed, developed and cured to form a thin film or a photosensitive material in a pattern form. A color filter can be formed by including the photosensitive material.

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

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

The resin composition according to the present specification is 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 layer-forming photosensitive materials, column spacer photosensitive materials, photocurable paints, photocurable inks, photocurable adhesives, printing plates, photosensitive materials for printing wiring boards, photosensitive materials for plasma display panels (PDPs), etc. It can be used, and there are no particular restrictions on its use.

The resin composition according to one embodiment of the present specification has excellent heat resistance, little color change due to heat treatment, high color reproduction rate even during the manufacturing process of a color filter and a curing process, and high brightness and light-dark ratio. Color filters can be provided.

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 the contrast. Chromium can be used as the material for the black matrix. In this case, a method of depositing chromium on the entire glass substrate and forming a pattern by 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 can use a black pigment or a black dye as a coloring material. For example, carbon black can be used alone or a mixture of carbon black and a coloring pigment can be used. At this time, since the coloring pigment having insufficient light-shielding property is mixed, the amount of the coloring material is relatively large. There is an advantage that the increase does not reduce the strength of the film or the adhesion to the substrate.

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

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

Hereinafter, the present specification will be described in detail with reference to examples. The examples below are for illustration purposes only, and the scope of the specification is not limited to the scope of the examples, including the scope described in the claims below and their substitutions and modifications.

<Manufacturing example>

<Production Example 1> -Production of Compound 1-1

Production of [Compound A]

In a 100 mL 1-neck round bottom flask, compound A-1 (Benzenesulfonate Dichlorosulfofluororesin) (3 g, 7.40 mmol, 1 eq), compound A-2 (2- (Ethylamino) ethanol) (5.28 g, 59.22 mmol, 8 eq). ), After adding 50 g of DI-water, the mixture was stirred at 100 ° C. After this, the reaction was allowed to proceed overnight (overnight, 12 hours). The reaction was terminated by quenching with 1M HCl Solution, and NaCl (sodium chloride) was added to precipitate the reaction product. The precipitate produced was filtered under reduced pressure and then dried in an oven (Oven) at 80 ° C. After drying, for the purpose of removing NaCl in the product, the mixture is dissolved in DMF (Dimethylformamide) and filtered, and then the filtrate is quenched with diethyl ether, filtered under reduced pressure, dried, and the compound is compounded. A (2.88 g, 5.64 mmol, 76%) was obtained.

Ionization mode: APCI +: m / z = 511 [M + H] +, Exact Mass: 510.18

Production of [Compound B]

3,5-Di-tert-butyl-4-hydroxyacid compound A-3 (1.91 g, 7.63 mmol, 3 eq) was added to 75 g of Dichlolomethane and stirred. Ice bath was provided to bring the temperature to 0 ° C., after which N- (3-Dimethyllaminopophil) -N'-ethylcarbodiimide (EDC-HCl) (1.462 g, 7.63 mmol, 3eq) was added and stirred for 15 minutes. .. A small amount of Dimethylformamide, 4-Dimethylaminopyridine (DMAP) (0.244 g, 2 mmol) was added, compound A (1.3 g, 2.545 mmol, 1 eq) was added, and the mixture was reacted at 0 ° C. for 2 hours at room temperature. The reaction was carried out overnight. Distilled water (150 ml) and Dichloromethane (70 ml) were additionally added for extraction, and the organic layer _{was passed through sulfonyl 4} to remove water, and the solvent was removed under reduced pressure. After this, the precipitate was separated by column chromatography (Eluent MC (dichlorimethane): MeOH (METhanol) = 10: 1). As a result, compound B (1.36 g, 1.396 mmol) was obtained, and the yield was 54.8%.

Ionization mode: APCI +: m / z = 743 [M + H] +, Exact Mass: 742.33

[Production of Compound 1-1]

Compound B (1.485 g, 2.0 mmol) was dissolved in chloroform (40 ml) and D-MAP (0.487 g, 2.0 mmol) was added. 2-Hydroxyethyl Methacrylate (0.488 ml, 4.0 mmol) was added, and EDC (N- (3-Dimethyllaminoppil) -N'-ethylcarbodiimide (1.15 g, 6.0 mmol) in CHCl ₃ (10 ml) was added. Then, the reaction was carried out at room temperature for 72 hours. After H ₂ O quenching, the mixture was transferred to a separation funnel and the aqueous layer was _{extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried over _{Na 2} SO _4. Purification with Flash silicon chromatography (CH ₂ Cl ₂ (dichloromethane): MeOH (Methanol) = 9: 1) gave compound 1-1 (0.991 g, 1.68 mmol, 56%).

Ionization mode: APCI +: m / z = 855 [M + H] +, Exact Mass: 854

<Production Example 2> -Production of Compound 1-4

Production of [Compound C]

Compound A-4 (2.12 g, 7.63 mmol, 3 eq) of 3- (3,5-Di-tert-butyl-4-hydroxyphenyl) propanoic acid, N- (3-Dimethylaminopropanol) -N'-ethylcarbodiimide EDC-HCl) (1.462 g, 7.63 mmol, 3 eq), Dimethylformamide, 4-Dimethylaminopyridine (DMAP) (0.244 g, 2 mmol), Compound A (1.3 g, 2.545 mmol, 1 eq). It was produced in the same manner as in Production Example 1-2 to obtain Compound C (1.15 g, 1.49 mmol), and the yield was 58.5%.

Ionization mode: APCI +: m / z = 771 [M + H] +, Exact Mass: 770

[Production of Compound 1-4]

Compound C (1.0 g, 1.30 mmol), D-MAP (0.487 g, 2.0 mmol), 2-Hydroxyethyl Metylrate (0.317 ml, 2.6 mmol), EDC (N- (3-Dimethylaminopropyl) -N '-Ethylcarbodimide) (1.15 g, 6.0 mmol) was added to prepare compound 1-4, 0.84 g (yield 73.0%) in the same manner as in the production of compound 1-1. Obtained.

Ionization mode: APCI +: m / z = 883 [M + H] +, Exact Mass: 882
<Production Example 3> -Production of Compound 1-6

Production of [Compound D]

Compound A-1 (Benzenesulfonate Dichlorosulfofluorescein) (3 g, 7.40 mmol, 1 eq) and Diethanolamine (3.89 g, 37 mmol, 5 eq) were added to prepare the compound D, 3. 2 g (yield 79.8%) was obtained.

Production of [Compound E]

Compound A-3 (2.54 g, 10.16 mmol, 4 eq) and compound D (1.38 g, 2.54 mmol, 1 eq) of 3,5-Di-tert-butyl-4-hydroxy acid are added to compound B. The production was carried out in the same manner as in the above production to obtain 1.21 g (yield 47.3%) of Compound E.

Ionization mode: APCI +: m / z = 1007 [M + H] +, Exact Mass: 1006

Production of [Compound 1-6]

Compound E (1.0 g, 0.99 mmol, 1 eq) and 2-Hydroxyethyl Methacrylate (0.36 ml, 3 mmol, 3 eq) were added to prepare compound 1-6 in the same manner as in the production of compound 1-1. Was obtained in an amount of 0.8 g (yield 65.7%).

Ionization mode: APCI +: m / z = 1231 [M + H] +, Exact Mass: 1230

<Production Example 4> -Production of Compound 2-1

Compound B (1 g, 1.34 mmol, 1 eq) is dissolved in 50 ml of Dichlolomethane, then sodium hydroxide (0.05 g, 1.34 mmol, 1 eq) and Benzyltrimethyl ammonia 0.02 g are added, and the mixture is stirred at room temperature for 30 minutes and then 1-. Chloro-2,3-epoxypropane (0.25 g, 2.68 mmol, 2 eq) was added, and the mixture was stirred at 40 ° C. for 20 hours. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution, transferred to a separation funnel, and the aqueous layer was _{extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried over _{Na 2} SO _4. The organic layer is dried under reduced pressure _{and then purified by Flash silica color chromatography (CH 2} Cl ₂ (dichloromethane): MeOH (METhanol) = 9: 1) to purify compound 2-1 (0.65 g, 0.81 mmol, 60.7). %) Was obtained.

Ionization mode: APCI +: m / z = 799 [M + H] +, Exact Mass: 798

<Production Example 5> -Production of Compound 3-1

After dissolving compound B (1 g, 1.34 mmol, 1 eq) in 50 ml of Dichloromethane, sodium hydroxide (0.05 g, 1.34 mmol, 1 eq) and Benzyltrimethyl ammonia 0.02 g are added, and the mixture is stirred at room temperature (25 ° C.) for 30 minutes. After that, 3- (chromomethyl) -3-methyloxetane (0.32 g, 2.68 mmol, 2eq) was added, and the mixture was stirred at 40 ° C. for 20 hours. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution, transferred to a separation funnel, and the aqueous layer was _{extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried over _{Na 2} SO _4. The organic layer is dried under reduced pressure _{and then purified by Flash silica color chromatography (CH 2} Cl ₂ (dichloromethane): MeOH (Methanol) = 9: 1) to purify compound 3-1 (0.62 g, 0.75 mmol, 55.9). %) Was obtained.

Ionization mode: APCI +: m / z = 828 [M + H] +, Exact Mass: 827

<Production Example 6> -Production of Compound 4-1

Compound B (1 g, 1.34 mmol, 1 eq) is dissolved in 50 ml of Dichloromethane, then sodium hydroxide (0.05 g, 1.34 mmol, 1 eq) and Benzyltrimethyl ammonia 0.02 g are added, and the mixture is stirred at room temperature for 30 minutes and then 2-. Chloroacetic acid (0.25 g, 2.68 mmol, 2 eq) was added and stirred at 40 ° C. for 20 hours. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution, transferred to a separation funnel, and the aqueous layer was _{extracted with CHCl 3} (Chloroform). The organic layer was separated, washed with brine, and dried over _{Na 2} SO _4. The organic layer is dried under reduced pressure _{and then purified by Flash silica color chromatography (CH 2} Cl ₂ (dichloromethane): MeOH (Methanol) = 9: 1), and the compound 4-1 (0.54 g, 0.67 mmol, 50.1) is purified. %) Was obtained.

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

<Comparison example>

Compound of Comparative Example 1.

Rhodamine B was used as the compound 1 of the comparative example.

Production of the compound of Comparative Example 2

After putting compound A-1 (Benzenesulfonate Dichlorosulfofluorescein) (3 g, 7.40 mmol, 1 eq), 2,6-dimethylidine (7.18 g, 59.22 mmol, 8 eq) and NMP 20 g into a 100 mL 1-neck round bottom flask. , 150 ° C. for 4 hours. After confirming with TLC (Dichloromethane: Metric alcohol = 15: 1), the reaction solution was cooled to room temperature, then quenched with 300 ml of 1M HCl Solution to terminate the reaction, and NaCl (sodium chloride) was added. The reaction was precipitated. The precipitate produced was filtered under reduced pressure and then dried in an oven (Oven) at 80 ° C. After drying, for the purpose of removing NaCl in the product, the mixture is dissolved in DMF (Dimethylformamide) and filtered, and then the filtrate is quenched with diethyl ether, filtered under reduced pressure, dried, and the compound is compounded. 2-1 (3.23 g, 5.64 mmol, 76%) of Comparative Example 2-1 was obtained.

Ionization mode: APCI +: m / z = 575 [M + H] +, Exact Mass: 514.19

_{Comparative Example 2-1 (3 g, 5.22 mmol, 1 eq), K 2} CO ₃ (2.885 g, 20.88 mmol, 4 eq), and NMP 50 g of the compound were put into a 100 mL 1-neck round bottom flask, and then at room temperature. Was stirred for 10 minutes. 2-((3-iodotropyl) carbamoyl) benoic acid (6.955 g, 20.88 mmol, 4 eq) was added and stirred at 95 ° C. for 12 hours. After removing the solvent under reduced pressure, 120 ml of water was added, and the mixture was stirred with Ice water bath for 1 hour. The precipitate was filtered under reduced pressure and then dried in an oven (Oven) at 80 ° C. After drying, the precipitate was added to 100 ml of ethyl acetate, stirred, and then filtered. 2-((3-iodopropyl) carbamoyl) benoic acid is removed, the solvent is removed under reduced pressure, and then the precipitate is dissolved in MeOH and filtered under gravity, and the compound is Comparative Example 2 (4.113 g). 4.17 mmol, 80%) was obtained.

Ionization mode: APCI +: m / z = 985 [M + H] +, Exact Mass: 984.34

Production of the compound of Comparative Example 3

After putting compound A-1 (Benzenesulfonate Dichlorosulfofluorescein) (3 g, 7.40 mmol, 1 eq), 2,6-dimethylidine (7.18 g, 59.22 mmol, 8 eq) and NMP 20 g into a 100 mL 1-neck round bottom flask. , 150 ° C. for 4 hours. After confirming with TLC (Dichloromethane: Metric alcohol = 15: 1), the reaction solution was cooled to room temperature, then quenched with 300 ml of 1M HCl Solution to terminate the reaction, and NaCl (sodium chloride) was added. The reaction was precipitated. The precipitate produced was filtered under reduced pressure and then dried in an oven (Oven) at 80 ° C. After drying, for the purpose of removing NaCl in the product, the mixture is dissolved in DMF (Dimethylformamide) and filtered, and then the filtrate is quenched with diethyl ether, filtered under reduced pressure, dried, and the compound is compounded. 2-1 (3.23 g, 5.64 mmol, 76%) of Comparative Example 2-1 was obtained.

Ionization mode: APCI +: m / z = 575 [M + H] +, Exact Mass: 514.19

_{Comparative Example 2-1 (3 g, 5.22 mmol, 1 eq), K 2} CO ₃ (2.885 g, 20.88 mmol, 4 eq), and NMP 50 g of the compound were put into a 100 mL 1-neck round bottom flask, and then at room temperature. Was stirred for 10 minutes. 2-((3-iodopoxy) carbonyl) benzoic acid (6.976 g, 20.88 mmol, 4 eq) was added and stirred at 95 ° C. for 12 hours. After removing the solvent under reduced pressure, 120 ml of water was added, and the mixture was stirred with Ice water bath for 1 hour. The precipitate was filtered under reduced pressure and then dried in an oven (Oven) at 80 ° C. After drying, the precipitate was added to 100 ml of Ethyl Actate, stirred, and then filtered. 2-((3-iodopoxy) carbonyl) benzoic acid was removed, the solvent was removed under reduced pressure, and then the precipitate was dissolved in MeOH and filtered under gravity, and the compound was compared with Comparative Example 3 (4.379 g). 4.43 mmol, 85%) was obtained.

Ionization mode: APCI +: m / z = 987 [M + H] +, Exact Mass: 986.31

<Example>

<Production of Example 1 of Resin Composition>

Based on 100 parts by weight of the total weight of the resin composition, 0.85 parts by weight of the compound, 20.78 parts by weight of the binder A as the binder resin, and dipentaerythritol hexaacrylate 20.46 of the acrylic monomer as the polyfunctional monomer. Parts by weight, photoinitiator PBG-3057 0.68 parts by weight, leveling agent F-554 0.6 parts by weight, adhesive aid KBM-503 0.06 parts by weight, solvent diacetone alcohol (DAA, Diacetonealcohol) 56.57 The parts by weight were mixed to produce Example 1 of the resin composition.

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

<Production of Examples 2 to 6 of the resin composition>

Examples 2 to 6 of the resin composition were prepared in the same manner as in Example 1 of the resin composition except that the compound 1-1 of Example 1 of the resin composition was changed to the compounds shown in Table 1 below. Manufactured.

<Production of Comparative Examples 1 to 3 of Resin Composition>

Comparative Examples 1 to 3 of the resin composition were produced in the same manner as in Example 1 of the resin composition except that the compound of Example 1 of the resin composition was changed to the compound shown in Table 2 below.

<Experimental example>

Substrate preparation

The resin compositions produced in Comparative Examples 1 to 3 and Examples 1 to 6 were spin-coated on glass (5 cm × 5 cm) and preheated (Prebake) at 100 ° C. for 100 seconds to form a film. rice field. After the pre-heat treatment, a post-heat treatment (Post heat treatment) was performed 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.

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

Using the values L *, a *, and b * obtained from the absorption spectrum obtained with the C light source as the backlight, ΔEab was calculated by the following formula 1 and shown in Table 3 below.

[Equation 1]
ΔEab (L *, a *, b *) = {(△ L *) 2 + (△ a *) 2 + (△ b *) 2} 1/2

A small ΔEab value means that there is little color change, and indicates that the heat resistance is excellent.

According to Table 3, it was confirmed that the ΔEab values of Examples 1 to 6 were smaller than the ΔEab values of Comparative Examples 1 to 3. As a result, by using a xanthene-based dye which is a compound represented by the above chemical formula 1 into which a specific substituent and a crosslinkable group according to the present specification are introduced, a coloring composition and a color for a color filter having excellent heat resistance can be used. It was confirmed that it was possible to obtain a filter.

Chemical resistance evaluation

A substrate was prepared by the method for producing a substrate, cut into 1 cm × 5 cm, and then two pieces of the substrate cut into 1 cm × 5 cm were immersed in 16 g of N-methyl-2-pyrrolidone solvent, and then a projection at 80 ° C. Additional Bucking was performed in the oven for 40 minutes. The absorbance of the solvent from which the substrate piece was taken out was measured, and the absorbance and the improvement rate (%) of Examples 1 to 6 in comparison with Comparative Example 1 are shown in Table 3 below.

According to Table 3, it was confirmed that the absorbance of Examples 1 to 6 was smaller than the absorbance of Comparative Examples 1 to 3. The smaller the absorbance, the better the chemical resistance. As a result, by using a xanthene-based dye which is a compound represented by the chemical formula 1 into which a specific substituent and a crosslinkable group according to the present specification have been introduced, the chemical resistance to a solvent is improved for coloring for a color filter. It was confirmed that the composition was obtained.

Claims (13)

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

In the chemical formula 1,
L1 to L4 are the same or different from each other and are independently bonded; or unsubstituted alkylene groups .
Ar1 and Ar2 are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; an aryl group substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms ; an ethyl group substituted with a hydroxy group; an ethyl group substituted with a hydroxy group. It is a propyl group or is represented by the following chemical formula 1-A; or the following chemical formula 1-B.
R1 to R3 are the same or different from each other and are independently hydrogen; or deuterium.
r1 and r2 are integers 1-3, respectively,
r3 is an integer of 1 to 4 and
When r1 is 2 or more, R1 is the same as or different from each other.
When r2 is 2 or more, R2 is the same as or different from each other.
When r3 is 2 or more, R3 is the same as or different from each other.
X1 and X2 are the same or different from each other and are represented by the following chemical formulas 1-A or 1-B, respectively.
[Chemical formula 1-A]

[Chemical formula 1-B]

In the chemical formulas 1-A and 1-B,
The Q1 and Q2 are the same or different from each other and are independently O; or NH.
L101 and L102 are the same or different from each other and are independently bonded; or unsubstituted alkylene groups , respectively.
R101 to R105 are the same or different from each other and are independently hydrogen; deuterium; hydroxy groups; or unsubstituted alkyl groups .
R106 is any one selected from the following structures and carboxylic acid groups (-COOH).

In the structure
L201 is a direct bond; or O,
R201 to R203 are the same or different from each other, and independently, hydrogen; deuterium; an unsubstituted alkyl group ; or an alkenyl group substituted with an alkyl group having 1 to 10 carbon atoms.
r202 is an integer from 1 to 3 and
r203 is an integer of 1 to 5 and
When the r202 is 2 or more, the R202s are the same or different from each other.
When r203 is 2 or more, R203 are the same or different from each other.

Means the part to be connected,
At least one of the Ar1, Ar2, X1 and X2 is represented by the chemical formula 1-B.
At least one of the X1 and X2 is represented by the chemical formula 1-A.
When at least one of the Ar1 and Ar2 is represented by the chemical formula 1-A, at least one of the X1 and X2 is represented by the chemical formula 1-B.
The chemical formula 1 is represented by the following chemical formula 2.
The compound according to claim 1:
[Chemical formula 2]

In the chemical formula 2,
The definitions for L1 to L4, Ar1, Ar2, R1 to R3, r1 to r3, Q1, Q2, L101, L102, and R101 to R106 are the same as those defined in Chemical Formula 1. The L1 to L4 are the same or different from each other and are independently bonded to each other; an unsubstituted methylene group, an unsubstituted ethylene group, or an unsubstituted propylene group.
The compound according to claim 1 or 2. The R103 is a hydroxy group.
The compound according to any one of claims 1 to 3. The R102 and R104 are identical or different from each other and are independently unsubstituted tert-butyl groups.
The compound according to any one of claims 1 to 4. It is any one selected from among lower Symbol of the compound, the compound:

.. A polymer containing the compound according to any one of claims 1 to 6 as a monomer. A color material composition containing the compound according to any one of claims 1 to 6. Further comprising at least one of dyes and pigments,
The color material composition according to claim 8. The dye is one or more dyes selected from xanthene dyes, cyanine dyes, anthraquinone dyes, azaporphyrin dyes, and azometal complex compounds.
The pigment is a blue pigment or a purple pigment,
The color material composition according to claim 9. The compound according to any one of claims 1 to 6;
Binder resin;
Polyfunctional monomer;
A resin composition comprising a photoinitiator; and a solvent. A color filter containing the resin composition according to claim 11. A display device including the color filter according to claim 12.