TWI714122B - Compound, polymer, colorant composition, resin composition, color filter and display device - Google Patents

Abstract

This invention is related to a compound represented by chemical formula 1, a polymer comprising same, a colorant composition, a resin composition, a color filter and a display device. In chemical formula 1, the definition of each substituent is the same as defined in the description of the invention. [chemical formula 1]

Description

Compound, polymer, coloring material composition, resin composition, color filter, and display device

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0071745 filed with the Korean Patent Office on June 22, 2018, and incorporates all of its contents into this specification.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0055682 filed with the Korean Patent Office on May 13, 2019, and incorporates all of its contents into this specification.

This specification is about a compound, polymer, coloring material composition, resin composition, color filter, and display device.

Recently, as the light source of liquid crystal display (LCD), most of the light emitting diodes (light emitting diodes, LED) or organic light emitting diodes (organic light The emitting diode (OLED) element replaces the existing cold cathode tube (cold cathode fluorescent lamp (CCFL)). If using the LED or As the light source, OLED emits red, green, and blue light by itself, so no additional color filter is needed. Therefore, in order to produce thin-film displays, flexible displays, etc., products that use self-luminescence such as LEDs and OLEDs with color filters removed as unit pixels have been developed and produced.

However, in the case of using LEDs, OLEDs, etc. as a unit pixel display, it is difficult to achieve a large area, and it is not easy to match or adjust the required color coordinates with light emitted from the LED or OLED light source. Therefore, in order to realize the desired hue, a color filter compatible with the light source is required, and a pigment dispersion method using a pigment as a colorant is generally applied.

However, in the case of a pigment dispersion liquid, there are the following disadvantages: the pigment exists in the state of particles and scatters light. Not only that, the surface area of the pigment increases sharply due to the miniaturization of the pigment, and the dispersion stability deteriorates due to this. And generate uneven pigment particles.

Therefore, in order to achieve high brightness, high contrast ratio and high resolution, the use of dyes as colorants is being studied. Among them, dibenzopyran (xanthene) dyes are often used as red colorants. Generally speaking, dibenzopyran dyes have good gradient slopes, high absorbance in the range of 500nm to 550nm, and are effective for color characteristics. The solubility is higher than that of pigments, and it has the disadvantages of reduced chemical resistance and low heat resistance.

This specification provides a compound, polymer, coloring material composition, resin composition, color filter, and display device.

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

In the chemical formula 1, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and Ar1 and Ar2 are the same as each other Or different, each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl, or is represented by the following chemical formula 1 -A or the following chemical formula 1-B, R1~R3 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkane Group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, r1 and r2 are each an integer of 1 to 3, r3 is an integer of 1 to 4, when the r1 is 2 or more When R1 is the same or different from each other, when r2 is 2 or more, R2 is the same or different from each other, 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, respectively, as follows Represented by chemical formula 1-A or chemical formula 1-B,

In the chemical formula 1-A and the chemical formula 1-B, Q1 and Q2 are the same or different from each other, and are independently O or NH, respectively, and L101 and L102 are the same or different from each other, and are independently directly bonded, substituted or not. Substituted alkylene, or substituted or unsubstituted arylene, R101~R105 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl, or substituted Or unsubstituted cycloalkyl, R106 is any one selected from the following structures and carboxylic acid groups (-COOH),

是指連結的部位，於所述Ar1及Ar2中的至少一者由所述化學式1-A所表示的情況下，所述X1及X2中的至少一者由所述化學式1-B所表示， 於所述Ar1及Ar2中的至少一者由所述化學式1-B所表示的情況下，X1及X2中的至少一者由所述化學式1-A所表示。 In the structure, L201 is directly bonded or O, R201~R203 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, A substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, r202 is an integer of 1 to 3, and r203 is an integer of 1 to 5. When the r202 is 2 or more, R202 is the same as each other Or different, when r203 is 2 or more, R203 is the same or different from each other,

Refers to the connecting site. In the case where 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, In the case where 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 aspect 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 this specification, a coloring material composition containing the compound represented by the chemical formula 1 is provided.

According to another aspect of the present specification, a resin composition containing the coloring material composition is provided.

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

In addition, according to an embodiment of the present specification, a display device including the color filter is provided.

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

In addition, according to an embodiment of the present specification, the coloring material composition containing the compound represented by the chemical formula 1 has the following characteristics: compared with the case of using existing pigments, it has high brightness.

Furthermore, according to an embodiment of this specification, by using a coloring material composition containing the compound represented by the chemical formula 1, a color filter with excellent heat resistance and chemical resistance can be produced.

In addition, according to an implementation aspect of this specification, if the use contains The coloring material composition of the compound represented by the chemical formula 1 does not need to perform the dispersion step necessary for the application of the existing pigment, so it has the effect of saving cost.

Recently, as the light source of liquid crystal display (LCD), most of the light emitting diode (light emitting diode) or OLED (organic light emitting diode) elements that are neither driven nor liquid crystal type are used to replace the existing cold cathode tube (CCFL). ). If the LED or OLED is used as a light source, it will emit red, green, and blue light, so no additional color filter is needed. Therefore, in order to produce thin-film displays, flexible displays, etc., products that use self-luminescence such as LEDs and OLEDs with color filters removed as unit pixels have been developed and produced.

However, in the case of using LEDs, OLEDs, etc. as a unit pixel display, it is difficult to achieve a large area, and it is not easy to match or adjust the required color coordinates with light emitted from the LED or OLED light source. Therefore, in order to realize the desired hue, a color filter compatible with the light source is required, and a pigment dispersion method using a pigment as a colorant is generally applied.

However, in the case of a pigment dispersion liquid, there are the following disadvantages: the pigment exists in the state of particles and scatters light. Not only that, the surface area of the pigment increases sharply due to the miniaturization of the pigment, and the dispersion stability deteriorates due to this And generate uneven pigment particles.

Therefore, in order to achieve high brightness, high contrast ratio and high resolution, Study the use of dyes as colorants. Among them, xanthene dyes are mostly used as red colorants. Generally speaking, xanthene dyes have good gradient slopes and high absorbance in the range of 500nm~550nm, which is effective for color characteristics, but due to higher solubility than pigments, there is chemical resistance Decreased performance and the disadvantage of low heat resistance.

However, the compound represented by Chemical Formula 1 in the present specification can of course improve heat resistance by containing an antioxidant, and by containing a crosslinkable group, it has the effect of suppressing the transfer and elution of weak points as a dye. Therefore, by using the coloring material composition containing the compound represented by Chemical Formula 1 in this specification, a color filter excellent in heat resistance and chemical resistance can be produced.

In addition, if the coloring material composition containing the compound represented by Chemical Formula 1 in this specification is used, the dispersion step necessary for applying existing pigments may not be performed, which has the effect of saving costs.

Hereinafter, this specification will be explained in more detail.

This specification provides a compound represented by the chemical formula 1.

The dibenzopiperan dye represented by the chemical formula 1 has a reactive group represented by the substituent R106 of the chemical formula 1, thereby being able to interact between the dibenzopiperan dyes by free radicals or heat Interact with each other. In addition, the dibenzopyran dye represented by the chemical formula 1 can react with the polymerizable compound, alkali-soluble resin, etc. contained in the resin composition of this specification. When the reaction occurs, the dibenzopyran dye is firmly fixed in the cured film, and as a result, heat resistance and chemical resistance are improved.

In this specification, examples of substituents will be described below, but they are not limited thereto.

是指連結的部位。 In this manual,

Refers to the connected part.

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent. If the substituted position is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, then It 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.

In this specification, the term "substituted or unsubstituted" means that it is selected from deuterated hydrogen, halogen group, nitrile group, alkyl group, cycloalkyl group, amine group, silyl group, boron group, phosphine oxide group , An aryl group and one or more substituents in the group consisting of one or more heterocyclic groups containing N atoms, O atoms, S atoms, Se atoms and Si atoms, or are exemplified by the above Two or more of the substituents in the substituents are substituted by the substituents linked by the substituents, or they do not have any substituents.

In this specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, and is preferably 1-50, more preferably 1-30. In addition, it can be 1-20 or 1-10. Specific examples are: methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, second butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary 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, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl Group, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but it is not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but it is preferably one with 3 to 60 carbon atoms, more preferably 3 to 30. In addition, it can be 3-20 or 3-10. Specifically: cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methyl Cyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc. are not limited to these.

In this specification, the alkenyl group may be linear or branched, and the carbon number is not particularly limited, preferably 2-40, more preferably 2-30. In addition, it can be 2-20 or 2-10. Specifically: vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl Alkenyl, 3-methyl-1-butenyl, 1,3-butadienyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-di Phenyl vinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl) vinyl-1-yl, 2,2-bis(diphenyl-1-yl) vinyl-1- Although it is not limited to these groups, a stilbene group, a styryl group, etc.,.

In this specification, when the aryl group is a monocyclic aryl group, the carbon number is not particularly limited, and the carbon number is preferably 6 to 50, and more preferably 6 to 30. In addition, it can be 6-20 or 6-12. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a triphenyl group, a bitetraphenyl group, etc., but it is not limited to these.

基、芴基等，但並非限定於該些。 When the aryl group is a polycyclic aryl group, the carbon number is not particularly limited, and the carbon number is preferably 10-50, and more preferably 10-30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylene, triphenyl,

However, it is not limited to these radicals, fluorenyl radicals, etc.

In this specification, the amine group can be selected from -NH ₂ , alkyl amine group, N-alkyl aryl amine group, aryl amine group, N-aryl heteroaryl amine group, N-alkyl heteroaryl amine group The number of carbons in the group consisting of a group and a heteroarylamine group is not particularly limited, and it is preferably 1-30. Specific examples of amino groups include: methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-Methyl-anthrylamino, diphenylamino, N-phenylnaphthylamino, xylylamino, N-phenyltolylamino, triphenylamino, N-phenyl Biphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrylamino, N-biphenylphenanthrylamino The amino group, N-phenylfluorenylamino group, N-phenyltriphenylamino group, N-phenanthrylfluorenylamino group, N-biphenylfluorenylamino group, etc. are not limited to these.

In this specification, the silyl group may be represented by the chemical formula -SiY1Y2Y3, and the Y1, Y2, and Y3 may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, respectively. Specifically, the silyl group includes: Trimethylsilyl (TMS), triethylsilyl, tert-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl Silyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. are not limited to these.

In this specification, the boron group can be represented by the chemical formula of -BY4Y5, and the Y4 and Y5 can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group, respectively. Specifically, the boron group includes: trimethyl boron, triethyl boron, tert-butyl dimethyl boron, triphenyl boron, phenyl boron, etc., but it is not limited to these some.

In this specification, the heterocyclic group contains one or more of N, O, S, Si, and Se as heterogeneous atoms, and the carbon number is not particularly limited, and the carbon number is preferably 2 to 60, and more preferably It is 2~30. Furthermore, it can be 2-20. Examples of heterocyclic groups are: thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridine Ridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazine (phthalazine) group, pteridine (pteridine) group, pyrido pyrimidine (pyrido pyrimidine) group, pyrido Pyrazine (pyrido pyrazine) base, pyrazino pyrazine (pyrazino pyrazine) base, isoquinolinyl, indolyl, pyrido indole (pyrido indole) base, indenopyrimidine (5H-indeno pyrimidine) base, carbohydrate Azolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, dibenzofuranyl, phenanthroline ( phenanthroline) group, thiazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, etc., but it is not limited to these.

In the present specification, if the heteroaryl group is excluded from being aromatic, the heteroaryl group can be selected from the examples of the heterocyclic group, but it is not limited to these.

In this specification, alkylene refers to a group with two bonding positions on the alkyl group, that is, a divalent group. If a divalent group is excluded, the description of the alkyl group can be applied to these groups, respectively.

In this specification, the aryl group refers to a group with two bonding positions on the aryl group, that is, a divalent group. If a divalent group is excluded, the description of the aryl group can be applied to these groups, respectively.

In one embodiment of this specification, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylalkylene group.

In one embodiment of the present specification, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, or a chain having 6 to 30 carbon atoms. Substituted or unsubstituted aryl group.

In one embodiment of this specification, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 20 carbons, or a carbon 6 to 20 alkylene group. Substituted or unsubstituted aryl group.

In an embodiment of this specification, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 10 carbons, or a carbon 6 to 12 alkylene group. Substituted or unsubstituted aryl group.

In one embodiment of this specification, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted methylene group, a substituted or unsubstituted ethylene group, or a substituted Or unsubstituted propylene.

In an embodiment of the present specification, L1 to L4 are the same or different from each other, and are each independently a direct bond, methylene, ethylene, or ethylene.

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

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

In one embodiment of this specification, Ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbons, and substituted with 3 to 30 carbons. Or unsubstituted cycloalkyl, or carbon number 6~30 The substituted or unsubstituted aryl group of is or is represented by the following chemical formula 1-A or the following chemical formula 1-B.

In one embodiment of this specification, Ar1 and Ar2 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbons, and substituted with 3 to 20 carbons. Or 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 an embodiment of this specification, Ar1 and Ar2 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbons, and substituted with 3 to 10 carbons. Or 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 this specification, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group , Or substituted or unsubstituted phenyl, or represented by the following chemical formula 1-A or the following chemical formula 1-B.

In an embodiment of this specification, Ar1 and Ar2 are the same or different from each other, and are each independently methyl substituted or unsubstituted with phenyl, ethyl, propyl substituted or unsubstituted with hydroxy, and isopropyl. , Or phenyl, or represented by the following chemical formula 1-A or the following chemical formula 1-B.

In one embodiment of this specification, Ar1 is methyl, ethyl substituted or unsubstituted with phenyl, ethyl, propyl, isopropyl, or phenyl substituted with hydroxy, Or it is represented by the following chemical formula 1-A or the following chemical formula 1-B.

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

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

In an embodiment of this specification, R1 to R3 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, and A substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

In an embodiment of this specification, R1 to R3 are the same or different from each other, and are independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl with 1 to 30 carbons, and 3 to 30 carbons. A substituted or unsubstituted cycloalkyl 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 an embodiment of this specification, R1 to R3 are the same or different from each other, and are independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl with 1 to 30 carbons, and 3 to 30 carbons. A substituted or unsubstituted cycloalkyl 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 an embodiment of this specification, R1 to R3 are the same or different from each other, and are independently hydrogen, deuterium, hydroxyl, and substituted or unsubstituted with 1 to 20 carbon atoms. Alkyl group with 3-20 carbons, substituted or unsubstituted cycloalkyl with 6-20 carbons, substituted or unsubstituted aryl with 6-20 carbons, or substituted or unsubstituted with 2-20 carbons The heterocyclic group.

In an embodiment of this specification, R1 to R3 are the same or different from each other, and are independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl with 1 to 10 carbons, and 3 to 10 carbons. A substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 12 carbons, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbons.

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

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

In one embodiment of this specification, r1 is an integer of 1~3.

In an embodiment of this specification, r1 is 3.

In an embodiment of this specification, r2 is an integer of 1~3.

In an embodiment of this specification, r2 is 3.

In one embodiment of this specification, r3 is an integer of 1~4.

In one embodiment of this specification, r3 is 4.

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

[Chemical formula 1-A]

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

In an implementation aspect of this specification, the Q1 and Q2 are O respectively.

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

In one embodiment of this specification, L101 and L102 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylalkylene group.

In an embodiment of this specification, L101 and L102 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 30 carbons, or a carbon 6 to 30 alkylene group. Substituted or unsubstituted aryl group.

In an embodiment of this specification, L101 and L102 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 20 carbons, or a carbon 6-20 alkylene group. Substituted or unsubstituted aryl group.

In an embodiment of this specification, L101 and L102 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group having 1 to 10 carbons, or a carbon 6-12 alkylene group. Substituted or unsubstituted aryl group.

In one embodiment of this specification, L101 and L102 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted methylene group, or a substituted or unsubstituted ethylene group.

In an embodiment of the present specification, L101 and L102 are the same or different from each other, and are each independently a direct bond, a methylene group, or an ethylene group.

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

In one embodiment of this specification, R101 to R105 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl with 1 to 30 carbons, or 3 to 30 carbons. The substituted or unsubstituted cycloalkyl group.

In one embodiment of this specification, R101 to R105 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl with 1 to 20 carbons, or 3 to 20 carbons. The substituted or unsubstituted cycloalkyl group.

In one embodiment of this specification, R101 to R105 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl with 1 to 10 carbons, or 3 to 10 carbons. The substituted or unsubstituted cycloalkyl group.

In one embodiment of this specification, R101 to R105 are the same or different from each other, and are each independently hydrogen, hydroxyl, or substituted or unsubstituted tertiary butyl.

In an embodiment of the present specification, R101 to R105 are the same or different from each other, and are each independently hydrogen, hydroxyl, or tertiary butyl.

In one embodiment of this specification, R103 is a hydroxyl group.

In one embodiment of this specification, R102 and R104 are the same or different from each other, and are each independently a substituted or unsubstituted tertiary butyl group.

In one embodiment of this specification, R102 and R104 are tertiary butyl groups.

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

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

In one embodiment of this specification, L201 is a direct bond.

In an embodiment of this specification, L201 is O.

In one embodiment of this specification, R201 to R203 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted A substituted aryl group, or a substituted or unsubstituted heterocyclic group.

In an embodiment of this specification, R201 to R203 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbons, and substituted with 2 to 30 carbons. Or an unsubstituted alkenyl group, a substituted or unsubstituted aryl group having 6 to 30 carbons, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbons.

In an embodiment of this specification, R201 to R203 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbons, and substituted with 2 to 20 carbons. Or an unsubstituted alkenyl group, a substituted or unsubstituted aryl group having 6 to 20 carbons, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbons.

In an embodiment of this specification, R201 to R203 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 10 carbons, and substituted with 2 to 10 carbons. Or an unsubstituted alkenyl group, a substituted or unsubstituted aryl group having 6 to 12 carbons, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbons.

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

In an embodiment of this specification, R201 to R203 are the same or different from each other, and each independently is hydrogen, methyl, or ethylene.

In one embodiment of this specification, R201 is an ethylene group substituted by a methyl group.

In one embodiment of this specification, R202 is hydrogen.

In one embodiment of this specification, R203 is hydrogen or methyl.

In one embodiment of this specification, r202 is an integer from 1 to 3, and r203 is an integer from 1 to 5. 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 as each other Or different.

In an 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 It means that 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.

In an embodiment of the present 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 an embodiment of this 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 an embodiment of this specification, the Ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, Or in the case of a substituted or unsubstituted aryl group, at least one of X1 and X2 is represented by the chemical formula 1-A, and the X1 and X2 are not represented by the chemical formula 1-A The other represented is represented by the chemical formula 1-B.

In an embodiment of this specification, the Ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, Or in the case of a substituted or unsubstituted aryl group, at least one of X1 and X2 is represented by the chemical formula 1-B, and the X1 and X2 are not represented by the chemical formula 1-B The other one is represented by the chemical formula 1-A.

In one embodiment of this specification, the chemical formula 1 can be represented by the following 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 chemical formula 1.

In an embodiment of this specification, the chemical formula 1 can be represented by the following chemical Formula 2 expressed.

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

In an embodiment of this specification, the chemical formula 1 can be represented by the following chemical formula 3.

[Chemical formula 3]

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

According to an example, in the chemical formula 3, at least one of Ar1 and Ar2 can 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 aspect of this specification provides a polymer containing the compound represented by the chemical formula 1 as a monomer.

The monomer refers to a substance used as a unit when a polymer compound is produced by a chemical reaction.

The polymer (polymer) refers to a compound formed by polymerizing the monomer, and refers to a polymer compound.

In one aspect of this specification, the polymer may contain other monomers in addition to the compound represented by the chemical formula 1 as a monomer. For example, the monomer contained in the following binder resin and/or the following polyfunctional monomer can be further contained as a monomer.

In one embodiment of this specification, the chemical formula 1 The weight average molecular weight of the compound as a single-weight polymer can be 5,000g/mol~30,000g/mol.

The weight average molecular weight refers to the non-uniform molecular weight, and one of the average molecular weights using the molecular weight of a certain polymer substance as a reference is obtained by averaging the molecular weights of the component molecular species of the polymer compound having a molecular weight distribution in weight fraction value.

The weight average molecular weight can be determined by Gel Permeation Chromatography (GPC) analysis.

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

In one aspect of this specification, the coloring material composition further contains at least one of dyes and pigments.

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

According to an embodiment of the present specification, the dye is one or more dyes selected from the group consisting of dibenzopyran dyes, cyanine dyes, anthraquinone dyes and azaporphyrin dyes, and the pigment is a blue pigment or Purple paint.

The dibenzopyran dye, cyanine dye, anthraquinone dye, and azaporphyrin dye are not particularly limited as long as they are used in the technical field.

The blue pigment is not limited as long as it is used in the technical field, and it may contain a copper phthalocyanine blue pigment. As an example of the copper phthalocyanine-based blue pigment, a compound classified as a pigment in the color index (published by The Society of Dyers and Colourists) can be cited. As specific examples, C.I. Color Index Pigment Blue 1, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, etc. can be cited.

The purple pigment is not limited as long as it is a user in the technical field, and it can be exemplified by CIs classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Color Index Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, etc.

An embodiment of this specification provides a resin composition containing the coloring material composition.

One aspect of this specification provides a resin composition containing the compound represented by the chemical formula 1, a binder resin, a multifunctional monomer, a photoinitiator, and a solvent.

In one aspect of this specification, the resin composition may further contain additives.

The additives may be selected from the group consisting of leveling agents and adhesion aids Any one of the group.

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

The binder resin may use a copolymer resin of a polyfunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility, and may further include a binder commonly used in this technical field.

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

Specific examples of the unsaturated carboxylic acid esters can be selected from the group consisting of: benzyl (meth)acrylate, methyl (meth)acrylate, ethyl (meth)acrylate, (methyl) )Butyl acrylate, dimethylaminoethyl (meth)acrylate, isobutyl (meth)acrylate, tertiary butyl (meth)acrylate, cyclohexyl (meth)acrylate, (meth) Isobornyl acrylate, ethylhexyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, hydroxyethyl (meth)acrylate, (meth)acrylate Yl)-2-hydroxypropyl acrylate, 2-hydroxy-3-chloropropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, octyl(meth)acrylate 2-hydroxypropyl ester, glycerol (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, ethoxydiethylene Alcohol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxytripropylene glycol (meth)acrylate, poly(ethylene glycol) methyl ether (meth)acrylate, benzene Diethylene glycol (meth)acrylate, p-nonylphenoxy polyethylene glycol (meth)acrylate, p-nonylphenoxy polypropylene glycol (meth)acrylate, Glycidyl (meth)acrylate, tetrafluoropropyl (meth)acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth)acrylate, octafluoro(meth)acrylate Amyl ester, heptafluorodecyl (meth)acrylate, tribromophenyl (meth)acrylate, α-hydroxymethyl methacrylate, α-hydroxyethyl methacrylate, α-hydroxypropyl methacrylate And α-hydroxy butyl methacrylate, but not limited to these.

Specific examples of the aromatic vinyl monomers can be selected from styrene, o-methylstyrene, (ortho, m, and p)-vinyl toluene, (ortho, m, and p)-methoxystyrene And (ortho, meta, p)-chlorostyrene, but 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 to these.

The specific examples of the unsaturated imines can be selected from N-phenyl maleimide, N-(4-chlorophenyl) maleimide, N-(4-hydroxybenzene) Group) maleimide and N-cyclohexyl maleimide, but it is not limited to these.

The acid anhydride includes maleic anhydride, methyl maleic anhydride, tetrahydrophthalic anhydride, etc., but is not limited to these.

The monomer for imparting alkali solubility is not particularly limited if it contains an acid group. For example, it is preferably selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, and fumaric acid. Diacid, monomethylmaleic acid, 5-norbornene-2-carboxylic acid, phthalic acid mono-2-((meth)acryloyloxy) ethyl ester, succinic acid mono- 2-((methyl) One or more of the group consisting of acryloyloxy) ethyl and ω-carboxy polycaprolactone mono(meth)acrylate, but it is not limited to these.

According to one aspect of the specification, the acid value of the adhesive resin is 50 KOH mg/g to 130 KOH mg/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 titration with a 0.1N potassium hydroxide (KOH) methanol solution.

In an implementation aspect of this specification, the binder resin may be a mass ratio of benzyl methacrylate: N-phenyl maleimide: styrene: methacrylic acid = 55: 9: 11: 25 copolymers.

The multifunctional monomer is a monomer that plays a role of forming a photoresist image by light, and specifically may be selected from propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, and neopentyl diacrylate. Alcohol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethanol diacrylate, trihydroxyethyl isocyanurate Trimethacrylate, trimethylpropane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, methacrylic acid condensation One or a mixture of two or more of the group consisting of glyceride and epoxycyclohexyl methacrylate.

In one aspect of this specification, the multifunctional monomer is dipentaerythritol hexaacrylate.

If the photoinitiator is one that generates free radicals by light to trigger crosslinking The initiator is not particularly limited. For example, it may be one or more selected from the group consisting of acetophenone-based compounds, biimidazole-based compounds, triazine-based compounds, and oxime-based compounds.

The acetophenone compounds include: 2-hydroxy-2-methyl-1-phenylpropane-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane- 1-ketone, 4-(2-hydroxyethoxy)-phenyl-(2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether , Benzoin butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl-(4-methylthio)phenyl-2-morpholin-1-propane-1-one , 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl)-butan-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, etc. , Is not limited to these.

The biimidazole-based compounds include: 2,2-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)- 4,4',5,5'-tetrakis(3,4,5-trimethoxyphenyl)-1,2'-biimidazole, 2,2'-bis(2,3-dichlorophenyl)- 4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(o-chlorophenyl)-4,4,5,5'-tetraphenyl-1,2'-biimidazole, etc. , Is not limited to these.

The triazine compounds are: 3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 1,1,1,3,3 ,3-hexafluoroisopropyl-3-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionate, ethyl-2-{4 -[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}acetate, 2-epoxyethyl-2-{4-[2,4-bis( Trichloromethyl)-s-triazin-6-yl]phenylthio) acetate, cyclohexyl-2-{4-[2,4-bis(trichloromethyl)-s-triazin-6-yl ]Phenylthio}acetate, benzyl-2-{4-[2,4-bis(trichloromethyl)-s-triazine-6- Yl]phenylthio}acetate, 3-{chloro-4-[2,4-bis(trichloromethyl)-s-triazin-6-yl]phenylthio}propionic acid, 3-{4- [2,4-Bis(trichloromethyl)-s-triazin-6-yl]phenylthio)propanamide, 2,4-bis(trichloromethyl)-6-p-methoxystyryl -S-triazine, 2,4-bis(trichloromethyl)-6-(1-p-dimethylaminophenyl)-1,3-butadienyl-s-triazine, 2-trichloromethyl Group-4-amino-6-p-methoxystyryl-s-triazine, etc. are not limited to these.

The oxime compound includes: 1,2-octanedione-1-(4-phenylthio)phenyl-2-(phthaloyl oxime) (Ciba-Geigy Company, CGI124), ethyl ketone-1-(9-ethyl)-6-(2-methylbenzyl-3-yl)-1-(O-acetoxime) (CGI242), N-1919( ADEKA (ADEKA) etc. are not limited to these.

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

The solvent may be one or more selected from the group consisting of the following compounds: 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 Base ether, chloroform, dichloromethane, 1,2-dichloroethane, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2-trichloroethylene, Hexane, heptane, octane, cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, tertiary butanol, 2-ethoxypropanol, 2-methyl Oxypropanol, 3-methoxybutanol, diacetone alcohol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, 3 -Ethyl ethoxypropionate, ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, propylene glycol monomethyl ether and dipropylene glycol monomethyl ether, But it is not limited to this.

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

In an embodiment of this specification, based on the total weight of the resin composition, the content of the compound represented by the chemical formula 1 is 0.1% by weight to 60% by weight, 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, the content of the multifunctional monomer is 0.1% by weight to 50% by weight, and the content of the solvent is 10% by weight %~80% by weight.

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

According to an embodiment of this specification, based on the total weight of the solid content in the resin composition, the content of the compound represented by the chemical formula 1 is 0.5% by weight to 90% by weight, and the binder resin The content of is 1% by weight to 50% by weight, the content of the photoinitiator is 0.1% to 20% by weight, and the content of the multifunctional monomer is 0.1% to 50% by weight.

The total weight of the solid content refers to the total weight of the components other than the solvent in the resin composition. The solid content and the weight% of each component based on the solid content can be measured by a common analysis method used in the art such as liquid chromatography or gas chromatography.

According to one aspect of this specification, the resin composition additionally includes a photocrosslinking sensitizer, a curing accelerator, an antioxidant, an adhesion promoter, a surfactant, a thermal polymerization inhibitor, an ultraviolet absorber, and Group of dispersants One or more than two additives.

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

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

The leveling agent may be polymeric or non-polymeric. Specific examples of polymeric leveling agents include polyethyleneimine, polyamide amine, and reaction products of amines and epoxides, and specific examples of non-polymeric leveling agents include non-polymer sulfur Compounds and non-polymer nitrogen-containing compounds, but not limited to these, can be used by ordinary users in the art.

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

The adhesion aid is not particularly limited, and can be used by ordinary users in the technical field.

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

The photo-crosslinking sensitizer can use one or more selected from the group consisting of the following compounds: benzophenone, 4,4-bis(dimethylamino)benzophenone, 4,4- Bis(diethylamino)benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-phthalate, 3,3-dimethyl- Benzophenone compounds such as 4-methoxybenzophenone, 3,3,4,4-tetra(tert-butylperoxycarbonyl)benzophenone; 9-fluorenone, 2-chloro-9 -Fluorenone compounds such as fluorenone and 2-methyl-9-fluorenone; thioxanthone, 2,4-diethyl thia Anthrone, 2-chlorothioxanthone, 1-chloro-4-propyloxythioxanthone, isopropylthioxanthone, diisopropylthioxanthone and other thioxanthone compounds; Xanthone compounds such as xanthone and 2-methylxanthone; anthraquinone, 2-methylanthraquinone, 2-ethylanthraquinone, tertiary butylanthraquinone, 2,6-di Anthraquinone compounds such as chloro-9,10-anthraquinone; 9-phenylacridine, 1,7-bis(9-acridinyl)heptane, 1,5-bis(9-acridinylpentane) , 1,3-bis(9-acridinyl)propane and other acridine compounds; benzil, 1,7,7-trimethyl-bicyclo[2,2,1]heptane-2,3-di Dicarbonyl compounds such as ketones and 9,10-phenanthrenequinone; 2,4,6-trimethylbenzyldiphenylphosphine oxide, bis(2,6-dimethoxybenzyl)-2, Phosphine oxide compounds such as 4,4-trimethylpentyl phosphine oxide; methyl-4-(dimethylamino) benzoate, ethyl-4-(dimethylamino) benzoate , 2-n-butoxyethyl-4-(dimethylamino)benzoate and other benzoate compounds; 2,5-bis(4-diethylaminobenzylidene)cyclopentan Ketone, 2,6-bis(4-diethylaminobenzylidene) cyclohexanone, 2,6-bis(4-diethylaminobenzylidene)-4-methyl-cyclopentanone, etc. Amine-based synergist; 3,3-carbonylvinyl-7-(diethylamino)coumarin, 3-(2-benzothiazolyl)-7-(diethylamino)coumarin , 3-benzyl-7-(diethylamino) coumarin, 3-benzyl-7-methoxy-coumarin, 10,10-carbonyl bis[1,1,7 ,7-Tetramethyl-2,3,6,7-tetrahydro-1H,5H,11H-C1]-benzopyrano[6,7,8-ij]-quinazin-11-one etc. Legginin compounds; chalcone compounds such as 4-diethylaminochalcone and 4-azidobenzylidene acetophenone; 2-benzylmethylene, 3-methyl-b- Naphththiazoline.

The hardening accelerator is used to improve hardening and mechanical strength. Specifically, one or more selected from the group consisting of the following compounds can be used: 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2 -Mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetra(3-mercapto Propionate), pentaerythritol-tris(3-mercaptopropionate), pentaerythritol-tetra(2-mercaptoacetate), pentaerythritol-tris(2-mercaptoacetate), trimethylolpropane-tris(2 -Thioglycolate) and trimethylolpropane-tris(3-mercaptopropionate).

The adhesion promoter used in this specification can be selected from methacryloxypropyl trimethoxysilane, methacryloxypropyl dimethoxysilane, methacryloxypropyl One or more of methacrylic silane coupling agents such as triethoxy silane and methacryloxy propyl dimethoxy silane can be used. The alkyl trimethoxy silane can be selected from octyl trimethoxy silane , Dodecyl trimethoxy silane, octadecyl trimethoxy silane, etc., select one or more types to use.

The surfactant is a silicone-based surfactant or a fluorine-based surfactant. Specifically, the silicone-based surfactant can be used: BYK-077, BYK-085, BYK-Chemie BYK-300, BYK-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, etc., fluorine-based surfactants can be used: DIC (DaiNippon Ink & Chemicals) company's F-114, F-177, F-410, F-411, F- 450, F-493, F-494, F-443, F-444, F-445, F-446, F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482, F-483, F-484, F-486, F-487, F-172D, MCF-350SF, TF-1025SF, TF-1117SF, TF- 1026SF, TF-1128, TF-1127, TF-1129, TF-1126, TF-1130, TF-1116SF, TF-1131, TF1132, TF1027SF, TF-1441, TF-1442, etc., but are not limited to these.

The antioxidant may be one or more selected from the group consisting of hindered phenol antioxidants, amine antioxidants, sulfur antioxidants, and phosphine antioxidants, but is not limited thereto.

Specific examples of the antioxidant include: phosphoric acid-based heat stabilizers such as phosphoric acid, trimethyl phosphate, or triethyl phosphate; 2,6-di-tert-butyl-p-cresol, octadecyl -3-(4-hydroxy-3,5-di-tert-butylphenyl) propionate, tetrabis[methylene-3-(3,5-di-tert-butyl-4-hydroxybenzene Yl)propionate)methane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,5-di Tertiary butyl-4-hydroxybenzyl diethyl phosphite, 2,2-thiobis(4-methyl-6-tertiary butylphenol), 2,6-di-tertiary butylphenol, 4 ,4'-Butylene-bis(3-methyl-6-tert-butylphenol), 4,4'-thiobis(3-methyl-6-tert-butylphenol) or bis[3, Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid] glycol ester (Bis[3,3-bis-(4'-hydroxy-3'-tert-butylphenyl)butanoic acid Hindered phenol such as glycol ester is a primary antioxidant; phenyl-α-naphthylamine, phenyl-β-naphthylamine, N,N'-diphenyl-p-phenylenediamine or N,N'-Di-β-naphthyl-p-phenylenediamine and other amine-based secondary antioxidants; dilauryl disulfide, dilauryl thiopropionate, distearyl thiopropionic acid Thio-based secondary antioxidants such as ester, mercaptobenzothiazole or tetramethylthiuram disulfide tetrabis[methylene-3-(laurylthio)propionate]methane; or triphenyl Phosphate, tris(nonylphenyl) phosphite, triisodecyl phosphite, bis(2,4-dibutylphenyl) pentaerythritol diphosphite (Bis(2,4-dibutylphenyl) Pentaerythritol Diphosphite) or (1,1'- Biphenyl)-4,4'-diylbisphosphonic acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl)((1,1'-Biphenyl)-4,4 Phosphite esters such as'-Diylbisphosphonous acid tetrakis[2,4-bis(1,1-dimethylethyl)phenyl]ester) are secondary antioxidants.

The ultraviolet absorber can use: 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chloro-benzotriazole, alkoxybenzophenone, etc., but not It is not limited to these, and can be used by ordinary users in the field.

As the thermal polymerization inhibitor, for example, one or more selected from the group consisting of the following compounds may be included: p-anisole, hydroquinone, pyrocatechol, and tertiary butylcatechol (t-butyl catechol), N-nitrosophenyl hydroxylamine ammonium salt, N-nitrosophenyl hydroxylamine aluminum salt, p-methoxyphenol, di-tert-butyl-p-cresol, o-benzene Triphenol, benzoquinone, 4,4-thiobis(3-methyl-6-tertiary butylphenol), 2,2-methylene bis(4-methyl-6-tertiary butylphenol) , 2-mercaptoimidazole and phenothiazine (phenothiazine), but not limited to these, and may include those generally known in the technical field.

The dispersant can be used in the following methods: a method of internally adding to the pigment in a form where the pigment is surface-treated in advance or a method of externally adding to the pigment. As the dispersant, compound-type, nonionic, anionic, or cationic dispersants can be used, and examples thereof include fluorine-based, ester-based, cationic, anionic, nonionic, and amphoteric surfactants. These can be used separately or in combination of two or more.

Specifically, the dispersant is selected from polyalkylene glycol and its ester, polyoxyethylene Alkylene polyol, ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonate, sulfonate, carboxylic acid ester, carboxylate, alkyl amine alkylene oxide adduct and alkyl One or more of the group consisting of base amine, but it is not limited to this.

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

In one embodiment of this specification, the color filter can be manufactured using a resin composition containing the coloring material composition.

In one embodiment of this specification, the resin composition may be coated on a substrate to form a coating film, and the coating film may be exposed, developed, and cured to form a photosensitive material in the form of a thin film or pattern, by A color filter is formed by containing the photosensitive material.

The coating method is not particularly limited, and spray method, roll coating method, spin coating method, etc. can be used, and spin coating method is generally widely used. In addition, after the coating film is formed, a part of the residual solvent can be removed under reduced pressure as appropriate.

The light source used to harden the resin composition of this specification includes, for example, mercury vapor arc (arc), carbon arc, Xe arc, etc. that emit light having a wavelength of 250 nm to 450 nm, but it is not necessarily limited to these.

The resin composition of this specification can be used for the pigment dispersion type photosensitive material for the manufacture of thin film transistor-liquid crystal display device (Thin Film Transistor-Liquid Crystal Display, TFT LCD) color filter, thin film transistor liquid crystal display device (TFT LCD) or organic Light-emitting diode black matrix forming photosensitive material, overcoat forming photosensitive material, columnar spacer photosensitive material, light-curing paint, light-curing ink, In light-curable adhesives, photosensitive materials for printing plates, printed wiring boards, and photosensitive materials for plasma display panels (Plasma Display Panel, PDP), there are no particular restrictions on their use.

The resin composition of one embodiment of this specification has excellent heat resistance and little color change caused by heat treatment. When manufacturing color filters, even if the curing process is used, it can provide high color reproduction rate, high brightness and high contrast ratio. Color filter.

The substrate can be a glass plate, a silicon wafer, a plastic substrate plate such as polyethersulfone (PES), polycarbonate (PC), etc., and the type is not particularly limited.

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

According to another embodiment, the color filter may further include an outer coating.

Between the color pixels of the color filter, for the purpose of improving contrast, a grid-like black pattern called a black matrix may be arranged. The material of the black matrix can be chromium. In this case, the following method can be used: chromium is vapor-deposited on the entire glass substrate, and a pattern is formed by etching. However, considering the high cost of the process, the high reflectivity of chromium, and the environmental pollution caused by the chromium waste liquid, a resin black matrix using a pigment dispersion method that can be finely processed can be used.

The black matrix may use black pigment or black dye as a coloring material. For example, carbon black can be used alone, or carbon black can be mixed with coloring pigments. In this case, because coloring pigments with insufficient light-shielding properties are mixed, it has the following advantages: even if the amount of coloring material increases relatively, the strength of the film or the substrate The tightness is also Will not decrease.

A display device including the color filter of this specification is provided.

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

[Example]

Hereinafter, examples are given to explain this specification in detail. The following examples are used to illustrate this specification, and the scope of this specification includes the scope described in the scope of the following patent applications and their replacements and changes, and is not limited to the scope of the examples.

<Manufacturing example>

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

Production of [Compound A]

Put compound A-1 (Benzenesulfonate Dichlorosulfofluorescein (Benzenesulfonate Dichlorosulfofluorescein)) (3 g, 7.40 mmol, 1 eq), compound A-2 (1 eq) into a 100 mL single neck (1-neck) round bottom flask. 2-(Ethylamino)ethanol) (5.28g, 59.22mmol, 8eq), 50g of DI-water, and then stirred at 100°C. Thereafter, the reaction was carried out overnight (12 hours). The reaction was terminated by quenching with 1M hydrochloric acid solution (HCl Solution), and sodium chloride (NaCl) was added to precipitate the reaction product. After filtering the generated precipitate under reduced pressure, it was dried in an oven (Oven) at 80°C. After drying, in order to remove NaCl in the product, it was dissolved in Dimethylformamide (DMF) and filtered, then quenched with diethyl ether and the filtrate was filtered under reduced pressure After that, it was dried to obtain compound A (2.88 g, 5.64 mmol, 76%).

Ionization mode: Atmospheric Pressure Chemical Ionization (APCI)+: m/z=511[M+H]+, Exact Mass: 510.18

Production of [Compound B]

To dichloromethane (Dichloromethane) 75g was added 3,5-Di-tert-butyl-4-hydroxybenzoic acid (3,5-Di-tert-butyl-4-hydroxybenzoic acid) compound A-3 (1.91g, 7.63mmol, 3eq) and stir. Set the ice bath to 0℃, then add N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (N-(3-Dimethylaminopropyl)- N'-ethylcarbodiimide hydrochloride) (EDC-HCl) (1.462 g, 7.63 mmol, 3 eq), stirred for 15 minutes. Add a small amount of dimethylformamide, 4-Dimethyl aminopyridine (DMAP) (0.244g, 2mmol), add compound A (1.3g, 2.545mmol, 1eq), and add it to 0 The reaction was carried out at °C for 2 hours, and the reaction was carried out overnight at room temperature. 150 ml of distilled water and 70 ml of dichloromethane were additionally added to perform extraction, MgSO ₄ was passed through the organic layer to remove water, and the solvent was removed under reduced pressure. After that, the precipitate was separated by column chromatography (Eluent is DMC (dichloromethane): MeOH (Metanol) = 10:1). As a result, compound B (1.36 g, 1.396 mmol) was obtained with a yield of 54.8%.

Ionization mode: APCI+: m/z=743[M+H]+, precise molecular weight: 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. Add 2-Hydroxyethyl Methacrylate (0.488ml, 4.0mmol), and drop N-(3-dimethylaminopropyl)- in CHCl ₃ (10ml) N'-Ethylcarbodiimide (N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide, EDC) (1.15g, 6.0mmol) was reacted at room temperature for 72 hours. After quenching with hydrogen (H ₂ O), it was transferred to a separatory funnel, and the aqueous layer was extracted with CHCl ₃ (chloroform). The organic layer was separated, washed with brine, and dried with Na ₂ SO ₄ . Purification was performed by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane): MeOH (Methanol)=9:1) to obtain compound 1-1 (0.991g) , 1.68mmol, 56%).

Ionization mode: APCI+: m/z=855[M+H]+, precise molecular weight: 854

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

Production of [Compound C]

Add 3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propanoic acid (3-(3,5-Di-tert-butyl-4-hydroxyphenyl)propanoic acid) compound A-4( 2.12g, 7.63mmol, 3eq), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC-HCl) (1.462g, 7.63mmol, 3eq) , Dimethylformamide, 4-dimethylaminopyridine (DMAP) (0.244g, 2mmol), compound A (1.3g, 2.545mmol, 1eq), manufactured in the same manner as in Manufacturing Example 1-2 , Compound C (1.15 g, 1.49 mmol) was obtained with a yield of 58.5%.

Ionization mode: APCI+: m/z=771[M+H]+, precise molecular weight: 770

[Production of Compound 1-4]

Add compound C (1.0g, 1.30mmol), D-MAP (0.487g, 2.0mmol), 2-hydroxyethyl methacrylate (0.317ml, 2.6mmol), EDC (N-(3-dimethylamino Propyl)-N'-ethylcarbodiimide) (1.15 g, 6.0 mmol) was produced by the same method as that of compound 1-1 to obtain 0.84 g (yield 73.0%) of compound 1 -4.

Ionization mode: APCI+: m/z=883[M+H]+, precise molecular weight: 882

<Production Example 3>-Production of Compound 1-6

Production of [Compound D]

Add compound A-1 (benzenesulfonic acid dichlorosulfonic acid luciferin) (3g, 7.40mmol, 1eq) and diethanolamine (3.89g, 37mmol, 5eq), by the same as the manufacture of compound A Method for manufacturing, 3.2 g (yield 79.8%) of compound D was obtained.

Production of [Compound E]

Add 3,5-Di-tert-butyl-4-hydroxybenzoic acid (3,5-Di-tert-butyl-4-hydroxybenzoic acid) compound A-3 (2.54g, 10.16mmol, 4eq) and compound D (1.38 g, 2.54 mmol, 1 eq) was produced in the same manner as the production of compound B, and 1.21 g (yield 47.3%) of compound E was obtained.

Ionization mode: APCI+: m/z=1007[M+H]+, exact molecular weight: 1006

[Production of Compound 1-6]

Compound E (1.0g, 0.99mmol, 1eq) and 2-hydroxyethyl methacrylate (0.36ml, 3mmol, 3eq) were added and manufactured by the same method as that of compound 1-1 to obtain 0.8g (product 65.7%) of compound 1-6.

Ionization mode: APCI+: m/z=1231[M+H]+, exact molecular weight: 1230

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

After dissolving compound B (1g, 1.34mmol, 1eq) in 50ml of dichloromethane, adding sodium hydroxide (0.05g, 1.34mmol, 1eq) and 0.02g of Benzyltrimethyl ammonium (Benzyltrimethyl ammonium) at room temperature After stirring for 30 minutes, 1-chloro-2,3-ethoxypropane (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, then transferred to a separatory funnel, and the aqueous layer was extracted with CHCl ₃ (chloroform). The organic layer was separated, washed with brine, and dried with Na ₂ SO ₄ . After drying under reduced pressure, the organic layer was purified by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane): MeOH (methanol)=9:1) to obtain compound 2-1 (0.65g) , 0.81mmol, 60.7%).

Ionization mode: APCI+: m/z=799[M+H]+, precise molecular weight: 798

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

After dissolving compound B (1g, 1.34mmol, 1eq) in 50ml of dichloromethane, add sodium hydroxide (0.05g, 1.34mmol, 1eq) and 0.02g of benzyltrimethylammonium, at room temperature (25℃) After stirring for 30 minutes, 3-(chloromethyl)-3-methyloxetane (3-(chloromethyl)-3-methyloxetane) (0.32g, 2.68mmol, 2eq) was added and stirred at 40°C for 20 hour. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution, then transferred to a separatory funnel, and the aqueous layer was extracted with CHCl ₃ (chloroform). The organic layer was separated, washed with brine, and dried with Na ₂ SO ₄ . After drying under reduced pressure, the organic layer was purified by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane): MeOH (methanol)=9:1) to obtain compound 3-1 (0.62g) , 0.75mmol, 55.9%).

Ionization mode: APCI+: m/z=828[M+H]+, precise molecular weight: 827

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

After dissolving compound B (1g, 1.34mmol, 1eq) in 50ml of dichloromethane, adding sodium hydroxide (0.05g, 1.34mmol, 1eq) and 0.02g of benzyltrimethylammonium, stirring at room temperature for 30 minutes , Add 2-chloroacetic acid (0.25g, 2.68mmol, 2eq), stir at 40°C for 20 hours. After stirring, the reaction product was quenched with an aqueous hydrochloric acid solution, then transferred to a separatory funnel, and the aqueous layer was extracted with CHCl ₃ (chloroform). The organic layer was separated, washed with brine, and dried with Na ₂ SO ₄ . After drying under reduced pressure, the organic layer was purified by flash silica column chromatography (CH ₂ Cl ₂ (dichloromethane): MeOH (methanol) = 9:1) to obtain compound 4-1 (0.54g) , 0.67mmol, 50.1%).

Ionization mode: APCI+: m/z=801[M+H]+, precise molecular weight: 800

<Comparative example>

Production of the compound of Comparative Example 1

As the compound of Comparative Example 1, Rhodamine B was used.

Production of the compound of Comparative Example 2

Put compound A-1 (fluorescein dichlorosulfonic acid benzenesulfonate) (3g, 7.40mmol, 1eq), 2,6-dimethylaniline (2,6-dimethylaniline) into a 100mL single-neck round bottom flask ) (7.18g, 59.22mmol, 8eq), 20g of NMP, and then stirred at 150°C for 4 hours. After confirmation by thin-layer chromatography (TLC) (dichloromethane: methanol (Methyl alcohol) = 15:1), the reaction solution was cooled to room temperature, and then quenched with 300 ml of 1M HCl solution ( quenching) to terminate the reaction, and add sodium chloride (NaCl) to precipitate the reaction product. After filtering the resulting precipitate under reduced pressure, at 80°C Dry in an oven (Oven). After drying, in order to remove the NaCl in the product, it was dissolved in dimethylformamide (DMF) and filtered, quenched with diethyl ether, filtered the filtrate under reduced pressure, and dried. Comparative Example 2-1 (3.23 g, 5.64 mmol, 76%) of the compound was obtained.

Ionization mode: APCI+: m/z=575[M+H]+, precise molecular weight: 514.19

Into a 100 mL single-necked round-bottomed flask, a compound of Comparative Example 2-1 (3 g, 5.22 mmol, 1 eq), K ₂ CO ₃ (2.885 g, 20.88 mmol, 4 eq), 50 g of NMP was added, and then stirred at room temperature for 10 minute. Add 2-((3-iodopropyl)carbamoyl)benzoic acid (6.955g, 20.88mmol, 4eq), and stir at 95°C for 12 hours. After removing the solvent under reduced pressure, 120 ml of water was added, followed by stirring in an ice water bath for 1 hour. After filtering the precipitate under reduced pressure, it was dried in an oven (Oven) at 80°C. After drying, the precipitate was added to 100 ml of ethyl acetate (Ethyl Acetate), stirred and filtered. After removing 2-((3-iodopropyl)aminomethanyl)benzoic acid and removing the solvent under reduced pressure, the precipitate was dissolved in MeOH and filtered under gravity to obtain Comparative Example 2 of the compound (4.113g) , 4.17mmol, 80%).

Ionization mode: APCI+: m/z=985[M+H]+, precise molecular weight: 984.34

Production of the compound of Comparative Example 3

Into a 100mL single-neck round-bottomed flask, put compound A-1 (benzenesulfonic acid dichlorosulfonic acid fluorescein) (3g, 7.40mmol, 1eq), 2,6-dimethylaniline (7.18g, 59.22mmol) , 8eq), 20g of NMP, stir at 150°C for 4 hours. After confirming by TLC (dichloromethane: methanol (Methyl alcohol) = 15:1), the reaction solution was cooled to room temperature, and then quenched with 300 ml of 1M HCl solution to terminate the reaction, and sodium chloride was added ( NaCl) precipitated the reaction product. After filtering the generated precipitate under reduced pressure, it was dried in an oven (Oven) at 80°C. After drying, in order to remove the NaCl in the product, it was dissolved in dimethylformamide (DMF) and filtered, quenched with diethyl ether, filtered the filtrate under reduced pressure, and dried. Comparative Example 2-1 (3.23 g, 5.64 mmol, 76%) of the compound was obtained.

Ionization mode: APCI+: m/z=575[M+H]+, precise molecular weight: 514.19

Into a 100 mL single-necked round-bottomed flask, a compound of Comparative Example 2-1 (3 g, 5.22 mmol, 1 eq), K ₂ CO ₃ (2.885 g, 20.88 mmol, 4 eq), 50 g of NMP was added, and then stirred at room temperature for 10 minute. 2-((3-iodopropoxy)carbonyl)benzoic acid) (6.976g, 20.88mmol, 4eq) was added and stirred at 95°C for 12 hours. After removing the solvent under reduced pressure, 120 ml of water was added, and then stirred in an ice water bath for 1 hour. After filtering the precipitate under reduced pressure, it was dried in an oven (Oven) at 80°C. After drying, the precipitate was added to 100 ml of ethyl acetate, stirred and filtered. After removing 2-((3-iodopropoxy)carbonyl)benzoic acid and removing the solvent under reduced pressure, the precipitate was dissolved in MeOH and filtered under gravity to obtain Comparative Example 3 of the compound (4.379 g, 4.43 mmol, 85%).

Ionization mode: APCI+: m/z=987[M+H]+, precise molecular weight: 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 1-1, 20.78 parts by weight of binder A as a binder resin, and 20.46 parts of acrylic monomer as a polyfunctional monomer Body of dipentaerythritol hexaacrylate, 0.68 parts by weight of photoinitiator PBG-3057, 0.6 parts by weight of leveling agent F-554, 0.06 parts by weight of adhesion aid KBM-503, 56.57 parts by weight of solvent diacetone alcohol (DAA) are mixed, Example 1 for producing a resin composition.

The adhesive A is a copolymer with a mass ratio of benzyl methacrylate: N-phenyl maleimide: styrene: methacrylic acid = 55:9:11:25.

<Production of Example 2 to Example 6 of Resin Composition>

Except that the compound 1-1 of Example 1 of the resin composition was changed to the compound described in Table 1 below, the resin composition was produced by the same method as that of Example 1 of the resin composition Example 2~Example 6.

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

Except that the compound of Example 1 of the resin composition was changed to the compound described in Table 2 below, the resin composition was produced by the same method as that of Example 1 of the resin composition. Comparative Example 1 to Comparative Example 3.

<Experimental example>

Substrate production

The resin composition manufactured by the above-mentioned Comparative Example 1 to Comparative Example 3 and Example 1 to Example 6 was spin-coated on glass (5cm×5cm), and the pre-heat treatment (Prebake) was performed at 100°C for 100 seconds ,Form a film. After the pre-heat treatment, a post-heat treatment (Post bake) was performed at 230°C for 20 minutes to produce a substrate.

Heat resistance evaluation

For the post-heat treatment (Post bake, one-time) substrate produced under the above-mentioned general conditions, a spectroscope (MCPD, Otsuka) was used to obtain an absorption spectrum in the wavelength range of 380 nm to 780 nm.

In addition, the post-heat treatment substrate (Post bake, once) was additionally processed for 60 minutes at 230°C, and the transmittance spectrum was obtained with the same equipment and the same measurement range.

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

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

A small △Eab value means that the color change is small, which means that it is excellent in heat resistance.

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. From this, it was confirmed that a color filter with excellent heat resistance can be obtained by using the compound represented by the chemical formula 1 described in this specification, that is, the compound represented by the above-mentioned chemical formula 1, which is a dibenzopyran-based dye. Coloring composition and color filter for use.

Chemical resistance evaluation

The substrate was prepared by the method of manufacturing the substrate, and after cutting into 1cm×5cm, two pieces of the substrate cut into 1cm×5cm were immersed in N-methyl-2-pyrrolidone (N-methyl-2-pyrrolidone). pyrrolidone (pyrrolidone) solvent was 16 g, and then an additional baking (Baking) was performed in a convection oven at 80°C for 40 minutes. The absorbance of the solvent from which the substrate sheet was taken out was measured, and the absorbance and the improvement rate (%) of Examples 1 to 6 compared with Comparative Example 1 are described in Table 4 below.

According to Table 3, it was confirmed that the absorbance of Examples 1 to 6 was lower than that of Comparative Example 1 to Comparative Example 3. The lower the absorbance, the better the chemical resistance Excellent. From this, it can be confirmed that by using the compound represented by the chemical formula 1 described in this specification, that is, the dibenzopyran-based dye, which has introduced specific substituents and crosslinkable groups, it is possible to obtain improved solvent resistance. Coloring composition for chemical color filters.

Claims (13)

A compound represented by the following chemical formula 1:

In the chemical formula 1, L1 to L4 are the same or different from each other, and are each independently a direct bond, or a substituted or unsubstituted alkylene group, and Ar1 and Ar2 are the same or different from each other, and are independently hydrogen and deuterium. , Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl; or represented by the following chemical formula 1-A or the following chemical formula 1-B , Wherein when L1 is a direct bond, Ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl; or As represented by the following chemical formula 1-A or the following chemical formula 1-B, when L2 is a direct bond, Ar1 and Ar2 are the same or different from each other, and are each independently hydrogen, deuterium, substituted or unsubstituted alkyl , Substituted or unsubstituted cycloalkyl; or represented by the following chemical formula 1-A or the following chemical formula 1-B, R1~R3 are the same or different from each other and are independently hydrogen, deuterium, hydroxyl, and Substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, r1 and r2 are respectively 1~3 R3 is an integer of 1 to 4. 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; when r3 is 2 or more, R3 is the same or different from each other, and X1 and X2 are the same or different from each other and are represented by the following chemical formula 1-A or the following chemical formula 1-B, respectively,

[Chemical formula 1-B]

In the chemical formula 1-A and the chemical formula 1-B, Q1 and Q2 are the same or different from each other, and are each independently O or NH, and L101 and L102 are the same or different from each other, and are independently direct bonding, substituted, or Unsubstituted alkylene, or substituted or unsubstituted arylalkylene, R101~R105 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl, or A substituted or unsubstituted cycloalkyl group, R106 is any one selected from the following structures and carboxylic acid groups (-COOH),

In the structure, L201 is directly bonded or O, R201~R203 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, r202 is an integer of 1 to 3, and r203 is an integer of 1 to 5. When the r202 is 2 or more, R202 is the same as each other Or different; when the r203 is 2 or more, R203 is the same or different from each other,

Refers to the connecting site, and when at least one of the Ar1 and Ar2 is represented by the chemical formula 1-A, at least one of the X1 and the X2 is represented by the chemical formula 1- As indicated by B, in the case where at least one of the Ar1 and Ar2 is represented by the chemical formula 1-B, at least one of the X1 and the X2 is represented by the chemical formula 1-A Said. The compound described in item 1 of the scope of patent application, wherein said L1 to said L4 are the same or different from each other, and are each independently a direct bond, substituted or unsubstituted methylene, substituted or unsubstituted Ethylene, or substituted or unsubstituted ethylene. The compound described in item 1 of the scope of patent application, wherein said R103 is a hydroxyl group. The compound described in item 1 of the scope of the patent application, wherein the R102 and the R104 are the same or different from each other, and are each independently a substituted or unsubstituted tertiary butyl group. The compound described in item 1 of the scope of patent application, wherein the compound represented by the chemical formula 1 is any one selected from the following compounds:

A compound represented by the following chemical formula 2:

In the chemical formula 2, L1 to L4 are the same or different from each other, and are each independently a direct bond, a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and Ar1 and Ar2 are the same as each other Or different, each independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, or substituted or unsubstituted aryl; or from the following chemical formula 1 -A or the following chemical formula 1-B, R1~R3 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkane Group, substituted or unsubstituted aryl group, or substituted or unsubstituted heterocyclic group, r1 and r2 are each an integer of 1 to 3, r3 is an integer of 1 to 4, when the r1 is 2 or more When R1 is the same or different from each other; when r2 is 2 or more, R2 is the same or different from each other; when r3 is 2 or more, R3 is the same or different from each other,

[Chemical formula 1-B]

In the chemical formula 1-A and the chemical formula 1-B, Q1 and Q2 are the same or different from each other, and are independently O or NH, respectively, and L101 and L102 are the same or different from each other, and are independently direct bonding, substituted, or Unsubstituted alkylene, or substituted or unsubstituted arylalkylene, R101~R105 are the same or different from each other, and are each independently hydrogen, deuterium, hydroxyl, substituted or unsubstituted alkyl, or A substituted or unsubstituted cycloalkyl, R106 is any one selected from the following structures and carboxylic acid groups (-COOH),

In the structure, L201 is directly bonded or O, R201~R203 are the same or different from each other, and are independently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, r202 is an integer of 1 to 3, and r203 is an integer of 1 to 5. When the r202 is 2 or more, R202 is the same as each other Or different; when the r203 is 2 or more, R203 is the same or different from each other,

Refers to the connected part. A polymer containing the compound described in any one of items 1 to 6 in the scope of the patent application as a monomer. A coloring material composition containing the compound described in any one of items 1 to 6 in the scope of the patent application. The coloring material composition as described in item 8 of the scope of patent application further contains at least one of dyes and pigments. The coloring material composition according to item 9 of the scope of patent application, wherein the dye is selected from dibenzopyran dyes, cyanine dyes, anthraquinone dyes, azaporphyrin dyes, and azo metal complex compounds One or more dyes, the pigments are blue pigments or purple pigments. A resin composition comprising: the compound described in any one of items 1 to 6 in the scope of the patent application, a binder resin, a multifunctional monomer, a photoinitiator, and a solvent. A color filter containing the resin composition described in item 11 of the scope of patent application. A display device includes the color filter as described in item 12 of the scope of patent application.