KR102736288B1 - A self emission type photosensitive resin composition, a color conversion layer manufactured by using thereof and a color fiilter comprising the color conversion layer and display device - Google Patents

Abstract

The present invention relates to a self-luminous photosensitive resin composition which can provide excellent fluorescence efficiency by improving luminescence intensity by including a red fluorescent dye and a green fluorescent dye, and at the same time has excellent reliability, a color filter including a color conversion layer using the same, and an image display device.

Description

Self-luminous photosensitive resin composition, color conversion layer manufactured using the same, and color filter and image display device including the same {A SELF EMISSION TYPE PHOTOSENSITIVE RESIN COMPOSITION, A COLOR CONVERSION LAYER MANUFACTURED BY USING THEREOF AND A COLOR FIILTER COMPRISING THE COLOR CONVERSION LAYER AND DISPLAY DEVICE}

The present invention relates to a self-luminous photosensitive resin composition, a color conversion layer manufactured using the same, and a color filter and an image display device including the same.

Recently, the display industry has undergone a rapid change from CRT to flat panel displays such as PDP, OLED, and LCD. Among them, liquid crystal display (LCD) is widely used as a picture display device in almost all industries, and its application range is continuously expanding. However, LCD requires a separate backlight unit due to the absence of its own light-emitting element.

The pigment or dye-based colored color filters used for color implementation in existing liquid crystal displays utilize the characteristics of light absorption and transmission in a specific area for the transmitted backlight light source, and therefore have the problem of a rapid drop in the transmission efficiency of the backlight light source being irradiated.

The light source of a typical backlight unit uses a CCFL (Cold Cathode Fluorescent Lamp). However, backlight units using CCFLs consume a significant amount of power because power must always be supplied to the CCFL, and their disadvantages include a color reproducibility of about 70% of that of CRTs and environmental pollution problems due to the addition of mercury.

As a substitute for solving the above problems, research on backlight units using LED (Light Emitting Diode) has been actively conducted recently. When LED is used as a backlight unit, it can provide consumers with more vivid picture quality by exceeding 100% of the NTSC (National Television System Committee) color reproduction range specifications.

Accordingly, in the same industry, methods are being proposed to change the materials and structures of color filters and LCD panels to improve the efficiency of backlight sources.

For example, Korean Patent Publication No. 10-2010-0056437 discloses a technology for a display using a color conversion layer that uses a fluorescent whitening agent.

However, in the case of the above conventional technology, due to the limitations of the characteristics of the fluorescent whitening agent, when included at a high concentration, not only was the color reproducibility and brightness characteristics reduced, but reliability also deteriorated.

Republic of Korea Patent Publication No. 10-2010-0056437

The present invention aims to solve the above-described problems by providing a self-luminous photosensitive resin composition having excellent reliability in terms of fluorescence efficiency, chemical resistance, solubility, etc.

In addition, the present invention aims to provide a color conversion layer having excellent brightness and color reproducibility and excellent reliability such as chemical resistance, using the self-luminous photosensitive resin composition, and a color filter and an image display device including the same.

The present invention provides a self-luminous photosensitive resin composition comprising a fluorescent dye, wherein the fluorescent dye comprises a green fluorescent dye and a red fluorescent dye, and the green fluorescent dye comprises a compound represented by the following chemical formula 1.

[Chemical Formula 1]

(In chemical formula 1,

R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group,

R ³ to R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,

The above R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ⁹ and R ⁹ and R ¹⁰ can each independently form a substituted or unsubstituted C ₅ to C ₃₀ cycloalkyl ring, a substituted or unsubstituted C 6 to C 30 aromatic ring, a ring including *-CO-O-CO-* or *-CO-N(R ¹¹ )-CO-*,

The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.

* indicates a combined hand.)

In addition, the present invention provides a color conversion layer manufactured using the self-luminous photosensitive resin composition described above.

In addition, the present invention provides a color filter including the color conversion layer described above.

In addition, the present invention provides an image display device including the color filter described above.

The self-luminous photosensitive resin composition according to the present invention can provide excellent fluorescence efficiency by improving luminescence intensity by including a green fluorescent dye and a red fluorescent dye having a specific structure, and in particular, when including a green fluorescent dye and a red fluorescent dye having a specific structure, it also has the advantage of excellent chemical resistance.

Therefore, the color conversion layer of the present invention using the self-luminous photosensitive resin composition exhibits excellent color reproducibility and brightness characteristics, as well as excellent reliability such as solubility and chemical resistance, and thus can be usefully applied to an image display device including a color filter.

FIG. 1 is a drawing illustrating a color filter including a color conversion layer.

The present invention provides a self-luminous resin composition comprising a green fluorescent dye and a red fluorescent dye having a structure of chemical formula 1, a color conversion layer using the same, a color filter comprising the same, and an image display device.

The self-luminous resin composition of the present invention provides a self-luminous photosensitive resin composition capable of improving luminescence intensity by including a green fluorescent dye and a red fluorescent dye of the chemical formula 1 structure, and particularly capable of significantly improving not only luminescence intensity but also solubility and chemical resistance effects by using fluorescent dyes having a specific structure in combination.

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

<Self-luminous photosensitive resin composition>

green fluorescent dye

The present invention provides a benzoperylene compound as a green fluorescent dye represented by Chemical Formula 1. The benzoperylene compound refers to a compound in which an optional substituent is bonded to 1,12-benzoperylene, and a compound in which a substituent having a carbonyl group is bonded to the 3,4 positions and the 9,10 positions of 1,12-benzoperylene is preferred. The carbonyl group of the substituent at the 3,4 positions preferably forms a lactone ring by bonding through an oxygen atom or forms an imide ring by bonding through a nitrogen atom. The carbonyl group of the substituent at the 9,10 positions also preferably forms a lactone ring by bonding through an oxygen atom or forms an imide ring by bonding through a nitrogen atom. As the benzoperylene compound, a compound represented by Chemical Formula (I) (hereinafter referred to as compound (I)) is more preferred.

[Chemical Formula 1]

In formula (I),

R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group or a substituted or unsubstituted C ₁ to C ₃₀ aryl group,

R ³ to R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,

The above R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ⁹ and R ⁹ and R ¹⁰ can each independently form a substituted or unsubstituted C ₅ to C ₃₀ cycloalkyl ring, a substituted or unsubstituted C ₆ to C ₃₀ aromatic ring, a ring including *-CO-O-CO-* or *-CO-N(R ¹¹ )-CO-*,

The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ^11s may be the same or different, and * represents a bond.

The substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon groups represented by R ¹ and R ² and R ¹¹ include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. Aliphatic hydrocarbon groups mean saturated or unsaturated, and can be straight chain, branched chain, or alicyclic.

More specifically, when the substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group is an aliphatic hydrocarbon group, it may be a substituted or unsubstituted C ₁ to C ₃₀ straight-chain alkyl group, a substituted or unsubstituted C ₃ to C ₃₀ branched-chain alkyl group, or a substituted or unsubstituted C ₃ to C ₃₀ cycloalkyl group. The saturated or unsaturated chain hydrocarbon groups represented by R ¹ and R ² and R ¹¹ may be straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl alcohol, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and icosyl, and may be isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, It can be a branched chain alkyl group such as a (3-ethyl)pentyl group, a (1-propyl)pentyl group, a (1-butyl)pentyl group, an isohexyl group, a (5-methyl)hexyl group, a (2-ethyl)hexyl group, a (1-butyl)hexyl group, a (1-pentyl)hexyl group, a (3-ethyl)hemtyl group, a (1-hexyl)heptyl group, a (1-heptyl)octyl group, a (1-octyl)nonyl group, etc., and it can be an alkenyl group such as a vinyl group, a 1-propenyl group, a 2-propenyl group, an allyl group, a (1-methyl)ethenyl group, a 2-propenyl group, a 3-propenyl group, a 1,3-butadionyl group, a (1-(2-propenyl)ethenyl group, a (1,2-dimethyl)propenyl group, a 2-pentyl group, etc.

The saturated or unsaturated aliphatic ring hydrocarbon group represented by R ¹ and R ² and R ¹¹ may include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclopentyl group and cyclooctyl group; cycloalkenyl groups such as cyclohexyl group (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptyl group and cyclooctenyl group; nolbornyl group, adamantane group and bicyclo[2.2.2]octyl group, etc.

Aromatic hydrocarbon groups represented by R ¹ and R ² and R ¹¹ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The hydrocarbon group represented by R ¹ and R ² and R ¹¹ may be a bonded group in which two or more of the chain-like hydrocarbon groups, aliphatic cyclic hydrocarbon groups and aromatic hydrocarbon groups listed above are bonded, as long as the upper limit of the number of carbon atoms is 30 or less. Such a substituent is, for example, a substituent in which at least one or more substituents selected from an aromatic hydrocarbon group and a chain-like hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined, and in the hydrocarbon group by the combination, the chain-like hydrocarbon group can be combined with a divalent group (for example, an alkanediyl group). Examples of hydrocarbon groups by combination include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; aryl alkenyl groups such as phenylethenyl (phenyl vinyl); aryl alkynyl groups such as phenyl-ethynyl; o-tryl, m-tryl, p-tryl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2,3-diisopropylphenyl, 2,4-diisopropylphenyl, 2,5-diisopropyl phenyl group, 2,6-diisopropyl phenyl group, 2,4,6-triisopropyl phenyl group, 4-butyl phenyl group, o-tert-butyl phenyl group, m-tert-butyl phenyl group, p-tert-butyl phenyl group, 2,6-dia(tert-butyl)phenyl group, 3,5-dia(tert-butyl)phenyl group, 3,6-dia(tert-butyl)phenyl group, 4-tert-butyl-2,6-dimethyl phenyl group, 4-pentyl phenyl group, 4-octyl phenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 2-lauryl phenyl group, 3-lauryl phenyl group, 4-lauryl phenyl group, and the like alkyl aryl group; 2,3-dihydro-4-indenyl group, Examples thereof include aryl groups bonded to alkanediyl groups, such as 1,2,3,5,6,7-hexahydro-4-s-indacenyl, 8-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl, and 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl; aryl groups bonded to one or more aryl groups, such as biphenyl and terphenyl; cyclohexylmethylphenyl, benzylphenyl group (dimethyl(phenyl)methyl)phenyl group, and the like. In addition, the hydrocarbon group may be a hydrocarbon group resulting from a combination of, for example, a chain-shaped hydrocarbon group and an aliphatic ring hydrocarbon group. For example, 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group Aliphatic ring hydrocarbon groups having one or more alkyl groups bonded thereto, such as a methylcyclohexyl group, a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, and a 4-cyclohexylhexyl group; alkyl groups having one or more aliphatic ring hydrocarbon groups bonded thereto, such as a cyclopropyl methyl group, a cyclopropyl ethyl group, a cyclobutyl methyl group, a cyclobutyl ethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methyl cyclohexylmethyl group, a cyclohexylethyl group, and adamantylmethyl group;

The aromatic heterocyclic group having 1 to 30 carbon atoms represented by R ¹ and R ² may include an aromatic heterocyclic group containing at least one heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom. Specific examples of the aromatic heterocyclic group include a pyrrol group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinoline group, a thiazolyl group, a benzothiazolyl group, a carbazolyl group, and the like, and the number of carbon atoms may be 2 to 20, and a number of carbon atoms may be more preferable.

The substituent formed by combining the above hydrocarbon group represented by R ¹ and R ² with the above aromatic heterocyclic group may be a substituent in which two or more of the above hydrocarbon groups and aromatic heterocyclic groups are combined. For example, it may be a substituent in which at least one selected from a chain-like hydrocarbon group, an aliphatic ring hydrocarbon group, and an aromatic hydrocarbon group is combined with an aromatic heterocyclic group. The substituent formed by combining may combine a chain-like hydrocarbon group with a divalent linking group (for example, an alkanediyl group).

Examples of groups formed by combining the above hydrocarbon group and the above aromatic heterocyclic group include a 2-methylpyridinyl group, a 4-ethyl-2-methylpyridinyl group, an indole group, a benzimidazole group, a benzopran group, a benzothiophene group, etc.

As substituents (A1) which the hydrocarbon groups having 1 to 30 carbon atoms represented by R ¹ , R ² and R ¹¹ and the aromatic heterocyclic groups having 1 to 30 carbon atoms represented by R ¹ and R ² may have, for example, a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxy group; an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group or an ethoxy group; an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group or a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group; an arylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group or a 2-naphthylthio group; a sulfoxy group; Alkyl sulfoxy groups having 1 to 20 carbon atoms, such as methyl sulfoxy group, ethyl sulfoxy group, etc.; Aryl sulfoxy groups having 6 to 20 carbon atoms, such as phenyl sulfoxy group, 1-naphthyl sulfoxy group, and 2-naphthyl sulfoxy group; Silyl group; Boryl group; Alkyl amino groups having 1 to 20 carbon atoms, such as monomethyl amino group, dimethyl amino group, trimethyl amino group, monoethyl amino group, diethyl amino group, and triethyl amino group; Aryl amino groups having 6 to 20 carbon atoms, such as monophenyl amino group, diphenyl amino group, and triphenyl amino group; Aralkyl amino groups having 7 to 20 carbon atoms, such as benzyl amino group; Carboxy group; Carbamoyl group; Alkyl carbonyl groups having 2 to 20 carbon atoms, such as acetyl group, propionyl group, etc.; Benzoyl group, 1-naphthyl carbonyl group, Examples thereof include aryl carbonyl groups having 7 to 20 carbon atoms, such as 2-naphthyl carbonyl groups; alkoxy carbonyl groups having 2 to 20 carbon atoms, such as methoxy carbonyl groups and ethoxycarbonyl groups; and aryl oxycarbonyl groups having 7 to 20 carbon atoms, such as phenyloxy carbonyl groups, 1-naphthyloxycarbonyl groups, and 2-naphthyloxycarbonyl groups.

Examples of the above halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

From a synthetic point of view, chlorine and bromine atoms are preferred, with bromine atoms being more preferred.

R ¹ , R ² and R ¹¹ include, for example, substituents represented by formulas (D-1) to (D-14) and formulas (G-1) to (G-22). * represents a bond.

It is preferable that R ¹ and R ² independently represent a saturated chain hydrocarbon group which may have a substituent (A1), an aromatic hydrocarbon group which may have a substituent (A1), or a group combining an aromatic hydrocarbon group and a chain hydrocarbon group which may have a substituent (A1). From the viewpoint of solubility in a solvent, the saturated chain hydrocarbon group may be more preferably a saturated branched chain hydrocarbon group. The saturated chain hydrocarbon group may have 1 to 30 carbon atoms, more preferably 1 to 20, and still more preferably 3 to 15. The aromatic hydrocarbon group or the group combining an aromatic hydrocarbon group and a chain hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 15, and still more preferably 8 to 15. In terms of fluorescence intensity, R ¹ and R ² are preferably groups represented by the above formulas (D-4) to (D-14), or formulas (G-5) to (G-22), more preferably a group selected from (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22), and it may be even more preferable that it is a group represented by one of (D-4) to (D-14), (G-7), (G-11), (G-13), (G-15) or (G-16). In addition, it is more preferable when R ¹ and R ² are the same substituent.

R ¹¹ is preferably a saturated chain hydrocarbon group which may have a substituent (A1), an aromatic hydrocarbon group which may have a substituent (A1), or a group combining an aromatic hydrocarbon group and a chain hydrocarbon group which may have a substituent (A1). From the viewpoint of solubility in a solvent, the saturated chain hydrocarbon group is preferably a saturated branched chain hydrocarbon group. The number of carbon atoms in the saturated chain hydrocarbon group may be 1 to 30, preferably 1 to 20, and more preferably 3 to 15. The number of carbon atoms in the aromatic hydrocarbon group or the group combining the aromatic hydrocarbon group and the chain hydrocarbon group is preferably 6 to 20, more preferably 8 to 20, and more preferably 10 to 20. In terms of fluorescence intensity, R ¹¹ is preferably a group represented by the above formulas (D-4) to (D-14), or formulas (G-5) to (G-22), and is more preferably a group represented by one of (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22), and is particularly preferably a group represented by one of (D-4) to (D-14) (G-7), (G-11) (G-13) (G-15), or (G-16).

Also, in cases where R ¹ and R ² are the same group, it is preferable that R ¹¹ have a different group from R ¹ and R ² .

*-OR ¹¹ represented by R ³ ~R ¹⁰ may include an oxy group having the above R ¹¹ , an alkoxy group having 1 to 30 carbon atoms, and an aryloxy group having 1 to 30 carbon atoms. Specifically, examples thereof include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a phenoxy group, and a naphthyloxy group.

*-CO-OR ¹¹ represented by R ³ to R ¹⁰ may include an oxycarbonyl group having the above R ¹¹ , an alkoxycarbonyl group having 1 to 30 carbon atoms, and an aryloxycarbonyl group having 1 to 30 carbon atoms. Specifically, examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a (1-ethyl)pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, a (1-butyl)heptyloxycarbonyl group, an octyloxycarbonyl group, a (1-heptyl)octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, and an icosyloxycarbonyl group. The halogen atoms represented by R ³ to R ¹⁰ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

Examples of rings containing *-CO-O-CO-* or *-CO-N(R ¹¹ )-CO-* formed by R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ respectively (* represents a bond) include divalent groups represented by the following formulas (H- ¹ ) to (H-16) in which R ³ and R ⁴ , R 4 and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ^{9 , and R 9 and} R ¹⁰ are independently divalent groups. In formulas (H-1) to (H-16), * represents the bonds of the benzoperylene skeleton possessed by R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ .

In addition, as the basic group represented by formula (H-9), groups represented by the following formulas (H-9-1) to (H-9-16) are specifically cited. In formulas (H-9-1) to (H-9-16), * represents the bonding hand of the benzoperylene skeleton possessed by R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ .

It is preferred that R ³ and R ⁶ to R ¹⁰ be hydrogen atoms. By appropriately combining R ³ and R ⁶ to R ¹⁰ , a compound having a desired absorption wavelength and fluorescence wavelength can be synthesized.

It is preferred that R ⁴ and R ⁵ independently represent *-OR ¹¹ or *-CO-OR ¹¹ , forming a ring including *-CO-O-CO-* or *-CO-N(R ¹¹ )-CO-* in R ⁴ and R ^5. It is preferred that *-OR ¹¹ or *-CO-OR ¹¹ is an alkoxy group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 1 to 10 carbon atoms in terms of solubility in solvents and fluorescence intensity. In the case where R ⁴ and R ⁵ form a ring including *-CO-O-CO-* or *-CO-N(R ¹¹ )-CO-*, it is more preferable that R ⁴ and R ⁵ form a group represented by a structure selected from the above formulas (H-1) to (H-3) and (H-9) to (H-11), and it is more preferable to form a group represented by the above formulas (H-1) to (H-3) or (H-9-1) to (H-9-16). In terms of solubility in a solvent or fluorescence intensity, it is particularly preferable to form a group represented by any one of the formulas (H-1), (H-9-5), (H-9-6), (H-9-9), (H-9-11), (H-9-12), and (H-9-14) to (H-9-16).

Specific examples of compounds (I) include the compounds shown in Table 1 below.

[Table 1]

In Table 1, H represents a hydrogen atom, and D-6, D-13, G-7, H-1, H-9-6, H-9-9, H-9-11, H-9-12, H-9-14, H-9-15, and H-9-16 represent groups represented by formulas (D-6)(D-13)(G-7),(H-1)(H-9-6),(H-9-9),(H-9-11)(H-9-12)(H-9-14)(H-9-15),(H-9-16), respectively. F-1 represents a sec-butoxycarbonyl group, and F-2 represents a (2-ethyl)hexyloxycarbonyl group.

Among compounds (I), compounds (I-2), (I-3), (I-9), (I-10), (I-12), (I-13), or (I-19) to (I-30) are preferred in terms of solubility in solvents or fluorescence intensity, and compounds (I-3), (I-12), (I-13), or (I-21) to (I-30) are more preferred.

Compound (I) may be preferably a compound represented by formula (Ia).

<Compound represented by formula (Ia)>

[Chemical formula Ia]

Among the formulas (Ia),

R ^1a and R ^2a independently represent an aryl group having 6 to 20 carbon atoms which may optionally have a substituent (A2) and a heteroaryl group having 1 to 20 carbon atoms which may optionally have a substituent (A2).

R ^3a , R ^6a , R ^7a , R ^8a , R ^9a and R ^10a independently represent a hydrogen atom, *-R ^11a , *-O- R ^11a , *-CO-O- R ^11a , a halogen atom, a hydroxy group, a carboxy group or a nitro group.

R ^11a represents a hydrocarbon group having 1 to 20 carbon atoms that may have a substituent (A1), and when there are multiple R ^11a , they may be different from each other.

R ^4a and R ^5a can independently represent *-CO-O- R ^11a , and R ^4a and R ^5a combined represent a group represented by formula (a) or formula (b).

[Chemical formula (a)] [Chemical formula (b)]

Among equations (a) and (b),

R ^b1 and R ^b2 each independently represent a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1).

R ^c1 represents an aryl group having 6 to 20 carbon atoms and a substituent (A2).]

When R ^4a and R ^5a are groups represented by formula (b), R ^1a , R ^2a, and R ^c1 cannot be the same group.

　* indicates a combined hand.】

Aryl groups having 6 to 20 carbon atoms represented by R ^1a , R ^2a , and R ^c1 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, anthryl group, and a pyrenyl group.

Examples of the heteroaryl group having 1 to 20 carbon atoms represented by R ^1a and R ^2a include a furyl group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinoline group, a thiazolyl group, a benzothiazolyl group, a carbazolyl group, etc., and the number of carbon atoms may be 2 to 20, with 3 to 15 being more preferable.

Substituents (A2) that may be present in the aryl base having 6 to 20 carbon atoms represented by R ^1a , R ^2a and R ^c1 and the heteroaryl group having 1 to 20 carbon atoms represented by R ^1a and R ^2a include, for example, a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxy group; an alkyl group having 1 to 20 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group and a tert-butyl group; a cycloalkyl group having 3 to 20 carbon atoms, such as a cyclopropyl group and a cyclobutyl group; an alkenyl group having 2 to 20 carbon atoms, such as a vinyl group and a 1-propenyl group; An aryl group having 6 to 20 carbon atoms, such as a phenyl group or a 1-naphthyl group; an aralkyl group having 7 to 20 carbon atoms, such as a benzyl group or a phenethyl group; an aryl alkenyl group having 8 to 20 carbon atoms, such as a phenyl ethenyl group (phenyl vinyl); an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group or an ethoxy group; an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group, or a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group, or a 2-naphthylthio group; a sulfoxy group; Alkyl sulfoxide groups having 1 to 20 carbon atoms, such as methyl sulfoxide groups and ethyl sulfoxide groups; aryl sulfoxide groups having 6 to 20 carbon atoms, such as phenyl sulfoxide groups, 1-naphthyl sulfoxide groups and 2-naphthyl sulfoxide groups; silyl groups; A boryl group; an alkyl amino group having 1 to 20 carbon atoms, such as a monomethyl amino group, a dimethyl amino group, a trimethyl amino group, a monoethyl amino group, a diethyl amino group, or a triethyl amino group; an aryl amino group having 6 to 20 carbon atoms, such as a monophenyl amino group, a diphenyl amino group, or a triphenyl amino group; an aralkyl amino group having 7 to 20 carbon atoms, such as a benzyl amino group; a carboxyl group; a carbamoyl group; an alkyl carbonyl group having 2 to 20 carbon atoms, such as an acetyl group or a propionyl group; an aryl carbonyl group having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthyl carbonyl group, or a 2-naphthyl carbonyl group; an alkoxy carbonyl group having 2 to 20 carbon atoms, such as a methoxy carbonyl group or an ethoxycarbonyl group; Examples thereof include aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, and a 2-naphthyloxycarbonyl group; heterocyclic groups having 1 to 20 carbon atoms, such as a furyl group, a pyrrolyl group, and a thienyl group; an acetylene group; and an alkanediyl group having 1 to 20 carbon atoms that forms a ring together with at least two carbon atoms among the aryl groups.

The above halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. From a synthetic perspective, chlorine atoms and bromine atoms are preferred, and bromine atoms are more preferred.

It is preferred that R ^1a and R ^2a each independently be an aryl group that may have a substituent (A2). The aryl group preferably has 6 to 15 carbon atoms, more preferably 6 to 10 carbon atoms, and the aryl group may be more preferably a phenyl group. In addition, it is preferred that R ^1a and R ^2a are the same group.

It is preferable that the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms represented by R ^1a and R ^2a have a substituent (A2). As the substituent (A2), an alkyl group having 1 to 20 carbon atoms or a halogen atom is preferred, an alkyl group having 1 to 10 carbon atoms or a halogen atom is more preferred, an alkyl group having 1 to 6 carbon atoms is better, and an alkyl group having 1 to 4 carbon atoms is more preferred.

When the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms represented by R ^1a and R ^2a have a substituent (A2), the number of substituents (A2) is not limited, and may be 1 or 2 or more, and 2 to 4 are more preferable. From the viewpoint of fluorescence intensity, 2 is more preferable. In addition, it is preferable that the substituent (A2) is at least one ortho position, and more preferably at two ortho positions.

When the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms represented by R ^1a and R ^2a have multiple substituents (A2), they may be the same or different.

The number of carbon atoms in the aryl group having the substituent (A2) represented by R ^c1 may be 6 to 15, more preferably 6 to 10, and it is particularly preferable that the aryl group be a phenyl group.

The aryl group having 6 to 20 carbon atoms represented by R ^c1 preferably has a substituent (A2). The substituent (A2) may be preferably an alkyl group having 1 to 20 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 20 carbon atoms that forms a ring together with at least two carbon atoms in the aryl group, and more preferably an alkyl group having 1 to 10 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 10 carbon atoms that forms a ring together with at least two carbon atoms in the aryl group.

In addition, it is more preferable that the aryl group having 6 to 20 carbon atoms represented by R ^c1 has at least one substituent (A2) selected from an alkyl group having 4 to 20 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 20 carbon atoms forming a ring together with at least two carbon atoms of the aryl group.

When an aryl group having 6 to 20 carbon atoms represented by R ^c1 has a substituent (A2), the number of substituents (A2) is not limited, but may be 1 or 2 or more, and 1 to 3 is preferable.

When the aryl group having 6 to 20 carbon atoms represented by R ^c1 has multiple substituents (A2), they may be the same or different.

In R ^11a , R ^b1 and R ^{b2 ,} the hydrocarbon groups having 1 to 20 carbon atoms are exemplified by the same types of hydrocarbon groups represented by R ¹ , R ² and R ¹¹ , except in cases where the number of carbon atoms is 21 or more.

Examples of substituents (A1) that may be present in the hydrocarbon groups having 1 to 20 carbon atoms represented in R ^11a , R ^b1 , and R ^b2 include the same types of substituents (A1) that may be present in the hydrocarbon groups having 1 to 30 carbon atoms represented in R ¹ , R ² , and R ¹¹ .

It may be a saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms which may also have a substituent (A1) as R ^11a . A saturated chain hydrocarbon group having 1 to 20 carbon atoms which may also have a substituent (A1) is preferable, a saturated chain hydrocarbon group having 3 to 15 carbon atoms which may also have a substituent (A1) is more preferable, a branched chain alkyl group having 3 to 15 carbon atoms which may also have a substituent (A1) is more preferable, and still more preferably, it is a group represented by the above formulas (D-4) to (D-14).

R ^b1 and R ^b2 can each independently be a saturated chain hydrocarbon group which may have a substituent (A1), a saturated aliphatic cyclic hydrocarbon group which may have a substituent (A1), or a group combining a chain hydrocarbon group which may have a substituent (A1) and an aliphatic cyclic hydrocarbon group. Of these, a saturated chain hydrocarbon group which may have a substituent (A1) is more preferable. The saturated chain hydrocarbon group is more preferably a saturated straight-chain hydrocarbon group, and the carbon number of the saturated chain hydrocarbon group (more preferably the saturated straight-chain hydrocarbon group) can be 1 to 20, preferably 3 to 20, and more preferably 3 to 10.

In addition, it is preferable that R ^b1 and R ^b2 are groups in which the sum of the number of carbons contained in the two substituents is 6 or more. It is more preferable that R ^b1 and R ^b2 are the same substituent.

*-OR ^11a represented by R ^3a , R ^6a , R ^7a , R ^8a , R ^9a and R ^10a is an example of the same as *-OR ¹¹ represented by R ³ ~R ¹⁰ . *-CO-OR ^11a represented by R ^3a ~R ^10a is an example of the same as *-CO-OR ¹¹ represented by R ³ ~R ¹⁰

The halogen atoms represented by R ^3a , R ^6a , R ^7a , R ^8a , R ^9a and R ^10a are examples of the halogen atoms represented by R ³ to R ¹⁰ . It is preferable that R ^3a , R ^6a , R ^7a , R ^8a , R ^9a and R ^10a be hydrogen atoms from the viewpoint of synthesis. R ^3a , R ^6a , R ^7a , R ^8a , R ^9a and R ^10a can also be combined appropriately to form a compound having a desired absorption wavelength and fluorescence wavelength.

As the base represented by formula (a) in which R ^4a and R ^5a are combined, groups represented by formulae (H-9-5) and (H-9-6) can be specifically mentioned. Among compounds (Ia), compounds represented by formulae (Ii) to (I-iii) may be preferable from the viewpoint of fluorescence intensity or solubility in a solvent.

<<Compound represented by formula (I-i)>>>

[Chemical formula I-i]

Among the formulas (I-i),

R ¹ⁱ to R ⁴ⁱ , R ¹¹ⁱ and R ¹²ⁱ independently represent hydrocarbon groups having 1 to 20 carbon atoms which may have a substituent (A1).

R ⁵ⁱ ~R ¹⁰ⁱ , R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai and R ^10ai independently represent a hydrogen atom, a C 1 to C 20 hydrocarbon group which may have a substituent (A1), a halogen atom, a hydroxyl group, an alkoxy group having 1 to C 10, an aryloxy group having 6 to C 20, a carboxyl group, an alkoxycarbonyl group having 2 to C 20, or a nitro group.

<<Compound represented by formula (I-ii)>>>

[Chemical Formula I-ii]

Among the formulas (I-ii),

R ¹ⁱ to R ⁴ⁱ , R ^b1i and R ^b2i each independently represent a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1).

R ⁵ⁱ ~R ¹⁰ⁱ , R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai and R ^10ai each independently represent a hydrogen atom, a C 1 to C 20 hydrocarbon group which may have a substituent (A1), a halogen atom, a hydroxy group, a C 1 to C 20 alkoxy group, a C 6 to C 20 aryloxy group, a carboxyl group, a C 2 to C 20 alkoxy carbonyl group, or a nitro group.

<<Compound represented by formula (I-iii)>>>

[Chemical formula (I-iii)

Among the formulas (I-iii),

Ar ⁷ⁱ to Ar ⁹ⁱ each independently represent an aryl group having 6 to 20 carbon atoms that may have a substituent (A2). However, all three of Ar ⁷ⁱ to Ar ⁹ⁱ cannot be the same group.

R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai and R ^10ai independently represent a hydrogen atom, a C 1 to C 20 hydrocarbon group which may have a substituent (A1), a halogen atom, a hydroxy group, an alkoxy group having 1 to C 20, an aryloxy group having 6 to C 20, a carboxyl group, an alkoxy carbonyl group having 2 to C 20, or a nitro group.

In formulas (Ii) to (I-iii), the hydrocarbon groups having 1 to 20 carbon atoms represented by R ¹ⁱ to R ¹²ⁱ , R ^3ai , R ^6ai to R ^10ai , R ^b1i and R ^b2i include examples of hydrocarbon groups represented by R ¹ , R ² and R ¹¹ , except when the number of carbon atoms is 21 or more.

Examples of substituents (A1) that may be possessed by the hydrocarbon groups having 1 to 20 carbon atoms represented by R ¹ⁱ to R ¹²ⁱ , R ^3ai , R ^6ai to R ^10ai , R ^b1i and R ^b2i include substituents (A1) that may be possessed by the hydrocarbon groups having 1 to 30 carbon atoms represented by R ¹ , R ² and R ¹¹ .

Examples of aryl groups having 6 to 20 carbon atoms represented by Ar ⁷ⁱ to Ar ⁹ⁱ include aryl groups having 6 to 20 carbon atoms represented by R ^1a , R ^{2a ,} and R ^c1 .

Examples of substituents (A2) that may be possessed by the aryl group having 6 to 20 carbon atoms represented by Ar ⁷ⁱ to Ar ⁹ⁱ include the same examples as the substituents (A2) that may be possessed by the aryl group having 6 to 20 carbon atoms represented by R ^1a , R ^2a , and R ^c1 . Examples of halogen atoms represented by R ⁵ⁱ to R ¹⁰ⁱ , R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai , and R ^10ai include the same examples as the halogen atoms represented by R ³ to R ¹⁰ . Among them, from the viewpoint of synthesis, a chlorine atom or a bromine atom is preferable. Examples of alkoxy groups having 1 to 20 carbon atoms represented by R ⁵ⁱ to R ¹⁰ⁱ , R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai , and R ^10ai include methoxy, ethoxy, propoxy, butoxy, and pentoxy. Examples of aryloxy groups having 6 to 20 carbon atoms represented by R ⁵ⁱ to R ¹⁰ⁱ , R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai , and R ^10ai include phenoxy, 1-naphthyloxy, and 2-naphthyloxy. Examples of the alkoxy carbonyl group having 2 to 20 carbon atoms represented by R ⁵ⁱ to R ¹⁰ⁱ , R ^3ai , R ^6ai , R ^7ai , R ^8ai , R ^9ai , and R ^10ai include a methoxy carbonyl group, an ethoxy carbonyl group, a propoxy carbonyl group, a sec-buto carbonyl group, a tert-butoxy carbonyl group, a butoxy carbonyl group, a pentoxy carbonyl group, a (1-ethyl)pentoxy carbonyl group, a hexyloxy carbonyl group, and a (2-ethyl)hexyloxy carbonyl group.

The green fluorescent dye of the present invention can be produced, for example, by reacting a perylenetetracarboxylic diimide compound with maleic anhydride or maleic anhydride imide in the presence of a dehydrogenator. Among the compounds of chemical formula 1, a compound in which R ⁴ and R ⁵ form a ring including *-CO-O-CO-* (* represents a bond) may be a compound of chemical formula 6.

Examples of perylenetetracarboxylic diimide compounds include N1, N2-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic acid diimide, N1, N2-bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic acid diimide, and N1, N2-bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic acid diimide.

The amount of maleic anhydride or maleic anhydride imide to be used is usually 1 mol or more and 1,000 mol or less per mol of the perylenetetracarboxylic diimide series compound, preferably 1 mol or more and 800-800 mol or less, more preferably 1 mol or more and 600 mol or less, and even more preferably 1 mol or more and 400 mol or less. The above dehydrogenator is one that removes hydrogen from a 6-membered ring compound to aromatize it. Preferred dehydrogenators are chloranil, p-benzoquinone, 2,5-dichloro-p-quinone, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tetramethyl-p-quinone, 2,5-diphenyl-p-quinone, and bromanil, and chloranil 2,3-dichloro-5,6-dicyano-1,4-benzoquinone is more preferred. The reaction temperature is usually between -100 degrees and 300 degrees.

In addition, among the compounds of chemical formula 1, a compound in which R4 and R5 are independently *-CO-OR ^11a (* represents a bonding hand) (hereinafter, a compound of chemical formula 5) can be prepared, for example, by reacting a compound represented by R ¹¹ X and R ¹¹ OH with a compound of chemical formula 6 in a solvent.

Among the compounds of chemical formula 1, a compound (hereinafter, a compound of chemical formula 4) in which R ⁴ and R ⁵ form a ring including *-CO-N(R ¹¹ )-CO-* (* represents a bonding hand) can be produced, for example, by reacting a compound represented by R ¹¹ NH with a compound of chemical formula 6 in a solvent.

Among the compounds represented by R ¹¹ X, X represents a halogen atom, and a chlorine atom or a bromine atom is preferable. The compound represented by R ¹¹ X may be used alone or in combination of two or more, and the compound represented by the formula R ¹¹ OH may also be used alone or in combination of two or more.

The amount of the compound represented by R ¹¹ NH used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, more preferably 1 mol or more and 6 mol or less, and even more preferably 1 mol or more and 4 mol or less, per 1 mol of the compound of chemical formula 6. The solvent is water; Nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol phenol; ether solvents such as diethyl ether and tetrahydrofuran, ketone solvents such as acetone and methyl isobutyl ketone, ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethylsulfoxide, carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid, imidazolium You can hear the back.

When producing any one of the chemical formulas 4 to 6, the amount of the solvent used may be typically 1 to 1000 parts by mass per 1 part by mass of the compound of chemical formula 6.

The manufacturing reaction for manufacturing the green fluorescent dye compound of the present invention can be usually -100°C or higher and 300°C or lower. After the completion of the reaction, the method for obtaining the manufactured compound is not particularly limited, and the compound can be obtained by various known methods. After obtaining, the obtained residue may be purified by column chromatography or recrystallization, etc. The chemical structure of the obtained compound can be analyzed by a known analysis technique and its conditions. Such analysis techniques are not particularly limited, and examples thereof include X-ray crystal structure analysis, mass spectrometry (LC), NMR analysis, and elemental analysis. In the above, R ¹¹ has the same definition as specifically described in this specification.

More specifically, a self-luminous photosensitive resin composition, wherein the compound represented by the chemical formula 1 comprises at least one of the compounds represented by the following chemical formulas 4 to 6.

[Chemical Formula 4]

In the chemical formula 4, R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ alkyl group, or a substituted or unsubstituted C ₁ to C ₃₀ aryl group, and R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group.

The above R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ can each independently form a substituted or unsubstituted C5~C30 cycloalkyl ring, a substituted or unsubstituted C6~C30 aromatic ring,

The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.

* Indicates a combined hand.

The compound represented by the structure of the above chemical formula 4 may be a compound having a structure such as compound (I-23), compound (I-3), compound (I-22), compound (I-24), compound (I-25), compound (I-26), compound (I-27), compound (I-12), compound (I-12), and compound (I-28).

[Chemical Formula 5]

In the above chemical formula 5, R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ straight-chain alkyl group, a substituted or unsubstituted C ₃ to C ₃₀ branched-chain alkyl group, or a substituted or unsubstituted C ₁ to C ₃₀ aryl group.

R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,

The above R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ can each independently form a substituted or unsubstituted C5~C30 cycloalkyl ring, a substituted or unsubstituted C6~C30 aromatic ring,

The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.

* Indicates a combined hand.

Compounds represented by the above chemical formula 5 include compound (I-29), compound (I-30), compound (I-9), etc.

[Chemical formula 6]

(In the above chemical formula 6, R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ straight-chain alkyl group, a substituted or unsubstituted C ₃ to C ₃₀ branched-chain alkyl group, or a substituted or unsubstituted C ₁ to C ₃₀ aryl group,

R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,

The above R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ can each independently form a C5~C30 cycloalkyl ring, a C6~C30 aromatic ring,

The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.

* indicates a combined hand.)

Compounds having a structure represented by the above chemical formula 6 include compound (I-1), compound (I-11), etc.

In the present invention, the content of the benzoperylene compound may be 100 mass% of the total amount of the colorant (A) in terms of fluorescence intensity, and as a lower limit, a value of, for example, 0.1 mass% or more may be sufficient, 5 mass% or more is more preferable, 10 mass% or more is more preferable, 15 mass% or more is more preferable, and 20 mass% or more is more preferable.

Benzoperylene compounds have excellent fluorescence intensity and retention of fluorescence intensity after a heat resistance test compared to perylene compounds used in conventional colored curable resin compositions. Therefore, a color filter formed from a colored curable resin composition containing a benzoperylene compound may tend to have excellent luminescence intensity or brightness. In addition, the retention of fluorescence intensity after a heat resistance test can be measured as the retention of fluorescence intensity before and after a heat test is performed on a color filter formed from a colored curable resin composition. As measurement conditions, for example, a method of maintaining it at about 200 to 250°C for 2 to 6 hours can be mentioned.

red fluorescent dye

In the present invention, it is preferable that the red fluorescent dye include a perylene bisimide compound represented by the following chemical formula 2.

[Chemical formula 2]

In the above chemical formula 2,

R ²¹ is, each independently, a substituted or unsubstituted C ₆ to C ₁₈ aryl group, a substituted or unsubstituted C ₇ to C ₁₈ arylalkyl group, a substituted or unsubstituted C ₁ to C ₁₈ alkoxy group, a substituted or unsubstituted C ₁ to C ₁₀ alcohol group, or a substituted or unsubstituted heterocyclic group having 3 to 30 atoms, and may preferably be a 2,6-diisopropylphenyl group or a 2,4,6-trimethylphenyl group.

R ²² , R ²³ and R ²⁴ are, each independently, hydrogen, C ₁ to It may be a C ₁₀ straight-chain alkyl group, a C ₃ to C ₁₀ branched-chain alkyl group, a substituted or unsubstituted C ₆ to C ₁₈ aryl group, a substituted or unsubstituted C ₇ to C ₁₈ arylalkyl group, a substituted or unsubstituted C ₁ to C ₁₈ alkoxy group, a substituted or unsubstituted C ₁ to C ₁₀ alcohol group, a substituted or unsubstituted heterocyclic group having 3 to 30 atoms, or halogen.

x, y, and z are each independently integers from 0 to 5.

When x, y, and z are integers greater than or equal to 2, R ²² , R ²³ , and R ²⁴ may have the same or different substituents.

R ²⁵ is one selected from the substituents represented by the following chemical formulas 2-1 to 2-3.

[Chemical Formula 2-1]

(In the chemical formula 2-1,

R ²⁶ to R ³⁰ are each independently a hydrogen atom, a hydroxyl group (-OH), a C ₁ to C ₂₀ straight-chain or branched-chain alkyl group substituted or unsubstituted with a halogen atom, a C ₆ to C ₂₀ aryl group, or a C ₁ to C ₁₀ alcohol group,

At least one of the above R ²⁶ to R ³⁰ is a hydroxy group (-OH) or an alcohol group of C ₁ to C ₁₀ .

[Chemical Formula 2-2]

In the above chemical formula 2-2,

R ³¹ to R ³⁹ are each independently a hydrogen atom, a hydroxyl group (-OH), a C ₁ to C ₂₀ straight-chain or branched-chain alkyl group substituted or unsubstituted with a halogen atom, a C ₆ to C ₂₀ aryl group, or a C ₁ to C ₁₀ alcohol group,

At least one of the above R ³¹ to R ³⁹ is a hydroxy group (-OH) or an alcohol group of C ₁ to C ₁₀ .

[Chemical Formula 2-3]

According to the present invention, the perylene bisimide compound can increase fluorescence even at high concentrations by overcoming the steric hindrance effect of the substituent, and can increase solubility in a solvent. In addition, when it includes an alcohol group, it can exhibit excellent chemical resistance, and when it includes a substituent having a structure of chemical formula 2-3, it can provide excellent luminescence efficiency.

In the present specification, “substituted or unsubstituted” means substituted with one or more substituents selected from the group consisting of a halogen group, a nitrile group, a nitro group, a hydroxy group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an aryloxy group, a thiol group, an alkylthio group, an arylthio group, a sulfoxy group, an alkylsulfoxy group, an arylsulfoxy group, a silyl group, a boron group, an arylamine group, an aralkylamine group, an alkylamine group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic group, and an acetylene group, or has no substituents.

As used herein, “halogen group” means -F, -Cl, -Br or -I.

More specifically, the compound of the above chemical formula 2 may include one or more compounds selected from the group consisting of the following chemical formulas 3-1 to 3-21, but is not limited thereto.

[Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3]

[Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6]

[Chemical Formula 3-7] [Chemical Formula 3-8] [Chemical Formula 3-9]

[Chemical Formula 3-10] [Chemical Formula 3-11] [Chemical Formula 3-12]

[Chemical Formula 3-13] [Chemical Formula 3-14] [Chemical Formula 3-15]

[Chemical Formula 3-16] [Chemical Formula 3-17] [Chemical Formula 3-18]

[Chemical Formula 3-19] [Chemical Formula 3-20] [Chemical Formula 3-21]

In the present invention, the content of the red fluorescent dye may be 100 mass% of the total amount of the colorant (A) in terms of fluorescence intensity, and the lower limit may be, for example, 0.01 mass% or more, and it is more preferable if it is 0.1 mass% or more and 20 mass% or less.

Additionally, in the present invention, the content of the fluorescent dye may be included in an amount of 0.01 to 30 wt% based on the total solid weight of the self-luminous photosensitive resin composition.

coloring agent

The self-luminous photosensitive resin composition according to one embodiment of the present invention may further contain a colorant.

The colorant may include at least one selected from the group consisting of organic colorants and/or inorganic colorants, wherein the organic colorant may include an organic pigment and/or an organic dye, and the inorganic colorant may include an inorganic pigment and/or an inorganic dye.

The above colorant may be present in the form of a mill base. The organic pigment and/or organic dye may be a synthetic pigment or a natural pigment. If necessary, the organic pigment may be subjected to a rosin treatment, a surface treatment using a pigment derivative having an acidic group or a basic group introduced therein, a graft treatment on the surface of the pigment using a polymer compound, etc., a fine particle treatment using a sulfuric acid fine particle method, etc., or a washing treatment using an organic solvent or water, etc. to remove impurities. The inorganic pigment may be a metal oxide, a metal complex salt, an inorganic salt of barium sulfate (an adaptor pigment), etc. At this time, the layer exhibiting the main color of the mill base is the same as the pigment used in a conventional mill base.

The colorant may have a particle size of 3 to 150 nm, and when within the above range, it is advantageous to maintain the colorant in a dispersed state in a liquid phase. More specifically, among the colorants, an organic colorant is preferable when the particle size is 20 to 100 nm. When the organic colorant satisfies the above range, it is good in terms of dispersion stability. This is because if the colorant has a size less than the above range, the surface area of the colorant increases rapidly, which reduces dispersion stability and may cause clumping between colorants, and when the colorant has a size exceeding the above range, the weight of the colorant increases, which reduces dispersion stability and makes it easy for precipitation to occur. Among the colorants, an inorganic colorant may have a particle size of 3 to 20 nm. When the inorganic colorant has a size within the above range, it is preferable in terms of excellent dispersibility and increased storage stability.

When the colorant is further included in the self-luminous photosensitive resin composition, the colorant may be included in an amount of 1 to 30 wt%, and more preferably 5 to 20 wt%, based on the total weight of the solid content. When included within the above range, it is preferable in that it is advantageous for expressing coloring.

Binder resin

The self-luminous photosensitive resin composition of the present invention may include a binder resin.

The above binder resin acts as a binder resin for the fluorescent dye, and any binder resin that is soluble in an alkaline developer used in the developing step for manufacturing a color filter may be used without particular limitation.

In one embodiment, the self-luminous photosensitive resin composition according to the present invention may contain a binder resin including a repeating unit represented by the following chemical formula 7 in order to have a fast development speed and no generation of residue when forming a color conversion layer and to improve chemical resistance.

[Chemical formula 7]

In the above chemical formula 7,

A ₁ is hydrogen or a methyl group,

X ₁ is oxygen, sulfur, -SO ₂ -, -SO ₂ NH-, -CO ₂ -, or -CO ₂ NH-,

X ₂ to X ₄ are each independently carbon, oxygen, sulfur or -CO ₂ -,

R ⁴⁰ is a divalent aliphatic hydrocarbon group having C ₁ to C ₂₀ or a divalent aromatic hydrocarbon group having C ₆ to C ₂₀ ,

R ⁴¹ to R ⁴³ are each independently hydrogen, a halogen atom, a C ₁ to C ₂₀ aliphatic hydrocarbon group or a C ₆ to C ₂₀ aromatic hydrocarbon group,

* Indicates a combined hand.

A self-luminous photosensitive resin composition according to one embodiment of the present invention not only has excellent fluorescence efficiency and color conversion ability by including a binder resin including a repeating unit represented by the chemical formula 7, but also has advantages in terms of process such as a fast developing speed when forming a coating film, no residue generation, and excellent chemical resistance, and has advantages in terms of excellent surface properties and chemical resistance of the coating film.

According to one embodiment of the present invention, the binder resin may further include a repeating unit represented by the following chemical formula 8, wherein the repeating unit represented by the following chemical formula 8 may be copolymerized with the repeating unit represented by the above chemical formula 7, but is not limited thereto.

[Chemical formula 8]

In the above chemical formula 8,

_A2 is hydrogen or a methyl group, and * indicates a bond.

In the present invention, when the repeating unit represented by the chemical formula 7 and the repeating unit represented by the chemical formula 8 are copolymerized, there is an advantage in that the properties of the binder resin including them, such as fluorescence efficiency, color conversion rate, or chemical resistance, can be further improved.

In this case, the number of repeating units represented by the chemical formula 7 may be 10 to 100, and the number of repeating units represented by the chemical formula 8 may be 5 to 50, but is not limited thereto.

According to one embodiment of the present invention, the repeating unit represented by the chemical formula 7 may be included in an amount of 5 to 80 wt%, preferably 10 to 60 wt%, and more preferably 25 to 55 wt%, based on 100 wt% of the total copolymer containing the same. When the content of the monomer represented by the chemical formula 7 is included within the above range, there is an advantage of further improving adhesion and chemical resistance.

When the repeating unit represented by the above chemical formula 8 is further included, the repeating unit represented by the above chemical formula 8 may be included in an amount of 15 to 95 wt%, preferably 20 to 70 wt%, and more preferably 20 to 40 wt%, based on 100 wt% of the total copolymer including it. When the content of the monomer represented by the above chemical formula 8 is included within the above range, there is an advantage of further improving the adhesion and chemical resistance.

In addition, the binder resin of the present invention may further include repeating units other than the repeating units of the above-described chemical formulas 7 and/or 8. The repeating units that may further include are not particularly limited as long as they are copolymerizable with the above-described chemical formulas 7 and 8, and for example, aromatic vinyl compounds such as styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, indene, and maleimide, benzylmaleimide, N-phenylmaleimide. Unsaturated imides such as N-cyclohexylmaleimide can be mentioned, and these can be used alone or in combination of two or more.

When the binder resin of the present invention further includes repeating units other than the repeating units of chemical formula 7 and/or chemical formula 8, the content ratio of the constituent units derived therefrom may be included in an amount of 5 to 60 wt%, preferably 10 to 50 wt%, and more preferably 10 to 40 wt%, based on 100 wt% of the total copolymer including them. When the binder resin of the present invention includes repeating units other than the repeating units of chemical formula 7 and/or chemical formula 8 within the above range, there is an advantage in that a pattern can be accurately formed upon development.

The acid value of the binder resin including the repeating unit represented by the above chemical formula 7 may be 0 to 250 (KOHmg/g). The above 'acid value' is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1g of an acrylic polymer and is involved in solubility.

If the acid value of the above-mentioned binder resin is below the above-mentioned range, it may be difficult to secure a sufficient development speed, and if it exceeds the above-mentioned range, the adhesion to the substrate may be reduced, making it easy for a pattern to be short-circuited, and the storage stability of the entire composition may be reduced, causing a problem of an increase in viscosity.

In addition, the weight average molecular weight of the binder resin including the repeating unit represented by the above chemical formula 7 may be 1,000 to 20,000, and when this range is satisfied, the surface hardness of the pattern manufactured through it may be further improved, and not only a high film retention rate but also the solubility of the non-exposed portion in the developer may be further improved, and the resolution may also be improved.

According to one embodiment of the present invention, the above-mentioned binder resin may be included in an amount of 5 to 90 wt%, preferably 10 to 80 wt%, based on the total weight of the solid content of the self-luminous photosensitive resin composition containing it. When the content range of the binder resin is included within the above range, there is an advantage in that the solubility is good, which is advantageous for pattern formation, and the chemical resistance can be further improved.

Photopolymerizable compound

The photopolymerizable compound contained in the self-luminous photosensitive resin composition of the present invention is a compound that can be polymerized by the action of light and a photopolymerization initiator described below, and may include a monofunctional monomer, a difunctional monomer, and other polyfunctional monomers.

Specific examples of monofunctional monomers include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc. Specific examples of difunctional monomers include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc. Specific examples of other polyfunctional monomers include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc. Among these, polyfunctional monomers having two or more functions are preferably used.

The above photopolymerizable compound can be used in a range of usually 5 to 50 mass%, preferably 7 to 45 mass%, based on the total weight of the solid content in the self-luminous photosensitive resin composition. When the photopolymerizable compound is used in a range of 5 to 50 mass% based on the above criteria, the intensity and smoothness of the pixel portion tend to be good, which is preferable.

Photopolymerization initiator

The self-luminous photosensitive resin composition according to one embodiment of the present invention may further contain a photopolymerization initiator.

The photopolymerization initiator is not particularly limited in the present invention, but may include one or more compounds selected from the group consisting of triazine compounds, acetophenone compounds, biimidazole compounds, and oxime compounds.

As the above triazine compounds, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, Examples thereof include 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, etc.

Examples of the above acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, and oligomers of 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1-one.

Examples of the biimidazole compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, and imidazole compounds in which the phenyl group at the 4,4',5,5' position is substituted by a carboalkoxy group. Among these, 2,2'bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole and 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole can be preferably used.

As the above oxime compounds, compounds represented by the following chemical formula 9 may be mentioned.

[Chemical formula 9]

The photopolymerization initiator of the present invention is not limited to those described above, and each of these may be used alone or in combination of two or more.

The content of the above photopolymerization initiator may be usually 0.1 to 40 wt%, preferably 1 to 30 wt%, in terms of weight fraction, based on the solid content, relative to the total amount of the binder resin and the photopolymerizable compound that may be included therewith. When the content of the photopolymerization initiator is included within the above range, the self-luminous photosensitive resin composition containing it may be highly sensitive, so that the strength of the color conversion layer formed using the composition or the smoothness on the surface may be improved.

In addition, the self-luminous photosensitive resin composition of the present invention may further include a photopolymerization initiation assistant together with the above-described photopolymerization initiator. The photopolymerization initiation assistant may be used to further promote the polymerization of the photopolymerizable compound whose polymerization is initiated by the above-described photopolymerization initiator. Examples of the photopolymerization initiation assistant include, but are not limited to, amine compounds, alkoxyanthracene compounds, and thioxanthone compounds.

Examples of the above amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc., and among these, 4,4'-bis(diethylamino)benzophenone can be preferably used.

Examples of the alkoxyanthracene compounds include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, etc. Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, etc.

Examples of the above thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, etc.

As such photopolymerization initiation aids, commercially available ones can also be used. Examples of commercially available photopolymerization initiation aids include the product name “EAB-F” [Manufacturer: Hodogaya Chemical Industry Co., Ltd.].

When these photopolymerization initiation auxiliary agents are further included, the amount used is usually 10 moles or less, preferably 0.01 to 5 moles per mole of the photopolymerization initiator. When within the above range, the sensitivity of the self-luminous photosensitive resin composition is further improved, and the productivity of the color conversion layer formed using the composition can be further improved.

solvent

The solvent contained in the self-luminous photosensitive resin composition of the present invention is not particularly limited, and various organic solvents used in the field of colored photosensitive resin compositions can be used. Specific examples thereof include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; methyl ethyl ketone, acetone, methyl amyl ketone, and methyl isobutyl ketone; Examples include ketones such as cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin, esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone. Among the above solvents, in terms of applicability and drying property, organic solvents having a boiling point of 100°C to 200°C are preferable, and more preferably, alkylene glycol alkyl ether acetates, 3-methoxy-1-butyl acetate, ketones, esters such as ethyl 3-ethoxypropionate or methyl 3-methoxypropionate are preferable, and even more preferably, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, etc. are preferable. These solvents can be used alone or in mixtures of two or more.

The content of the above-mentioned solvent may be included in an amount of 5 to 99 wt%, preferably 10 to 98 wt%, based on 100 wt% of the total weight of the self-luminous photosensitive resin composition containing it. When the content of the above-mentioned solvent is included within the above-mentioned range, the coating property may be improved when applied using a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes also called a die coater), or an inkjet.

The self-luminous photosensitive resin composition according to one embodiment of the present invention may further contain additives in addition to the above-described components.

Additives

The above additives are components that can be added according to the user's needs, and their types are not particularly limited in the present invention, but examples thereof include fillers, other polymer compounds, pigment dispersants, adhesion promoters, antioxidants, ultraviolet absorbers, and anti-coagulants.

The filler may include, for example, glass, silica, alumina, etc.

Specific examples of the other polymer compounds include curable resins such as epoxy resins and maleimide resins, thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane.

As pigment dispersants, commercially available surfactants can be used, and examples thereof include silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, and amphoteric surfactants. These may be used singly or in combination of two or more. As the above surfactants, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl ethers, polyethylene glycol diesters, sorbitan fatty esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethylene imines, etc., and in addition, there are also trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products Co., Ltd.), MEGAFAC (manufactured by Dainippon Ink & Chemical Co., Ltd.), Florad (manufactured by Sumitomo 3M Co., Ltd.), Asahi guard, Surflon (all manufactured by Asahi Glass Co., Ltd.), SOLSPERSE (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by EFKA Chemicals Co., Ltd.), and PB 821 (manufactured by Ajinomoto Co., Ltd.). Can be.

Examples of the adhesion accelerator include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminoprotriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, and the like.

Specific examples of the above ultraviolet absorbent include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzothiazole, alkoxybenzophenone, etc. Specific examples of the anti-coagulant include sodium polyacrylate, etc.

According to one embodiment of the present invention, the additive of the present invention may be an antioxidant.

The above antioxidant may be one selected from the group consisting of phenol-based antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, benzotriazole-based light stabilizers, triazine-based light stabilizers, benzophenone-based light stabilizers, HALs (Hindered Amine Light Stabilizers)-based light stabilizers, and combinations thereof, but is not limited thereto.

In this way, when the self-luminous photosensitive resin composition of the present invention further includes an antioxidant, there is an advantage in that the reliability of a fluorescent dye that may be included together can be improved.

As the above phenol antioxidant, a known compound can be used, and specifically, a phenol compound having a spiro ring skeleton, such as 3,9-bis[2-〔3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy〕-1,1-dimethylethoxy]-2,4,8,10-tetraoxaspiro[5.5]undecane and pentaerythrityl tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate]; 1,3,5,-Trimethyl-2,4,6,-Tris(3'5'-di-t-butyl-4-hydroxybenzyl)benzene, Triethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 4,4'-thiobis(6-t-butyl-3-methylphenol), Tris-(3,5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-Tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, 1,6-Hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,2-Thio-diethylenebis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 2,4-bis[(octylthio)methyl]-O-cresol, 1,6-hexanediol-bis-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], octadecyl-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, 2,2'-methylenebis(4-methyl-6-t-butylphenol), 4,4'-Butylidene-bis(3-methyl-6-t-butylphenol), 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, 1,3,5-tris(4-hydroxybenzyl)benzene, tetrakis[methylene-3-(3,5'-di-t-butyl-4'-hydroxyphenylpropionate)]methane, 3,9-bis[2-〔3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy〕-1,1-dimethylethoxy]-2,4,8,10-tetraoxasaspiro[5.5]undecane, 1,3,5,-trimethyl-2,4,6,-tris(3'5'-di-t-butyl-4-hydroxybenzyl)benzene, Pentaerythrityl tetrakis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], triethylene glycol-bis[3-(3-t-butyl-5-methyl-4-hydroxyphenyl)propionate], 4,4'-thiobis(6-t-butyl-3-methylphenol), tris-(3,5-di-t-butyl-4-hydroxybenzyl)-isocyanurate, 1,3,5-tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanurate, 1,6-hexanediol-bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], 2,2-thio-diethylene bis[3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate], Examples thereof include, but are not limited to, N,N'-hexamethylenebis(3,5-di-t-butyl-4-hydroxy-hydrocinnamamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, 2,4-bis[(octylthio)methyl]-O-cresol, AO-60 (manufactured by Adeka), AO-80 (manufactured by Adeka), etc.

As the above-mentioned antioxidant, a known compound can be used, and specifically, phosphite compounds having a spiro ring skeleton, such as 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, diisodecylpentaerythritol diphosphite, and bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite; 2,2'-Methylenebis(4,6-di-t-butyl-1-phenyloxy)(2-ethylhexyloxy)phosphorus, 6-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenz[d,f][1,3,2]dioxaphosphepin, triphenylphosphite, diphenylisodecylphosphite, phenyldiisodecylphosphite, 4,4'-butylidene-bis(3-methyl-6-t-butylphenylditridecyl)phosphite, octadecylphosphite, tris(nonylphenyl)phosphite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(3,5-di-t-butyl-4-hydroxybenzyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tris(2,4-di-t-butylphenyl)phosphite, cyclic neopentanetetraylbis(2,4-di-t-butylphenyl)phosphite, cyclic neopentanetetraylbis(2,6-di-t-butylphenyl)phosphite, 2,2-methylenebis(4,6-di-t-butylphenyl)octylphosphite, tris(2,4-di-t-butylphenyl)phosphite, Tetrakis(2,4-di-t-butylphenyl)[1,1-biphenyl]-4,4'-diylbisphosphonite, bis[2,4-bis(1,1-dimethylethyl)-6-methylphenyl]ethyl ester, phosphonic acid, 2,2'-methylenebis(4,6-di-t-butyl-1-phenyloxy)(2-ethylhexyloxy)phosphorus, 3,9-bis(2,6-di-tert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane, 6-[3-(3-t-butyl-4-hydroxy-5-methylphenyl)propoxy]-2,4,8,10-tetra-t-butyldibenz[d,f][1,3,2]dioxaphosphepin, HP-10 (Adeka Manufacturing) etc., but are not limited thereto.

As the above-mentioned sulfur-based antioxidant, a known compound can be used, and specifically, compounds having a thioether structure, such as 2,2-bis({[3-(dodecylthio)propionyl]oxy}methyl)-1,3-propanediyl-bis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, dilauryl-3,3'-thiodipropionate, dimyristyl-3,3'-thiodipropionate, distearyl-3,3'-thiodipropionate, and pentaerythrityl-tetrakis(3-laurylthiopropionate); Examples thereof include, but are not limited to, 2-mercaptobenzimidazole, 2,2-bis({[3-(dodecylthio)propionyl]oxy}methyl)-1,3-propanediyl-bis[3-(dodecylthio)propionate], 2-mercaptobenzimidazole, etc.

As the above benzotriazole-based light stabilizer, a known benzotriazole-based derivative can be used and is available from commercial products. Specifically, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2-(2'-hydroxy-5'-tert-butylphenyl)benzotriazole, 2-(2'-hydroxy-3',5-di-tert-butylphenyl)benzotriazole, 2-(2'-hydroxy-5'-tert-octylphenyl)benzotriazole or 2-(2'-hydroxy-3',5'-di-tert-octylphenyl)benzotriazole, or commercially available TINUVIN PS, TINUVIN 99-2, INUVIN 109, TINUVIN 384-2, TINUBIN 571, TINUVIN 900, TINUVIN 928 or TINUVIN 1130 (all manufactured by Ciba Specialty Chemicals, trade names), etc. It can be exemplified.

In addition, as the triazine-based light stabilizer, a hydroxyphenyltriazine-based ultraviolet absorber is preferable. It can be a commercially available one, and examples thereof include TINUVIN 400, TINUVIN 405, TINUVIN 460, TINUVIN479, or TINUVIN1577 (all manufactured by Ciba Specialty Chemicals, trade names).

In addition, as the benzophenone-based light stabilizer, a benzophenone-based derivative known as a light stabilizer can be used, and is available from commercial products. Specifically, examples thereof include 2,4-dihydroxybenzophenone, 2-hydroxy-4-methoxy benzophenone, 2-hydroxy-4-methoxy benzophenone-5-sulfonic acid, 2-hydroxy-4-n-octyloxy benzophenone, 2-hydroxy-4-n-dodecyloxy benzophenone, 2-hydroxy-4-benzyloxy benzophenone, bis(5-benzoyl-4-hydroxy-2-methoxyphenyl)methane, 2,2'-dihydroxy-4-methoxy benzophenone or 2,2'-dihydroxy-4,4'-dimethoxy benzophenone, or commercially available ones such as CHIMASSORB81 (manufactured by Ciba Specialty Chemicals, trade name).

The above HALs light stabilizers can be commercially available, and examples thereof include TINUVIN 123 and TINUVIN 292 from Ciba Specialty Chemicals.

These light stabilizers can be used singly or in combination of two or more, and can preferably be used in combination with a benzotriazole-based, triazine-based or benzophenone-based light stabilizer having a good absorption range of 350 nm or less. Commercially available products include TINUVIN 5050, TINUVIN 5060 or TINUVIN 5151.

According to one embodiment of the present invention, when the antioxidant described above is included as an additive, it may be included in an amount of 0.1 to 10 wt%, preferably 0.2 to 7 wt%, based on 100 wt% of the total weight of the self-luminous photosensitive resin composition including it, and when the content of the antioxidant is included within the above range, there is an advantage in that the fluorescence efficiency of the self-luminous photosensitive resin composition including it can be prevented from being reduced.

In addition, according to one embodiment of the present invention, when the antioxidant is included together with the photopolymerization initiator, the weight ratio of the photopolymerization initiator and the antioxidant may be 1:0.1 to 1:3, and preferably 1:0.2 to 1:0.5. When the weight ratio of the photopolymerization initiator and the antioxidant is less than the above range, the fluorescence efficiency may not be secured, and thus the color conversion ability may be reduced, and when it exceeds the above range, there is a concern that the brightness may be reduced, and therefore it may be desirable to use it appropriately within the above range.

<Color conversion layer>

A color conversion layer according to another aspect of the present invention comprises a cured product of the aforementioned self-luminous photosensitive resin composition.

Since the color conversion layer of the present invention emits light by the light of the light source of the present invention when applied to an image display device, by including a cured product of the self-luminous photosensitive resin composition of the present invention, the dispersibility of the fluorescent dye is improved, thereby improving the fluorescence retention rate, and thus excellent light efficiency can be realized. In addition, since colored light is emitted, the color reproducibility is superior, and since light is emitted in all directions by photoluminescence, not only is the viewing angle improved, but there is also the advantage of excellent chemical resistance.

Referring to FIG. 1, in a conventional image display device including a color conversion layer, white light is transmitted through the color conversion layer to implement color. In this process, some of the light is absorbed by the color conversion layer, so that the light efficiency may be reduced. However, in the case of including a color conversion layer manufactured from the self-luminous photosensitive resin composition of the present invention, the dispersibility of the fluorescent dye is excellent, so that the fluorescence retention rate is improved, so that better light efficiency can be implemented.

<Color Filter>

A color filter according to another aspect of the present invention has the advantages of excellent fluorescence retention rate and excellent chemical resistance by including the color conversion layer described above.

The above color filter includes, in addition to the color conversion layer described above, a substrate and a pattern layer formed on top of the substrate. The substrate may be a substrate of the color conversion layer itself, or may be a portion where the color conversion layer is positioned in a display device or the like, and is not particularly limited in the present invention (see FIG. 1).

The above substrate may be glass, silicon (Si), silicon oxide (SiOx), or a polymer substrate, and the polymer substrate may include, but is not limited to, polyethersulfone (PES) or polycarbonate (PC).

The pattern layer is a layer including the self-luminous photosensitive resin composition of the present invention, and may be a layer formed by applying the self-luminous photosensitive resin composition and exposing, developing, and thermally curing it in a predetermined pattern.

The pattern layer formed by the self-luminous photosensitive resin composition may include a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles. When irradiated with light, the red pattern layer emits red light, the green pattern layer emits green light, and the blue pattern layer emits blue light.

In such cases, the light emitted by the light source is not particularly limited when applied to a display device, but a light source that emits blue light can be used in terms of better color reproducibility.

The above pattern layer may have only two color pattern layers among a red pattern layer, a green pattern layer, and a blue pattern layer. In such a case, the pattern layer may further have a transparent pattern layer.

In the case where only two color pattern layers are provided, a light source that emits light of a wavelength representing the remaining colors not included can be used. For example, in the case where a red pattern layer and a green pattern layer are included, a light source that emits blue light can be used. In such a case, the red fluorescent dye emits red light, the green fluorescent dye emits green light, and the transparent pattern layer emits blue light as it is, representing blue.

The color conversion layer including the substrate and pattern layer as described above may further include a partition formed between each pattern, and may further include a black matrix. In addition, the color conversion layer may further include a protective film formed on the upper portion of the pattern layer.

The present invention can provide a color filter including the color conversion layer.

<Video display device>

The image display device according to the present invention includes the color filter described above. Specifically, the image display device may include a liquid crystal display (LCD), an organic EL display (including an organic EL display, OLED, and QLED), a liquid crystal projector, a display device for a game machine, a display device for a portable terminal such as a mobile phone, a display device for a digital camera, a display device for a car navigation system, and the like, and a color display device is particularly suitable.

The above image display device may further include a configuration known to those skilled in the art, except for having the color filter.

Hereinafter, preferred examples are presented to help understand the present invention, but the following examples are only illustrative of the present invention, and it will be apparent to those skilled in the art that various changes and modifications are possible within the scope and technical idea of the present invention, and it is also natural that such changes and modifications fall within the scope of the appended patent claims.

The "%" and "part" used to indicate content below are by weight unless otherwise specified.

<Examples and Comparative Examples>

Synthesis Example 1: Synthesis of binder resin

Synthesis Example 1-1: Synthesis of binder resin (A-1) of the example

In a four-necked flask equipped with a dropping funnel, a thermometer, a condenser, and a stirrer, a mixed solution of 23.3 g of triethoxy(3-methacryloyloxypropyl)silane (TCI product), 37.5 g of methacrylic acid, 19.0 g of 4-methylstyrene, 225.0 g of propylene glycol methyl ether, and 3.2 g of 2,2'-azobisisobutyronitrile (Wako product) was slowly added dropwise over 1 hour, and polymerization was performed for 8 hours. After cooling to room temperature, a resin (A-1) having a solid content of 18.6 wt%, a weight average molecular weight of 5100, and an acid value of 86 mgKOH/g was synthesized.

Synthesis Example 1-2: Synthesis of binder resin (A-2) of the example

Except for using 3-(Trimethoxysilyl)propyl Methacrylate (TCI product) instead of Triethoxy(3-methacryloyloxypropyl)silane (TCI product) in the above Synthetic Example 1-1, the same composition, content, and method were used, and a resin (A-2) having a solid content of 19.1 wt%, a weight average molecular weight of 9700, and an acid value of 84 mgKOH/g was synthesized.

Synthesis Example 1-3: Preparation of binder resin (A-3) of comparative example

182 g of propylene glycol monomethyl ether acetate was introduced into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube, and the atmosphere inside the flask was changed from air to nitrogen. After the temperature was raised to 100°C, a solution containing 70.5 g (0.40 mol) of benzyl methacrylate, 45.0 g (0.50 mol) of methacrylic acid, 44.5 g (0.10 mol) of a monomethacrylate having an isocyclic skeleton, and 136 g of propylene glycol monomethyl ether acetate to which 3.6 g of azobisisobutyronitrile was added was added dropwise to the flask from the dropping funnel over 2 hours, and stirring was continued for an additional 5 hours at 100°C. Next, the atmosphere inside the flask was changed from nitrogen to air, 30 g of glycidyl methacrylate [0.2 mol, (40 mol% based on the carboxyl group of the methacrylic acid used in this reaction)], 0.9 g of trisdimethylaminomethylphenol, and 0.145 g of hydroquinone were charged into the flask, and the reaction was continued at 110°C for 6 hours to obtain Resin A-3 having a solid acid value of 99 mgKOH/g. The weight average molecular weight converted to polystyrene as measured by GPC was 28,000, and the molecular weight distribution (Mw/Mn) was 2.2, and the GPC measurement conditions are described below.

<GPC measurement conditions>

Device: HLC-8120GPC (manufactured by Dosoh Co., Ltd.)

Column: TSK-GELG4000HXL + TSK-GELG2000HXL (serial connection)

Column temperature: 40℃

Mobile solvent: tetrahydrofuran

Flow rate: 1.0 ㎖/min

Injection volume: 50 ㎕

Detector: RI

Measurement sample concentration: 0.6 mass% (solvent = tetrahydrofuran)

Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (manufactured by Dosoh Co., Ltd.)

The ratio of the weight average molecular weight and the number average molecular weight obtained above was defined as the molecular weight distribution (Mw/Mn).

Synthesis of green fluorescent dye

Synthesis Example 2-1: Preparation of compound (I-21)

　Twenty parts of N1, N2-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic acid diimido (manufactured by Tokyo Chemical Industry Co., Ltd.), 788 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) and 12 parts of p-chloranil (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 170°C for 25 hours. While maintaining the temperature below 70°C, 800 parts of previously prepared 1 mol/L hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 300 parts of acetone (Kanto Chemical) were added, which produced a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the precipitate remaining after filtration was washed with 400 parts of water and 200 parts of methanol. The obtained residue was vacuum-dried at 60°C, and 15 parts of N1,N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride represented by the formula (I-21) (hereinafter referred to as compound (I-21)) were obtained (yield: 75%).

[Compound I-21]

<Identification of compound (I-21)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　８０５

　　　　　　　　　　　　　　Exact Mass: 804.

Synthesis Example 2-2: <Preparation of Compound (I-23)>

In Synthetic Example 2-1, 2.0 parts of N1,N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride, 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) and 120 parts of propionic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and mixed at 140°C for 6 hours, and the resulting mixture was concentrated, and 5 parts of methanol were added, whereupon a yellow precipitate was formed. The mixture including this yellow precipitate was filtered, and the precipitate, after filtration, was washed with 2 parts of methanol. The obtained residue was vacuum-dried at 60°C and purified through a silica gel column (solvent: chloroform), to obtain 1.7 parts of N1, N2, N3-tris(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide represented by the formula (I-23) (hereinafter referred to as compound (I-23)) (yield: 68%).

[Compound I-23]

<Identification of compound (I-23)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　965

　　　　　　　　　　　　　　Exact Mass: 964

　

Synthesis Example 2-3: Preparation of compound (I-1)

1.6 parts of N1, N2-bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic acid diimide (manufactured by Aldrich), 84 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 1.3 parts of p-chloranil (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and mixed at 220°C for 30 hours. While maintaining the temperature below 70°C, 256 parts of previously prepared 1 mol/L hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 96 parts of acetone (Kanto Chemical) were added, whereupon a yellow precipitate was formed. The mixture including the yellow precipitate was filtered, and the precipitate, after filtration, was washed with 400 parts of water and 200 parts of methanol. The obtained residue was vacuum-dried at 60°C, and 1.4 parts of N1,N2-bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride represented by the formula (I-1) (hereinafter referred to as compound (I-1)) were obtained (yield: 75%).

[Compound (I-1)]

<Identification of compound (I-1)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　625

　　　　　　　　　　　　　　Exact Mass: 624

Synthesis Example 2-4: Preparation of compound (I-3)

Except that 2.0 parts of N1,N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride and 0.88 parts of 2,6-diisopropylaniline were changed to 1.4 parts each, in the same manner as in Synthesis Example 2-2, to obtain 1.8 parts of N1,N2-bis(3-pentyl)-N3-(2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter referred to as compound (I-3)) represented by the formula (I-3) (yield: 85%).

　

[Compound (I-3)]

<Identification of compound (I-3)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　784

　　　　　　　　　　　　　　Exact Mass: 783.

Synthesis Example 2-5: Preparation of compound (I-22)

Except that 0.88 part of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1.0 part of 7-tridecamine, 1.4 parts of N1, N2-bis(2,6-diisopropylphenyl)-N3-(7-tridecyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter referred to as compound (I-22)) represented by the formula (I-22) was obtained (yield: 58%) in the same manner as in Synthesis Example 2-2.

[Compound (I-22)]

　

<Identification of compound (I-22)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　987

　　　　　　　　　　　　　　Exact Mass: 986.

Synthesis Example 2-6: Preparation of compound (I-24)

Except that 0.88 part of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1.0 part of 2,5-di-tert-butylaniline, 2.0 parts of N1, N2-bis(2,6-diisopropylphenyl)-N3-(2,5-di-tert-butylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter referred to as compound (I-24)) represented by the formula (I-24) was obtained (yield: 81%) in the same manner as in Synthesis Example 2-2.

[Compound (I-24)]

<Identification of compound (I-24)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　993

　　　　　　　　　　　　　　Exact Mass: 992.

Synthesis Example 2-7: Preparation of compound (I-25)

Except that 0.88 part of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 0.88 part of 4-tert-butyl-2,6-di-methylaniline (manufactured by Aldrich), 2.4 parts of N1,N2-bis(2,6-diisopropylphenyl)-N3-(4-tert-butyl-2,6-dimethylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter referred to as compound (I-25)) represented by the formula (I-25) was obtained (yield: 77%) in the same manner as in Synthesis Example 2-2.

　

[Compound (I-25)]

<Identification of compound (I-25)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　964

　　　　　　　　　　　　　　Exact Mass: 963.

Synthesis Example 2-8: Preparation of compound (I-26)

Except for changing 0.88 parts of 2,6-diisopropylaniline (from Tokyo Chemical Industry Co., Ltd.) to 1.1 parts of 4-bromo-2,6-diisopropylaniline (from Aldrich), 1.7 parts of N1, N2-bis(2,6-diisopropylphenyl)-N3-(4-bromo-2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide represented by the formula (I-26) (hereinafter referred to as compound (I-26)) was obtained (yield: 70%).

[Compound (I-26)]

<Identification of compound (I-26)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　１０４３

　　　　　　　　　　　　　　Exact Mass: 1041

Synthesis Example 2-9: Preparation of compound (I-27)

Except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 0.92 parts of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-amine (manufactured by AmBeed), 1.7 parts of N1,N2-bis(2,6-diisopropylphenyl)-N3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide represented by the formula (I-27) (hereinafter referred to as compound (I-27)) was obtained (yield: 70%) in the same manner as in Synthesis Example 2-2.

[Compound (I-27)]

<Identification of compound (I-27)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　１００４

　　　　　　　　　　　　　　Exact Mass: 1003.

　

Synthesis Example 2-10: Preparation of compound (I-28)

Except that 0.88 parts of 2,6-diisopropylaniline (produced by Tokyo Chemical Industry Co., Ltd.) was replaced with 0.74 parts of 1,2,3,5,6,7-hexahydro-s-indacene-4-amine (manufactured by AChemBlock), 1.6 parts of N1,N2-bis(2,6-diisopropylphenyl)-N3-(1,2,3,5,6,7-hexahydro-s-indacene-4-yl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid toriimido represented by (I-28) (yield: 66%) was obtained.

[Compound (I-28)]

<Identification of compound (I-28)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　960

　　　　　　　　　　　　　　Exact Mass: 959.

Synthesis Example 2-11: Preparation of compound (I-11)

Except that N1,N2-bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic acid diimide was changed to N1,N2-bis(7-tridecyl)perylene-3,4,9,10-tetracarboxylic acid diimide, a synthesis was performed in the same manner as in Synthesis Example 2-3, to obtain 2.1 parts of N1,N2-bis(7-tridecyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride represented by the formula (I-11) (yield: 74%).

[Compound (I-11)]

<Identification of compound (I-11)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　８４９

　　　　　　　　　　　　　　Exact Mass: 848

Synthesis Example 2-12: Preparation of compound (I-12)

Except that 2.0 parts of N1,N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide, 0.88 parts of 2,6-diisopropylaniline, and 1.2 parts of 7-tridecyl amine (from Tokyo Chemical Industry Co., Ltd.) were replaced with 3.0 parts of the above compound (I-11), 2.7 parts of N1,N2,N3-tris(7-tridecyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide represented by (I-12) (yield: 75%) were obtained.

　　 [Compound (I-12)]

　

<Identification of compound (I-12)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　１０３１

　　　　　　　　　　　　　　Exact Mass: 1030

　

Synthesis Example 2-13: Preparation of compound (I-13)

Except that 2.0 parts of N1,N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide was replaced with 3.0 parts of the above compound (I-11) and 0.88 parts of 2,6-diisopropylaniline was replaced with 1.1 parts, in the same manner as in Synthesis Example 2, to obtain 2.9 parts of N1,N2-bis(7-tridecyl)-N3-(2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter referred to as compound (I-13)) represented by the formula (I-13). (Yield: 80%)

[Compound (I-13)]

　

<Identification of compound (I-13)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　１００９

　　　　　　　　　　　　　　Exact Mass: 1008.

Synthesis Example 2-14: Preparation of compound (I-29)

In Synthetic Example 2-1, 5.0 parts of N1,N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride, 6.1 parts of 2-bromobutane (from Tokyo Chemical Industry Co., Ltd.), 4.0 parts of 2-butanol (from Tokyo Chemical Industry Co., Ltd.), and 70 parts of N,N-dimethyl formamide (from Kanto Chemical Industry Co., Ltd.) were added and stirred at 23°C for 1 hour. Then, 4.6 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (from Tokyo Chemical Industry Co., Ltd.) was added dropwise and stirred at 60°C for 6 hours. The obtained mixture was When 30 parts of methanol were added to the concentrate, a yellow precipitate was formed. The mixture including this yellow precipitate was filtered, and the precipitate remaining after filtration was washed with 5 parts of methanol. The obtained residue was vacuum-dried at 60°C and purified using a silica gel column (solvent: chloroform) to obtain 5.0 parts of N1, N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimido-11,12-bis(2-butyl ester) represented by the formula (I-29) (hereinafter referred to as compound (I-29)) (yield: 86%).

　

[Compound (I-29)]

<Identification of compound (I-29)>

(Mass Spectroscopy) Ionization mode = ESI+: m/z = [M+H]+ 935

　　　　　　　　　　　　　　Exact Mass: 934

Synthesis Example 2-15: Preparation of compound (I-30)

Except that 6.1 parts of 2-bromobutane was replaced with 8.2 parts of 1-bromo-2-ethylhexane (from Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 6.7 parts of 2-ethylhexyl alcohol (from Tokyo Chemical Industry Co., Ltd.), 4.9 parts of N1, N2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimido-11,12-bis(2-ethylhexyl) represented by the formula (I-30) (yield: 79%) was obtained.

[Compound I-30]

<Identification of compound (I-30)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　１０４８

　　　　　　　　　　　　　　Exact Mass: 1047.

　

Synthesis Example 2-16: Preparation of compound (I-9)

에서 진공 건조해서 실리카겔 컬럼 정제(용제:클로로포름)한 바, 식(I-9)로 나타내는 N1, N2-비스(3-펜틸)벤조[ghi]페릴렌-2,3,8,9,11,12-헥산 카르복시산-2,3,8,9-비스이미드-11,12-비스(2-부틸 에스테르)(이하, 화합물(I-9)이라 함)을 4.1부 수득하였다(수율 84%).In Synthetic Example 2-3, 4.0 parts of N1,N2-bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride, 6.3 parts of 2-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.1 parts of 2-butanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 56 parts of N,N-dimethyl formamide (manufactured by Kanto Chemical Co., Ltd.) were added and stirred at 23°C for 1 hour. Then, 4.7 parts of 1,8-diazabicyclo[5.4.0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise and stirred at 60°C for 9 hours. The obtained mixture was concentrated to obtain methanol. 31 parts were added, and a yellow precipitate was formed. The mixture including this yellow precipitate was filtered, and the precipitate remaining after filtration was washed with 4 parts of methanol. The residue obtained was 60

By vacuum drying and silica gel column purification (solvent: chloroform), 4.1 parts of N1, N2-bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-butyl ester) represented by the formula (I-9) (hereinafter referred to as compound (I-9)) were obtained (yield: 84%).

[Compound I-9]

<Identification of compound (I-9)>

(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H]+　7555

　　　　　　　　　　　　　　Exact Mass: 754.

Synthesis of red dye

Synthesis Example 3-1: Synthesis of Intermediate Compound (INT)

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride (0.11 mol) and 2,6-diisopropylaniline (0.44 mol) were added to 1 L of propionic acid, the temperature was increased, and the reaction was maintained at 140°C for 5 hours. The reaction solution was cooled to room temperature, the precipitate was filtered under reduced pressure, and washed with methanol. The filtrate was dispersed in water, maintained for 30 minutes, filtered under reduced pressure, and then dispersed again in methanol, maintained for 30 minutes, and filtered under reduced pressure. After drying, the intermediate compound (INT) was obtained with a yield of 80.5%, and the reaction scheme is as follows:

[Reaction Formula 1]

MS (Mass Spectrometric) was measured for the intermediate compound INT formed above using a MALDI-TOF measuring device. As a result, the molecular weight was confirmed to be 848.16.

Synthesis Example 3-2: Synthesis of Intermediate Compound (INT-2)

1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride (0.11 mol) and 2,4,6-trimethylaniline (0.44 mol) were added to 1 L of propionic acid, the temperature was increased, and the reaction was maintained at 140°C for 6 hours. The reaction solution was cooled to room temperature, the precipitate was filtered under reduced pressure, and washed with methanol. The filtrate was dispersed in water, maintained for 30 minutes, filtered under reduced pressure, and then dispersed again in methanol, maintained for 30 minutes, and filtered under reduced pressure. After drying, the intermediate compound (INT-2) was obtained in a yield of 75.5%, and the reaction scheme is as follows:

[Reaction Formula 2]

MS (Mass Spectrometric) was measured for the intermediate compound INT-2 formed above using a MALDI-TOF measuring device. As a result, the molecular weight was confirmed to be 762.06.

Synthesis Example 3-3: Synthesis of dye (chemical formula 3-2)

Potassium carbonate (0.04 mol) was added to the solution of INT (0.04 mol) and N-methylpyrrolidone (266.1 g) prepared in the above Synthesis Example 3-1, and the temperature was raised to 120°C. 4-Hydroethylphenol was added to the reaction solution. (0.04 mol) was dissolved in N-methylpyrrolidone (88.7 g) and stirred at 120°C for 2 hours. After maintaining the reaction at the same temperature for 1 hour, 4-butylphenol (0.16 mol) and potassium carbonate (0.16 mol) were added, and stirring was maintained for 5 hours. The reaction solution was cooled to room temperature and drained into 3 L of distilled water. The resulting purple precipitate was filtered under reduced pressure and washed with methanol. The filtrate was redissolved in methylene chloride (MC), silica filtration was performed to remove impurities, and recrystallization was performed with MeOH to obtain the compound of chemical formula 3-2 with a yield of 54.0%. The reaction scheme at this time is as shown in Reaction Scheme 3 below. MS (Mass Spectrometric) was measured for the compound represented by Chemical Formula 3-2 using a MALDI-TOF measuring device. As a result, the molecular weight was confirmed to be 1290.63.

[Chemical Formula 3-2]

Synthesis Example 3-4: Synthesis of dye (chemical formula 3-3)

Potassium carbonate (0.04 mol) was added to the solution of INT (0.04 mol) and N-methylpyrrolidone (266.1 g) prepared in the above Synthesis Example 3-1, and the temperature was raised to 120°C. 4-Hydroethylphenol was added to the reaction solution. (0.08 mol) was dissolved in N-methylpyrrolidone (88.7 g) and stirred at 120°C for 2 hours. After maintaining the reaction at the same temperature for 1 hour, 4-cumylphenol (0.16 mol) and potassium carbonate (0.16 mol) were added, and stirring was maintained for 4 hours. The reaction solution was cooled to room temperature and drained into 3 L of distilled water. The resulting purple precipitate was filtered under reduced pressure and washed with methanol. The filtrate was redissolved in methylene chloride (MC), silica filtration was performed to remove impurities, and recrystallization was performed with MeOH to obtain the compound of chemical formula 3-3 with a yield of 38.0%. The reaction scheme at this time is as shown in Reaction Scheme 4 below. MS (Mass Spectrometric) was measured for the compound represented by Chemical Formula 3-3 below using a MALDI-TOF measuring device. As a result, the molecular weight was confirmed to be 1402.63.

[Chemical Formula 3-3]

Synthesis Example 3-5: Synthesis of dye (chemical formula 3-6)

Except that 4-fluorophenol was used instead of 4-butylphenol in the above Synthesis Example 3-3, the synthesis was performed using the same method. The compound of Chemical Formula 3-6 was obtained in a yield of 56.0%, and the reaction scheme at this time is as shown in Reaction Scheme 5 below. MS (Mass Spectrometric) was measured for the compound represented by Chemical Formula 3-6 below using a MALDI-TOF measuring device. As a result, the molecular weight was confirmed to be 1176.42.

[Chemical Formula 3-6]

Synthesis Example 3-6: Synthesis of dye (chemical formula 3-10)

Potassium carbonate (0.04 mol) was added to the solution of INT-2 (0.04 mol) and N-methylpyrrolidone (266.1 g) prepared in the above Synthesis Example 3-2, and the temperature was raised to 120°C. 4-Hydroethylphenol was added to the reaction solution. (0.04 mol) was dissolved in N-methylpyrrolidone (88.7 g) and stirred at 120°C for 2 hours. After maintaining the reaction at the same temperature for 1 hour, 4-cumylphenol (0.16 mol) and potassium carbonate (0.16 mol) were added, and stirring was maintained for 4 hours. The reaction solution was cooled to room temperature and drained into 3 L of distilled water. The resulting purple precipitate was filtered under reduced pressure and washed with methanol. The filtrate was redissolved in methylene chloride (MC), silica filtration was performed to remove impurities, and recrystallization was performed with MeOH to obtain the compound of chemical formula 3-10 with a yield of 41.0%. The reaction scheme at this time is as shown in Reaction Scheme 6 below. MS (Mass Spectrometric) was measured for the compound represented by Chemical Formula 3-10 using a MALDI-TOF measuring device. As a result, the molecular weight was confirmed to be 1392.59.

[Chemical Formula 3-10]

Synthesis Example 3-7: Synthesis of dye (chemical formula 3-13)

Potassium carbonate (0.04 mol) was added to the solution of INT (0.04 mol) and N-methylpyrrolidone (266.1 g) prepared in the above Synthetic Example 3-1, and the temperature was raised to 120°C. A solution of 4-methylphenol (0.04 mol) dissolved in N-methylpyrrolidone (88.7 g) was added to the reaction solution at 120°C for 2 hours. After maintaining the reaction at the same temperature for 1 hour, 4-cumylphenol (0.16 mol) and potassium carbonate (0.16 mol) were added, and stirring was maintained for 4 hours. The reaction solution was cooled to room temperature and discharged into 3 L of distilled water. The resulting purple precipitate was filtered under reduced pressure and washed with methanol. After redissolving the filtrate in methylene chloride (MC), silica filtration was performed to remove impurities, and recrystallization was performed with MeOH to obtain the compound of chemical formula 3-13 in a yield of 40.4%.

MS: 1239.49

[Chemical Formula 3-13]

Synthesis Example 3-8: Synthesis of dye (chemical formula 3-14)

Potassium carbonate (0.04 mol) was added to the solution of INT (0.04 mol) and N-methylpyrrolidone (266.1 g) prepared in the above Synthetic Example 3-1, and the temperature was raised to 120°C. A solution of 2,4-dimethylphenol (0.32 mol) dissolved in N-methylpyrrolidone (88.7 g) was added to the reaction solution at 120°C for 2 hours. After maintaining the reaction at the same temperature for 1 hour, 4-cumylphenol (0.32 mol) and potassium carbonate (0.16 mol) were added, and stirring was maintained for 4 hours. The reaction solution was cooled to room temperature and discharged into 3 L of distilled water. The resulting purple precipitate was filtered under reduced pressure and washed with methanol. After redissolving the filtrate in methylene chloride (MC), silica filtration was performed to remove impurities, and recrystallization was performed with MeOH to obtain the compound of chemical formula 3-14 in a yield of 36.0%.

MS: 1281.57

[Chemical Formula 3-14]

Examples and Comparative Examples: Preparation of Self-luminous Photosensitive Resin Composition

A self-luminous photosensitive resin composition was prepared by mixing each component according to the composition shown in Table 2 below. In Table 2 below, the contents of the remaining components, excluding the solvent, are based on the solid content.

[Table 2]

<Composition of Table 2>

A1) Binder resin of Synthesis Example 1-1

A2) Binder resin of Synthesis Example 1-2

A3) Binder resin of Synthesis Example 1-3

B1) I-23 dye of Synthesis Example 2-2

B2) 1-3 dye of synthetic example 2-4

B3) Synthesis Example 2-5 1-22 Dye

B4) 1-24 dye of synthetic example 2-6

B5) 1-25 dye of synthetic example 2-7

B6) Synthesis Example 2-9 1-27 Dye

B7) Synthetic example 2-12 1-12 dye

B8) Synthetic example 2-13 1-13 dye

B9) Synthesis Example 2-14 1-29 dye

B10) Synthetic example 2-15 1-30 dye

B11) Coumarin 6 (TCI)

B12) Coumarin 102 (TCI)

B13) Lumogen Y 083 (BASF)

C1) Synthesis Example 3-3: Fluorescent dye of Chemical Formula 3-2

C2) Synthesis Example 3-4: Fluorescent dye of Chemical Formula 3-3

C3) Synthesis Example 3-5: Fluorescent dye of Chemical Formula 3-6

C4) Synthesis Example 3-6: Fluorescent dye of Chemical Formula 3-10

C5) Synthesis Example 3-7: Fluorescent dye of chemical formula 3-13

C6) Synthesis Example 3-8: Fluorescent dye of chemical formula 3-14

C7) Lumogen R305 (manufactured by BASF)

D) Irgacure OXE01 (manufactured by Ciba Specialty Chemical)

E) Dipentaerythritol hexaacrylate (Kayarad DPHA: manufactured by Nippon Kayaku Co., Ltd.)

F) Propylene glycol monomethyl ether acetate

Manufacturing example: Manufacturing of color conversion layer

Each of the self-luminous photosensitive resin compositions manufactured in the above examples and comparative examples was applied onto a 2 × 2 sized glass substrate by spin coating, and then placed on a heating plate and maintained at a temperature of 100°C for 3 minutes to form a thin film. Subsequently, ultraviolet rays were irradiated onto the thin film. At this time, an ultraviolet light source was used for irradiating light at an exposure dose of 40 mJ/cm2 (365 nm) in an air atmosphere using an ultraviolet light source such as an ultraviolet ray lamp (trade name: USH-250D) manufactured by Ushio Denki Co., Ltd., and no special optical filter was used. The ultraviolet-irradiated thin film was developed for 60 seconds using a spray developer with a KOH aqueous solution having a pH of 12.5, and then heated in a heating oven at 220°C for 20 minutes to manufacture a pattern. The thickness of the self-luminous color conversion layer pattern manufactured above was 2.0 μm.

Experimental Example 1. Luminescence intensity

For each color conversion layer manufactured in the above manufacturing example, the luminescence intensity of each color conversion layer was measured using a quantum efficiency meter (QE-1000, manufactured by Otsuka Corporation), and the results are shown in Table 3 below. At this time, it can be judged that the higher the measured luminescence intensity, the better the luminance characteristics are.

Experimental Example 2. Heat Resistance Evaluation

The heat resistance of each color conversion layer manufactured in the above manufacturing example was evaluated by comparing the color change before and after heating for 120 minutes at 230℃. At this time, the following mathematical expression 1 used represents the color change in the three-dimensional chromaticity system defined by L*, a*, and b*. (Color Science Handbook (Showa 60), New Edition, edited by the Japan Color Society, p. 266).

[Mathematical Formula 1]

△Eab={(△L) ² +(△a) ² +(△b) ² } ^1/2

<Evaluation criteria>

○: △Eab is less than 2

×: △Eab is 2 or more

Experimental Example 3. Chemical Resistance

Chemical resistance evaluation was conducted on each of the color filters manufactured above. Chemical resistance was evaluated by measuring the color change value (△E*ab) before and after precipitation when precipitating in an NMP solution at 60℃ for 60 minutes. △E*ab is a value required by the following saturation formula according to the CIE 1976 (L*, a*, b*) space colorimetric system (Color Science Handbook (Showa 60) P.266, newly edited by the Japan Society of Color Research). The evaluation criteria for chemical resistance are as follows, and the results are shown in Table 3 below.

<Evaluation criteria>

○: △E*ab: 3 or less

△: △E*ab: 3 or more and 10 or less

×: △E*ab: Over 10

Experimental Example 4. Solubility Evaluation

The dye was evaluated based on the wt% dissolved in PGMEA. The evaluation criteria are as follows, and the results are shown in Table 3 below.

<Evaluation criteria>

○: 3wt% or more

△: 3wt% or more and 1wt% or less

×: 1wt% or less

[Table 3]

In the case of Examples 1 to 11, it was confirmed that excellent luminescence intensity, reliability of heat resistance and chemical resistance, and excellent solubility were satisfied by including the red dye and green fluorescent dye having the specific structure of the present invention. On the other hand, in the case of Comparative Examples 1 and 3 including the conventional green fluorescent dye even when the red fluorescent dye of the present invention was included, it was confirmed that the luminescence intensity was significantly lowered compared to the present invention, and in the case of Comparative Examples 2 and 3 using only A3 resin, the effect of reduced chemical resistance was confirmed. In addition, in the case of Comparative Example 4 including the conventional RED BASF R305, it was confirmed that sufficient dissolution did not occur in the solvent composition of PGMEA due to the low solubility of the red fluorescent dye, making it impossible to evaluate.

Claims (12)

A self-luminous photosensitive resin composition containing a fluorescent dye,
The above fluorescent dyes include green fluorescent dyes and red fluorescent dyes,
The above green fluorescent dye comprises a compound represented by the following chemical formula 1,
The above self-luminous composition further comprises at least one selected from the group consisting of a photopolymerizable compound; a photopolymerization initiator; a binder resin and a solvent.
The above-mentioned binder resin is a self-luminous photosensitive resin composition comprising a repeating unit represented by the following chemical formula 7:
[Chemical Formula 1]

(In chemical formula 1,
R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group,
R ³ to R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,
The above R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ , R ⁷ and R ⁸ , R ⁸ and R ⁹ and R ⁹ and R ¹⁰ can each independently form a substituted or unsubstituted C ₅ to C ₃₀ cycloalkyl ring, a substituted or unsubstituted C 6 to C 30 aromatic ring, a ring including *-CO-O-CO-* or *-CO-N(R ¹¹ )-CO-*,
The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.
* indicates a combined hand.)
[Chemical formula 7]

(In the above chemical formula 7,
A ₁ is hydrogen or a methyl group,
X ₁ is oxygen, sulfur, -SO ₂ -, -SO ₂ NH-, -CO ₂ -, or -CO ₂ NH-,
X ₂ to X ₄ are each independently carbon, oxygen, sulfur or -CO ₂ -,
R ⁴⁰ is a divalent aliphatic hydrocarbon group having C ₁ to C ₂₀ or a divalent aromatic hydrocarbon group having C ₆ to C ₂₀ ,
R ⁴¹ to R ⁴³ are each independently hydrogen, a halogen atom, a C ₁ to C ₂₀ aliphatic hydrocarbon group or a C ₆ to C ₂₀ aromatic hydrocarbon group,
* indicates a combined hand.) In claim 1,
A self-luminous photosensitive resin composition, wherein the red fluorescent dye comprises a compound represented by the following chemical formula 2.
[Chemical formula 2]

(In the above chemical formula 2,
R ²¹ is, each independently, a substituted or unsubstituted C ₆ to C ₁₈ aryl group, a substituted or unsubstituted C ₇ to C ₁₈ arylalkyl group, a substituted or unsubstituted C ₁ to C ₁₈ alkoxy group, a substituted or unsubstituted C ₁ to C ₁₀ alcohol group, or a substituted or unsubstituted heterocyclic group having 3 to 30 atoms,
R ²² , R ²³ and R ²⁴ are, each independently, hydrogen, C ₁ to A C ₁₀ straight chain alkyl group, a C ₃ to C ₁₀ branched chain alkyl group, a substituted or unsubstituted C ₆ to C ₁₈ aryl group, a substituted or unsubstituted C ₇ to C ₁₈ arylalkyl group, a substituted or unsubstituted C ₁ to C ₁₈ alkoxy group, a substituted or unsubstituted C ₁ to C ₁₀ alcohol group, a substituted or unsubstituted heterocyclic group having 3 to 30 atoms, or a halogen,
x, y, and z are each independently integers from 0 to 5,
When x, y, z are integers greater than or equal to 2, R ²² , R ²³ , and R ²⁴ may have the same or different substituents,
R ²⁵ is one selected from the substituents represented by the following chemical formulas 2-1 to 2-3.)
[Chemical Formula 2-1]

(In the above chemical formula 2-1,
R ²⁶ to R ³⁰ are each independently a hydrogen atom, a hydroxyl group (-OH), a C ₁ to C ₂₀ straight-chain or branched-chain alkyl group substituted or unsubstituted with a halogen atom, a C ₆ to C ₂₀ aryl group, or a C ₁ to C ₁₀ alcohol group,
At least one of the above R ²⁶ to R ³⁰ is a hydroxy group (-OH) or an alcohol group of C ₁ to C _10. )
[Chemical Formula 2-2]

(In the above chemical formula 2-2,
R ³¹ to R ³⁹ are each independently a hydrogen atom, a hydroxyl group (-OH), a C ₁ to C ₂₀ straight-chain or branched-chain alkyl group substituted or unsubstituted with a halogen atom, a C ₆ to C ₂₀ aryl group, or a C ₁ to C ₁₀ alcohol group,
At least one of the above R ³¹ to R ³⁹ is a hydroxy group (-OH) or an alcohol group of C ₁ to C _10. )
[Chemical Formula 2-3]
In claim 2,
A self-luminous photosensitive resin composition, wherein the compound represented by the chemical formula 2 comprises a structure of a compound selected from the group consisting of the following chemical formulas 3-1 to 3-21:
[Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3]

[Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6]


[Chemical Formula 3-7] [Chemical Formula 3-8] [Chemical Formula 3-9]

[Chemical Formula 3-10] [Chemical Formula 3-11] [Chemical Formula 3-12]

[Chemical Formula 3-13] [Chemical Formula 3-14] [Chemical Formula 3-15]

[Chemical Formula 3-16] [Chemical Formula 3-17] [Chemical Formula 3-18]

[Chemical Formula 3-19] [Chemical Formula 3-20] [Chemical Formula 3-21]
In claim 1,
A self-luminous photosensitive resin composition, wherein the compound represented by the chemical formula 1 comprises at least one of the compounds represented by the following chemical formulas 4 to 6.
[Chemical Formula 4]

(In the above chemical formula 4, R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ straight-chain alkyl group, a substituted or unsubstituted C ₃ to C ₃₀ branched-chain alkyl group, or a substituted or unsubstituted C ₁ to C ₃₀ aryl group,
R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,
The above R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ can each independently form a C5~C30 cycloalkyl ring, a C6~C30 aromatic ring,
The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.
* indicates a combined hand.)
[Chemical Formula 5]

(In the above chemical formula 5, R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ straight-chain alkyl group, a substituted or unsubstituted C ₃ to C ₃₀ branched-chain alkyl group, or a substituted or unsubstituted C ₁ to C ₃₀ aryl group,
R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,
The above R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ can each independently form a substituted or unsubstituted C5~C30 cycloalkyl ring, a substituted or unsubstituted C6~C30 aromatic ring,
The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.
* indicates a combined hand.)
[Chemical formula 6]

(In the above chemical formula 6, R ¹ and R ² each independently represent a substituted or unsubstituted C ₁ to C ₃₀ straight-chain alkyl group, a substituted or unsubstituted C ₃ to C ₃₀ branched-chain alkyl group, or a substituted or unsubstituted C ₁ to C ₃₀ aryl group,
R ³ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, *-R ¹¹ , *-OR ¹¹ , *-CO-OR ¹¹ , a halogen atom, a hydroxyl group, a carboxyl group or a nitro group,
The above R ⁷ and R ⁸ , R ⁸ and R ⁹ , and R ⁹ and R ¹⁰ can each independently form a C5~C30 cycloalkyl ring, a C6~C30 aromatic ring,
The above R ¹¹ represents a substituted or unsubstituted C ₁ to C ₃₀ hydrocarbon group, and when there are multiple R ^11s , R ¹¹ may be the same or different.
* indicates a combined hand.)
delete In claim 1,
A self-luminous photosensitive resin composition, wherein the self-luminous composition further contains a colorant.
delete In claim 1, the binder resin further comprises a repeating unit represented by the following chemical formula 8, a self-luminous photosensitive resin composition:
[Chemical formula 8]

In the above chemical formula 8,
A ₂ is hydrogen or a methyl group,
* Indicates a combined hand.
A self-luminous photosensitive resin composition according to claim 1, wherein the fluorescent dye is contained in an amount of 0.01 to 30 wt% based on the total solid content weight of the self-luminous photosensitive resin composition.
A color conversion layer manufactured from a self-luminous photosensitive resin composition according to any one of claims 1 to 4, 6, 8 and 9.
A color filter comprising the color conversion layer of claim 10. An image display device comprising a color filter according to claim 11.