Compound and pigment dispersion comprising same

Abstract

A compound and a pigment dispersion comprising same are provided.

Description

Compound and pigment dispersion containing the same

[0001] The present invention relates to a pigment synergist compound and a pigment dispersion containing the same.

[0002]

[0003] Liquid crystal display devices, which are one type of display devices, have advantages such as being lightweight, thin, low-cost, low-power driveability, and excellent compatibility with integrated circuits, and their range of use is expanding for laptop computers, monitors, and TV images. Such liquid crystal display devices are composed of a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, and an active circuit portion composed of a liquid crystal layer, a thin film transistor, and a capacitor layer, and an upper substrate on which the ITO pixel electrode is formed. The color filter has a structure in which a black matrix layer is formed in a set pattern on a transparent substrate to block light at the boundary between pixels, and a pixel portion in which a plurality of colors, typically the three primary colors of red (R), green (G), and blue (B), are arranged in a set order to form each pixel, are sequentially stacked.

[0004] The pigment dispersion method, which is one of the methods for implementing a color filter, is a method in which a colored thin film is formed by coating a photopolymerizable composition containing a coloring agent on a transparent substrate provided with a black matrix, exposing a pattern of a desired shape, removing the unexposed area with a solvent, and repeating a series of processes such as thermal curing. The colored photosensitive resin composition used in the manufacture of a color filter according to the pigment dispersion method is generally composed of an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives. The pigment dispersion method is actively applied in the manufacture of LCDs for mobile phones, laptops, monitors, TVs, etc.

[0005] Image sensors are image capturing components that generate images in mobile phone cameras and digital still cameras (DSCs). Depending on their manufacturing process and application, they can be broadly classified into solid-state image sensors (charge-coupled device (CCD)) and complementary metal oxide semiconductor (CMOS) image sensors. Color image capturing devices used in solid-state image sensors or complementary metal oxide semiconductors typically install color filters with filter segments of red, green, and blue additive primary colors on the light-receiving element to perform color separation. Recently, the pattern size of the color filters mounted on these color image capturing devices is 2㎛ or less, which is 1 / 100 to 1 / 200 times the size of the color filter pattern for existing LCDs. Accordingly, increasing the resolution and reducing residue are important factors that determine the performance of the device.

[0006] Meanwhile, color filters manufactured using pigment-type photosensitive resin compositions suffer from limitations in brightness and contrast ratio due to the size of the pigment particles. Furthermore, color imaging elements for image sensors require a smaller particle size to form fine patterns. To address these needs, attempts have been made to introduce non-particle dyes instead of pigments, creating photosensitive resin compositions suitable for the dyes, thereby achieving color filters with improved brightness and contrast ratio. However, dyes, compared to pigments, have lower durability in light and heat resistance, raising concerns about reduced brightness.

[0007]

[0008] One embodiment is to provide a novel structural synergistic compound capable of implementing ultra-thin, ultra-fine patterning.

[0009] Another embodiment is to provide a pigment dispersion comprising the compound.

[0010]

[0011] One embodiment provides a compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),

[0016] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group, the following chemical formula L-1, or a combination thereof,

[0017] [Chemical formula L-1]

[0018]

[0019] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0020] R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a basic group, provided that R 1 Inland R 4 At least one of them is a basic group,

[0021] n is an integer of 1 or 2, and the above L 2is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 If directly connected, n is an integer of 2.

[0022] The above basic group is *-NR b R c (R b and R c Each independently represents a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group), and may be of the following chemical formula B-1 or the following chemical formula B-2.

[0023] [Chemical Formula B-1]

[0024]

[0025] [Chemical Formula B-2]

[0026]

[0027] In the above chemical formula B-1 and chemical formula B-2,

[0028] R d and R e are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.

[0029] The above R a may be a hydrogen atom.

[0030] The above chemical formula 1 can be represented by the following chemical formula 1A or chemical formula 1B.

[0031] [Chemical Formula 1A]

[0032]

[0033] [Chemical Formula 1B]

[0034]

[0035] In the above chemical formulas 1A and 1B,

[0036] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),

[0037] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group, the following chemical formula L-1, or a combination thereof,

[0038] [Chemical formula L-1]

[0039]

[0040] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0041] R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a basic group,

[0042] n is an integer of 1 or 2, and the above L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 If it is directly connected, n is an integer of 2.

[0043] The above R 1 Inland R 4 At least two of them can be basic groups.

[0044] The above R 1 Inland R 4 At least three of them can be basic groups.

[0045] The above basic groups may be of the same type.

[0046] The above basic groups may be of different types.

[0047] The above compound can be represented by any one of the following chemical formulas 1-1 to 1-17.

[0048] [Chemical Formula 1-1]

[0049]

[0050] [Chemical Formula 1-2]

[0051]

[0052] [Chemical Formula 1-3]

[0053]

[0054] [Chemical Formula 1-4]

[0055]

[0056] [Chemical Formula 1-5]

[0057]

[0058] [Chemical Formula 1-6]

[0059]

[0060] [Chemical Formula 1-7]

[0061]

[0062] [Chemical Formula 1-8]

[0063]

[0064] [Chemical Formula 1-9]

[0065]

[0066] [Chemical Formula 1-10]

[0067]

[0068] [Chemical Formula 1-11]

[0069]

[0070] [Chemical Formula 1-12]

[0071]

[0072] [Chemical Formula 1-13]

[0073]

[0074] [Chemical Formula 1-14]

[0075]

[0076] [Chemical Formula 1-15]

[0077]

[0078] [Chemical Formula 1-16]

[0079]

[0080] [Chemical Formula 1-17]

[0081]

[0082] The above compound may be a pigment synergist.

[0083] The above compound may be a yellow pigment synergist.

[0084] Another embodiment provides a pigment dispersion comprising the compound and the pigment.

[0085] The above pigment may be a yellow pigment.

[0086] The above pigment dispersion may further include a dispersant, a dispersing resin, and a solvent.

[0087] The pigment dispersion may include 0.5 wt% to 5 wt% of the compound; 5 wt% to 20 wt% of the pigment; 1 wt% to 5 wt% of the dispersant; 3 wt% to 10 wt% of the dispersion resin; and the remainder of the solvent, based on the total amount of the pigment dispersion.

[0088] Specific details of other embodiments of the present invention are included in the detailed description below.

[0089]

[0090] The compound according to one embodiment is a yellow pigment synergist, which can ultimately realize a color resist and CMOS image sensor capable of ultra-thin, ultra-fine patterning.

[0091]

[0092] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0093] Unless otherwise specified herein, "substitution" means that at least one hydrogen atom in a compound is substituted with a halogen atom (F, Cl, Br, I), a hydroxy group, a C1 to C20 alkoxy group, a nitro group, a cyano group, an amine group, an imino group, an azido group, an amidino group, a hydrazino group, a hydrazono group, a carbonyl group, a carbamyl group, a thiol group, an ester group, an ether group, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid or a salt thereof, a C1 to C20 alkyl group, a C2 to C20 alkenyl group, a C2 to C20 alkynyl group, a C6 to C30 aryl group, a C3 to C20 cycloalkyl group, a C3 to C20 cycloalkenyl group, a C3 to C20 cycloalkynyl group, a C2 to C20 heterocycloalkyl group, a C2 to C20 heterocycloalkenyl group, It means substituted with a C2 to C20 heterocycloalkynyl group or a combination thereof.

[0094] Unless otherwise specified herein, the terms “heterocycloalkyl group,” “heterocycloalkenyl group,” “heterocycloalkynyl group,” and “heterocycloalkylene group” mean that at least one N, O, S, or P heteroatom is present in the ring compound of cycloalkyl, cycloalkenyl, cycloalkynyl, and cycloalkylene, respectively.

[0095] Unless otherwise specified herein, “(meth)acrylate” means both “acrylate” and “methacrylate”.

[0096] Unless otherwise specified herein, “combination” means mixing or copolymerization.

[0097] Unless otherwise defined in the chemical formulas herein, if a chemical bond is not drawn at a position where a chemical bond should be drawn, it means that a hydrogen atom is bonded at that position.

[0098] Additionally, unless otherwise specified herein, “*” means a portion connected to the same or different atoms or chemical formulas.

[0099]

[0100] A compound according to one embodiment is represented by the following chemical formula 1.

[0101] [Chemical Formula 1]

[0102]

[0103] In the above chemical formula 1,

[0104] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),

[0105] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group, the following chemical formula L-1, or a combination thereof,

[0106] [Chemical formula L-1]

[0107]

[0108] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0109] R 1 Inland R 4are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a basic group, provided that R 1 Inland R 4 At least one of them is a basic group,

[0110] n is an integer of 1 or 2.

[0111] For example, in the chemical formula 1 above, L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 If directly connected, n can be an integer of 2.

[0112] For example, in the above chemical formula 1, n is an integer of 1 or 2, and L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 n is an integer of 2 only when directly connected to , otherwise n can be an integer of 1.

[0113] To facilitate the stable dispersion and miniaturization of pigment dispersions, various studies are being conducted to create pigments with particles of a certain size through processes such as salt milling using synthetically obtained pigments. However, as mentioned above, color filters manufactured with pigment-type photosensitive resin compositions have limitations in brightness and contrast ratio due to the size of the pigment particles. Furthermore, color imaging elements for image sensors require a smaller particle size to form fine patterns. To meet these needs, there is a growing need for compounds necessary for finely dispersing pigment particles and creating dispersions containing pigments that do not reaggregate, and for manufacturing photosensitive resin compositions for color filters using dispersions containing such compounds.

[0114] Color filters manufactured from pigment-type photosensitive resin compositions have limitations in their tinting power due to the size of the pigment particles. Furthermore, for applications in image sensors, resin compositions comprising smaller particles are required for fine pattern formation. Furthermore, for applications in KrF exposure, further improvement in the tinting properties of existing materials is necessary. Under these circumstances, the inventors have conducted extensive research and have developed a pigment derivative, i.e., a novel synergist (dispersing agent), thereby enabling the introduction of a coloring agent to which the dispersing agent is applied and a curing system suitable for KrF, ultimately providing a composition capable of implementing ultra-thin, ultra-fine patterning.

[0115] Specifically, the compound represented by the above chemical formula 1 has one or more basic groups at the terminal, and the basic groups are highly polar groups, L a , L 1 Inland L 4 The aforementioned effect can be more effectively realized by introducing the compound represented by the above chemical formula 1 at various positions while being connected to various types of linkers represented by . That is, the dispersion agent represented by the above chemical formula 1 in which the high polar basic group is introduced is used together with a pigment, specifically a yellow pigment, and a dispersant to prevent re-agglomeration of the yellow pigment, thereby minimizing the particle size of the yellow pigment, thereby maximizing dispersion stability.

[0116] In particular, the above L 1 Inland L 4 When at least one of the above is represented by the chemical formula L-1, the number of sites in the compound according to one embodiment into which the basic group can be introduced increases, so that even in a state in which the organic pigment described below is finely dispersed, good fluidity and dispersion stability can be maintained, and it can be easier to provide a pigment dispersion agent that is advantageous for implementing ultra-thin film ultra-fine patterning.

[0117] For example, the basic group is *-NR b Rc (R b and R c Each independently represents a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group), and may be a functional group represented by the following chemical formula B-1 or a functional group represented by the following chemical formula B-2.

[0118] [Chemical Formula B-1]

[0119]

[0120] [Chemical Formula B-2]

[0121]

[0122] In the above chemical formula B-1 and chemical formula B-2,

[0123] R d and R e are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.

[0124] For example, the basic group is *-N + R x R y R z (R x , R y and R z may be represented by a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, respectively.

[0125] For example, the above R a may be a hydrogen atom.

[0126] For example, the above chemical formula 1 can be represented by the following chemical formula 1A or chemical formula 1B.

[0127] [Chemical Formula 1A]

[0128]

[0129] [Chemical Formula 1B]

[0130]

[0131] In the above chemical formulas 1A and 1B,

[0132] X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group),

[0133] L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group, the following chemical formula L-1, or a combination thereof,

[0134] [Chemical formula L-1]

[0135]

[0136] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0137] R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a basic group.

[0138] For example, in the above chemical formulas 1A and 1B, n is an integer of 1 or 2, and L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 If directly connected, n can be an integer of 2.

[0139] For example, in the above chemical formulas 1A and 1B, n is an integer of 1 or 2, and L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 n is an integer of 2 only when directly connected to , otherwise n can be an integer of 1.

[0140] In the above chemical formula 1, *-XL 1 -R 1 By specifying the position of the substituent represented by as in the chemical formula 1A or 1B, the fluidity and dispersion stability of the organic pigment, particularly the yellow organic pigment, can be greatly improved.

[0141] For example, the above R 1 Inland R 4 At least one of them may be a basic group.

[0142] For example, the above R 1 Inland R 4 At least two of them can be basic groups.

[0143] For example, the above R 1 Inland R 4 At least three of them can be basic groups.

[0144] For example, the above R 1 Inland R 4 All of them can be basic groups.

[0145] For example, the above R 1 Inland R 4 At least two or three or more basic groups, or the R 1 Inland R 4 When all are basic groups, the basic groups may be the same or different. In most pigment preparations, it is difficult to combine derivatives with different structures, but the compound according to one embodiment has a structure represented by the chemical formula 1, so it is easy to combine basic groups with different structures, and it has the advantage that the introduction positions of the basic groups can be controlled in various ways.

[0146] For example, the compound may be represented by any one of the following chemical formulas 1-1 to 1-17, but is not necessarily limited thereto.

[0147] [Chemical Formula 1-1]

[0148]

[0149] [Chemical Formula 1-2]

[0150]

[0151] [Chemical Formula 1-3]

[0152]

[0153] [Chemical Formula 1-4]

[0154]

[0155] [Chemical Formula 1-5]

[0156]

[0157] [Chemical Formula 1-6]

[0158]

[0159] [Chemical Formula 1-7]

[0160]

[0161] [Chemical Formula 1-8]

[0162]

[0163] [Chemical Formula 1-9]

[0164]

[0165] [Chemical Formula 1-10]

[0166]

[0167] [Chemical Formula 1-11]

[0168]

[0169] [Chemical Formula 1-12]

[0170]

[0171] [Chemical Formula 1-13]

[0172]

[0173] [Chemical Formula 1-14]

[0174]

[0175] [Chemical Formula 1-15]

[0176]

[0177] [Chemical Formula 1-16]

[0178]

[0179] [Chemical Formula 1-17]

[0180]

[0181] For example, the compound may be a pigment synergist, i.e. a pigment dispersing agent.

[0182] For example, the compound may be a yellow pigment synergist, i.e. a yellow pigment dispersing agent.

[0183] Another embodiment provides a pigment dispersion comprising the pigment synergist and the pigment, which is the compound described above. The compound may be present in an amount of 0.5 to 5 wt% based on the total weight of the pigment dispersion. This minimizes reaggregation of the pigment, thereby maximizing dispersion stability.

[0184] For example, the pigment may be a yellow pigment. Examples of the yellow pigment include Pigment Yellow 138, 139, 150, 185, etc.

[0185] For example, the pigment may be an organic pigment, and the organic pigment may be a finely divided one. The finely divided organic pigment may be a salt-milled organic pigment. Specifically, in order to increase the transmittance and contrast ratio of color filters or inkjet printing, it may be preferable for the organic pigment to be a finely divided one. In addition, it may be more preferable to salt-mill the organic pigment by grinding it with an inorganic salt using a kneader or a mixing device that rotates and revolves three stirring blades respectively, so that the primary particle diameter of the organic pigment becomes even finer. Among these, it may be preferable to use an organic pigment obtained by salt-milling using a mixing device that rotates and revolves three stirring blades respectively. In this case, the salt-milling treatment may be performed so that the primary particle diameter of the pigment becomes even finer and more uniform.

[0186] The pigment may be included in an amount of 5 to 20 wt% based on the total weight of the pigment dispersion. In this case, the interaction between the pigment synergist and the pigment is maximized, thereby minimizing reaggregation of the pigment and maximizing dispersion stability.

[0187] For example, the pigment dispersion may further include a dispersant, a dispersing resin, and a solvent.

[0188] For example, as the dispersant, a polymer pigment dispersant that has been conventionally used in printing ink, paint, pigment dispersion resist composition for color filters, ink for inkjet printing, etc. can be used, and its type can be appropriately selected depending on the type of organic pigment used together or the type of organic solvent described later. Specifically, the dispersant helps the pigment to be uniformly dispersed in the dispersion, and any nonionic, anionic, or cationic dispersant can be used. More specifically, polyalkylene glycol or its ester, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salt, alkyl amide alkylene oxide adduct, alkyl amine, quaternary amine, etc. can be used, and these can be used alone or in combination of two or more.

[0189] The dispersant may be included in an amount of 1 to 5 wt% based on the total amount of the pigment dispersion. If the content of the dispersant is less than 1 wt%, pigment dispersibility may be reduced, and if it exceeds 20 wt%, there may be concerns such as reduced developability.

[0190] For example, the dispersion resin may use an acrylic resin containing a carboxyl group, which can not only improve the stability of the pigment dispersion but also improve the patternability of the pixels.

[0191] The above dispersion resin may be included in an amount of 3 wt% to 10 wt% based on the total amount of the pigment dispersion.

[0192] As the above solvent, ethylene glycol acetate, ethyl cellosolve, propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, etc. can be used, and among these, propylene glycol methyl ether acetate can be preferably used.

[0193] Considering the solubility, pigment dispersibility, and applicability of the dispersion resin, it may be preferable for these solvents to be included as a remainder, for example, 60 wt% to 90 wt%, of the total amount of the pigment dispersion.

[0194]

[0195] Hereinafter, preferred embodiments of the present invention are described. However, the following examples are merely preferred embodiments of the present invention, and the present invention is not limited to the following examples.

[0196]

[0197] (Manufacture of pigment dispersion preparation)

[0198] (Manufacturing Example 1: Synthesis of a compound represented by Chemical Formula 1-1)

[0199] (Reaction Scheme 1)

[0200]

[0201] Compound 1a (11.0 mmol) was added to a solution of compound 1b (10.0 mmol) dissolved in chloroform, and refluxing was performed overnight. After cooling to room temperature, 1 N HCl aqueous solution was added, and the mixture was extracted with dichloromethane. The organic layer was passed through MgSO4, concentrated under reduced pressure, and purified through column chromatography, thereby synthesizing compound 1c.

[0202] (Reaction Formula 2)

[0203]

[0204] Add the compound 1f (10.8 mmol) to the compound 1d (10.5 mmol) and 50 o Stirring was performed for 2 hours at C. Distilled water, 28% ammonia water, and the above compound 1e (10.0 mmol) were added thereto, and stirring was performed until the above compound 1e was completely consumed. Then, acetic acid and the above compound 1c (10.5 mmol) were added, and 85 oThe reaction temperature was raised to C and stirred until the compound 1c was completely consumed. After cooling to room temperature, 28% ammonia water was added to adjust the pH to 7.0–8.0, and the precipitate was separated through reduced pressure filtration. Subsequently, the precipitate was washed several times with methanol and distilled water and dried overnight in a vacuum oven to synthesize the material corresponding to the chemical formula 1-1.

[0205] The analysis results of the above compound are as follows.

[0206] MALDI-TOF MS: 589.25 m / z

[0207]

[0208] (Manufacturing Example 2: Synthesis of a compound represented by Chemical Formula 1-2)

[0209] (Reaction Formula 3)

[0210]

[0211] A substance corresponding to the chemical formula 1-2 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 2a was used instead of the compound 1f.

[0212] The analysis results of the above compound are as follows.

[0213] MALDI-TOF MS: 619.26 m / z

[0214]

[0215] (Manufacturing Example 3: Synthesis of a compound represented by Chemical Formula 1-3)

[0216] (Reaction Scheme 4)

[0217]

[0218] A substance corresponding to the chemical formula 1-3 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 3a was used instead of the compound 1f.

[0219] The analysis results of the above compound are as follows.

[0220] MALDI-TOF MS: 663.19 m / z

[0221]

[0222] (Manufacturing Example 4: Synthesis of a compound represented by Chemical Formula 1-4)

[0223] (Reaction Formula 5)

[0224]

[0225] A substance corresponding to the chemical formula 1-4 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 4a was used instead of the compound 1f.

[0226] The analysis results of the above compound are as follows.

[0227] MALDI-TOF MS: 616.26 m / z

[0228]

[0229] (Manufacturing Example 5: Synthesis of a compound represented by Chemical Formula 1-5)

[0230] (Reaction Scheme 6)

[0231]

[0232] Compound 5b was synthesized in the same manner as the synthesis of compound 1c, except that compound 5a was used instead of compound 1b.

[0233]

[0234] (Reaction Scheme 7)

[0235]

[0236] A substance corresponding to the chemical formula 1-5 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 5b was used instead of the compound 1c.

[0237] The analysis results of the above compound are as follows.

[0238] MALDI-TOF MS: 649.27 m / z

[0239]

[0240] (Manufacturing Example 6: Synthesis of a compound represented by Chemical Formula 1-6)

[0241] (Reaction Formula 8)

[0242]

[0243] A solution of the compound 6a (10.0 mmol) and the compound 6b (15.0 mmol) dissolved in 1,4-dioxane together with triethylamine (30.0 mmol) was added to 90 o C was stirred overnight. After cooling to room temperature, distilled water was added, and this was extracted with ethyl acetate. The organic layer was passed through MgSO4, and purified by column chromatography to obtain the compound 6c. 10 wt% Pd / C was added to the compound 6c dissolved in methanol, and hydrogen was supplied to the reaction mixture using a balloon, and the mixture was stirred overnight. The reaction solution was passed through a celite pad and concentrated under reduced pressure to obtain the compound 6d, which was used in the next reaction without further purification.

[0244]

[0245] (Reaction Formula 9)

[0246]

[0247] A substance corresponding to the chemical formula 1-6 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 6d was used instead of the compound 1f.

[0248] The analysis results of the above compound are as follows.

[0249] MALDI-TOF MS: 754.35 m / z

[0250]

[0251] (Manufacturing Example 7: Synthesis of a compound represented by Chemical Formula 1-7)

[0252] (Reaction Scheme 10)

[0253]

[0254] Compound 7c was synthesized in the same manner as the synthesis of compound 6d, except that compound 7a was used instead of compound 6a.

[0255]

[0256] (Reaction Formula 11)

[0257]

[0258] A substance corresponding to the chemical formula 1-7 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 7c was used instead of the compound 1f.

[0259] The analysis results of the above compound are as follows.

[0260] MALDI-TOF MS: 868.47 m / z

[0261]

[0262] (Manufacturing Example 8: Synthesis of a compound represented by Chemical Formula 1-8)

[0263] (Reaction Formula 12)

[0264]

[0265] Compound 8a (10.0 mmol) was added to a solution of compound 1f (11.0 mmol) and triethylamine (20.0 mmol) dissolved in dichloromethane, and stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, and the reaction mixture was purified through column chromatography to synthesize compound 8b.

[0266]

[0267] (Reaction Formula 13)

[0268]

[0269] Compound 8c was synthesized in the same manner as the synthesis of compound 1c, except that compound 8b was used instead of compound 1b.

[0270]

[0271] (Reaction Formula 14)

[0272]

[0273] A substance corresponding to the chemical formula 1-8 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 8c was used instead of the compound 1c.

[0274] The analysis results of the above compound are as follows.

[0275] MALDI-TOF MS: 626.34 m / z

[0276]

[0277] (Manufacturing Example 9: Synthesis of a compound represented by Chemical Formula 1-9)

[0278] (Reaction Formula 15)

[0279]

[0280] Compound 9b (12.0 mmol) was added to a solution of compound 9a (10.0 mmol) and K2CO3 (15.0 mmol) in acetone, and reflux reaction was performed overnight. After cooling to room temperature, distilled water was added, and extraction was performed with ethyl acetate. The organic layer was passed through MgSO4, the solvent was removed under reduced pressure, and the reaction mixture was purified through column chromatography, thereby synthesizing compound 9c.

[0281]

[0282] (Reaction Formula 16)

[0283]

[0284] Compound 9d was synthesized in the same manner as the synthesis of compound 1c, except that compound 9c was used instead of compound 1b.

[0285]

[0286] (Reaction Formula 17)

[0287]

[0288] A substance corresponding to the chemical formula 1-9 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 9d was used instead of the compound 1c.

[0289] The analysis results of the above compound are as follows.

[0290] MALDI-TOF MS: 642.33 m / z

[0291]

[0292] (Manufacturing Example 10: Synthesis of a compound represented by Chemical Formula 1-10)

[0293] (Reaction Formula 18)

[0294]

[0295] Compound 10b (24.0 mmol) was added to a solution of compound 10a (10.0 mmol) and K2CO3 (30.0 mmol) in acetone, and reflux reaction was performed overnight. After cooling to room temperature, distilled water was added, and extraction was performed with ethyl acetate. The organic layer was passed through MgSO4, the solvent was removed under reduced pressure, and the reaction mixture was purified through column chromatography, thereby synthesizing compound 10c.

[0296]

[0297] (Reaction Formula 19)

[0298]

[0299] Compound 10d was synthesized in the same manner as the synthesis of compound 1c, except that compound 10c was used instead of compound 1b.

[0300]

[0301] (Reaction Formula 20)

[0302]

[0303] A substance corresponding to the chemical formula 1-10 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 10e was used instead of the compound 1f and the compound 10d was used instead of the compound 1c.

[0304] The analysis results of the above compound are as follows.

[0305] MALDI-TOF MS: 832.47 m / z

[0306]

[0307] (Preparation Example 11: Synthesis of a compound represented by Chemical Formula 1-11)

[0308] (Reaction Formula 21)

[0309]

[0310] Compound 11c was synthesized in the same manner as the synthesis of compound 8b, except that compound 11a was used instead of compound 8a and compound 11b was used instead of compound 1f.

[0311]

[0312] (Reaction Formula 22)

[0313]

[0314] Compound 11d was synthesized in the same manner as the synthesis of compound 9c, except that compound 11c was used instead of compound 9a and compound 10b was used instead of compound 9b.

[0315]

[0316] (Reaction Formula 23)

[0317]

[0318] Compound 11e was synthesized in the same manner as the synthesis of compound 1c, except that compound 11d was used instead of compound 1b.

[0319]

[0320] (Reaction Formula 24)

[0321]

[0322] A substance corresponding to the chemical formula 1-11 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 10e was used instead of the compound 1f and the compound 11e was used instead of the compound 1c.

[0323] The analysis results of the above compound are as follows.

[0324] MALDI-TOF MS: 740.44 m / z

[0325]

[0326] (Manufacturing Example 12: Synthesis of a compound represented by Chemical Formula 1-12)

[0327] (Reaction Formula 25)

[0328]

[0329] Compound 12c was synthesized in the same manner as the synthesis of compound 8b, except that compound 12a was used instead of compound 8a and compound 12b was used instead of compound 1f.

[0330]

[0331] (Reaction Formula 26)

[0332]

[0333] Compound 12d was synthesized in the same manner as the synthesis of compound 1c, except that compound 12c was used instead of compound 1b.

[0334]

[0335] (Reaction Formula 27)

[0336]

[0337] A substance corresponding to the chemical formula 1-12 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 12d was used instead of the compound 1c.

[0338] The analysis results of the above compound are as follows.

[0339] MALDI-TOF MS: 670.36 m / z

[0340]

[0341] (Preparation Example 13: Synthesis of a compound represented by Chemical Formula 1-13)

[0342] (Reaction Formula 28)

[0343]

[0344] Compound 13b was synthesized in the same manner as the synthesis of compound 8b, except that compound 13a was used instead of compound 8a.

[0345]

[0346] (Reaction Formula 29)

[0347]

[0348] Compound 13c was synthesized in the same manner as the synthesis of compound 9c, except that compound 13b was used instead of compound 9a.

[0349]

[0350] (Reaction Formula 30)

[0351]

[0352] Compound 13d was synthesized in the same manner as the synthesis of compound 1c, except that compound 13c was used instead of compound 1b.

[0353]

[0354] (Reaction Formula 31)

[0355]

[0356] A substance corresponding to the chemical formula 1-13 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 13d was used instead of the compound 1c.

[0357] The analysis results of the above compound are as follows.

[0358] MALDI-TOF MS: 755.45 m / z

[0359]

[0360] (Preparation Example 14: Synthesis of a compound represented by Chemical Formula 1-14)

[0361] (Reaction Formula 32)

[0362]

[0363] Compound 14b was synthesized in the same manner as the synthesis of compound 10c, except that compound 14a was used instead of compound 10b.

[0364] (Reaction Formula 33)

[0365]

[0366] Compound 14c was synthesized in the same manner as the synthesis of compound 1c, except that compound 14b was used instead of compound 1b.

[0367]

[0368] (Reaction Formula 34)

[0369]

[0370] A substance corresponding to the chemical formula 1-14 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 14c was used instead of the compound 1c.

[0371] The analysis results of the above compound are as follows.

[0372] MALDI-TOF MS: 847.48 m / z

[0373]

[0374] (Manufacturing Example 15: Synthesis of a compound represented by Chemical Formula 1-15)

[0375] (Reaction Formula 35)

[0376]

[0377] Compound 15a (10.0 mmol) and compound 1f (15.0 mmol) were added to dimethyl sulfoxide together with K2CO3 (20.0 mmol) and stirred overnight at room temperature. After the reaction, an excess of distilled water was added, and the mixture was extracted with chloroform. The organic layer was passed through MgSO4 and concentrated under reduced pressure to obtain compound 15b, which was used in the next reaction without further purification. Sodium hydroxide (0.230 mmol) was added to a solution of compound 15b (7.80 mmol) in methanol, and ammonia was supplied into the solution using a balloon. Reflux stirring was performed for 3 hours under continuous ammonia supply, and the resulting precipitate was filtered under reduced pressure and washed with cooled methanol. The solid was dried in a vacuum oven to obtain compound 15c.

[0378] (Reaction Formula 36)

[0379]

[0380] A substance corresponding to the chemical formula 1-15 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 15c was used instead of the compound 1e and the compound 10d was used instead of the compound 1c.

[0381] The analysis results of the above compound are as follows.

[0382] MALDI-TOF MS: 931.57 m / z

[0383]

[0384] (Manufacturing Example 16: Synthesis of a compound represented by Chemical Formula 1-16)

[0385] (Reaction Formula 37)

[0386]

[0387] Compound 16a (10.0 mmol) and NaH (60% in mineral oil) (30.0 mmol) were suspended in N,N-dimethylformamide and stirred at room temperature for 30 minutes. Compound 10b (15.0 mmol) was added and stirred overnight at room temperature. Excess water was added and extracted with ethyl acetate. The organic layer was passed through MgSO4 and concentrated under reduced pressure, and purified through column chromatography to synthesize compound 16b.

[0388] (Reaction Formula 38)

[0389]

[0390] Compound 16c was synthesized in the same manner as the synthesis of compound 8b, except that compound 11a was used instead of compound 8a and compound 16b was used instead of compound 1f.

[0391]

[0392] (Reaction Formula 39)

[0393]

[0394] Compound 16e was synthesized in the same manner as the synthesis of compound 9c, except that compound 16a was used instead of compound 9a, and compound 16d was used instead of compound 9b.

[0395]

[0396] (Reaction Formula 40)

[0397]

[0398] Compound 16f was synthesized in the same manner as the synthesis of compound 1c, except that compound 16e was used instead of compound 1b.

[0399]

[0400] (Reaction Formula 41)

[0401]

[0402] A substance corresponding to Chemical Formula 1-16 was synthesized in the same manner as the synthesis of the substance corresponding to Chemical Formula 1-1, except that the compound 15c was used instead of the compound 1e, the compound 10e was used instead of the compound 1f, and the compound 16f was used instead of the compound 1c.

[0403] The analysis results of the above compound are as follows.

[0404] MALDI-TOF MS: 1006.51 m / z

[0405]

[0406] (Preparation Example 17: Synthesis of a compound represented by Chemical Formula 1-17)

[0407] (Reaction Formula 42)

[0408]

[0409] Compound 17c was synthesized in the same manner as the synthesis of compound 15c, except that compound 17a was used instead of compound 1f.

[0410]

[0411] (Reaction Formula 43)

[0412]

[0413] A substance corresponding to the chemical formula 1-17 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 17c was used instead of the compound 1e and the compound 14b was used instead of the compound 1c.

[0414] The analysis results of the above compound are as follows.

[0415] MALDI-TOF MS: 976.59 m / z

[0416]

[0417] (Comparative Manufacturing Example 1: Synthesis of a compound represented by Chemical Formula C-1)

[0418] (Reaction Formula 44)

[0419]

[0420] A substance corresponding to the chemical formula C-1 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 18a was used instead of the compound 1f and the compound 18b was used instead of the compound 1c.

[0421] The analysis results of the above compound are as follows.

[0422] MALDI-TOF MS: 380.13 m / z

[0423]

[0424] (Comparative Manufacturing Example 2: Synthesis of a compound represented by Chemical Formula C-2)

[0425] (Reaction Formula 45)

[0426]

[0427] A substance corresponding to the chemical formula C-2 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 10e was used instead of the compound 1f.

[0428] The analysis results of the above compound are as follows.

[0429] MALDI-TOF MS: 490.14 m / z

[0430]

[0431] (Comparative Manufacturing Example 3: Synthesis of a compound represented by chemical formula C-3)

[0432] (Reaction Formula 46)

[0433]

[0434] A substance corresponding to the chemical formula C-3 was synthesized in the same manner as the synthesis of the substance corresponding to the chemical formula 1-1, except that the compound 19a was used instead of the compound 1e, the compound 10e was used instead of the compound 1f, and the compound 18b was used instead of the compound 1c.

[0435] The analysis results of the above compound are as follows.

[0436] MALDI-TOF MS: 368.09 m / z

[0437]

[0438] (Manufacture of pigment dispersion)

[0439] (Example 1)

[0440] A pigment dispersion was prepared by mixing 0.5 wt% of the pigment dispersion agent of Manufacturing Example 1, 9.5 wt% of yellow pigment (Y185), 5 wt% of dispersant, 4.5 wt% of dispersion resin, and 80.5 wt% of solvent.

[0441] (Example 2)

[0442] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 2 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0443] (Example 3)

[0444] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 3 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0445] (Example 4)

[0446] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 4 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0447] (Example 5)

[0448] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 5 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0449] (Example 6)

[0450] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 6 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0451] (Example 7)

[0452] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 7 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0453] (Example 8)

[0454] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 8 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0455] (Example 9)

[0456] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 9 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0457] (Example 10)

[0458] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 10 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0459] (Example 11)

[0460] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 11 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0461] (Example 12)

[0462] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 12 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0463] (Example 13)

[0464] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 13 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0465] (Example 14)

[0466] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 14 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0467] (Example 15)

[0468] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 15 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0469] (Example 16)

[0470] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 16 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0471] (Example 17)

[0472] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Manufacturing Example 17 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0473] (Comparative Example 1)

[0474] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Comparative Manufacturing Example 1 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0475] (Comparative Example 2)

[0476] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Comparative Manufacturing Example 2 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0477] (Comparative Example 3)

[0478] The same procedure as Example 1 was followed, except that the pigment dispersion preparation of Comparative Manufacturing Example 3 was used instead of the pigment dispersion preparation of Manufacturing Example 1.

[0479]

[0480] (Manufacture of photosensitive resin composition)

[0481] (Example 1-1)

[0482] A photosensitive resin composition was prepared by mixing 2 wt% of binder resin (RY92-M10, Showa Denko Co., Ltd.), 2 wt% of polymerizable monomer (DPHA, Nippon Gunyaku Co., Ltd.), 2.5 wt% of polymerization initiator (SPI-03, Samyang Co., Ltd.), 37 wt% of green pigment (G58, Sanyo Co., Ltd.) dispersion, 29 wt% of the pigment dispersion of Example 1, 0.02 wt% of silane coupling agent (KBM-503, ShinEtsu Co., Ltd.), and 27.48 wt% of solvent (PGMEA, DAICEL Co., Ltd.).

[0483] (Example 2-1)

[0484] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 2 was used instead of the pigment dispersion of Example 1.

[0485] (Example 3-1)

[0486] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 3 was used instead of the pigment dispersion of Example 1.

[0487] (Example 4-1)

[0488] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 4 was used instead of the pigment dispersion of Example 1.

[0489] (Example 5-1)

[0490] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 5 was used instead of the pigment dispersion of Example 1.

[0491] (Example 6-1)

[0492] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 6 was used instead of the pigment dispersion of Example 1.

[0493] (Example 7-1)

[0494] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 7 was used instead of the pigment dispersion of Example 1.

[0495] (Example 8-1)

[0496] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 8 was used instead of the pigment dispersion of Example 1.

[0497] (Example 9-1)

[0498] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 9 was used instead of the pigment dispersion of Example 1.

[0499] (Example 10-1)

[0500] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 10 was used instead of the pigment dispersion of Example 1.

[0501] (Example 11-1)

[0502] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 11 was used instead of the pigment dispersion of Example 1.

[0503] (Example 12-1)

[0504] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 12 was used instead of the pigment dispersion of Example 1.

[0505] (Example 13-1)

[0506] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 13 was used instead of the pigment dispersion of Example 1.

[0507] (Example 14-1)

[0508] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 14 was used instead of the pigment dispersion of Example 1.

[0509] (Example 15-1)

[0510] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 15 was used instead of the pigment dispersion of Example 1.

[0511] (Example 16-1)

[0512] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 16 was used instead of the pigment dispersion of Example 1.

[0513] (Example 17-1)

[0514] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Example 17 was used instead of the pigment dispersion of Example 1.

[0515] (Comparative Example 1-1)

[0516] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Comparative Example 1 was used instead of the pigment dispersion of Example 1.

[0517] (Comparative Example 2-1)

[0518] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Comparative Example 2 was used instead of the pigment dispersion of Example 1.

[0519] (Comparative Example 3-1)

[0520] The same procedure as Example 1-1 was followed, except that the pigment dispersion of Comparative Example 3 was used instead of the pigment dispersion of Example 1.

[0521]

[0522] (evaluation)

[0523] particle size assessment

[0524] The particle diameters of the solids contained in each of the photosensitive resin compositions of Examples 1-1 to 17-1 and Comparative Examples 1-1 to 3-1 were measured using a dynamic light scattering analyzer (ELS-Z, Otsuka), and the results for the average particle diameter are shown in Tables 1 and 2 below.

[0525]

[0526] Example 1-12-13-14-15-16-17-18-19-110-111-1 Particle size (nm) 119117120120119118117117118117118

[0527] Comparative Example 12-113-114-115-116-117-11-12-13-1 Particle Size (nm) 120 118 118 117 116 115 129 124 130

[0528] From the above Tables 1 and 2, it can be confirmed that the compound according to one embodiment can significantly improve dispersion stability by preventing aggregation between pigments used together as a pigment synergist.

[0529]

[0530] Spectral characteristic evaluation

[0531] The photosensitive resin compositions of Examples 1-1 to 17-1 and Comparative Examples 1-1 to 3-1 were spin-coated on glass specimens (10 X 10 cm) in 3 layers each with a thickness of 0.3 to 0.5 ㎛, and then pre-baked on a 100 ℃ hot plate for 3 minutes. Subsequently, a UV exposure device was used to expose the glass specimens at 200 mJ / cm. 2 After exposure to light, it was post-baked on a 230 ℃ hot plate for 5 minutes. The spectrum of the manufactured three sheets of specimen was measured using a chromaticity meter (MPCD-1, Otsuka), and the thickness was measured using a contact thickness measuring device (Tencor P-16). The measured results were calculated to obtain the transmittance values ​​(%) corresponding to each wavelength at a thickness of 0.35 ㎛, which are shown in Tables 3 and 4 below. The better the tinting power of the yellow color filter composition, the lower the transmittance value at a wavelength of 450 nm based on the same thickness.

[0532]

[0533] Example 1-12-13-14-15-16-17-18-19-110-111-1 Transmittance (450 nm) 1313141413131213131313

[0534] Example Comparative Example 12-113-114-115-116-117-11-12-13-1 Transmittance (450 nm) 141414141211151516

[0535] From the above Tables 3 and 4, it can be confirmed that the compound according to one embodiment can secure excellent spectral characteristics as a pigment synergist without reducing the tinting power of the composition.

[0536]

[0537] The present invention is not limited to the above-described embodiments, but can be manufactured in a variety of different forms. Those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group, the following chemical formula L-1, or a combination thereof, [Chemical formula L-1] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a basic group, provided that R 1 Inland R 4 At least one of them is a basic group, n is an integer of 1 or 2, and the above L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 If directly connected, n is an integer of 2.

2. In paragraph 1, The above basic group is *-NR b R c (R b and R c wherein each independently represents a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group), a compound having the following chemical formula B-1 or the following chemical formula B-2: [Chemical Formula B-1] [Chemical Formula B-2] In the above chemical formula B-1 and chemical formula B-2, R d and R e are each independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.

3. In paragraph 1, The above R a is a compound containing hydrogen atoms.

4. In paragraph 1, The above chemical formula 1 is a compound represented by the following chemical formula 1A or chemical formula 1B: [Chemical Formula 1A] [Chemical Formula 1B] In the above chemical formulas 1A and 1B, X is a single bond, ether group (*-O-*) or *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), L 1 Inland L 4 are each independently a single bond, a substituted or unsubstituted C1 to C20 alkylene group, an ether group (*-O-*), *-N(R a )-*(R a is a hydrogen atom or a substituted or unsubstituted C1 to C10 alkyl group), a substituted or unsubstituted C1 to C20 alkoxy group, the following chemical formula L-1, or a combination thereof, [Chemical formula L-1] L a is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 1 Inland R 4 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a basic group, n is an integer of 1 or 2, and the above L 2 is represented by the chemical formula L-1 and the linking group represented by the chemical formula L-1 is R 2 If directly connected, n is an integer of 2.

5. In paragraph 1, The above R 1 Inland R 4 A compound in which at least two of the groups are basic groups.

6. In paragraph 1, The above R 1 Inland R 4 A compound in which at least three or more of the groups are basic.

7. In paragraph 6, The above basic groups are compounds of the same type.

8. In paragraph 1, The above basic groups are compounds of different types.

9. In paragraph 1, The above compound is a compound represented by any one of the following chemical formulas 1-1 to 1-17. [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] 10. In paragraph 1, The above compound is a pigment synergist.

11. In paragraph 10, The above compound is a compound that is a yellow pigment synergist.

12. A pigment dispersion comprising a compound and a pigment according to any one of claims 1 to 11.

13. In paragraph 12, The above pigment is a pigment dispersion which is a yellow pigment.

14. In paragraph 12, The above pigment dispersion further comprises a dispersant, a dispersing resin, and a solvent.

15. In paragraph 14, The above pigment dispersion is based on the total amount of the above pigment dispersion. 0.5 wt% to 5 wt% of the above compound; 5 to 20 wt% of the pigment; 1 to 5 wt% of the above dispersant; 3 to 10 wt% of the above dispersion resin; and The above solvent residue A pigment dispersion containing .

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