TWI557118B - Three acridine Compounds, pigment dispersing aids, pigment dispersions and photoresist compositions - Google Patents

Description

Triterpenoids, pigment dispersing aids, pigment dispersions and photoresist compositions

The present invention relates to three A compound, a pigment dispersing aid, a pigment dispersion, and a photoresist composition. More specifically, the present invention relates to a novel triterpenoid used as a dispersing aid for pigments. Compounds and their uses.

The color filter of one of the constituent members of the color liquid crystal display is formed on the surface of the glass substrate to form a black matrix and each of the three primary colors of RGB (red, green, and blue) for coloring the image displayed on the color liquid crystal display. . The RGB color pattern is formed by a photolithography method using a photoresist composition containing a pigment, a photosensitive resin, a photopolymerizable monomer, a photopolymerization initiator, a solvent, or the like.

Since the pigment used in the photoresist composition has strong cohesiveness, it is difficult to maintain a uniform dispersion state of the pigment in a medium such as a solution of water, a solvent or a resin. Therefore, the photoresist composition does not have sufficient storage stability from the viewpoint of maintaining the dispersibility of the pigment. Moreover, when the pigment is agglomerated, the viscosity of the photoresist composition rises, and not only the coating property of the photoresist composition on the glass substrate is lowered, but also by the photoresist group. The performance of the color filters of the various patterns formed by the objects is also reduced.

Moreover, in order to save power of a color liquid crystal display, a color filter of higher luminance is required. In general, when the film thickness of the color filter is thinner, the luminance tends to be higher. At this time, in order to ensure high color reproducibility, it is necessary to achieve a high pigment concentration. However, since the concentration of the pigment is increased, the storage stability or coating property of the photoresist composition is further lowered, so that it is difficult to produce a color filter having sufficient performance.

On the other hand, when the pigment is dispersed in a medium, a pigment dispersant and a dispersing aid are generally used. The dispersing aid is intermediate between the pigment and the pigment dispersing agent, and has the function of assisting the pigment dispersion. As the dispersing aid, a good pigment adsorption efficiency with respect to the surface of the pigment is mostly a pigment derivative having the same parent skeleton as the pigment. Although the pigment derivative and the pigment have the same parent skeleton, the structure as a whole molecule is different from the pigment, and thus exhibits a color different from that of the pigment. Therefore, when a pigment dispersion containing a pigment derivative is used as a dispersing aid, the transmission spectrum of the color filter becomes wider than that of a color filter using only a pigment, and The difference is that the brightness of the portrait of the color liquid crystal display is lowered.

In the past, the proposal has three The ring is a pigment dispersant or a dispersing aid of the parent skeleton (refer to Patent Document 1 and Patent Document 2). Patent Document 1 describes, for example, a pigment dispersant represented by the following formula (I). Further, in Patent Document 2, for example, a dispersing aid represented by the following formula (II) is taught. However, there is still room for further improvement of these compounds from the viewpoint of improving the dispersibility of the pigments in various media and suppressing the decrease in the brightness of the image represented by the color liquid crystal display.

[Previous Technical Literature] [Patent Document]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2008-214515

[Patent Document 2] Japanese Patent Laid-Open Publication No. 2011-032374

It is an object of the present invention to provide a triterpenoid suitable as a dispersing aid for pigments. a compound comprising the three A pigment dispersing aid of a compound, a pigment dispersion containing the pigment dispersing aid, and a photoresist composition comprising the pigment dispersion and capable of forming a color filter capable of high-luminance color development.

In order to solve the above problems, the inventors of the present invention have found out that by using a pigment dispersing aid which is almost unrecognized in the visible field (400 to 700 nm) and which exhibits white color, it is possible to suppress the pigment dispersing aid. The brightness caused by the influence of the penetration spectrum is reduced. Based on such findings, the team of the present invention has succeeded in obtaining the desired characteristics and is suitable as a pigment dispersing aid. The present invention has been completed by the compound.

That is, the present invention provides a three-way diagram represented by the following general formula (1) Compound (hereinafter referred to as "three 吖 Compound"), [In the formula (1), R ^{1 is} shown as a base: ,base: Or base: R ^{2 is} shown as: ,base: ,base: a hydroxyl group or a halogen atom; R ³ , R ⁴ and R ⁵ may be the same or differently represented as a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, or R ³ and R ⁴ , or R ⁴ and R ⁵ are bonded to each other to form a benzene ring; R ⁶ is represented by a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and R ⁷ is represented by a hydrogen atom or carbon Number 1~4 alkoxy; 1 is three The average number of introduced sulfonic acid groups in one molecule of the compound (1) is shown as a number from 1 to 2; m and n are each shown as an integer from 1 to 2).

In the above general formula (1), the sulfonic acid group (-SO ₃ H) and the group represented by the symbol R ⁶ may be respectively substituted by a benzene ring directly bonded to a nitrogen atom, and may be further subjected to R ³ and R ^{4 .} Or R ⁴ and R ⁵ are substituted by a benzene ring formed by mutual bonding, and may be substituted by a benzene ring of both.

The above three Among the compounds (1), preferred are three oximes represented by the following general formula (2). Compound (hereinafter referred to as "three 吖 Compound (2)"), [In the formula (2), R ³ , R ⁴ and R ⁵ may be the same or differently represented as a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, or R ³ and R ⁴ , or R ⁴ and R ⁵ are bonded to each other to form a benzene ring; R ¹⁰ and R ¹¹ may be the same or differently shown as a group: ,base: Or base: R ⁷ is represented by a hydrogen atom or an alkoxy group having a carbon number of 1 to 4; The average number of introduced sulfonic acid groups in one molecule of the compound (2) is shown as a number from 1 to 2; n is an integer from 1 to 2.

The above three More preferably, in the compound (2), R ¹⁰ and R ¹¹ may be the same or different as R ⁷ is represented by a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms; n is a compound represented by an integer of 1 to 2.

More, the above three Further, in the compound (2), a compound in which R ¹⁰ and R ¹¹ are the same group is more preferable.

In the above general formula (2), the sulfonic acid group (-SO ₃ H) may be substituted by a benzene ring directly bonded to a nitrogen atom, and may be a mutual bond via R ³ and R ⁴ or R ⁴ and R ^{5 .} The benzene ring formed by the formation is replaced by a benzene ring of both sides.

Again, the above three Among the compounds (1), preferred are three oximes represented by the following general formula (3). Compound (hereinafter referred to as "three 吖 Compound (3)"),

[In the formula (3), R ³ , R ⁴ and R ⁵ may be the same or differently represented as a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, or R ³ and R ⁴ , or R ⁴ and R ⁵ are bonded to each other to form a benzene ring; R ⁶ is represented by a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; The average number of introduced sulfonic acid groups in one molecule of the compound (3) is shown as a number from 1 to 2; m is an integer from 1 to 2; and X is a hydroxyl group, a halogen atom or a group: R ^{10 is} shown as: ,base: Or base: R ⁷ is represented by a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms; n is an integer of 1 to 2].

The above three In the compound (3), R ¹⁰ is preferably a group of the following groups. Compound,

In the above general formula (3), the sulfonic acid group (-SO ₃ H) and the group represented by the symbol R ⁶ may be respectively substituted by a benzene ring directly bonded to a nitrogen atom, and may be further subjected to R ³ and R ^{4 .} Or R ⁴ and R ⁵ are substituted by a benzene ring formed by mutual bonding, and may be substituted by a benzene ring of both.

Moreover, the present invention provides for the inclusion of the above three A pigment dispersing aid of the compound (1).

Further, the present invention provides a pigment dispersion comprising a pigment, a pigment dispersant, the above pigment dispersing aid, and a solvent. In the pigment dispersion, the volume average particle diameter of the pigment is preferably from 10 to 100 nm. Further, in the pigment dispersion, the content of the pigment is 30 to 80% by weight based on the total solid content of the pigment dispersion, and preferably 10 to 60 parts by weight based on 100 parts by weight of the pigment. The pigment dispersing aid is contained in an amount of 1 to 25 parts by weight.

Furthermore, the present invention provides a photoresist composition comprising the above pigment dispersion and a photosensitive compound.

By the present invention, it is possible to provide a triterpenoid which can be suitably used as a dispersing aid for pigments. Compound (1). By using the inclusion of the three The pigment dispersing aid of the compound (1) can provide a pigment dispersion in which the pigment is uniformly dispersed in various media. Also, including the use of the three The photoresist composition of the pigment dispersion obtained by the compound (1) can be suitably used to produce a color filter capable of high-luminance color development. The color filter produced by using the photoresist composition of the present invention can emit high luminance for the three primary colors of RGB (red, green, and blue), especially in the case of green color, the luminance is remarkably high, so should.

[Best Practice for Carrying Out the Invention] [三吖 Compound (1)]

Three 吖 of the present invention The compound (1) is suitable as a dispersing aid for pigments. That is, the three 本 of the present invention Compound (1) interacts with the pigment dispersant to uniformly disperse the pigment in various media. Therefore, the three 包含 containing the present invention The pigment dispersion and the photoresist composition of the compound (1) have excellent storage stability because the re-agglomeration of the pigment and the increase in viscosity can be suppressed. Still, the three 本 of the present invention Among the pigment dispersants, the compound (1) has an effect of improving the dispersibility of the pigment and an effect of suppressing the re-agglomeration of the pigment, particularly when used in combination with the resin-type dispersant.

Moreover, due to the three 本 of the present invention Compound (1) is white in the visual field, so by including the three 本 of the present invention A color filter formed of the photoresist composition of the compound (1) can produce a color liquid crystal display capable of high-luminance color development.

In the above general formulas (1) to (3), examples of the alkyl group having 1 to 4 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, sec-propyl group, n-butyl group and the like. A linear or branched chain of 1 to 4 carbon atoms such as butyl, sec-butyl or tert-butyl. Examples of the alkoxy group having 1 to 4 carbon atoms include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, a sec-propoxy group, an n-butoxy group, and an isobutoxy group. A linear or branched chain alkoxy group having 1 to 4 carbon atoms such as sec-butoxy group or tert-butoxy group. Examples of the halogen atom include chlorine, bromine, iodine, fluorine, and the like.

Three 吖 of the present invention Among the compounds (1), more preferably three Compound (2) and triterpenoid Compound (3).

Sancha In the compound (2), the initial dispersion of the pigment dispersion using the pigment is relatively low, and since the effect of suppressing the re-agglomeration of the pigment is high, it contains three oximes. The pigment dispersion of the compound (2) is excellent in storage stability, and the viscosity increase due to storage is relatively small. Also, use three 吖 The color filter composition of the compound (2) is used to form a color filter, and the high luminance of the image represented by the color liquid crystal display can be achieved. Sancha Among the compounds (2), when considering the initial viscosity of the pigment dispersion and the viscosity increase ratio of the pigment dispersion during storage, it is more preferable that R ¹⁰ and R ¹¹ may be the same or different. [wherein, R ⁷ and n are synonymous with the above] a compound; more preferably, R ¹⁰ and R ¹¹ are the same three Compound. Shang, Sancha In the compound (2), it is particularly preferred that all of R ³ , R ⁴ and R ⁵ are a hydrogen atom. As such a three-way Specific examples of the compound (2) include three oximes as shown in Table 1 below. Compound (2a) to (2c).

Sancha Compound (3), when the pigment dispersion using the same, is used in the initial viscosity or pigment dispersion, although it will be more The compound (2) is slightly higher, but it is within a practical range, and further contributes to high luminance of the image represented by the color liquid crystal display. Sancha Among the compounds (3), when the initial viscosity of the pigment dispersion and the viscosity at the time of storage of the pigment dispersion or the high luminance of the image are considered, R ¹⁰ is preferably Compound.

Shang, Sancha In the compound (3), it is preferred that all of R ³ , R ⁴ and R ⁵ are a hydrogen atom. As such a three-way Specific examples of the compound (3) include three oximes as shown in Table 2 below. Compound (3a) to (3d).

Three 吖 of the present invention The compound (1) can be obtained by a reaction obtained by reacting cyanuric chloride with a sulfonate compound (10) represented by the following general formula (10), and then reacting the obtained reactant with the following At least one of the compounds (11) to (13) represented by the general formulae (11) to (13) is reacted.

[In the formula (10), R ³ to R ⁶ , l and m are synonymous with the above].

Specific examples of the sulfonoxy compound (10) include, for example, o-amine benzenesulfonic acid (2-aminobenzenesulfonic acid), sulfamic acid, p-toluidine-2-sulfonic acid, m-aminobenzenesulfonic acid, and p-methyl. Oxyaniline-2-sulfonic acid, aniline-2,4-disulfonic acid, 2,4-dimethylanilin-6-sulfonic acid and the like. The amount of the sulfonate (10) used in comparison with the cyanuric chloride monomole is usually 0.5 to 15 moles, preferably 0.9 to 11 moles.

The reaction of the cyanuric chloride and the sulfonate (10) can be carried out, for example, in a suitable solvent with stirring or without stirring at a temperature of about 5 to 30 ° C for 1 to 2 hours. As the solvent, for example, water, an organic solvent such as acetone, dioxane, xylene or dimethylformamide, or a mixed solvent of two or more kinds thereof may be used.

The reactant obtained in the above manner is reacted with at least one of the compounds (11) to (13) represented by the following general formulas (11) to (13).

[In the formulae (11) to (13), R ⁷ and n are synonymous with the above].

As a specific example of the compound (11), 5-amino-2-benzimidazolinone (5-amino-2-benzimidazolinone) is exemplified. Specific examples of the compound (12) include, for example, 4-aminobenzamide, 3-amino-4-methoxybenzamide, and the like. The amount of the compound (11) to (13) to be used is appropriately selected depending on the kind of the compound to be used, but it is usually 0.5 to 2.5, relative to the reactant 1 mole of the cyanuric chloride and the sulfonate (10). Moor, preferably 0.9 to 2.2 moles. In the reaction between the reactants and the compounds (11) to (13), an organic acid such as acetic acid, benzoic acid, citric acid, fumaric acid, gluconic acid or oxalic acid or a mineral acid such as hydrochloric acid, sulfuric acid or nitric acid may be used as the inorganic acid. Solvent use. These acids are preferably used in the form of an aqueous solution.

The reaction of the above reactants with the compounds (11) to (13) can be carried out at a temperature of about 50 to 100 ° C in a suitable solvent with or without stirring, and the reaction is completed in about 1 to 5 hours. As the solvent, the same solvent used in the reaction of cyanuric chloride and the sulfonate (10) can be used. Use this to generate three Compound (1). Will get the three The compound (1) can be easily purified from the reaction mixture by a usual separation and purification means such as filtration, water washing, and drying.

[Pigment Dispersing Aid]

The pigment dispersing aid of the present invention comprises a selected from the group consisting of One type or two or more types of the compound (1), for example, in the coexistence with a pigment or in the presence of a pigment or a pigment dispersant, the effect of the pigment on the dispersibility of the solvent can be improved, or in the dispersion of the material. Since the dispersibility or storage stability of the pigment is improved, it is considered that the effect of suppressing the increase in the viscosity of the pigment dispersion due to re-agglomeration of the pigment during storage or the like is considered.

The pigment to be used as the pigment dispersing aid of the present invention is not particularly limited, but is preferably an organic pigment. Specific examples of the organic pigment include an anthraquinone pigment, a perinone pigment, a quinophthalone pigment, a quinophthalone pigment, an anthraquinone pigment, an anthothrone pigment, and benzene. Imidazolidone-based pigment, disazo-based pigment, azo-based pigment, indanthrone pigment, phthalocyanine pigment, triarylcarbon ion pigment, dioxazine pigment, amine lanthanide Pigment, pyrrolopyrroledione pigment, indigo pigment, thioindigo pigment, isoindolinone pigment, isoporphyrin pigment, dermophenone pigment, isopurinone pigment, metal mismatch Pigment, quinoline yellow pigment, and the like. Among these, an anthraquinone pigment, a purple ring ketone pigment, a quinophthalone pigment, an anthraquinone pigment, an azo pigment, a phthalocyanine pigment, a dioxazine pigment, and a pyrrolopyrroledione are preferable. A pigment, an indigo pigment, an isoindolinone pigment, an isoporphyrin pigment, a metal complex pigment, a quinoline yellow pigment, or the like.

In addition, the pigment dispersing aid which can be used together with the pigment dispersing aid of the present invention is not particularly limited, and examples thereof include a resin type dispersing agent and a surfactant type dispersing agent. Among these, a resin-type dispersing agent is preferable from the viewpoint of sufficiently exhibiting the effect of pigment dispersion or the effect of suppressing re-agglomeration of the pigment by the pigment dispersing aid of the present invention.

The resin type dispersant is not particularly limited, and examples thereof include polyurethanes, polyesters, unsaturated polyamines, phosphates, polycarboxylic acids and amine salts thereof, ammonium salts, alkylamine salts, and polycarboxylates. An oily resin type dispersant such as a hydroxyl group-containing polycarboxylate, a polyoxyalkylene or a modified polyacrylate, alginic acid, polyvinyl alcohol, hydroxypropyl cellulose, carboxymethyl cellulose, hydroxyethyl fiber Water-soluble polymer compound such as cellulose, methyl cellulose, polyvinylpyrrolidone, gum arabic, etc.; styrene-acrylic resin, styrene-methacrylic resin, styrene-acrylic acid-acrylate resin, styrene-ma Esters, styrene-maleate resins, methacrylic acid-methacrylate resins, acrylic acid-acrylate resins, isobutylene-maleic acid resins, vinyl-ester resins, rosin-modified maleic resins, etc. A resin containing an ethylenic double bond; an amine resin such as polyallylamine, polyvinylamine or polyethyleneimine; or an aqueous resin type dispersant.

Various resin-based dispersants are commercially available, and specific examples of the commercially available products include "Solsperse" 3000, 9000, 13240, 17000, 20000, 24000, 26000, 28000, 32000, 32500, and 41000 (all of which are commodities). Name, Japan Lubrizol Co., Ltd., "Disperbyk-" 108, 110, 112, 140, 142, 145, 161, 162, 163, 164, 166, 167, 182, 2000, 2001, 2050, 2070, 2150, "BYK LPN-" 6919, 21116 (all are trade names, BYK-Chemie Japan Co., Ltd.), "EFKA-" 4401, 4403, 4406, 4010, 4015, 4046, 4047, 4050, 4055, 4060, 4080, 5064, 5207, 5244 (all are trade names, manufactured by EFKA Additive), "Ajisper" PB821 (F), PB822, PB880 (all are trade names, Ajinomoto Fine-Techno), Hinoact T -8000 (trade name, manufactured by Kawasaki Fine Chemicals Co., Ltd.), Disparon PW-36, "Disparon DA-" 325, 375, and 7301 (all of which are trade names, manufactured by Nanmu Chemicals Co., Ltd.).

Among the resin-type dispersants, those having a weight average molecular weight of about 1,000 to 30,000 are preferable.

The surfactant-type dispersing agent is not particularly limited, and examples thereof include an anionic active agent such as a naphthalenesulfonic acid formalin condensate salt, an aromatic sulfonic acid formalin condensate, a polyoxyethylene alkyl phosphate, and the like, and a polyoxyethylene alkyl ether. A cationic active agent such as a nonionic active agent, an alkylamine salt or a fourth-order ammonium salt. Various surfactant-type dispersing agents are also commercially available. Examples of such specific examples include "Demol" N, RN, MS, SN-B, "Emulgen" 120, 430, "Acetamin" 24, 86, Quartamin 24P ( All are trade names, Kao (shares), "Plysurf" AL, A208F (both are trade names, the first industrial system (shares)), "Arquad" C-50, T-28, T-50 (all For the trade name, Lion (share) system, etc.

The pigment dispersing agent may be used alone or in combination of two or more.

The amount of the pigment dispersing aid used is not particularly limited, as opposed to The pigment is 100 parts by weight, preferably 1 to 25 parts by weight, more preferably 3 to 20 parts by weight. When the content of the pigment dispersing aid is less than 1 part by weight, the effect of the pigment dispersing aid may not be sufficiently exhibited. When the content of the pigment dispersion aid exceeds 25 parts by weight, the viscosity of the pigment dispersion described later is greatly increased, the workability at the time of preparation of the photoresist composition, and the coating of the photoresist composition at the time of color filter production. Sex has a tendency to decrease.

In the range of the pigment dispersing aid of the present invention, one or two or more kinds of pigment dispersing aids selected from conventionally known pigment derivatives, etc., may be used in combination.

[Pigment Dispersion]

The pigment dispersion of the present invention contains a pigment, a pigment dispersant, the aforementioned pigment dispersing aid, and a solvent. The pigment dispersion of the present invention can be used not only as a raw material for a composition for a photoresist but also as a raw material for various inks and inks.

The pigment is not particularly limited, and the pigments exemplified in the description of the pigment dispersing aid can be used, and preferred pigments are also the same. More specifically, for example, CI Pigment Red 254, CI Pigment Red 177, CI Pigment Orange 36, CI Pigment Green 58, CI Pigment Green 36, CI Pigment Green 7, CI Pigment Yellow 150, CI Pigment Yellow 139, CI Pigment Yellow 138, CI Pigment Yellow 185, CI Pigment Blue 15:6, CI Pigment Violet 23, CI Pigment Orange 38, CI Pigment Orange 43, CI Pigment Orange 71 and the like. The pigments may be used alone or in combination of two or more.

The volume average particle diameter of the pigment is not particularly limited, but is preferably from 10 to 100 nm, more preferably from 20 to 50 nm. When the volume average particle diameter of the pigment is less than 10 nm, the cohesiveness of the pigment becomes too strong, even if three 吖 is used. The compound (1) also has a tendency to fail to obtain a pigment dispersion in which the pigment is uniformly dispersed. On the other hand, when the volume average particle diameter of the pigment exceeds 100 nm, the storage stability of the pigment dispersion is lowered even in three 吖 In the presence of the compound (1), there is also a tendency that the pigment tends to aggregate.

The volume average particle diameter of the pigment was Multisizer 3 (trade name, manufactured by Beckman Coulter Co., Ltd.), and filled in a beaker filled with ISOTON 2 (trade name, electrolytic solution for measurement, manufactured by Beckman Coulter Co., Ltd.), and slowly stirred while using a dropper (spuit) The pigment of the sample was dropped, and the concentration of the concentration meter of Multisizcr3 was about 10%, and then the measurement was performed by using an aperture of 400 μm.

The content of the pigment in the pigment dispersion is not particularly limited, and is preferably 30 to 80% by weight, and more preferably 40 to 70% by weight based on the total solid content of the pigment dispersion. In such a manner, when the content of the pigment is sufficiently increased, for example, the coloring density of the coating film using a pigment dispersion to produce a color filter or the like can be improved. Moreover, since the amount of volatilization of the solvent at the time of forming a coating film can be suppressed, the burden on the environment can be reduced.

The pigment dispersing agent is not particularly limited, and any of the resin type dispersing agent and the surfactant type dispersing agent exemplified in the description of the above-mentioned pigment dispersing aid can be used. Among these, the pigment dispersing effect of the pigment dispersing aid of the present invention or the effect of suppressing re-agglomeration of the pigment is sufficiently exerted. In other words, a resin type dispersant is preferred.

The content of the pigment dispersant in the pigment dispersion is not particularly limited, and is preferably 10 to 60 parts by weight, more preferably 20 to 50 parts by weight, per 100 parts by weight of the pigment. When the content of the pigment dispersant is less than 10 parts by weight, the effect of the pigment dispersant may not be sufficiently exhibited. On the other hand, when the content of the pigment dispersant exceeds 60 parts by weight, the viscosity of the pigment dispersion is increased in the opposite direction, and the workability (handleability) tends to be deteriorated.

As the dispersing aid, the above-described pigment dispersing aid of the present invention can be used. The pigment dispersing aid of the present invention does not greatly increase the viscosity of the pigment dispersion, and maintains uniform dispersion of the pigment. Further, the pigment dispersing aid of the present invention can be used together with various dispersing aids such as conventionally known pigment derivatives, within the range of excellent effects of the pigment dispersing aid of the present invention.

The content of the pigment dispersing aid in the pigment dispersion is not particularly limited, and is preferably 1 to 25 parts by weight, more preferably 3 to 20 parts by weight, per 100 parts by weight of the pigment. When the content of the pigment dispersing aid is less than 1 part by weight, the effect of the pigment dispersing aid may not be sufficiently exhibited. When the content of the pigment dispersing aid exceeds 25 parts by weight, the viscosity of the pigment dispersion greatly increases, the workability in the preparation of the photoresist composition, and the coating property of the photoresist composition in the production of the color filter are Reduce the tendency.

The solvent is not particularly limited, and an aqueous solvent and a non-aqueous solvent can be used arbitrarily. The aqueous solvent is, for example, a compound having a hydrophilic group having a high hydrophilicity such as a hydroxyl group, a compound having a polyethanol skeleton, or the like. Examples of the non-aqueous solvent include an ester solvent, an ether solvent, and a ketone solvent. Specific examples of the solvent include methoxypropyl acetate, propylene glycol monomethyl ether acetate (PMA), propylene glycol monomethyl ether (PM), butyl quercetin, water, and the like. The solvent may be used alone or in combination of two or more.

The pigment dispersion of the present invention may contain a conventionally known additive for a pigment dispersion as needed. Examples of such an additive include a pH adjuster, an antioxidant, an ultraviolet absorber, a preservative, an antifungal agent, and the like.

The pigment dispersion of the present invention can be obtained by, for example, dispersing a pigment, a pigment dispersant, a dispersing aid, a solvent, and an additive required for the reaction using a known dispersing machine such as a bead mill or a sand mill. The pigment dispersion of the present invention preferably has a combined solid content concentration of a pigment, a pigment dispersant, and a pigment dispersing aid from the viewpoints of dispersibility of the pigment, maintenance of dispersibility of the pigment, and suppression of viscosity increase. The amount is adjusted to be in the range of 15 to 30% by weight based on the total amount of the pigment dispersion.

[Manufacture of micronized pigments]

Sancha The compound (1) can form finer pigment particles by refining the pigment in the presence of the compound. Specifically, for example, when the pigment is refined by solvent salt milling, a pigment, a solvent, a grinding agent, etc. are mixed together. Compound (1) was placed in a kneading machine. Other operations are performed by the same operation as the usual kneading operation, compared to the case where no three-way is added. In the case of the compound (1), finer pigment particles can be obtained.

At this time, as long as it is to make the pigment and Sancha The method in which the compound (1) coexists is not particularly limited. Further, other additives such as a resin or a pigment derivative can also be used.

[Photoresist composition]

The photoresist composition of the present invention comprises the above pigment dispersion and a photosensitive compound. The photosensitive compound is an organic compound used in photolithography. As the photosensitive compound, a photosensitive compound for photolithography can be used, and a photosensitive compound of a preferred embodiment may contain a photosensitive resin, a photopolymerization initiator, a photopolymerizable monomer, and/or photopolymerizable property. Prepolymers (dimers, trimers, and oligomers) and the like.

As the pigment dispersion, the above-described pigment dispersion of the present invention is used. The content of the pigment dispersion in the resist composition is not particularly limited, and the weight ratio of the pigment to the total solid content of the resist composition is obtained from the viewpoint of the developability of the color filter finally obtained and the like. Preferably, it is set to 5 to 70% by weight, more preferably 15 to 60% by weight. When the weight ratio of the pigment is less than 5% by weight, the production of a color filter which contributes to the expression of a desired image of brightness, brightness, and contrast tends to be difficult. When the weight ratio of the pigment exceeds 70% by weight, the pigment dispersibility is lowered and the viscosity of the photoresist composition is increased, and the coatability at the time of production of the color filter and the characteristics of the color filter tend to be lowered.

As the photosensitive resin, it can be used as long as it is a photolithography method. The resin is not particularly limited, and examples thereof include an ethylene-vinyl acetate copolymer, an ethylene-vinyl chloride copolymer, an ethylene vinyl copolymer, a polystyrene, an acrylonitrile-styrene copolymer, an ABS resin, and a polymethacrylic resin. Vinyl methacrylate resin, polyvinyl chloride, chlorinated vinyl chloride, polyvinyl alcohol, cellulose acetate propionate, cellulose acetate butyrate, polyamine (nylon 6, nylon 66, nylon 12, etc.), poly Ethylene terephthalate, polybutylene terephthalate, polycarbonate, polyvinyl acetal, polyether ether ketone, polyether oxime, polyphenylene sulfide, polyarylate, polyvinyl butyl Aldehyde, epoxy resin, phenoxy resin, polyimine, polyamidimide, polyether phthalimide, phenol resin, urea resin, and the like.

Further, as the photosensitive resin, a copolymer of a monomer containing an ethylenically unsaturated double bond (hereinafter referred to as "vinyl monomer") and a carboxylic acid monomer can be used. Examples of the vinyl monomer include alkyl (meth)acrylate, benzyl (meth)acrylate, glycidyl (meth)acrylate, styrene, α-methylstyrene, and N-vinyl- 2-pyrrolidone and the like. In the alkyl (meth)acrylate, the alkyl moiety is methyl, ethyl, n-propyl, isopropyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n- A linear or branched alkyl group having 1 to 10 carbon atoms such as a hexyl group, a 2-ethylhexyl group, an n-octyl group, an n-fluorenyl group or a 2-hydroxyethyl group. The vinyl monomers may be used alone or in combination of two or more. Examples of the carboxylic acid-based monomer include acrylic acid, methacrylic acid, dimer of acrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid, vinyl acetate, and the like.

The carboxylic acid monomers may be used alone or in combination of two or more.

Further, in the present invention, a commercially available resin can be used as the photosensitive material. Resin. Examples of the commercially available resin include acrylic resins ("Aronox M-" 5600, 6200, 7100, 9050, all of which are trade names, manufactured by Daisei Co., Ltd.).

The content of the photosensitive resin in the photoresist composition is not particularly limited, and when the photosensitive resin is added to the photoresist composition, the total solid content of the photoresist composition is preferably 10 to 60% by weight, more preferably 15~50% by weight. When the content of the photosensitive resin is less than 10% by weight, the film strength of the pattern formed on the glass substrate is insufficient, and the long-term durability tends to be lowered. On the other hand, when the content of the photosensitive resin exceeds When the amount is 60% by weight, the dispersibility of the pigment in the resist composition becomes insufficient, and it is difficult to form a pattern having desired characteristics when the color filter is produced.

The photopolymerization initiator is not particularly limited as long as it can generate a radical by irradiation with energy such as ultraviolet rays, and examples thereof include benzoin isobutyl ether, benzoin isopropyl ether, benzophenone, and 4,4'- Bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, benzamidine benzoic acid, benzamidine benzoic acid methyl ester, 4-benzamide Base-4'-methyldiphenyl sulfide, benzyl methyl ketal, dimethylaminomethyl benzoate, 2-n-butoxyethyl-4-dimethylaminobenzene Formate, p-dimethylammonium isoamyl benzoate, 3,3'-dimethyl-4-methoxybenzophenone, methotrexate, 2-methyl 1-(4-(methylthio)phenyl)-2-morpholinylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinylphenyl) -butan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2- Methyl-1-phenylpropan-1-one, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 2-chlorothioxanthone (2-chloro thioxanthone), 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 1- Chloro-4-propoxythioxanthone and the like.

In the present invention, a commercially available photopolymerization initiator can be used, and examples thereof include "Irgacure" 184, 369, 651, and 907 (all products, manufactured by CIBA SPECIALTY CHEMICALS Co., Ltd.), Darocur (trade name, manufactured by Merck Co., Ltd.), a ketone compound such as Adeka 1717 (trade name, manufactured by ADEKA); 2,2'-bis(o-chlorophenyl)-4,5,4',5'-tetraphenyl-1,2' a biimidazole-based compound such as biimidazole (manufactured by Heijin Chemical Co., Ltd.). The photopolymerization initiator may be used alone or in combination of two or more.

The content of the photopolymerization initiator in the photoresist composition is not particularly limited, and is preferably from 0.05 to 10% by weight, more preferably from 0.5 to 5% by weight, based on the total solid content of the photoresist composition. When the content of the photopolymerization initiator is less than 0.05% by weight, the photocurability of the photoresist composition becomes insufficient, and the workability is lowered in the production step of the color filter by the photolithography method. tendency. Further, the developability and sensitivity of the color filter tend to be lowered. When the content of the photopolymerization initiator exceeds 10% by weight, agglomerates or precipitates are formed in the photoresist composition during storage of the photoresist composition, and the developability and sensitivity of the color filter produced using these are used. There is a tendency to decrease.

As the photopolymerizable monomer, a photopolymerizable monomer used in the field can be used, and examples thereof include an unsaturated carboxylic acid such as acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid or maleic acid. An acid; an ester of the aforementioned unsaturated carboxylic acid and a derivative thereof, such as methyl (meth) acrylate, hydroxyethyl (meth) acrylate or benzyl (meth) acrylate; (meth) acrylamide, such as acrylamide, N-hexyl (meth) acrylamide, vinyl (meth) acrylamide, allyl (meth) acrylamide; ethyl Vinyl ethers such as vinyl ether, 2-chloroethyl vinyl ether, and butyl vinyl ether; vinyl esters such as vinyl acetate, vinyl butyrate, and vinyl benzoate; benzene Styrene such as ethylene, methyl styrene or p-acetoxy styrene: vinyl ketones such as alkyl vinyl ketone and phenyl vinyl ketone; ethylene, propylene, isobutylene, butadiene, pentane An olefin such as a diene; an unsaturated quinone imine such as maleimide, N-propylene decyl acrylamide, N-ethyl decyl methacrylamide or N-propyl methacrylamide N-vinylpyrrolidone, acrylonitrile, methacrylonitrile, and the like. The photopolymerization property may be used alone or in combination of two or more. Among these photopolymerizable monomers, esters of an unsaturated carboxylic acid and an aliphatic polyol compound, and an amide of an unsaturated carboxylic acid and an aliphatic polyamine compound are preferable.

The photopolymerizable prepolymer includes, for example, (a) an addition reaction of an unsaturated carboxylic acid ester having a nucleophilic substituent or a guanamine with a monofunctional or polyfunctional isocyanate or epoxy. And (b) an unsaturated carboxylic acid ester having a nucleophilic substituent or a dehydration condensation reaction of a guanamine with a monofunctional or polyfunctional carboxylic acid, (c) an unsaturated carboxylic acid having an electrophilic substituent An addition reaction of an acid ester or a guanamine with a monofunctional or polyfunctional alcohol, an amine or a thiol, (d) an unsaturated carboxylic acid ester having a detachable substituent or a guanamine Substituted reactants with monofunctional or polyfunctional alcohols, amines or thiols. In the above (a) to (d), a compound group in which an unsaturated carboxylic acid ester is substituted with an unsaturated phosphonic acid, styrene, vinyl ether or the like can also be used as a photopolymerizable prepolymer. Again, the above In (a) to (d), examples of the nucleophilic substituent include a hydroxyl group, an amine group, a fluorenyl group, and the like, and examples of the electrophilic substituent include an isocyanate group and an epoxy group; and as the detachable substituent, for example, Such as a halogen atom, toluenesulfonyloxy group and the like.

The content of the photopolymerizable monomer and/or the photopolymerizable prepolymer in the photoresist composition is not particularly limited, and from the viewpoint of developability or sensitivity of the obtained color filter, a photoresist composition is preferable. The total solid content of the substance is 5 to 70% by weight, more preferably 10 to 60% by weight. In many cases, such a compound is used to enhance the adhesion between the film formed by the photoresist composition and the glass substrate, but it may be appropriately selected from those suitable for the other purpose for other purposes.

The solvent for the photoresist composition is not particularly limited, and examples thereof include alcohols such as methanol, ethanol, n-propanol, isopropanol, ethylene glycol, and propylene glycol; α-terpineol and β-product. Terpenes such as alcohol; ketones such as acetone, methyl ethyl ketone, cyclohexanone, and N-methyl-2-pyrrolidone; aromatic hydrocarbons such as toluene, xylene, and tetramethylbenzene ;赛璐苏, methyl 赛苏苏, ethyl 赛赛苏, carbitol, methyl carbitol, ethyl carbitol, butyl carbitol, propylene glycol monomethyl ether, propylene glycol monoethyl ether Ethylene ethers such as dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether; ethyl acetate, butyl acetate, sialic acid Ester, ethyl cyproterone acetate, butyl cyproterone acetate, carbitol acetate, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether An acid ester such as an acid ester, propylene glycol monoethyl ether acetate or 3-methoxybutyl acetate. Among these, preferably B Alcohol ethers or acetates, more preferably propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether. These solvents are all commercially available. The solvent may be used alone or in combination of two or more.

The content of the solvent in the photoresist composition is not particularly limited, and the pigment dispersibility of the photoresist composition, the coatability of the photoresist composition, and the image represented by the color liquid crystal display having the finally obtained color filter are considered. The brightness, the luminance, the contrast, and the like are preferably 100 to 900 parts by weight, more preferably 200 to 500 parts by weight, based on 100 parts by weight of the total solid content of the photoresist composition. When the content of the solvent is less than 100 parts by weight, the viscosity of the photoresist composition increases, and the pigment dispersibility and coatability tend to decrease. When the content of the solvent exceeds 900 parts by weight, the production of a color filter which contributes to the expression of the desired brightness, brightness, and contrast image tends to be difficult.

The photoresist composition of the present invention may contain various additives for the photoresist composition as needed. Examples of such an additive include a sensitizer, a chain transfer agent, a fluorine-based organic compound, a thermal polymerization initiator, a thermal polymerization component, a heat-resistant polymerization agent, a filler, a surfactant, a adhesion promoter, and an anti-blocking agent. An oxidizing agent, an ultraviolet absorber, an anti-agglomerating agent, and the like. The additive may be used alone or in combination of two or more.

The photoresist composition of the present invention is characterized in that a pigment dispersion and a photosensitive compound are added to a solvent (for example, selected from a photosensitive resin, a photopolymerization initiator, a photopolymerizable monomer, and a photopolymerizable prepolymer). At least one of the groups formed, in accordance with other additives required, and obtained by uniformly dissolving and/or dispersing the components in the resulting mixture. Mixed The dissolution and dispersion of each component in the composition can be carried out by a known method, and for example, a method of shaking using a paint conditioner or the like is exemplified.

Using the photoresist composition of the present invention, a specified pattern can be formed on a designated glass substrate by photolithography, and a color filter can be produced.

[Examples]

The present invention will be specifically described below by way of Synthesis Examples, Examples and Comparative Examples. In addition, the following "parts" and "%" are set as the weight basis unless otherwise specified.

(Synthesis Example 1) [三吖 Synthesis of Compound (2a)

Adding 18.4 parts of cyanuric chloride to 100 parts of water and 17.3 parts of o-aminobenzenesulfonic acid (2-aminobenzenesulfonic acid) in an amount of one chlorine atom of cyanuric chloride, at 10 ° C The reaction was allowed to proceed for 1 hour. To the obtained reaction product, 29.8 parts of 5-amino-2-benzimidazolidinone was reacted with the two chlorine atoms of the reactant, and the reaction was allowed to proceed at 85 ° C for 1 hour. The obtained reaction product was obtained by filtration, and the obtained residue was washed with water, and then left to stand in a thermostat at 100 ° C overnight to dry, to obtain three oximes. Compound (2a) was 44.7 parts.

AXIMA CFR plus matrix-assisted laser desorption ionization-time-of-flight mass spectrometer (manufactured by Shimadzu Corporation) was used to determine α-cyano-4-hydroxycinnamic acid (CHCA) as a matrix in positive ion mode.吖 A molecular ion peak of the compound (2a). As a result, a peak was confirmed at m/z = 546. The following Synthesis Examples 2 to 7 are also operated in the same manner, and three 吖 are obtained. Molecular ion peaks of compounds (2b) to (2c) and (3a) to (3d).

(Synthesis Example 2) [三吖 Synthesis of Compound (2b)

Triasterium was obtained in the same manner as in Synthesis Example 1, except that 29.8 parts of 5-aminobenzamide was used instead of 29.8 parts of 5-amino-2-benzimidazolidinone. Compound (2b) was 47.7 parts. m/z = 520.

(Synthesis Example 3) [三吖 Synthesis of Compound (2c)

The same procedure as in Synthesis Example 1 was carried out except that 16.8 parts of 3-amino-4-methoxybenzimidamide was used instead of 29.8 parts of 5-amino-2-benzimidazolidinone to obtain triterpene. Compound (2c) was 32.5 parts. m/z = 582.

(Synthesis Example 4) [三吖 Synthesis of Compound (3a)

To 100 parts of water, 18.4 parts of cyanuric chloride was added, and 17.3 parts of o-aminobenzenesulfonic acid was reacted with one chlorine atom of cyanuric chloride, and the reaction was allowed to proceed at 10 ° C for 1 hour. To the obtained reactant, 23.3 parts of 2-aminophenyl phenyl sulfone and 320 g of 50% acetic acid were added in an amount to react with one chlorine atom of the reactant, and at 85 ° C. The reaction was allowed to proceed for 1 hour. The obtained reaction product was obtained by filtration, and the obtained residue was washed with water, and then left to stand in a thermostat at 100 ° C overnight to dry, to obtain three oximes. Compound (3a) was 16.6 parts. m/z = 499.

(Synthesis Example 5) [三吖 Synthesis of Compound (3b)

The operation was carried out in the same manner as in Synthesis Example 4 except that the amount of 2-aminophenylphenylhydrazine added was changed from 23.3 parts to 46.6 parts. Compound (3b) was 53.9 parts. m/z = 714.

(Synthesis Example 6) [三吖 Synthesis of Compound (3c)

The same procedure as in Synthesis Example 4 was carried out except that 17.3 parts of sulfamic acid was used instead of 17.3 parts of o-aminobenzenesulfonic acid to obtain triterpene. Compound (3c) was 19.2 parts. m/z = 499.

(Synthesis Example 7) [三吖 Synthesis of Compound (3d)]

Triasterium was obtained in the same manner as in Synthesis Example 4 except that 17.7 parts of p-toluidine-2-sulfonic acid was substituted with 17.3 parts of o-aminobenzenesulfonic acid. Compound (3d) 23.0 parts. m/z = 513.

(Example 1)

The specified amount of each component shown in the following Table 3 was placed in a mixer having a content of 500 ml, and stirred at 2000 rpm for 10 minutes using a disperser to perform preliminary dispersion.

768 g of zirconia beads having a diameter of 0.5 mm were placed in the preliminary dispersion obtained above, and stirred at 2000 rpm for 2 hours to carry out main dispersion. To the main dispersion obtained, 48 g of PMA was added, and the mixture was further stirred at 1500 rpm for 10 minutes. The resulting final dispersion was filtered using a 2.5 μm mesh filter (trade name: PALL HDCII Membrene Filler, manufactured by PALL Co., Ltd.) to remove zirconia beads, thereby obtaining a red pigment dispersion.

(Examples 2 to 7)

In addition to the three 得到 obtained using Synthesis Examples 2 to 7. Compound (2b), (2c), (3a), (3b), (3c) or (3d) replaces triterpenoid The red pigment dispersion of Examples 2 to 7 was obtained in the same manner as in Example 1 except for the compound (2a).

(Reference example 1)

In addition to using the three formulas shown in the general formula below Compound (III) replaces triterpenoid A red pigment dispersion was obtained in the same manner as in Example 1 except for the compound (2a). Still, the following three The compound (III) is a general pigment dispersing aid commercially available as a mixture of a compound in which the symbol Y is a chlorine atom and a compound in which the symbol Y is a hydroxyl group, and is used as a control.

Each of the red pigment dispersions of Examples 1 to 7 and Reference Example 1 was used as a film thickness method capable of obtaining the intended chromaticity (Examples 1 to 7 and Reference Example 1; x = 0.650) on the glass substrate. , coated with a rotary cloth machine, and dried by heating at 90 ° C for 2 minutes and 30 seconds (pre-baking) using a box dryer, and further dried at 230 ° C for 30 minutes (post-baking) using a box dryer, cooling A colored glass plate (color filter) was obtained.

(Evaluation 1) [Growth Enhancement Rate of Pigment Dispersion]

The initial viscosity (dynamic viscosity) A (mPa.s) of each of the pigment dispersions produced in Examples 1 to 7 and Reference Example 1 was measured. Next, each of the pigment dispersions of Examples 1 to 7 and Reference Example 1 was placed in an environment of 25 ° C, and after standing for 1 day, the post-placement viscosity (dynamic viscosity) of each pigment dispersion was measured (mPa. s). The viscosity (dynamic viscosity) of the pigment dispersion was measured in accordance with JIS Z8809 using an E-type viscometer (trade name: RE-01, manufactured by Toki Sangyo Co., Ltd.) at 25 ° C. The viscosity increase rate was calculated based on the following formula. Viscosity increase = (viscosity B after placement) / (initial viscosity A). The results are shown in Table 4. The initial viscosity of Examples 1 to 7 in Table 4 is expressed as a relative value when the initial viscosity of the pigment dispersion of Reference Example 1 is taken as a standard (100).

[Measurement of comparison]

The contrast of the colored glass plates (color filters) after baking in Examples 1 to 7 and Reference Example 1 was measured using a comparative measuring device. The contrast measuring device is a color luminance meter (trade name: LS-100, manufactured by Konica Minolta Sensing Co., Ltd.), a lamp (trade name: HF-SL-100WLCG, manufactured by Dentsu Industry Co., Ltd.), and a polarizing plate (trade name: POLAX-38S, made by Luceo.

On the backlight, a polarizing plate was provided in such a manner that the polarizing plate (POLAX-38S) and the colored glass plate were separated by 1 mm. A revolving polarizing plate is disposed above it. After confirming that the brightness of the backlight is sufficiently stabilized, the rotating polarizing plate disposed above is adjusted to the crossed Nicols (Crossed) The position of Nichol), and the luminance of the colored glass plate was measured, and then rotated 90° to the parallel position, and the luminance of the colored glass plate was measured. The ratio (%) of the two was obtained as a comparison, and the results are shown in Table 4. The comparative values of Examples 1 to 7 in Table 4 are shown as relative values when the comparison of the colored glass sheets obtained by using the pigment dispersion of Reference Example 1 is taken as a standard (100).

[Measurement of luminance (Y)]

The luminance (Y) of the colored glass plates of Examples 1 to 7 and Reference Example 1 obtained above was measured as follows. The colored glass plate was placed in a spectrophotometer (trade name: CM-3700d, manufactured by Konica Minolta Sensing Co., Ltd.), and the transmission chromaticity of the XYZ coordinate axis at 2° of the C light source was measured. The Y value at this time is taken as the luminance (Y). The results are shown in Table 4. The luminance values of Examples 1 to 7 in Table 4 are expressed as relative values when the luminance of the colored glass plate obtained by using the pigment dispersion of Reference Example 1 is taken as a standard (100).

As can be seen from Table 4, by using the three 本 of the present invention Compounds, the brightness will increase, and the contrast can be increased to a lesser image, that is, a color filter that contributes to the representation of a vivid color image.

(Examples 8 to 9 and Comparative Examples 1 to 2)

In the same manner as in Example 1, except that the pigment dispersion composition (g) shown in Table 5 was changed, preliminary dispersion, main dispersion, addition of PMA to the main dispersion, and stirring and filtration after addition of PMA were performed. A green pigment dispersion (Example 8 and Comparative Example 1) and a blue pigment dispersion (Example 9 and Comparative Example 2) were obtained.

Except for three in Table 5 The components used in addition to the compound (2c) are specifically as described below.

[pigment]

*1 Lionol Green 6YK; trade name, green pigment (C.I. Pigment Green 36), Toyo-Chem (share) system

*2 Fastogen blue EP-207; trade name, copper phthalocyanine blue pigment (C.I. Pigment Blue 15:6), DIC (share) system

[Dispersing Aid]

*3 Solsperse S12000; trade name, pigment derivative with sulfonic acid group, manufactured by Lubrizol

[Resin type dispersant]

*4 BYK-LPN6919 (solid content concentration 60.9%); trade name, BYK-Chemie Japan (share) system

*5 BYK-LPN21116 (solid content concentration 40.0%); trade name, BYK-Chemie Japan (share) system

*6 Ripoxy SPC-2000 (solid content concentration: 35%); trade name, vinyl ester resin, Showa Denko (share) system

(Evaluation 2)

A color filter was produced using the pigment dispersions obtained in the above Examples 8 to 9 and Comparative Examples 1 and 2, and the properties were evaluated.

[Production of color filter]

In the pigment dispersions obtained in Examples 8 to 9 and Comparative Examples 1 and 2, the following components were added and mixed to prepare a photoresist composition (a rotary liquid, hereinafter referred to as "SPC liquid"). In addition, the total solid content of the pigment dispersion and the total solid content of each of the other components were adjusted so that the weight ratio became 1:1, and the two were mixed.

Composition of the photoresist composition;

Each of the obtained SPC liquids was obtained on a square glass plate having a thickness of 1 mm and 100 mm to obtain a desired chromaticity (Example 8 and Comparative Example 1; y=0.500, Example 9 and Comparative Example 2; y= The film thickness of 0.120) was applied by a spreader coating (trade name: SpinCoater MS-150A, manufactured by Mikasa Co., Ltd.), and dried by heating at 90 ° C for 2.5 minutes using a box dryer (prebaking). Further, it was dried by heating at 230 ° C for 30 minutes (post-baking) using a box dryer to obtain Examples 8 to 9 and Each of the colored glass plates (color filters) of Comparative Examples 1 and 2 was used.

[Evaluation of chromaticity (x, y), luminance (Y)]

For each of the colored glass plates of Examples 8 to 9 and Comparative Examples 1 and 2, a colorimeter (trade name: CM-3700d, manufactured by Konica Minolta Co., Ltd.) was used, and tristimulus was obtained by the xyY color method. value. The results are shown in Table 6.

[Compared]

In each of the colored glass plates (color filters) after baking in Examples 8 to 9 and Comparative Examples 1 and 2, the polarizing plate was set to have a luminance and a polarizing plate at the position of the crossed Nicols in the same manner as described above. The contrast (CR) is obtained as the ratio (%) of the luminance at the parallel position. The results are shown in Table 6.

As can be seen from Table 6, since the luminance (Y value) of Examples 8 and 9 is large, by using the three 本 of the present invention The brightness of the image of the compound (1) on a color liquid crystal display is enhanced, and the object of the present invention is clearly achieved.

Claims (11)

a three-way diagram of the following general formula (1) Compound, [In the formula (1), R ^{1 is} shown as a base: ,base: Or base: ; R ^{2 is} shown as: ,base: ,base: And a hydroxyl group or a halogen atom; R ³ , R ⁴ and R ⁵ may be the same or different as a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and R ⁶ is a hydrogen atom; An alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; R ⁷ is a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms; and 1 is a triazine represented by the formula (1). The average number of sulfonic acid groups introduced into a molecule of a compound is shown as a number from 1 to 2; m and n are each an integer from 1 to 2; however, when R ² is a hydroxyl group or a halogen atom, R ¹ is as follows: base ]. As requested in item 1 a compound which is a triterpene represented by the following general formula (2) Compound, [In the formula (2), R ³ , R ⁴ and R ⁵ may be the same or differently represented as a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; R ¹⁰ and R ¹¹ Can be shown as the same or different R ⁷ is represented by a hydrogen atom or an alkoxy group having a carbon number of 1 to 4; and l is a triazine represented by the formula (2) The average number of sulfonic acid groups introduced into a molecule of a compound is shown as a number from 1 to 2; n is an integer from 1 to 2. As requested in item 2 a compound in which the aforementioned three formulas represented by the general formula (2) In the compound, R ¹⁰ and R ¹¹ may be the same or different and are shown as R ⁷ is represented by a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms; n is an integer of 1 to 2]. As requested in item 2 a compound in which the aforementioned three formulas represented by the general formula (2) In the compound, R ¹⁰ and R ¹¹ are the same groups. As requested in item 1 a compound which is a triterpene represented by the following general formula (3) Compound, [In the formula (3), R ³ , R ⁴ and R ⁵ may be the same or differently represented as a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and R ⁶ is represented by hydrogen; An atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; and l is a triterpene represented by the formula (3) The average number of sulfonic acid groups introduced into a molecule of a compound is shown as a number from 1 to 2; m is an integer from 1 to 2; and X is a hydroxyl group, a halogen atom or a group: R ^{10 is} shown as: ,base: Or base: R ⁷ is represented by a hydrogen atom or an alkoxy group having 1 to 4 carbon atoms; n is an integer of 1 to 2; and when X is a hydroxyl group or a halogen atom, R ¹⁰ is represented by the following group; ]. As requested in item 5 a compound in which the aforementioned three formulas represented by the general formula (3) In the compound, R ¹⁰ is the group of the following, A third containing any one of the requirements 1 to 6 A pigment dispersing aid for the compound. A pigment dispersion comprising a pigment, a pigment dispersant, the pigment dispersing aid of claim 7, and a solvent. The pigment dispersion of claim 8, wherein the pigment has a volume average particle diameter of 10 to 100 nm. The pigment dispersion according to claim 8, wherein the content of the pigment is 30 to 80% by weight based on the total solid content of the pigment dispersion, and 10 to 60 parts by weight of the pigment dispersant is contained in 100 parts by weight of the pigment. And comprising 1 to 25 parts by weight of the aforementioned pigment dispersing aid. A photoresist composition comprising the pigment dispersion of any one of items 8 to 10 and a photosensitive compound.