JP2015189770A - xanthene compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a novel xanthene compound which has excellent clarity, color development and high solubility in an aqueous medium, and an oil dye or aqueous dye composition using the compound.SOLUTION: There is provided a xanthene compound represented by the general formula (1). (Ris H or an unsubstituted C1-8 alkyl group; and Rto Rare each independently H, a carboxyl group, a C1-4 alkyl group having a substituent selected from a halogen atom, a hydroxy group and an alkoxy group, or an unsubstituted C1-4 alkyl group, provided that at least one of Rto Ris a carboxyl group.)

Description

  The present invention relates to a novel xanthene compound useful as a dye.

  In general, dyes are roughly classified into dyes and pigments. Although pigments have high fastness such as light resistance and solvent resistance, they are difficult to handle because they are insoluble in solvents. For example, assuming application to optical applications such as color filters, ensuring high transparency is indispensable, and technology for minimizing pigments that are insoluble in solvents and advanced dispersion technology for dispersing in solvents are necessary. It becomes. On the other hand, dyes are generally soluble in solvents and are therefore easy to handle and are known to exhibit high coloring power and transparency. However, even dyes do not necessarily have good solubility in all solvents. However, most of them are hardly soluble in a specific solvent.

  As a method of coloring an object using a dye having poor solubility in a solvent, for example, a wet coloring method using an advanced dispersion technique such as the above-described pigment is used, or from a gas phase such as vacuum deposition onto the object. There is a dry coloring method in which dye molecules are deposited. The wet coloring method requires a long dispersion step in order to finely disperse a dye having poor solubility in a solvent in the solvent, and it is necessary to add various additives as a dispersion aid. Is not wide. In addition, the dry coloring method requires large equipment such as a vacuum device, and the number of durable dyes that can withstand high temperature conditions that vaporize the dye is limited, so that the range of application is not necessarily wide. I can not say.

  It is also possible to introduce a bulky substituent into a dye skeleton having poor solubility in a solvent to obtain solubility in the solvent. However, since it is affected by the introduced substituent effect, the physical properties are not necessarily the original compounds. Are not necessarily equal.

Xanthene compounds are widely used as red to violet dyes because of their clear hue, high color development, and robustness against light, heat, etc. Various paints, water-based inks, oil-based It is used in a wide range of applications such as inks, inkjet inks, and color filters. As such a dye, for example, a xanthene compound represented by the following formula (100) as described in Patent Document 1 is known (Patent Document 1, Example 1, Example 3, and Example 5). .
However, as a result of investigations by the present inventors, the xanthene compound represented by the following formula (100) has insufficient solubility in a specific solvent.

WO2013-146218

  An object of this invention is to provide the novel xanthene compound which is excellent in sharpness and coloring property, and has favorable solubility with respect to a specific solvent.

As a result of intensive studies to solve the above-mentioned problems, the present inventors have found that a novel xanthene compound having a specific structure has significantly higher solubility in an aqueous medium than a conventionally known xanthene dye (compound). The inventors have found that the present invention is superior and have completed the present invention.
That is, the present invention
[1] A xanthene compound represented by the formula (1)

(In Formula (1), R ¹ represents a hydrogen atom or an unsubstituted alkyl group having 1 to 8 carbon atoms. R ^{2 to} R ¹¹ are each independently a hydrogen atom; a carboxyl group; a halogen atom, a hydroxy group, and an alkoxy group. Represents an alkyl group having 1 to 4 carbon atoms or an unsubstituted alkyl group having 1 to 4 carbon atoms having a substituent selected from the group consisting of: and at least one of R ^{7 to} R ¹¹ is a carboxyl group. ),
[2] The xanthene compound according to [1], wherein R ¹ in Formula (1) is an unsubstituted alkyl group having 1 to 4 carbon atoms, and one of R ^{7 to} R ¹¹ is a carboxyl group,
[3] An oil-based dye composition containing the xanthene compound according to [1] or [2] and an oil-soluble organic solvent,
[4] An aqueous dye composition comprising the xanthene compound according to [1] or [2] and an aqueous medium,
[5] Printed matter obtained using the oil-based dye composition according to [3] or the aqueous dye composition according to [4],
[6] A color filter obtained using the oil-based dye composition according to [3] or the aqueous dye composition according to [4],
About.

  The xanthene compound of the present invention (hereinafter also simply referred to as “the compound of the present invention”) is excellent in sharpness and color developability, and is excellent in solubility in an aqueous medium, particularly water.

The compound of the present invention is represented by the formula (1).
In Formula (1), R ¹ is a hydrogen atom or an unsubstituted alkyl group having 1 to 8 carbon atoms (an unsubstituted alkyl group is an alkyl group having only a carbon atom and a hydrogen atom and having no substituent). Hereinafter, the term “unsubstituted” is used in the same meaning.), And the alkyl group having 1 to 8 carbon atoms is linear or branched if the alkyl group has 1 to 8 carbon atoms. It is not limited to any shape.

Specific examples of the alkyl group having 1 to 8 carbon atoms represented by R ^{1 in the} formula (1) include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec -Butyl group, t-butyl group, n-pentyl group, iso-pentyl group, t-pentyl group, hexyl group, heptyl group, octyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, 2-ethylhexyl Group and 2-methylcyclohexyl group.
R ^{1 in} formula (1) is preferably a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms, and more preferably an unsubstituted alkyl group having 1 to 4 carbon atoms.

In formula (1), R ^{2 to} R ¹¹ each independently represent a hydrogen atom, a carboxyl group or an alkyl group having 1 to 4 carbon atoms, and the alkyl group having 1 to 4 carbon atoms is an alkyl having 1 to 4 carbon atoms. As long as it is a group, it is not limited to either linear or branched. The alkyl group may have a substituent. However, at least one of R ^{7 to} R ¹¹ is a carboxyl group.

Specific examples of the alkyl group having 1 to 4 carbon atoms represented by R ^{2 to} R ^{11 in} Formula (1) include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, and iso-butyl. Group, sec-butyl group and t-butyl group.

Examples of the substituent that the alkyl group represented by R ^{2 to} R ^{11 in} Formula (1) may have include a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom), a hydroxy group, and an alkoxy group (for example, Methoxy group, ethoxy group, iso-propoxy group, n-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, t-butoxy group and the like.

R ^{2 to} R ¹¹ in Formula (1) are each independently a hydrogen atom, a carboxyl group or an unsubstituted alkyl group having 1 to 4 carbon atoms, and at least one of R ^{7 to} R ¹¹ is a carboxy group. R ^{2 to} R ⁶ are each independently a hydrogen atom or an unsubstituted alkyl group having 1 to 4 carbon atoms, and R ^{7 to} R ¹¹ are each independently a hydrogen atom, a carboxyl group or an unsubstituted group. It is more preferable that at least one of R ^{7 to} R ¹¹ is a carboxy group, and R ^{2 to} R ¹⁰ are each independently a hydrogen atom or an unsubstituted carbon number. a 1-4 alkyl ^group, more preferably ^{R 11} is a carboxyl ^group, R 2 ^{to R 10} is a hydrogen ^{atom, R 11} is a carboxyl group The most preferred.

The xanthene compounds represented by the formula (1) of the present invention, more preferably a combination of the above R ¹ to R ¹¹ each preferred, more preferably a combination of more preferable ones.

The xanthene compound represented by the formula (1) of the present invention is, for example, Chemical Biology, 5 (11), 1065. Can be synthesized by reacting a condensate synthesized according to the method described in 1) with an amino (benzoic acid) derivative and a mercapto (benzoic acid) derivative. That is, the xanthene compound of the present invention contains 3,6-dichlorospiro [9H-xanthene-9,3 ′-[3H] [2,1] benzooxathiol] 1 ′, 1′-dioxide (in the following synthesis scheme examples). A compound represented by the formula (2)) and a corresponding amino (benzoic acid) derivative (a compound represented by the formula (3) in the following synthesis scheme example) and a mercapto (benzoic acid) derivative (a formula ( The compound represented by 5) can be easily synthesized by condensation at a predetermined temperature (for example, 0 to 150 ° C.). An example of the synthesis scheme is shown below. In addition, R < ¹ > -R < ¹¹ > in Formula (3)-(5) is synonymous with R < ¹ > -R < ¹¹ > in the said Formula (1).

  The synthesis scheme exemplified above is a method for synthesizing the xanthene compound represented by the formula (1) of the present invention by the primary condensation step shown in the first step and the secondary condensation step shown in the second step. .

  In the primary condensation step shown in the first step, the compound represented by Formula (2) and the compound represented by Formula (3) are condensed by heating in the presence of an organic solvent or a condensing agent as necessary. . Next, in the secondary condensation step shown in the second step, the compound represented by the formula (4) obtained in the primary condensation step and the compound represented by the formula (5) are combined with an organic solvent or a condensation product. If necessary, the compound represented by the formula (1) can be obtained by condensation by heating again in the presence of an agent.

  The organic solvent used in the condensation reaction of the synthetic scheme exemplified above is, for example, methanol, ethanol, n-propanol, iso-propanol, n-butanol, N-methylpyrrolidone and the like in the primary condensation step shown in the first step. It is preferable to use sulfolane alone or in combination. In the secondary condensation step shown in the second step, for example, methanol, ethanol, n-propanol, iso-propanol, n-butanol, ethylene glycol, N-methylpyrrolidone, N, N-dimethylacetamide, N, N-dimethyl Formamide, dimethyl sulfoxide, sulfolane, chlorobenzene, dichlorobenzene, trichlorobenzene, nitrobenzene and the like are preferably used alone or in combination.

  The reaction temperature in the primary condensation step is preferably 20 to 100 ° C, and more preferably 20 to 90 ° C. The reaction temperature in the secondary condensation step is preferably 30 to 200 ° C, and more preferably 40 to 150 ° C.

  Examples of the condensing agent that can be used in the primary condensation / condensation step and the secondary condensation step in the synthesis scheme include zinc chloride, magnesium chloride, and aluminum chloride. It is preferable that the usage-amount of a condensing agent is 0.1-5 equivalent with respect to the compound represented by Formula (2) and Formula (4).

  Although the specific example of the xanthene compound shown by the said Formula (1) of this invention is shown below, this invention is not limited to these.

  The oily or aqueous dye composition of the present invention contains a xanthene compound represented by the formula (1) of the present invention, an oil-soluble organic solvent in the case of an oily dye composition, and an aqueous medium in the case of an aqueous dye. The content of the xanthene compound represented by the formula (1) in the oily or aqueous dye composition of the present invention is usually 0.1 to 50% by mass, preferably 0.2 to 40% by mass, more preferably 0.5. ˜20 mass%.

  The oil-based dye composition of the present invention can be prepared by dissolving or dispersing the xanthene compound represented by the formula (1) of the present invention in at least one oil-soluble organic solvent. Examples of the oil-soluble organic solvent used include alcohols such as ethanol, pentanol, octanol, cyclohexanol, benzyl alcohol, and tetrafluoropropanol; ethylene glycol monoethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol mono Glycol derivatives such as ethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, triethylene glycol monoethyl ether, ethylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol diacetate; ketones such as methyl ethyl ketone and cyclohexanone ; Butyl phenyl ether, benzine Ethers such as ether and hexyl ether; esters such as ethyl acetate, butyl acetate, ethyl benzoate, butyl benzoate, ethyl laurate, and butyl laurate; acetonitrile, DMF, dimethyl sulfoxide, sulfolane, NMP, 2-pyrrolidone, etc. These organic solvents may be used, and these solvents may be used alone or in combination of two or more.

  The aqueous dye composition of the present invention can be prepared by dissolving or dispersing the xanthene compound represented by the formula (1) of the present invention in an aqueous medium. Examples of the aqueous medium include water or a water-soluble organic solvent. Examples of the water-soluble organic solvent include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, t-butanol, pentanol and benzyl alcohol; ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, polyethylene glycol Polyhydric alcohols such as polypropylene glycol, glycerin, trimethylolpropane, 1,3-pentanediol and 1,5-pentanediol; ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, tri Ethylene glycol monoethyl ether, triethylene glycol monobutyl ether Glycol derivatives such as Le and dipropylene glycol monomethyl ether; ethanolamine, diethanolamine, amines such as triethanolamine and morpholine; 2-pyrrolidone, NMP, 1,3-dimethyl - imidazolidinone. These solvents may be used alone or in combination of two or more.

An acid or an alkali may be added to the aqueous dye composition. Examples of the acid that can be added to the aqueous dye composition include inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and organic acids such as oxalic acid and citric acid.
Examples of the alkali that can be added to the aqueous dye composition include alkali metal hydroxides such as sodium hydroxide, lithium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium carbonate, lithium carbonate and potassium carbonate. The acid or alkali content that can be added to the aqueous dye composition is usually 0.1 to 30% by mass, preferably 0.2 to 20% by mass, and more preferably 0.3 to 15% by mass.

  In the oily or aqueous dye composition of the present invention, a coloring material other than the xanthene compound represented by the formula (1) may be used in combination as necessary for the purpose of adjusting the hue. Examples of color materials that can be used in combination include water-soluble dyes such as acid dyes, reactive dyes, direct dyes, cationic dyes and basic dyes; oil-soluble dyes such as disperse dyes and solvent dyes; organic pigments and carbon black. Although it is mentioned, it is not limited to these, It adds in the state melt | dissolved or disperse | distributed to the solvent. The amount of the coloring material that can be used in combination in the oily or aqueous dye composition of the present invention is not particularly limited, and is usually 15% by mass or less, preferably 5 to 10%, based on the xanthene compound represented by the formula (1). Mass is used.

  In the oil-based dye composition and the aqueous dye composition of the present invention, a dispersant can be used together as necessary for the purpose of improving the dispersibility of the xanthene compound represented by the formula (1).

  Dispersants that can be used in the oil-based dye composition include sodium dodecylbenzene sulfonate, sodium laurate, formalin condensate of naphthalene sulfonic acid, formalin condensate of alkyl naphthalene sulfonic acid, formalin condensate of creosote oil sulfonic acid, poly Ammonium salt of oxyethylene alkyl ether sulfate, ammonium salt of polyoxyethylene alkyl phenyl ether sulfate, polyoxyalkyl ether phosphate ester salt and other known anionic surfactants, vinyl naphthalene derivatives, α, β-ethylenically unsaturated carboxylic acid Aliphatic alcohol esters, styrene, styrene derivatives, acrylic acid, acrylic acid derivatives, methacrylic acid, methacrylic acid derivatives, maleic acid, maleic acid derivatives, maleic anhydride, maleic anhydride A block copolymer consisting of at least two monomers selected from inic acid derivatives, itaconic acid, itaconic acid derivatives, fumaric acid, fumaric acid derivatives, etc., or a random copolymer, or a high salt thereof. Examples thereof include molecular dispersants, and one or more of these are usually 500% by mass or less, preferably 10 to 450% by mass with respect to the xanthene compound represented by formula (1) and the colorant used in combination as necessary. More preferably, 100 to 400% by mass is used.

  As a dispersant that can be used in the aqueous dye composition, in addition to a surfactant, a dispersant commonly used for preparing a pigment dispersion, for example, a polymer dispersant can be suitably used. Specific examples of the polymer dispersant include polyvinyl alcohols, polyvinyl pyrrolidones, polyacrylic acid, acrylic acid-acrylonitrile copolymer, acrylate-acrylonitrile copolymer, vinyl acetate-acrylic ester copolymer. , Acrylic resins such as acrylic acid-acrylic acid ester copolymer, styrene-acrylic acid copolymer, styrene-methacrylic acid copolymer, styrene-methacrylic acid-acrylic acid ester copolymer, styrene-α-methylstyrene -Styrene-acrylic resins such as acrylic acid copolymer, styrene-α-methylstyrene-acrylic acid-acrylic acid ester copolymer, styrene-maleic acid copolymer, styrene-maleic anhydride copolymer, isobutylene-malein Acid resin, rosin-modified maleic acid resin, vinyl naphthalene Acrylic acid copolymer, vinyl naphthalene-maleic acid copolymer, vinyl acetate-ethylene copolymer, vinyl acetate-fatty acid vinyl ethylene copolymer, vinyl acetate-maleic acid ester copolymer, vinyl acetate-crotonic acid copolymer Examples include polymers, vinyl acetate copolymers such as vinyl acetate-acrylic acid copolymers, and salts thereof. It is usually used in an amount of 100% by mass or less, preferably 10 to 70% by mass, based on the xanthene compound represented by the formula (1) and the coloring material used in combination.

  Examples of the method for finely dispersing the xanthene compound represented by the formula (1) include methods using a sand mill (bead mill), a roll mill, a ball mill, a paint shaker, an ultrasonic disperser, a microfluidizer, and the like. Among these, a sand mill (bead mill) is preferable. In addition, when dispersion is performed using a sand mill (bead mill), it is preferable to perform processing under conditions that can improve the grinding efficiency, such as using beads with a small diameter or increasing the filling rate of beads, and further after the grinding treatment. It is also preferable to remove elementary particles by filtration, centrifugation, or the like.

  The dye composition of the present invention may contain a surface adjusting agent, an antifoaming agent, an antiseptic / antifungal agent, a pH adjusting agent and the like as other additives. As the surface conditioner, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, a known nonionic, polysiloxane or polydimethylsiloxane based copolymer of ethylene oxide and propylene oxide, etc. As surfactants and antifoaming agents, silicone-based and acetylene-based known antifoaming agents, and as antiseptic and antifungal agents, sodium dehydroacetate, sodium benzoate, sodium pyridinethione-1-oxide, zinc pyridinethione Known antiseptic / antifungal agents such as 1-oxide, 1,2-benzisothiazolin-3-one, amine salt of 1-benzisothiazolin-3-one, and pH adjusters include sodium hydroxide, potassium hydroxide, Alkali hydroxide such as lithium hydroxide Li metals, triethanolamine, diethanolamine, dimethylethanolamine, known pH adjusting agent such as tertiary amines such as diethylethanolamine and the like, which can be added as required, respectively.

  In addition, the oil-based or aqueous dye composition of the present invention has a polyamide-based, polyurethane-based, polyester-based, epoxy-based, or polyacrylic resin that is compatible with the medium in the composition for the purpose of improving the fixability of the dye to the object to be colored. It is preferable to contain a binder resin such as a monomer and an oligomer having an ethylenic unsaturated group, and when the binder resin is polymerizable, a polymerization initiator or a curing agent may be used in combination. More preferred. The binder resin is usually used in an amount of 10000% by mass or less based on the xanthene compound represented by the formula (1) in the dye composition and the color material used in combination as necessary. In addition, what is necessary is just to use an appropriate quantity for a polymerization initiator, a hardening | curing agent, etc. according to the usage-amount of binder resin. The oily or aqueous dye composition of the present invention can be prepared by dissolving or dispersing and mixing the above components in a solvent.

  The xanthene compound represented by the formula (1) of the present invention is used in various paints, water-based inks, oil-based inks, inkjet inks, and color filter coloring compositions as oil-based dye compositions or water-based dye compositions. The oil-based dye composition and the aqueous dye composition are used for materials to be colored such as plain paper, coated paper, plastic film, and plastic substrate. Examples of a method for applying the dye composition of the present invention to a material to be colored include various printing methods such as offset printing, letterpress printing, flexographic printing, and ink jet printing, and coating methods using a spin coater, a roll coater, and the like.

  EXAMPLES Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited to these Examples. In the examples, the maximum absorption wavelength was measured with a spectrophotometer “trade name UV-3150, manufactured by Shimadzu Corporation”. In the examples, “part” is based on mass unless otherwise specified. M represents a molar concentration (mol / l).

Example 1 (Synthesis of xanthene compound represented by Compound No. 4)
(Step 1-1)
In a 1000 ml four-necked flask, 8.1 parts of the compound represented by the above formula (2), 624 parts of methanol, and 4.3 parts of N-methylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) are placed, and the temperature is 30 ° C. for 20 hours. Stir. To this reaction solution was added 100 parts of 1M hydrochloric acid, and the mixture was concentrated under reduced pressure. Further, 500 parts of 1M hydrochloric acid was added, and the precipitated crystals were collected by filtration and washed with water to obtain 7.9 parts of a dye intermediate.

(Step 1-2)
In a 200 ml four-necked flask, 4.9 parts of the dye intermediate obtained in Step 1-1, 41 parts of N-methylpyrrolidone and 1.7 parts of thiosalicylic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) are placed, and 2 at 100 ° C. Stir for hours. The reaction solution was cooled to 90 ° C., 0.2 part of thiosalicylic acid was added, and the mixture was further stirred at 90 ° C. for 2.5 hours. The obtained reaction solution was dropped into 500 parts of water, and the precipitated crystals were filtered, washed with 200 parts of water, 21 parts of N-methylpyrrolidone and 50 parts of water, and dried to give compound No. Thus, 5.1 parts of the xanthene compound of the present invention represented by 4 was obtained. The maximum absorption wavelength of the xanthene compound was 522 nm (methanol).

Example 2 (Preparation of aqueous dye composition)
After mixing 10 mg of the xanthene compound obtained in Example 1 and 9990 mg of a 5% by mass aqueous sodium carbonate solution in a 25 ml sample tube, the mixture was vibrated at 25 ° C. for 3 minutes using an ultrasonic vibrator to give a xanthene compound concentration of 0. A 1% aqueous dye composition was prepared. In the obtained aqueous dye composition, no residue was observed visually. In addition, with respect to the aqueous dye composition prepared in the same manner as described above using 10 mg of xanthene compound and 990 mg of 5% by weight aqueous sodium carbonate solution, and 10 mg of xanthene compound and 90 mg of 5% by weight aqueous sodium carbonate solution, It was not confirmed.

Comparative Example 1
A comparative aqueous dye composition was prepared in the same manner as in Example 2 except that the xanthene compound obtained in Example 1 was changed to the xanthene compound represented by the above formula (100). In the obtained 0.1% comparative aqueous dye composition, no visual residue was confirmed, but in the 1% and 10% comparative aqueous dye compositions, a visual residual was confirmed. .

Comparative Example 2
A comparative aqueous dye composition was prepared in the same manner as in Example 2 except that the xanthene compound obtained in Example 1 was changed to a xanthene compound represented by the following formula (101). Visual differences were observed in all of the 0.1%, 1% and 10% comparative aqueous dye compositions obtained.

  From the examples and comparative examples, it is clear that the xanthene compound represented by the formula (1) of the present invention is excellent in solubility in an aqueous medium.

The xanthene compound of the present invention is excellent in sharpness and color developability, and the xanthene compound has high solubility in an aqueous medium and is easy to handle. Therefore, the xanthene compound of the present invention can be used for a dye-colored product, and can be used for a wide range of applications such as color filter inks and inkjet inks.

Claims (6)

Xanthene compound represented by formula (1)

(In Formula (1), R ¹ represents a hydrogen atom or an unsubstituted alkyl group having 1 to 8 carbon atoms. R ^{2 to} R ¹¹ are each independently a hydrogen atom; a carboxyl group; a halogen atom, a hydroxy group, and an alkoxy group. Represents an alkyl group having 1 to 4 carbon atoms or an unsubstituted alkyl group having 1 to 4 carbon atoms having a substituent selected from the group consisting of: and at least one of R ^{7 to} R ¹¹ is a carboxyl group. ). The xanthene compound according to claim 1, wherein R ¹ in formula (1) is an unsubstituted alkyl group having 1 to 4 carbon atoms, and one of R ^{7 to} R ¹¹ is a carboxyl group. An oil-based dye composition containing the xanthene compound according to claim 1 or 2 and an oil-soluble organic solvent. An aqueous dye composition comprising the xanthene compound according to claim 1 or 2 and an aqueous medium. A printed matter obtained using the oil-based dye composition according to claim 3 or the aqueous dye composition according to claim 4. The color filter obtained using the oil-based dye composition of Claim 3, or the water-based dye composition of Claim 4.