TW201311829A - Compound - Google Patents

Abstract

The present invention provides a compound of the formula (I). Wherein R1 and R2 each independently represent a hydrogen atom or an alkyl group, R3 represents -SO3H, -SO3-M+, -CO2H or -CO2-M+, M+ represents (R11)4N+, Na+ or K+, R11 represents a hydrogen atom, an alkyl group or an aralkyl group, R4 represents an alkyl group, an alkoxy group, a hydroxyl group, a cyano group or a nitro group, m represents an integer of from 0 to 2, n and p each independently represent an integer of from 0 to 2.

Description

Compound

The present invention relates to a compound which is useful as a dye.

The dye is used to display color by using reflected light or transmitted light, for example, in the fields of fiber materials, liquid crystal display devices, inkjet, and the like. As such a dye, for example, Rose Bengal B represented by the following formula (a) having a dibenzopyran skeleton is known (Hiroshi Hiroshi "New Dye Chemistry" 1st Edition, 274 pages, May 1973, Technology Report Hall )).

The above-mentioned compounds previously known do not necessarily sufficiently satisfy the solubility in an organic solvent.

The present invention includes the inventions described in the following [1] to [9].

[1] A compound represented by the formula (I), formula (I): [In the formula (I), R ¹ and R ² each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R ³ represents -SO ₃ H, -SO ₃ ^- M ⁺ , -CO ₂ H or -CO ₂ ^- M ⁺ ; M ⁺ represents (R ¹¹ ) ₄ N ⁺ , Na ⁺ or K ⁺ ; R ¹¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and 4 R groups ^{11 is the} same or different from each other; m represents an integer of 0 to 2; when m is 2, two R ³ are the same or different from each other; n and p each independently represent an integer of 0 to 2].

[2] A compound represented by the formula (I'), formula (I'): [In the formula (I'), R ¹ , R ² , R ³ , m, n and p each represent the same meaning as described above].

[3] The compound according to [1] or [2], wherein each of R ¹ and R ^{2 is} independently a hydrogen atom or a methyl group.

[4] The compound according to any one of [1] to [3] wherein R ³ is -SO ₃ H or -SO ₃ ^- M ⁺ .

[5] The compound according to any one of [1] to [4] wherein m is 0 or 1.

[6] The compound according to any one of [1] to [5] wherein n is 1.

[7] The compound according to any one of [1] to [6] wherein p is 1.

[8] A process for producing a compound represented by the formula (I') which comprises a step of reacting a compound represented by the formula (II) with a compound represented by the formula (III), [In the formula (II), R ¹ , R ² , R ³ and m each represent the same meaning as described above]

[In the formula (III), n and p each represent the same meaning as described above] [In the formula (I'), R ¹ , R ² , R ³ , m, n and p each represent the same meaning as described above].

[9] The production method according to [8], wherein the compound represented by the formula (II) and the compound represented by the formula (III) are reacted in the absence of a solvent.

The compound of the present invention is excellent in solubility in an organic solvent.

The compound of the present invention is a compound represented by the formula (I) (hereinafter sometimes referred to as "compound (I)"). Also included in the compounds of the invention are the tautomers thereof or salts thereof. Examples of the salt include an alkali metal salt such as a lithium salt, a potassium salt or a sodium salt.

Formula (I): [In the formula (I), R ¹ , R ² , R ³ , m, n and p each represent the same meaning as described above]

R ¹ and R ² are each independently a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and a hydrogen atom or a methyl group is preferred from the viewpoint of easy availability of the starting material, and more preferably a hydrogen atom. Examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a neopentyl group, and a hexyl group.

R ³ is -SO ₃ H, -SO ₃ ^- M ⁺ , -CO ₂ H or -CO ₂ ^- M ⁺ . Here, M ⁺ is ⁺ N(R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N(R ¹¹ ) ₄ . R ¹¹ is a hydrogen atom, or alkyl having 1 to 20 carbon atoms of the aralkyl group having 7 to 10, preferably ⁺ N (R ¹¹⁾ ₄ 4 of R ^11, at least two carbon atoms from 5 to 20 alkyl.

Examples of the alkyl group having 1 to 20 carbon atoms in R ¹¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group, a neopentyl group, and a hexyl group. Heptyl, octyl, 2-ethylhexyl, decyl, decyl, dodecyl, hexadecyl, eicosyl and the like.

Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ include a benzyl group, a phenylethyl group, and a phenylbutyl group.

m represents an integer from 0 to 2. Among them, m is preferably 0 or 1, more preferably 0, from the viewpoint of obtaining a raw material.

n represents an integer from 0 to 2. Among them, n is preferably 1 from the viewpoint of obtaining a raw material.

p represents an integer from 0 to 2. Among them, p is preferably 1 from the viewpoint of obtaining a raw material.

In the compound (I), a compound represented by the formula (I') (hereinafter sometimes referred to as "compound (I')") is preferred in terms of ease of production.

[In the formula (I'), R ¹ , R ² , R ³ , m, n and p each represent the same meaning as described above]

Examples of the compound (I') include a compound represented by the formula (I-1) to the formula (I-16). The compound represented by the formula (I-1), the formula (I-3), the formula (I-5) or the formula (I-7) is more preferred, and the compound represented by the formula (I-1) is more preferred.

Hereinafter, a method for producing the compound (I') in the compound (I) will be described.

The method of producing the compound (I') includes a compound represented by the formula (II) (hereinafter sometimes referred to as "compound (II)") and a compound represented by the formula (III) (hereinafter sometimes referred to as a compound). "Product (III)") a method of producing a reaction step, [In the formula (II), R ¹ , R ² , R ³ and m each represent the same meaning as described above] [In the formula (III), n and p each represent the same meaning as described above]

Although the reaction can also be carried out in the presence of a solvent, in terms of productivity, it is preferred to use no solvent in practice, that is, in the absence of a solvent. The reaction is usually carried out by mixing the compound (II) with the compound (III) and allowing the resulting mixture to be cooked under stirring. Here, the phrase "the solvent is not actually used" means that a sufficient amount of the solvent for dissolving the compound (II) and the compound (III) and providing a reaction site is not used. In the present case, it means that there is no sufficient amount of solvent for dissolving the compound (II) together with the compound (III) and providing a reaction site, and generally means a compound relative to the compound (II) and the compound. The total amount of use of (III) is less than 1% by mass, preferably less than 0.1% by mass.

Examples of the solvent include a hydrocarbon solvent such as toluene or xylene; a halogenated hydrocarbon solvent such as chlorobenzene, dichlorobenzene or chloroform; an alcohol solvent such as methanol, ethanol or butanol; and a nitrohydrocarbon such as nitrobenzene. a solvent; a ketone solvent such as methyl isobutyl ketone; a guanamine solvent such as 1-methyl-2-pyrrolidone;

The reaction temperature is preferably from 30 ° C to 180 ° C, more preferably from 80 ° C to 130 ° C. The reaction time is preferably from 1 hour to 12 hours, more preferably from 3 hours to 8 hours.

The amount of the compound (III) to be used is preferably 2 mol or more and 16 mol or less, more preferably 2 mol or more and 10 mol or less, based on 1 mol of the compound (II).

The method of obtaining the compound (I') which is a target compound from the reaction mixture is not particularly limited, and various known methods can be employed. For example, the reaction mixture may be mixed together with an acid such as acetic acid or the like, and the precipitated crystals may be collected by filtration. The above acid is preferably prepared by previously preparing an aqueous acid solution, and then adding the reaction mixture to the above aqueous solution. The temperature at the time of adding the reaction mixture is preferably 10° C. or higher and 50° C. or lower, more preferably 20° C. or higher and 50° C. or lower, and still more preferably 20° C. or higher and 30° C. or lower. Further, it is preferred to add the reaction mixture to an aqueous acid solution and then stir at the same temperature for about 0.5 to 2 hours. It is preferred to wash the crystals collected by washing with water or the like, followed by drying. Further, it may be further purified by a known method such as recrystallization as needed.

The compound of the present invention obtained in the above manner is useful as a dye. Further, since the compound of the present invention has high solubility in an organic solvent, it is particularly used as a color filter used in a display device such as a liquid crystal display device. It is more useful.

The dye used in the present invention is the compound (I) of the present invention as an active ingredient.

The coloring composition used in the present invention preferably contains a dye containing the compound (I) of the present invention as an active ingredient as a coloring agent (hereinafter sometimes referred to as "coloring agent (A)"), and further contains a resin (B). ). More preferably, the coloring composition further contains a polymerizable compound (C), a polymerization initiator (D), and a solvent (E).

In addition to the dye containing the compound (I) of the present invention as an active ingredient, the coloring agent (A) may further contain a pigment and/or a dye different from the dye containing the compound (I) of the present invention as an active ingredient.

A dye different from the dye having the compound (I) of the present invention as an active ingredient can be exemplified as a solvent in the Colour Index (published by The Society of Dyers and Colourists) (Solvent) ), Acid, Basic, Reactive, Direct, Disperse or Reduced (Vat) dyes. More specifically, the following dye index (C.I.) number of dyes may be mentioned, but it is not limited thereto.

CI Solvent Yellow 25, 79, 81, 82, 83, 89; CI Acid Yellow 7, 23, 25, 42, 65, 76; CI Reactive Yellow 2, 76, 116; CI Direct Yellow 4, 28, 44, 86 , 132; CI disperse yellow 54, 76; CI solvent orange 41, 54, 56, 99; CI acid orange 56, 74, 95, 108, 149, 162; CI Reactive Orange 16; CI Direct Orange 26; CI Solvent Red 24, 49, 90, 91, 118, 119, 122, 124, 125, 127, 130, 132, 160, 218; CI Acid Red 73, 91, 92 , 97, 138, 151, 211, 274, 289; CI acid purple 102; CI solvent green 1, 5; CI acid green 3, 5, 9, 25, 28; CI alkaline green 1; CI reduced green 1 and so on.

As the pigment, an organic pigment or an inorganic pigment which is usually used in a pigment dispersion resist can be mentioned. Examples of the inorganic pigment include a metal compound such as a metal oxide or a metal salt, and specific examples thereof include oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony. Or a composite metal oxide. Further, specific examples of the organic pigment and the inorganic pigment include a compound classified as a pigment in a Colour Index (published by the Dyes and Colorists' Society). More specifically, the following dye index (C.I.) number of pigments may be mentioned, but it is not limited thereto.

CI Pigment Yellow 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173 and 180; CI Pigment oranges 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 215, 216, 224, 242, 254, 255 and 264; CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38; CI Pigment Green 7, 10, 15, 25, 36, 47 and 58 and the like.

The content of the colorant (A) is preferably from 5 to 60% by mass based on the solid content of the coloring composition. Here, the solid content component means the total of the components other than the solvent in the coloring composition.

The content of the dye containing the compound (I) of the present invention as an active ingredient contained in the colorant (A) is preferably from 3 to 100% by mass.

The dye and the pigment different from the dye containing the compound (I) of the present invention as an active ingredient may be used alone or in combination of two or more kinds thereof together with the dye containing the compound (I) of the present invention as an active ingredient.

The resin (B) is not particularly limited, and any resin can be used.

The resin (B) is preferably an alkali-soluble resin, more preferably a resin containing a structural unit derived from (meth)acrylic acid. Here, (meth)acrylic acid means acrylic acid and/or methacrylic acid.

Specific examples of the resin (B) include methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, and methacrylic acid/benzyl methacrylate/ Methacrylic acid Ester copolymer, methacrylic acid/styrene/benzyl methacrylate/N-phenyl maleimide copolymer, methacrylic acid/styrene/glycidyl methacrylate copolymer, and the like.

The polystyrene-equivalent weight average molecular weight of the resin (B) is preferably 5,000~ 35,000, more preferably 6,000~30,000.

The acid value of the resin (B) is preferably from 50 to 150 mgKOH/g, more preferably from 60 to 135 mgKOH/g.

The content of the resin (B) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, based on the solid content of the coloring composition.

The polymerizable compound (C) is not particularly limited as long as it is a compound which can be polymerized by an active radical, an acid or the like generated by the polymerization initiator (D). For example, a compound having a polymerizable ethylenically unsaturated bond or the like can be given.

The polymerizable compound (C) is preferably a photopolymerizable compound having three or more polymerizable groups. Examples of the photopolymerizable compound having three or more polymerizable groups include pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethyl acrylate, dipentaerythritol hexaacrylate, and the like. Dipentaerythritol hexamethacrylate or the like. The above polymerizable compound (C) may be used singly or in combination of two or more.

The content of the polymerizable compound (C) is preferably 5 to 65% by mass, and more preferably 10 to 60% by mass based on the solid content of the coloring composition.

Examples of the polymerization initiator (D) include a living radical generator, an acid generator, and the like. The living radical generating agent generates active radicals by the action of heat or light. Examples of the living radical generating agent include an alkylphenone compound, a thioxanthone compound, and three Compounds, hydrazine compounds, and the like.

As the above alkylphenone compound, for example, 2-methyl-2- Lolinyl-1-(4-methylthiophenyl)-1-propanone, 2-hydroxy-2-methyl-1-phenyl-1-propanone, benzoindimethyl ketal, 2-hydroxyl -2-methyl-1-[4-(2-hydroxyethoxy)phenyl]-1-propanone, 1-hydroxycyclohexyl phenyl ketone, and the like.

Examples of the above thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthiaxanone, and 2,4-dichloro. Xanthone, 1-chloro-4-propoxythiaxanone, and the like.

As the above three The compound may, for example, be 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-tri , 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-three 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)vinyl]-1,3,5-three , 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-three Wait.

The ruthenium compound may, for example, be an O-indenyl ruthenium compound, and specific examples thereof include N-benzylideneoxy-1-(4-phenylthiophenyl)-1-butanone-2 -imine, N-benzylideneoxy-1-(4-phenylthiophenyl)-1-octanone-2-imine, N-acetoxy-1-[9-ethyl- 6-(2-Methylbenzylidene)-9H-indazol-3-yl]ethane-1-imine, N-ethyloxy-1-[9-ethyl-6-{2- Methyl-4-(3,3-dimethyl-2,4-dioxolanylmethoxy)benzylidenyl}-9H-indazol-3-yl]ethane-1-imine Wait.

Further, as the living radical generating agent, for example, 2,4,6-trimethylbenzimidyldiphenylphosphine oxide or 2,2'-bis(o-chlorophenyl)-4,4' may be used. 5,5'-tetraphenyl-1,2'-biimidazole, 10-butyl-2-chloroacridone, 2-ethylhydrazine, benzene Even oxime, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanium titanate compound, and the like.

Examples of the acid generator include 4-hydroxyphenyldimethylhydrazine p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, and 4-ethenyloxyphenyldimethylate. Base p-toluenesulfonate, 4-acetoxyphenyl-methyl-benzyl hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, An onium salt such as phenylhydrazine p-toluenesulfonate or diphenylphosphonium hexafluoroantimonate; or a nitrobenzyl tosylate or a benzoin tosylate.

The above polymerization initiator (D) may be used singly or in combination of two or more.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the total of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator is within the above range, high sensitivity is obtained, and the exposure time is shortened, and productivity is improved, which is preferable.

Examples of the solvent (E) include an ether solvent, an aromatic hydrocarbon solvent, a ketone solvent, an alcohol solvent, an ester solvent, and a guanamine solvent.

Examples of the ether solvent include tetrahydrofuran, tetrahydropyran, and 1,4-two. Alkane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl Ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate , propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol single Butyl ether acetate and the like.

Examples of the aromatic hydrocarbon-based solvent include benzene, toluene, xylene, and mesitylene.

Examples of the ketone solvent include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, and 4-hydroxy-4-methyl. -2-pentanone, cyclopentanone, cyclohexanone, and the like.

Examples of the alcohol-based solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.

Examples of the ester solvent include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, and butyl. Ethyl acetate, butyl butyrate, alkyl ester, methyl lactate, ethyl lactate, butyl lactate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethoxyacetic acid Methyl ester, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, Methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, Methyl 2-methoxy-2-methylpropanoate, ethyl 2-ethoxy-2-methylpropionate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetate Ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, γ-butyrolactone, and the like.

Examples of the guanamine-based solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

These solvents may be used singly or in combination of two or more.

The content of the solvent (E) in the coloring composition is preferably from 70 to 95% by mass, more preferably from 75 to 90% by mass, based on the coloring composition.

The coloring composition may optionally contain various additives such as a surfactant, a filler, another polymer compound, an adhesion promoter, an antioxidant, an ultraviolet absorber, a light stabilizer, and a chain transfer agent.

The compound (I) of the present invention is useful as a dye. Since the molar absorption coefficient is high and exhibits high solubility to an organic solvent, it is particularly useful as a dye used in a color filter of a display device such as a liquid crystal display device.

Further, the coloring composition containing the compound (I) of the present invention can be used for a display device including a color filter as a part of its constituent parts in a known manner (for example, a known liquid crystal display device, organic EL (Electro Luminescence) Various devices related to colored images, such as solid-state imaging devices, such as electroluminescence devices.

Example

Hereinafter, the present invention will be more specifically described by way of examples. In the examples, the % or the part of the content or the amount used is a mass basis unless otherwise specified.

In the following examples, the structure of the compound was confirmed by mass analysis (LC: Model 1200 manufactured by Agilent; MASS: LC/MSD type manufactured by Agilent).

[Example 1]

15.0 parts of the compound represented by the following formula (II-1), 75.0 parts of N-methyl-2-pyrrolidone, and 25.8 parts of decahydroquinoline (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed. The resulting mixture was stirred at 110 ° C for 24 hours. After cooling the reaction solution to room temperature, it was added to a mixed liquid of 600 parts of water and 100 parts of 35% hydrochloric acid, and the mixture was stirred at room temperature for 1 hour. The precipitated crystals were obtained as a residue obtained by suction filtration, and then dried to obtain 19.5 parts of the compound represented by the formula (I-1). The yield was 86%.

Identification of compounds represented by formula (I-1)

(mass analysis) ionization mode = ESI +: m / z = [M + H] ⁺ 611.4

Accurate quality: 610.3

<Measurement of Solubility>

The solubility of the compound obtained in Example 1 and Rose Bengal B (manufactured by Tokyo Chemical Industry Co., Ltd.) in propylene glycol monomethyl ether (hereinafter abbreviated as PGME) and ethyl lactate (hereinafter abbreviated as EL) was determined in the following manner.

The compound was mixed with the above solvent in a 50 mL sample tube, and then the sample tube was stoppered and shaken at 30 ° C for 3 minutes using an ultrasonic vibration machine. Then, after standing at room temperature for 30 minutes, suction filtration was carried out, and the residue was visually observed. When it is not possible to confirm the insoluble matter, it is judged that the solubility is good and is marked with ○ in Table 1, and when the insoluble matter is confirmed, it is judged. Poor solubility and marked X in Table 1.

2% compound 0.02 g, solvent 1 g

Compound (a) is Rose Red B (manufactured by Tokyo Chemical Industry Co., Ltd.).

[Embodiment 2] <Preparation of coloring composition>

The following ingredients were mixed to obtain a coloring composition:

[Production of color filter]

The colored composition obtained above was applied to the glass by a spin coating method to volatilize the volatile component. After cooling, light irradiation was performed using a patterned quartz glass mask and an exposure machine.

After light irradiation, development was carried out with an aqueous solution of potassium hydroxide and heated in an oven. A color filter was obtained up to 200 °C.

From the above results, it is understood that the compound of the present invention exhibits a high solubility to an organic solvent. Further, when a coloring composition containing the compound is used, impurities are less likely to be produced, and a high-quality color filter can be produced.

The compound of the present invention is excellent in solubility in an organic solvent.

Claims (9)

A compound of the formula (I), which is represented by the formula (I): [In the formula (I), R ¹ and R ² each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R ³ represents -SO ₃ H, -SO ₃ ^- M ⁺ , -CO ₂ H or -CO ₂ ^- M ⁺ ; M ⁺ represents (R ¹¹ ) ₄ N ⁺ , Na ⁺ or K ⁺ ; R ¹¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and 4 R groups ^{11 is the} same or different from each other; m represents an integer of 0 to 2; when m is 2, two R ³ are the same or different from each other; n and p each independently represent an integer of 0 to 2]. A compound of the formula (I'), of the formula (I'): [In the formula (I'), R ¹ and R ² each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R ³ represents -SO ₃ H, -SO ₃ ^- M ⁺ , -CO ₂ H or - CO ₂ ^- M ⁺ ; M ⁺ represents (R ¹¹ ) ₄ N ⁺ , Na ⁺ or K ⁺ ; R ¹¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, 4 R ^{11 is the} same or different from each other; m represents an integer of 0 to 2; when m is 2, two R ³ are the same or different from each other; n and p each independently represent an integer of 0 to 2]. The compound of claim 1 or 2, wherein R ¹ and R ² are each independently a hydrogen atom or a methyl group. The compound of any one of claims 1 to 3, wherein R ³ is -SO ₃ H or -SO ₃ ^- M ⁺ . The compound of any one of claims 1 to 4, wherein m is 0 or 1. The compound of any one of claims 1 to 5, wherein n is 1. The compound of any one of claims 1 to 6, wherein p is 1. A process for producing a compound represented by the formula (I'), which comprises the step of reacting a compound represented by the formula (II) with a compound represented by the formula (III), [In the formula (II), R ¹ and R ² each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and R ³ represents -SO ₃ H, -SO ₃ ^- M ⁺ , -CO ₂ H or -CO ₂ ^- M ⁺ ; M ⁺ represents (R ¹¹ ) ₄ N ⁺ , Na ⁺ or K ⁺ ; R ¹¹ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and 4 R groups ¹¹ are the same or different from each other; m represents an integer of 0 to 2; when m is 2, two R ³ are the same or different from each other] [In the formula (III), n and p each independently represent an integer of 0 to 2] [In the formula (I'), R ¹ , R ² , R ³ , m, n and p each represent the same meaning as described above]. The process of claim 8, wherein the compound represented by the formula (II) is reacted with the compound represented by the formula (III) in the absence of a solvent.