JP-7854786-B2 - Xanthene pigment, coloring composition containing the pigment, coloring agent for color filters, and color filters

Inventors

• 山縣 直哉
• 神田 大三

Assignees

• 保土谷化学工業株式会社

Dates

Publication Date

20260507

Application Date

20210726

Priority Date

20200929

Claims (7)

1. Xanthene pigments represented by the following general formula (1). [In formula (1), Xn 1 and Xn 2 each independently represent a group represented by the following general formula (2), Ar is a group represented by the following general formula (3): An represents an anion, a represents an integer from 1 to 3, and b represents an integer from 0 to 6. When b is 2 or greater, multiple Ans may be the same or different. [In formula (2), R1 to R4 are each independently a hydrogen atom, Linear or branched alkyl groups having 1 to 30 carbon atoms, which may have substituents. Alternatively, it represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have substituents. R5 and R6 are, independently, a hydrogen atom, a halogen atom, Linear or branched alkyl groups having 1 to 30 carbon atoms, which may have substituents. Alternatively, it represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have substituents. R1 to R6 may be bonded to each other by adjacent groups to form a ring. The wavy line indicates the connection point with Ar. [In formula (3), Ar1 and Ar2 are indolyl groups having 8 to 30 carbon atoms , which may have substituents . L is a linking group, and represents a group consisting of at least one selected from the group consisting of -O-, -S-, linear or branched alkanediyl groups having 1 to 30 carbon atoms which may have substituents, and aromatic hydrocarbon groups having 6 to 30 carbon atoms which may have substituents. The wavy line represents the bond with the base represented by the general formula (2) above.
2. Xanthene pigments represented by the following general formula (1). [In formula (1), Xn 1 and Xn 2 each independently represent a group represented by the following general formula (2), Ar is a group represented by the following general formula (3): An represents an anion, a represents an integer from 1 to 3, and b represents an integer from 0 to 6. When b is 2 or greater, multiple Ans may be the same or different. [In formula (2), R1 to R4 are each independently a hydrogen atom, Linear or branched alkyl groups having 1 to 30 carbon atoms, which may have substituents. Alternatively, it represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have substituents. R5 and R6 are, independently, a hydrogen atom, a halogen atom, Linear or branched alkyl groups having 1 to 30 carbon atoms, which may have substituents. Alternatively, it represents an aromatic hydrocarbon group having 6 to 30 carbon atoms, which may have substituents. R1 to R6 may be bonded to each other by adjacent groups to form a ring. The wavy line indicates the connection point with Ar. [In formula (3), Ar1 and Ar2 are indolyl groups having 8 to 30 carbon atoms , which may have substituents . L is a linking group, selected from the group consisting of -O-, -S-, linear or branched alkanediyl groups having 1 to 30 carbon atoms (which may have substituents), and aromatic hydrocarbon groups having 6 to 30 carbon atoms (which may have substituents), or —O— represents a group that is a combination of two or more selected from the group consisting of linear or branched alkanediyl groups having 1 to 30 carbon atoms, which may have substituents, and aromatic hydrocarbon groups having 6 to 30 carbon atoms, which may have substituents. The wavy line represents the bond with the base represented by the general formula (2) above.
3. In the above general formula (1), An is a halide ion, (CF 3 SO 2 ) 2 N - The xanthene dye according to claim 1 or claim 2, which is at least one selected from the group consisting of sulfonylimide anions and sulfonate anions.
4. The concentration of the xanthene dye is 0.005 to 0.02 mmol/L. Using a propylene glycol monomethyl ether (PGME) solution, Measure at 23-27°C. In the wavelength range of 350 to 750 nm In an ultraviolet-visible transmission spectrum where the transmittance at the maximum absorption wavelength is 5%, For the range where the transmittance at wavelengths longer than the maximum absorption wavelength is between 90% and 97%, The regression coefficient S of the regression line calculated using the least squares method. a The value is 0.7 or higher. The xanthene pigment according to any one of claims 1 to 3.
5. A coloring composition containing a xanthene pigment according to any one of claims 1 to 4.
6. A coloring agent for color filters containing the coloring composition described in claim 5.
7. A color filter using the coloring agent for color filters described in claim 6.

Description

This invention relates to xanthene pigments, coloring compositions containing the pigments, colorants for color filters containing the pigments or coloring compositions, and color filters using the colorants. Pigments are broadly classified into natural pigments and synthetic pigments, with synthetic pigments further subdivided into inorganic pigments and organic pigments. Organic pigments are further subdivided into dyes (or synthetic dyes), organic pigments, and lakes (lake pigments, or lake dyes). Since the discovery of mauve in 1856, dyes have been extensively studied and are classified according to their dyeing properties into direct dyes, acid dyes, basic dyes, etc. They are also classified by their chemical structure, such as azo dyes, anthraquinone dyes, triphenylmethane dyes, and xanthene dyes. These dyes generally possess beautiful colors and are used in the formulation and coloring of resins, paints, pigments, printing inks, cosmetics, etc. (Non-patent documents 1, 2, etc.). Color filters are used in liquid crystal and electroluminescent (EL) display devices, as well as in CCD and CMOS image sensors. They are manufactured by laminating colored layers, such as thin dye films or dye-resin composite films, onto translucent substrates such as glass or transparent resin using dyeing, pigment dispersion, printing, or electrodeposition methods. Xanthene dyes, represented by formulas (B-1) to (B-3) below, are compounds used as colorants in color filters due to their vividness (see Patent Documents 1-3, etc.). For example, by using xanthene dyes such as C.I. Acid Red 289 (formula (B-1)) and C.I. Acid Red 52 (formula (B-2)) (C.I. is an abbreviation for color index) in combination with azopyridone dyes, excellent red tones can be obtained (Patent Document 1). Japanese Patent Publication No. 2002-265834Japanese Patent Publication No. 2012-207224Japanese Patent Publication No. 2018-076403Japanese Patent Publication No. 2013-57052 Hiroshi Horiguchi, "Advanced Theory of Synthetic Dyes," Sankyo Publishing Co., Ltd., July 15, 1969, p. 1-3The Society of Synthetic Organic Chemistry, ed., "New Edition: Handbook of Dyes," Maruzen Co., Ltd., July 20, 1970 (Showa 45), pp. 8-13."Chemical Communications," (UK), 2017, Vol. 53, pp. 1064–1067, Supporting Information This figure illustrates a specific example of the ultraviolet-visible transmission spectrum of the xanthene dye of the present invention. Embodiments of the present invention will be described in detail below. However, the present invention is not limited to the following embodiments and can be implemented in various ways within the scope of its gist. The xanthene pigment of the present invention is represented by the following general formula (1). In general formula (1), the "aromatic hydrocarbon group having 6 to 60 carbon atoms, which may have substituents" represented by Ar, includes aryl groups and condensed polycyclic aromatic groups. Specific examples of "aromatic hydrocarbon groups having 6 to 60 carbon atoms" include phenyl, biphenylyl, terphenylyl, naphthyl, anthryl, phenanthryl, fluorenyl, indenyl, pyrenyl, perilenyl, fluoranthenyl, and triphenylenyl groups. In general formula (1), the "heterocyclic group" in the "aromatic heterocyclic group having 1 to 60 carbon atoms that may have substituents" represented by Ar includes fused polycyclic aromatic heterocyclic groups, and specifically, the "heterocyclic group having 1 to 60 carbon atoms" is: Pyridyl group, pyrimidinyl group, quinolyl group, isoquinolyl group, pyrazinyl group, triazinyl group, naphthilidinyl group, acridinyl group, phenanthrolinyl group, carbolinyl group, prinyl group, indolidinyl group, naphthilidinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, synnolinyl group, pteridinyl group, phenanthridinyl group, perimidinyl group, antilydinyl group, Pyrrolyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, dihydropyrrolopyrrolyl group, indolyl group, isoindolyl group, indollidinyl group, indazolyl group, benzimidazolyl group, benzotriazolyl group, azaindolyl group, azaindazolyl group, pyrazolopyrimidinyl group, prinyl group, adenyl group, guanidinyl group, acridinyl group, phenadinyl group, Furanyl group, thiophenyl group, benzofuranyl group, isobenzofuranyl group, benzothienyl group, isobenzothiophenyl group, dibenzofuranyl group, dibenzothienyl group, Oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, phlopyrrolyl group, thienopyrrolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, benzoisothiazolyl group, benzothiadiazolyl group, phenoxathiinyl group, Examples include heterocyclic groups such as the benzo[1,2-b:4,5-b']dithiophenyl group and the bipyridinyl group. In general formula (1), the "substituents" in the "aromatic hydrocarbon group having 6 to 60 carbon atoms that may have substituents" or the "heterocyclic group having 1 to 60 carbon atoms that may