WO2014002335A1 - Colorant xanthène pour un filtre coloré et filtre coloré utilisant ledit colorant - Google Patents

Colorant xanthène pour un filtre coloré et filtre coloré utilisant ledit colorant Download PDF

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Publication number
WO2014002335A1
WO2014002335A1 PCT/JP2013/001707 JP2013001707W WO2014002335A1 WO 2014002335 A1 WO2014002335 A1 WO 2014002335A1 JP 2013001707 W JP2013001707 W JP 2013001707W WO 2014002335 A1 WO2014002335 A1 WO 2014002335A1
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WO
WIPO (PCT)
Prior art keywords
group
carbon atoms
xanthene dye
substituent
linear
Prior art date
Application number
PCT/JP2013/001707
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English (en)
Japanese (ja)
Inventor
良和 服部
山田　英祐
泰斗 村岡
規敏 鈴木
Original Assignee
保土谷化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 保土谷化学工業株式会社 filed Critical 保土谷化学工業株式会社
Priority to KR1020147037111A priority Critical patent/KR102021637B1/ko
Priority to CN201380034232.2A priority patent/CN104412134B/zh
Priority to JP2014522372A priority patent/JP6246120B2/ja
Publication of WO2014002335A1 publication Critical patent/WO2014002335A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a color filter dye and a color filter using the dye, and more particularly to a red dye having high heat resistance and excellent solubility in an organic solvent, and a color filter using the dye.
  • Color filters may be used for liquid crystal and electroluminescence (EL) display devices.
  • a color filter is manufactured by laminating a colored layer on a light-transmitting substrate such as glass by a dyeing method, a pigment dispersion method, a printing method, an electrodeposition method, or the like.
  • the materials used for the colored layer are roughly classified into pigments and dyes, and pigments that are generally excellent in heat resistance and light resistance are widely used (for example, Patent Documents 1 and 2).
  • Patent Documents 1 and 2 it is known that a color filter using a pigment has a depolarizing effect, so that the display contrast ratio of the color liquid crystal display device is deteriorated.
  • pigments are generally insoluble in a solvent, it is necessary to form fine particles and disperse them in a dispersion liquid such as a resin. It was.
  • Measures for solving these problems include a method of using a dye in addition to a pigment as a colorant. Since the dye is soluble in the solvent, the color filter combined with the dye has an excellent spectral characteristic as compared with the case where only the pigment is used as the colorant and has a depolarizing effect.
  • dyes used for color filters xanthene dyes (for example, see Patent Documents 3 to 5) are known from the viewpoint of excellent color developability and heat resistance, and are represented by the following structural formula (I).
  • C.I. I Means a color index.
  • the present invention has been made to solve the above-mentioned problems, and has excellent heat resistance and good solubility in organic solvents such as propylene glycol monomethyl ether (PGME) which is generally used in the production of color filters.
  • An object of the present invention is to provide a xanthene dye having both of the above and a method of using it as a colorant for a red color filter.
  • the present inventors have improved the solubility of an anion having a sulfonate group and an ammonium ion in an organic solvent such as PGME while maintaining heat resistance.
  • the present invention has been completed.
  • the present invention has been obtained as a result of earnest research to achieve the above-mentioned object, and has the following gist.
  • a xanthene dye for a colorant of a red color filter represented by the following general formula (1).
  • R 1 to R 5 and R 11 to R 15 may be the same or different, and may be a hydrogen atom, a hydroxyl group, a sulfonate group, a linear group having 1 to 10 carbon atoms which may have a substituent or A branched alkyl group, an optionally substituted cycloalkyl group having 3 to 10 carbon atoms, an optionally substituted linear or branched alkoxy group having 1 to 10 carbon atoms And a cycloalkoxy group having 3 to 10 carbon atoms which may have a substituent.
  • any one of R 1 to R 5 and any one of R 11 to R 15 are sulfonate groups.
  • R 6 to R 10 may be the same or different and each has a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or a substituent.
  • An optionally substituted cycloalkyl group having 3 to 10 carbon atoms, an optionally substituted linear or branched alkoxy group having 1 to 10 carbon atoms, and an optionally substituted carbon representss a cycloalkoxy group having 3 to 10 atoms.
  • R 1 to R 15 may be bonded to each other through a single bond between adjacent groups to form a ring.
  • R 16 to R 19 represent a hydrogen atom or a linear or branched alkyl group having 1 to 20 carbon atoms which may have a substituent.
  • M represents an alkali metal atom
  • n represents 1 or 2.
  • any one of R 1 to R 5 and any one of R 11 to R 15 is a sulfonate group, and the remaining R 1 to R 5 and R 11 to R 15 are each a hydrogen atom or a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or a carbon atom having 3 to 3 carbon atoms which may have a substituent.
  • 1. a group selected from 10 cycloalkyl groups; The xanthene dye described in 1.
  • R 11 is a sulfonate group.
  • R 16 to R 19 may be a linear or branched group having 4 to 20 carbon atoms which may have a substituent. Wherein the alkyl group is 1. The xanthene dye described in 1.
  • R 16 and R 17 are hydrogen atoms.
  • n is 1.
  • the xanthene dye of the present invention has high heat resistance and is excellent in solubility in an organic solvent such as PGME, and thus is useful as a colorant used for a red color filter.
  • An optionally substituted linear or branched alkyl group having 1 to 10 carbon atoms represented by R 1 to R 15 in the general formula (1), “having a substituent.
  • An optionally substituted cycloalkyl group having 3 to 10 carbon atoms “ an optionally substituted linear or branched alkoxy group having 1 to 10 carbon atoms ”or“ having a substituent.
  • a “C1-C10 linear or branched alkyl group”, “C3-C10 cycloalkyl group” in the “C3-C10 cycloalkoxy group” which may be Specific examples of the “linear or branched alkoxy group having 1 to 10 carbon atoms” or “cycloalkoxy group having 3 to 10 carbon atoms” include a methyl group, an ethyl group, a propyl group, a butyl group, and pentyl.
  • the “substituent” in the “optionally substituted cycloalkoxy group having 3 to 10 carbon atoms” includes a halogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms, and 3 to 10 carbon atoms.
  • halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; direct methyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, etc.
  • R 1 to R 5 and R 11 to R 15 in the general formula (1) are each a linear or branched alkyl having 1 to 10 carbon atoms which may have a hydrogen atom, a sulfonate group, or a substituent. It is preferably a linear or branched alkoxy group having 1 to 10 carbon atoms which may have a group or a substituent. However, any one of R 1 to R 5 and any one of R 11 to R 15 are sulfonate groups.
  • R 6 to R 10 in the general formula (1) have a hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms which may have a substituent, or a substituent. It is preferably a linear or branched alkoxy group having 1 to 10 carbon atoms.
  • Specific examples of the 1 to 20 linear or branched alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, Examples thereof include linear alkyl groups such as dodecyl group and tridecyl group; branched alkyl groups such as isopropyl group, isobutyl group, sec-butyl group, tert-butyl group and isooctyl group.
  • substituted linear or branched alkyl group having 1 to 20 carbon atoms represented by R 16 to R 19 in the general formula (1) Is a hydroxyl group, a halogen atom, a linear or branched alkoxy group having 1 to 10 carbon atoms, a cycloalkoxy group having 3 to 10 carbon atoms; a substituted or unsubstituted aromatic carbon atom having 6 to 20 carbon atoms Examples thereof include a hydrogen group and a condensed polycyclic aromatic group.
  • hydroxyl group halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group
  • Linear alkoxy groups such as nonyloxy group and decyloxy group; branched alkoxy groups such as isopropoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group and isooctyloxy group
  • cyclopropoxy group, cyclopentyloxy group examples include cycloalkoxy groups such as cyclohexyloxy group and cyclopropylmethyloxy group; aromatic hydrocarbon groups such as phenyl group, methoxyphenyl group, naphthyl group, biphenyl group and anthracenyl group, or condensed polycyclic aromatic groups. .
  • At least one of R 16 to R 19 may have a substituent from the viewpoint of solubility in a nonpolar organic solvent such as a hydrocarbon solvent. It is preferably 20 to 20 linear or branched alkyl groups.
  • alkali metal represented by M in the general formula (1) sodium or potassium is preferable, and sodium is particularly preferable.
  • N in the general formula (1) is 1 or 2, but 1 is more preferable.
  • the xanthene dye of the present invention when used as a colorant for a red color filter, it can be used in combination with a known red pigment.
  • the red pigment is not limited as long as it is a known pigment. I. Pigment red 177, C.I. I. Pigment red 209, C.I. I. Pigment red 242, C.I. I. Pigment red 254 and the like.
  • the xanthene dye represented by the general formula (1) can be synthesized by a known method such as counter ion exchange. Specifically, it can be synthesized by adding an aqueous solution of a salt composed of an amine compound and an acid to an aqueous solution of a dye whose sulfonate group is an alkali metal salt.
  • an organic solvent may be mixed in order to eliminate or alleviate it.
  • the organic solvent is not particularly limited as long as the corresponding xanthene dye has sufficient solubility, and is an aromatic hydrocarbon such as toluene and xylene; acetone, 2-butanone, 2-pentanone, 3-pentanone, etc. Ketones; esters such as ethyl acetate and butyl acetate; alcohols such as methanol, ethanol, propanol, isopropanol, butanol, pentanol, and hexanol.
  • Specific examples of preferred compounds as anions or ammonium ions in the xanthene dye of the present invention represented by the general formula (1) are the following (A-1) to (A-17) or (B-1) to (B- As shown in 20), the present invention is not limited to these compounds.
  • the xanthene dye of the present invention is excellent in solubility in an organic solvent, particularly in PGME.
  • the solubility in PGME is preferably 2% by weight or more, more preferably 5% by weight or more. It is particularly preferably 10% by weight or more.
  • the higher the solubility the better.
  • the xanthene dye (C-1) of the examples of the present invention has high solubility in PGME while maintaining the same heat resistance as that of the comparative compound (CI Acid Red 289). It can be seen that it is useful as a color filter dye.
  • the xanthene dye according to the present invention is excellent in heat resistance and solubility in an organic solvent (such as PGME), and is useful as a color filter dye.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Optical Filters (AREA)

Abstract

L'invention a pour but de proposer : un colorant xanthène pour un filtre coloré, qui a une excellente solubilité dans un solvant organique et une résistance élevée à la chaleur ; et un filtre coloré obtenu à l'aide du colorant. A cet effet, selon l'invention, un filtre coloré est constitué à l'aide d'un colorant xanthène pour un agent de coloration pour un filtre coloré rouge, le colorant xanthène étant représenté par la formule générale (1).
PCT/JP2013/001707 2012-06-26 2013-03-14 Colorant xanthène pour un filtre coloré et filtre coloré utilisant ledit colorant WO2014002335A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020147037111A KR102021637B1 (ko) 2012-06-26 2013-03-14 컬러 필터용 크산텐계 색소 및 상기 색소를 이용한 컬러 필터
CN201380034232.2A CN104412134B (zh) 2012-06-26 2013-03-14 滤色器用呫吨系色素以及使用了该色素的滤色器
JP2014522372A JP6246120B2 (ja) 2012-06-26 2013-03-14 カラーフィルター用キサンテン系色素並びに該色素を用いたカラーフィルター

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201261664397P 2012-06-26 2012-06-26
US61/664,397 2012-06-26

Publications (1)

Publication Number Publication Date
WO2014002335A1 true WO2014002335A1 (fr) 2014-01-03

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PCT/JP2013/001707 WO2014002335A1 (fr) 2012-06-26 2013-03-14 Colorant xanthène pour un filtre coloré et filtre coloré utilisant ledit colorant

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JP (1) JP6246120B2 (fr)
KR (1) KR102021637B1 (fr)
CN (1) CN104412134B (fr)
TW (1) TWI623591B (fr)
WO (1) WO2014002335A1 (fr)

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WO2015105108A1 (fr) * 2014-01-10 2015-07-16 富士フイルム株式会社 Composé, composition colorante, encre d'impression par jet d'encre, procédé d'impression par jet d'encre, cartouche d'imprimante à jet d'encre, matériau imprimé par jet d'encre, filtre de couleur, encre en poudre de couleur et encre de transfert
TWI793217B (zh) * 2017-12-11 2023-02-21 日商保土谷化學工業股份有限公司 黃色系化合物、含有該化合物之著色組合物、彩色濾光片用著色劑及彩色濾光片

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JP7198767B2 (ja) * 2017-10-24 2023-01-04 保土谷化学工業株式会社 キサンテン系カチオン染料と、有機アニオンとからなる造塩化合物を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター
JP7536496B2 (ja) * 2019-06-10 2024-08-20 保土谷化学工業株式会社 キサンテン系色素、該色素を含有する着色組成物、カラーフィルター用着色剤およびカラーフィルター

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TWI793217B (zh) * 2017-12-11 2023-02-21 日商保土谷化學工業股份有限公司 黃色系化合物、含有該化合物之著色組合物、彩色濾光片用著色劑及彩色濾光片

Also Published As

Publication number Publication date
JP6246120B2 (ja) 2017-12-13
CN104412134B (zh) 2018-01-30
TWI623591B (zh) 2018-05-11
TW201406868A (zh) 2014-02-16
CN104412134A (zh) 2015-03-11
JPWO2014002335A1 (ja) 2016-05-30
KR20150035820A (ko) 2015-04-07
KR102021637B1 (ko) 2019-10-18

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