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WO2014050998A1 - Composition de coloration, composition de coloration photosensible, filtre coloré, procédé de fabrication de filtre coloré, élément d'imagerie à l'état solide et dispositif d'affichage d'image - Google Patents

Composition de coloration, composition de coloration photosensible, filtre coloré, procédé de fabrication de filtre coloré, élément d'imagerie à l'état solide et dispositif d'affichage d'image Download PDF

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Publication number
WO2014050998A1
WO2014050998A1 PCT/JP2013/076130 JP2013076130W WO2014050998A1 WO 2014050998 A1 WO2014050998 A1 WO 2014050998A1 JP 2013076130 W JP2013076130 W JP 2013076130W WO 2014050998 A1 WO2014050998 A1 WO 2014050998A1
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Prior art keywords
group
substituent
compound
ring
general formula
Prior art date
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PCT/JP2013/076130
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English (en)
Japanese (ja)
Inventor
一真 両角
新居 一巳
藤田 明徳
崇一郎 長田
佐々木 大輔
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Fujifilm Corp
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Fujifilm Corp
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Publication of WO2014050998A1 publication Critical patent/WO2014050998A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0675Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having oxygen or sulfur linked directly to the skeleton
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0671Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having halogen atoms linked directly to the Pc skeleton
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0676Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having nitrogen atom(s) linked directly to the skeleton
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00Porphines; Azaporphines
    • C09B47/04Phthalocyanines abbreviation: Pc
    • C09B47/06Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0678Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having-COOH or -SO3H radicals or derivatives thereof directly linked to the skeleton
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007Filters, e.g. additive colour filters; Components for display devices
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/09Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • HELECTRICITY
    • H05ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05BELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00Electroluminescent light sources
    • H05B33/10Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • GPHYSICS
    • G02OPTICS
    • G02BOPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00Optical elements other than lenses
    • G02B5/20Filters
    • G02B5/22Absorbing filters

Definitions

  • coloring compositions containing dyes are useful for use, in coloring compositions containing phthalocyanine compounds as dyes, solubility of dyes, etc., color density and hue stability against light and heat (light resistance, heat resistance) ) And spectral characteristics (for example, a hue suitable for a color filter, color purity, etc.) have not yet been satisfied.
  • R 4 is a hydrogen atom, an alkyl group which may have a substituent, an oxyalkylene group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • the alkylarylamino group which may have is represented.
  • alkoxy group which may have a substituent in the general formulas (2) to (6) are shown below.
  • Examples of the alkoxy group which may have a substituent include a methoxy group, an ethoxy group, a 1-butoxy group, a 2-butoxy group, a propoxy group, an isopropoxy group, a t-butoxy group, a dodecyloxy group, and a cyclo
  • Examples of the alkyloxy group include a cyclopentyloxy group and a cyclohexyloxy group, and a methoxy group, an ethoxy group, a 1-butoxy group, an isopropoxy group, and a t-butoxy group are particularly preferable.
  • alkylcarbonyl group which may have a substituent in the general formulas (2) to (6) are shown below.
  • Examples of the alkylcarbonyl group which may have a substituent include an acetyl group, a propylcarbonyl group, a heptyl-3-carbonyl group, a 2-ethylhexyloxymethylcarbonyl group, a phenoxymethylcarbonyl group, and a 2-ethylhexyloxycarbonylmethylcarbonyl group. Can be mentioned.
  • R 31 is synonymous with R 3 in the general formula (2), and preferred ranges are also the same.
  • c1 is synonymous with c in General formula (2), and its preferable range is also the same.
  • R 8 and R 9 each independently represents an alkyl group that may have a substituent or an aryl group that may have a substituent.
  • the alkyl group which may have a substituent and the aryl group which may have a substituent may have an alkyl group which may have a substituent in R 5 of the general formula (5) or a substituent. It is synonymous with a good aryl group, respectively, and its preferable range is also the same.
  • substituent T When the above-described substituent T is a further substitutable group, it may be further substituted with any of the above-described groups. In addition, when it has two or more substituents, those substituents may be the same or different. However, the substituent in the present invention preferably has a mass per molecule of 500 or less.
  • R 1, a, X, n, R, and r represents M in the general formula (1), respectively, R 1, a, X, n, R, and r.
  • Y and Ar are Y and an aromatic substituent in the general formula (2) and the general formula (3) represented by R 1 , respectively.
  • Ar-1 to Ar-49 in Table 1 each represent a substituent shown below. In the following substituents, • represents a bonding position. In the following substituents, Et represents an ethyl group, Me represents a methyl group, Ph represents a phenyl group, and Bu represents a butyl group. Moreover, Ph in Table 1 is a phenyl group.
  • the organic layer was concentrated and purified by silica gel chromatography to obtain 35 parts of 4- (N-acetyloxyethyl-N-ethylsulfamoyl) phenoxytrichlorophthalonitrile.
  • the substitution position of the hydroxyl group of 4- (N-acetyloxyethyl-N-ethylsulfamoyl) phenol is a mixture of the 3rd and 4th positions.
  • the reaction solution of the obtained substituted phthalonitrile (13.8 parts), zinc iodide (2.5 parts), and benzonitrile (30 parts) was reacted at 135 ° C. for 48 hours.
  • the reaction solution was extracted with ethyl acetate and 1N hydrochloric acid, and the organic layer was separated, concentrated, and purified by silica gel chromatography to obtain 8.2 parts of Exemplified Compound A-77.
  • zinc phthalocyanine in which a in formula (1) is 4 is synthesized in the same manner as the synthesis of exemplary compound A-78.
  • the compound was synthesized by the same method as that of Example Compound A-77.
  • the total content in the coloring composition of the dye containing the phthalocyanine compound represented by the general formula (1) should be small if the spectral characteristics can be satisfied.
  • the smaller the number the better from the viewpoint of sensitivity and developability.
  • the content of the phthalocyanine compound represented by the general formula (1) in the colored composition is preferably 1 to 80% by mass and more preferably 3 to 50% by mass with respect to the total solid content of the colored composition. By setting it as this range, coloring power and pattern formation property can be compatible.
  • the coloring composition of the present invention has a benzene ring substituted with a heteroaromatic ring, a polycyclic aromatic ring, or a group having a metal coordination property, and is a compound (B) (hereinafter, referred to as “light and heat stable”). It contains at least one of “compound (B)” as appropriate.
  • the polycyclic aromatic ring possessed by the compound (B) is sufficient if it has a plurality of aromatic rings, may be a condensed ring, or may be a compound in which a plurality of aromatic rings are bonded via a bond.
  • these polycyclic aromatic rings include polycyclic aromatic rings such as naphthalene ring, perylene ring, biphenyl structure, anthraquinone ring, phenanthrene ring and pyrene ring.
  • the heteroaromatic ring possessed by the compound (B) contains a nitrogen atom, oxygen atom and / or sulfur atom as a hetero atom, is a 5- to 6-membered aromatic ring, and further has a condensed ring.
  • the phthalocyanine derivative as the compound (B) is a compound having at least one phthalocyanine ring in the molecule and in which the central metal is not coordinated. Any compound may be used as long as it is 50% or less. Specific examples of the phthalocyanine derivative include compounds represented by the following general formula (b2) from the viewpoint of becoming a compound that is stable to light and heat.
  • the compound (B) may be a low molecular compound or a high molecular compound, but is preferably a high molecular compound.
  • the high molecular compound has a repeating unit structure, and the low molecular compound has no repeating unit.
  • the polymer compound is formed by polymerizing a polymerizable compound having a heteroaromatic ring or a polycyclic aromatic ring, and even when a polymerizable compound having a heteroaromatic ring or a polycyclic aromatic ring is polymerized alone, You may superpose
  • the polymerizable compound having a heteroaromatic ring or a polycyclic aromatic ring is not particularly limited, but preferably includes a vinyl monomer, and is preferably a compound represented by the following general formula (I).
  • (Meth) acryloyloxyalkyl] esters ⁇ -carboxy-polycaprolactone monoacrylate, ⁇ -carboxy-polycaprolactone monoacrylate
  • Mono (meth) acrylates such as both terminal carboxy polymers methacrylate and the like.
  • One type of repeating unit derived from a monomer having an acid group may be included, or two or more types may be included.
  • the content of the repeating unit derived from the monomer having an acid group is preferably 10 to 200 mgKOH / g, particularly preferably 50 to 150 mgKOH / g. . That is, from the viewpoint of alkali developability when the colored composition is a photosensitive colored composition, the content of the repeating unit derived from the monomer having an acid group is from 10 mgKOH / g to 200 mgKOH / g. Is preferred.
  • the colored composition of the present invention preferably contains an organic solvent. Any organic solvent can be used as long as it dissolves the phthalocyanine compound (A) and the compound (B) represented by the general formula (1). Moreover, even if an organic solvent is a thing which does not melt
  • Low molecular weight compounds containing polyglycidyl groups such as dipentaerythritol pentaglycidyl ether and dipentaerythritol hexaglycidyl ether, 1,2-epoxy of polyglycidyl (meth) acrylate, 2,2-bis (hydroxymethyl) -1-butanol Examples thereof include glycidyl group-containing polymer compounds represented by -4- (2-oxiranyl) cyclohexane adduct and the like.
  • the content of the alkali-soluble resin in the photosensitive coloring composition is preferably 10% to 90%, more preferably 20% to 80%, and more preferably 30% based on the total solid content of the composition. ⁇ 70% is particularly preferred.
  • the coloring composition of the present invention is prepared by mixing the above-described components and optional components as necessary.
  • the components constituting the coloring composition may be blended together, or may be sequentially blended after each component is dissolved and dispersed in a solvent.
  • the composition may be prepared by dissolving and dispersing all components in a solvent at the same time. If necessary, each component may be suitably used as two or more solutions / dispersions at the time of use (at the time of application). ) May be mixed to prepare a composition.
  • a pigment when used as a component, it is preferable to prepare a colored composition after previously dispersing the pigment to obtain a pigment dispersion.
  • the photosensitive coloring composition prepared as described above is preferably filtered using a filter having a pore size of about 0.01 ⁇ m to 3.0 ⁇ m, more preferably about 0.05 ⁇ m to 0.5 ⁇ m. Can be used for use.
  • Compound B1 to Compound B11, Compound B21 to Compound B26 > Compound B1 to Compound B11 and Compound B21 to Compound B26 having the structures shown below were used.
  • Compound B1 to Compound B10 and Compound B21 to Compound B26 correspond to the compound (B) in the present invention, and the compound B11 does not have a heteroaromatic ring or the like, and the compound (B) of the present invention includes Not applicable.
  • t-Bu represents a tert-butyl group.
  • the light resistance of the resin B10 and the compound B10 is inferior to other resins and compounds, but the degradation degree is 50% or less, and both resins and compounds are true compounds that are stable to light and heat. It can be seen that it is.
  • the resin B11 and the compound B11 do not have a heteroaromatic ring or a polycyclic aromatic ring, and are not the compound (B) in the present invention.
  • the phthalocyanine compound and the compound (B) or comparative compound were changed as shown in Table 9 to prepare colored compositions of Examples 1 to 16 and Comparative Examples 1 and 2.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • General Physics & Mathematics (AREA)
  • Optical Filters (AREA)
  • Structural Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Architecture (AREA)
  • Quinoline Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials For Photolithography (AREA)
PCT/JP2013/076130 2012-09-28 2013-09-26 Composition de coloration, composition de coloration photosensible, filtre coloré, procédé de fabrication de filtre coloré, élément d'imagerie à l'état solide et dispositif d'affichage d'image Ceased WO2014050998A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2012-217834 2012-09-28
JP2012217834 2012-09-28
JP2013184242A JP2014080578A (ja) 2012-09-28 2013-09-05 着色組成物、感光性着色組成物、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子、及び画像表示装置
JP2013-184242 2013-09-05

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TW (1) TW201412884A (fr)
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CN120829684A (zh) * 2025-09-19 2025-10-24 浙江材华科技有限公司 一种显示光刻胶用蓝光绿色锌酞菁染料及其合成方法

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JP5800114B1 (ja) 2014-03-04 2015-10-28 Jsr株式会社 表示素子、感光性組成物およびエレクトロウェッティングディスプレイ
CN105593756B (zh) 2014-07-31 2018-06-29 Jsr株式会社 显示元件、感光性组合物以及电润湿显示器
CN105474086A (zh) 2014-07-31 2016-04-06 Jsr株式会社 显示元件、感光性组合物以及电润湿显示器
JP7143432B2 (ja) * 2018-10-11 2022-09-28 富士フイルム株式会社 着色組成物、膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子及び画像表示装置
WO2020075569A1 (fr) * 2018-10-11 2020-04-16 富士フイルム株式会社 Composition de coloration, film, filtre coloré ainsi que procédé de fabrication de celui-ci, structure, élément d'imagerie à l'état solide, et dispositif d'affichage d'image

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