US20030229163A1 - Dye-containing curable composition, color filter prepared using the same, and process of preparing color filter - Google Patents

Dye-containing curable composition, color filter prepared using the same, and process of preparing color filter Download PDF

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Publication number
US20030229163A1
US20030229163A1 US10/400,079 US40007903A US2003229163A1 US 20030229163 A1 US20030229163 A1 US 20030229163A1 US 40007903 A US40007903 A US 40007903A US 2003229163 A1 US2003229163 A1 US 2003229163A1
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Prior art keywords
dye
acid
curable composition
amine compound
containing curable
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Inventor
Katsumi Araki
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Priority claimed from JP2002284160A external-priority patent/JP2004002631A/ja
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Assigned to FUJI PHOTO FILM CO., LTD. reassignment FUJI PHOTO FILM CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ARAKI, KATSUMI
Publication of US20030229163A1 publication Critical patent/US20030229163A1/en
Priority to US11/350,012 priority Critical patent/US7306884B2/en
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    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B57/00—Golfing accessories
    • A63B57/10—Golf tees
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/04—Dyestuff salts, e.g. salts of acid dyes with basic dyes of anionic dyes with nitrogen containing compounds
    • 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
    • A—HUMAN NECESSITIES
    • A63—SPORTS; GAMES; AMUSEMENTS
    • A63B—APPARATUS FOR PHYSICAL TRAINING, GYMNASTICS, SWIMMING, CLIMBING, OR FENCING; BALL GAMES; TRAINING EQUIPMENT
    • A63B2102/00—Application of clubs, bats, rackets or the like to the sporting activity ; particular sports involving the use of balls and clubs, bats, rackets, or the like
    • A63B2102/32—Golf

Definitions

  • the present invention relates to a dye-containing curable composition that is suitable for forming a colored image in a color filter used in liquid crystal displays or solid-state image elements, as well as to a color filter prepared using the composition, and to a process of preparing the color filter.
  • the dyeing process comprises dyeing a substrate, that is made of a natural resin (e.g., gelatin, glue and casein) or a synthetic resin (e.g., amine-modified polyvinyl alcohol), with a dye such as an acid dye, to thereby prepare a color filter.
  • a natural resin e.g., gelatin, glue and casein
  • a synthetic resin e.g., amine-modified polyvinyl alcohol
  • the dyeing process involves problems with respect to lightfastness, heat resistance and humidity resistance due to using the dye, a problem in that color unevenness occurs when producing large-size screens because it is difficult to uniformly control dyeing and fixing characteristics, and a problem in that a procedure is complicated since an anti-dyeing layer is needed when conducting the dyeing.
  • the electrodepositing process comprises forming transparent electrodes in a prescribed pattern beforehand, ionizing a resin that contains a pigment dissolved or dispersed in a solvent, and applying a voltage to form a colored image in accordance with a pattern shape, to thereby prepare a color filter.
  • This electrodepositing process requires a photolithographic step including film-forming and etching steps for producing transparent electrodes for forming a color filter in addition to transparent electrodes for display. During this process, if a short circuit occurs, line defects are generated leading to a reduction in yield. In principle, this process is difficult to apply to alignments other than a stripe alignment, such as a mosaic alignment. Moreover, this process has a problem in that control of the transparent electrodes is difficult.
  • the printing process is a simple and easy process for preparing a color filter, in which an ink that contains a thermosetting resin or a ultraviolet-curing resin and a pigment dispersed therein is used for printing, such as offset printing.
  • an ink that contains a thermosetting resin or a ultraviolet-curing resin and a pigment dispersed therein is used for printing, such as offset printing.
  • filtering is difficult, and defects resulting from contaminants, foreign matter or gelling of an ink binder are easily generated.
  • this process involves problems with respect to position precision, line width precision, and plane smoothness depending on printing precision.
  • the pigment dispersing process is a process employed for preparing a color filter, through a photographic technique using a colored radioactive composition containing a pigment dispersed in various photosensitive compositions. Since this process uses pigments, it is stable against light and heat. Further, since patterning is carried out by the photolithographic technique, the pigment dispersing process is suitable for the preparation of a color filter that achieves a sufficient position precision and is suitable for use in large-size screens and high resolution color displays.
  • a radioactive composition is applied on a glass substrate using a spin coater, a roll coater or the like, followed by drying to form a coated film, which is then subjected to pattern exposure and development to thereby form colored pixels. This procedure is carried out for respective colors to obtain the color filter.
  • negative-type photosensitive compositions which comprise a photopolymerizable monomer, a photopolymerization initiator and an alkali-soluble resin (see, for example, Japanese Patent Application Laid-Open (JP-A) Nos. 1-102469, 1-152499, 2-181704, 2-199403, 4-76062, 5-273411, 6-184482 and 7-140654).
  • JP-A Japanese Patent Application Laid-Open
  • Dye-containing curable compositions involve the following newly raised problems (1) to (4):
  • the composition in contrast to when applied for preparation of semiconductors, when applied for preparing color filters for solid-state image elements, the composition is required to have a film thickness of 1 ⁇ m or less. Accordingly, in order to exhibit a desired absorption, a large amount of the dye must be added to the curable composition, which results in occurrence of the foregoing problems.
  • dyes that contain salts with various amines having enhanced solubility with respect to acid dyes.
  • examples thereof include amine salts of “Acid Yellow 42” having solubility in alkaline aqueous solutions or organic solvents (e.g., ditolylguanidine salts).
  • these amine salts do not have an OH group in their imine moiety, interaction with other components present in a resist considerably lowers their alkaline developability.
  • an azo-based acid dye represented by “Acid Yellow 42” can take various conformations, a molar absorptive coefficient thereof may occasionally be lowered.
  • An object of the present invention is to provide a dye-containing curable composition that exhibits high sensitivity, high transmittance, high resolving power and wide development latitude, is free from dye elution, deterioration by heat and deterioration by light, and has high productivity, as well as a color filter prepared using the dye-containing curable composition, and a process of preparing the color filter.
  • a dye-containing curable composition that has the following constitution and is suitably applied to preparation of color filters, and a process of preparing a color filter are provided.
  • a first aspect of the invention is a dye-containing curable composition
  • a dye-containing curable composition comprising an alkali-soluble binder and an organic-solvent-soluble dye represented by the following formula (I):
  • Dye represents an acid dye
  • X represents an amine compound having an OH group and having a molecular weight of less than 230
  • n satisfies 0 ⁇ n ⁇ 10.
  • the amine compound represented by X in formula (I) has from 1 to 6 OH groups per molecular weight of 100.
  • the amine compound has, per molecular weight thereof of 100, preferably from 1 to 5 OH groups, more preferably from 1 to 4 OH groups, and most preferably from 1 to 3 OH groups.
  • the amine compound represented by X in formula (I) has up to 14 carbon atoms.
  • the amine compound has preferably up to 12 carbon atoms, more preferably up to 10 carbon atoms, and most preferably up to 8 carbon atoms.
  • the amine compound represented by X in formula (I) is a secondary or tertiary amine compound, with a tertiary amine compound being more preferable.
  • the amine compound represented by X in formula (I) has linear aliphatic or cyclic aliphatic carbons, with the linear aliphatic carbons being more preferable.
  • the amine compound represented by X in formula (I) has a surface energy of 10 to 80 dyn/cm, more preferably 15 to 70 dyn/cm, and most preferably 20 to 60 dyn/cm.
  • a second aspect of the invention is a dye-containing curable composition
  • a dye-containing curable composition comprising an alkali-soluble binder and an organic-solvent-soluble dye represented by the following formula (I):
  • Dye represents an acid dye
  • X represents an amine compound having an oxygen atom that forms an ether bond and having a molecular weight of 300 or less
  • n satisfies 0 ⁇ n ⁇ 10.
  • the amine compound represented by X in formula (I) has from 1 to 6 ether groups per molecular weight of 100.
  • the amine compound has, per molecular weight thereof of 100, preferably from 1 to 5 ether groups, more preferably 1 to 4 ether groups, and most preferably 1 to 3 ether groups.
  • the amine compound represented by X in formula (I) has up to 14 carbon atoms.
  • the amine compound has preferably up to 12 carbon atoms, more preferably up to 10 carbon atoms, and most preferably up to 8 carbon atoms.
  • the amine compound represented by X in formula (I) is a secondary or tertiary amine compound, with a tertiary amine compound being more preferable.
  • the amine compound represented by X in formula (I) has linear aliphatic or cyclic aliphatic carbons, with the linear aliphatic carbons being more preferable.
  • the amine compound represented by X in formula (I) has a surface energy of 10 to 80 dyn/cm, more preferably 15 to 70 dyn/cm, and most preferably 20 to 60 dyn/cm.
  • a third aspect of the invention is a dye-containing curable composition
  • a dye-containing curable composition comprising an alkali-soluble binder and an organic-solvent-soluble dye represented by the following formula (I):
  • Dye represents an acid dye
  • X represents an amine compound having a polymerizable group
  • n satisfies 0 ⁇ n ⁇ 10.
  • a fourth aspect of the invention is a color filter comprising a dye-containing curable composition according to any one of the first aspect, the second aspect and the third aspect.
  • a fifth aspect of the invention is a process of preparing a color filter, which comprises the steps of applying on a substrate the dye-containing curable composition according to any one of the first aspect, the second aspect and the third aspect, exposing the composition to light through a mask, and conducting development to form a pattern.
  • This preparation process may comprise an additional step of curing the pattern by heating and/or exposing to light, as necessary, and the above-described steps may be repeated plural times.
  • a dye-containing curable composition, a color filter prepared using the composition, and a process of preparing the color filter according to the present invention will be described in detail below.
  • composition of the invention is a dye-containing curable composition comprising an alkali-soluble binder and an organic-solvent-soluble dye, and the organic-solvent-soluble dye is a compound represented by the following formula (I).
  • Dye represents an acid dye
  • X represents an amine compound having an OH group and having a molecular weight of less than 230
  • n satisfies 0 ⁇ n ⁇ 10.
  • Dye represents an acid dye
  • X represents an amine compound having an oxygen atom that forms an ether bond and having a molecular weight of 300 or less
  • n satisfies 0 ⁇ n ⁇ 10.
  • Dye represents an acid dye
  • X represents an amine compound having a polymerizable group
  • n satisfies 0 ⁇ n ⁇ 10.
  • the amine compound represented by X preferably has a molecular weight of 700 or less, more preferably 600 or less, further preferably 500 or less, and most preferably 400 or less.
  • the polymerizable group in the amine compound represented by X is preferably at least one member selected from a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, an epoxy group, a stylyl group, and a vinyl ester group.
  • a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, an epoxy group, and a stylyl group are more preferable;
  • a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, and an epoxy group are more preferable;
  • a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, and a glycidyl group are most preferable.
  • the amine compound represented by X preferably contains 15 or less polymerizable groups, more preferably 12 or less polymerizable groups, still more preferably 8 or less polymerizable groups, and most preferably 6 or less polymerizable groups.
  • the composition of the invention may contain a crosslinking agent.
  • the composition may include a monomer and a photopolymerization initiator in addition to the aforementioned alkali-soluble binder and organic-solvent-soluble dye, and may further include a crosslinking agent.
  • the organic-solvent-soluble dye for use in the invention is a compound comprising a salt of an acid dye and an amine compound, as represented by the above formula (I).
  • the acid dye will be described below.
  • the acid dye is not particularly limited insofar as it is a dye having an acid group such as a sulfonic acid group, a carboxylic acid group and a phenolic hydroxyl group.
  • the dye is selected considering all of preferential orders of required performances, such as solubility in the organic solvent or developing solution, ability to form a salt with a basic compound, absorbance, interaction with other components in the curable composition, lightfastness, and heat resistance.
  • Acid Alizarin Violet N Acid Black 1, 2, 24, 48; Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; Acid Chrome Violet K; Acid Fuchsin; Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109; Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169
  • Acid Black 24 Acid Blue 23, 25, 29, 62, 80, 86, 87, 92, 138, 158, 182, 243, 324; Acid Orange 8, 51, 56, 63, 74; Acid Red 1, 4, 8, 34, 37, 42, 52, 57, 80, 97, 114, 143, 145, 151, 183, 217; Acid Violet 7; Acid Yellow 17, 25, 29, 34, 38, 42, 65, 72, 76, 99, 111, 112, 114, 116, 134, 155, 169, 172, 184, 220, 228, 230, 232, 243; Acid Green 25; Mordant Yellow 3; and derivatives of these dyes.
  • azo-based, xanthene-based and phthalocyanine-based acid dyes such as C.I. Solvent Blue 44, 38; C.I. Solvent Orange 45; Rhodamine B; Rhodamine 110; 2,7-naphthalenedisulfonic acid; 3-[(5-chloro-2-phenoxyphenyl)hydrazino]-3,4-dihydro-4-oxo-5-[(phenylsulfonyl)amino]; and derivatives of these dyes, are preferable.
  • Examples of the acid dye derivative include inorganic salts of an acid dye having an acid group of a sulfonic acid, a carboxylic acid or the like, salts of an acid dye and a nitrogen-containing compound, and (sulfon)amide compounds of an acid dye.
  • the acid dye derivatives are not particularly limited insofar as they may be dissolved as the curable composition solution, however, they are selected considering all of the required performances, such as solubility in the organic solvent or developing solution, absorbance, interaction with other components in the curable composition, lightfastness, and heat resistance.
  • preferable acid dyes are azo-based, anthraquinone-based, anthrapyridone-based and phthalocyanine-based dyes.
  • a compound represented by the following general formula (II) may be preferably used as the azo-based acid dye.
  • a and B each independently represent an optionally substituted pyrazole ring, benzene ring, naphthalene ring or acetylacetone residue.
  • Representative examples of the compound represented by the general structure (II) include the following compounds.
  • the amine compound represented by X has an OH group and has a molecular weight of less than 230.
  • the amine compound is selected considering all of the required performances such as solubility in the organic solvent or developing solution, salt forming properties, absorbance of the dye, and interaction with other components in the curable composition.
  • the molecular weight of the amine compound is as low as possible.
  • the molecular weight of the amine compound is preferably 220 or less, more preferably 200 or less, and most preferably 180 or less.
  • the amine compound represented by X has an oxygen atom that forms an ether bond and has a molecular weight of 300 or less.
  • the amine compound is selected considering all of the required performances such as solubility in the organic solvent or developing solution, salt forming properties, absorbance of the dye, and interaction with other components in the curable composition.
  • the molecular weight of the amine compound is as low as possible.
  • the molecular weight of the amine compound is preferably 250 or less, more preferably 230 or less, and most preferably 200 or less.
  • the amine compound represented by X has a polymerizable group.
  • the amine compound is selected considering all of the required performances such as solubility in the organic solvent or developing solution, salt forming properties, absorbance of the dye and interaction with other components in the curable composition.
  • the molecular weight of the amine compound is as low as possible.
  • the molecular weight of the amine compound is preferably 700 or less, more preferably 600 or less, further preferably 500 or less, and most preferably 400 or less.
  • Examples of the polymerizable group, which the above-described amine compound has, include a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, an epoxy group, a stylyl group, and a vinyl ester group.
  • a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, an epoxy group, and a stylyl group are preferable;
  • a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, and an epoxy group are more preferable;
  • a (meth)acrylic ester group, a (meth)acrylamide group, an allyl group, an isopropenyl group, a vinyl ether group, and a glycidyl group are most preferable.
  • amine compounds having, as the polymerizable group, an acryloyl group, a methacryloyl group, a glycidyl group, an allyl group, a 2-methylallyl group or a vinyl ether group are preferable.
  • amine compound having, as the polymerizable group, an acryloyl group, a methacryloyl group, a glycidyl group, an allyl group or a 2-methylallyl group include the following compounds, that are obtained by reacting an amine compound having a terminal hydroxyl group and/or a terminal amino group with a corresponding a (meth)acrylic acid halide, epichrolohydrin, an allyl halide, a 2-methyl-allyl halide or the like.
  • the number of the polymerizable groups which the foregoing amine compound contains has preferably 15 or less, more preferably 12 or less, further preferably 8 or less, and most preferably 6 or less.
  • n is a value to determine a molar ratio between the acid dye molecule and the amine compound that acts as a counter ion, and the value may freely be selected depending on the conditions to form the acid dye-amine compound salt.
  • n represents a numeral value relative to the acid dye, which should satisfy the equivalent range of 0 ⁇ n ⁇ 10, and is selected considering all of preferential orders of the required performances, such as solubility in the organic solvent or developing solution, salt forming properties, absorbance, interaction with other components in the curable composition, lightfastness, and heat resistance.
  • n is preferably a numeral value for the acid dye which satisfies 0 ⁇ n ⁇ 8, more preferably 0 ⁇ n ⁇ 6, and most preferably 0 ⁇ n ⁇ 4.
  • the concentration of the organic-solvent-soluble dye to be used will be described.
  • the organic-solvent-soluble dye is contained at varying concentrations relative to a total solid content of the dye-containing curable composition of the invention.
  • the concentration varies depending on the kinds of the dye used, but preferably ranges from 0.5 to 80% by mass, more preferably from 0.5 to 60% by mass, and most preferably from 0.5 to 50% by mass.
  • the binder used in the invention is not particularly limited insofar as it is alkali-soluble. It is preferably selected from the viewpoints of heat resistance, developability and readily availability.
  • linear-shaped organic high-molecular polymers that are soluble in an organic solvent and may be developed with a weak alkaline aqueous solution are preferable.
  • the linear-shaped organic high-molecular polymer include polymers having a carboxylic acid in the side chain thereof, such as methacrylic acid copolymers, acrylic acid copolymers, itaconic acid copolymers, crotonic acid copolymers, maleic acid copolymers, and partially esterified maleic acid copolymers as described in Japanese Patent Application Laid-Open (JP-A) No. 59-44615, Japanese Patent Application Publication (JP-B) Nos.
  • acidic cellulose derivatives having a carboxylic acid in the side chain thereof are useful.
  • hydroxyl group-containing polymers having added thereto an acid anhydride, polyhydroxystyrene-based resins, polysiloxane-based resins, poly(2-hydroxyethyl(meth)acrylate), polyvinylpyrrolidone, polyethylene oxide and polyvinyl alcohol are useful.
  • Copolymers produced from a hydrophilic group-containing monomer are also useful.
  • examples of such a monomer include alkoxyalkyl (meth)acrylates, hydroxyalkyl (meth)acrylates, glycerol (meth)acrylate, (meth)acrylamide, N-methyloyl acrylamide, secondary or tertiary alkyl acrylamides, dialkylaminoalkyl (meth)acrylates, morpholine (meth)acrylates, N-vinylpyrrolidone, N-vinylcaprolatam, vinyl imidazole, vinyl triazole, methyl (meth)acrylate, ethyl (meth)acrylate, branched or linear propyl (meth)acrylate, branched or linear butyl (meth)acrylate, and phenoxyhydroxypropyl (meth)acrylate.
  • hydrophilic group-containing monomer examples include monomers containing a tetrahydrofurfuryl group, phosphoric acid, phosphoric acid ester, a quaternary ammonium salt, an ethyleneoxy chain, a propyleneoxy group, sulfonic acid or a salt thereof, or a morpholinoethyl group.
  • the polymer containing a polymerizable group in the side chain thereof polymers having an allyl group, a (meth)acryl group or an allyloxyalkyl group in the side chains thereof are useful.
  • KS RESIST-106 (trade name, manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.) and CYCLOMER-P SERIES (trade name, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD.) is mentioned.
  • alcohol-soluble nylons and a polyether between 2,2-bis(4-hydroxyphenyl)propane and epichlorohydrin are useful.
  • polyhydroxystyrene-based resins, polysiloxane-based resins, acrylic resins, acrylamide-based resins and acrylic/acrylamide copolymer resins are preferable binders for use in the invention, from the viewpoint of heat resistance; and acrylic resins, acrylamide-based resins, and acrylic/acrylamide copolymer resins are preferable from the viewpoint of controlling the developability.
  • acrylic resin copolymers produced from a monomer selected from benzyl (meth)acrylate, (meth)acrylic acid, hydroxyethyl (meth)acrylate, (meth)acrylamide, KS RESIST-106 (trade name, manufactured by OSAKA ORGANIC CHEMICAL INDUSTRY LTD.), and CYCLOMER-P SERIES are preferable.
  • the binder to be used in the invention alkali-soluble phenol resins is preferable.
  • the alkali-soluble phenol resin may suitably be used in the case where the composition of the invention is a positive-type composition. Examples of the alkali-soluble phenol resin include novolak resins and vinyl polymers.
  • the novolak resin products obtained by condensing phenols with aldehydes in the presence of an acid catalyst are preferably used.
  • the phenols include phenol, cresol, ethylphenol, butylphenol, xylenol, phenylphenol, catechol, resorcinol, pyrogallol, naphthol, and bisphenol A. Phenols can be used singly or in combination of two or more thereof.
  • the aldehyde include formaldehyde, p-formaldehyde, acetaldehyde, propionaldehyde and benzaldehyde.
  • the novolak resin include condensates of m-cresol, p-cresol or a mixture thereof with formalin.
  • the molecular weight distribution of the novolak resin may be controlled by means of, for example, fractionation.
  • the novolak resin may include a low-molecular component having a phenolic hydroxyl group, such as bisphenol C and bisphenol A.
  • binder polymers having a weight average molecular weight (in terms of a polystyrene value measured by the GPC method) of from 1,000 to 2 ⁇ 10 5 are preferable; polymers having a weight average molecular weight of from 2,000 to 1 ⁇ 10 5 are more preferable; and polymers having a weight average molecular weight of from 5,000 to 5 ⁇ 10 4 are most preferable.
  • An amount of the binder to be used in the composition of the invention is preferably from 10 to 90% by mass, more preferably from 20 to 80% by mass, and most preferably from 30 to 70% by mass.
  • the object of the invention is to provide a highly curable film by allowing a curing reaction in the film to more swiftly proceed than the conventional reaction, using the organic-solvent-soluble dye represented by the above formula (I). Further, it is possible to obtain a still further highly cured film using a crosslinking agent.
  • the crosslinking agent used in the invention is not particularly limited insofar as the film may be cured by crosslinking reaction.
  • crosslinking agent examples include (a) epoxy resins, (b) melamine compounds, guanamine compounds, glycoluryl compounds, or urea compounds, each of which is substituted with at least one substituent selected from a methylol group, an alkoxymethyl group, and an acyloxymethyl group, and (c) phenol compounds, naphthol compounds, or hydroxyanthracene compounds, each of which is substituted with at least one substituent selected from a methylol group, an alkoxymethyl group, and an acyloxymethyl group.
  • polyfunctional epoxy resins are preferable as the crosslinking agent.
  • any crosslinkable compounds having an epoxy group can be used.
  • examples thereof include divalent glycidyl-containing low-molecular compounds such as bisphenol A diglycidyl ether, ethylene glycol diglycidyl ether, butanediol diglycidyl ether, hexanediol diglycidyl ether, dihydroxybiphenyl diglycidyl ether, diglycidyl phthalate and N,N-diglycidylaniline; trivalent glycidyl group-containing low-molecular compounds such as trimethylolpropane triglycidyl ether, trimethylolphenol triglycidyl ether, and TrisP-PA triglycidyl ether; tetravalent glycidyl group-containing low-molecular compounds such as pentaerythritol tetraglycidyl ether and tetramethylo
  • the number of the substituents in the component (b), which are selected from a methylol group, an alkoxymethyl group and an acyloxymethyl group, is from 2 to 6 in the case of the melamine compounds, and from 2 to 4 in the case of the glycoluril compounds, guanamine compounds or urea compounds, respectively, and preferably from 5 to 6 in the case of the melamine compounds, and from 3 to 4 in the case of the glycoluril compounds, guanamine compounds or urea compounds, respectively.
  • methylol group-containing compounds are obtained by heating the foregoing alkoxymethyl group-containing compound in an alcohol in the presence of an acid catalyst such as hydrochloric acid, sulfuric acid, nitric acid and methanesulfonic acid.
  • the acyloxymethyl group-containing compound is obtained by mixing, with stirring, the methylol group-containing compound and an acyl chloride in the presence of a basic catalyst.
  • Examples of the melamine compounds include hexamethylolmelamine, hexamethoxymethylmelamine, compounds in which one to five methylol groups in hexamethylolmelamine are methoxymethylated or the mixtures thereof, hexamethoxyethylmelamine, hexaacyloxymethylmelamine, and compounds in which one to five methylol groups in hexamethylolmelamine are acyloxymethylated or the mixtures thereof.
  • Examples of the guanamine compound include tetramethylolguanamine, tetramethoxymethylguanamine, compounds in which from one to three methylol groups in tetramethylolguanmine are methoxymethylated or the mixtures thereof, tetramethoxyethylguanamine, tetraacyloxymethylguanamine, and compounds in which from one or three methylol groups in tetramethylolguanamine are acyloxymethylated or the mixtures thereof.
  • glycoluril compound examples include tetramethylolglycoluryl, tetramethoxymethylglycoluryl, compounds in which one to three methylol groups of tetramethyloylglycoluryl are methoxymethylated or mixtures thereof, and compounds in which one to three methylol groups in tetramethylolglycoluryl are acyloxymethylated or the mixtures thereof.
  • urea compound examples include tetramethylolurea, tetramethoxymethylurea, compounds in which one to three methylol groups in tetramethylolurea are methoxymethylated or the mixtures thereof, and tetramethoxyethylurea. These compounds may be used singly or in combination thereof.
  • the phenol compound, naphthol compound or hydroxyanthracene compound to be contained as the component (c), which is substituted with at least one group selected from a methylol group, an alkoxymethyl group and an acyloxymethyl group, contributes not only to suppress intermixing with a topcoat photoresist but also to increase the film strength by thermal crosslinking, similarly to the case of the component (b) described above.
  • the number of the substituents in the component (c), which are selected from a methylol group, an alkoxymethyl group and an acyloxymethyl group, should be at least two per molecule. Phenolic compounds in which all of the 2- and 4-positions are substituted are preferable from the viewpoints of thermal crosslinking properties and storability.
  • the phenol compound to serve as the skeleton may be unsubstituted or substituted at the 3- or 5-position thereof.
  • the naphthol compound to serve as the skeleton may be unsubstituted or substituted at other positions than the ortho-position with respect to the OH group.
  • the methylol group-containing compounds are obtained by reacting, as the starting material, a compound having a hydrogen atom at the ortho- or para-position (2- or 4-position) with respect to the phenolic OH group with formalin in the presence of a basic catalyst such as sodium hydroxide, potassium hydroxide, ammonia and a tetraalkylammonium hydroxide.
  • a basic catalyst such as sodium hydroxide, potassium hydroxide, ammonia and a tetraalkylammonium hydroxide.
  • the alkoxymethyl group-containing compounds are obtained by heating the foregoing methylol group-containing compound in an alcohol in the presence of an acid catalyst such as hydrochloric acid, sulfuric acid, nitric acid and methanesulfonic acid.
  • an acid catalyst such as hydrochloric acid, sulfuric acid, nitric acid and methanesulfonic acid.
  • the acyloxymethyl group-containing compounds are obtained by reacting the foregoing methylol group-containing compound with an acyl chloride in the presence of a basic catalyst.
  • Examples of the skeleton compound include phenol compounds in which the ortho- or para-position with respect to the phenolic OH group is substituted, naphthol compounds, and hydroxyanthracene compounds, such as phenol, various isomers of cresol, 2,3-xylenol, 2,5-xylenol, 3,4-xylenol, 3,5-xylenol, bisphenols (e.g., bisphenol A), 4,4′-bishydroxybiphenyl, TrisP-PA (trade name, manufactured by HONSHU CHEMICAL INDUSTRY CO., LTD.), naphthol, dihydroxynaphthalene and 2,7-dihydroxyanthracene.
  • phenol compounds in which the ortho- or para-position with respect to the phenolic OH group is substituted such as phenol, various isomers of cresol, 2,3-xylenol, 2,5-xylenol, 3,4-xylenol, 3,5-x
  • component (c) include trimethylolphenol, tri(methoxymethyl)phenol, compounds in which one to two methylol groups in trimethylolphenol are methoxymethylated, trimethylol-3-cresol, tri(methoxymethyl)-3-cresol, compounds in which one to two methylol groups in trimethylol-3-cresol are methoxymethylated, dimethylolcresols such as 2,6-dimethylol-4-cresol, tetramethylol bisphenol A, tetramethoxymethyl bisphenol A, compounds in which one to three methylol groups of tetramethylol bisphenol A are methoxymethylated, tetramethylol-4,4′-bishydroxybiphenyl, tetramethoxymethyl-4,4′-bishydroxybiphenyl, a hexamethylol compound of TrisP-PA, a hexamethoxymethyl compound of TrisP-PA, compounds in which one to
  • acyloxymethyl group-containing compounds include compounds in which a part or all of the methylol groups in the foregoing methyl group-containing compounds are acyloxymethylated.
  • trimethylolphenol bishydroxymethyl-p-cresol, tetramethylol bisphenol A, a hexamethylol compound of TrisP-PA (trade name, manufactured by HONSHU CHEMICAL INDUSTRY CO., LTD.), and phenol compounds in which the methylol groups in the foregoing compounds are substituted with an alkoxymethyl group or both a methylol group and an alkoxymethyl group.
  • TrisP-PA trade name, manufactured by HONSHU CHEMICAL INDUSTRY CO., LTD.
  • phenol compounds in which the methylol groups in the foregoing compounds are substituted with an alkoxymethyl group or both a methylol group and an alkoxymethyl group.
  • the content of the components (a) to (c) in the dye-containing curable composition of the invention varies depending on the kinds thereof used.
  • the component is contained in an amount of preferably from 1 to 70% by mass, more preferably from 5 to 50% by mass, and most preferably from 7 to 30% by mass, relative to a total solid content of the composition.
  • the monomer that is contained in the case where the composition of the invention is a negative-type composition will be described.
  • the monomer compounds having an ethylenically unsaturated group, that have at least one addition polymerizable ethylene group and have a boiling point of 100° C. or higher at atmospheric pressure, are preferable.
  • Examples thereof include monofunctional acrylates or methacrylates such as polyethylene glycol mono(meth)acrylate, polypropylene glycol mono(meth)acrylate, and phenoxyethyl (meth)acrylate; polyfunctional acrylates or methacrylates such as polyethylene glycol di(meth)acrylate, trimethylolethane tri(meth)acrylate, neopentyl glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, hexanediol (meth)acrylate, trimethylolpropane tri(acryloyloxypropyl) ether, tri(acryloyloxyethyl)isocyanurate, compounds obtainable by adding ethylene oxide or propylene
  • the monomer is contained in an amount of from 0.1 to 90% by mass, more preferably from 1.0 to 80% by mass, and most preferably from 2.0 to 70% by mass, relative to a total solid content of the composition of the invention.
  • the photo-polymerization initiator that is contained in the case where the composition of the invention is a negative-type composition will be described.
  • the photo-polymerization initiator is not particularly limited insofar as it can polymerize the polymerizable monomer, but preferably, it is selected from the viewpoints of characteristics, polymerization initiating efficiency, absorption wavelength, readily availability, and costs.
  • Examples of the photo-polymerization initiator include at least one active halogen compound selected from halomethyl oxadiazole compound and halomethyl-s-triazine compound, 3-aryl-substituted coumarin compound, lophine dimer, benzophenone compound, acetophenone compound and the derivatives thereof, a cyclopentadiene-benzene-iron complex and the salts thereof, and oxime-based compound.
  • active halogen compound selected from halomethyl oxadiazole compound and halomethyl-s-triazine compound, 3-aryl-substituted coumarin compound, lophine dimer, benzophenone compound, acetophenone compound and the derivatives thereof, a cyclopentadiene-benzene-iron complex and the salts thereof, and oxime-based compound.
  • Examples of the active halogen compound such as halomethyl oxadiazoles, include 2-halomethyl-5-vinyl-1,3,4-oxadiazole compound as described in JP-B No. 57-6096, 2-trichloromethyl-5-styryl-1,3,4-ozadiazole, 2-trichloromethyl-5-(p-cyanostyryl)-1,3,4-oxadiazole, and 2-trichloromethyl-5-(p-methoxystyryl)-1,3,4-oxadiazole.
  • halomethyl-s-triazine compounds used as the photopolymerization initiator include vinyl-halomethyl-s-triazine compound as described in JP-B No. 59-1281, 2-(naphth-1-yl)-4,6-bis-halomethyl-s-triazine compound as described in JP-A No. 53-133428, and 4-(p-aminophenyl)-2,6-di-halomethyl-3-triazine compound as described in JP-A No. 53-133428.
  • TAZ Series of MIDORI KAGAKU CO., LTD. e.g., TAZ-107, TAZ-110, TAZ-104, TAZ-109, TAZ-140, TAZ-204, TAZ-113, TAZ-123, TAZ-104
  • T Series of PANCHIM CORP e.g., TAZ-107, TAZ-110, TAZ-104, TAZ-109, TAZ-140, TAZ-204, TAZ-113, TAZ-123, TAZ-104
  • IRGACURETM Series of CIBA-GEIGY e.g., IRGACURETM 369, IRGACURETM 784, IRGACURETM 651, IRGACURETM 184, IRGACURETM 500, IRGACURETM 1000, IRGACURETM 149, IRGACURETM 819, IRGACURETM 261), DAROCURETM Series of CIBA-GEIGY (e.g., DAROCURETM 1173), 4,4′-bis(diethylamino)-benzophenone, 2-(O-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 2-beznyl-2-dimethylamino-4-morpholinobutyrophenone, 2,2-dimethoxy-2-phenylacetophenone, 2-(o-chlorophenyl)-4,5-dipheny
  • the photopolymerization initiator may be used in combination with a sensitizer and a photo-stabilizer.
  • Specific examples include benzoin, benzoin methyl ether, benzoin, 9-fluorenone, 2-chloro-9-fluorenone, 2-methyl-9-fluorenone, 9-anthrone, 2-bromo-9-anthrone, 2-ethyl-9-anthrone, 9,10-anthraquinone, 2-ethyl-9,10-anthraquinone, 2-t-butyl-9,10-anthraquinone, 2,6-dichloro-9,10-anthraquinone, xanthone, 2-methylxanthone, 2-methoxyxanthone, 2-ethoxyxanthone, thioxanthone, 2,4-diethylthioxanthone, acridone, 10-butyl-2-chloroacridone, benzil, dibenzalacetone, p-(dimethylamino)phenyl styryl ketone, p-(
  • composition of the invention other known photopolymerization initiators other than the foregoing photopolymerization initiators can be incorporated.
  • Specific examples include vicinal polyketolaldonyl compounds as disclosed in U.S. Pat. No. 2,367,660, ⁇ -carbonyl compounds as disclosed in U.S. Pat. Nos. 2,367,661 and 2,367,670, acyloin ethers as disclosed in U.S. Pat. No. 2,448,828, aromatic ⁇ -hydrocarbon-substituted acyloin compounds as disclosed in U.S. Pat. No.2,722,512, polynuclear quinone compounds as disclosed in U.S. Pat. Nos. 3,046,127 and 2,951,758, a combination of triallyl imidazole dimer and p-aminophenyl ketone as disclosed in U.S. Pat. No. 3,549,367, and benzothiazole-based compounds/trihalomethyl-s-triazine-based compounds as disclosed in JP-B No. 51-48516.
  • the amount of the photopolymerization initiator to be used is preferably from 0.01 to 50% by mass, more preferably from 1 to 30% by mass, and most preferably from 1 to 20% by mass based on the monomer solids content.
  • the amount of the photopolymerization initiator used is less than 0.01% by mass, the polymerization hardly proceeds.
  • it exceeds 50% by mass although the polymerization ratio increases, the molecular weight is lowered to thereby sometimes reduce the film strength.
  • thermal polymerization preventing agent it is preferable to add a thermal polymerization preventing agent to the composition of the invention, besides the above components.
  • thermal polymerization preventing agent include hydroquinone, p-methoxyphenol, di-t-butyl p-cresol, pyrogallol, t-butylcatechol, benzoquinone, 4,4′-thiobis (3-methyl-6-t-butylphenol), 2,2′-methylenebis(4-methyl-6-t-butylphenol) and 2-mercaptobenzoimidazole.
  • the solvent to be used in the invention is not particularly limited insofar as it meets the solubility and coating properties of the composition, but preferably, it is selected considering solubility of the dye or the binder, coating properties, and safety.
  • esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate; alkyl 3-oxypropionates (e.g., methyl 3-oxypropionate, ethyl 3-oxypropionate), methyl 3-methoxypropionate, ethyl 3-me
  • methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate are more preferable.
  • composition of the invention may include various additives such as fillers, high-molecular compounds other than those described above, surfactants, adhesion promoters, antioxidants, UV absorbents and anti-flocculants.
  • additives include fillers such as glass and alumina; high-molecular compounds other than the binder resin, such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, and polyfluoroalkyl acrylates; nonionic, cationic and anionic surfactants; adhesion promoters such as vinyl trimethoxysilane, vinyl triethoxysilane, vinyl tris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyl dimethoxysilane, N-(2-aminoethyl)-3-aminopropyl trimethoxysilane, 3-aminopropyl trimethoxysilane, 3-glycidoxypropyl trimethoxysilane, 3-glycidoxypropylmethyl dimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyl trimethoxy
  • an organic carboxylic acid preferably a low-molecular organic carboxylic acid having a molecular weight of 1,000 or less may be added to the composition of the invention.
  • organic carboxylic acid examples include aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, diethylacetic acid, enanthic acid and caprylic acid; aliphatic dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassylic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, tetramethylsuccinic acid and citraconic acid; aliphatic tricarboxylic acids such as tricarballylic acid, aconitic acid and camphoronic acid; aromatic monocarboxylic acids such as benzoic acid, toluic acid, cuminic acid, hemellitic acid and mesitylenic acid;
  • composition of the invention is a positive-type composition
  • Examples of the naphthoquinonediazide compound include o-naphthoquinonediazide-5-sulfonic acid ester, o-naphthoquinonediazide-5-sulfonic acid amide, o-naphthoquinonediazide-4-sulfonic acid ester, and o-naphthoquinonediazide-4-sulfonic acid amide.
  • ester or amide compounds may be produced through the conventionally known method using phenol compounds represented by the formula (I) as described in JP-A Nos. 2-84650 and 3-49437.
  • composition of the invention is a positive-type composition
  • the color filter of the invention is produced using the composition of the invention.
  • the color filter of the invention can be produced by applying the composition of the invention on a substrate employing conventionally coating methods such as rotary coating, cast coating and roll coating, to dispose a radiation-sensitive composition layer, which is then exposed to light through a prescribed mask pattern and developed with a developing solution to thereby form a colored pattern. Further, the production process of the color filter of the invention may optionally include the step of heating and/or light-exposing of the resist pattern for curing.
  • UV rays such as g-line, h-line and i-line are particularly preferable.
  • Examples of the substrate include soda glass, PILEXTM glass, quartz glass, glass having a transparent conductive film adhered thereto, and a substrate for photoelectric transfer devices used in image pickup elements or the like, such as a silicon substrate and a complementary metal oxide semiconductor (CMOS). On these substrates, black stripes may be formed so as to isolate pixels from each other.
  • CMOS complementary metal oxide semiconductor
  • a subbing layer may be optionally disposed on the substrate in order to improve the adhesiveness to the upper layer, to prevent the substance diffusion, or to flatten the substrate surface.
  • any developing solution may be used insofar as it dissolves the composition of the invention but dose not dissolve a radiation-irradiated area.
  • any developing solution may be used insofar as it dissolves the composition of the invention but dose not dissolve a radiation-irradiated area.
  • a variety of combinations of organic solvents or alkaline aqueous solutions may be used.
  • the organic solvent the foregoing solvents used during preparation of the composition of the invention are preferable.
  • an alkaline aqueous solution is used in which an alkaline compound (e.g., sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, pyridine, and 1,8-diazabicyclo-[5.4.0]-7-undecene) is dissolved at a concentration from 0.001 to 10% by mass, and preferably from 0.01 to 1% by mass.
  • washing with water is usually carried out after the development.
  • the color filter of the invention can be used for liquid crystal displays or solid-state image elements such as CCD, and is particularly suitable for CCD elements or CMOS elements that have more than 1,000,000 pixels and display high resolution.
  • the color filter of the invention may be used as a color filter by being arranged between a light-receiving portion of respective pixels that constitute CCD, and a light-condensing micro lens.
  • a glass substrate (CORNINGTM 1737) was ultrasonically washed with a 1% NaOH aqueous solution, then with water, and baked for dehydration at 200° C. for 30 minutes.
  • the resist solution prepared in 1) above was applied on the washed glass substrate using a spin coater to give a film thickness of 2 ⁇ m and dried with heating at 220° C. for one hour to obtain a cured film.
  • the dye resist solution prepared in 3) above was applied on the subbing layer of the glass substrate that had been provided with the subbing layer as prepared in 2) above using a spin coater to give a film thickness of 2 ⁇ m and pre-baked at 120° C. for 120 seconds.
  • the coating film was exposed to light having a wavelength of 365 nm at a dose of 800 mJ/cm 2 through a 20 ⁇ m-thick mask using an exposure apparatus. After the exposure, the resulting film was developed at 26° C. for 60 seconds with a 60% CD-2000 developing solution (manufactured by FUJIFILM ARCH CO., LTD.). Thereafter, the thus developed film was rinsed with running water for 20 seconds and then spray-dried.
  • a 60% CD-2000 developing solution manufactured by FUJIFILM ARCH CO., LTD.
  • Example 2 The same procedures were repeated as in Example 1, except that respective dye resist solution compositions in Example 1-3) were changed as shown in the above Table 1. The results are shown in Table 2 including the results in Example 1.
  • Examples 8 to 14 the silicon wafer was used as the substrate, which was different from the substrate used in Examples 1 to 7. However, in all of Examples 1 to 14, the dye resist solution was applied over the subbing layer, whereby the same various performances were obtained without producing any substantial difference.
  • Example 2 The same procedures were conducted as in Example 1, except that respective dye resist solution compositions in Example 1-3) were changed as shown in the above Table 1. The obtained results are also shown in Table 2.
  • Example 8 228 Example Acid Blue 635 Diethanol 105 845 75 1.32 0.65 9.35 100 97 20 80 amine Comp. Acid Blue 635 Ditolylguanidine 239 1113 57 1.00 0.85 9.15 55 70
  • Example 9 80
  • Example Acid Blue 532 Diethanol 105 742 72 1.36 0.62 9.38 100 98 21 23 amine
  • Example 23 10 Example Acid Blue 394 Diethanol 105 499 79 1.27 0.67 9.33 100 97 22 25 amine Comp.
  • Acid Blue 394 Ditolylguanidine 239 633 62 1.00 0.85 9.15 70 63
  • Example 25 11 Example Acid Blue 451 Diethanol 105 550 81 1.24 0.68 9.32 100 95 23 324:1 amine Comp. Acid Blue 451 Ditolylguanidine 239 690 65 1.00 0.85 9.15 55 59
  • Example 324:1 12 Example Acid Yellow 687 Diethanol 105 792 87 1.17 0.73 9.27 100 97 24 38 amine Comp. Acid Yellow 687 Ditolylguanidine 239 926 74 1.00 0.85 9.15 67 69
  • Example 38 13 Example Acid Yellow 591 Diethanol 105 696 85 1.23 0.69 9.31 100 95 25 65 amine Comp.
  • Example 2 The same procedures were carried out as in Example 1 to prepare a resist solution, from which a subbing layer was prepared on the glass substrate, to thereby produce a cured film.
  • the obtained resist solution was mixed with each of dye salts and dissolved at proportions as shown in Table 4 so as to produce the film having the same absorbance with respect to the same kind of the dyes used.
  • the dye resist was subjected to exposure and development (image formation) in the same manner as in Example 1.
  • image formation was confirmed by the conventional method through observation using an optical microscope and SEM photographs.
  • the relative absorbance intensity, developability in an unexposed area, and residual layer ratio in an exposed area were each measured using a chromoscope, MCPD-1000 (manufactured by OTSUKA ELECTRONICS CO., LTD.).
  • the developability in an unexposed area means a rate of change in absorbance before and after the development
  • the residual layer ratio in an exposed area means a sustained rate of the absorbance value.
  • Table 4 The results are shown in Table 4.
  • Example 29 [0175] The same procedures were followed as in Example 29, except that the dye resist solution composition in Example 29 was changed as shown in the above Table 4. The results are shown in Table 5 including the results of Example 29.
  • Examples 36 to 42 the silicon wafer is used as the substrate, which was different from that in Examples 29 to 35. However, in all of Examples 29 to 42, the dye resist solution was applied over the subbing layer, whereby the same various performances were achieved without producing any substantial difference.
  • Example 29 [0178] The same procedures were repeated as in Example 29, except that the dye resist solution composition in Example 29 was changed as shown in the above Table 4. The results are shown in Table 5.
  • Example 29 The same procedures were carried out as in Example 29, except that the dye resist solution composition in Example 29 was changed as shown in Table 6. The results are shown in Table 6. TABLE 5 Developability Residual in an layer ratio in unexposed an exposed Dye Amine area area Example 29 Acid Yellow 42 100 99 Example 30 Acid Yellow 42 100 93 Example 31 Acid Yellow 42 100 91 Example 32 Acid Yellow 42 100 96 Example 33 Acid Yellow 42 100 96 Example 34 Acid Yellow 42 100 94 Comp. Acid Yellow 42 Ditolylguanidine 59 69 Example 18 Comp. Acid Yellow 42 Dehydroabiethylamine 56 64 Example 19 Example 35 Acid Blue 120 100 98 Comp. Acid Blue 120 Ditolylguanidine 66 68 Example 20
  • Example 22 Example Acid Red 143 765 Bis(2-methoxy- 133 1031 74 1.21 0.71 9.29 100 96 45 ethyl)amine Comp. Acid Red 143 765 Ditolylguanidine 239 1243 62 1.00 0.85 9.15 67 66
  • Example 23 Example Acid Yellow 582 Bis(2-methoxy- 133 715 81 1.15 0.74 9.26 100 99 46 172 ethyl)amine Comp.
  • Example 172 24 Example Acid Yellow 889 Bis(2-methoxy- 133 1155 77 1.18 0.72 9.28 100 100 47 228 ethyl)amine Comp.
  • Example 228 25 Example Acid Blue 80 635 Bis(2-methoxy- 133 901 70 1.24 0.69 9.31 100 99 48 ethyl)amine Comp.
  • Acid Blue 80 635 Ditolylguanidine 239 1113 57 1.00 0.85 9.15 59 71
  • Example 26 Example Acid Blue 23 532 Bis(2-methoxy- 133 796 67 1.27 0.67 9.33 100 99 49 ethyl)amine Comp.
  • Acid Blue 23 532 Ditolylguanidine 239 1010 53 1.00 0.85 9.15 63 69
  • Example 27 Example Acid Blue 25 394 Bis(2-methoxy- 133 527 75 1.20 0.71 9.29 100 96 50 ethyl)amine Comp.
  • Acid Blue 25 394 Ditolylguanidine 239 633 62 1.00 0.85 9.15 72 64
  • Example 28 Example Acid Blue 451 Bis(2-methoxy- 133 584 77 1.18 0.72 9.28 100 97 51 324:1 ethyl)amine Comp.
  • Example 324:1 29 Example Acid Yellow 687 Bis(2-methoxy- 133 820 84 1.13 0.75 9.25 100 98 52 38 ethyl)amine Comparative Acid Yellow 687 Ditolylguanidine 239 926 74 1.00 0.85 9.15 68 68
  • Example 38 30 Example Acid Yellow 591 Bis(2-methoxy- 133 724 82 1.18 0.72 9.28 100 96 53 65 ethyl)amine Comp.
  • Example 65 31 Example Acid Yellow 570 Bis(2-methoxy- 133 836 68 1.25 0.68 9.32 100 98 54 29 ethyl)amine Comp.
  • Acid Yellow 570 Ditolylguanidine 239 1048 54 1.00 0.85 9.15 64
  • Example 29 32 Example Acid Yellow 1118 Bis(2-methoxy- 133 1251 89 1.08 0.78 9.22 100 98 55 220 ethyl)amine Comp.
  • Example 1 The same procedures were carried out as in Example 1 to prepare a resist solution, from which a subbing layer was prepared on the glass substrate, to thereby produce a cured film.
  • the obtained resist solution was mixed with each of dye salts and dissolved at proportions as shown in Table 7 so as to produce the film having the same absorbance with respect to the same kind of the dyes used.
  • the dye resist was subjected to exposure and development (image formation) in the same manner as in Example 1.
  • image formation was confirmed by the conventional method through observation using an optical microscope and SEM photographs.
  • the relative absorbance intensity, developability in an unexposed area, and residual layer ratio in an exposed area were each measured using a chromoscope, MCPD-1000 (manufactured by OTSUKA ELECTRONICS CO., LTD.).
  • the developability in an unexposed area means a rate of change in absorbance before and after the development
  • the residual layer ratio in an exposed area means a sustained rate of the absorbance value.
  • Table 7 The results are shown in Table 7.
  • Example 57 The same procedures were performed as in Example 57, except that the dye resist solution composition in Example 57 was changed as shown in the above Table 7. The results are shown in Table 8 including the results of Example 57.
  • Examples 64 to 70 the silicon wafer was used as the substrate, which was different from the substrate used in Examples 57 to 63. However, in all of Examples 57 to 70, the dye resist solution was applied over the subbing layer, whereby the same various performances were obtained without producing any substantial difference.
  • Example 57 The same procedures were conducted as in Example 57 were followed, except that the dye resist solution composition in Example 57 was changed as shown in the above Table 7. The results are also shown in Table 8.
  • Example 57 Acid Yellow 42 Compound of Specific 100 99
  • Example 58 Acid Yellow 42 Compound of Specific 100 100
  • Example (4) Example 59 Acid Yellow 42 Compound of Specific 100 99
  • Example 60 Acid Yellow 42 Compound of Specific 100 98
  • Example (6) Example 61 Acid Yellow 42 Compound of Specific 100 98
  • Example (11) Example 62 Acid Yellow 42 Compound of Specific 100 97
  • Example 15) Comp. Acid Yellow 42 Ditolylguanidine 59 69
  • Example 35 Comp. Acid Yellow 42 Dehydroabiethylamine 56 64
  • Example 36 Example 63 Acid Blue 120 Compound of Specific 100 97
  • Example (20) Comp. Acid Blue 120 Ditolylguanidine 66 68
  • Example guanidine 45 Example Acid Blue 451 Compound of 255 706 64 0.96 0.87 9.13 100 98 78 324:1 Specific Example (1) Comp. Acid Blue 451 Ditolyl- 239 690 55 1.00 0.85 9.15 55 65
  • Example 324:1 guanidine 46 Example Acid Yellow 687 Compound of 255 942 73 0.98 0.86 9.14 100 99 79 38 Specific Example (1) Comp. Acid Yellow 687 Ditolyl- 239 926 74 1.00 0.85 9.15 67 67
  • Example 38 guanidine 47 Example Acid Yellow 591 Compound of 255 846 70 1.01 0.84 9.16 100 98 80 65 Specific Example (1) Comp.
  • Example 84 The same procedures were carried out as in Example 57, except that in Example 84, the compound of Specific Example (1) was replaced with the compound of Specific Example (22), the solution composition was changed to satisfy the molecular weight to that of the compound of Specific Example (22), and after the exposure and development, heat treatment was carried out at 160° C. for one minute. It was revealed that the developability in an unexposed area was 100, and the residual layer ratio in an exposed area was 98.
  • the present invention provides a dye-containing curable composition that exhibits high sensitivity, high transmittance, high resolving power and wide development latitude, is free from dye elution, deterioration by heat and deterioration by light, and has high productivity, since excellent polymerization can be achieved.
  • the invention also provides a color filter prepared using the dye-containing curable composition, and a process of preparing the color filter.

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US20080166494A1 (en) * 2005-02-16 2008-07-10 Price Peter E Method of Making Topographically Patterned Coatings
US20100110242A1 (en) * 2008-11-04 2010-05-06 Shahrokh Motallebi Anthraquinone dye containing material, composition including the same, camera including the same, and associated methods
US8999626B2 (en) 2011-08-04 2015-04-07 Lg Chem, Ltd. Polymer compound comprising dye and curable resin composition comprising same

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US20050186489A1 (en) * 2004-02-19 2005-08-25 Tomoko Komatsu Color filter materials, color filters, manufacturing method and image sensor
US20080138521A1 (en) * 2005-02-16 2008-06-12 Price Peter E Method of Making Morphologically Patterned Coatings
US20080166494A1 (en) * 2005-02-16 2008-07-10 Price Peter E Method of Making Topographically Patterned Coatings
US8182871B2 (en) * 2005-02-16 2012-05-22 3M Innovative Properties Company Method of making topographically patterned coatings
US8993059B2 (en) * 2005-02-16 2015-03-31 3M Innovative Properties, Company Method of making morphologically patterned coatings
US20100110242A1 (en) * 2008-11-04 2010-05-06 Shahrokh Motallebi Anthraquinone dye containing material, composition including the same, camera including the same, and associated methods
US8999626B2 (en) 2011-08-04 2015-04-07 Lg Chem, Ltd. Polymer compound comprising dye and curable resin composition comprising same

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US20060194128A1 (en) 2006-08-31
DE60306567T2 (de) 2007-07-05
DE60306567D1 (de) 2006-08-17
KR100629749B1 (ko) 2006-09-28
EP1348739B1 (de) 2006-07-05
EP1348739A2 (de) 2003-10-01
EP1348739A3 (de) 2004-03-17
ATE332339T1 (de) 2006-07-15
US7306884B2 (en) 2007-12-11

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