WO2018025417A1 - Composition de résine colorée, film coloré, substrat décoratif, et panneau tactile - Google Patents

Composition de résine colorée, film coloré, substrat décoratif, et panneau tactile Download PDF

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Publication number
WO2018025417A1
WO2018025417A1 PCT/JP2016/073176 JP2016073176W WO2018025417A1 WO 2018025417 A1 WO2018025417 A1 WO 2018025417A1 JP 2016073176 W JP2016073176 W JP 2016073176W WO 2018025417 A1 WO2018025417 A1 WO 2018025417A1
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Prior art keywords
resin composition
group
colored
acid
colored resin
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PCT/JP2016/073176
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English (en)
Japanese (ja)
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井上欣彦
相原涼介
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東レ株式会社
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Priority to PCT/JP2016/073176 priority Critical patent/WO2018025417A1/fr
Publication of WO2018025417A1 publication Critical patent/WO2018025417A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces

Definitions

  • the present invention relates to a colored fat composition, a colored film, a decorative substrate, and a touch panel.
  • a projected capacitive touch panel has an ITO (Indium Tin Oxide) film pattern formed in a screen region, and a metal wiring portion such as molybdenum is further formed in the periphery thereof. And in order to hide such a metal wiring part, the light shielding pattern of black or white is often formed inside the cover glass of the projected capacitive touch panel.
  • ITO Indium Tin Oxide
  • the touch panel system is an out-cell type in which a touch panel layer is formed between a cover glass and a liquid crystal panel, an on-cell type in which a touch panel layer is formed on the liquid crystal panel, and an in-cell type in which a touch panel layer is formed inside the liquid crystal panel. It is roughly divided into cell type and OGS (One Glass Solution) type that directly forms a touch panel layer on the cover glass, but it can be made thinner and lighter than the conventional out-cell type.
  • OGS One Glass Solution
  • the light shielding pattern is required to have high heat resistance, and further, the chemical resistance in the patterning process of the ITO electrode. was also required.
  • Patent Documents 2 and 3 A plurality of techniques for forming a black light-shielding pattern with excellent heat resistance and chemical resistance by photolithography using a photosensitive resin composition containing a cardo resin are known (Patent Documents 2 and 3). Heat resistance and the like were required. On the other hand, attempts have been made to obtain a composition in which a coloring material is dispersed in a polyimide resin in order to obtain a light-shielding pattern having more excellent heat resistance and chemical resistance (Patent Documents 4 and 5).
  • organic solvents that can dissolve the polyimide resin are limited to highly polar solvents such as N-methylpyrrolidone and ⁇ -butyrolactone, and in such highly polar solvents, coloring materials, particularly surface treatment or coating with resin are not possible. Dispersion stabilization of the organic pigment or carbon black formed is extremely difficult, and it has been regarded as a problem that the color characteristics and insulation properties of the formed light shielding pattern cannot be controlled.
  • the present invention achieves remarkable heat resistance by containing a polyimide resin having a specific structure, and at the same time, forms a highly reliable colored film by highly dispersing and stabilizing the coloring material.
  • An object of the present invention is to provide a colored resin composition that can be used.
  • the present invention has the following configuration.
  • (1) An alkali-soluble polyimide resin having a structural unit represented by the following general formula (1), (B) a colorant, (C) a polymer dispersant, and (D) an organic solvent.
  • a colored resin composition is provided.
  • R 1 represents a 4- to 10-valent organic group
  • R 2 represents a 2- to 8-valent organic group
  • R 3 and R 4 each independently represents a phenolic hydroxyl group, a sulfone group, Represents an acid group, a thiol group or a carboxyl group
  • p and q each independently represents an integer of 0 to 6, and the sum of p and q is 1 or more).
  • a decorative substrate comprising the colored film.
  • a touch panel comprising the decorative substrate.
  • An organic EL display device having the colored film on at least one of a planarization layer on the drive circuit and an insulating layer on the first electrode.
  • the colored resin composition of the present invention it is possible to form a colored film having remarkable heat resistance with improved reliability due to the highly dispersed and stable coloring material.
  • the colored resin composition of the present invention contains (A) an alkali-soluble polyimide resin having a specific structural unit, (B) a colorant, (C) a polymer dispersant, and (D) an organic solvent.
  • the colored resin composition of the present invention contains (A) an alkali-soluble polyimide resin having a structural unit represented by the following general formula (1).
  • the alkali-soluble polyimide resin is preferably one that dissolves within a predetermined time in an inorganic alkali such as potassium hydroxide and an organic alkali such as tetramethylammonium hydroxide (TMAH). Specifically, what dissolves within 2 minutes when the resin is immersed in a sufficient amount of 0.05% KOH aqueous solution or a sufficient amount of 2.38% TMAH aqueous solution at 23 ° C. is generally preferable.
  • TMAH tetramethylammonium hydroxide
  • alkali-soluble polyimide resin used in the present invention does not need to be completely imidized, and includes, for example, 10% or less not imidized.
  • R 1- (R 3 ) p represents a residue after the raw acid dianhydride has been imidized.
  • R 1 is a tetravalent to 10-valent organic group, and is preferably an organic group having 5 to 40 carbon atoms having an aromatic ring or a cyclic aliphatic group.
  • Examples of the acid dianhydride include the following, and those obtained by substituting 1 to 6 hydrogens of the aromatic ring or cycloaliphatic group with R 3 .
  • R 5 represents a single bond, an oxygen atom, a sulfur atom, CH 2 , C (CF 3 ) 2 , C (CH 3 ) 2 , SO 2 or diphenylcyclopentane
  • R 6 and R 7 each independently represent a hydrogen atom, a hydroxyl group or a thiol group.
  • R 1 is expressed in another form, benzene, biphenyl, diphenylalkane, benzophenone, diphenylsulfone, diphenyl ether, cycloalkane having 5 to 8 carbon atoms,
  • Is preferably a functional group having a skeleton as a skeleton.
  • the two acid anhydride groups preferably have bonds to different benzene rings.
  • R 2- (R 4 ) q represents a residue after the diamine has undergone imidation reaction
  • R 2 is a divalent to octavalent organic group, and is an aromatic ring or cyclic
  • An organic group having 5 to 40 carbon atoms and having an aliphatic group is preferable.
  • diamine examples include m-phenylenediamine, p-phenylenediamine, 1,4-bis (4-aminophenoxy) benzene, 1,3-bis (4-aminophenoxy) benzene, 1,3-bis (3- Aminophenoxy) benzene, bis [4- (4-aminophenoxy) phenyl] sulfone, bis [4- (4-aminophenoxy) phenyl] propane, bis [4- (4-aminophenoxy) phenyl] hexafluoropropane, bis [4- (3-aminophenoxy) phenyl] sulfone, 9,9-bis (4-aminophenyl) fluorene, 2,5-bis (aminomethyl) bicyclo [2.2.1] heptane, 2,6-bis (Aminomethyl) bicyclo [2.2.1] heptane, diaminodiphenyl ether, diaminodiphenyl s
  • R 5 represents a single bond, an oxygen atom, a sulfur atom, CH 2 , C (CF 3 ) 2 , C (CH 3 ) 2 , SO 2 or diphenylcyclopentane.
  • R 6 and R 7 each independently represents a hydrogen atom, a hydroxyl group or a thiol group.
  • R 2 is expressed in another form, benzene, biphenyl, fluorene, diphenylalkane, benzophenone, diphenylsulfone, diphenylether, diphenylthioether, cycloalkane having 5 to 8 carbon atoms, And compounds obtained by removing the amino group from the compounds of the general formulas (3) and (4), Is preferably a functional group having a skeleton as a skeleton. When this functional group has a plurality of benzene rings, the two amino groups preferably have bonds to different benzene rings.
  • the alkali-soluble polyimide resin having the structural unit represented by the general formula (1) has a polar group having an active hydrogen selected from the group consisting of a carboxyl group, a phenolic hydroxyl group, a sulfonic acid group and a thiol group at the main chain end. It is preferable to have.
  • Introduction of the polar group having active hydrogen into the main chain terminal can be achieved by using an end-capping agent having a polar group having active hydrogen. Examples of such end capping agents include monoamines, acid anhydrides, monocarboxylic acids, monoacid chloride compounds, and monoactive ester compounds.
  • Examples of the monoamine used as the end capping agent include the following. 5-amino-8-hydroxyquinoline, 1-hydroxy-7-aminonaphthalene, 1-hydroxy-6-aminonaphthalene, 1-hydroxy-5-aminonaphthalene, 1-hydroxy-4-aminonaphthalene, 2-hydroxy-7 -Aminonaphthalene, 2-hydroxy-6-aminonaphthalene, 2-hydroxy-5-aminonaphthalene, 1-carboxy-7-aminonaphthalene, 1-carboxy-6-aminonaphthalene, 1-carboxy-5-aminonaphthalene, 2 -Carboxy-7-aminonaphthalene, 2-carboxy-6-aminonaphthalene, 2-carboxy-5-aminonaphthalene, 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 4-aminosalicylic acid, 5 -Aminosalicylic acid, 6-aminosalicylic acid, 2-a
  • Examples of the acid anhydride, monocarboxylic acid, monoacid chloride compound, and monoactive ester compound used as the end-capping agent include the following.
  • Examples of the acid anhydride include acid anhydrides such as phthalic anhydride, maleic anhydride, nadic acid, cyclohexanedicarboxylic acid anhydride, and 3-hydroxyphthalic acid anhydride.
  • Monocarboxylic acids include 3-carboxyphenol, 4-carboxyphenol, 3-carboxythiophenol, 4-carboxythiophenol, 1-hydroxy-7-carboxynaphthalene, 1-hydroxy-6-carboxynaphthalene, 1-hydroxy-5 -Carboxynaphthalene, 1-mercapto-7-carboxynaphthalene, 1-mercapto-6-carboxynaphthalene, 1-mercapto-5-carboxynaphthalene, 3-carboxybenzenesulfonic acid, 4-carboxybenzenesulfonic acid and the like.
  • the monoacid chloride compound a compound obtained by converting the carboxyl group of the monocarboxylic acid into an acid chloride.
  • Monoacid chloride compounds include terephthalic acid, phthalic acid, maleic acid, cyclohexanedicarboxylic acid, 1,5-dicarboxynaphthalene, 1,6-dicarboxynaphthalene, 1,7-dicarboxynaphthalene or 2,6-dicarboxyl. Only one of the carboxyl groups of dicarboxylic acids such as naphthalene is converted to acid chloride.
  • the active ester compound is obtained by reacting the above monoacid chloride compound with N-hydroxybenzotriazole or N-hydroxy-5-norbornene-2,3-dicarboximide.
  • the proportion of monoamine used as the end-capping agent is preferably from 0.1 to 60 mol%, more preferably from 1 to 40 mol%, based on the total amine component.
  • the ratio of the acid anhydride, monocarboxylic acid, monoacid chloride compound or monoactive ester compound used as the end-capping agent is preferably from 0.1 to 100 mol%, more preferably from 5 to 90 mol%, based on the diamine component. .
  • R 2 or R 5 is a fat having a siloxane structure within a range that does not decrease the heat resistance. It may be a group substituent.
  • an alkali-soluble polyimide resin for example, an alkali-soluble polyimide containing 1 to 10 mol% of bis (3-aminopropyl) tetramethyldisiloxane or bis (p-amino-phenyl) octamethylpentasiloxane as a diamine component Resin.
  • alkali-soluble resins may be added besides the alkali-soluble polyimide resin represented by the general formula (1).
  • a polyimide resin, an acrylic resin, a siloxane resin, a cardo resin etc. are mentioned.
  • the proportion of the alkali-soluble polyimide resin represented by the general formula (1) in the alkali-soluble resin may be appropriately determined depending on desired heat resistance, dispersion stability and the like, but is preferably 10% by mass or more, and 50% by mass. The above is more preferable.
  • the following method is illustrated as a manufacturing method of alkali-soluble polyimide resin.
  • a step of obtaining a polyimide precursor by the following method.
  • (C) A method of reacting a tetracarboxylic dianhydride and an alcohol to obtain a diester compound, and then reacting the diester compound and a diamine (part of which is replaced with a monoamine compound) in the presence of a condensing agent. .
  • (D) A tetraester dianhydride and an alcohol are reacted to obtain a diester. Thereafter, the remaining dicarboxylic acid in the reaction product is acidified.
  • the process of obtaining a polyimide resin by the following method.
  • (A) A method in which the obtained polyimide precursor is completely imidized by a known method.
  • a method in which a tetracarboxylic dianhydride and a diisocyanate compound are reacted at a high temperature and a polyimide is produced by a decarboxylation reaction may be used.
  • the weight average molecular weight of the alkali-soluble polyimide resin is preferably from 5,000 to 100,000, preferably from 10,000 to 70,000, in order to improve the chemical resistance of the colored film obtained by curing the colored resin composition of the present invention and the solubility in an alkali developer. Is more preferable.
  • the colored resin composition of the present invention contains (B) a coloring material.
  • the colorant is an organic pigment, an inorganic pigment or a dye generally used in the field of electronic information materials.
  • an organic pigment or an inorganic pigment is preferable.
  • organic pigment examples include the following. Diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, polyazo; Phthalocyanine pigments such as copper phthalocyanine, copper halide phthalocyanine, metal-free phthalocyanine; Anthraquinone pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone; In addition, quinacridone pigments, dioxazine pigments, perinone pigments, perylene pigments, thioindigo pigments, isoindoline pigments, isoindolinone pigments, quinophthalone pigments, selenium pigments or metal complex pigments.
  • Diketopyrrolopyrrole pigments azo pigments such as azo, disazo, polyazo
  • Phthalocyanine pigments such as copper phthal
  • the inorganic pigment examples include the following. Titanium oxide, zinc oxide, zinc sulfide, lead white, calcium carbonate, precipitated barium sulfate, white carbon, alumina white, kaolin clay, talc, bentonite, black iron oxide, cadmium red, red bean, molybdenum red, molybdate orange, chromium Vermilion, yellow lead, cadmium yellow, yellow iron oxide, titanium yellow, chromium oxide, viridian, titanium cobalt green, cobalt green, cobalt chrome green, Victoria green, ultramarine, bitumen, cobalt blue, cerulean blue, cobalt silica blue, cobalt Zinc silica blue, manganese violet, cobalt violet.
  • the dye examples include azo dyes, anthraquinone dyes, condensed polycyclic aromatic carbonyl dyes, indigoid dyes, carbonium dyes, phthalocyanine dyes, methine dyes, and polymethine dyes.
  • red pigment examples include Pigment Red 9, 48, 97, 122, 123, 144, 149, 166, 168, 177, 179, 180, 192, 209, 215, 216, 217, 220, 223, and 224. 226, 227, 228, 240, and 254 (all numerical values are color indexes (hereinafter referred to as “CI” numbers)).
  • CI color indexes
  • orange pigment examples include Pigment Orange 13, 36, 38, 43, 51, 55, 59, 61, 64, 65, and 71.
  • yellow pigment examples include Pigment Yellow 12, 13, 17, 20, 24, 83, 86, 93, 95, 109, 110, 117, 125, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 168 and 185 (all numerical values are CI numbers).
  • purple pigments examples include Pigment Violet 19, 23, 29, 30, 32, 37, 40, and 50 (all numerical values are CI numbers).
  • Blue pigments include CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 22, 60, 64 (all numbers are CI numbers).
  • green pigment examples include Pigment Green 7, 10, 36, or 58 (all numerical values are CI numbers).
  • black pigments include black organic pigments, mixed color organic pigments, and inorganic pigments.
  • black organic pigments include carbon black, perylene black, aniline black, and benzofuranone pigments.
  • the mixed color organic pigment include those obtained by mixing two or more kinds of pigments having red, blue, green, purple, yellow, magenta, or cyan colors into a pseudo black color.
  • the inorganic pigment examples include the following. Graphite; Fine particles of metals such as titanium, copper, iron, manganese, cobalt, chromium, nickel, zinc, calcium, silver; oxides, composite oxides, sulfides, nitrides, and oxynitrides of the above metals. Among these, carbon black and titanium nitride having high light shielding properties are preferable.
  • white pigments include titanium dioxide, barium carbonate, zirconium oxide, calcium carbonate, barium sulfate, alumina white, and silicon dioxide.
  • Examples of the dye include the following. Direct Red 2, 4, 9, 23, 26, 28, 31, 39, 62, 63, 72, 75, 76, 79, 80, 81, 83, 84, 89, 92, 95, 111, 173, 184 207, 211, 212, 214, 218, 221, 223, 224, 225, 226, 227, 232, 233, 240, 241, 242, 243, 247; Acid Red 35, 42, 51, 52, 57, 62, 80, 82, 111, 114, 118, 119, 127, 128, 131, 143, 145, 151, 154, 157, 158, 211, 249, 254 257, 261, 263, 266, 289, 299, 301, 305, 319, 336, 337, 361, 396, 397; Reactive Red 3, 13, 17, 19, 21, 22, 23, 24, 29, 35, 37, 40, 41, 43, 45, 49, 55; Basic Red 12, 13, 14, 15, 18, 22, 23, 24, 25, 27,
  • the mass ratio of the colorant / resin component contained in the colorant resin composition of the present invention is preferably 90/10 to 20/80, and more preferably 90/10 to 40/60.
  • the resin component means a resin component in which an additive such as an alkali-soluble polyimide resin and a polymer dispersant, and a polymer compound further added depending on the case are combined. If the resin component is too small, the dispersion stability of the colorant may be insufficient. On the other hand, if the coloring material is too small, the coloring film formed by curing the colored resin composition of the present invention may be insufficiently colored.
  • the colored resin composition of the present invention contains (C) a polymer dispersant.
  • C a polymer dispersant.
  • the colorant can be uniformly and stably dispersed in the resin composition.
  • the polymer dispersant (C) include polyester polymer dispersants, acrylic polymer dispersants, polyurethane polymer dispersants, polyallylamine polymer dispersants, and carbodiimide dispersants.
  • the main chain is made of polyamine, polyether, polyester, polyurethane, poly (meth) acrylate, etc.
  • the side chain is amine, carboxylic acid, phosphoric acid, amine salt, carboxylate, phosphate, etc.
  • Polymers having a polar functional group include those having only an amine value, those having only an acid value, those having an amine value and an acid value, and those having neither an amine value nor an acid value.
  • the polymer dispersant of the present invention those having an amine value are preferable.
  • the polymer dispersant may have an acid value, but preferably has only an amine value without an acid value.
  • the amine value of the polymer dispersant is preferably 10 mgKOH / g or more and 100 mgKOH / g or less, more preferably 10 mgKOH / g or more and 60 mgKOH / g or less.
  • the amine value is low, the dispersion stabilizing effect tends to be difficult to obtain.
  • the amine value is high, the solubility of the photosensitive resin composition in an alkaline developer is lowered, and the pattern processability is deteriorated. Tend.
  • dispersant having only an amine value examples include the following. “DISPERBYK” (trade names) 102, 160, 161, 162, 2163, 164, 2164, 166, 167, 168, 2000, 2050, 2150, 2155, 9075, 9077; BYK-LP N6919, BYK-LP N21116 or BYK-LP N21234 (all of which are manufactured by Big Chemie); “EFKA” (trade name) 4015, 4020, 4046, 4047, 4050, 4055, 4060, 4080, 4300, 4330, 4340, 4400, 4401, 4402, 4403, 4800 (all are manufactured by BASF); “Ajisper” (registered trademark) PB711 (manufactured by Ajinomoto Fine Techno Co.); “SOLSPERSE” (registered trademark) 13240, 13940, 20000, 71000 or 76500 (all are manufactured by Lubrizol).
  • dispersants having only an amine value those having a basic functional group such as a tertiary amino group or a nitrogen-containing heterocycle such as pyridine, pyrimidine, pyrazine and isocyanurate are preferable.
  • a basic functional group such as a tertiary amino group or a nitrogen-containing heterocycle such as pyridine, pyrimidine, pyrazine and isocyanurate
  • examples of the polymer dispersant having a tertiary amino group or a nitrogen-containing heterocyclic basic functional group include the following. “DISPERBYK” 164,167, BYK-LP N6919; BYK-LP N21116; “SOLPERSE” 20000.
  • polymer dispersant having an amine value and an acid value examples include “DISPERBYK” (trade name) 142, 145, 2001, 2010, 2020, 2025 or 9076, Anti-Terra-205 (all of which are manufactured by Big Chemie). ), “Solspers” (registered trademark) 24000 (manufactured by Lubrizol), Azisper (registered trademark) PB821, PB880 or PB881 (all of which are manufactured by Ajinomoto Fine Techno) or “SOLPERSE” (registered trademark) 9000,11200, 13650, 24000SC, 24000GR, 32000, 32500, 32550, 326000, 33000, 34750, 35100, 35200, 37500, 39000 or 56000 (manufactured by Lubrizol).
  • the amount of the polymer dispersant is preferably as small as possible as a proportion of the resin component in order to improve dispersion stability while maintaining heat resistance, specifically, the total amount of the resin component. On the other hand, it is preferably 1 to 50% by mass, and more preferably 1 to 30% by mass. On the other hand, the total amount of the colorant is preferably 1 to 100% by mass, and more preferably 3 to 30% by mass.
  • a weight average molecular weight of the polymer dispersing agent 1000 or more and 100000 or less are preferable, and 3000 or more and 50000 or less are more preferable. When the molecular weight is low, a sufficient dispersion stabilizing effect cannot be obtained, and when the molecular weight is high, there is a problem that the solubility in an alkaline developer is lowered.
  • the colored resin composition of the present invention contains (D) an organic solvent.
  • organic solvents include ethers, acetates, esters, ketones, aromatic hydrocarbons, amides, and alcohol compounds.
  • Ethylene glycol monomethyl ether ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n- Butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, di Propylene glycol mono Chill ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, dipropylene glycol dimethyl ether, dipropylene
  • ester compounds can also be used.
  • Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone or 3-heptanone; Lactic acid alkyl esters such as methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate.
  • Aromatic hydrocarbons such as toluene and xylene.
  • Amides such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide.
  • Alcohols such as butyl alcohol, isobutyl alcohol, pentanol, 4-methyl-2-pentanol, 3-methyl-2-butanol, 3-methyl-3-methoxybutanol and diacetone alcohol;
  • the solubility parameter SP value of the organic solvent is preferably 7.5 or more and 10.0 or less, preferably 8.5 or more and 10.0 or less, and such a solvent is contained in the solvent in an amount of 50% by mass or more, and further 70% by mass or more. Preferably it is.
  • the SP value is low, the polymer dispersant and the alkali-soluble resin are difficult to dissolve and difficult to disperse, and when the SP value is high, the effect of dispersion stabilization by the polymer dispersant tends to be small.
  • the ratio of the compound of acetates in all (D) organic solvents contained in the colored resin composition of the present invention is preferably 50 to 100% by mass, more preferably 70 to 100% by mass.
  • the organic solvent (D) is preferably a mixture of two or more compounds.
  • the proportion of the organic solvent having a boiling point of 150 to 200 ° C. 30 to 75% by mass with respect to the organic solvent is preferable.
  • the ratio of the (D) organic solvent to the total solid content of the colored resin composition of the present invention is preferably 20 to 800 parts by mass and more preferably 30 to 500 parts by mass with respect to 100 parts by mass of the total solids.
  • Photosensitivity is imparted to the colored resin composition when the colored resin composition of the present invention contains (E) a photopolymerizable compound and (F) a photopolymerization initiator.
  • Examples of the photopolymerizable compound include a monomer or oligomer having a polyfunctional group or a monofunctional group.
  • the functional group is a polymerizable group, and a carbon-carbon double bond is preferable.
  • (Meth) acrylic acid compounds include bisphenol A diglycidyl ether (meth) acrylate, poly (meth) acrylate carbamate, modified bisphenol A epoxy (meth) acrylate, adipic acid 1,6-hexanediol (meth) acrylic acid ester, Phthalic anhydride propylene oxide (meth) acrylic acid ester, trimellitic acid diethylene glycol (meth) acrylic acid ester, rosin-modified epoxy di (meth) acrylate, alkyd-modified (meth) acrylate, full orange acrylate oligomer, tripropylene glycol di (meth) ) Acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, trimethylolpropane tri (meth) ) Acrylate, pentaerythr
  • polyfunctional group monomers By appropriately selecting and combining these polyfunctional group monomers, monofunctional group monomers, and oligomers, it is possible to adjust characteristics such as sensitivity or processability of the resulting photosensitive colored resin composition.
  • a compound having 3 or more polymerizable groups is preferable, and a compound having 5 or more polymerizable groups is more preferable. Dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate or an acid-modified product thereof is more preferable.
  • reaction product obtained by reacting a polybasic acid carboxylic acid or its acid anhydride with a reaction product of an epoxy compound having two glycidyl ether groups and methacrylic acid.
  • Saturated group-containing alkali-soluble monomers are also preferred.
  • the amount of the photopolymerizable compound is preferably 1 to 70% by mass and more preferably 20 to 50% by mass with respect to the total amount of the resin component.
  • the addition amount is small, sufficient photosensitive characteristics cannot be obtained and processing becomes difficult.
  • the addition amount is large, the cured shrinkage of the formed film increases, and the adhesion with the base material decreases due to the film stress. This is not preferable because wrinkles are generated in the film.
  • radical photopolymerization initiator an alkylphenone photopolymerization initiator or an oxime ester photopolymerization initiator is preferable.
  • alkylphenone photopolymerization initiator examples include ⁇ -aminoalkylphenone photopolymerization initiators and ⁇ -hydroxyalkylphenone photopolymerization initiators. In order to further increase sensitivity, ⁇ -aminoalkylphenone photopolymerization initiators are preferred.
  • Examples of ⁇ -aminoalkylphenone photopolymerization initiators include 2,2-diethoxyacetophenone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, “Irgacure” ( 2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone which is a registered trademark 369 and 2- (dimethylamino) -2-[(4- Methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] -1-butanone, 1-hydroxycyclohexyl phenyl ketone (both from BASF Corporation): and 2-hydroxy-2-methyl- 1-phenylpropan-1-one.
  • Irgacure 2-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butanone which is a registered trademark 369 and 2- (dimethylamino) -2-[(4
  • oxime ester photopolymerization initiator examples include “Irgacure” (registered trademark) OXE01, 1,2-octanedione, 1- [4- (phenylthio) -2- (O-benzoyloxime)] and “ “Irgacure” ® OXE02 ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime); and “ADEKA” (Registered Trademark) Optomer N-1818, N-1919 and “ADEKA ARKLES” NCI-831 (all of which are manufactured by ADEKA Corporation) can be mentioned.
  • Irgacure registered trademark
  • OXE01 1,2-octanedione
  • “Irgacure” ® OXE02 ethanone 1- [9
  • inorganic compounds such as benzophenone compounds, oxanthone compounds, imidazole compounds, benzothiazole compounds, benzoxazole compounds, carbazole compounds, triazine compounds and phosphorus compounds, and titanates
  • photoinitiator etc. together. The following are mentioned as such a photoinitiator.
  • Benzophenone N, N′-tetraethyl-4,4′-diaminobenzophenone, 4-methoxy-4′-dimethylaminobenzophenone, benzoin, benzoin methyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, ⁇ -hydroxyisobutylphenone, thioxanthone, 2-chlorothioxanthone, t-butylanthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone 1,2-benzoanthraquinone, 1,4-dimethylanthraquinone, 2-phenylanthraquinone, 2- (o-chlorophenyl)
  • the amount of the photopolymerization initiator is preferably 0.1 to 40% by mass with respect to the total amount of the resin components. When two or more kinds of photopolymerization initiators are mixed and used, the total amount is 0.2 to 60. Mass% is preferred.
  • the colored resin composition of the present invention preferably contains a thermally crosslinkable compound in order to improve the reliability and chemical resistance of a colored film formed by curing the colored resin composition of the present invention.
  • a thermally crosslinkable compound in order to improve the reliability and chemical resistance of a colored film formed by curing the colored resin composition of the present invention.
  • the heat crosslinkable compound having one heat crosslinkable group include the following. ML-26X, ML-24X, ML-236TMP, 4-methylol 3M6C, ML-MC or ML-TBC (all of which are manufactured by Honshu Chemical Industry Co., Ltd.) and Pa type benzoxazine (Shikoku Chemicals Co., Ltd.) )).
  • thermally crosslinkable compound having two thermally crosslinkable groups examples include the following. DM-BI25X-F, 46DMOC, 46DMOIPP or 46DMOEP (all of which are manufactured by Asahi Organic Materials Co., Ltd.); DML-MBPC, DML-MBOC, DML-OCHP, DML-PC, DML-PCHP, DML-PTBP, DML-34X, DML-EP, DML-POP, DML-OC, dimethylol-Bis-C, dimethylol-BisOC- P, DML-BisOC-Z, DML-BisOCHP-Z, DML-PFP, DML-PSBP, DML-MB25, DML-MTrisPC, DML-Bis25X-34XL or DML-Bis25X-PCHP (all of which are Honshu Chemical Industries ( Product)); Nicarax MX-290 (manufactured by Sanwa Chemical Co., Ltd.); Ba type benzoxazine or B
  • thermally crosslinkable compound having three thermally crosslinkable groups examples include the following. TriML-P, TriML-35XL or TriML-TrisCR-HAP (all of which are manufactured by Honshu Chemical Industry Co., Ltd.).
  • thermally crosslinkable compound having four thermally crosslinkable groups examples include the following. TM-BIP-A (Asahi Organic Materials Co., Ltd.); TML-BP, TML-HQ, TML-pp-BPF, TML-BPA or TMOM-BP (all of which are manufactured by Honshu Chemical Industry Co., Ltd.); “Nicarak” MX-280, “Nicarak” MX-270 (all of which are manufactured by Sanwa Chemical Co., Ltd.).
  • thermally crosslinkable compound having 6 thermally crosslinkable groups examples include the following. HML-TPPHBA, HML-TPHAP (all of which are manufactured by Honshu Chemical Industry Co., Ltd.); “Nikarak” MW-390, “Nikarak” MW-100LM (all of which are manufactured by Sanwa Chemical Co., Ltd.).
  • those having two or more heat-crosslinkable groups are preferable, and “Nicalac” MX-280 or “Nicalac” MX-270 or Ba type benzoxazine or Bm type benzoxazine which are alicyclic compounds. “Nicarac” MW-390 and “Nicarac” MW-100LM having 6 heat-crosslinkable groups are preferable.
  • the colored resin composition of the present invention can contain a compound having a phenolic hydroxyl group in order to control its alkali developability.
  • the compound which has a phenolic hydroxyl group here is distinguished from the polyamide shown by General formula (1).
  • Examples of the compound having a phenolic hydroxyl group include the following. Bis-Z, BisOC-Z, BisOPP-Z, BisP-CP, Bis26X-Z, BisOTBP-Z, BisOCHP-Z, BisOCR-CP, BisP-MZ, BisP-EZ, Bis26X-CP, BisP-PZ, BisP- IPZ, BisCR-IPZ, BisOCP-IPZ, BisOIPP-CP, Bis26X-IPZ, BisOTBP-CP, TekP-4HBPA (Tetrakis P-DO-BPA), TrisP-HAP, TrisP-PA, BisOFP-Z, BisRS-2P, BisPG-26X, BisRS-3P, BisOC-OCHP, BisPC-OCHP, Bis25X-OCHP, Bis26X-OCHP, BisOCHP-OC, Bis236T-OCHP, Methylenetris-FR-CR, ISRS-26X or BisRS-OCHP (manufactured by any Honshu Chemical Industry Co.); B
  • Bis-Z, BisP-EZ, TekP-4HBPA, TrisP-HAP, TrisP-PA, BisOCHP-Z, BisP-MZ, BisP-PZ, BisP-IPZ, BisOCP-IPZ, BisP-CP, BisRS-2P, BisRS -3P, BisP-OCHP, methylenetris-FR-CR, BisRS-26X, BIP-PC, BIR-PC, BIR-PTBP or BIR-BIPC-F are preferred.
  • Bis-Z, TekP-4HBPA, TrisP-HAP, TrisP-PA, BisRS-2P, BisRS-3P, BIR-PC, BIR-PTBP or BIR-BIPC-F are preferred.
  • the ratio of the compound having a phenolic hydroxyl group to the resin component is preferably 1 to 60 parts by mass and more preferably 3 to 50 parts by mass with respect to 100 parts by mass of the resin component.
  • the colored resin composition of the present invention may contain an adhesion improver in order to improve the adhesion between the colored film obtained by curing the colored resin composition of the present invention and the substrate.
  • an adhesion improving agent a silane coupling agent is preferable.
  • the silane coupling agent include a hydrocarbon group having a functional group such as a vinyl group, an epoxy group, a styryl group, a methacryloxy group, an acryloxy group, or an amino group, and a hydrolyzable group such as an alkoxyl group bonded to a silicon atom. Things. The following are mentioned.
  • the colored resin composition of the present invention may contain a surfactant in order to improve the coating property, the smoothness of the surface of the coating film, or prevent Benard cells.
  • the ratio of the surfactant to the pigment is preferably 0.001 to 10% by mass, and more preferably 0.01 to 1% by mass. Examples of the surfactant include the following.
  • Anionic surfactants such as ammonium lauryl sulfate and polyoxyethylene alkyl ether sulfate triethanolamine; Cationic surfactants such as stearylamine acetate and lauryltrimethylammonium chloride; Mainly amphoteric surfactants such as lauryl dimethylamine oxide and lauryl carboxymethylhydroxyethyl imidazolium betaine, nonionic surfactants such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether or sorbitan monostearate, and polydimethylsiloxane Examples of the silicone-based surfactant or fluorine-based surfactant used as a skeleton are listed.
  • Examples of the method for producing the colorant resin composition of the present invention include a method in which a colorant is dispersed in a solution of an alkali-soluble polyimide resin using a disperser.
  • Dispersers include ball mills, bead mills, sand grinders, three roll mills or high speed impact mills.
  • a bead mill is preferred for the purpose of improving dispersion efficiency and fine dispersion.
  • examples of the bead mill include a coball mill, a basket mill, a pin mill, and a dyno mill.
  • examples of beads of the bead mill include titania beads, zirconia beads, and zircon beads.
  • the bead diameter of the bead mill is preferably 0.01 to 5.0 mm, more preferably 0.03 to 1.0 mm. When the primary particle diameter of the coloring material and the secondary particles formed by agglomeration of the primary particles are small, fine beads of 0.03 to 0.10 mm are preferable.
  • a bead mill provided with a centrifugal separator capable of separating fine beads and dispersion liquid is preferable.
  • a coloring material containing coarse particles of about submicron is dispersed, a sufficient crushing force can be obtained, and thus beads having a size of 0.10 mm or more are preferable.
  • a photosensitive colored resin composition is applied onto a substrate to obtain a coating film.
  • the substrate include a transparent substrate such as soda glass, non-alkali glass, or quartz glass, a silicon wafer, a ceramic substrate, or a gallium arsenide substrate.
  • the method for applying the colored resin composition include spin coating using a spinner, spray coating die coating, and roll coating.
  • the thickness of the coating film may be appropriately determined depending on the coating method or the like, but it is general that the thickness after drying is 1 to 150 ⁇ m.
  • the obtained coating film is dried to obtain a dry film.
  • drying is performed at 50 to 150 ° C. for 1 minute to several hours (for example, 5 hours) by heat drying using an oven or a hot plate, air drying, reduced pressure drying, or infrared irradiation.
  • the obtained dried film is irradiated with actinic radiation through a mask having a desired pattern and exposed to obtain an exposed film.
  • actinic radiation to be irradiated include ultraviolet rays, visible rays, electron beams, and X-rays.
  • the colored resin composition of the present invention is preferably irradiated with i-line (365 nm), h-line (405 nm) or g-line (436 nm) of a mercury lamp.
  • the obtained exposed film is developed with an alkaline developer or the like to remove unexposed portions, and a pattern is obtained.
  • alkaline developer aqueous solutions of the following alkaline compounds can be used.
  • Inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia;
  • Primary amines such as ethylamine and n-propylamine; Secondary amines such as diethylamine and di-n-propylamine; Tertiary amines such as triethylamine and methyldiethylamine; Tetraalkylammonium hydroxides such as tetramethylammonium hydroxide (TMAH); Quaternary ammonium salts such as choline;
  • Alcohol amines such as triethanolamine, diethanolamine, monoethanolamine, dimethylaminoethanol, diethylaminoethanol; Cyclic amines such as pyrrol
  • the concentration of the alkaline compound in the alkaline developer is generally from 0.01 to 50% by mass, preferably from 0.02 to 10% by mass, and more preferably from 0.02 to 1% by mass.
  • a surfactant such as a nonionic surfactant may be added in an amount of 0.1 to 5% by mass.
  • a water-soluble organic solvent such as ethanol, ⁇ -butyrolactone, dimethylformamide, or N-methyl-2-pyrrolidone may be added to the developer.
  • Developing methods include dipping, spraying, and paddle methods.
  • the obtained pattern may be rinsed with pure water or the like.
  • a patterned colored film can be obtained by heat-treating (post-baking) the obtained pattern. This heat treatment is generally carried out continuously or stepwise at 150 to 300 ° C. for 0.25 to 5 hours in an air or nitrogen atmosphere or in a vacuum state.
  • those containing a black colorant are added to a light shielding image such as a black matrix of a color filter provided in a liquid crystal display device, a colored partition inside an organic EL display, or a touch panel. It can utilize suitably for formation of the colored film of a decoration board
  • the substrate on which the TFT is formed, the planarizing layer on the driving circuit, the insulating layer on the first electrode, and It can be suitably used as a planarization layer or an insulating layer of a display device having display elements in this order.
  • a display device having such a configuration a liquid crystal display device, an organic EL display device, and the like can be given. More preferable in an organic EL display device that requires higher heat resistance and low outgassing property for a planarization layer and an insulating layer. Can be used.
  • Example 1 175 g of carbon black (TPK1227; manufactured by Cabot), 57.5 g of polyimide resin (P-1), 33.7 g of DISPERBYK-167 and 733.8 g of propylene glycol monomethyl ether acetate, the surface of which was modified with sulfonic acid groups (Hereinafter “PGMEA”) were mixed and stirred for 20 minutes with a homomixer (manufactured by Primex) to obtain a preliminary dispersion.
  • TPK1227 manufactured by Cabot
  • P-1 polyimide resin
  • DISPERBYK-167 DISPERBYK-167
  • 733.8 g of propylene glycol monomethyl ether acetate the surface of which was modified with sulfonic acid groups
  • the polymer agent DISPERBYK-167 has an amine value of mgKOH / g, no acid value, and has an isocyanurate ring as a pigment adsorbing group.
  • the SP value of PGMEA is 8.7.
  • the obtained black resin composition 1 was applied onto an alkali-free glass substrate (AN100) with a spinner (1H-DS; manufactured by Mikasa Co., Ltd.), and the coating film was pre-baked at 100 ° C. for 2 minutes, and then at 230 ° C. After baking for 30 minutes, a black film 1 having a film thickness of 1.0 ⁇ m was formed. The black film 1 was subjected to the following evaluations. The results are shown in Table 1.
  • the weight loss rate (%) was measured using a sample obtained by scraping about 10 mg of the black film 1. More specifically, using a thermogravimetric measuring device (TGA-50; manufactured by Shimadzu Corporation), the temperature reaches 300 ° C. at a rate of 10 ° C./min while purging nitrogen gas at 50 mL / min. And measure the mass of the sample when it reaches 300 ° C. and the mass of the sample when it is held at 300 ° C. for 30 minutes, and calculate the heating loss rate (%) from these values. did.
  • TGA-50 thermogravimetric measuring device
  • the polymer dispersant BYK-LP N6919 has an amine value of 72 mgKOH / g, no acid value, and has a tertiary amine as a pigment adsorbing group.
  • a black resin composition 2 was obtained in the same manner as in Example 1 except that the carbon black dispersion (Bk-2) was used. Evaluation similar to Example 1 was performed using the obtained black resin composition 2. The results are shown in Table 1.
  • the polymeric dispersant BYK-LP N21116 has an amine value of 32 mgKOH / g, no acid value, and has a tertiary amine and a quaternary ammonium salt as a pigment adsorbing group.
  • a black resin composition 3 was obtained in the same manner as in Example 1 except that the carbon black dispersion (Bk-3) was used. Evaluation similar to Example 1 was performed using the obtained black resin composition 3. The results are shown in Table 1.
  • Example 4 The solid content concentration was 25% by mass in the same manner as in Example 1 except that 38.1 g of “Disperbic” BYK-2001 was used instead of “Disperbic” BYK-167, and the mass of PGMEA was changed to 729.4 g. A carbon black dispersion (Bk-4) having a colorant / resin component (mass ratio) of 70/30 was obtained.
  • the polymer dispersant “DISPERBIC” BYK-2001 has an amine value of 29 mgKOH / g, an acid value of 19 mg / KOH, and has a quaternary ammonium salt as a pigment adsorbing group.
  • a black resin composition 4 was obtained in the same manner as in Example 1 except that the carbon black dispersion (Bk-4) was used. Evaluation similar to Example 1 was performed using the obtained black resin composition 4. The results are shown in Table 1.
  • Example 5 Organic black “Irgaphor” Black S0100CF (BASF) 150.0 g, polyimide resin (P-1) 75.0 g, “SOLPERSE” 20000 (Lubrisol) 25.0 g, and 3-methoxybutyl acetate (hereinafter “ MBA ”) Organic black dispersion (Bk-5) having a solid concentration of 25% by mass and a colorant / resin component (mass ratio) of 60/40, except that 750 g was mixed.
  • the amine value of the polymer dispersant “SOLPERSE” 20000 is 29 mg KOH / g, no acid value, and has a tertiary amine as a pigment adsorbing group.
  • the SP value of MBA is 8.7.
  • Example 1 A carbon black dispersion was obtained in the same manner as in Example 1 except that the mass of the polyimide resin (P-1) was 91.2 g and the polymer dispersant (“DISPERBYK” -167) was not added. However, carbon black aggregated during dispersion using an ultra apex mill and the viscosity increased excessively, so that a carbon black dispersion could not be obtained.
  • a black resin composition 8 was obtained in the same manner as in Example 1 except that the carbon black dispersion (Bk-8) was used. Evaluation similar to Example 1 was performed using the obtained black resin composition 8. The results are shown in Table 1.
  • a black resin composition 9 was obtained in the same manner as in Example 1 except that the carbon black dispersion (Bk-9) was used. Evaluation similar to Example 1 was performed using the obtained black resin composition 9. The results are shown in Table 1.
  • Example 6 499.5 g of the carbon black dispersion (Bk-1), 19.2 g of the polyimide resin (P-1), 47.9 g of dipentaerythritol hexaacrylate, and 5.8 g of “ADEKA” which is a radical photopolymerization initiator.
  • Cruise “NCI-831 manufactured by ADEKA Corporation
  • 2.0 KBM503 manufactured by Shin-Etsu Chemical Co., Ltd.
  • 2.0 g of BYK333 dissolved in 425.4 g of PGMEA were added.
  • a photosensitive black resin composition 10 having a solid content concentration of 20% by mass and a pigment / resin (mass ratio) of 45/55 was obtained.
  • the obtained photosensitive black resin composition 10 was applied onto an alkali-free glass substrate with a spinner, and the coating film was dried at 100 ° C. for 2 minutes, and then mask aligner PEM-6M (manufactured by Union Optics Co., Ltd.). Was exposed through a photomask (200 mJ / cm 2 ). This was developed using a 0.045 mass% KOH aqueous solution, subsequently washed with pure water, and post-baked at 230 ° C. for 30 minutes to form a black film 10 having a thickness of 1.0 ⁇ m. The black film 10 was evaluated in the same manner as in Example 1. The results are shown in Table 1.
  • the black composition described in the Examples and the black film formed by curing 10 are excellent in light-shielding properties, insulation properties, and surface smoothness (surface roughness), and the dispersion state of the pigment in the composition is It can be seen that it was very good. Furthermore, it can be seen that the heating weight loss rate (%) is very low, degassing from the coating film is extremely small, and a colored film having excellent heat resistance is formed.
  • the colored resin composition of the present invention can be suitably used for forming a colored film of a decorative substrate provided in a touch panel and a colored insulating layer of an organic EL display device.

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Abstract

L'invention fournit une composition de résine colorée qui tout en parvenant à une résistance thermique notable du fait qu'elle comprend une résine polyimide possédant une structure spécifique, permet de former un film coloré d'une excellente fiabilité en raison de la stabilisation à un haut niveau de la dispersion d'un matériau coloré. La composition de résine colorée de l'invention comprend (A) une résine polyimide soluble dans les alcalis possédant une unité structurale contenant un groupe hydroxyle phénolique, un groupe sulfonate ou un groupe thiol, (B) le matériau coloré, (C) un agent de dispersion polymérique, et (D) un solvant organique. Une couche colorée à motifs obtenue à partir de la composition de l'invention, se révèle avantageuse dans un substrat décoratif, un panneau tactile, un dispositif d'affichage électroluminescent El organique, ou similaire.
PCT/JP2016/073176 2016-08-05 2016-08-05 Composition de résine colorée, film coloré, substrat décoratif, et panneau tactile WO2018025417A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0943413A (ja) * 1995-07-27 1997-02-14 Toyobo Co Ltd カラーフィルター及びその製造方法
JPH1060274A (ja) * 1996-08-13 1998-03-03 Toray Ind Inc ポリイミド系樹脂組成物、カラーフィルタおよび液晶表示素子
JP2003119381A (ja) * 2001-10-17 2003-04-23 Hitachi Cable Ltd 黒色ポリイミド組成物及びブラックマトリックス
JP2013197441A (ja) * 2012-03-22 2013-09-30 Toray Ind Inc 硬化物層付き回路基板の製造方法
JP2015114588A (ja) * 2013-12-13 2015-06-22 東洋インキＳｃホールディングス株式会社 光散乱層用樹脂組成物、光散乱層、および有機エレクトロルミネッセンス装置
JP2016138264A (ja) * 2015-01-23 2016-08-04 Jnc株式会社 熱硬化性樹脂組成物、硬化膜、硬化膜付き基板および電子部品

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0943413A (ja) * 1995-07-27 1997-02-14 Toyobo Co Ltd カラーフィルター及びその製造方法
JPH1060274A (ja) * 1996-08-13 1998-03-03 Toray Ind Inc ポリイミド系樹脂組成物、カラーフィルタおよび液晶表示素子
JP2003119381A (ja) * 2001-10-17 2003-04-23 Hitachi Cable Ltd 黒色ポリイミド組成物及びブラックマトリックス
JP2013197441A (ja) * 2012-03-22 2013-09-30 Toray Ind Inc 硬化物層付き回路基板の製造方法
JP2015114588A (ja) * 2013-12-13 2015-06-22 東洋インキＳｃホールディングス株式会社 光散乱層用樹脂組成物、光散乱層、および有機エレクトロルミネッセンス装置
JP2016138264A (ja) * 2015-01-23 2016-08-04 Jnc株式会社 熱硬化性樹脂組成物、硬化膜、硬化膜付き基板および電子部品

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