WO2015015961A1 - カラーフィルタ用顔料組成物及びカラーフィルタ - Google Patents
カラーフィルタ用顔料組成物及びカラーフィルタ Download PDFInfo
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- WO2015015961A1 WO2015015961A1 PCT/JP2014/066976 JP2014066976W WO2015015961A1 WO 2015015961 A1 WO2015015961 A1 WO 2015015961A1 JP 2014066976 W JP2014066976 W JP 2014066976W WO 2015015961 A1 WO2015015961 A1 WO 2015015961A1
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- color filter
- pigment
- organic
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- organic pigment
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- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
Definitions
- the present invention is a color filter pigment composition for forming a color filter of a color liquid crystal display device, and a color filter, and is miniaturized together with a specific organic dye derivative to achieve both miniaturization and dispersion stability.
- the present invention relates to a pigment composition for a color filter that has a higher light-shielding property than a conventional one and a color filter using the same.
- a liquid crystal panel incorporating a color filter on array (COA) in which a color filter substrate and a TFT array substrate are integrated is attracting attention.
- COA color filter on array
- the use of the COA eliminates the need for precise alignment performed when the above two substrates are used, and allows the red, blue, and green pixels of the color filter to be miniaturized to the limit. High definition panel can be achieved.
- Such a resin black matrix for COA is required to have a thick film because it requires a high light-shielding property.
- the difference in crosslink density in the film thickness direction at the exposed part increases, making it difficult to achieve high sensitivity and obtain a well-shaped black pattern.
- attempts have been made to use a large amount of light shielding material but when a conductive material such as carbon is used as the light shielding material, the relative permittivity of the black matrix increases and the volume resistance increases. There is a problem that the reliability of the display device is lowered due to the decrease.
- Patent Document 1 although there is a description of a light-shielding photosensitive resin composition containing a specific organic pigment for a resin black matrix that defines the maximum light transmittance in a specific wavelength range, it is compared with carbon black. The light shielding property was insufficient.
- Patent Document 2 among organic pigments having light transmittance in the visible light region, a combination of a yellow pigment, a blue pigment, and a purple pigment, or a pseudo blackened mixed color organic material composed of a combination of a yellow pigment, a red pigment, and a blue pigment.
- the optical density (OD) is low and the light shielding property is not sufficient.
- Patent Document 3 proposes a black matrix pigment composition containing blue, yellow, and red organic pigments having a particle size equal to or less than a specific specific surface area. The light shielding property is not obtained. As described above, some inventions have been proposed by mixing pigments. However, it is difficult to obtain a color filter including a black matrix of a color filter that has high insulation, low dielectric constant, and high optical density. There was a problem.
- the problem to be solved by the present invention is to provide an organic pigment composition for a color filter that is fine and has good dispersion stability and a high optical density, and a color filter containing them.
- the inventors of the present invention have a high dispersion stability even with fine particles by refining an organic pigment derivative having a specific chemical structure and an organic dye derivative containing a phthalimide group.
- the inventors have found that it is possible to obtain a color filter with high light shielding properties, and have completed the present invention.
- the present invention contains 1 to 15 parts of an organic dye derivative containing a phthalimidoalkyl group per 100 parts of an organic pigment having a chemical structure of the following general formula (1) and general formula (2), and the primary particle diameter of the pigment is 20 nm.
- an organic pigment composition for a color filter characterized by having a thickness of ⁇ 100 nm.
- R1 to R3 are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms.
- the organic pigment is C.I. I.
- an organic pigment composition for a color filter which is an orange pigment selected from at least one of CI Pigment Orange 36, 60, 62, 64 and 72.
- the present invention also provides an organic pigment composition for a color filter, wherein the organic pigment derivative is an organic pigment derivative selected from at least one of phthalimidoalkylated quinacridone or phthalimidoalkylated phthalocyanine.
- the present invention provides a color filter comprising the organic pigment composition for a color filter described above.
- the black matrix composed of other organic pigment compositions such as blue and red used in combination with the organic pigment composition for a color filter of the present invention is excellent in dispersion stability and excellent in light-shielding properties with a high OD value. Play.
- the pigment composition for a color filter of the present invention can form fine particles by performing solvent salt milling of an organic pigment having a specific chemical structure and a specific organic dye derivative, such as blue, yellow, and red.
- the organic pigment composition for black color filter is comprised by using together these organic pigments.
- the resulting black matrix containing the black organic pigment composition for a color filter has excellent dispersion stability and excellent light shielding properties with a high OD value.
- the organic pigment has a chemical structure represented by the following general formula (1) and general formula (2).
- R1 to R3 are each a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 1 to 5 carbon atoms.
- the organic pigment having the above chemical structure is an organic pigment having an orange hue having a benzimidazolone group and an azo group.
- I. Pigment Orange 36, 60, 62, 64, 72 can be mentioned.
- Each organic pigment can be used alone or in combination, and is selected from at least one of the above organic pigments.
- the organic dye derivative used in the present invention may have any chemical structure as long as it is an organic dye derivative having a phthalimide group.
- An organic dye derivative having a phthalimide group is often used in an organic pigment miniaturization step, and the action of making the main organic pigment fine is a known fact. Since the main organic pigment used in the present invention has an orange hue, organic dye derivatives of the same color are preferable, but organic dye derivatives having different hues can be used.
- Specific examples include an azo structure, a benzimidazolone structure, a quinacridone structure, a diketopyrrolopyrrole structure, a phthalocyanine structure, and a dioxazine violet structure. Among them, phthalimidoalkylated quinacridone and phthalimidoalkylated phthalocyanine are preferable.
- Organic pigment derivative is contained in the range of 1 to 20 parts per 100 parts of organic pigment. In consideration of hue and productivity, it is preferably contained in the range of 1 to 15 parts.
- the timing of adding the organic dye may be added in the step of refining the organic pigment carried out in the present invention, or may be added after washing and refining the organic pigment after the step of refining. However, in consideration of miniaturization and dispersion stability due to the organic dye derivative having a phthalimide group, it is preferable that the organic pigment is uniformly mixed in the miniaturization step.
- various additives may be added in addition to the organic dye derivative. Specific examples include light or thermosetting resins, surfactants, dispersants, rosins, and the like.
- the primary particle size of the refined organic pigment is preferably 20 to 150 nm, and more preferably 20 to 100 nm in order to impart high light shielding properties. It has been found that when the primary particle size of the pigment exceeds 150 nm, the dispersion stability is deteriorated, and as a result, light scattering tends to occur.
- the primary particle size of the organic pigment in the present invention is that an organic pigment composition is dispersed in a solvent such as cyclohexanone, the dispersion is applied on a colloid film, and an image of a scanning electron microscope (TEM) is taken. The size of 1000 particles of the obtained photographed image was measured, and the average value was taken as the primary particle diameter of the organic pigment.
- a solvent such as cyclohexanone
- Such organic pigments finer than conventional ones can be broadly classified by a pulverization method such as dry pulverization or wet pulverization.
- Solvent salt milling which is kneaded for a long time due to a high inorganic salt ratio, is suitable. This is a useful production method that can achieve both uniformity of particles and reduction in size.
- the ground mixture treated by solvent salt milling is subjected to washing, purification, and drying steps to become the organic pigment composition of the present invention.
- This solvent salt milling means kneading an organic pigment, a water-soluble inorganic salt and a hydrophilic organic solvent. Specifically, an organic pigment, a water-soluble inorganic salt, and a hydrophilic organic solvent that does not dissolve the organic pigment are charged into a kneader, and kneading and grinding are performed therein. When the conversion of the crystal form is intended in the kneading, a crude pigment having a crystal form different from that after the kneading can be used as the raw material for the kneading.
- the water-soluble inorganic salt it is preferable to use an inorganic salt such as sodium chloride, potassium chloride or sodium sulfate. It is more preferable to use an inorganic salt having an average particle size of 0.5 to 50 ⁇ m. Such an inorganic salt can be easily obtained by pulverizing a normal inorganic salt.
- the amount of the inorganic salt used is preferably 8 to 20 parts by weight, more preferably 10 to 15 parts by weight with respect to 1 part by weight of the organic pigment.
- water-soluble organic solvent those capable of suppressing crystal growth can be suitably used.
- the amount of the water-soluble organic solvent used is not particularly limited, but is preferably 0.01 to 5 parts by weight with respect to 1 part by weight of the organic pigment.
- the kneading temperature is preferably 30 to 150 ° C.
- the above temperature is particularly preferably in the range of 80 to 100 ° C. from the viewpoint of adjusting the fineness and crystallinity.
- a kneader As an apparatus used for this kneading, there is a kneader, a mix muller, Trimix (trade name) manufactured by Inoue Seisakusho, which is a planetary mixer described in JP-A-2007-100008, and JP-A-4-122778.
- Trimix trade name
- the continuous twin-screw extruder described above, Miracle KCK manufactured by Asada Tekko Co., Ltd. which is a continuous single-screw kneader described in JP-A-2006-306996, and the like can be used.
- the pigment composition for a color filter of the present invention may contain a free metal and a free metal ion source, but it is preferable that the amount is as small as possible.
- a free metal and free metal ion source can be washed with acids as described in JP-A-2008-308605.
- acids used include hydrochloric acid and sulfuric acid, and the concentration of hydrochloric acid and sulfuric acid is preferably 0.5% to 4%.
- the temperature during washing is preferably 50 to 90 ° C. Moreover, you may wash
- a blue organic pigment, a yellow organic pigment, and a red organic pigment can be used together to provide light shielding properties.
- These color organic pigments include, for example, organic pigments such as azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, indanthrene, and perylene based on the chemical structure. Can be mentioned. Hereinafter, specific examples of pigments that can be used in the present invention are indicated by pigment numbers.
- blue organic pigments examples include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like. Of these, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, and more preferably C.I. I. Pigment blue 15: 6.
- yellow organic pigments examples include C.I. I. Pigment Yellow 1, 1: 1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62: 1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127: 1, 128, 129, 133, 134, 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 17 174, 175, 176, 180, 181, 182, 183,
- red organic pigments examples include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 49: 2, 50: 1, 52: 1, 52: 2, 53, 53: 1, 53: 2, 53: 3, 57, 57: 1, 57: 2, 58: 4, 60, 63, 63: 1, 63: 2, 64, 64: 1, 68, 69, 81, 81: 1, 81: 2, 81: 3, 81: 4, 83, 88, 90: 1, 101, 101: 1, 104, 108, 108: 1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 17 , 181, 185, 187, 188, 190, 193, 194,
- C.I. I. Pigment Red 48 1, 122, 168, 177, 202, 206, 207, 209, 224, 242, 254, and more preferably C.I. I. Pigment red 177, 209, 224, 254.
- a blue organic pigment, a yellow organic pigment, and a red organic pigment can be used in combination, but if necessary, a green organic pigment, a purple organic pigment, an orange organic pigment, a brown organic pigment, etc. You may adjust the color tone.
- these other color organic pigments used in combination those having an average primary particle diameter of 20 to 100 nm are preferably used.
- organic pigments other than blue, yellow, and red suitable for use in combination C.I. I. Pigment green 7, 36, 58, C.I. I. Pigment orange 38, 71, C.I. I. And CI Pigment Violet 23.
- the organic pigment used and the combination thereof may be obtained as long as the blackness required for the target black matrix can be obtained.
- Making black by subtractively mixing the three primary colors of blue, yellow, and red belongs to the technical common sense of those skilled in the art, and the mixing ratio thereof is not particularly limited. However, for example, when the total of each color organic pigment of blue, yellow, and red is 100% in terms of mass, each color is centered on 33% by mass, and each color is increased or decreased by plus or minus 7%. The black color can be adjusted.
- the organic pigment composition for color filter of the present invention the pigment composition for black matrix containing the blue organic pigment, and the red organic pigment can be easily prepared by mixing them in an arbitrary order.
- the colored composition of the present invention contains the above-described organic pigment compositions of each color, a resin dispersant and an organic solvent.
- a colored composition in which each color organic pigment, organic solvent and dispersant are dispersed may be mixed separately, or all organic pigments may be dispersed with the organic solvent and dispersant at once. good.
- a resin dispersant is used in combination for improving dispersibility and dispersion stability.
- This resin-based dispersant has a function of binding the organic pigment and the anchor site, and the compatible part extends into the dispersion medium to form a dispersion.
- An alkali used for the preparation of the photosensitive composition described later is used.
- the soluble resin and the photopolymerizable monomer are different types.
- the resin dispersant examples include those having a polymer chain, such as polyurethane resin, polyethyleneimine, polyoxyethylene glycol diester, acrylic resin, polyester resin, and the like.
- polyester resin dispersants and / or acrylic resin dispersants are preferable in terms of dispersibility, heat resistance, and light resistance.
- resin-based dispersants include trade names such as Ajisper (manufactured by Ajinomoto Fine-Techno Co., Ltd.), EFKA (manufactured by Ciba), Disperbik (manufactured by Big Chemie), Disparon (manufactured by Enomoto Kasei), SOLPERSE. (Manufactured by Lubrizol), KP (manufactured by Shin-Etsu Chemical Co., Ltd.), polyflow (manufactured by Kyoeisha Chemical Co., Ltd.) and the like.
- 1 type may be used for these dispersing agents, and 2 or more types can be used together by arbitrary combinations and a ratio.
- the resin-based dispersant is usually 30 to 60 parts, preferably 38 to 50 parts, per 100 parts in terms of the total mass of the organic pigments of each color.
- An organic solvent is used for the preparation of the coloring composition.
- the organic solvent used here include diisopropyl ether, mineral spirit, n-pentane, amyl ether, ethyl caprylate, n-hexane, diethyl ether, isoprene, ethyl isobutyl ether, butyl stearate, n-octane, and valsol.
- Apco # 18 solvent diisobutylene, amyl acetate, butyl acetate, apcocinner, butyl ether, diisobutyl ketone, methylcyclohexene, methyl nonyl ketone, propyl ether, dodecane, soak solvent no. 1 and no.
- At least n-amyl methyl ketone (2-heptanone) is preferably used as the organic solvent contained in the coloring composition.
- one organic solvent may be used alone, or two or more organic solvents may be used in any combination and ratio.
- the organic solvent is preferably used in an amount of usually 300 to 800 parts, preferably 400 to 600 parts, per 100 parts in terms of the total mass of the organic pigments of each color.
- various pigment derivatives can be used in combination as required.
- the substituent of the pigment derivative include a sulfonic acid group, a sulfonamide group and a quaternary salt thereof, a phthalimidomethyl group, a dialkylaminoalkyl group, a hydroxyl group, a carboxyl group, and an amide group directly on the pigment skeleton or an alkyl group and an aryl group. And those bonded via a heterocyclic group or the like.
- the coloring composition can be prepared by stirring and mixing the organic pigment composition of each color described above, the resin dispersant, and the organic solvent. If necessary, it can be prepared by shaking for a required time in the presence of various grinding media such as beads and rods and dispersing the media by filtration or the like.
- the coloring composition can be used for forming the black matrix portion by a conventionally known method.
- a typical production method of a color filter is a photolithography method, and a black matrix is prepared by applying a photosensitive composition described later prepared from the coloring composition of the present invention onto a transparent substrate for a color filter and heating. After drying (pre-baking), pattern exposure is performed by irradiating ultraviolet rays through a photomask to cure the photo-curable compound at the location corresponding to the black matrix portion, and then developing the unexposed portion with a developer. The non-pixel portion is removed and the pixel portion is fixed to the transparent substrate. By this method, a black matrix portion made of a cured colored film of the photosensitive composition is formed on the transparent substrate.
- Each of the RGB pixel portions can also be prepared in the same manner as described above from a photosensitive composition prepared from each color organic pigment having a larger specific surface area.
- Examples of a method for applying a photosensitive composition described later on a transparent substrate such as glass include a spin coating method, a roll coating method, a slit coating method, and an inkjet method.
- the drying condition of the coating film of the photosensitive composition applied to the transparent substrate is usually about 50 to 150 ° C. for about 1 to 15 minutes, although it depends on the kind of each component, the blending ratio, and the like. This heat treatment is generally referred to as “pre-baking”.
- pre-baking This heat treatment is generally referred to as “pre-baking”.
- light used for photocuring the photosensitive composition it is preferable to use ultraviolet rays or visible light having a wavelength range of 200 to 500 nm. Various light sources that emit light in this wavelength range can be used.
- Examples of the developing method include a liquid filling method, a dipping method, and a spray method.
- the transparent substrate on which the black matrix or the pixel portion of the necessary color is formed is washed with water and dried.
- the color filter thus obtained is subjected to a heat treatment (post-baking) at 100 to 280 ° C. for a predetermined time with a heating device such as a hot plate or an oven to remove volatile components in the colored coating film, and at the same time,
- the unreacted photocurable compound remaining in the cured colored film of the curable composition is thermally cured to complete the color filter.
- the photosensitive composition for forming the black matrix part of the color filter has the coloring composition of the present invention, an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator as essential components, and these are mixed. Can be prepared.
- the colored resin film forming the black matrix portion is required toughness that can withstand baking performed in the actual production of the color filter, only the photopolymerizable monomer is used in preparing the photosensitive composition. In addition, it is essential to use this alkali-soluble resin together. When an alkali-soluble resin is used in combination, it is preferable to use an organic solvent that dissolves it.
- the colored composition of the present invention is prepared in advance, and then an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator are added to the photosensitive composition.
- the method of making a product is common.
- alkali-soluble resin used in the preparation of the photosensitive composition examples include a resin containing a carboxyl group or an acidic hydroxyl group, such as a novolak-type phenol resin, a (meth) acrylic acid alkyl ester- (meth) acrylic acid copolymer, Examples thereof include styrene- (meth) acrylic acid copolymers and styrene-maleic acid copolymers.
- description with (meth) acryl is a general term which combined acrylic and methacryl.
- alkali-soluble resin containing each polymerization unit of an imide structure, styrene, and (meth) acrylic acid is preferable to use.
- This alkali-soluble resin does not have the function of binding the organic pigment and the anchor part and having the compatible part extend into the dispersion medium to constitute the dispersion, but on the other hand, it is in contact with the alkali. This is used exclusively for the purpose of removing unexposed portions of the photosensitive composition, taking advantage of the characteristics of dissolution.
- photopolymerizable monomer examples include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bis [( (Meth) acryloxyethoxy] bisphenol A, bifunctional monomers such as 3-methylpentanediol di (meth) acrylate, trimethylol propaton tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (2-hydroxy Ethyl) isocyanurate tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, ditrimethylolpropane tetra (meth) acrylate Relatively high molecular weight of small polyfunctional monomer, polyester
- photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethylketanol, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, 1,3-bis (4 -Azidobenzal) -2-propane-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid, ethanone, 1- [9-ethyl-6- [2-methyl-4- ( 2,2-dimethyl-1,3-dioxolanyl) methoxybenzoyl] -9. H. -Carbazol-3-yl]-, 1- (O-acetyloxime) and the like.
- the photosensitive composition of the present invention is black, it is preferable to use a photopolymerization initiator having excellent curability.
- the cured film of the photosensitive composition has a maximum light transmittance in a wavelength range of 400 to 800 nm suitable for a black matrix. 1% or less, and the light transmittance in the near infrared region with a wavelength of 800 to 1100 nm can be 80%.
- the light transmittance of the black matrix is a spectrophotometer for a 3 ⁇ m thick black matrix (cured film) formed on a transparent substrate such as a glass substrate, with the substrate on which the resin black matrix is not formed as a control. It refers to the measured light transmittance.
- the maximum light transmittance means the largest value among the light transmittances in a specific wavelength region (range). More specifically, the maximum value of the light transmittance curve in a specific wavelength region. For example, “the maximum light transmittance in the wavelength range of 400 nm to 800 nm is 1% or less” means that the maximum value of the light transmittance curve in the wavelength range of 400 nm to 800 nm is 1% or less. It means that there is no region where the transmittance exceeds 1%.
- wavelength 800 nm to 1100 nm means a so-called near infrared region.
- a black matrix having a light transmittance of 80% or more in the near infrared region having a wavelength of 800 nm to 1100 nm is a black matrix having a low light absorption and a high light transmittance in the near infrared long region. The larger the light transmittance in the near infrared region, the more easily the black matrix emits heat generated in the TFT element that is a heat source. For this reason, in the TFT element, an increase in on-current and off-current is small, and thermal runaway is difficult to occur.
- the volume resistivity is 1 ⁇ 10 13 ⁇ ⁇ cm or more and the dielectric constant is 5 or less, short circuit of the TFT element (switching element made of a thin film transistor) due to leakage current can be reduced, and switching of the TFT element can be performed. It is transmitted accurately and disturbance of driving of the liquid crystal can be reduced.
- the volume resistivity is a measure of the insulating property of a substance, and is an electrical resistance per unit volume.
- the volume resistivity is described in, for example, the Institute of Electrical Engineers of the Institute of Electrical Engineers of Japan “Electrical Society of Japan: Electrical and Electronic Materials-From Basics to Test Methods” (Ohm Co., Ltd., 2006, pages 223 to 230). It can be measured by a technique.
- Dielectric constant means a so-called relative dielectric constant, which is a ratio between a dielectric constant of a substance and a dielectric constant of a vacuum.
- the dielectric constant can be measured by, for example, a method described in the Institute of Electrical Engineers of Japan, “The University of Electrical Engineers of Japan, Electrical and Electronic Materials-From Basics to Test Methods” (Ohm Co., Ltd., 2006, pp. 233 to 243). Can be measured.
- the total of the alkali-soluble resin and the photopolymerizable monomer is 3 to 20 parts per 100 parts of the colored composition of the present invention, and 0.05 parts per part of the photopolymerizable monomer.
- Photosensitivity for forming a black matrix part by adding ⁇ 3 parts photopolymerization initiator and, if necessary, further the organic solvent used for the preparation of the above-described coloring composition, and stirring and dispersing so as to be uniform. Can be obtained.
- the nonvolatile content is 5 to 20% in terms of mass. It is preferable to prepare such that
- the developer a known and commonly used alkaline aqueous solution can be used.
- the photosensitive composition contains an alkali-soluble resin, washing with an aqueous alkaline solution is effective for forming the black matrix portion.
- the excellent heat resistance of the photosensitive composition of the present invention is exhibited in a method for producing a color filter in which baking is performed after such alkali washing.
- the method for producing the black matrix portion by photolithography was described in detail, but the black matrix portion prepared using the photosensitive composition of the present invention is not limited to other electrodeposition methods, transfer methods, A color filter may be produced by forming the electrode by a method such as a micelle electrolysis method or a PVED (Photovoltaic Electrodeposition) method.
- the color filter uses a red organic pigment, a green organic pigment, a blue organic pigment, and a photosensitive composition of each color obtained by using the coloring composition of the present invention, and encapsulates a liquid crystal material between a pair of parallel transparent electrodes.
- the transparent electrode is divided into discontinuous fine sections, and red (R), green (G), and blue (B) are divided into the fine sections divided in a lattice form by the black matrix on the transparent electrode. It can be obtained by providing a color filter coloring pixel portion selected from any one color alternately in a pattern, or by forming a color filter coloring pixel portion on a substrate and then providing a transparent electrode.
- the black matrix portion obtained from the photosensitive composition of the present invention contains the above-mentioned blue, yellow, and red organic pigments so as to be black.
- the photosensitive compositions of the respective colors are mixed. It seems as if a black matrix similar to that obtained when the black photosensitive composition is prepared as described above, but in the present invention, at the time of preparing the coloring composition, which is the previous stage of making the photosensitive composition, As a result of mixing the organic pigments of the respective colors in advance, more uniform mixing is achieved, and a black matrix having better characteristics is obtained.
- Chromophthal Orange GP (CI Pigment Orange 64, manufactured by Ciba Specialty) 100 parts, 5 parts of phthalimidomethylated quinacridone, 1100 parts of sodium chloride, and 220 parts of diethylene glycol were charged into a stainless steel 1 L kneader (manufactured by Inoue Seisakusho). The mixture was kneaded at 7 ° C. for 7 hours. Next, this mixture is poured into 2 liters of warm water, stirred for 30 minutes to form a slurry, filtered and washed with water until the specific conductivity is 150 ⁇ S / cm or less, and after removing sodium chloride and the solvent at 90 ° C. It was dried and ground for 17 hours to obtain 105 parts of an orange pigment composition (P-1) for color filters.
- P-1 orange pigment composition
- a photosensitive resin composition (X-1) was prepared by mixing 75 parts by weight and 50 parts by weight of cyclohexanone.
- a 10 cm square glass substrate (Nippon Electric Glass color filter glass plate “OA-10”) is immersed in a 1% dilution of a silane coupling agent “KBM-603” manufactured by Shin-Etsu Chemical Co., Ltd. for 3 minutes and washed with water for 10 seconds. After draining with an air gun, it was dried in an oven at 110 ° C. for 5 minutes.
- the photosensitive resin composition (X-1) prepared above was applied using a spin coater. After vacuum drying for 1 minute, it was heated and dried at 90 ° C. for 90 seconds on a hot plate to obtain a coating film having a dry film thickness of about 3.5 ⁇ m.
- a colored composition (A-2) was obtained under the same conditions as in Example 1 except that 5 parts of phthalimidomethylated quinacridone was changed to 12 parts in the salt milling step of Example 1.
- a black matrix (B-2) was prepared in the same manner as in Example 1 except that the colored composition (A-1) was replaced with the colored composition (A-2).
- Example 5 the colored composition (A-4) was prepared under the same conditions as in Example 1 except that Chromophthal Orange GP was changed to Hosta Orange Orange HGL (CI Pigment Orange 60 manufactured by Clariant). Obtained.
- a black matrix (B-4) was prepared in the same manner as in Example 1 except that the colored composition (A-1) was replaced with the colored composition (A-4).
- the coloring composition (A-5) was used under the same conditions as in Example 1 except that in the salt milling process of Example 1, Chromophthal Orange GP was changed to Novo Orange Orange H5G70 (Cl. Pigment Orange 62 manufactured by Clariant). Obtained.
- a black matrix (B-5) was prepared in the same manner as in Example 1 except that the colored composition (A-1) was replaced with the colored composition (A-5).
- a colored composition (A-7) was obtained under the same conditions as in Example 1 except that in the salt milling step of Example 1, phthalimidomethylated quinacridone was changed to phthalimidomethylated phthalocyanine.
- a black matrix (B-7) was prepared in the same manner as in Example 1 except that the colored composition (A-1) was replaced with the colored composition (A-7).
- Example 1 In the process for producing the colored composition of Example 1, the subsequent operations were carried out in the same manner as in Example 1 without the salt milling process, to obtain a colored composition (A-8).
- a black matrix (B-8) was prepared in the same manner as in Example 1 except that the colored composition (A-1) was replaced with the colored composition (A-8).
- Example 2 A colored composition (A-9) was obtained under the same conditions as in Example 1 except that 5 parts of phthalimidomethylated quinacridone was changed to 0 part in the salt milling step of Example 1.
- a black matrix (B-9) was prepared in the same manner as in Example 1 except that the colored composition (A-1) was replaced with the colored composition (A-9).
- the OD values of the black matrices prepared in Examples and Comparative Examples are shown in Table 1 with the OD value of Example 1 converted to 100. Moreover, the primary particle diameter of the obtained orange pigment composition was also described. From the above, it has been clarified that the black matrix obtained from the pigment composition of the present invention has an improved OD value as compared with the conventional one.
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Abstract
Description
本発明のカラーフィルタ用顔料組成物は、特定の化学構造からなる有機顔料と特定の有機色素誘導体をソルベントソルトミリングすることにより、微細な粒子を形成することが可能となり、青色、黄色、赤色等の有機顔料を併用することにより、黒色のカラーフィルタ用有機顔料組成物を構成する。得られた黒色のカラーフィルタ用有機顔料組成物を含有するブラックマトリックスは、分散安定性に優れ、OD値の高い遮光性に優れたものである。
ここで用いられる有機溶剤としては、例えば、ジイソプロピルエーテル、ミネラルスピリット、n-ペンタン、アミルエーテル、エチルカプリレート、n-ヘキサン、ジエチルエーテル、イソプレン、エチルイソブチルエーテル、ブチルステアレート、n-オクタン、バルソル#2、アプコ#18ソルベント、ジイソブチレン、アミルアセテート、ブチルアセテート、アプコシンナー、ブチルエーテル、ジイソブチルケトン、メチルシクロヘキセン、メチルノニルケトン、プロピルエーテル、ドデカン、ソーカルソルベントNo.1及びNo.2、アミルホルメート、ジヘキシルエーテル、ジイソプロピルケトン、ソルベッソ#150、(n,sec,t-)酢酸ブチル、ヘキセン、シェルTS28 ソルベント、ブチルクロライド、エチルアミルケトン、エチルベンゾエート、アミルクロライド、エチレングリコールジエチルエーテル、エチルオルソホルメート、メトキシメチルペンタノン、メチルブチルケトン、メチルヘキシルケトン、メチルイソブチレート、ベンゾニトリル、エチルプロピオネート、メチルセロソルブアセテート、メチルイソアミルケトン、n-アミルメチルケトン(2-ヘプタノン)、メチルイソブチルケトン、プロピルアセテート、アミルアセテート、アミルホルメート、ビシクロヘキシル、ジエチレングリコールモノエチルエーテルアセテート、ジペンテン、メトキシメチルペンタノール、メチルアミルケトン、メチルイソプロピルケトン、プロピルプロピオネート、プロピレングリコール-t-ブチルエーテル、メチルエチルケトン、メチルセロソルブ、エチルセロソルブ、エチルセロソルブアセテート、カルビトール、シクロヘキサノン、酢酸エチル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテルアセテート、3-メトキシプロピオン酸、3-エトキシプロピオン酸、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、3-メトキシプロピオン酸メチル、3-メトキシプロピオン酸エチル、3-メトキシプロピオン酸プロピル、3-メトキシプロピオン酸ブチル、ジグライム、エチレングリコールアセテート、エチルカルビトール、ブチルカルビトール、エチレングリコールモノブチルエーテル、プロピレングリコール-t-ブチルエーテル、3-メトキシブタノール、3-メチル-3-メトキシブタノール、トリプロピレングリコールメチルエーテル、3-等が挙げられる。
なかでも、硬化皮膜の耐熱性をより高めるためには、イミド構造、スチレン及び(メタ)アクリル酸の各重合単位を含有するアルカリ可溶性樹脂を用いることが好ましい。
しかしながら、本発明の感光性組成物は、黒色であるため、硬化性に優れる光重合開始剤を用いることが好ましい。
近赤外線領域における光透過率が大きいほど、ブラックマトリックスは、発熱源であるTFT素子における発熱を発散しやすくなる。このため、TFT素子においてはオン電流やオフ電流の増加も少なく、熱暴走を起こし難くなる。
Cromophtal Orange GP(Ciba Speciality社製C.I.ピグメントオレンジ64)100部、フタルイミドメチル化キナクリドン5部、塩化ナトリウム1100部、およびジエチレングリコール220部をステンレス製1Lニーダー(井上製作所社製)に仕込み、90℃で7時間混練した。つぎにこの混合物を2リットルの温水に投入し、30分間攪拌してスラリー状とし、比電導度150μS/cm以下となるまで濾過、水洗をくりかえして塩化ナトリウムおよび溶剤を除いた後、90℃で17時間乾燥、粉砕し、カラーフィルタ用橙色顔料組成物(P―1)105部を得た。
橙色顔料組成物(P―1)5.1部、FASTOGEN BLUE EP-CF(DIC株式会社製C.I.ピグメントブルー15:6)5.59、IRGAFORE RED BT-CF(Ciba Speciality社製C.I.ピグメントレッド254)4.31部、樹脂系分散剤としてPB-821(味の素ファインテクノ株式会社製、ポリエステル樹脂系分散剤)4.5部、プロピレングリコールモノメチルアセテート73.75gの混合物に0.2~0.3mmφのジルコニアビーズを加え、ペイントコンディショナーで2時間分散し、着色組成物(A-1)を得た。
着色組成物(A-1)100部、アルカリ可溶性樹脂(B)としてメタクリル酸/こはく酸モノ(2-メタクリロイロキシエチル)/N-フェニルマレイミド/スチレン/ベンジルメタクリレート共重合体(共重合質量比=25/10/30/20/15、Mw=12,000、Mn=6,500)5部、光重合性モノマー(C)としてジペンタエリスリトールヘキサアクリレート10部、光重合開始剤(D)としてエタノン,1-〔9-エチル-6-[2-メチル-4-(2,2-ジメチル-1,3-ジオキソラニル)メトキシベンゾイル]-9.H.-カルバゾール-3-イル〕-,1-(O-アセチルオキシム)を1部、および有機溶剤(E)としてジプロピレングリコールジメチルエーテル25重量部、プロピレングリコールモノメチルエーテルアセテート25重量部、3-メトキシブチルアセテート75重量部、シクロヘキサノン50重量部を混合して、感光性樹脂組成物(X-1)を調製した。
10cm角のガラス基板(日本電気硝子製カラーフィルタ用ガラス板「OA-10」)を信越化学製シランカップリング剤「KBM-603」の1%希釈液に3分間浸漬し、10秒間水洗して、エアーガンで水切り後、110℃のオーブンで5分間乾燥した。このガラス基板上に、上記にて調製した感光性樹脂組成物(X-1)をスピンコーターを用いて塗布した。1分間真空乾燥後、ホットプレート上で90℃にて90秒間加熱乾燥し、乾燥膜厚約3.5μmの塗布膜を得た。その後、塗布膜側から、15μm幅の細線パターンマスクを介して画像露光を施すもの(パターン1)と、マスクを介さずに全面に露光を施すもの(パターン2)との2通りの露光を行った。露光条件は、それぞれ3kW高圧水銀灯を用い50mJ/cm2(i線基準)とした。次いで、0.05%の水酸化カリウムと0.08%のノニオン性界面活性剤(花王製「A-60」)を含有する水溶液よりなる現像液を用い、23℃において水圧0.15MPaのシャワー現像を施した後、純水にて現像を停止し、水洗スプレーにて洗浄しブラックマトリックス(B-1)を得た。なお、シャワー現像時間は、10~120秒間の間で調整し、未露光の塗布膜が溶解除去される時間の1.5倍とした。
[実施例2]
[実施例3]
[実施例4]
[実施例5]
[実施例6]
[実施例7]
実施例1の着色組成物の作製工程において、ソルトミリング工程無しで、それ以降の操作は、実施例1と同様に行い着色組成物(A-8)を得た。着色組成物(A-1)を着色組成物(A-8)に代える以外は、上記実施例1と同様の操作を行い、ブラックマトリックス(B-8)を調製した。
実施例1のソルトミリング工程において、フタルイミドメチル化キナクリドン5部を0部に変更した以外は、実施例1と同条件で着色組成物(A-9)を得た。着色組成物(A-1)を着色組成物(A-9)に代える以外は、上記実施例1と同様の操作を行い、ブラックマトリックス(B-9)を調製した。
以上より、本発明の顔料組成物から得られたブラックマトリックスは、従来よりもOD値が向上することが明らかとなった。
Claims (4)
- 前記有機顔料が、C.I.ピグメントオレンジ36、60、62、64、72の少なくとも一つから選ばれるオレンジ顔料であることを特徴とする請求項1記載のカラーフィルタ用有機顔料組成物。
- 前記有機色素誘導体がフタルイミドアルキル化キナクリドンまたはフタルイミドアルキル化フタロシアニンの少なくとも一つから選ばれる有機色素誘導体であることを特徴とする請求項1記載のカラーフィルタ用有機顔料組成物。
- 請求項1~3のいずれか記載のカラーフィルタ用有機顔料組成物を含有することを特徴とするカラーフィルタ。
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