WO2018043548A1 - Composition de pigments pour filtres colorés, et filtre coloré - Google Patents

Composition de pigments pour filtres colorés, et filtre coloré Download PDF

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Publication number
WO2018043548A1
WO2018043548A1 PCT/JP2017/031119 JP2017031119W WO2018043548A1 WO 2018043548 A1 WO2018043548 A1 WO 2018043548A1 JP 2017031119 W JP2017031119 W JP 2017031119W WO 2018043548 A1 WO2018043548 A1 WO 2018043548A1
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Prior art keywords
pigment
parts
color filter
green
composition
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PCT/JP2017/031119
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English (en)
Japanese (ja)
Inventor
圭亮 坂本
木村　亮
望 嶋田
祐奈 千葉
融 石井
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Dic株式会社
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Priority to JP2018530919A priority Critical patent/JP6477977B2/ja
Priority to CN201780051904.9A priority patent/CN109642970B/zh
Priority to KR1020197005587A priority patent/KR102383525B1/ko
Publication of WO2018043548A1 publication Critical patent/WO2018043548A1/fr

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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
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/04—Compounds of zinc
    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/085—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex substituting the central metal atom
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors

Definitions

  • the present invention relates to a color filter pigment composition and a color filter.
  • the color filter used in the liquid crystal display is a member that realizes the color display of the display by transmitting the white light of the backlight.
  • green colorants for color filters are required to have high brightness and high color reproduction.
  • Pigment Green 58 is used as a main pigment.
  • three-color LEDs as backlight LEDs have little cost merit.
  • a pseudo white LED (a combination of a blue LED and a yellow phosphor (B-YAG) or a combination of a blue LED, a red phosphor and a green phosphor (B) is formed by applying a phosphor on the surface of the blue LED.
  • B-YAG yellow phosphor
  • a red phosphor and a green phosphor B
  • -RG green phosphor
  • a pigment capable of displaying a vivid color in addition to high brightness is selected.
  • the film thickness of the color filter may be increased.
  • the film thickness must be suppressed to about 3 ⁇ m or less.
  • High color reproduction displays that are expected to become popular in the future are expected to be designed with DCI-P3.
  • pigment green 36 or 58 is used, the film thickness greatly exceeds 3 ⁇ m, so that pigment green 7 is selected as the main pigment.
  • Pigment Green 59 As a new high color reproduction pigment, and when compared with the case where a color filter having the same film thickness is produced, the use of Pigment Green 59 has higher luminance than the use of Pigment Green 7 (for example, Patent Documents). 1).
  • Pigment Green 58 for the color filter for high-luminance display and Pigment Green 59 for the color filter for high-color reproduction display.
  • the major difference between the color filter for a high luminance display and the color filter for a high color reproduction display is the chromaticity and the type of backlight for designing the green pixel.
  • Pigment Green 58 As described above, it is recognized that it is better to use Pigment Green 58 as a color filter for a high brightness display. However, in order to supplement the characteristics of B-YAG, which is a backlight having a weak green emission intensity, it has been desired to further increase the brightness of the green pigment.
  • the present invention has been made in view of the above circumstances, and provides a novel color filter pigment composition capable of producing a high-luminance color filter and a color filter containing the color filter pigment composition.
  • the color filter pigment composition according to the first aspect of the present invention has a transmittance of 45% or more at a wavelength of 555 nm when a coating film is formed so that the spectral transmittance at a maximum transmission wavelength is 80%. It contains a green pigment having spectral characteristics such that the ratio of the transmittance at a wavelength of 505 nm to the transmittance at a wavelength of 555 nm (T (505 nm) / T (555 nm)) is 1.40 or more and the half width is 80 nm or less.
  • the green pigment may be brominated chlorinated zinc phthalocyanine.
  • the green pigment may be brominated chlorinated zinc phthalocyanine containing an average of 13 to 15 bromine and an average of 1 to 3 chlorine in one molecule.
  • the color filter pigment composition according to the first aspect may further contain a yellow pigment.
  • the color filter according to the second aspect of the present invention contains the color filter pigment composition according to the first aspect.
  • a high-luminance color filter can be produced.
  • FIG. 3 is a view showing spectral transmission spectra (wavelengths of 480 to 580 nm) of evaluation compositions 1 to 7 and 9 to 12 in Example 1 and Comparative Example 1.
  • FIG. 3 is a view showing spectral transmission spectra (wavelengths of 440 to 480 nm) of evaluation compositions 1 to 7 and 9 to 12 in Example 1 and Comparative Example 1.
  • FIG. 3 is a view showing spectral transmission spectra (wavelengths of 580 to 620 nm) of evaluation compositions 1 to 7, 9, 10, and 12 in Example 1 and Comparative Example 1.
  • the present invention contains a green pigment having the following spectral characteristics (a) to (c) when a coating film is formed so that the spectral transmittance at a maximum transmission wavelength is 80%.
  • a pigment composition for a color filter is provided.
  • the transmittance at a wavelength of 555 nm is 45% or more.
  • the ratio of the transmittance at a wavelength of 505 nm to the transmittance at a wavelength of 555 nm (T (505 nm) / T (555 nm)) is 1.40 or more
  • Half width is 80nm or less
  • the color filter pigment composition of the present embodiment it is possible to provide a high-luminance color filter that can supplement the characteristics of LED-YAG, which is a backlight with a small amount of green light.
  • the spectral transmittance in this specification can be obtained by measuring a spectral transmission spectrum.
  • the “spectral transmission spectrum” is obtained according to a first-class spectrophotometer according to Japanese Industrial Standard JIS Z 8722 (color measurement method—reflection and transmission object color).
  • the resin film containing the pigment formed on the glass substrate or the like with the predetermined dry film thickness is obtained by plotting each transmittance value at each wavelength by scanning and irradiating light in a predetermined wavelength region. .
  • the green pigment contained in the color filter pigment composition of the present embodiment has the following spectral (a) to (c) when the coating film is formed so that the spectral transmittance at the maximum transmission wavelength is 80%.
  • (B) The ratio of the transmittance at a wavelength of 505 nm to the transmittance at a wavelength of 555 nm (T (505 nm) / T (555 nm)) is 1.40 or more
  • Half width is 80nm or less
  • the green color filter it is important to increase the transmittance in the range from 510 nm to 560 nm in order to ensure the brightness. Moreover, when toning with a yellow pigment, it shifts to the long wavelength side by about 5 nm by blending the yellow pigment. Therefore, it is important to obtain a bright display by increasing the transmission wavelength at 505 nm while keeping the transmittance at 555 nm high.
  • the transmittance at 460 nm is high, the value of chromaticity y is greatly reduced and the green vividness (saturation) is lost. Therefore, it is preferable that the transmittance at 460 nm after toning with a yellow pigment is low.
  • the yellow pigment Y138 is a pigment that absorbs a shorter wavelength than 460 nm.
  • the green pigment has a high transmittance of 460 nm, it is necessary to design the amount of Y138 to be extremely increased.
  • the green pigment has a low transmittance at 460 nm. From the viewpoint of increasing the value of chromaticity y, it is preferable that when the coating film is formed so that the spectral transmittance at the maximum transmission wavelength is 80%, the transmittance of 460 nm of the green pigment is 3% or less. It is more preferably 2% or less, and further preferably 1% or less.
  • the transmittance at 605 nm after toning with a yellow pigment is preferably low. Toning with a yellow pigment shifts to the long wavelength side by about 5 nm, so the green pigment preferably has a low transmittance of 600 nm. From the viewpoint of reducing the value of chromaticity x, it is preferable that when the coating film is formed so that the spectral transmittance at the maximum transmission wavelength is 80%, the transmittance of the green pigment at 600 nm is 1% or less. It is more preferably 0.5% or less, and further preferably 0.3% or less. That is, a green pigment having a large transmission spectrum of T (505 nm) / T (555 nm) and low transmittance at 460 nm and 600 nm is required for realizing high luminance and excellent color reproducibility.
  • the green pigment contained in the color filter pigment composition of the present embodiment has the spectral characteristics (a) to (c) described above.
  • the green pigment contained in the color filter pigment composition of the present embodiment has a low transmittance at 460 nm and 600 nm when a coating film is formed so that the spectral transmittance at the maximum transmission wavelength is 80%.
  • a color filter having color reproducibility superior to that of the conventional green pigment can be obtained.
  • the green pigment contained in the color filter pigment composition of the present embodiment has a maximum transmission wavelength of 515 nm when the coating film is formed so that the spectral transmittance at the maximum transmission wavelength is 80%.
  • the thickness is preferably in the range of 530 nm or less.
  • the green pigment having the above spectral characteristics may be an inorganic pigment or an organic pigment.
  • the green pigment is preferably an organic pigment, more preferably a phthalocyanine compound, and further preferably a phthalocyanine compound having a metal atom at the center.
  • the “phthalocyanine compound” is a cyclic compound having a structure in which four phthalimides are cross-linked by nitrogen atoms.
  • the “phthalocyanine compound having a metal atom at the center” is a compound having a structure in which four nitrogen atoms at the center of the phthalocyanine compound and a metal atom are chemically bonded (for example, covalent bond, coordinate bond, etc.).
  • the metal atom present at the center of the phthalocyanine compound is not particularly limited, and examples thereof include Zn, Mg, Al, Si, Ti, V, Mn, Fe, Co, Ni, Ge, and Sn. Among these, the metal atom present at the center of the phthalocyanine compound is preferably Zn (zinc).
  • the phthalocyanine compound having a metal atom at the center of the green pigment is preferably zinc phthalocyanine, more preferably zinc halide phthalocyanine, and further preferably brominated chlorinated zinc phthalocyanine.
  • the green pigment is brominated chlorinated zinc phthalocyanine, from the point of having the above spectral characteristics, an average of 14 to 16 halogen atoms, an average of 13 to 15 bromine atoms, and an average of chlorine in one molecule It is preferable to contain 1 or more and 3 or less.
  • the hue of the pigment is yellowed only by increasing the halogenation rate, increasing the number of bromines in one molecule of brominated chlorinated zinc phthalocyanine than the number of chlorines while maintaining the green hue, A green pigment with high brightness can be obtained.
  • the bromine number in one molecule of brominated chlorinated zinc phthalocyanine is preferably 7 times or more on average, more preferably 7 to 9 times on average, The average is more preferably 7.8 times or more and 9 times or less.
  • the number of halogen atoms in one molecule of the brominated chlorinated zinc phthalocyanine can be measured by using a method (fluorescence X-ray analysis) shown in Examples described later.
  • the halogenated metal phthalocyanine in the green pigment can be produced by a known production method such as a chlorosulfonic acid method, a halogenated phthalonitrile method, or a melting method.
  • Examples of the chlorosulfonic acid method include a method in which metal phthalocyanine is dissolved in a sulfur oxide-based solvent such as chlorosulfonic acid, and chlorine gas and bromine are added thereto to perform halogenation.
  • the reaction at this time is performed at a temperature of 20 ° C. or higher and 120 ° C. or lower and a range of 3 hours or longer and 20 hours or shorter.
  • halogenated phthalonitrile method for example, phthalic acid or phthalodinitrile in which part or all of the hydrogen atoms of the aromatic ring are substituted with halogen atoms such as bromine and chlorine, and a metal or metal salt of zinc are appropriately used as starting materials. And a method for synthesizing a corresponding metal halide phthalocyanine. In this case, a catalyst such as ammonium molybdate may be used as necessary. The reaction at this time is performed at a temperature of 100 ° C. or more and 300 ° C. or less and in a range of 7 hours or more and 35 hours or less.
  • Examples of the melting method include aluminum halides such as aluminum chloride and aluminum bromide, titanium halides such as titanium tetrachloride, alkali metal halides such as sodium chloride and sodium bromide, or alkaline earth metal halides (hereinafter, About 10 ° C to 170 ° C, consisting of one or a mixture of two or more compounds that serve as solvents during various halogenations, such as "alkaline (earth) metal halides”) and thionyl chloride And a method of halogenating metal phthalocyanine with a halogenating agent.
  • aluminum halides such as aluminum chloride and aluminum bromide
  • titanium halides such as titanium tetrachloride
  • alkali metal halides such as sodium chloride and sodium bromide
  • alkaline earth metal halides hereinafter, About 10 ° C to 170 ° C, consisting of one or a mixture of two or more compounds that serve as solvents during various halogenations,
  • the aluminum halide is preferably aluminum chloride.
  • the amount of aluminum halide added is usually 3 times mol or more, preferably 10 times mol or more and 20 times mol or less with respect to zinc phthalocyanine.
  • Aluminum halide may be used alone, but when an alkali (earth) metal halide is used in combination with aluminum halide, the melting temperature can be further lowered, which is advantageous in operation.
  • the alkali (earth) metal halide is preferably sodium chloride.
  • the amount of the alkali (earth) metal halide to be added is preferably 5 parts by mass or more and 15 parts by mass or less of the alkali (earth) metal halide with respect to 10 parts by mass of the aluminum halide within the range in which the molten salt is formed.
  • examples of the halogenating agent include chlorine gas, sulfuryl chloride, bromine and the like.
  • the halogenation temperature is preferably 10 ° C. or higher and 170 ° C. or lower, and more preferably 30 ° C. or higher and 140 ° C. or lower. Furthermore, pressurization may be performed to increase the reaction rate.
  • the reaction time is preferably 5 hours or more and 100 hours or less, and more preferably 30 hours or more and 45 hours or less.
  • a melting method in which two or more kinds of compounds that become a solvent in the halogenation are used in combination is preferable.
  • the content ratio of the halogenated zinc phthalocyanine having a specific halogen atom composition in the zinc halide phthalocyanine can be arbitrarily controlled.
  • the metal phthalocyanine that is a suitable raw material in the present embodiment is zinc phthalocyanine.
  • the melting method is suitable because the raw material during the reaction is less decomposed and the yield from the raw material is better, and the reaction can be carried out in an inexpensive apparatus without using a strong acid.
  • Zinc halide phthalocyanine having a halogen atom composition different from that of existing zinc halide phthalocyanine can be obtained by optimizing the raw material charging method, catalyst type and amount, reaction temperature and reaction time.
  • the produced metal halide phthalocyanine is precipitated.
  • the metal halide phthalocyanine it may be used as it is, but then filtered or washed with water, sodium hydrogen sulfate aqueous solution, sodium hydrogen carbonate aqueous solution or sodium hydroxide aqueous solution, if necessary acetone, toluene, methyl It is preferably used after washing with an organic solvent such as alcohol, ethyl alcohol, dimethylformamide, and after-treatment such as drying.
  • Halogenated metal phthalocyanine is pigmented by dry grinding in a pulverizer such as an attritor, ball mill, vibration mill, vibration ball mill, etc. Compared to the former, it is possible to obtain a pigment that is excellent in dispersibility and coloring power and has a high lightness to develop a green color.
  • the metal halide phthalocyanine before pigmentation may be dispersed in a dispersion medium and pigmented at the same time.
  • a method for forming a halogenated metal phthalocyanine pigment particles that can easily suppress crystal growth and have a large specific surface area can be obtained compared to a solvent treatment in which a halogenated metal phthalocyanine is heated and stirred in a large amount of an organic solvent.
  • This solvent salt milling means kneading and grinding a crude pigment, which is a halogenated metal phthalocyanine that has not undergone pigmentation, ground immediately after synthesis or after that, an inorganic salt, and an organic solvent.
  • a crude pigment, an inorganic salt, and an organic solvent that does not dissolve it are charged into a kneader and kneaded and ground therein.
  • a kneader at this time for example, a kneader, a mix muller, or the like can be used.
  • a water-soluble inorganic salt can be preferably used.
  • an inorganic salt such as sodium chloride, potassium chloride, sodium sulfate is preferably used.
  • Such an inorganic salt can be easily obtained by pulverizing a normal inorganic salt.
  • the amount of inorganic salt used is preferably 5 parts by mass or more and 20 parts by mass or less, and more preferably 7 parts by mass or more and 15 parts by mass or less with respect to 1 part by mass of the crude pigment.
  • an organic solvent that can suppress crystal growth is preferable to use an organic solvent that can suppress crystal growth as the organic solvent.
  • a water-soluble organic solvent can be preferably used.
  • the water-soluble organic solvent include diethylene glycol, glycerin, ethylene glycol, propylene glycol, liquid polyethylene glycol, liquid polypropylene glycol, 2- (methoxymethoxy) ethanol, 2-butoxyethanol, 2- (isopentyloxy).
  • the usage-amount of the said water-soluble organic solvent is not specifically limited, 0.01 mass part or more and 5 mass parts or less are preferable with respect to 1 mass part of crude pigments.
  • the temperature during solvent salt milling is preferably 30 ° C. or higher and 150 ° C. or lower, and more preferably 80 ° C. or higher and 100 ° C. or lower.
  • the solvent salt milling time is preferably 5 hours or more and 20 hours or less, and more preferably 8 hours or more and 18 hours or less.
  • a mixture containing a metal halide phthalocyanine pigment, an inorganic salt, and an organic solvent as main components having an average primary particle size of 50 nm or less is obtained.
  • the organic solvent and the inorganic salt are removed from the mixture, and the solid material mainly containing the halogenated metal phthalocyanine pigment is washed, filtered, dried, pulverized, etc. as necessary to obtain a powder of the halogenated metal phthalocyanine pigment. Can be obtained.
  • washing either water washing or hot water washing can be adopted. What is necessary is just to repeat the frequency
  • the organic solvent and the inorganic salt can be easily removed by washing with water. If necessary, acid cleaning, alkali cleaning, or organic solvent cleaning may be performed so as not to change the crystal state.
  • drying after the filtration and washing described above for example, batchwise or continuous in which at least one of dehydration or desolvation of the pigment is performed by heating at 80 ° C. or more and 120 ° C. or less by a heating source installed in a dryer. And drying of the formula.
  • the dryer generally include a box-type dryer, a band dryer, and a spray dryer.
  • spray dry drying is preferable because it is easily dispersed during paste preparation.
  • pulverization after drying is not an operation for increasing the specific surface area or reducing the average particle size of the primary particles.
  • the pulverization after drying is performed in order to break the pigment into powder when the pigment is in a lamp shape or the like, for example, in the case of drying using a box dryer or a band dryer.
  • the pulverizer used after drying include a mortar, a hammer mill, a disk mill, a pin mill, and a jet mill. In this way, a dry powder of a pigment containing a metal halide phthalocyanine pigment as a main component is obtained.
  • the green pigment may contain one kind of compound that is derived from coloring, or may contain two or more kinds. When two or more types are included, each compound contained in the green pigment may be mixed and then pigmented, or each compound contained in the green pigment may be pigmented and then mixed.
  • the pigment composition for color filters of this embodiment can contain at least 1 or more yellow pigment with the said green pigment.
  • yellow pigments examples include C.I. I. Pigment Yellow (PY) 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36 : 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100 , 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 126, 127, 128, 129, 138, 139, 150, 151, 152, 153, 154 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 85,187,199,231, and the like.
  • the yellow pigment PY83, 138, 139, 150, 185, or 231 is preferable because it has high luminance or a small amount of pigment and is suitable for thinning, and PY138, 150, 185, or 231 is preferable. Is particularly preferred. These can be used alone or in combination of two or more.
  • the mixing ratio of the green pigment and the yellow pigment is such that the yellow pigment is 1 part by mass or more and 400 parts by mass or less per 100 parts by mass of the green pigment. I just need it.
  • the color filter pigment composition of the present embodiment even when a yellow pigment is used together for toning, a high-luminance color filter green pixel portion is produced as compared with the case of using a conventional green pigment. Can do.
  • the color filter pigment composition of the present embodiment can be produced using a known production method.
  • the method for producing the green pigment is as described above. Specifically, a green pigment and, if necessary, a yellow pigment are dry-ground in a pulverizer such as an attritor, ball mill, vibration mill, vibration ball mill, etc., and then a solvent salt milling method or a solvent boiling method is used. Can be pigmented.
  • a pulverizer such as an attritor, ball mill, vibration mill, vibration ball mill, etc.
  • the pigment composition for a color filter of the present embodiment has an average primary particle size of 50 nm or less, preferably 1 nm or more and 50 nm or less, relatively weak pigment aggregation, and dispersibility in a synthetic resin to be colored. Is better. Moreover, it is more preferable that it is 1 nm or more and 20 nm or less.
  • the “average particle diameter of primary particles” can be calculated using the following measurement method. First, the particles of the color filter pigment composition of the present embodiment in the field of view are photographed with a transmission electron microscope JEM-2010 (manufactured by JEOL Ltd.). Next, the longer diameter (major diameter) of 50 primary particles of the color filter pigment composition of the present embodiment constituting the aggregate on the two-dimensional image is determined. Next, the average particle diameter of the primary particles can be calculated by averaging the obtained long diameters. At this time, the color filter pigment composition of the present embodiment as a sample is ultrasonically dispersed in a solvent and then photographed with a microscope. A scanning electron microscope may be used instead of the transmission electron microscope.
  • a color filter can be obtained by forming a green pixel using the color filter pigment composition of the present embodiment.
  • the green pixel formed using the color filter pigment composition of the present embodiment has high luminance. Therefore, it is possible to manufacture a liquid crystal display device including a color filter having a high display performance and a liquid crystal panel including the green pixel.
  • the pigment composition for a color filter of this embodiment can be used for forming a pattern of a green pixel portion of a color filter by a known method.
  • the color filter green pixel part photosensitive composition containing the pigment composition for color filters of this embodiment and the photosensitive resin as an essential component can be obtained.
  • Examples of the method for producing a color filter include a method called photolithography shown below. Specifically, first, the color filter pigment composition of the present embodiment is dispersed in a dispersion medium made of a photosensitive resin. Next, this dispersion is applied onto a transparent substrate such as glass by a spin coating method, a roll coating method, a slit coating method, an ink jet method or the like to obtain a coating film. Subsequently, pattern exposure with ultraviolet rays is performed on the coating film through a photomask. Next, the unexposed portion is washed with a solvent or the like to obtain a green pattern.
  • a method called photolithography shown below. Specifically, first, the color filter pigment composition of the present embodiment is dispersed in a dispersion medium made of a photosensitive resin. Next, this dispersion is applied onto a transparent substrate such as glass by a spin coating method, a roll coating method, a slit coating method, an ink jet method or the like to obtain a coating film.
  • Examples of other manufacturing methods include a method of manufacturing a color filter by forming a pattern of a green pixel portion by a method such as an electrodeposition method, a transfer method, a micellar electrolysis method, a PVED (Photovoltaic Electrodeposition) method, or the like. .
  • the red pixel portion pattern and the blue pixel portion pattern can also be formed by a similar method using a known pigment.
  • the photosensitive composition for the color filter green pixel portion for example, the color filter pigment composition of the present embodiment, a photosensitive resin, a photopolymerization initiator, and an organic solvent that dissolves the resin. Mix as an essential ingredient. More specifically, there is a method of preparing a dispersion by using a pigment composition for a color filter of the present embodiment, an organic solvent, and a dispersant as required, and then adding a photosensitive resin or the like to the dispersion. It is common.
  • dispersing agent examples include Disperbyk (registered trademark) 130, 161, 162, 163, 170, LPN-6919, LPN-21116, etc. manufactured by BYK Chemie. Further, a leveling agent, a coupling agent, a cationic surfactant and the like may be used in combination.
  • organic solvent examples include aromatic solvents such as toluene, xylene and methoxybenzene, acetate solvents such as ethyl acetate and butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate.
  • Propionate solvents such as methanol, ethanol solvents such as methanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, etc.
  • Aliphatic hydrocarbon solvents N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone Aniline, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as ⁇ - butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate, there is water.
  • nitrogen compound-based solvent such as pyridine
  • a lactone-based solvents such as ⁇ - butyrolactone
  • carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate
  • organic solvent polar solvents such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, lactone-based, and water-soluble ones are particularly suitable.
  • a high boiling point solvent having a boiling point of 150 ° C. or higher can also be used as appropriate.
  • the organic solvent of 300 parts by weight or more and 1000 parts by weight or less and, if necessary, the dispersant of 0 parts by weight or more and 100 parts by weight or less per 100 parts by weight of the color filter pigment composition of the present embodiment are made uniform.
  • the dispersion can be obtained by stirring and dispersing.
  • the following photopolymerization initiator and, if necessary, an organic solvent may be further added and stirred and dispersed so as to be uniform to obtain a photosensitive composition for a color filter green pixel portion.
  • thermoplastic resins such as urethane resins, acrylic resins, polyamic acid resins, polyimide resins, styrene maleic acid resins, styrene maleic anhydride resins, and 1,6-hexane, for example.
  • Bifunctional monomers such as diol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, trimethylolpropane triacrylate , Pentaerythritol triacrylate, tris (2-hydroxyethyl) isocyanate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, etc. Photopolymerizable monomer, such monomers.
  • photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethyl ketal, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, 1,3-bis (4 ′).
  • acetophenone benzophenone, benzyldimethyl ketal, 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, and the like.
  • the prepared photosensitive composition for the color filter green pixel portion is subjected to pattern exposure with ultraviolet rays through a photomask, and then the unexposed portion is washed with an organic solvent or alkaline water to obtain a color filter. Can do.
  • the average number of chlorine atoms and the average number of bromine atoms were measured by fluorescent X-ray analysis using ZSX100E manufactured by Rigaku Corporation. From the mass ratio of zinc atoms, chlorine atoms and bromine atoms, per one zinc atom was calculated as a relative value.
  • 1 g of zinc halide phthalocyanine was pressure-molded (25 mm ⁇ ) as a measurement sample, and measurement was performed in a measurement diameter of 20 mm ⁇ in a vacuum atmosphere.
  • a halogenated zinc phthalocyanine pigment having an average number of halogen atoms in one molecule of 15.73, of which the average number of bromine atoms is 14.13 and the average number of chlorine atoms is 1.60. Met.
  • the average particle size of the primary particles was 0.02 ⁇ m from the particle size measurement with a transmission electron microscope JEM-2010 manufactured by JEOL Ltd.
  • the average number of halogen atoms in one molecule was 11.15, of which the average number of bromine atoms was 8.63 and the average number of chlorine atoms was 2.52. It was a phthalocyanine pigment.
  • the obtained pigment 2-2 was subjected to fluorescent X-ray analysis using the same method as in Production Example 1.
  • the average number of halogen atoms in one molecule was 15.30, of which the average number of bromine atoms was 13.59 and the average number of chlorine atoms was 1.71 It was a phthalocyanine pigment.
  • the obtained pigment 2-2 had an average primary particle size of 0.02 ⁇ m as determined by measuring the particle size with a transmission electron microscope JEM-2010 manufactured by JEOL Ltd.
  • the obtained pigment 3 was subjected to fluorescent X-ray analysis using the same method as in Production Example 1.
  • a halogenated zinc phthalocyanine pigment having an average number of halogen atoms in one molecule of 15.10, of which the average number of bromine atoms is 13.36 and the average number of chlorine atoms is 1.74. Met.
  • the average particle diameter of primary particles was 0.02 ⁇ m from the measurement of the particle diameter with a transmission electron microscope JEM-2010 manufactured by JEOL Ltd.
  • Pigment 5 20 parts of crude pigment 1 of Production Example 1, 1.5 parts of VS-1028 manufactured by Seiko PMC, 140 parts of crushed sodium chloride, 32 parts of diethylene glycol, and 1.8 parts of xylene were charged into a 1 L double arm kneader at 30 ° C. Kneaded for 15 hours. After kneading, it was taken out in 2 kg of water at 30 ° C., stirred for 1 hour, filtered, washed with hot water, dried and pulverized to obtain pigment 5. The obtained pigment 5 was found to have an average primary particle size of 0.02 ⁇ m as measured by a transmission electron microscope JEM-2010 manufactured by JEOL Ltd.
  • Example 1 Toning with a yellow pigment
  • Toning composition and evaluation composition 1, evaluation composition 2, evaluation composition 3, evaluation composition 3, evaluation so that coating film chromaticity is (x, y) (0.275, 0.570)
  • the glass substrate for evaluation was obtained by mixing the composition 4 for evaluation, the composition 5 for evaluation, the composition 6 for evaluation, or the composition 7 for evaluation, and forming into a film.
  • the luminance at C light source was measured with U-3900 manufactured by Hitachi High-Technologies Corporation. The results are shown in Table 1 below.
  • Pigment Green 58 (FASTOGEN Green A110) Pigment Green 58 (FASTOGEN Green A110) 2.48 parts, BYK-LPN6919 1.24 parts, Unidic ZL-295 1.86 parts, propylene glycol monomethyl ether acetate 10.92 parts, 0.3 to 0.4 mm Using zircon beads, the mixture was dispersed with a paint shaker for 2 hours to obtain a colored composition 9. Coloring composition 9 4.0 parts, Unidic ZL-295 0.98 parts, propylene glycol monomethyl ether acetate 0.22 parts are added and mixed with a paint shaker to form a green pixel part for a color filter A composition 9 for evaluation was obtained.
  • This evaluation composition 9 was spin-coated on soda glass and dried at 90 ° C. for 3 minutes to obtain an evaluation glass substrate.
  • the monochromatic spectral transmission spectrum of this glass substrate for evaluation was measured using U-3900 manufactured by Hitachi High-Technologies Corporation. Spectral transmission spectra are shown in FIGS. 1A, 1B and 1C.
  • Pigment Green 59 (FASTOGEN Green C100) Pigment Green 59 (FASTOGEN Green C100) 2.48 parts, BYK-LPN6919 1.24 parts, Unidic ZL-295 1.86 parts, propylene glycol monomethyl ether acetate 10.92 parts, 0.3 to 0.4 mm Using zircon beads, the mixture was dispersed for 2 hours with a paint shaker to obtain a colored composition 10. Coloring composition 10 4.0 parts, Unidic ZL-295 0.98 parts, propylene glycol monomethyl ether acetate 0.22 parts are added and mixed with a paint shaker to form a green pixel part for a color filter A composition for evaluation 10 was obtained.
  • This evaluation composition 10 was spin-coated on soda glass and dried at 90 ° C. for 3 minutes to obtain an evaluation glass substrate.
  • the monochromatic spectral transmission spectrum of this glass substrate for evaluation was measured using U-3900 manufactured by Hitachi High-Technologies Corporation. Spectral transmission spectra are shown in FIGS. 1A, 1B and 1C.
  • Pigment Green 7 (FASTOGEN Green S) Pigment Green 7 (FASTOGEN Green S) 1.65 parts, BYK-LPN6919 1.93 parts, propylene glycol monomethyl ether acetate 12.93 parts, and 0.3 to 0.4 mm zircon beads, 2 in a paint shaker After time dispersion, a colored composition 11 was obtained. Coloring composition 11 6.0 parts, Unidic ZL-295 1.47 parts, propylene glycol monomethyl ether acetate 0.33 parts are added and mixed with a paint shaker to form a green pixel part for a color filter A composition for evaluation 11 was obtained. This evaluation composition 11 was spin-coated on soda glass and dried at 90 ° C. for 3 minutes to obtain an evaluation glass substrate.
  • the monochromatic spectral transmission spectrum of this glass substrate for evaluation was measured using U-3900 manufactured by Hitachi High-Technologies Corporation. Spectral transmission spectra are shown in FIGS. 1A and 1B. Since Pigment Green 7 is a pigment having a low transmittance, it floats when the coating film is formed so that the spectral transmittance at the maximum transmission wavelength is 80%. Therefore, the pigment green 7 has a wavelength of 580 to 620 nm shown in FIG. 1C. No data is shown in the spectral transmission spectrum of the range.
  • Pigment Green 36 (FASTOGEN Green 2YK-50) CI Pigment Green 36 (FASTOGEN Green 2YK-50) 2.48 parts together with BYK-LPN6919 1.24 parts, Unidic ZL-295 1.86 parts, propylene glycol monomethyl ether acetate 10.92 parts and 0.3-0.
  • the mixture was dispersed with a paint shaker for 2 hours to obtain a colored composition 12.
  • Coloring composition 12 4.0 parts, Unidic ZL-295 0.98 parts, propylene glycol monomethyl ether acetate 0.22 parts are added and mixed with a paint shaker to form a green pixel part for a color filter A composition for evaluation 12 was obtained.
  • This evaluation composition 12 was spin-coated on soda glass and dried at 90 ° C. for 3 minutes to obtain an evaluation glass substrate.
  • the monochromatic spectral transmission spectrum of this glass substrate for evaluation was measured using U-3900 manufactured by Hitachi High-Technologies Corporation. Spectral transmission spectra are shown in FIGS. 1A, 1B and 1C.
  • the compositions for evaluation 1 to 7 had transmittances of 555 nm of 50.47%, 50.28%, 47.41%, 45.73%, 46. They were 45%, 50.07%, and 45.89%, and were 45% or more. Further, the ratio of the transmittance at a wavelength of 505 nm to the transmittance at a wavelength of 555 nm ((A) / (B)) is 1.40, 1.44, 1.53, 1.57, 1.56, 1.42, and 1.59, 1.4 or more.
  • the half widths were 73 nm, 75 nm, 73 nm, 68 nm, 68 nm, 71 nm and 68 nm, and were 80 nm or less.
  • Table 2 shows a summary of the halogen ratio in one molecule of zinc halide phthalocyanine of pigments 1 to 3.
  • pigments 1 to 3 From Table 2, in pigments 1 to 3, the average number of bromine atoms was 14.13, 13.59, and 13.36 in one molecule of zinc halide phthalocyanine, which was in the range of 13 to 15. In addition, the average number of chlorine atoms in one molecule of zinc halide phthalocyanine was 1.60, 1.71, and 1.74, which was in the range of 1 to 3. Further, the ratio of the average number of bromine atoms to the average number of chlorine atoms in one molecule of zinc halide phthalocyanine ((E) / (F)) was 8.83, 7.94, and 7.69, which was 7 or more. It was. Due to the halogen ratio, pigments 1 to 3 can be green pigments having higher brightness than pigment green 58 and 59, which are conventional green pigments, while maintaining a green hue.
  • a color filter having higher luminance than the conventional one can be formed by using a green pigment having specific spectral characteristics.
  • the pigment composition for a color filter of the present embodiment it is possible to provide a high-intensity color filter that can supplement the characteristics of B-YAG, which is a backlight having a weak green emission intensity. Moreover, since the green pixel formed using the pigment composition for color filters of this embodiment has high brightness

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Abstract

La présente invention concerne : une nouvelle composition de pigments pour filtres colorés, qui est capable de former un filtre coloré ayant une forte luminance ; et un filtre coloré qui contient cette composition de pigments pour filtres colorés. Cette composition de pigments pour filtres colorés contient un pigment vert qui présente des caractéristiques spectrales de telle sorte que la transmittance à la longueur d'onde de 555 nm est 45 % ou plus, le rapport de la transmittance à la longueur d'onde de 505 nm sur la transmittance à la longueur d'onde de 555 nm, à savoir T(505 nm)/T(555 nm) est 1,40 ou plus et la largeur à demi-valeur est 80 nm ou moins, si elle est formée dans un film de revêtement dans lequel la transmittance spectrale à la longueur d'onde de transmission maximale est de 80 %. Un filtre coloré selon la présente invention contient cette composition de pigments pour filtres colorés.
PCT/JP2017/031119 2016-08-31 2017-08-30 Composition de pigments pour filtres colorés, et filtre coloré WO2018043548A1 (fr)

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CN113272389A (zh) * 2020-09-02 2021-08-17 Dic株式会社 彩色滤光片用颜料的制造方法
JPWO2022004261A1 (fr) * 2020-07-01 2022-01-06
WO2022080002A1 (fr) * 2020-10-15 2022-04-21 Dic株式会社 Pigment pour filtre couleur, composition de coloration et filtre couleur

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JPWO2022004261A1 (fr) * 2020-07-01 2022-01-06
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CN113272389A (zh) * 2020-09-02 2021-08-17 Dic株式会社 彩色滤光片用颜料的制造方法
JPWO2022080002A1 (fr) * 2020-10-15 2022-04-21
WO2022080002A1 (fr) * 2020-10-15 2022-04-21 Dic株式会社 Pigment pour filtre couleur, composition de coloration et filtre couleur
JP7236567B2 (ja) 2020-10-15 2023-03-09 Dic株式会社 カラーフィルタ用顔料、着色組成物、及びカラーフィルタ

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