Pigment dispersant, pigment composition, and pigment colorant

Abstract

To provide a pigment dispersant which can remarkably improve fluidity of a liquid product such as ink or a coating composition containing pigment particles such as a black azo pigment in a dispersed state and suppress agglomeration of pigment particles and can produce a colored article excellent in optical density while suppressing the generation of a foreign matter and to provide a pigment composition using the same and a pigment coloring agent.SOLUTION: There are provided: a pigment dispersant which is a compound represented by the following general formula (1), a quaternary ammonium salt thereof, an amine salt thereof or a metal salt thereof; a pigment composition comprising the pigment dispersant; and a pigment coloring agent (wherein, X represents an aromatic group which may have a substituent).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a pigment dispersant, a pigment composition, and a pigment colorant. More specifically, the present invention relates to a pigment dispersant that is blended in printing inks (offset inks, gravure inks, etc.), various coating materials, plastics, pigment printing agents, dry toners for electrophotography, wet toners for electrophotography, inkjet recording inks, thermal transfer recording inks, resists for color filters, inks for writing instruments, and the like. [Background technology]

[0002] In general, it is difficult to mix and disperse pigments (particles) in a stable state in vehicles such as paints, gravure inks, and offset inks. For example, fine pigment particles once dispersed in a vehicle tend to aggregate in the vehicle. When pigment particles aggregate, the viscosity of the vehicle increases. In addition, when a vehicle containing pigment particles in an aggregated state is used, various problems such as a decrease in the coloring power of the ink or paint and a decrease in the gloss of the coating film are likely to occur. Among pigments, it is particularly difficult to mix and disperse black pigments in a stable state.

[0003] Carbon black pigments, iron oxide pigments, etc. are commonly used as black pigments for colorants in paints, printing inks, plastics, etc. These black pigments exhibit their black color by absorbing all light rays, including those in the visible light range, of sunlight.

[0004] Sunlight is an electromagnetic wave, and light in the wavelength range of approximately 380nm to 780nm is visible light. For this reason, simply absorbing all visible light will result in black. Light in the wavelength range of 0.8μm to 2.5μm (800nm ​​to 2,500nm), which is longer than visible light and lies between the infrared range, is called near-infrared light. Carbon black pigments also absorb this near-infrared light. In the wavelength range of sunlight, it is said that light in the wavelength range of 800nm ​​to 1,400nm, among the near-infrared light, contributes particularly greatly to heat.

[0005] As described above, black pigments such as carbon black pigments also absorb near-infrared radiation in the wavelength range of 800 nm to 1,400 nm, which contributes greatly to heat. For this reason, there is a problem that articles colored with black pigments tend to heat up when exposed to sunlight. There are many sophisticated products colored with black pigments, such as black matrices (hereinafter, also simply referred to as "BM") that constitute color filters (hereinafter, also simply referred to as "CF"). For this reason, various studies have been conducted on black pigments that do not heat up even when exposed to sunlight and colorant compositions that color various articles black.

[0006] Patent Document 1 discloses a black azo pigment having an azomethine group that absorbs visible light, assumes a black color, and reflects infrared light. In addition, since the pigment reflects infrared light, it has been proposed to obtain an article that does not excessively heat up even when exposed to direct sunlight by coloring the article with the black azo pigment.

[0007] Incidentally, with the remarkable development of information devices in recent years, liquid crystal color displays (hereinafter, simply referred to as "LCDs") are being applied as information display components to many information display related devices. Accordingly, there is a demand for improved display quality and lower costs for LCDs. For this reason, the CFs mounted on LCDs are also required to have better quality in terms of color characteristics and optical characteristics such as definition, color density, light transmittance, and contrast.

[0008] In CF, R (red), G (green), and B (blue) pixels are arranged in a stripe, mosaic, or triangle pattern, and a grid-like BM is formed around each pixel to block unnecessary light. Then, light is irradiated from the backside by a backlight, and an image is formed by additively mixing the transmitted light of each of the R, G, and B pixels. For the chromatic color (RGB) pixels, red pigments, green pigments, blue pigments, yellow pigments, purple pigments, etc. are used, and each of them has been improved. In addition, the light-shielding material that constitutes the BM is shifting from the conventional metal chrome film to a resin film using a black pigment in order to respond to the increase in substrate size and the reduction of environmental load.

[0009] In addition, various improvements have been proposed for the display method of CF pixels, and the light-shielding black pigment used in the BM has also been improved. For example, in order to widen the viewing angle, the in-plane switching method (IPS method) has been proposed, in which an electric field is applied parallel to the substrate to convert the liquid crystal layer and display pixels. In addition, the black matrix-on-array method (BOA method) and the color filter-on-array method (COA method) have been proposed, in which the BM is formed on a thin film transistor (TFT). These methods can increase the pixel area because of the higher aperture ratio. Furthermore, the efficiency of the lamination process is improved, so the work process can be streamlined.

[0010] For example, in order to widen the viewing angle in the IPS mode, it is necessary to keep the distance (cell gap) between the substrates sandwiching the liquid crystal layer constant with high precision. However, it is difficult to adjust the cell gap uniformly using the conventional method of scattering bead-like spacers. For this reason, methods have been proposed for adjusting the cell gap uniformly, such as thickening the BM itself, or laminating a resin that supports the distance, such as a colored layer or a photoresist layer, on the BM to make it thicker. Furthermore, these methods do not use conventional bead-like spacers, and are therefore said to be able to suppress degradation of display quality due to light scattering and transmission (Patent Documents 2 and 3).

[0011] In the IPS, BOA, and COA types, the BM is formed on the active element such as TFT, so if the BM is not electrically insulating, the active element may malfunction. Carbon black pigments, which have been used conventionally as light-blocking black pigments, have low electrical resistance and are therefore not suitable as black pigments for the above types. Therefore, there is a demand for light-blocking black pigments with better electrical insulation.

[0012] In response to such demands, for example, a black pigment for BM has been proposed in which carbon black with a specified oxygen content is coated with a highly insulating resin film to improve electrical insulation (Patent Document 4). It has also been proposed to apply to the COA method a BM formed using insulating carbon black selected by measuring the volume resistivity, or carbon black coated with resin to improve electrical insulation (Patent Document 5). However, because carbon black pigments are essentially conductive materials, it has been difficult to ensure sufficient insulation even when coated with resin.

[0013] On the other hand, in order to ensure the insulating properties of the BM, it has been proposed to use the black azo pigment proposed in Patent Document 1 (Patent Document 6). However, it was difficult to stably mix and disperse the black azo pigment proposed in Patent Document 1 in a vehicle. Fine pigment particles once dispersed in a vehicle tend to aggregate in the vehicle. Then, the viscosity of the vehicle in which the pigment particles have aggregated increases. In addition, when a vehicle containing aggregated pigment particles is used, problems such as a decrease in the coloring power of the ink or paint, a decrease in the gloss of the coating film, or insufficient optical density as a light-shielding material forming the BM arise.

[0014] In order to stably disperse pigment particles such as black azo pigments in a dispersion medium, methods of using pigment derivatives as dispersants and methods of using pigments treated with pigment derivatives have been proposed. Specifically, when a phthalocyanine pigment such as PB15:6 is used, it has been proposed to use a substituted derivative of phthalocyanine as a pigment dispersant (Patent Document 7). In addition, when an anthraquinone pigment such as PR177 is used, it has been proposed to use a substituted derivative of anthraquinone as a pigment dispersant (Patent Document 8). Furthermore, when a diketopyrrolopyrrole pigment such as PR254 is used, it has been proposed to use a substituted derivative of diketopyrrolopyrrole as a pigment dispersant (Patent Document 8). [Prior art documents] [Patent documents]

[0015] [Patent Document 1] Special Publication No. 4-15265 [Patent Document 2] JP 2000-66018 A [Patent Document 3] JP 2002-341332 A [Patent Document 4] Patent No. 3543501 [Patent Document 5] Patent No. 4338479 [Patent Document 6] Patent No. 2819512 [Patent Document 7] JP 2002-55224 A [Patent Document 8] JP 2001-240780 A Summary of the Invention [Problem to be solved by the invention]

[0016] However, even when the pigment derivatives proposed in Patent Documents 7 and 8 were used, it was difficult to stably disperse the black azo pigment proposed in Patent Document 1 in a medium. In addition, the color tone of the pigment derivatives proposed in Patent Documents 7 and 8 was not black, and there was also a problem of a decrease in the optical density of the black color.

[0017] The present invention has been made in consideration of the problems of the prior art, and an object of the present invention is to provide a pigment dispersant that can significantly improve the fluidity of liquids such as inks and paints that contain pigment particles such as a black azo pigment in a dispersed state, can suppress the aggregation of pigment particles, and can produce colored articles with excellent optical density while preventing the generation of foreign matter. Another object of the present invention is to provide a pigment composition and a pigment colorant obtained by using the above pigment dispersant. [Means for solving the problem]

[0018] That is, according to the present invention, there is provided a pigment dispersant as shown below. [1] A pigment dispersant which is a compound represented by the following general formula (1), a quaternary ammonium salt thereof, an amine salt thereof, or a metal salt thereof:

[0019] TIFF0007607526000001.tif44170 (In the general formula (1), X represents an aromatic group which may have a substituent.)

[0020] [2] The pigment dispersant according to the above [1], wherein X in the general formula (1) is each independently represented by any one of the following general formulae (1-a) to (1-c):

[0021] TIFF0007607526000002.tif49170 (In the general formulae (1-a) to (1-c), * indicates a bonding position with a nitrogen atom. In the general formula (1-a), R1 indicates an aromatic group which may have a substituent. In the general formula (1-b), R2 indicates an aromatic group which may have a substituent. In the general formula (1-c), R3 and R4 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, or a sulfonamide group, and m and n each independently represent a number from 0 to 5, and m+n is 5 or less.)

[0022] According to the present invention, there is also provided a pigment composition as described below. [3] A pigment composition comprising a pigment and the pigment dispersant described in [1] or [2] above. [4] The pigment composition according to [3], wherein the content of the pigment dispersant is 0.5 to 40 parts by mass relative to 100 parts by mass of the pigment.

[0023] Further, according to the present invention, there is provided the following pigment colorant. [5] A pigment colorant comprising the pigment composition according to [3] or [4] above and a film-forming material. [6] The pigment colorant according to [5] above, which is for use in image display, image recording, gravure printing ink, writing ink, plastics, pigment textile printing, paint, or the black matrix of a color filter. Effect of the Invention

[0024] According to the present invention, it is possible to provide a pigment dispersant that can significantly improve the fluidity of liquids such as inks and paints that contain pigment particles such as a black azo pigment in a dispersed state, suppress the aggregation of pigment particles, and prevent the generation of foreign matter while producing colored articles with excellent optical density. Furthermore, according to the present invention, it is possible to provide a pigment composition and a pigment colorant obtained by using the above pigment dispersant. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] <Pigment dispersant> The present invention will be described in detail below, taking preferred embodiments as examples. One of the main characteristics of the pigment dispersant of the present invention is that it is a compound represented by the following general formula (1). The pigment dispersant of the present invention having such characteristics has excellent affinity for various pigments and can be suitably used as a pigment dispersant for dispersing various pigments, whether organic or inorganic. In addition, since the pigment dispersant of the present invention has an excellent pigment dispersing effect, it can be used as a material for preparing pigment colorants for various applications.

[0026] TIFF0007607526000003.tif44170 (In the general formula (1), X represents an aromatic group which may have a substituent.)

[0027] In general formula (1), X is preferably, independently of each other, a group represented by any one of the following general formulae (1-a) to (1-c).

[0028] TIFF0007607526000004.tif49170 (In the general formulae (1-a) to (1-c), * indicates a bonding position with a nitrogen atom. In the general formula (1-a), R1 indicates an aromatic group which may have a substituent. In the general formula (1-b), R2 indicates an aromatic group which may have a substituent. In the general formula (1-c), R3 and R4 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, or a sulfonamide group, and m and n each independently represent a number from 0 to 5, and m+n is 5 or less.)

[0029] The pigment dispersant of the present invention exhibits an excellent effect as a pigment dispersant even in a small amount. In addition, the pigment composition and pigment colorant prepared using the pigment dispersant of the present invention are less likely to thicken or gel during storage, and are less likely to generate foreign matter in the coating film formed using them. Specific examples of the pigment dispersant of the present invention include compounds represented by the following formulas (A) to (F).

[0030] TIFF0007607526000005.tif175170

[0031] TIFF0007607526000006.tif206170

[0032] Further specific examples of the pigment dispersant of the present invention include compounds represented by the following formulas (1-1) to (1-18).

[0033] TIFF0007607526000007.tif228170

[0034] TIFF0007607526000008.tif240170

[0035] TIFF0007607526000009.tif208170

[0036] TIFF0007607526000010.tif185170

[0037] TIFF0007607526000011.tif217170

[0038] The compound (pigment dispersant) represented by the general formula (1) can be synthesized, for example, as follows. 5-amino-2-[(4-aminophenyl)amino]benzenesulfonic acid is tetrazotized by a conventional method using hydrochloric acid and sodium nitrite. Then, the compound (pigment dispersant) represented by the general formula (1) can be obtained by coupling reaction with naphthalenecarboxamides, 2-hydroxy-11H-benzo[a]carbazole-3-carboxamides, or 3-methyl-1-phenyl-5-pyrazolones. The pigment dispersant of the present invention may contain small amounts of unreacted raw materials and by-products, but as long as the effects of the present invention are obtained, these unreacted raw materials and by-products may be contained in small amounts.

[0039] The naphthalene carboxamides used in the above synthesis method include N-phenyl-3-hydroxy-2-naphthalene carboxamide, N-(2-methylphenyl)-3-hydroxy-2-naphthalene carboxamide, N-(4-methylphenyl)-3-hydroxy-2-naphthalene carboxamide, N-(2-methoxyphenyl)-3-hydroxy-2-naphthalene carboxamide, N-(4-chlorophenyl)-3-hydroxy-2-naphthalene carboxamide, and N-(3-nitrophenyl)- 3-Hydroxy-2-naphthalenecarboxamide, N-(4-methoxyphenyl)-3-hydroxy-2-naphthalenecarboxamide, N-(2-ethoxyphenyl)-3-hydroxy-2-naphthalenecarboxamide, N-(2,5-dimethoxyphenyl)-3-hydroxy-2-naphthalenecarboxamide, N-(2-methoxy-5-nitrophenyl)-3-hydroxy-2-naphthalenecarboxamide, N-(2-methyl-5-chlorophenyl)-3-hydroxy-2-naphthalenecarboxamide amide, N-(2-methyl-4-chlorophenyl)-3-hydroxy-2-naphthalenecarboxamide, N-(5-chloro-2,4-dimethoxyphenyl)-3-hydroxy-2-naphthalenecarboxamide, N-[(2,3-dihydro-2-oxo-1H-benzimidazol)-5-yl]-3-hydroxy-2-naphthalenecarboxamide, N-(2,3-dihydro-1,3-dioxo-1H-isoindol-5-yl)-3-hydroxy-2-naphthalenecarboxamide, N-(4-chlorophenyl)-3-hydroxy-2-naphthalenecarboxamide, Examples of the hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide include N-(2-methoxy-5-chlorophenyl)-3-hydroxy-2-naphthalenecarboxamide, N-(1-naphthyl)-2-naphthalenecarboxamide, 3-hydroxy-N-(2-naphthyl)-2-naphthalenecarboxamide, and N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-hydroxy-2-naphthalenecarboxamide.

[0040] The 2-hydroxy-11H-benzo[a]carbazole-3-carboxamides used in the above synthesis method include 2-hydroxy-N-phenyl-11H-benzo[a]carbazole-3-carboxamide, 2-hydroxy-N-(4-methoxyphenyl)-11H-benzo[a]carbazole-3-carboxamide, 2-hydroxy-N-(4-methoxy-2-methylphenyl)-11H-benzo[a]carbazole-3-carboxamide, 2-hydroxy-N -(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-11H-benzo[a]carbazole-3-carboxamide, N-(1,3-dioxoisoindolin-5-yl)-2-hydroxy-11H-benzo[a]carbazole-3-carboxamide, N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-2-hydroxy-11H-benzo[a]carbazole-3-carboxamide, and the like.

[0041] Examples of the 3-methyl-1-phenyl-5-pyrazolones used in the above synthesis method include 3-methyl-1-phenyl-5-pyrazolone, 3-methyl-1-p-tolyl-5-pyrazolone, 1-(3,4-dimethylphenyl)-3-methyl-5-pyrazolone, 1-(4-chlorophenyl)-3-methyl-5-pyrazolone, 1-(2-chlorophenyl)-3-methyl-5-pyrazolone, 1-(4-nitrophenyl)-3-methyl-5-pyrazolone, and 3-methyl-1-(3'-sulfamidophenyl)-5-pyrazolone.

[0042] The method of using the pigment dispersant of the present invention is not particularly limited, but examples of the method of use are as follows. In any case, the desired pigment dispersion effect can be obtained. (1) A pigment and a pigment dispersant are mixed in advance by a known method, and the resulting pigment composition is added to a vehicle or the like to disperse the pigment in the vehicle. (2) A pigment and a pigment dispersant are added separately to a vehicle or the like in a specified ratio to disperse the pigment in the vehicle. (3) The pigment and the pigment dispersant are separately dispersed in a vehicle or the like, and then the resulting dispersions are mixed in a predetermined ratio to disperse the pigment in the vehicle. (4) A pigment dispersant is added in a prescribed ratio to a dispersion obtained by dispersing the pigment in a vehicle or the like, thereby dispersing the pigment in the vehicle.

[0043] <Pigment composition> The pigment composition of the present invention contains a pigment and the above-mentioned pigment dispersant. The amount of the pigment dispersant to be blended relative to 100 parts by mass of the pigment is preferably 0.5 to 40 parts by mass, more preferably 1 to 20 parts by mass. If the amount of the pigment dispersant is less than the above range, the intended effect of the dispersant may not be fully obtained. On the other hand, if the amount of the pigment dispersant is more than the above range, the effect of the dispersant may reach a plateau, and no further effect may be expected, and the cost of the material may become high, which may be disadvantageous in terms of productivity. Furthermore, in paints and inks using a pigment composition containing such an excessive amount of pigment dispersant, the physical properties of the vehicle may be reduced, and the hue of the pigment may change significantly depending on the color of the pigment dispersant itself.

[0044] Specific examples of pigments for which an effective dispersion effect can be obtained by using the pigment dispersant of the present invention include anthraquinone pigments, quinacridone pigments, diketopyrrolopyrrole pigments, indigo / thioindigo pigments, perinone pigments, perylene pigments, phthalocyanine pigments, indoline pigments, isoindoline pigments, isoindolinone pigments, dioxazine pigments, quinophthalone pigments, nickel azo pigments, metal complex pigments, insoluble azo pigments, soluble azo pigments, high molecular weight azo pigments, aniline black pigments, azo black pigments, etc. Among them, when used with azo black pigments with a black hue, a more remarkable effect can be obtained, so that it is preferable.

[0045] Specific examples of azo black pigments having a black hue include compounds represented by the following formulas (a1) to (a7) (black azo pigments (1) to (7)).

[0046] TIFF0007607526000012.tif166170

[0047] TIFF0007607526000013.tif208170

[0048] The method for producing the pigment composition of the present invention is not particularly limited. For example, the pigment composition of the present invention can be obtained by mixing the pigment and the pigment dispersant by a conventionally known method. Specific examples of the method for producing the pigment composition of the present invention include the following methods (1) to (4). (1) A method in which pigment powder and pigment dispersant powder are mixed without using a disperser. (2) A method in which the pigment and the pigment dispersant are mechanically mixed using various dispersing machines such as a kneader, a roll, an attritor, or a horizontal bead mill. (3) A method in which a liquid in which a pigment dispersant is dissolved or finely dispersed is added to and mixed with an aqueous or organic solvent-based suspension of the pigment, thereby depositing the pigment dispersant uniformly on the surface of the pigment. (4) A method in which a pigment and a pigment dispersant are dissolved in a solvent with strong dissolving power such as sulfuric acid, and then co-precipitated with a poor solvent such as water.

[0049] The pigment dispersant used to prepare the pigment composition may be in the form of a solution, a slurry, a paste, or a powder. Regardless of the form of the pigment dispersant used, the desired effect can be obtained.

[0050] Here, a pigment composition containing a black azo pigment having optical properties of transmitting light in the infrared region, particularly light in the near-infrared region, well and shielding light in the visible light region, and the above-mentioned pigment dispersant will be described. This pigment composition can be suitably used, for example, in an infrared filter mounted on an electronic device that uses infrared rays. In addition, since the printed characters of this pigment composition transmit near-infrared rays without absorbing them, it can also be suitably used, for example, in PTP (press-through pack) packaging inks in which printed characters on aluminum packaging materials do not interfere with foreign matter detection. Furthermore, the above-mentioned black azo pigment has excellent electrical insulation properties, unlike conductive materials such as carbon black. For this reason, the pigment composition containing this black azo pigment and the above-mentioned pigment dispersant is also suitable, for example, as a material for forming a black matrix (BM) of a color filter (CF).

[0051] <Pigment colorants> The pigment colorant of the present invention contains the above-mentioned pigment composition and a film-forming material. The pigment colorant of the present invention can be used in a wide range of fields, such as colorants for image display, image recording, gravure printing ink, writing ink, plastics, pigment printing, and paint. In particular, the pigment colorant of the present invention is suitable as a colorant for the black matrix of a color filter. Furthermore, the pigment colorant of the present invention is particularly useful as a material for image recording materials such as gravure printing ink. By using the pigment colorant of the present invention, a material for an image recording material that can provide a high-quality image can be prepared.

[0052] The amount of the pigment composition in the pigment colorant of the present invention is preferably 5 to 500 parts by mass, and more preferably 50 to 250 parts by mass, based on 100 parts by mass of the film-forming material. The pigment colorant of the present invention can be prepared, for example, by mixing a finely divided pigment with a film-forming material such as a resin ((co)polymer), an oligomer, or a monomer.

[0053] The pigment colorant of the present invention can also be prepared by mixing the pigment composition with a liquid containing the above-mentioned film-forming material. As the liquid containing the film-forming material, a liquid containing a photosensitive film-forming material or a liquid containing a non-photosensitive film-forming material can be used. Specific examples of the liquid containing the photosensitive film-forming material include a liquid containing a photosensitive film-forming material used in ultraviolet-curable inks and electron beam-curable inks. Specific examples of the liquid containing a non-photosensitive film-forming material include varnishes used in printing inks such as letterpress inks, lithographic inks, gravure inks, and screen inks; varnishes used in room temperature drying or baking paints; varnishes used in electrodeposition coating; varnishes used in thermal transfer ribbons, etc.

[0054] Specific examples of photosensitive film-forming materials include photosensitive resins such as photosensitive cyclized rubber resins, photosensitive phenol resins, photosensitive polyacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, unsaturated polyester resins, polyester acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, polyol acrylate resins, etc. Various monomers may be added as reactive diluents to the liquid containing these photosensitive resins.

[0055] A photopolymerization initiator such as benzoin ether or benzophenone can be added to a pigment colorant containing a photosensitive resin as a film-forming material, and the mixture can be kneaded by a conventional method to obtain a photocurable photosensitive pigment dispersion. A thermosetting pigment dispersion can be obtained by using a thermal polymerization initiator instead of the photopolymerization initiator.

[0056] Specific examples of non-photosensitive film-forming materials include styrene-(meth)acrylic acid ester copolymers, soluble polyamide resins, soluble polyimide resins, soluble polyamideimide resins, soluble polyesterimide resins, water-soluble amino polyester resins, water-soluble salts thereof, water-soluble salts of styrene-maleic acid ester copolymers, and water-soluble salts of (meth)acrylic acid ester-(meth)acrylic acid copolymers.

[0057] The pigment colorant of the present invention may further contain a polymer dispersant. As the polymer dispersant, an acidic polymer dispersant or a basic polymer dispersant may be used. The blending amount of the polymer dispersant is preferably 2 to 100 parts by mass, more preferably 10 to 50 parts by mass, based on 100 parts by mass of the pigment.

[0058] Next, further details of the pigment colorant of the present invention will be described using a pigment dispersion liquid for the black matrix of a color filter (pigment colorant for BM) as a representative example. To prepare a pigment colorant for BM (photoresist), first, the above-mentioned pigment composition containing a black pigment such as a black azo pigment is added to a liquid containing a film-forming material and premixed. Then, by performing a dispersion treatment, a pigment colorant for BM can be obtained. More specifically, a pigment composition that has been uniformly ground using a dispersion machine such as a vertical media disperser, a horizontal media disperser, or a ball mill can be added to and mixed with a liquid containing a film-forming material to obtain a pigment colorant for BM. In addition, a solution obtained by dissolving a black azo pigment and a pigment dispersant in sulfuric acid or the like is mixed with water to precipitate a pigment composition containing a black azo pigment and a pigment dispersant as a solid solution or a co-eutectoid and separated. A pigment colorant for BM can also be obtained by adding the separated pigment composition to a liquid containing a film-forming material, a polymer dispersant, etc., mixing it, and then grinding and dispersing it using a horizontal wet media disperser (beads mill) such as a dyno mill.

[0059] As the liquid containing a film-forming material used to prepare the pigment colorant for BM, a solution of a film-forming polymer contained in a conventionally known pigment dispersion for color filters can be used. In addition, as the liquid medium used in the liquid containing the film-forming material, an organic solvent, water, and a mixture of an organic solvent and water can be mentioned. In addition, conventionally known additives such as a dispersing agent, a smoothing agent, and an adhesion agent can be added to the pigment colorant for BM as necessary.

[0060] By using the above-mentioned pigment colorant for BM containing a black azo pigment dispersed with a pigment dispersant, a black matrix (BM) for a CF substrate that is substantially electrically insulating can be formed. The BM can be formed on a CF substrate by, for example, a photolithography method, a laser ablation method, an inkjet printing method, a printing method, a transfer method, or a bonding method using the pigment colorant for BM.

[0061] The thickness of the BM is, for example, 0.5 to 3 μm, and usually 1 to 2 μm. In addition, by using the above-mentioned pigment colorant for BM, a BM with sufficient optical density can be formed. The optical density of the formed BM can be, for example, 1.6 or more, and preferably 2.0 or more. Specific methods for making the BM function as a spacer include a method of forming the BM itself thick; a method of stacking pixels on the BM; and a method of stacking a colorless resin film on the BM. In any method, the thickness is preferably about 5 to 10 μm. Then, by using a known colorant for forming chromatic pixels, chromatic pixels can be further formed on the CF substrate on which the BM has been formed. EXAMPLES

[0062] The present invention will now be described in more detail with reference to examples and comparative examples. In the following, "parts" and "%" are by weight unless otherwise specified.

[0063] <Preparation of pigment dispersant> Example 1 A solution was prepared by dissolving 18.8 parts of 3-hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide and 7.2 parts of sodium hydroxide in 400 parts of methanol. 8.4 parts of 5-amino-2-[(4-aminophenyl)amino]benzenesulfonic acid were diazotized in a conventional manner using 18.8 parts of 35% hydrochloric acid and 4.5 parts of sodium nitrite to obtain a diazonium salt solution. The diazonium salt solution was added to the prepared solution, and a coupling reaction was carried out at 20 to 30°C for 5 hours. After filtration and washing with water, the mixture was dried to obtain 25.1 parts of a blue-purple pigment dispersant (A) represented by the following formula (A).

[0064] TIFF0007607526000014.tif55170

[0065] Mass spectrometry using MALDI (matrix-assisted laser desorption / ionization) detected a peak with a molecular weight of 927.98. The purity was measured using high performance liquid chromatography (MODEL860-CO (JAPAN SPECTRAL), column: YMCPack Pro C18 (YMC)) and was 92%. From the raw materials used, the results of mass spectrometry, and the results of high performance liquid chromatography, it was confirmed that a compound with the desired structure was obtained.

[0066] Example 2 Except for using 23.6 parts of N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-hydroxy-2-naphthalenecarboxamide instead of 18.8 parts of 3-hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide, the same procedure as in Example 1 was repeated to obtain 29.2 parts of a blue-purple pigment dispersant (B) represented by the following formula (B).

[0067] TIFF0007607526000015.tif55170

[0068] Mass spectrometry using MALDI detected a peak with a molecular weight of 1088.06. The purity measured using high performance liquid chromatography was 89%. From the raw materials used, the results of mass spectrometry, and the results of high performance liquid chromatography, it was confirmed that a compound with the desired structure was obtained.

[0069] Example 3 Except for using 22.9 parts of 2-hydroxy-N-(4-methoxyphenyl)-11H-benzo[a]carbazole-3-carboxamide instead of 18.8 parts of 3-hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide, the same procedure as in Example 1 was repeated to obtain 28.9 parts of a blue-purple pigment dispersant (C) represented by the following formula (C).

[0070] TIFF0007607526000016.tif59170

[0071] Mass spectrometry using MALDI detected a peak with a molecular weight of 1066.1. The purity measured using high performance liquid chromatography was 93%. From the raw materials used, the results of mass spectrometry, and the results of high performance liquid chromatography, it was confirmed that a compound with the desired structure was obtained.

[0072] Example 4 Except for using 23.8 parts of 2-hydroxy-N-(4-methoxy-2-methylphenyl)-11H-benzo[a]carbazole-3-carboxamide instead of 18.8 parts of 3-hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide, the same procedure as in Example 1 was repeated to obtain 29.5 parts of a blue-purple pigment dispersant (D) represented by the following formula (D).

[0073] TIFF0007607526000017.tif61170

[0074] Mass spectrometry using MALDI detected a peak with a molecular weight of 1094.16. The purity measured using high performance liquid chromatography was 96%. From the raw materials used, the results of mass spectrometry, and the results of high performance liquid chromatography, it was confirmed that a compound with the desired structure was obtained.

[0075] Example 5 Except for using 10.5 parts of 3-methyl-1-phenyl-5-pyrazolone instead of 18.8 parts of 3-hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide, the same procedure as in Example 1 was repeated to obtain 17.7 parts of a blue-purple pigment dispersant (E) represented by the following formula (E).

[0076] TIFF0007607526000018.tif65170

[0077] Mass spectrometry using MALDI detected a peak with a molecular weight of 649.68. The purity measured using high performance liquid chromatography was 96%. From the raw materials used, the results of mass spectrometry, and the results of high performance liquid chromatography, it was confirmed that a compound with the desired structure was obtained.

[0078] Example 6 Except for using 11.3 parts of 3-methyl-1-p-tolyl-5-pyrazolone instead of 18.8 parts of 3-hydroxy-N-(1-naphthyl)-2-naphthalenecarboxamide, the same procedure as in Example 1 was repeated to obtain 19.2 parts of a blue-violet pigment dispersant (F) represented by the following formula (F).

[0079] TIFF0007607526000019.tif73170

[0080] Mass spectrometry using MALDI detected a peak with a molecular weight of 677.73. The purity measured using high performance liquid chromatography was 93%. From the raw materials used, the results of mass spectrometry, and the results of high performance liquid chromatography, it was confirmed that a compound with the desired structure was obtained.

[0081] <Preparation of black pigment dispersion> Example 7 [Preparation of fine powder of black pigment] In a kneader equipped with a pressure lid, 100 parts of the black azo pigment (1) represented by formula (a1) (product name "Chromofine Black A1103", manufactured by Dainichiseika Color & Chemicals Mfg. Co., Ltd.), 500 parts of sodium chloride powder, and 50 parts of diethylene glycol were charged. After premixing until a uniformly moistened mass was formed, the pressure lid was closed and the mixture was mixed under a pressure of 6 kg / cm. 2 The contents were kneaded and milled for 2 hours while controlling the temperature to 92-98°C while pressing down with a pressure was applied. The milled product obtained was placed in 3,000 parts of water heated to 80°C and stirred for 1 hour, then filtered and washed with water to remove sodium chloride and diethylene glycol, to obtain a press cake. A nonionic surfactant (200% of the pigment) was added to the press cake obtained and diluted with water, followed by ultrasonic dispersion treatment to prepare a pigment dispersion. The average particle size of the fine particles in the pigment dispersion, measured using a particle size measuring device (product name "Model N-4", manufactured by Coulter), was about 90 nm. The press cake was dried and pulverized to obtain a fine powder of the black pigment.

[0082] [Preparation of black pigment dispersion] 25 parts of finely divided black pigment powder, 1.5 parts of the pigment dispersant (A) obtained in Example 1, 10 parts of benzyl methacrylate / methacrylic acid / 2-hydroxyethyl methacrylate copolymer (molar ratio: 60 / 20 / 20, weight average molecular weight 30,000), 5.5 parts of a basic polymer dispersant (product name "DISPERBYK-2001", manufactured by BYK-Chemie, solid content 46%), and 65 parts of propylene glycol-1-monomethyl ether-2-acetate were mixed. After premixing, the mixture was dispersed using a horizontal bead mill to obtain a black pigment dispersion (Example 7).

[0083] (Examples 8 to 12) Black pigment dispersions (Examples 8 to 12) were obtained in the same manner as in Example 7 above, except that pigment dispersants (B) to (F) were used instead of the pigment dispersant (A).

[0084] Comparative Example 1 A black pigment dispersion (Comparative Example 1) was obtained in the same manner as in Example 7 above, except that the pigment dispersant (A) was not used.

[0085] Comparative Example 2 A black pigment dispersion (Comparative Example 2) was obtained in the same manner as in Example 7, except that pigment dispersant (G) (phthalocyanine sulfonate (product name "SOLSPERS-12000", manufactured by Lubrizol)) was used instead of pigment dispersant (A).

[0086] <Evaluation> The black pigment dispersions thus obtained were evaluated for (1) fluidity (storage stability), (2) gloss of the applied surface, and (3) foreign matter in the coating film. The evaluation methods are shown below. The evaluation results are shown in Table 1.

[0087] (1) Fluidity (storage stability) An E-type viscometer was used to measure the viscosity (mPa s) of the black pigment dispersion immediately after preparation (initial) and after leaving it at 25°C for one month (after leaving it). The measurement conditions were temperature: room temperature (25°C) and rotor rotation speed: 6 rpm. Then, "viscosity after leaving it / initial viscosity (%)" was calculated and "storage stability" was evaluated according to the following criteria. ○: "Viscosity after standing / initial viscosity" is 110% or less ×: "Viscosity after standing / initial viscosity" is over 110%

[0088] (2) Gloss of the applied surface The black pigment dispersion was spread on a polypropylene film using a bar coater (winding wire thickness 0.45 mm) to form a spread surface. The gloss of the spread surface was observed visually and with a gloss meter, and the "gloss of the spread surface" was evaluated according to the following criteria. The higher the gloss of the spread surface, the better it was judged to be. ◎: Very good ○: Good ×: Bad

[0089] (3) Foreign matter in the coating film The black pigment dispersion was applied to a glass substrate using a spinner. After drying at 90 °C for 2 minutes, it was heated at 230 °C for 30 minutes to form a coating film. The surface (coating surface) of the formed coating film was observed using a microscope (200 times magnification) to confirm the presence or absence of foreign matter, and "foreign matter in the coating film" was evaluated according to the criteria shown below. ◎: No foreign matter ○: Slight foreign matter ×: Foreign matter

[0090] TIFF0007607526000020.tif77170

[0091] (Examples 13 to 48) Black pigment dispersions (Examples 13 to 48) were obtained in the same manner as in Example 7 above, except that black azo pigments (2) to (7) represented by formulas (a2) to (a7) were used instead of black azo pigment (1), and pigment dispersants of the types shown in Table 2 were used. The obtained black pigment dispersions were subjected to the above evaluations ((1) fluidity (storage stability), (2) gloss of the color-developing surface, and (3) foreign matter in the coating film). The results are shown in Table 2.

[0092] TIFF0007607526000021.tif255169

[0093] <Formation and evaluation of CF's BM pattern> (Example 49) (1) Preparation of photosensitive black resist ink 40 parts of the black pigment dispersion obtained in Example 7, 5 parts of 60% propylene glycol-1-monomethyl ether-2-acetate solution of acrylated acrylic polyol photosensitive resin, 2 parts of trimethylolpropane triacrylate, 3 parts of dipentaerythritol hexaacrylate, 1 part of photopolymerization initiator (ethanone-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), trade name "Irgacure OXE02", manufactured by BASF), and 51 parts of propylene glycol-1-monomethyl ether-2-acetate were mixed. After thoroughly stirring to become uniform using a high-speed stirrer, the mixture was filtered through a filter with a pore size of 3 μm to prepare a photosensitive black resist ink.

[0094] (2) Evaluation of black coating film (resist film) A photosensitive black resist ink was applied onto a glass substrate using a spin coater. After preliminary drying at 60°C, the substrate was prebaked. An ultra-high pressure mercury lamp was used to apply 400 mJ / cm 2 After exposure to a light amount of 1000 nm, the black coating film was post-baked at 230°C for 30 minutes to form a black coating film having a thickness of 2 µm. The transmittance of the black coating film formed was 20% or less for light from the long wavelength side of the visible light region to around 670 nm, and the transmittance of light at 780 nm reached 82%, after which it gradually increased and reached an equilibrium state. In particular, the transmittance of light in the range of 580 to 625 nm was extremely low, being 5% or less. The volume resistivity of the black coating film formed was 10 14 The resistance was found to be over Ω·cm, indicating that the coating is highly insulating.

[0095] (3) BM pattern formation A photosensitive black resist ink was applied onto a glass substrate using a spin coater, and then prebaked at 80°C for 10 minutes to form a black coating film with a thickness of 2 μm. A super-high pressure mercury lamp was used to apply 100 mJ / cm2 of light through a negative photomask pattern of the BM pattern. 2The film was exposed to a light intensity of 10 ...

[0096] (4) Preparation of red, green, blue, yellow, and purple pigment dispersions Pigment dispersions of each color were prepared in the same manner as in Example 7 described above, except that PR254 (diketopyrrolopyrrole red pigment), PR177 (anthraquinone red pigment), PG36 (copper phthalocyanine green pigment), PB15:6 (ε-type copper phthalocyanine blue pigment), PY185 (yellow pigment), and PV23 (dioxazine violet pigment) were used instead of Chromofine Black A1103, and a known pigment derivative having a sulfone group was also used.

[0097] (5) Preparation of photosensitive resist inks of each color A pigment dispersion using PR254 and a pigment dispersion using PR177 were mixed in a ratio of 8:2 to obtain a blend. A photosensitive red resist ink was prepared in the same manner as the photosensitive black resist ink described above, except that the resulting blend was used instead of the black pigment dispersion.

[0098] A pigment dispersion using PG36 and a pigment dispersion using PY185 were mixed in a ratio of 6:4 to obtain a blend. A photosensitive green resist ink was prepared in the same manner as the photosensitive black resist ink described above, except that the blend obtained was used instead of the black pigment dispersion.

[0099] Furthermore, a pigment dispersion using PB15:6 and a pigment dispersion using PV23 were mixed in a ratio of 8:2 to obtain a blend. A photosensitive blue resist ink was prepared in the same manner as the photosensitive black resist ink described above, except that the blend obtained was used instead of the black pigment dispersion.

[0100] (6) Formation of RGB pixels on CF The glass substrate on which the BM was formed was set on a spin coater. The prepared photosensitive red resist ink was spin-coated onto the glass substrate, and then pre-baked at 80°C for 10 minutes. Using a proximity exposure machine equipped with an ultra-high pressure mercury lamp, 100 mJ / cm was applied through a photomask with a mosaic pattern. 2 The substrate was exposed to light at a light intensity of 10 ...

[0101] <Preparation and evaluation of gravure printing ink> (Example 50) 10.5 parts of the fine powder of the black pigment obtained in Example 7, 0.5 parts of the pigment dispersant (A) obtained in Example 1, and 30 parts of a 40% methyl ethyl ketone: toluene (1:3) mixed solvent solution of a polyurethane resin in which an isocyanate-terminated polyester is chain-extended with a diamine were mixed. 2 parts of a cationic polymer dispersant, 2.5 parts of a 40% toluene solution of a polycarbodiimide compound obtained using tolylene diisocyanate, and 54.5 parts of a methyl ethyl ketone: toluene: isopropyl alcohol (50: 30: 20) mixed solvent were added, and then thoroughly mixed using a high-speed stirrer. A black gravure printing ink was prepared by dispersing the pigment using a horizontal continuous media disperser using glass beads as a dispersion medium. A gravure printing machine was used to apply the prepared gravure printing ink to a polyamide film, a polyester film, and a polypropylene film for printing, and a black film was obtained. All of the obtained black films were capable of blocking visible light and sufficiently transmitting near-infrared light.

[0102] <Production and evaluation of polycarbonate resin molded plates> (Example 51) 20 parts of the fine powder of the black pigment obtained in Example 7, 1 part of the pigment dispersant (A) obtained in Example 1, and 80 parts of the polycarbonate resin powder were thoroughly mixed using a Henschel mixer. Then, the mixture was mixed and kneaded using a twin-screw extruder to obtain a master batch containing 20% ​​of the black pigment. 2 parts of the obtained master batch and 100 parts of polycarbonate resin pellets were mixed using a Henschel mixer, and then kneaded using a twin-screw extruder to obtain black resin pellets. The obtained resin pellets were molded using an in-line screw injection molding machine to obtain a black polycarbonate resin molded plate (black plate) with excellent pigment dispersion. The obtained black plate shielded visible light and sufficiently transmitted near-infrared light, and was usable for applications such as infrared transmission filters.

[0103] <Production and evaluation of acrylic resin molded plates> (Example 52) 20 parts of the fine powder of the black pigment obtained in Example 7, 1 part of the pigment dispersant (A) obtained in Example 1, and 80 parts of acrylic resin (polymethyl methacrylate) powder were thoroughly mixed using a Henschel mixer. Then, the mixture was mixed and kneaded using a twin-screw extrusion kneader to obtain a master batch containing 20% ​​of the black pigment. 2 parts of the obtained master batch and 100 parts of acrylic resin pellets were mixed using a Henschel mixer, and then kneaded using an extruder to obtain black resin pellets. The obtained resin pellets were molded using an in-line screw injection molding machine to obtain a black acrylic resin molded plate (black plate) with excellent pigment dispersion. The obtained black plate shielded visible light and sufficiently transmitted near-infrared light, and was usable for applications such as infrared transmission filters.

[0104] <Preparation and Evaluation of Polyurethane Coating Agent> (Example 53) (1) Preparation of polyurethane coating agent (liquid) 40 parts of the fine powder of the black pigment obtained in Example 7, 2 parts of the pigment dispersant (A) obtained in Example 1, and 60 parts of an adipate ester plasticizer were thoroughly kneaded using a three-roll kneader to obtain a plasticizer dispersion paste of the black pigment (black pigment toner). 60 parts of the titanium oxide white pigment and 40 parts of an adipate ester plasticizer were thoroughly kneaded using a three-roll kneader to obtain a plasticizer dispersion paste of the white pigment (white pigment toner). On the other hand, 100 parts of a methyl ethyl ketone dispersion (solid content: 30%) of a polyether polyol diphenylmethane diisocyanate polyurethane having a carboxy group, 5 parts of a methyl ethyl ketone solution (solid content: 50%) of a polyether polyol diphenylmethane diisocyanate polyurethane, and 2.5 parts of a polycarbodiimide crosslinking agent (solid content: 20%) were thoroughly mixed to obtain a mixture. 1 part of black pigment toner and 6 parts of white pigment toner were added to the obtained mixture, and then thoroughly mixed to prepare a gray polyurethane coating liquid.

[0105] A white polyurethane coating liquid was prepared in the same manner as above, except that the black pigment toner was not used and only the white pigment toner was used. A black polyurethane coating liquid was prepared in the same manner as above, except that the white pigment toner was not used and only the black pigment toner was used.

[0106] (2) Evaluation A gray polyurethane coating solution was applied to the surface of nylon woven tent fabric at a rate of approximately 200 g / m2. 2 After coating so that the coating liquid was 100% by weight, the fabric was dried to produce a gray processed woven fabric. The processed woven fabric produced reflects the heat rays of direct sunlight and can be used for applications such as tents to prevent temperature rise. The prepared white polyurethane coating liquid was applied as a base coat, and then the prepared black polyurethane coating liquid was applied as a top coat to produce polyurethane synthetic leather with a two-layer structure. The obtained synthetic leather reflects heat rays and can be used for applications such as automobile interiors.

[0107] <Production and evaluation of solution-dyed fibers> (Example 54) 50 parts of the fine powder of the black pigment obtained in Example 7, 2.5 parts of the pigment dispersant (A) obtained in Example 1, and 50 parts of a lubricant (ethylene bisstearic acid amide powder) were mixed using a Henschel mixer to obtain a powder colorant (dry color) with a pigment content of 50%. 1 part of the obtained dry color and 99 parts of polypropylene resin pellets were mixed using a Henschel mixer, and then kneaded using a vent-type 40 mm extruder to obtain resin pellets containing 0.5% black pigment and 0.5% black pigment. The obtained resin pellets were spun using a melt spinning machine to obtain a vivid black polypropylene fiber (solution-colored fiber) with a fineness of 10 denier and excellent pigment dispersibility. The woven fabric made from the obtained solution-colored fiber was capable of reflecting the heat rays of direct sunlight, and could be used for applications such as parasols and curtains that avoid temperature rise.

[0108] <Production and evaluation of resin molded products> (Example 55) 5 parts of the fine powder of the black pigment obtained in Example 7, 0.1 parts of the pigment dispersant (A) obtained in Example 1, 20 parts of the titanium oxide white pigment, and 75 parts of the polyethylene resin powder were mixed using a Henschel mixer to obtain a dry color. 1 part of the obtained dry color and 100 parts of polybutylene terephthalate (PBT) resin pellets were mixed using a Henschel mixer, and then kneaded using an extruder to obtain black resin pellets. The obtained resin pellets were molded using an in-line screw injection molding machine to obtain a black resin molded plate with excellent pigment dispersion. The obtained resin molded plate was capable of reflecting the heat rays of direct sunlight, and could be used as a resin molded product that avoids temperature rise.

[0109] <Production and evaluation of textile printing paste> (Example 56) 71 parts of press cake containing 25 parts of finely divided powder of black pigment obtained in Example 7, 1.5 parts of pigment dispersant (A) obtained in Example 1, 10 parts of nonionic pigment dispersant, 1 part of defoamer, and 18 parts of water were thoroughly premixed. Next, the pigment was dispersed using a horizontal continuous media disperser using glass beads as a dispersion medium to prepare a high-concentration dispersion of black pigment (black color base). 20 parts of the prepared black color base, 25 parts of reactive acrylic acid alkyl ester latex (solid content 40%), 0.5 parts of defoamer, 1 part of dispersant, 3 parts of dispersion stabilizer for oil-in-water emulsion, 38 parts of mineral turpentine, and 12.5 parts of water were emulsified and dispersed using a homogenizer (powerful emulsifying disperser) to obtain an oil-in-water black emulsion paste. 2 parts of carbodiimide-based crosslinking agent (solid content 40%) was added to the obtained black emulsion paste and thoroughly mixed to obtain a black printing paste. The black printing paste was printed over the entire surface of a polyester-cotton blend fabric, which was then cured at 120°C for 15 minutes to obtain a plain black printed fabric. The plain black printed fabric was capable of reflecting heat rays.

Claims

1. A pigment dispersant which is a compound represented by the following general formula (1), a quaternary ammonium salt thereof, an amine salt thereof, or a metal salt thereof: (In the general formula (1), X is each independently represented by any one of the following general formulas (1-a) to (1-c).) (In the general formulae (1-a) to (1-c), * indicates the bonding position with the nitrogen atom. In the general formula (1-a), R 1 indicates an aromatic group which may have a substituent. In the general formula (1-b), R 2 indicates an aromatic group which may have a substituent. In the general formula (1-c), R 3 and R 4 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a nitro group, or a sulfonamide group, m and n each independently represent a number from 0 to 5, and m+n is 5 or less.)

2. A pigment composition comprising a pigment and the pigment dispersant according to claim 1.

3. 3. The pigment composition according to claim 2, wherein the content of the pigment dispersant is 0.5 to 40 parts by mass based on 100 parts by mass of the pigment.

4. A pigment colorant comprising the pigment composition according to claim 2 or 3 and a film-forming material.

5. 5. The pigment colorant according to claim 4, which is used for image display, image recording, gravure printing ink, writing ink, plastics, pigment textile printing, paint, or the black matrix of a color filter.

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