TW200815537A - Light-absorbing pigment composition - Google Patents

Abstract

The purpose of the present invention is to provide a light-absorbing pigment composition which can confer the light-absorbing function on the members such as the plasma display panel, etc. at a specific wavelength, and can sufficiently inhibit the deterioration of the function with time. The light-absorbing pigment composition contains optically-stabilized cyanin pigment and adhesive agent, and the optically-stabilized cyanin pigment is formed by associating a pair of phenyl-substituted dithiol metal complex anion and cyanin pigment cation, for example.

Description

200815537 IX. INSTRUCTIONS: [BRIGHT HEAD] Technical Field The present invention relates to a light absorbing pigment composition having adhesive and near infrared absorbing function 5 . L Prior Art 3 Background Art In recent years, light absorbing materials containing light absorbing components have been used in various collars.

Used in the domain. For example, it can be widely used as a light absorbing material that can mainly absorb the near-infrared region 10, a near-infrared ray blocking film for a plasma display panel, a filter for a semiconductor 15 20 light-receiving element, and a power-blocking heat ray-blocking An infrared absorbing film or a near-infrared absorbing plate, an agricultural near-infrared absorbing film for the purpose of selective use of sunlight, a photosensitive lithographic printing plate using laser light or the like, and a recording medium using heat absorption by near-infrared rays. In addition, it mainly absorbs the visible light in the visible light region to improve the color purity, and is widely used as an electric display panel, a liquid crystal display, an electroluminescence display n, a cathode tube display tube, and an electric field emission. A filter for an image display device such as a display or the like. The specific light absorbing material is a light absorbing coloring matter which has a sleek light with respect to light of a specific wavelength. The light absorbing material can be produced, for example, by dissolving the light-receiving dye in a solvent as a pigment solution or a transparent substrate such as a fat. In the near-infrared ray barrier film for glass or tree display panel, the second embodiment has an excellent light absorption characteristic in the wavelength region of the front iron display (10). Further, the image display device is used with a filter system. A light absorbing dye having excellent light absorption characteristics at a wavelength of around 490 nm or around 550 nm, which is coated on a polyethylene terephthalate (PET) film or the like, and dried to produce a film-like light absorption. material. The light absorbing material thus obtained can be used by being bonded to a predetermined member or the like together with various films having other functions, using an adhesive as needed.

Therefore, in order to reduce the thickness of the light absorbing material and to simplify the manufacturing steps thereof, an infrared absorbing adhesive containing an adhesive resin and an infrared absorbing agent having a maximum absorption wavelength at 700 to 11 nm has been proposed. Object 10 (refer to Patent Document 1). However, since the light absorption energy is excellent and the price is low, and it is used as a cyanin dye for a light absorbing pigment of a light absorbing material, the light absorption energy deteriorates with time when used in combination with an adhesive. It will become severe, and there is still room for improvement due to lack of practicality. [Patent Document] JP-A-2001-207142 [Brief Description of the Invention] The present invention has been made in view of the foregoing problems, and its object is to provide an easy and efficient solution. A light absorbing pigment composition shown by a light absorbing dye having a specific wavelength of a member such as a plasma display panel and having a predetermined wavelength is sufficiently suppressed. Means for Solving the Problems The present invention can provide a light absorbing pigment composition containing a light-stabilized cyanine dye and an adhesive, as in 6, 200815537, item 1. Item 2. The light absorbing pigment composition according to Item 1, wherein the light-stabilized cyanine-based pigment is a ionic complex of a substituted benzenedithiol metal complex anion and a cyanine-based cation. Item 3. The light absorbing pigment composition according to Item 2, wherein the anionic anion of the substituted thiol thiol metal complex is represented by the formula (1):

\/SYY s°!, R2 (l) i〇 (wherein R1 and R2 are each independently, and represent an alkyl group having a carbon number of i to 6 and an acryl group having a carbon number of 1 to 8, which may have a substituent. a phenanthrenyl group, a piperidinyl group which may have a substituent, a pyrrolidinyl group which may have a substituent, a thiomorpholine group which may have a substituent, a piperylene group which may have a substituent or a benzene which may have a substituent

The group, and Μ represents a transition metal atom) represents a substituted benzenedithiol metal mismatched anion. The light absorbing pigment composition according to any one of items 1 to 3, wherein the above-mentioned adhesive is a (meth) acrylate copolymer. Hereinafter, the present invention will be described in detail. In the present invention, the photo-stabilized cyanine-based pigment system is proposed to compensate for the disadvantages of the cyanine-based color, and the disadvantage is that the light-absorptive property of light which is mostly used as light absorption = is highly deteriorated, and It refers to a relative ionic combination of a metal benzene dithiolate anion and a cyanine dye cation, or a mixture of a gold complex and a cyanine pigment. In the relative ionic combination of the benzenedithiol metal complex anion and the cyanine dye cation, a relative ionic combination of the unsubstituted benzenedithiol metal complex anion and the cyanine dye cation, and the substituted benzene An example of a relative ionic combination of a dithiol 5 metal complex anion and a cyanine dye cation is exemplified. For example, a counter ion assembly of the following formulas (2) and (3) of JP-A-2000-121807 can be used as the counter ion-bonding compound of the anthracene benzenedithiol metal complex anion and the cyanine dye cation. 10 【化2】

8 15 200815537 【化3】

The counter ion assembly of the substituted benzenedithiol metal complex anion and the cyanine dye cation, for example, the relative ion complex of the following formula (4) of JP-A-6-338059, and the following The ionic conjugate of the substituted benzenedithiol metal complex anion and the cyanine dye cation represented by the formula (1). 10【化4】

9 (1) 200815537 【化5】

In the formula (1), R1 and R2 are each independently, and represent a leukox group having a hindrance of 1 to 6, an alkylamino group having 1 to 8 carbon atoms, a morphine group which may have a substituent, and a substituent having a substituent. A piperidinyl group, a pyrrolidinyl group which may have a substituent, a thiofenoflavinyl group which may have a substituent, a σ-endyl group which may have a substituent or a phenyl group which may have a substituent, and Μ represents a transition metal atom. In the photo-stabilized cyanine pigment, the metal complex in the mixture of the metal complex and the cyanine dye is not particularly limited, and examples thereof include dithiocyclopentane such as JP-A-2001-234000. a dithi〇lane metal complex and a benzenedithiol metal complex corresponding to the aforementioned benzenedithiol metal complex anion. In these photo-stabilized cyanine dyes, a relative ionic combination of a stupid dithiol metal complex anion and a cyanine dye cation is suitable. In the specific ion-combined body, it is more suitable to replace the relative ionic complex of the abundance-thiol metal complex anion fish flower pigment cation by the solubility or durability of the solvent, and A counter ion assembly of a substituted benzenedithiol metal complex anion represented by the formula 20 (1) and a cyanine dye cation is particularly suitable. In the present invention, the light-stabilized cyanine dyes may be used singly or in combination of two or more. 10 200815537 Hereinafter, the relative ionic combination of the substituted benzenedithiol metal complex anion represented by the general formula (1) and the cyanine dye cation which can be used in the light absorbing pigment composition of the present invention will be described in detail as a special A suitable light stabilizes the cyanine pigment. 5 In the general formula (1), R and R are each independent and represent a carbon number of 1 to 6

a group, an alkylamino group having 1 to 8 carbon atoms, a morpholinyl group which may have a substituent, a piperidinyl group which may have a substituent, a pyrrolidinyl group which may have a substituent, and a thiofenofolin which may have a substituent A phenyl group which may have a substituent or a phenyl group which may have a substituent, and Μ represents a transition metal atom. 10 C. The alkyl group having 1 to 6 carbon atoms may, for example, be methyl, ethyl, isopropyl, η-propyl, η-butyl, sec-butyl, tert-butyl, η·pentyl or iseth. Base, neopentyl, η-hexyl and isohexyl.

Examples of the alkylamine group having an inverse number of 1 to 8 such as N,N-tert·butylamino and the like include an N-f-amino group, an ethylamino group, an N-isopropylamino group, a Ν-η·propylamino group, and a Νηηττ-amino group. N,N-dimethylamino, 15 N,N-methylethylamino, N,N•diethylamino, N,N•ethylisopropylamino, Ν'% ethylisohexylamine, N, N-ethyl-n-hexylamino, N,N-methylisoamylamino, N,N-methyl-η-pentylamino, N,N-diisopropylamino, _-di-propylamino , N,N-di-n-butylamino, N,N-diisobutylamino, n,n-di-butanylamino and 20 may have a substituent, such as: 福福Linke, ^methylmorpholine, 3-methylnorporinyl, 'methylmorpholinyl, 2 ethyl ethionine, 4_n propyl phenothinyl, 3·η· Butyl wheylinyl, 2,4_dimethylene forest base 2'6·-methylfofolinyl and 4·benf starting group. The bottom biting group which may have a substituent may, for example, be a face group, a 2-methyl brace 11 200815537 5 σ-based group, or a 3-mercapto group. Base, 4_ 曱 12 base bite,. -ethyl octadecyl, 4-n-propylpiperidinyl, 3-n-butylpiperidinyl, 2,4-dimethylpiperidinyl, 2,6-dimercaptopiperidinyl and 4 - amphetidine group and the like. The pyrrolidinyl group which may have a substituent may, for example, be a pyrrolidinyl group, a 2-methyl σ piroxime group, a 3-methyl hydrazine group, a 4-fluorenyl group, a fluorenyl group, a 2-ethyl group.咐* V σ ϋ 基 , 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 4 And 4-phenylpyrrolidinyl and the like. The thiomorpholine group which may have a substituent may, for example, be a thiomorphine base, a 2-methylthiomorpholinyl group, a 3-methylthiomorpholinyl group, or a 4-methylsulfide group. 10 generations of wheylinyl, 2-ethylthiofenofyl, 4-η-propylthiofenofyl, 3-η-butylthiomorpholinyl, 2,4-dimethyl A thiomorpholine group, a 2,6-dimethylthiomorpholinyl group, a 4-phenylthiomorpholinyl group or the like. The piperage group which may have a substituent may, for example, be a piperidinyl group, a 2-methylpipephinyl group, a 3-methylpiperidyl group, a 4-mercaptopiperidyl group, a 2-ethylpiperidinyl group, or a 4- Η-15 propylpiperidinyl, 3-η-butylpiperidinyl, 2,4-dimethylpiperidinyl, 2,6-di-methylmethyl-thyl, 4-benzoquinone 2-mouth bite base σ bottom n well base and so on. The phenyl group which may have a substituent may, for example, be a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 2,6-dimethylphenyl group or a 4-ethylbenzene group. Base, 2-η-propylphenyl, 4-η-butylphenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4_-20 dichlorophenyl, 2-bromophenyl, 4 -bromophenyl, 2-ox-4-bromophenyl, 4-aminophenyl, 2,4-diaminephenyl, 2,4-dinitrophenyl, 2-ethylphenyl, 4 - Ethylphenyl, 2-hydroxyphenyl, 4-hydroxyphenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2-mercaptothiophenyl and 4-methylthiobenzene Base. In the case of the above-mentioned R1 and R2, it is preferable that R1 and R2 are each excellent from the viewpoint that the relative ionic combination of the substituted benzenedithiol metal mismatch 12 200815537 anion is excellent in solubility in an organic solvent. Independent, and is N,N-diethylamino, morpholinyl, pyrrolidinyl, piperidinyl, piperidinyl or phenyl. Specific examples of the transition metal atom represented by Μ in the formula (1) include, for example, a 5-atom atom, a copper atom, and an initial atom. The substituted benzenedithiol metal complex anion represented by the formula (1) is derived from a substituted benzenedithiol metal complex. The substituted benzenedithiol metal complex can be synthesized by the same method as disclosed in JP-A-H09-309886 or JP-A-10-45767. Namely, first, a hydrosulfide such as hlogenobenzene and sodium hydrosulfide is reacted in a polar organic solvent in the presence of sulfur and iron powder to form an iron complex of substituted phenyldithiol. The resulting iron complex of the substituted phenyldithiol is then reacted with a halide of a transition metal, followed by reaction with an ammonium salt or a scale salt to prepare a substituted metal benzenedithiolate complex. 15 The substituted cyanodithiol metal complex anion represented by the formula (1) and the cyanine dye cation which can constitute a relative ionic bond of the preferred light-stabilized cyanine dye are not particularly limited, for example, A commercially available cyanine dye can be used, and it is derived by producing the relative ion complex described later. The specific examples of the commercially available pigments of the sputum are, for example, FEW Chemical Co., Ltd., S13, S889, S941, S946, and S824, and SIBER. ST78" and so on. The cyanine dye cations which are emitted from these cyanine dyes may be used singly or in combination of two or more. 13 200815537 To obtain a relative ionic complex of the above-mentioned substituted benzenedithiol metal complex, which is, for example, the above-mentioned substituted benzenedithiol metal complex and the aforementioned cyanine pigment in an organic solvent. In the middle of the anti-deer benzene, after removing the metal oxide complex from the above-mentioned substituted benzenedithiolate: the anion and the anion plasma from the above-mentioned cyanine pigment, the dried solution can be dried, and the crystal can be dried.

The use ratio of the cyanine pigment is preferably 0.8 to 1.2 mol with respect to 1 mol of the substituted stupid-sulfur metal complex, and is further reduced by the 〇·9~丨丨莫耳--the cyanine pigment When the use ratio is less than 0β8 mole, there will be a 10% decrease in yield. Further, if the use ratio of the cyanine dye is more than 1.2 m, it is not economical to produce an effect corresponding to the amount used. The organic solvent used in the above reaction may, for example, be ν, dimethyl decylamine, acetonitrile, tetrahydrofuran, acetone or methyl ethyl ketone. Among them, hydrazine, hydrazine dimethyl dimethyl carbamide and acetonitrile are suitable. The organic solvent is preferably used in an amount of from 1,000 to 100,000 parts by weight, based on 100 parts by weight of the substituted metal phenate, and more preferably from 4,000 to 20,000 parts by weight. If the amount of the solvent used is less than 1 part by weight, there is a possibility that the mixture cannot be uniformly mixed. Further, if the amount of the organic solvent used is more than 100,000 parts by weight, the volumetric efficiency will be poor and uneconomical. 20 From the viewpoint of suppressing decomposition of the cyanine dye, the reaction temperature is preferably 〇60 ° C, and more preferably 10 to 50 ° C. The reaction time varies with the reaction temperature, but the reaction usually ends instantaneously. In the sodium reaction, the substituted benzenedithiol metal complex and the cyanine dye are soluble in the organic solvent, and the resulting relative ionic complex precipitates at the same time as the reaction 14 200815537, and the reaction liquid is slurried. . The method for removing the cation derived from the metal sulfonate of the substituted benzenedithiolate and the anion derived from the cyanine dye from the obtained reaction liquid is not particularly limited. For example, the metal complex compound derived from the substituted benzenedithiolate can be dissolved. The cation 5 ion and the anion plasma derived from the cyanine dye are added to the reaction liquid without dissolving the solvent of the target relative ion conjugate, and are cooled, and the relative ion conjugate is precipitated and then filtered. Further, from the viewpoint of sufficiently removing the plasma, it is preferred to recrystallize the obtained relative ion-bound body. Such a medium can be exemplified by water, methanol, ethanol, propanol, and the like. Among them, water and methanol are suitable from the viewpoint of efficiently removing unnecessary ions. The amount of the solvent used is preferably from 1 〇〇〇 to 1 〇〇〇〇〇 by weight based on 100 parts by weight of the substituted benzenedithiolate metal complex, and is 5 〇〇〇 2 〇〇〇〇. The weight is better. Further, when a mixture of a substituted benzenedithiol metal complex and a cyanine dye is used as the light-stabilized cyanine dye, the mixture is produced by, for example, a substituted metal thiodithiolate relative to 1 mol. The complex compound is added with 0.8 to 1.2 mol of the cyanine dye, and then mixed by a usual method. 2〇 The light absorbing pigment composition of the present invention contains the light-stabilized cyanine dye and the adhesive thus obtained. The adhesive for the light absorbing pigment composition of the present invention is not particularly limited, and examples thereof include a (meth)acrylic acid g copolymer, a polychloroethylene, a ring resin, and an oxetane resin. , polyurethane, vinyl acetate: 15 200815537 Polymer, styrene-propylene copolymer, polyester, polyamide, polyolefin, stupid ethylene-butadiene copolymer rubber, butyl rubber and silicone resin, etc. . Among them, from the viewpoint of excellent transparency and durability, it is suitable for (meth) acrylate copolymer, cycloolefin resin, oxycyclobutane resin and polyester vinegar, and (meth) propyl hydrazine ^ 5 Ester copolymers are more suitable. In addition, when glass is used as the substrate for coating the light-absorbing pigment composition, the alkali or the like eluted from the glass diffuses, and the light-stabilized cyanine dye contained in the light-absorbing pigment composition is deteriorated. However, by using a (meth) acrylate copolymer, an epoxy resin, a gas ring butyl resin, and a polyester as an adhesive, deterioration thereof can be prevented or reduced. The (meth) acrylate copolymer may, for example, be a monovalent (meth)-alkyl acrylate, a monomeric substance having a hydroxyl group in the molecule, and a molecule having a carboxyl group or a guanamine group. a copolymer of at least one of a single amount of any functional group of an amine group. Examples of the alkyl (meth)acrylate include methyl (meth)acrylate, ethyl (methyl 15-ethyl)acrylate, propyl (meth)acrylate, and η-butyl (meth)acrylate, (methyl). ) iso-butyl acrylate, t-butyl (meth)acrylate, 2·ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, iS0-octyl (meth)acrylate, ( Dodecyl (meth)acrylate, octadecyl (decyl)acrylate, and the like. Examples of the monovalent body having a hydroxyl group in the molecule include (meth)acrylic acid 20 20-hydroxyethyl ester, (meth)acrylic acid 4-hydroxybutyl ester, and (meth)acrylic acid 2-hydroxyl group. ^ propyl ester, 2-hydroxybutyl (meth) acrylate, 6-hydroxyhexyl (meth) acrylate, 1,4-cyclohexane dimethanol monoester of (methyl) propionate, propionate Gas-2-hydroxypropyl ester, diethylene glycol mono(meth)acrylate, allyl alcohol, and the like. An example of a singly having a hydroxyl group in a molecule and a singly having a carboxyl group in the molecule, and any functional group of the amine group or the amine group: (meth)acrylic acid, (A) 2-carboxyethyl acrylate, 3-carboxypropyl (meth)acrylate, 4-carboxybutyl (meth) acrylate, ita-conic acid, crotonic acid, Maleic acid, fumaric acid, maleic anhydride, etc., carboxyl group-containing monocomponent; (mercapto) acrylamide, n, n-dimethyl (methyl ) acrylamide, N-isopropyl (decyl) acrylamide, hydrazine, hydrazine diethyl (meth) acrylamide, acryl hydrazinoline, hydrazine-ethylene acetamide, diacetone ( Methyl) acrylamide, hydrazine, hydrazine-dimethylaminopropyl (meth) acrylamide, ethylene 4b^^ (vinyl pyrrolidone), methyl (meth) acrylamide, 10 methoxy Ethyl (fluorenyl) acrylamide, etc., a single amount of amidino group; (mercapto) N,N-dimethylamine ethyl acrylate, hydrazine, hydrazine, diethylamine ethyl (methyl Acetylene amidoxime, hydrazine-dimethylaminopropyl ( Yl) acrylamide, (meth) acrylic acid ethyl ester and the like do Four morpholine, Single-containing group of the like. Further, in addition to the aforementioned monolithic body for producing the (meth)propionate copolymer, other monoliths may be further added. Examples of other singly-sized monomers include (meth) methoxyethyl (meth) acrylate and ethoxy acrylate (meth) acrylate (alkoxyalkyl (meth) acrylate). (meth)acrylic acid glycidyl ester, etc., epoxy group-containing (meth) acrylate; (meth) acrylate acetoxyethyl ester, etc., containing ethyl acetonitrile (methyl) Acrylate; 20 aromatic monomers such as styrene, methyl styrene and vinyl benzene; methacryloxypropylmethoxysilane, vinyl acetate, vinyl chloride and ) Acrylonitrile and the like. The adhesive used for the light absorbing pigment composition of the present invention may be used singly or in combination of two or more. 17 200815537 It is usually necessary to have a sticky adhesion to the pigmented silk, so it is to be transferred by glass.) 2: J is 仏' and is °. The following are preferred, especially in the present invention, and the above-mentioned adhesive can be used in the general market. For example, the product name "SZ6232" and "SZ6233", which are manufactured by the Carbide Industry Co., Ltd., are exemplified by the __ silk material.

10 "SZ6234", "SZ647 i", "SZ6472" and the product name "Similar 147" manufactured by Sakamoto Chemical Industry Co., Ltd. In addition, the name of the product "nichig〇 POLYESTER XI_0002" manufactured by Nippon Synthetic Chemical Industry Co., Ltd. is used as an example, and the epoxy resin may be a product name "EPIK0TE 828" manufactured by Nippon Epoxy Co., Ltd. "Ερικ〇ΤΕ

80IN", EPIKOTE 1001", "EPIKOTE 834X90", "KPIKOTE

806", "EPIKOTE 4004P", "EPIKOTE 1256", "EPIKOTE 15 152", "EPIKOTE 103 IS", "EPIKOTE 872", "EPIKOTE

19IP", "EPIKOTE ST 11", "EPIKOTE DC11", "EPIKOTE RC11", "EPIKOTE QX12", "EPIKOTE SL11", "EPIKOTE EM I 24", "EPIKOTE IBMI12", "EPIKOTE YH300", "EPIKOTE DICY7" ; NAGASE chemteX AG 20 products "DENACOL EX-212L", "DENACOL EX-214L", "DENACOL EX-216 L", "DENACOL EX-321 L", "DENACOL EX-850L"; Japan Oil and Fats The company's trade names "epiolg_ioo", "epiole-ioo", "epiole-4〇o", "epiol E-1000", "EPIOLP-200"; and DAICEL Chemical Industry Co., Ltd. 18 200815537 under the trade name "CELLOXIDE2021P" For example, the oxycyclobutane resin may be exemplified by the trade name "ARON OXETANE OXT_221" manufactured by Toagos Corporation. Although the light absorbing pigment composition of the present invention contains an adhesive, it is not sufficiently clear that the light absorbing energy can be sufficiently deteriorated with time, and it is generally considered that the thiol group or the —COOH group present in the adhesive may be used. The light absorption energy of the cyanine dye is reduced, and the effect is alleviated by using a light-stabilized cyanine dye. In addition to the light-stabilized cyanine-based color 10 and the adhesive, the light-absorbing pigment composition of the present invention can further contain various pigments and hardenings such as cyanine-based pigments, without impairing the effects of the present invention. Agent, hardening catalyst, bridging agent, color correction pigment, leveling agent, antistatic agent, heat stabilizer, antioxidant, dispersant, flame retardant, slip agent, plastic gas, or ultraviolet absorber Hard to add additives. I5 In the light absorbing pigment composition of the present invention, the amount of the photostabilized cyanine dye is preferably from 1 to 5 parts by weight based on 1 part by weight of the adhesive, and is 0.01% by weight. 20 parts by weight is preferred, especially in parts. If the amount of light-stable cyanine pigment is less than 0 001, there will be insufficient light absorption. Further, if the amount of the light-stabilized cyanine dye is more than 50 parts by weight, there is no effect corresponding to the amount used, and it is not economical. The method for producing the light-absorbing pigment composition of the present invention is not particularly limited, and for example, a method of adding the above-mentioned light-stabilized cyanine dye, an adhesive, and the above-mentioned additive, and mixing them by a usual method can be mentioned. Further, by adding an appropriate amount of a solvent such as a ketone such as acetone, methyl ethyl ketone, methyl isobutyl condensate, cyclohexane or cyclohexanone to another polymer, the light-absorbing pigment composition is liquid. It is easy to mix. The light absorbing pigment composition of the present invention can be directly applied to a buccal surface such as a panel for electric display, or can be applied to a film having an other function such as an antireflection film or the like, and used as a light absorbing material. In the case of the former, a substrate such as a film for forming a light absorbing material is not required, and a step of applying a light absorbing dye to the substrate or the like is not required, or an adhesive is applied to the coated surface of the light absorbing pigment after application. Coating step. Further, in the case of the latter 10, the subsequent steps are required for the past, but it is no longer necessary to apply the adhesive to the coated surface of the light absorbing color. The coating method of the light-absorbing pigment composition of the present invention may, for example, be a bar coating method, a spin coating method, a gravure printing method, a deep coating method (deep (3)), a roll coating method, or the like. Further, in the coating step, in order to make it easier to carry out the coating operation, it is preferable to use the above-mentioned solvent to form a liquid in the composition, which is described in the method for producing a light-absorbing pigment composition. Further, in the light absorbing pigment composition of the present invention, when the above-mentioned additive such as a curing agent is used, it is preferable to use a curing step or a post-processing step for making the additive effect of the additive more attractive. In the case, for example, a step of performing a predetermined period of time in a dark place at a room temperature, a step of performing heating or light irradiation, or the like is prepared. Advantageous Effects of Invention By using the light absorbing pigment composition of the present invention, it is possible to sufficiently impart a light absorption function to a member such as a plasma display panel, which is easily and in a probabilistic manner. BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be specifically described by way of Examples and Comparative Examples, but the present invention 5 is not limited to the Examples. Synthesis Example 1 In 4·(morpholinoxasulfonyl)], 2_2 To chlorobenzene 59 2 g (〇 2 mol), 183 g of N,N' dimethylformamide and 33.6 g (0.42 mol) of a 70% by weight aqueous sodium hydrosulfide solution were added, and the reaction was carried out for 3 hours. In the solution, add 10 iron powder 5·9 § (〇·11 mol) and sulphur end 6.7 g (0.21 mol) at 9〇~95. The underarm reaction is 6 hours. In the obtained reaction solution Add methanol to a thickness of 1〇8〇g at room temperature, add 77% by weight of a 28% by weight sodium methoxide solution (sodium methoxide to 〇·2ιmol), stir for 1 hour, add copper chloride (11) 2 hydrate 17 0g (01 Mohr), and then reacted in the chamber for 3 hours. Then, 32.2 g of tetrabutylammonium bromide ((U Mo) was added to the reaction solution, and it was injected at room temperature. The gas is reacted for 2 hours. The liquid thus obtained is concentrated and purified by Shixi rubber column chromatography to obtain a green substituted benzenedithiol metal complex of % hexamethylene. Please refer to the following first Table 2) Synthesis Example 2 2 In the synthesis example 1, except for (4) .8 g of chlorinated hydrate (〇1 mol) instead of n.〇g of copper chloride („) 2 hydrate _ ear), A total of 30.8 g of a substituted benzenedithiol metal complex was prepared as described in Table 1 above. Synthesis Example 3 21 200815537 In Synthesis Example 2 'except 58.8 g of 4_(piperidinylsulfonylphenyl 1,2-dichlorobenzene (0.2 Mozun) instead of 59·2§ Μ 福 福 啉 sulfonate The same procedure as in Synthesis Example 2 except for the fluorenyl-1,2-dichlorobenzene (0.2 mol) was carried out to obtain 28.6 g of a substituted steardithiol metal complex 〇3 (please refer to Table 1 below). ). 5 The structure of the substituted stearic thiol metal complex anion corresponding to each of the obtained substituted monothiol metal complexes is shown in Table 1. [Table 1] The synthesis of the benzenediol metal complex of the first table is the oxime in the formula (1). R1 and R2 in the formula (1) (wherein R1 and R2 are the same) 1 D1 Cu -N 0 v_v 2 D2 Ni Γ~\ -Ν 0 \_y 3 D3 Ni -Ο

10 Synthesis Example 4 _ 28.8 § Substituted benzenedithiol metal complex D (〇.〇l Moer) and 7. ig cyanine pigment E (Please refer to Table 2 below, the product of FEW Chemical Co., Ltd. The name "S0813") (0.01 mol) was dissolved and mixed in 5 〇〇giN, N-dimethylformamide _, and reacted for 3 G minutes under thief. In order to remove 15 * of the desired ions from the reaction solution, methanol _g may be added, and water _g may be added, mixed, cooled and filtered. After this operation was repeated twice, methanol was washed and dried to obtain a ll.ig relative ion-conjugate. 'The tetra-ammonium ion and tetrafluoroborate ion were not detected by ion chromatography. 22 200815537 Synthesis Example 5 In Synthesis Example 4, a relative ion complex was obtained in the same manner as in Synthesis Example 4 except that the substituted benzenedithiolate metal complex D3 was used instead of the substituted benzenedithiol metal complex D2. 11.3g. 5 The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. Synthesis Example 6 In Synthesis Example 4, except that the substituted benzenedithiolate metal complex D1 was used instead of the substituted oxadithiol metal complex D2, the same as in Synthesis Example 4, 10 was obtained to obtain 11.4 g of relative ion binding. body. The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. Synthesis Example 7 In the synthesis example 4, except for the cyanine-based dye E2 (refer to the following Table 2-15, trade name "S0941" manufactured by FEW Chemical Co., Ltd.), the cyanine-based dye E1 was used instead of the synthesis example. The same was carried out, and 11.3 g of a relative ion complex was obtained. The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. 20 Synthesis Example 8 In the synthesis example 5, except for the cyanine-based dye E2 (refer to the second table below, the product name "S0941" manufactured by FEW Chemical Co., Ltd.), the cyanine-based dye E1 was used instead of the synthesis example. The same was carried out, and 11.3 g of a relative ion complex was obtained. 23 200815537 The relative ion complexes obtained by ion chromatography were used to detect tetrabutylammonium ions and tetrafluoroborate ions. Synthesis Example 9 In the synthesis example 6, except for the cyanine-based coloring matter E2 (refer to the following Table 5, the product name "S0941" manufactured by FEW Chemical Co., Ltd.), the other is synthesized. In the same manner as in Example 6, 11.3 g of a relative ion complex was obtained. The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. (Synthesis Example 10) In the synthesis example 4, except for the cyanine-based dye E3 (refer to the second table below, the product name "S0946" manufactured by FEW Chemical Co., Ltd.), instead of the cyanine-based dye E1, the synthesis examples are the same. The same was carried out, and 11.3 g of a relative ion complex was obtained. 15 The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. Synthesis Example 11 In the synthesis example 5, except for the cyanine-based dye E3 (refer to the second table below, the product name "S0946" manufactured by FEW Chemical Co., Ltd.) in place of the cyanine-based dye 20 E1, the synthesis examples are the same. In the same manner, 11.3 g of relative ion binding was obtained by ion chromatography, and the relative ion complexes obtained by ion chromatography were not detected, and tetrabutylammonium ions and tetrafluoroborate ions were not detected. Synthesis Example 12 24 200815537 In the synthesis example 6, except for the cyanine-based dye E3 (refer to the second table below, the product name "S0946" manufactured by FEW Chemical Co., Ltd.) is used instead of the cyanine-based dye E1, In the same manner as in Example 6, 11.3 g of a relative ion complex was obtained. 5 The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. Synthesis Example 13 In the synthesis example 6, except for the cyanine dye E4 (refer to the second table below, the product name "S0824" manufactured by FEW Chemical Co., Ltd.), the cyanine dye 10 E1 was used instead of the synthesis example. 6 is the same, 9.lg relative ion complex is obtained. The obtained relative ion complex was measured by ion chromatography, and tetrabutylammonium ion and tetrafluoroborate ion were not detected. 15 20 25 200815537 [Table 2] Table 2 f

Structural Formula E1 bf4· E2 T bf4- E3 BF4· E4 CI 1 cio4' Example 1 5 32 mg of the relative ion-conjugated body (photo-stabilized cyanine dye) obtained in Synthesis Example 4 After dissolving in 12 g of cyclopentanone, 6 g of an adhesive (trade name "SZ6232" manufactured by Nippon Carbide Industry Co., Ltd.) and 37 mg of a hardener (trade name "CK-102" manufactured by Nippon Carbide Industry Co., Ltd.), And llmg hardening catalyst (trade name "CK-901" manufactured by Nippon Carbide Industry Co., Ltd.), 26 200815537 A light-absorbing pigmented silk which can be recorded after mixing. Then, it was coated on a poly(tetra) film by a spin coater, and dried at 8 Gt for 3 minutes to form a film thickness of 17 and then called a film (4). The surface of the film was made by a roller. The light absorbing material used for evaluation was evaluated for the characteristics of the obtained light absorbing pigment composition. Example 2

In the Example 1 towel, except that the 31 obtained by the synthesis example 5 is called the relative ion-binding body instead of the 32 mg of the phase 4, the sub-combination (4) is the same as the other formula, and the liquid light-absorbing pigment composition is obtained. . Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 1 to obtain a light absorbing material for evaluation. Example 3 In the same manner as in Example 1, except that 3 μg of the relative ion-bonded body obtained in Synthesis Example 6 was used instead of the 32 mg of the relative ion-bonded body obtained in Synthesis Example 4, liquid light was obtained. Absorbs the pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in the case of the shellfish, to obtain a light absorbing material for evaluation. Example 4 After dissolving 33 mg of the relative ion-conjugate (photo-stabilized cyanine 20-based dye) obtained in Synthesis Example 7 in 1 g of methyl ethyl ketone, 6 g of an adhesive (trade name "SZ6232 by Nippon Carbide Industry Co., Ltd." was added. "), 37mg of hardener (trade name "CK-102" by Nippon Carbide Industry Co., Ltd.), and llmg of hardening catalyst (trade name "CK-901" by Nippon Carbide Industry Co., Ltd.) A liquid light absorbing pigment composition was obtained. Then, it was coated on a poly-film by spin coating 27 200815537, dried at 8 ° C for 3 minutes to form a film thickness of 15 μm, and the surface of the coating film was covered with a poly film, and the cylinder was used. , and the light absorbing material for evaluation was prepared to evaluate the characteristics of the obtained light absorbing pigment composition. 5 Example 5 In the shell example 4, except that 32 mg of the relative ion-conjugate obtained by the synthesis example $ was used instead of the 33 mg of the relative ion-conjugate obtained in Synthesis Example 7, the other four were the same as in Example 4, and the liquid was obtained. Light absorbing pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 4 to obtain a light absorbing material for evaluation. [Example 6] In Example 4, except for the use of 32 mg of the relative ion-conjugate obtained in Synthesis Example 9 in place of the 33 mg of the relative ion-conjugate obtained in Synthesis Example 7, the same as in the case of Example 4, the liquid light absorption was obtained. Pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 4 to obtain a light absorbing material for evaluation. Example 7 After dissolving 31 mg of the relative ion-conjugated product (photo-stabilized cyanine dye) obtained in Synthesis Example 10 in 10 g of methyl ethyl ketone, 6 g of an adhesive (trade name "SZ6232" manufactured by Nippon Carbide Industry Co., Ltd.) was added. ), 36 mg of hardener (trade name "CK-102" manufactured by Nippon Carbide Industry Co., Ltd.), and l〇mg hardening catalyst (trade name rCK-9〇1 manufactured by Sakamoto Carbide Industry Co., Ltd.), After mixing, a liquid light absorbing pigment composition can be obtained. Then, it was coated on a polyester film by a spin coater, and dried at 8 ° C for 3 minutes to form a coating film having a film thickness of 28 200815537 15 μm, and then the surface of the coating film was covered with a poly (tetra) film, and was coated with a roller. The name of the light absorbing material for evaluation was prepared to evaluate the characteristics of the obtained light absorbing pigment composition. Example 8 5 A liquid light was obtained in the same manner as in Example 7 except that 30 mg of the relative ion-conjugate obtained in Synthesis Example 11 was used instead of the 31 mg of the relative ion-conjugate obtained in Synthesis Example 10. Absorbs the pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 7 to obtain a light absorbing material for evaluation. 10 Example 9 In the same manner as in Example 7, except that 30 mg of the relative ion-conjugate obtained in Synthesis Example 12 was used instead of the 31 mg of the relative ion-conjugate obtained in Synthesis Example 10, liquid light absorption was obtained. Pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 7 to obtain a light absorbing material for evaluation 15. Example 10 After dissolving 61 mg of the relative ion-conjugate (photo-stabilized cyanine dye) obtained in Synthesis Example 4 in 12 g of cyclopentanone, 6 g of an adhesive (trade name "SZ6233" manufactured by Sakamoto Carbide Industry Co., Ltd.) was added. ), 35 mg of a hardener (trade name "CK-102" manufactured by Nippon Carbon Chemical Co., Ltd.), and llmg of a hardening catalyst (trade name "CK-901" manufactured by Nippon Carbide Industry Co., Ltd.), after mixing A liquid light absorbing pigment composition can be obtained. Then, it was coated on a polyester film by a spin coater, and dried at 80 ° C for 3 minutes to form a coating film having a film thickness of 15 μm, and then the surface of the coating film was covered with a polyester film, and evaluated by a roller 29 200815537. The obtained light is absorbed and adhered to 'the characteristics of the light absorbing material for evaluation and the coloring matter composition. Example 11 In the actual example, except that the 59-mer relative ion "body obtained by the synthesis example 5 was used instead of the 61 mg of the relative ion-combined body obtained in Example 4, and both of them were implemented, the green light was obtained. In the same manner as in Example 10, a light-absorbing material for a film thickness of 15 was formed in the same manner as in Example 10.

Example 12 10 In the same manner as in Example 10 except that 59 mg of the relative ion-conjugate obtained in Synthesis Example 6 was used instead of the 61 mg of the relative ion-conjugate obtained in Synthesis Example 4, a liquid light was obtained. Absorbs the pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 10 to obtain a light absorbing material for evaluation. 15 Example 13 49 mg of the relative ion-conjugate (photo-stabilized cyanine dye) obtained in Synthesis Example 7 was dissolved in 10 g of S, and 6 g of an adhesive (trade name "SZ6233" manufactured by Nippon Carbide Industry Co., Ltd.) was added. ), 30 mg of hardener (trade name "CK-102" manufactured by Nippon Carbide Industry Co., Ltd.), and l〇mg hardened touch 20 medium (trade name "CK-901" manufactured by Nippon Carbide Industry Co., Ltd.), mixed A liquid light absorbing pigment composition can then be obtained. Then, it was coated on a polyester film by a spin coater, and dried at 80 ° C for 3 minutes to form a coating film having a film thickness of 15 μm, and then the surface of the coating film was covered with a polyester film, and adhered by a roller. A light absorbing material for evaluation was prepared to evaluate the characteristics of the obtained light absorbing composition 30 200815537. [Example 14] In Example 13, except that the 4711^ relative ion complex obtained in Synthesis Example 8 was used instead of the 49 mg relative ion complex obtained in Synthesis Example 7, the other 5 were the same as in Example 13 to obtain a liquid light. Absorbs the pigment composition. Further, a coating film having a film thickness of 16 μm was formed in the same manner as in Example 13 to obtain a light absorbing material for evaluation. Example 15 In the same manner as in Example 13 except that 48 mg of the relative ion 10 complex obtained in Synthesis Example 9 was used instead of the 49 mg of the relative ion-conjugate obtained in Synthesis Example 9, liquid light absorption was obtained. Pigment composition. Further, a coating film having a film thickness of 16 μm was formed in the same manner as in Example 13 to obtain a light absorbing material for evaluation. Example 16 15 38 mg of the relative ion-conjugated product (photo-stabilized cyanine dye) obtained in Synthesis Example 10 was dissolved in 1 g of methyl ethyl ketone, and '6 g of an adhesive was added (trade name "SZ6233 by Nippon Carbide Industry Co., Ltd." "), 33 mg of hardener (trade name "CK-102" manufactured by Nippon Carbide Industry Co., Ltd.), and l〇mg hardening catalyst (trade name "CK-901" by Nippon Carbide Industry Co., Ltd.), 20 After mixing, a liquid light absorbing pigment composition can be obtained. Then, it was coated on a polyester film by a spin coater, and dried at 8 ° C for 3 minutes to form a coating film having a film thickness of 15 μm, and then the surface of the coating film was covered with a polyester film, and the film was adhered thereto. A light absorbing material for evaluation was prepared to evaluate the characteristics of the obtained light absorbing pigment composition. 31 200815537 Example Π In Example 16, except that 37 mg of the relative ion-conjugate obtained in Synthesis Example 11 was used instead of the 38 mg of the relative ion-conjugate obtained in Synthesis Example 10, the liquid light was obtained in the same manner as in Example 16 to obtain a liquid light. Absorbs the pigment composition. Further, a coating film having a film thickness of 17 μm was formed in the same manner as in Example 16 to obtain a light-absorbing material for evaluation. Example 18 In the same manner as in Example 16 except that 38 mg of the relative ion-conjugate obtained in Synthesis Example 12 was used instead of the 38 mg of the relative ion-conjugate obtained in Synthesis Example 10, a liquid light was obtained. Absorbs the pigment composition. Further, a coating film having a film thickness of 17 μm was formed in the same manner as in Example 16 to obtain a light-absorbing material for evaluation. Example 19 After dissolving 24 mg of the relative ion-conjugate (photo-stabilized cyanine 15-based dye) obtained in Synthesis Example 4 as 4-cyclopentanone, 9.6 g of an adhesive (Japanese Carbide Industry Month) was added. The name "SZ6234") and 65]11 § hardener (trade name "CK-117" manufactured by Nippon Carbide Industry Co., Ltd.) can be mixed to obtain a liquid light absorbing pigment composition. Then, it was coated on a black coat film by a spin coater and dried at 8 ° C for 3 minutes to form a film 20 having a film thickness of 15 μm, and then covered with a film of a film to cover the surface of the film with a roller. The light absorbing material for evaluation was prepared by adhesion to evaluate the characteristics of the obtained light absorbing pigment composition. Example 20 In the yoke example 19, except that the 25 mg relative ion 32 200815537 conjugate obtained in Synthesis Example 5 was used instead of the 24 mg relative ion conjugate obtained in Synthesis Example 4, the same procedure as in Example 19 was carried out to prepare a liquid. The light absorbs the pigment composition. Further, a coating film having a film thickness of 5 μm was formed in the same manner as in Example 19 to obtain a light absorbing material for evaluation. [Example 21] In Example 19, liquid light absorption was obtained in the same manner as in Example 19 except that 23 mg of the relative ion-conjugate obtained in Synthesis Example 6 was used instead of the 24 mg of the relative ion-conjugate obtained in Synthesis Example 4. Pigment composition. Further, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 19 to obtain a light absorbing material for evaluation. Example 22 After dissolving 29 mg of the relative ion-conjugate (photo-stabilized cyanine dye) obtained in Synthesis Example 10 in 6.4 g of cyclopentanone, 9.6 g of an adhesive (trade name "SZ6234, manufactured by Nippon Carbide Industry Co., Ltd." was added. "), and 51 mg of a curing agent (trade name "CK-117" manufactured by the Carbide Industry Co., Ltd.), and a liquid light absorbing pigment composition can be obtained by mixing. Then, it was coated on a polyester film by a spin coater, and dried at 80 ° C for 3 minutes to form a coating film having a film thickness of 18 μm, and then the surface of the coating film was covered with a polyester film, and adhered by a roller. A light absorbing material for evaluation was prepared to evaluate the characteristics of the obtained light absorbing pigment group 20 composition. Example 23 In the same manner as in Example 22 except that 29 mg of the relative ion-conjugate obtained by the synthesis example was used instead of the 29 mg of the relative ion-conjugate obtained in Synthesis Example 10, a liquid light-absorbing pigment was obtained. Composition. Further, a coating film having a film thickness of 18 μπ 1 was formed in the same manner as in Example 22, and a light absorbing material for evaluation was obtained. Example 24 In the same manner as in Example 22 except that 28 mg of the relative ion-conjugate obtained in Synthesis Example 12 was used instead of the 29 mg of the relative ion-conjugate obtained in Synthesis Example 12, a liquid light-absorbing pigment was obtained. Composition. Further, a coating film having a film thickness of 8 μm was formed in the same manner as in Example 22 to obtain a light-absorbing material for evaluation. Example 25 10 After dissolving 30 mg of the relative ion-conjugated product (photo-stabilized cyanine dye) obtained in Synthesis Example 10 in 11.2 g of methyl ethyl ketone, 4.8 g of an adhesive (trade name manufactured by Sakamoto Synthetic Chemical Industry Co., Ltd.) was added. NICHIGO POLYESTER 15 • XI-0002”), 40mg hardener (trade name “CORONATE L-55E” manufactured by Nippon Polyurethane Industry Co., Ltd.), and 12mg hardening catalyst (di-n-butyltin dilaurate) ; produced by Tokyo Chemical Industry Co., Ltd.), after mixing, a liquid light absorbing pigment composition can be obtained. Then, it was coated on a polyester film by a spin coater, and dried at 80 ° C for 3 minutes to form a coating film having a film thickness of ι μ μπι, and then the surface of the coating film was covered with a polyester film, and the roller was used to make it. The light absorbing material for evaluation was prepared by adhesion to evaluate the characteristics of the obtained light absorbing pigment composition *20. Example 26 After dissolving 15.5 mg of the ionomer (photostabilized cyanine dye) obtained in Synthesis Example 13 in 10 g of methyl ethyl ketone, 6 g of an adhesive (trade name "SZ6232" manufactured by Nippon Carbide Industry Co., Ltd.) was added. 26mg hardener (trade name "CK-102" made by Japan Carbo Industries Co., Ltd., 34, 200815537), and 15mg hardening catalyst (trade name "CK-901" by Nippon Carbide Industry Co., Ltd.) A liquid light absorbing pigment composition was obtained. Then, it was coated on a polyester film by a spin coater, and dried at 8 ° C for 3 minutes to form a coating film having a film thickness of 5 17 μm, and then the surface of the coating film was covered with a polyester film, and the film was coated with a roller. The light absorbing material for evaluation was prepared by adhesion to evaluate the characteristics of the obtained light absorbing pigment composition. Example 27 _ After 15 mg of the relative ion-conjugate (photo-stabilized flower 10 cyanine dye) obtained in the synthesis example was dissolved in 8 g of methyl ethyl ketone, an adhesive (6 g of the product name of the product of the product of the product of the product) "SZ6472", the product name "CELLOXIDE 2021P" manufactured by DAICEL Chemical Industry Co., Ltd. of 2.4g, and the "ARON OXETANE OXT-221" by the East Asia Synthetic Co., Ltd. of 24g, 24mg hardener (Japanese carbide) Industrial Co., Ltd., product name 15 "CK_102", and hardening catalyst (12mg of the product name "CK-901" manufactured by Sakamoto Carbide Industry Co., Ltd., and 16.16g of DOW Chemical Japan Co., Ltd. The product name "CIRACUREUVI-6992"), after mixing, can produce a liquid light absorbing pigment composition. Then, it was coated on a S-film by a spin coater and dried at 80 C for 3 minutes to form a film having a film thickness of 25 μm. Then, the surface of the film was covered with a glass plate and adhered by a roller. - The light-absorbing material for evaluation was obtained by using a transfer type ultraviolet curing device manufactured by USM Electric Co., Ltd. to obtain characteristics of the obtained light-absorbing pigment composition. Example 28 35 200815537 15 mg of the relative ion-conjugated (photostabilized cyanine dye) obtained in the synthesis example ίο was dissolved in 8 g of methyl ethyl ketone, and then an adhesive (6 g of the product name "SZ6472" manufactured by Nippon Carbide Industry Co., Ltd. was added. 2.4g of the Japanese epoxy resin company's trade name "ΕΠΚΟΤΕ 828", and 0.24g of the East Asia Synthetic 5 Co., Ltd. trade name "ARON OXETANE OXT «221"), 24mg hardener (Japan's carbide industry) The product name "CK-102" manufactured by the company, and the hardening catalyst (12-mg of the product name "CK-901" made by Japan Carbo Industries Co., Ltd., and the product name of 0.05g Sanshin Chemical Co., Ltd." SI-45L"), after mixing, a liquid light absorbing pigment composition can be obtained. After that, it was applied to a polyester film by a spin coater, and dried at 80 ° C for 3 minutes to form a coating film having a film thickness of 24 μm, and then the surface of the coating film was covered with a glass plate and adhered by a roller. The film was cured at 80 ° C (1 hour) to obtain a light-absorbing material for evaluation, and the properties of the obtained light-absorbing pigment composition were evaluated. 15 Example 29 After 15 mg of the relative ion-conjugate (photo-stabilized cyanine dye) obtained in Synthesis Example 10 was dissolved in 12 g of methyl ethyl ketone, an adhesive (6 g of the product name "SZ6472" manufactured by Nippon Carbide Industry Co., Ltd. was added. 2.4g of the product name "CELLOXIDE 2021P" manufactured by DAICEL Chemical Industry Co., Ltd., and 0.24g of the product name "ARON OXETANE OXT-221" manufactured by Toagos Corporation, and the hardener (24mg of the Japanese carbide industry) The product name "CK-102" manufactured by the company, and the hardening catalyst (12-mg of the product name "CK-901" made by Japan Carbo Industries Co., Ltd., and the product name of the new product of 0.05g Sanshin Chemical Co., Ltd." SI-45L"), after mixing, can produce liquid light absorption 36 200815537 Pigment composition. Then, it was coated on a polyester film by a spin coater, and dried at 80 C for 3 minutes to form a film having a film thickness of 16 μπΐ2, and then the surface of the coating film was covered with a glass plate, and adhered by a roller to 8 〇〇. CT (1 hour) was allowed to harden, and a light absorbing material for evaluation was prepared to evaluate the obtained light absorption and the characteristics of the 5 coloring matter composition. Comparative Example 1 A liquid light absorbing pigment composition was prepared in the same manner as in Example 4 except that 35 mg of the cyanine dye E2 was used instead of the 33 lng of the relative ion conjugate obtained in Synthesis Example 7 φ. However, the composition is not completely dissolved. Using this composition, a coating film having a film thickness of 15 μm was formed in the same manner as in Example 4 to obtain a light absorbing material for evaluation. Comparative Example 2 In Example 7, except that 35 mg of cyanine dye Ε3 was used instead of 31 mg of the relative ion-conjugate obtained in Synthesis Example 1, the liquid composition of the light absorbing pigment was obtained in the same manner as in Example 7 Things. Further, a coating film having a film thickness of ημηι was formed in the same manner as in Example 7 to obtain a light absorbing material for evaluation. Comparative Example 3 In Example 26, except that 6 mg of cyanine dye Ε4 was used instead of the 15.5 mS relative ion-conjugate obtained in Synthesis Example '13, the same as Example 26 2〇, the liquid of the light absorbing pigment was obtained. Composition. Further, a coating film having a film thickness of 18 μm was formed in the same manner as in Example 26 to obtain a light absorbing material for evaluation. Comparative Example 4 In Example 29, a liquid composition of a light absorbing pigment was obtained in the same manner as in Example 29 except that 10 mg of the cyanine dye oxime 3 was used instead of the 15 mg of the relative ion conjugate obtained in Synthesis Example 37 20081553710. . Further, a coating film having a film thickness of 16 μm was formed in the same manner as in Example 29 to obtain a light absorbing material for evaluation. [Evaluation of Light Absorbing Material] 5 In order to investigate changes in the light absorption properties of the light absorbing materials obtained in Examples 1 to 26 and Comparative Examples 1 to 3 with time, the following simulation test was carried out. First, the absorbance of each light absorbing material at a specific wavelength (measurement wavelength: 550 nm, 100 nm) was measured using a spectrophotometer as the absorbance before curing. Thereafter, the absorbance was measured for each of the light absorbing materials which were allowed to stand for 7 days in the dark at room temperature, and the absorbance after curing was measured by the same method as the above. Then, each of the light-absorbing materials after the curing was measured by the light stability tester (trade name "LT-120" manufactured by the company Nagano Scientific Machinery Co., Ltd.) in the same manner as described above, and the measurement was performed after irradiation for 100 hours at 50001x. The absorbance (A) is measured by the small environmental tester (trade name 15 "SU-240" manufactured by TABAI ESPEC Co., Ltd.), and the absorbance (B) after standing at 80 ° C for 1 hour, and the use of small The environmental tester (trade name "SU-220" manufactured by TABAI ESPEC Co., Ltd.) was measured for absorbance (C) after standing at 90 ° C for 1 hour at 90 ° C. Next, using the absorbance obtained above, it is calculated (absorbance after curing 20 luminosity / absorbance before curing) χ 100 = residual absorbance after curing (%), (absorbance (Α) / absorbance before curing) χ 100 == Residual absorbance after the test Α (%), (absorbance (Β) / absorbance before curing) >< 1 〇〇 = absorbance residual ratio B (%) after the test, and (absorbance (C) / before curing Absorbance) xl00 = absorbance residual rate C (%) after the test. The results are shown in Tables 3 and 4. 38 200815537 [Table 3] Absorbance Residual Rate after Solidification of Table 3 (%) Absorbance Residual Rate after Test (%) ABC Measurement Wavelength 100om lOOOnm lOOOnm lOOOnm Example 1 94 85 89 89 Example 2 90 83 85 85 Implementation Example 3 95 86 90 90 Example 4 100 98 100 100 Example 5 98 98 98 96 Example 6 100 99 100 100 Example 7 100 98 100 100 Example 8 99 98 99 99 Example 9 100 99 100 100 Example 10 96 90 94 95 Example 11 96 94 95 95 Example 12 99 98 99 98 Example 13 100 98 99 100 Example 14 98 97 98 97 Example 15 100 100 100 100 Example 16 100 95 98 100 Example 17 99 98 99 98 Example 18 100 100 100 100 Example 19 88 74 82 79 Example 20 86 73 80 78 Example 21 88 76 82 81 Example 22 95 91 95 95 Example 23 94 90 94 93 Example 24 97 92 97 96 Example 25 99 95 77 87 Comparative Example 1 71 65 53 49 Comparative Example 2 98 93 66 21 39 5 200815537 [Table 4] Table 4

In order to investigate the light absorption properties of the light absorbing materials obtained in Examples 27 to 29 and Comparative Example 4, the following simulation tests were carried out. First, the absorbance at each specific wavelength (measurement wavelength: 100 nm) of each light absorbing material was measured using a spectrophotometer as the absorbance before the test. Then, for each of the light-absorbing materials, the absorbance of 10 after irradiation for 100 hours at 50001X was measured using a light stability tester (trade name "LT-120" manufactured by the company Nagano Scientific Machinery Co., Ltd.). a) Using a small-scale environmental tester (trade name "SU-240" manufactured by TABAI ESPEC Co., Ltd.), measuring the absorbance (B) after standing at 80 ° C for 100 hours, and using a small environmental tester (TABAI ESPEC) The product name "su-220" manufactured by the company was measured for absorbance (C) after standing at 90 ° C for 100 hours at 90 ° C. 15 Then, using the absorbance obtained above, the absorbance (A)/absorbance before the test χ100 = the absorbance residual ratio A (%) after the test, (absorbance (B) / absorbance before the test) > 100 = absorbance residual ratio B (%) after the test, and (absorbance (C) / absorbance before the test) x lO 〇 = absorbance residual ratio C (%) after the test. The results are shown in Table 5. 40 20 200815537 [Table 5] Table 5 Measurement wavelength - ^ 福 i i5 〇〇 nm L absorbance residual B lOOOnm rate (%) __C 10 OOtvm Example 27 _ 67 - ^ 94 Α VUV / xllll 87 Example 28 ^ ^ >fei! 9 Q —_ 87 93 匕 匕 匕 1 — 1j — 71 72 Comparative Example 4 49 70 馨 According to the results shown in Tables 3 and 4, the 5 light absorption obtained in Example 26 Compared with the light absorbing materials obtained in Comparative Examples 1 to 3, the absorbance residual ratio after curing and the absorbance residual ratios A to C after the test were all high, and thus the light obtained in Examples 1 to 26 was high. The absorbent material can sufficiently suppress the decrease in light absorption energy. Further, as is clear from the results shown in the fifth table, the light absorbing materials obtained in Examples 27 to 29 were compared with the light absorbing materials obtained in Comparative Example 4, and the absorbance remained in the absorbance ratios A to C after the test. Since the rate was all high, the light absorbing materials obtained in Examples 27 to 29 were able to sufficiently suppress the decrease in light absorption energy. # [Circular simple description 1 None [Main component symbol description] A None 41

Claims (1)

200815537 X. Patent application scope: 1. A light-absorbing pigment composition containing photo-stabilized cyanine pigments and adhesives. 2. The light absorbing pigment composition according to claim 1, wherein the light-stabilized cyanine dye is a substituted ionomer of a benzenedithiol metal complex anion and a cyanine dye cation. 3. The light absorbing pigment composition of claim 2, wherein the aforesaid substituted benzenedithiol metal complex anion is of the formula (1) ·· 【化1】 L 02 _ (wherein R 1 and R 2 are each independently and represent an alkyl group having 1 to 6 carbon atoms, an alkylamino group having 1 to 8 carbon atoms, a morpholinyl group which may have a substituent, and may have a substituent. a pyrrolidinyl group which may have a substituent, a thiofenoflavinyl group which may have a substituent, a phenyl group which may have a substituent or a phenyl group which may have a substituent, and 1^ represents a transition metal atom) Represents a substituted benzenedithiol metal complex anion. 4. The composition of the light absorbing pigment according to any one of the items i to 3 of the patent application scope 42 200815537 VII. Designation of representative representatives: (1) The representative representative of the case is: (No). (2) A brief description of the symbol of the representative figure: None 8. If there is a chemical formula in this case, please disclose the chemical formula that best shows the invention: