Composition, resin composition, optical member, and method for manufacturing optical member

JP2025029878APending Publication Date: 2025-03-07THE JAPAN STEEL WORKS LTD
View PDF 1 Cites 0 Cited by

Patent Information

Application Number
JP2023134753
Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-08-22
Publication Date
2025-03-07

AI Technical Summary

Benefits of technology

【0011】 本開示によれば、特に、近赤外領域での光吸収性に優れた組成物、当該組成物を含み成膜性に優れた樹脂組成物、近赤外領域での光吸収性に優れた光学部材及び光学部材の製造方法を提供することができる。

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure 2025029878000001_ABST
    Figure 2025029878000001_ABST
Patent Text Reader

Abstract

To provide a composition which is excellent in light absorption in a near-infrared region, a resin composition, an optical member, and a method for manufacturing an optical member.SOLUTION: A composition contains a compound represented by the following formula (1), a dispersant, a light absorber formed of copper ions, and an organic solvent, wherein transmittance based on measurement by 1 cm cell so that solid content concentration is at least one concentration of 5 g / L or more satisfies the following (I) and (II). (I) Transmittance maximum value at a wavelength of 800 nm to 1,100 nm of 1% or less. (II) Transmittance minimum value at a wavelength of 400 nm to 600 nm of 80% or more. In the formula (1), R1 is an alkyl group having 1 to 4 carbon atoms, or an oxyalkyl group having 1 to 4 carbon atoms.SELECTED DRAWING: Figure 1
Need to check novelty before this filing date? Find Prior Art

Description

[Technical field]

[0001] The present invention relates to a composition, a resin composition, an optical member, and a method for producing an optical member. [Background technology]

[0002] Digital cameras and the like use imaging elements such as CCD and CMOS. Since these imaging elements are sensitive to near-infrared light, near-infrared absorbing film is placed on the light-receiving surface side of the imaging element to block near-infrared light. As a near-infrared absorbing film, for example, a film in which a near-infrared absorbing agent is dispersed in a resin is known.

[0003] For example, Patent Document 1 describes an optical filter having a UV-IR absorbing layer containing a UV-IR absorber capable of absorbing ultraviolet and infrared rays, which is formed by at least one acid selected from phosphonic acid and sulfonic acid and copper ions, and which has predetermined optical properties and a haze of 5% or less. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2020-112826 A Summary of the Invention [Problem to be solved by the invention]

[0005] Near-infrared absorbents are required to be applied in various fields, and to be supplied in a solution form for application to various substrates. In addition, the required thickness varies, and light absorbents with excellent contrast between infrared absorption and visible light transmission are required.

[0006] In particular, an object of the present disclosure is to provide a composition having excellent light absorbency in the near-infrared region, a resin composition containing the composition and having excellent film-forming properties, an optical component having excellent light absorbency in the near-infrared region, and a method for producing an optical component. [Means for solving the problem]

[0007] A composition according to one embodiment of the present disclosure comprises: The composition contains a light absorber formed by a compound represented by the following formula (1), a dispersant, and copper ions, and an organic solvent, The solid content is set to at least one concentration of 5 g / L or more, and the transmittance measured in a 1 cm cell satisfies the following (I) and (II). (I) The maximum transmittance in the wavelength range of 800 nm to 1100 nm is 1% or less. (II) The minimum transmittance in the wavelength range of 400 nm to 600 nm is 80% or more. [ka] In the formula (1), R 1 is an alkyl group having 1 to 4 carbon atoms or an oxyalkyl group having 1 to 4 carbon atoms.

[0008] A resin composition according to one embodiment of the present disclosure contains the above composition and a resin.

[0009] An optical member according to one aspect of the present disclosure includes a cured product of the resin composition.

[0010] A method for producing an optical member according to one embodiment of the present disclosure includes applying the resin composition onto a substrate. Effect of the Invention

[0011] According to the present disclosure, it is possible to provide a composition having excellent light absorbency, particularly in the near-infrared region, a resin composition containing the composition and having excellent film-forming properties, an optical component having excellent light absorbency in the near-infrared region, and a method for manufacturing an optical component. [Brief description of the drawings]

[0012] [Figure 1] 1 is a transmittance spectrum of Example 1-2. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] The light absorbent of the present disclosure, the method for producing the light absorbent, the composition, and the optical member will be described in this order below. In the present disclosure, the "compound represented by formula (1)" may be referred to as "compound (1)". The same applies to other compounds. In the present disclosure, "curing" includes curing via a crosslinking reaction as well as curing (solidification) by removing a solvent. In the present disclosure, the "solid content" in a composition refers to components other than the solvent. Furthermore, unless otherwise specified, the symbol "~" indicating a numerical range includes the lower limit and the upper limit.

[0014] [Composition] The composition of the present disclosure contains a compound represented by the following formula (1), a dispersant, a light absorber formed by copper ions, and an organic solvent, A composition having at least one concentration of a solid content of 5 g / L or more and having a transmittance measured in a 1 cm cell that satisfies the following (I) and (II): (I) The maximum transmittance in the wavelength range of 800 nm to 1100 nm is 1% or less. (II) The minimum transmittance in the wavelength range of 400 nm to 600 nm is 80% or more. [ka] In the formula (1), R 1 is an alkyl group having 1 to 4 carbon atoms or an oxyalkyl group having 1 to 4 carbon atoms.

[0015] In the above composition, the light absorber is formed of a compound represented by formula (1), a dispersant, and copper ions. By containing the compound represented by formula (1), the composition has excellent light transmittance in the visible light region and excellent light absorption in a wide range of the near infrared region. By using such a light absorber, for example, an increase in the transmittance of near infrared light at long wavelengths of 1000 nm or more can be suppressed. In addition, by containing a dispersant, aggregation of the light absorbers is suppressed, and the light absorbers are uniformly dispersed. As a result, the composition can achieve optical properties such as a maximum transmittance of 1% or less at wavelengths of 800 nm to 1100 nm and a minimum transmittance of 85% or more at wavelengths of 400 nm to 600 nm.

[0016] The composition of the present disclosure contains at least a light absorbing agent and an organic solvent, and may further contain other compounds, etc., within the scope of the effects of the present disclosure. Each component will be described below.

[0017] <Light absorber> (Compound (1)) Compound (1) constitutes a part of the light absorber. Compound (1) has two OH groups and R 1 By using the compound (1) having a small molecular weight, a composition having excellent transmittance of light in the visible region can be obtained. 1 When the compound (1) is a phenyl group, there is a risk of yellowing when it is combined with a material having a hydroxyl group, but the use of the compound (1) suppresses the risk of yellowing and allows the compound (1) to be used in combination with a wider range of materials. In addition, the use of the compound (1) reduces the molecular size of the light absorber, and the desired optical properties can be obtained at a low concentration. Therefore, even when the compound (1) is combined with a resin, etc., which will be described later, aggregation between the light absorbers is suppressed, and low-haze optical components can be manufactured.

[0018] R 1Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, and a butoxy group. From the viewpoints of optical properties and low haze, a methyl group, an ethyl group, a butyl group, a methoxy group, an ethoxy group, or a butoxy group is preferable, a methyl group, an ethyl group, or a methoxy group is more preferable, a methyl group or an ethyl group is even more preferable, and a methyl group is particularly preferable. The compound (1) can be used alone or in combination of two or more kinds.

[0019] (Dispersant) In the present disclosure, a dispersant is a compound that constitutes a part of the light absorber and improves the dispersibility of the light absorber. The dispersant may affect the spectral properties of the light absorber. From the viewpoints of dispersibility and dispersion stability of the light absorbent, compatibility with the resin, and infrared absorbing ability of the light absorbent, the dispersant is preferably the following compound (2).

[0020] [ka] however, R 11 and R 12 are each independently an oxyalkyl group, a polyoxyalkyl group, or a polyester group; or R 11 is a hydroxyl group, and R 12 is an oxyalkyl group having 8 or more carbon atoms, a polyoxyalkyl group having 8 or more carbon atoms, or a polyester group.

[0021] R 11 and R 12 The oxyalkyl group in is -OR 21 R 21 is an alkyl group. From the viewpoint of dispersibility, R 21 R is preferably an alkyl group having 1 to 36 carbon atoms, more preferably an alkyl group having 1 to 24 carbon atoms, and further preferably an alkyl group having 2 to 12 carbon atoms. 11 If is a hydroxyl group, R 12 The carbon number of the oxyalkyl group of R is 8 or more from the viewpoint of dispersibility.21 is preferably an alkyl group having 8 to 36 carbon atoms, more preferably an alkyl group having 8 to 24 carbon atoms, and further preferably an alkyl group having 8 to 12 carbon atoms. Specific examples of the alkyl group include an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a dodecyl group, a hexadecyl group, an octadecyl group, and a tetracosyl group.

[0022] R 11 and R 12 The polyoxyalkyl group in 22 ) n -OR 23 Preferably, R 22 are each independently an alkylene group having 1 to 6 carbon atoms; R 23 R is an alkyl group having 1 to 36 carbon atoms, and n is an integer of 1 or more. 22 Specific examples of the group include a methylene group, an ethylene group, a propylene group, and a butylene group. From the standpoint of dispersibility, the methylene group, the ethylene group, and the propylene group are preferred, and the ethylene group is more preferred. R 23 The alkyl group of R 21 is the same as: n may be 1 or more, is preferably 1-100, and more preferably 1-50. Furthermore, R 11 If is a hydroxyl group, R 12 The number of carbon atoms in the polyoxyalkyl group in R 22 The number of carbon atoms in (if there are multiple, the total number of carbon atoms) and R 23 The total number of carbon atoms is 8 or more.

[0023] R 11 and R 12 The polyester group in 24 [OC(=O)R 25 C(=O)OR 26 ] m R 27 Preferably, R 24 is a single bond or an alkylene group, R 25 is an alkylene group or an arylene group, R 26is an alkylene group or an arylene group, R 27 When connecting with R 27 is a hydrogen atom, an alkyl group or -R 28 OH and R 28 is an alkylene group, and m is an integer of 1 or more. 27 The alkyl group in R 21 Same as R 24 , R 25 , R 26 , R 28 The alkylene group in R 22 Same as R 25 , R 26 The arylene group in is preferably a phenylene group or a naphthylene group.

[0024] Specific examples of dispersants include diethyl phosphate, dibutyl phosphate, Plysurf A208F (polyoxyethylene alkyl (C8) ether phosphate), Plysurf A208B (polyoxyethylene lauryl ether phosphate), Plysurf A208N (polyoxyalkylene alkyl ether phosphate), Plysurf A219B (polyoxyalkylene alkyl ether phosphate) (all manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), and the like.

[0025] The molecular weight of the dispersant may be appropriately adjusted depending on the resin to be combined, etc. From the viewpoint of the infrared absorbing ability of the light absorbent, the molecular weight is preferably 5,000 or less, more preferably 3,000 or less, and even more preferably 2,000 or less. On the other hand, from the viewpoint of compatibility with the resin, the molecular weight of the dispersant is preferably 150 or more.

[0026] (Copper ions) The light absorber contains copper ions, which are preferably supplied from a copper compound capable of producing copper ions (also referred to as a copper ion source). The copper ion source is preferably a dissociable copper compound (copper salt). The copper compound may contain either a monovalent copper ion or a divalent copper ion, and among these, a copper salt capable of supplying a divalent copper ion is preferred. Examples of copper compounds include organic salts such as copper acetate, copper citrate, copper gluconate, anhydrous copper acetate, anhydrous copper formate, anhydrous copper stearate, anhydrous copper benzoate, anhydrous copper ethylacetoacetate, anhydrous copper pyrophosphate, anhydrous copper naphthenate, anhydrous copper citrate, and copper acetylacetonate, or hydrates of the organic salts; inorganic salts such as copper oxide, copper chloride, copper bromide, copper iodide, copper sulfate, copper nitrate, and basic copper carbonate, or hydrates of the inorganic salts. The copper ion sources can be used alone or in combination of two or more.

[0027] <Blending ratio> The molar ratio of compound (1) to copper ions in the composition (compound (1) / copper ions) is preferably from 0.1 to 1, more preferably from 0.2 to 0.95, since it is easy to adjust the transmittance within a predetermined range. In the composition, the molar ratio of the total number of moles (T) of the dispersant and the compound (1) to the copper ions (T / copper ions) is preferably 1-6. The molar ratio of the dispersant to compound (1) in the composition (dispersant / compound (1)) is preferably from 10 to 0.1, more preferably from 2 to 0.3, from the viewpoints of compatibility, infrared absorption ability, and visible light transparency. The molar ratio of the dispersant to the copper ions in the composition (dispersant / copper ions) is preferably from 1 / 4 to 4 / 1, and more preferably from 1 / 2 to 2 / 1. If the molar ratio of the dispersant to the copper ions is equal to or greater than the lower limit, the copper ions coordinated with one or more dispersants become the main component of the light absorber, and therefore, if the molar ratio is equal to or greater than the lower limit, the light absorber has excellent compatibility with the resin. Although not limited thereto, it has been observed that the dispersant is monodentate or bidentate with respect to the copper ion.

[0028] <Method of manufacturing light absorbent> The method for producing the light absorber is not particularly limited. For example, a method of preparing a solution containing a copper ion source, compound (1) and a dispersant, and reacting the copper ions, compound (1) and dispersant in the solution can be mentioned. By the above method, the light absorber can be obtained in a good yield by a simple method.

[0029] The solvent may be appropriately selected from among solvents capable of dissolving or dispersing the copper ion source, compound (1) and dispersant. Examples of the solvent include aromatic compounds such as benzene, toluene, and xylene; alcohols such as methanol, ethanol, and propanol; glycol ethers such as methyl cellosolve and ethyl cellosolve; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, and tetrahydrofuran; ketones such as acetone and methyl ethyl ketone; esters such as ethyl acetate; and hydrocarbon solvents such as hexane. The solvent may be a single solvent or a mixture of two or more solvents. In the present production method, a mixed solvent of alcohols and the above aromatic compounds is preferred. A cyclic ester solvent such as γ-butyrolactone may also be added.

[0030] The copper ion source, compound (1), and dispersant are added to the above solvent, and the mixture is reacted by heating. The reaction conditions are not particularly limited, and the mixture is heated and stirred at 40 to 120°C for about 1 to 24 hours to form a complex. The solution after the reaction may be heated or otherwise purified to remove the solvent, if necessary. The light absorbent can be suitably produced by the above method.

[0031] The content of the light absorbent in the composition may be appropriately adjusted depending on the application of the optical component to be obtained, etc. In order to achieve both the dispersibility of the light absorbent and the infrared absorbing ability of the optical component, the content of the light absorbent is preferably 10 to 90 mass %, more preferably 30 to 80 mass %, based on the total amount of the composition excluding the solvent.

[0032] <Organic solvent> The present composition contains an organic solvent from the viewpoints of suppressing aggregation of the light absorbent and coating properties of the composition. The organic solvent may be appropriately selected from the viewpoints of affinity with the resin and viscosity required for the composition. In the present composition, it is preferable to include a low polarity solvent having a dielectric constant of less than 8 from the viewpoints of dispersibility and solubility. Examples of solvents having a dielectric constant of less than 8 include benzene, toluene, xylene, anisole, cyclohexane, hexane, heptane, diethyl ether, etc., which can be used alone or in combination of two or more. In addition, a solvent having a dielectric constant of 8 or more may be used in combination. Examples of solvents having a dielectric constant of 8 or more include N,N-dimethylformamide, methyl ethyl ketone, dichloromethane, ethanol, etc. Note that the dielectric constant in the present disclosure is a value measured at 25°C.

[0033] <Other ingredients> The composition of the present disclosure may contain other components within the range in which the effects of the present disclosure are exhibited. Examples of other components that may be contained in the composition include an antioxidant, a surfactant, and a silane coupling agent. The antioxidant can be appropriately selected from known antioxidants, and specific examples thereof include hindered phenol-based antioxidants, hindered amine-based antioxidants, phosphorus-based antioxidants, and sulfur-based antioxidants. The surfactant may be an anionic, cationic, nonionic, or amphoteric surfactant. In terms of compatibility with the light absorber of the present disclosure, a phosphate ester type anionic surfactant is preferred. The silane coupling agent can be appropriately selected and used depending on the resin to be combined, the material of the base material, etc. Specific examples of the silane coupling agent include diethoxydimethylsilane, dimethoxydimethylsilane, and hexyltrimethoxysilane.

[0034] <Spectral characteristics of the composition> The composition has at least one concentration having a solids concentration of 5 g / L or more, and the transmittance measured in a 1 cm cell satisfies the following (I) and (II). (I) The maximum transmittance in the wavelength range of 800 nm to 1100 nm is 1% or less. (II) The minimum transmittance in the wavelength range of 400 nm to 600 nm is 80% or more. By using the above light absorbing material, the present composition has excellent near-infrared absorbing properties in a wide range of wavelengths from 800 nm to 1100 nm. The transmittance characteristics can be adjusted, for example, by the type of compound (1), the type of dispersant, the molar ratio of compound (1) to copper ions, and the like.

[0035] As described above, the composition of the present disclosure has excellent near-infrared absorbing properties, and can be used, for example, in combination with a resin described below to form an optical component with excellent near-infrared absorbing ability.

[0036] [Resin composition] The resin composition of the present disclosure is characterized by containing the above-mentioned composition and a resin. The resin composition is suitable for producing an optical component having excellent light absorption properties in a wide range of the near-infrared region. The resin composition contains at least the above composition and a resin, and may further contain other compounds, etc., within the scope of the effects of the present disclosure. Note that the composition configuration is as described above, and therefore will not be described here.

[0037] <Resin> The resin is a matrix resin in the optical member described below, and can be appropriately selected depending on the application of the optical member, etc. The resin may be any of a thermoplastic resin, a thermosetting resin, and a photocurable resin. The resin is preferably a transparent resin, and when the resin is made into a film having a thickness of 0.1 mm, the total light transmittance (JIS K7105) is preferably 75% or more, more preferably 78% or more, and even more preferably 80% or more.

[0038] Resins that can be suitably used in the present resin composition include, for example, polyimide resin, polyester resin, acrylic resin, epoxy resin, polyurethane resin, silicone resin, cellulose, polycarbonate resin, polyethylene terephthalate (PET) resin, polycarbonate resin (PC), cycloolefin copolymer (COP), and the like. Among these, acrylic resin, epoxy resin, silicone resin, cellulose resin, polyimide resin, polycarbonate resin, and cycloolefin polymer are preferred, and from the viewpoint of superior compatibility, acrylic resin, silicone resin, cellulose, and polyimide resin are more preferred, and further, from the viewpoint of impact resistance, polyimide resin and cellulose are preferred.

[0039] In addition, from the viewpoint of further improving compatibility, the weight average molecular weight of the resin is preferably 100,000 or less, more preferably 50,000 or less, and even more preferably 30,000 or less. Although there is no particular lower limit to the weight average molecular weight of the resin, from the viewpoint of the mechanical strength of the optical member, it is usually 1,000 or more, and preferably 2,000 or more.

[0040] The content of the resin in the resin composition is preferably 10 to 90 mass %, more preferably 20 to 70 mass %, based on the total amount of the resin composition excluding the solvent. The solvent is adjusted depending on the desired viscosity of the resin composition, etc. From the viewpoint of film-forming properties, the viscosity of the composition at 25° C. is preferably 1,000 to 100,000 mPa·s, and more preferably 15,000 to 80,000 mPa·s.

[0041] The resin composition may also contain a dye or the like in order to adjust the spectral characteristics. The dye can be appropriately selected and used depending on the application of the optical member to be manufactured. In order to further improve the infrared absorbing ability, for example, an organic dye that absorbs light with a wavelength of 650 to 800 nm can be used. Examples of such dyes include phthalocyanine dyes and squarylium dyes. Specific examples of phthalocyanine dyes and squarylium dyes include, for example, the compounds described in JP-A-2023-27337, the near-infrared absorbents described in JP-A-2023-013321, and the near-infrared absorbing dyes described in JP-A-2021-177243.

[0042] By using the above organic dyes in combination, for example, a resin composition that satisfies (III) in addition to the above (I) and (II) can be obtained. (III) The average transmittance in the wavelength range of 700 nm to 800 nm is 5% or less.

[0043] When an organic dye is used, the ratio of the organic dye is preferably from 10 to 90 parts by mass, and more preferably from 20 to 70 parts by mass, relative to 100 parts by mass of the light absorbing agent.

[0044] [Optical components] The optical member of the present disclosure includes a cured product of the resin composition. The cured product may be a product obtained by removing an organic solvent from the resin composition and curing the resin composition, or may be a product obtained by curing a curable resin component through a crosslinking reaction. The optical member has excellent surface uniformity of optical properties because the light absorbent is uniformly dispersed.

[0045] The shape of the optical member may be appropriately designed depending on the application, etc. For example, it may be in the shape of a lens such as a convex lens or a concave lens, a prism, or the like, or in the shape of a sheet having fine concave-convex processing such as a prism sheet or a Fresnel lens, or in the shape of a film (membrane) having a flat surface.

[0046] When this optical member is made into a film having a thickness of 130 μm or less, The maximum transmittance is 1% or less at wavelengths of 800 nm to 1100 nm. It is preferable that the minimum transmittance in the wavelength range of 400 nm to 600 nm is 80% or more.

[0047] The method for producing the optical member may be appropriately selected depending on the shape of the optical member, etc. For example, in the case of lenses, prisms, etc., various molding methods such as injection molding can be used. On the other hand, a flat film-like optical component preferably includes, for example, a step of applying the present composition in a paste or varnish form on a substrate. This method makes it possible to easily form a flat film on a desired substrate. The coating of the present composition is dried and, if necessary, subjected to a curing reaction to obtain a film-like optical component. A sheet shape having fine irregularities can be obtained, for example, by shaping the coating film using a mold or the like.

[0048] Since the optical member has excellent optical properties, it can be suitably used as a near-infrared absorbing film arranged on the light receiving surface side of an imaging element such as a CCD or a CMOS. In addition, since it has excellent infrared absorbing ability and high visible light transmittance, it can also be suitably used as a heat absorbing member. Furthermore, an optical member using a polyimide resin as a resin has excellent mechanical strength and heat resistance, so it can be suitably used for the above-mentioned applications.

[0049] The present invention will be explained in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples.

[0050] [Example 1: Production of compositions and optical components] 1.60 g of copper (II) acetate monohydrate was dissolved in a mixed solution of 30 g of tetrahydrofuran (manufactured by Wako Pure Chemical Industries, Ltd.) and 30 g of toluene (manufactured by Wako Pure Chemical Industries, Ltd.), and the solution was stirred at room temperature for 10 minutes to prepare solution a. In addition, 0.7 g of methylphosphonic acid (manufactured by Wako Pure Chemical Industries, Ltd.), 1.0 g of Plysurf A208F (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) as a dispersant, 0.3 g of dibutyl phosphate (manufactured by Tokyo Chemical Industry Co., Ltd.) as a silane coupling agent, and 2.0 g of dimethoxydimethylsilane (manufactured by Tokyo Chemical Industry Co., Ltd.) as a silane coupling agent were dissolved in 10 g of tetrahydrofuran (manufactured by Wako Pure Chemical Industries, Ltd.), and the solution was prepared by stirring at room temperature for 10 minutes. Solution a and solution b were filled into a 500 ml eggplant flask, stirred at room temperature for 1 min, and then heated in an oil bath at 70°C for 3 h with stirring. After that, impurities such as unreacted substances and by-products were removed, the solvent was removed, and the solution was solidified. After that, 13.0 g of toluene (manufactured by Wako Pure Chemical Industries) was added and stirred for 1 h to obtain 14.1 g of green near-infrared absorbing solution c.

[0051] <Transmittance measurement> 0.25 g of the obtained near-infrared absorbing solution was filled into a quartz cell of 1 cm x 1 cm, 3 ml of toluene was added and stirred, and the light transmittance was measured (Example 1-2 in Table 1). For reference, a sample in which 3 ml of toluene was filled into a quartz cell of 1 cm x 1 cm was used. The spectroscopic spectrum of the near-infrared absorbing coating film of Example 1-2 is shown in Figure 1. The maximum transmittance of 800-1100 nm was 0.4%, and the minimum transmittance of 400-600 nm was 94.6%, and a composition was obtained that had excellent near-infrared absorption at a low concentration and very high transparency in the visible light region.

[0052] The dilution ratio of the composition of Example 1 was changed, and the compositions were prepared to the concentrations of Example 1-1 and Examples 1-3 to 1-6 in Table 1, and the transmittance was measured in the same manner as in Example 1-2. The results are shown in Table 1. As shown in Table 1, the transmittance generally decreases as the concentration of the composition increases. In Example 1-1, the concentration of the composition is low, and the transmittance of 800-1100 nm cannot be appropriately evaluated. Therefore, in Example 1, the transmittance was evaluated with a solid concentration of 5.1 g / L or more. As shown in Examples 1-2 to 1-6, the composition of Example 1 was shown to be a composition that has excellent near-infrared absorption over a wide concentration range and has very high transparency in the visible light region.

[0053] [Example 2 to Example 10] Compositions were prepared and transmittances were measured in the same manner as in Example 1, except that the types of Compound 1 and dispersant and their concentrations were changed as shown in Table 1.

[0054] [Table 1]

[0055] As in Example 2, the composition not containing the compound (1) had insufficient near-infrared absorbing performance, and it was not possible to achieve the desired transmittance characteristics even when the concentration was adjusted. As shown by a comparison of Examples 1, 3 to 5, and 7 to 8, it was shown that by increasing the ratio of compound (1) to copper ions, a composition having excellent near-infrared absorption performance can be obtained even at a lower concentration. As shown by the comparison of Examples 1, 9, and 10, it was shown that the use of a compound (1) having a lower molecular weight as the compound (1) results in a composition having excellent near-infrared absorption performance even at a low concentration. It was also shown that the use of a phosphoric acid diester as a dispersant allows the achievement of predetermined transmittance characteristics over a wide concentration range.

[0056] The present invention is not limited to the above-described embodiment, and can be modified as appropriate without departing from the spirit and scope of the present invention.

Claims

1. The present invention relates to a light absorbing agent comprising a compound represented by the following formula (1), a dispersant, a light absorbing agent formed by copper ions, and an organic solvent, A composition having at least one concentration of a solid content of 5 g / L or more and having a transmittance measured in a 1 cm cell that satisfies the following (I) and (II): (I) The maximum transmittance in the wavelength range of 800 nm to 1100 nm is 1% or less. (II) The minimum transmittance in the wavelength range of 400 nm to 600 nm is 80% or more. 【Chemistry 1】 In the formula (1), R 1 is an alkyl group having 1 to 4 carbon atoms or an oxyalkyl group having 1 to 4 carbon atoms.

2. The composition of claim 1 , wherein the organic solvent comprises a solvent having a dielectric constant less than 8.

3. A resin composition comprising the composition according to claim 1 or 2 and a resin.

4. The resin composition according to claim 3, having a viscosity at 25°C of 1,000 mPa·s or more.

5. An optical member comprising a cured product of the resin composition according to claim 3.

6. It is in the form of a film having a thickness of 130 μm or less, The maximum transmittance at wavelengths of 800 nm to 1100 nm is 1% or less; 6. The optical member according to claim 5, wherein the minimum value of the transmittance in the wavelength range of 400 nm to 600 nm is 80% or more.

7. A method for producing an optical member, comprising applying the resin composition according to claim 3 onto a substrate.

Citation Information

Patent Citations

  • Optical filter

    JP2020112826A