Masterbatch, resin composition using the same, and method for manufacturing molded articles

Abstract

The present invention provides: a resin composition which emits near-infrared fluorescence at a high luminescent efficiency and is relatively easy to produce; and a method for producing a molded object from the resin composition. Also provided are: a masterbatch with which the resin composition can be produced; and a method for producing the masterbatch. Specifically, the masterbatch comprises a near-infrared fluorescent material (A), a thermoplastic resin (B) which is not a polyamide resin, and a resin (C) different from the thermoplastic resin (B), wherein the resin (C) forms a continuous phase and a dispersed phase including the near-infrared fluorescent material (A) and the thermoplastic resin (B) has been formed in the continuous phase. The present invention further provides methods for producing the resin composition and the molded object, the methods each including a step for incorporating a diluent resin (D).

Description

[Technical Field]

[0001] The present invention relates to a masterbatch, a method for producing a resin composition using the masterbatch, and a method for producing a molded article obtained from the resin composition. More specifically, the invention relates to a resin composition that emits near-infrared fluorescence, has high luminescence efficiency, and is relatively easy to manufacture, a method for producing a molded article obtained from the resin composition, and a masterbatch capable of producing the resin composition and a method for producing the same. [Background technology]

[0002] Near-infrared fluorescent dyes are used in industrial products, primarily for product identification and anti-counterfeiting, and in recent years, they have also been used in medical applications such as bioimaging probes and diagnostic reagents. The characteristics of the near-infrared wavelength region include being invisible to the naked human eye, having minimal impact on living organisms, and high permeability to biological tissues such as skin. These characteristics can be utilized by incorporating near-infrared fluorescent dyes into medical devices themselves. For example, a system has been disclosed in which the position of a medical device implanted in the body can be confirmed by irradiating it with near-infrared light from outside the body, by incorporating near-infrared fluorescent dyes into medical devices such as shunt tubes (see, for example, Patent Document 1).

[0003] To visualize medical implants embedded subcutaneously, excitation with near-infrared light, which has high skin penetration, is necessary. Furthermore, the fluorescence emitted from the medical implant must also be in the near-infrared region, which also has high skin penetration. In other words, to ensure visibility, the near-infrared fluorescent dye contained in the medical implant must strongly absorb light in the near-infrared region and emit strong fluorescence. For this reason, it is preferable that the near-infrared fluorescent dye contained in the resin composition used as a raw material for medical implants has its maximum absorption wavelength in the near-infrared region within the resin.

[0004] Near-infrared fluorescent dyes include inorganic and organic fluorescent dyes. Generally, inorganic near-infrared fluorescent dyes have the advantage of being easy to adjust the emission wavelength within a desired range by using various metals, but they require rare earth elements such as rare earths and nanoparticles of uniform size, which are rare and expensive. On the other hand, organic near-infrared fluorescent dyes can be synthesized relatively easily and have features that make it easy to adjust the wavelength, but very few are known that can be stably mixed into resins.

[0005] If near-infrared fluorescent dyes can be mixed and dispersed in a resin, various molded articles that emit near-infrared fluorescence can be manufactured using the resin as a raw material. As an example of a resin in which near-infrared fluorescent dyes are dispersed, Patent Document 2 discloses a near-infrared fluorescent resin obtained by copolymerizing a reactive group-containing near-infrared fluorescent dye, which is a phthalocyanine dye, a naphthalocyanine dye, or a squalein dye into which a polyester reactive group has been introduced, in PET (polyethylene terephthalate).

[0006] On the other hand, boron complexes of π-conjugated compounds are known as organic fluorescent dyes with high emission quantum yields. For example, BODIPY dyes having a boron-dipyrrometene skeleton formed by a complex of a disubstituted boron atom and dipyrrometene (or its derivatives) are known (see, for example, Non-Patent Document 1). Furthermore, as BODIPY dyes that emit near-infrared fluorescence, Patent Document 3 discloses a BODIPY dye having a heterocycle in the BODIPY skeleton. In addition, Non-Patent Document 2 discloses a near-infrared fluorescent dye of a DPP-based boron complex having two boron complex units in the molecule, obtained by boron-complexing a diketopyrrolopyrrole (DPP) derivative. These BODIPY dyes and DPP-based boron complexes are mainly used as biomarkers to label biomolecules such as nucleic acids and proteins, and tumor tissues, and there are almost no reports on resins containing BODIPY dyes or DPP-based boron complexes. Regarding resin compositions containing BODIPY dyes, Patent Document 4 discloses that a resin emitting fluorescence in the visible light region was obtained by copolymerizing a siloxane-containing BODIPY dye, in which an organosiloxanil group is introduced via an alkylene group, into a silicone resin. Patent Document 5 also discloses a visible light-emitting composition in which the BODIPY dye is mixed with a solvent and polymer to improve its compatibility with visible light emission. Furthermore, Patent Document 6 discloses an optical filter containing a resin and BODIPY dyes having at least one electron-withdrawing group, which has high absorption of light in the visible light region, and Patent Document 7 discloses a color conversion material containing BODIPY dyes and resin that converts short-wavelength light to long-wavelength light.

[0007] In addition, Patent Document 8 lists DPP-based boron complexes as compounds that have absorption in the infrared region but not in the visible light region, and Patent Document 9 discloses an infrared absorbing composition containing the compound and a hydrophobic polymer. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] Japanese Patent Publication No. 2012-115535 [Patent Document 2] Japanese Patent Publication No. 2003-176289 [Patent Document 3] Patent No. 5177427 [Patent Document 4] Japanese Patent Publication No. 2013-060399 [Patent Document 5] U.S. Patent Application Publication No. 2013 / 0249137 [Patent Document 6] U.S. Patent Application Publication No. 2013 / 0252000 Specification [Patent Document 7] Japanese Patent Publication No. 2011-241160 [Patent Document 8] Patent No. 5380019 [Patent Document 9] Japanese Patent Publication No. 2010-090313 [Non-patent literature]

[0009] [Non-Patent Document 1] Tomimori, et al., Tetrahedron, 2011, Vol. 67, pp. 3187-3193. [Non-Patent Document 2] Fischer, et al., Angewandte Chemie International Edition, 2007, Vol. 46, pp. 3750-3753. [Overview of the project] [Problems that the invention aims to solve]

[0010] Although Patent Document 3 discloses BODIPY dyes that emit near-infrared fluorescence, it does not describe whether these can be incorporated into resins.

[0011] On the other hand, phthalocyanine dyes and the like have a low emission quantum yield of the pigment skeleton itself, so the reactive group-containing near-infrared fluorescent material described in Patent Document 2, which consists of these dyes, has the problem that it cannot obtain sufficient emission intensity.

[0012] Furthermore, while the siloxane-containing BODIPY dye described in Patent Document 4 has good compatibility with the silicone monomer solution before curing, and a uniformly dispersed silicone resin is obtained upon curing, it has the problem of poor compatibility with other resins and resin solutions. In addition, the resin composition described in Patent Document 5 has safety issues because the solvent may remain in the resin. Moreover, Patent Documents 4, 5, 6, and 7 do not describe BODIPY dyes that emit near-infrared fluorescence, nor do they describe their application to medical uses. Similarly, Patent Documents 8 and 9 do not describe DPP-based boron complexes that emit near-infrared light, nor do they report any application to medical uses.

[0013] Furthermore, fluorescent dyes that are directly covalently bonded to the polymer of a resin, such as those described in Patent Documents 2 and 4, are difficult to manufacture and have low versatility. In addition, introducing reactive groups into the dye complicates the synthesis route, leading to higher production costs and making it unsuitable for industrial mass production. Considering versatility, it is preferable to be able to produce a resin that emits near-infrared fluorescence simply by mixing and dispersing a near-infrared fluorescent dye in a resin. In particular, when dispersing in thermoplastic resins, a method of melt-kneading the resin and dye can be considered, but even when melt-kneading is performed at a temperature below the decomposition point of the dye, depending on the type of resin and dye and the kneading conditions, fluorescence may not be emitted due to reasons such as poor dispersion or decomposition of the dye. For example, it has been found that when kneaded with resins having amino groups such as polyamide resins or thermosetting resins, the dye may become inactive.

[0014] Thus, it is difficult to predict whether the above-mentioned dyes can be dispersed in thermoplastic resins, etc., based on the thermophysical properties of the dyes.

[0015] Therefore, an object of the present invention is to provide a resin composition that emits near-infrared fluorescence, has high luminous efficiency, and is relatively easy to manufacture, a method for manufacturing a molded body obtained from the resin composition, and further, to provide a masterbatch capable of manufacturing the resin composition and a method for manufacturing the same.

Means for Solving the Problems

[0016] The masterbatch according to the present invention, the resin composition using the same, and the method for manufacturing a molded body are as follows [1] to

[12] .

[0017] [1] Containing a near-infrared fluorescent material (A), a thermoplastic resin (B) other than a polyamide resin, and a resin (C) different from the thermoplastic resin (B), A masterbatch in which the resin (C) forms a continuous phase and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase.

[0018] [2] The near-infrared fluorescent material (A) is The following general formula (II1)

[0019]

Chemical formula

[0020] [ka] [In formula (II2), R a ~R f This is the same as formula (II1) above. ] Compounds represented by ] The following general formula (II3)

[0021] [ka] [In formula (II3), R h and R i R h The nitrogen atom and R that are bonded to it i Together with the bonded carbon atom, it forms an aromatic five-membered ring, an aromatic six-membered ring, or a condensed aromatic ring formed by the condensation of two or three five-membered or six-membered rings; R j and R k R j The nitrogen atom and R that are bonded to it kTogether with the bonded carbon atom, it forms an aromatic five-membered ring, an aromatic six-membered ring, or a condensed aromatic ring formed by the condensation of two or three five-membered or six-membered rings; R l , R m , R n , and R o These are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, aryl group, or heteroaryl group; R p and R q These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, aryl group, or heteroaryl group; R r and R s These represent, independently of each other, a hydrogen atom or an electron-withdrawing group. ] Compounds represented by ] Furthermore, the following general formula (II4)

[0022] [ka] [In formula (II4), R h ~R q This is the same as formula (II3) above. It is at least one compound selected from the group consisting of compounds represented by ] A masterbatch as described in [1], wherein the maximum fluorescence wavelength is 650 nm or greater.

[0023] [3] The near-infrared fluorescent material (A) is The following general formulas (II3-1) to (II3-6)

[0024] [ka] [In formula (II3-1), R 23 , R 24 , R 25 , and R 26 These are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C1-20 Represents an alkoxy group, aryl group, or heteroaryl group; R 27 and R 28 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, aryl group, or heteroaryl group; R 29 and R 30 These independently represent a hydrogen atom or an electron-withdrawing group; Y 9 and Y 10 These represent, independently of each other, a sulfur atom, an oxygen atom, a nitrogen atom, or a phosphorus atom; R 31 and R 32 teeth, (p4) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group, (p5)R 31 and R 32 Both form an optionally substituted aromatic five-membered ring or an optionally substituted aromatic six-membered ring; R 33 and R 34 teeth, (q4) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group, (q5)R 33 and R 34 Both form an aromatic five-membered ring or an aromatic six-membered ring, which may have substituents.

[0025] [ka] [In formulas (II3-2) to (II3-6), R 23 ~R 30 This is the same as equation (II3-1) above; X 1and X 2 each independently represents a nitrogen atom or a phosphorus atom; R 35 R 36 R 37 and R 38 are (p6) each independently represents a hydrogen atom, a halogen atom, a C 1-20 alkyl group, a C 1-20 alkoxy group, an aryl group, or a heteroaryl group, (p7) R 35 and R 36 together form an optionally substituted aromatic 5-membered ring or an optionally substituted aromatic 6-membered ring, and R 37 and R 38 each independently represents a hydrogen atom, a halogen atom, a C 1-20 alkyl group, a C 1-20 alkoxy group, an aryl group, or a heteroaryl group, (p8) R 36 and R 37 together form an optionally substituted aromatic 5-membered ring or an optionally substituted aromatic 6-membered ring, and R 35 and R 38 each independently represents a hydrogen atom, a halogen atom, a C 1-20 alkyl group, a C 1-20 alkoxy group, an aryl group, or a heteroaryl group, or (p9) R 37 and R 38 together form an optionally substituted aromatic 5-membered ring or an optionally substituted aromatic 6-membered ring, and R 35 and R 36 each independently represents a hydrogen atom, a halogen atom, a C 1-20 alkyl group, a C 1-20 alkoxy group, an aryl group, or a heteroaryl group; R 39 R 40 R 41 and R 42 are (q6) each independently represents a hydrogen atom, a halogen atom, a C 1-20 alkyl group, a C 1-20Represents an alkoxy group, an aryl group, or a heteroaryl group. (q7)R 39 and R 40 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 41 and R 42 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group. (q8)R 40 and R 41 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 39 and R 42 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group, (q9)R 41 and R 42 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 39 and R 40 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 Compounds represented by any of the following general formulas (II4-1) to (II4-6): [represents an alkoxy group, an aryl group, or a heteroaryl group]

[0026] [ka] [In equations (II4-1) to (II4-6), R 23 ~R 28 This is the same as equation (II3-1) above. In equation (II4-1), R 31 ~R 34 , Y 9 , and Y 10 This is the same as equation (II3-1) above, and in equations (II4-2) to (II4-6), R 35 ~R 42This is the same as equation (II3-2) above, and in equations (II4-3) to (II4-6), X 1 , and X 2 The masterbatch according to [2] contains at least one compound selected from the group consisting of compounds represented by any of the following formulas (II3-3).

[0027] [4] The near-infrared fluorescent material (A) is The following general formulas (II3-7) to (II3-9) and (II4-7) to (II4-9)

[0028] [ka] [In the formula, Y 23 and Y 24 These represent, independently of each other, a carbon atom or a nitrogen atom; Y 13 and Y 14 These represent, independently of each other, an oxygen atom or a sulfur atom; Y 25 and Y 26 These represent, independently of each other, a carbon atom or a nitrogen atom; R 47 and R 48 These represent, independently of each other, a hydrogen atom or an electron-withdrawing group; R 43 , R 44 , R 45 , and R 46 Each represents independently of the other an aryl group which may have a halogen atom or substituent; P 15 and P 16 These are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 This represents alkoxy groups, amino groups, monoalkylamino groups, and dialkylamino groups; n15 and n16 represent integers between 0 and 3, independently of each other; A 15 and A 16 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C1-20 This represents a phenyl group which may have 1 to 3 substituents selected from the group consisting of alkoxy groups, amino groups, monoalkylamino groups, and dialkylamino groups. The masterbatch according to [3], comprising at least one compound selected from the group consisting of compounds represented by any of the following.

[0029] [5] The masterbatch according to any one of [1] to [4], wherein the content of the near-infrared fluorescent material (A) relative to 100% by mass of the total of the near-infrared fluorescent material (A) and the thermoplastic resin (B) other than the polyamide resin is 0.001% by mass or more and 0.5% by mass or less.

[0030] [6] The masterbatch according to any one of [1] to [5], wherein the thermoplastic resin (B) other than the polyamide resin comprises at least one selected from the group consisting of thermoplastic polyurethane (TPU) resin, polycarbonate (PC) resin, vinyl chloride resin, acrylic resin, polyester resin, polystyrene resin, olefin resin, and polyacetal (POM) resin.

[0031] [7] The masterbatch according to any one of [1] to [6], wherein the resin (C) comprises at least one selected from the group consisting of polyamide resins, polyethylene resins, polypropylene resins, and thermosetting resins.

[0032] [8] The masterbatch according to [7], wherein the resin (C) comprises a polyamide resin.

[0033] [9] The masterbatch according to [7], wherein the resin (C) comprises a thermosetting resin.

[0034]

[10] The masterbatch according to any one of [1] to [9], wherein the total content of the near-infrared fluorescent material (A) and the thermoplastic resin (B) is in the range of 20% by mass or more and 80% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), the thermoplastic resin (B), and the resin (C).

[0035]

[11] A process comprising the steps of: melt-kneading a near-infrared fluorescent material (A) and a thermoplastic resin other than a polyamide resin (B) to obtain a compound; pulverizing the compound obtained in the first step to obtain particles containing powdered near-infrared fluorescent material (A) and thermoplastic resin (B); and mixing or kneading the particles obtained in the first step with a resin (C). A method for producing a masterbatch in which the resin (C) forms a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase.

[0036]

[12] A step of adding a diluent resin (D) to a masterbatch described in any of [1] to

[10] and mixing or kneading it, The material comprises a near-infrared fluorescent material (A), a thermoplastic resin other than a polyamide resin (B), a resin different from the thermoplastic resin (B) (C), and a resin different from the thermoplastic resin (B) (D). A method for producing a resin composition, wherein the resins (C) and (D) form a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase.

[0037]

[13] The method for producing the resin composition according to

[12] , wherein the resin (C) and the resin (D) are selected from the group consisting of polyamide resins, polyethylene resins, polypropylene resins, thermosetting resins, and crosslinked polyethylene resins.

[0038]

[14] A method for producing a resin composition according to

[12] or

[13] , wherein the content of the resin (D) is in the range of 20% by mass or more and 80% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), the thermoplastic resin (B), the resin (C), and the resin (D).

[0039]

[15] A method for producing the resin composition according to any one of

[12] to

[14] , wherein the resin composition is used as a medical material.

[0040]

[16] A method for producing a resin composition according to any one of

[12] to

[15] , wherein at least a portion of the resin composition is used as a material for a medical device used in the body of a patient.

[0041] A method for producing a molded article, comprising the step of melt-molding a resin composition obtained by any of the manufacturing methods described in

[17]

[12] to

[16] . [Effects of the Invention]

[0042] According to the present invention, it is possible to provide a resin composition that emits near-infrared fluorescence, has high luminescence efficiency, and is relatively easy to manufacture, as well as a method for manufacturing a molded article obtained from the resin composition, and furthermore, a masterbatch capable of producing the resin composition and a method for manufacturing the same. [Brief explanation of the drawing]

[0043] [Figure 1] This is a schematic diagram of the apparatus used to measure luminous efficiency. [Modes for carrying out the invention]

[0044] The present invention relates to a masterbatch comprising a near-infrared fluorescent material (A), a thermoplastic resin other than a polyamide resin (B) (hereinafter also simply referred to as thermoplastic resin (B)), and a resin (C) different from the thermoplastic resin (B), wherein the resin (C) forms a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase.

[0045] The masterbatch of the present invention having such a configuration can suppress the deactivation of the near-infrared fluorescent material (A), and provides a resin composition that has the excellent effects of high near-infrared fluorescence luminescence efficiency and relatively easy manufacturing. Furthermore, a molded article obtained from the resin composition manufactured via the masterbatch also has the excellent effects of high near-infrared fluorescence luminescence efficiency and relatively easy manufacturing.

[0046] Furthermore, in the masterbatch of the present invention, it can be confirmed using a digital microscope or the like that the near-infrared fluorescent material (A) and thermoplastic resin (B) form a dispersed phase (the so-called island portion of a sea-island structure), and the resin (C) forms a continuous phase (the so-called sea portion of a sea-island structure).

[0047] Preferred embodiments of the present invention will be described below. In this specification, "X~Y" indicating a range means "X or more and Y or less". Unless otherwise specified in this specification, operations and measurements of physical properties, etc., will be performed under room temperature (20~25°C) / relative humidity of 40~50%RH.

[0048] [Masterbatch Configuration] <Near-infrared fluorescent material (A)> The near-infrared fluorescent material (A) used in the present invention is a compound whose fluorescence maximum wavelength is in the near-infrared region. When the resin composition produced via the masterbatch according to the present invention is used, for example, as a material for medical devices or security devices used in living organisms, the resin composition containing the above-mentioned near-infrared fluorescent material (A) and the molded articles obtained therefrom can be excited and detected by light in the invisible near-infrared region, so that the excitation light and fluorescence can be detected without changing the color tone of biological tissues, etc.

[0049] Examples of near-infrared fluorescent materials (A) include, for example, compounds such as polymethine dyes, anthraquinone dyes, dithiol metal salt dyes, cyanine dyes, phthalocyanine dyes, indophenol dyes, cyamine dyes, styryl dyes, aluminum dyes, diimonium dyes, azo dyes, azo-boron dyes, boron dipyrmethene (BODIPY) dyes described in International Publication No. 2007 / 126052, diketopyrrolopyrrole (DPP) boron complexes, squarium dyes, and perylene dyes. These near-infrared fluorescent materials (A) can be used individually or in mixtures of two or more.

[0050] Among the materials described above, cyanine dyes, azo-boron dyes, borondipyrmethene (BODIPY) dyes, diketopyrrolopyrrole (DPP) boron complexes, phthalocyanine dyes, or squarium dyes are preferred as the near-infrared fluorescent material (A) used in the present invention from the viewpoint of luminescence efficiency, and in particular, BODIPY dyes represented by the following general formula (II1) or general formula (II2), or DPP boron complexes represented by the following general formula (II3) or general formula (II4) are preferred from the viewpoint of heat resistance. This is because if the luminescence efficiency is low, sufficient luminescence intensity may not be obtained, and if the heat resistance is low, the material may decompose when kneaded with the resin.

[0051] <Compounds represented by general formula (II1), general formula (II2), general formula (II3), or general formula (II4)> The near-infrared fluorescent material (A) used in the present invention is preferably a compound represented by the following general formula (II1) or general formula (II2). These compounds may hereinafter be referred to as "BODIPY dyes used in the present invention."

[0052] [ka] Compounds represented by the following general formula (II3) or general formula (II4) are also preferred as near-infrared fluorescent materials used in the present invention. These compounds may hereafter be referred to as "DPP-based boron complexes used in the present invention."

[0053] [ka]

[0054] In general formula (II1) or general formula (II2), R a and R b R a The nitrogen atom and R that are bonded to it b It forms an aromatic ring consisting of 1 to 3 rings together with the carbon atom to which it is bonded. Similarly, in general formula (II1) or general formula (II2), R c and Rd R c The nitrogen atom and R that are bonded to it d It forms an aromatic ring consisting of 1 to 3 rings together with the carbon atom to which it is bonded. a and R b The aromatic ring formed by, and R c and R d Each ring in the aromatic ring formed is either a 5-membered or 6-membered ring. Compounds represented by general formula (II1) or general formula (II2) are R a and R b The aromatic ring and R that are formed c and R d The aromatic ring formed by this compound has a fused ring structure in which a ring containing a boron atom bonded to two nitrogen atoms is attached. In other words, compounds represented by general formula (II1) or general formula (II2) have a robust fused ring structure consisting of a broad conjugated plane.

[0055] In general formula (II3) or general formula (II4), R h and R i R h The nitrogen atom and R that are bonded to it i It forms an aromatic ring consisting of 1 to 3 rings together with the carbon atom to which it is bonded. Similarly, in general formula (II3) or general formula (II4), R j and R k R j The nitrogen atom and R that are bonded to it k It forms an aromatic ring consisting of 1 to 3 rings together with the carbon atom to which it is bonded. h and R i The aromatic ring formed by, and R j and R k Each ring in the aromatic ring formed is either a 5-membered or 6-membered ring. Compounds represented by general formula (II3) or general formula (II4) are R h and R i A triring is formed by the condensation of an aromatic ring, a ring containing a boron atom bonded to two nitrogen atoms, and a five-membered heteroring containing one nitrogen atom, and R j and R kThe compound has a ring structure in which at least six rings are fused together, i.e., a ring structure in which an aromatic ring formed by the compound is fused with a ring containing a boron atom bonded to two nitrogen atoms and a five-membered heteroring containing one nitrogen atom, and these three rings are fused together with the five-membered heterorings. Thus, the compound represented by general formula (II3) or general formula (II4) has a robust fused ring structure consisting of a very broad conjugated plane.

[0056] R a and R b The aromatic ring formed by, R c and R d The aromatic ring formed by, R h and R i The aromatic ring formed by, and R j and R k The aromatic ring formed is not particularly limited as long as it has an aromatic property. Examples of such aromatic rings include pyrrole rings, imidazole rings, pyrazole rings, oxazole rings, thiazole rings, pyridine rings, pyrimidine rings, pyridazine rings, isoindole rings, indole rings, indazole rings, purine rings, perimidine rings, thienopyrrole rings, phlopyrrole rings, pyrrolothiazole rings, and pyrrolooxazole rings. Since the maximum fluorescence wavelength is extended to the near-infrared region, in particular, in the case of general formula (II1) or general formula (II3), the aromatic ring preferably has 2 or 3 ring fusions, and more preferably 2 from the standpoint of complexity in synthesis. However, even when the aromatic ring has 1 ring fusion, it is possible to extend the wavelength by devising substituents on the ring or on the boron. Furthermore, in particular, with general formula (II2) or general formula (II4), the wavelength can be extended to the near-infrared region simply by attaching a substituted aryl group or heteroaryl group.

[0057] R a and R b The aromatic ring formed by, R c and R d The aromatic ring formed by, R h and R i The aromatic ring formed by, and R j and R kThe aromatic ring formed may be unsubstituted, or it may have one or more substituents. The substituents on the aromatic ring may be "any group that does not inhibit the fluorescence of the compound."

[0058] When the resin composition according to the present invention is used as a medical material (raw material for medical devices), the near-infrared fluorescent material to be included is preferably one that tests negative for mutagenicity, cytotoxicity, sensitization, and skin irritation in necessary biological safety tests. Furthermore, from the viewpoint of safety, it is preferable that the near-infrared fluorescent material does not leach out of the molded article obtained by processing the resin composition according to the present invention by bodily fluids such as blood and tissue fluid. For this reason, it is preferable that the near-infrared fluorescent material used in the present invention has low solubility in biological components such as blood. However, even if the near-infrared fluorescent material used in the present invention is water-soluble, if the resin component in the resin composition according to the present invention hardly leaches out of bodily fluids, and the amount of the near-infrared fluorescent material itself is trace, then the molded article of the resin composition according to the present invention can be used in vivo while avoiding the leaching of the near-infrared fluorescent material. Considering these factors, in the BODIPY dye used in the present invention, R a and R b The aromatic ring or R formed by c and R d It is preferable to select substituents that are less likely to exhibit mutagenicity or reduce water solubility as substituents on the aromatic ring formed by the compound. Similarly, in the DPP boron complex used in the present invention, R h and R i The aromatic ring or R formed by j and R k It is preferable to select substituents that are less likely to exhibit mutagenicity or other harmful effects, or that reduce water solubility, for the aromatic ring formed by the compound.

[0059] Examples of such substituents include halogen atoms, nitro groups, cyano groups, hydroxyl groups, carboxyl groups, aldehyde groups, sulfonic acid groups, alkylsulfonyl groups, halogenosulfonyl groups, thiol groups, alkylthio groups, isocyanate groups, thioisocyanate groups, alkyl groups, alkenyl groups, alkynyl groups, alkoxy groups, alkoxycarbonyl groups, alkylamidecarbonyl groups, alkylcarbonylamide groups, acyl groups, amino groups, monoalkylamino groups, dialkylamino groups, silyl groups, monoalkylsilyl groups, dialkylsilyl groups, trialkylsilyl groups, monoalkoxysilyl groups, dialkoxysilyl groups, trialkoxysilyl groups, aryl groups, and heteroaryl groups. a and R b The aromatic ring formed by, R c and R d The aromatic ring formed by, R h and R i The aromatic ring formed by, or R j and R k The substituents on the aromatic ring formed are preferably cyano groups, hydroxyl groups, carboxyl groups, alkylthio groups, alkyl groups, alkoxy groups, alkoxycarbonyl groups, amide groups, alkylsulfonyl groups, fluorine, chlorine, aryl groups, or heteroaryl groups, from the viewpoint of safety for living organisms, and these substituents may have further substituents. However, safety can be improved by introducing other substituents as well, so the material is not limited to these substituents.

[0060] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, with fluorine atoms, chlorine atoms, and bromine atoms being preferred, and fluorine atoms being more preferred.

[0061] Alkyl groups, alkenyl groups, and alkynyl groups may be linear, branched, or cyclic (aliphatic ring groups). The number of carbon atoms in these groups is preferably 1 to 20, more preferably 1 to 12, even more preferably 1 to 8, and particularly preferably 1 to 6. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl (tert-butyl), pentyl, isoamyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, and dodecyl groups. Examples of alkenyl groups include vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, and 2-hexenyl groups. Examples of alkynyl groups include ethynyl group, 1-propynyl group, 2-propynyl group, isopropynyl group, 1-butynyl group, and isobutynyl group.

[0062] Examples of alkyl groups include alkylsulfonyl groups, alkylthio groups, alkoxy groups, alkoxycarbonyl groups, alkylamidecarbonyl groups, alkylcarbonylamide groups, monoalkylamino groups, dialkylamino groups, monoalkylsilyl groups, dialkylsilyl groups, trialkylsilyl groups, monoalkoxysilyl groups, dialkoxysilyl groups, and trialkoxysilyl groups. The alkyl group portion of these groups is the same as that of the alkyl groups mentioned above. For example, examples of alkoxy groups include methoxy groups, ethoxy groups, propyloxy groups, isopropyloxy groups, n-butyloxy groups, isobutyloxy groups, t-butyloxy groups, pentyloxy groups, isoamyloxy groups, hexyloxy groups, heptyloxy groups, octyloxy groups, nonyloxy groups, decyloxy groups, undecyloxy groups, and dodecyloxy groups. Furthermore, examples of monoalkylamino groups include methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, t-butylamino group, pentylamino group, hexylamino group, etc., and examples of dialkylamino groups include dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, diisobutylamino group, dipentylamino group, dihexylamino group, ethylmethylamino group, methylpropylamino group, butylmethylamino group, ethylpropylamino group, butylethylamino group, etc.

[0063] Examples of aryl groups include phenyl, naphthyl, indenyl, and biphenyl groups. Phenyl groups are preferred.

[0064] Examples of heteroaryl groups include five-membered ring heteroaryl groups such as pyrrolyl, imidazolyl, pyrazolyl, thienyl, furanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, and thiadiazole groups; six-membered ring heteroaryl groups such as pyridinyl, pyrazinyl, pyrimidinyl, and pyridadinyl groups; and condensed heteroaryl groups such as indolyl, isoindolyl, indazolyl, quinolidinyl, quinolinyl, isoquinolinyl, benzofuranyl, isobenzofuranyl, clomenyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, and benzoisothiazolyl groups.

[0065] Alkyl groups, alkenyl groups, alkynyl groups, aryl groups, and heteroaryl groups may be unsubstituted or may have one or more hydrogen atoms substituted by substituents. Examples of substituents include halogen atoms, alkyl groups, alkoxy groups, nitro groups, cyano groups, hydroxyl groups, amino groups, thiol groups, carboxyl groups, aldehyde groups, sulfonic acid groups, isocyanate groups, thioisocyanate groups, aryl groups, and heteroaryl groups.

[0066] The absorption and fluorescence wavelengths of fluorescent materials depend on the surrounding environment. Therefore, the absorption wavelength of a fluorescent material in a resin may be shorter or longer compared to when it is in solution. When the absorption wavelength of the material itself is longer, such as with BODIPY dyes and DPP-based boron complexes used in this invention, it is preferable because the maximum absorption wavelength will be in the near-infrared region even in various resins. The maximum absorption wavelength of a fluorescent material can be made longer by introducing electron-donating groups and electron-withdrawing groups at appropriate positions within the molecule, thereby narrowing the band gap between the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO).

[0067] For example, among the compounds represented by general formula (II1), R a and R b The aromatic ring formed by, and R c and R dAn electron-donating group is introduced into the aromatic ring formed by R g By introducing an electron-withdrawing group, the maximum absorption wavelength and maximum fluorescence wavelength of the compound can be made longer. Similarly, among the compounds represented by general formula (II3), R h and R i The aromatic ring formed by, and R j and R k Introducing an electron-donating group into the aromatic ring formed by R p and R q If it has an aromatic ring, an electron-donating group is introduced to the aromatic ring, or R r and R s By introducing electron-withdrawing groups, the maximum absorption and fluorescence wavelengths of the compound can be extended to longer wavelengths. By combining these designs, it is possible to adjust the wavelength to the desired value.

[0068] Compounds represented by general formula (II2) having an aza-BODIPY skeleton are R a and R b The aromatic ring formed by, and R c and R d The aromatic ring formed by this has a skeleton that absorbs at relatively long wavelengths even when unsubstituted. Unlike the compound represented by general formula (II1), in this skeleton, the bridging portion of the pyrrole is a nitrogen atom, so substituents cannot be introduced on the nitrogen, but the pyrrole portion (R a and R b The aromatic ring formed by, and R c and R d By introducing an electron-donating group to the aromatic ring formed by the compound, the maximum absorption wavelength and maximum fluorescence wavelength of the compound can be made longer. Similarly, in the case of a compound represented by general formula (II4), the pyrrole moiety (R h and R i The aromatic ring formed by, and R j and R k Introducing an electron-donating group to the aromatic ring formed by, or R p and R qIf the compound has an aromatic ring, the maximum absorption wavelength and maximum fluorescence wavelength of the compound can be made longer by introducing an electron-donating group to the aromatic ring.

[0069] Therefore, R a and R b The aromatic ring formed by, R c and R d The aromatic ring formed by, R h and R i The aromatic ring formed by, and R j and R k The substituents on the aromatic ring formed are preferably groups that function as electron-donating groups for the aromatic ring, among "any group that does not inhibit the fluorescence of the compound". By introducing an electron-donating group to the aromatic ring, the fluorescence of the compound represented by general formula (II1), general formula (II2), general formula (II3), or general formula (II4) is shifted to longer wavelengths. Examples of groups that function as electron-donating groups include alkyl groups; alkoxy groups such as methoxy groups; aryl groups (aromatic ring groups) such as phenyl groups, p-alkoxyphenyl groups, p-dialkylaminophenyl groups, and dialkoxyphenyl groups; and heteroaryl groups (heteroaromatic ring groups) such as 2-thienyl groups and 2-furanyl groups. For alkyl groups, alkyl groups in substituents of phenyl groups, and alkyl groups in alkoxy groups, linear or branched alkyl groups having 1 to 10 carbon atoms are preferred. The number of carbon atoms and whether or not the alkyl group is branched may be appropriately selected in consideration of the various properties of the fluorescent material. From the viewpoint of solubility and compatibility, it is sometimes preferable to have 6 or more carbon atoms, or that the element is branched. a and R b The aromatic ring formed by, R c and R d The aromatic ring formed by, R h and R i The aromatic ring formed by, and R j and R k The substituents on the aromatic ring formed by are C 1-6 Alkyl alkyl group, C 1-6An alkoxy group, aryl group, or heteroaryl group is preferred, a methyl group, ethyl group, methoxy group, phenyl group, p-methoxyphenyl group, p-ethoxyphenyl group, p-dimethylaminophenyl group, dimethoxyphenyl group, thienyl group, or furanyl group is more preferred, and a methyl group, ethyl group, methoxy group, phenyl group, or p-methoxyphenyl group is even more preferred. Because the BODIPY skeleton and DPP skeleton have high planarity, molecules tend to aggregate with each other by π-π stacking. By introducing an aryl group or heteroaryl group with a bulky substituent into the BODIPY skeleton or DPP skeleton, molecular aggregation can be suppressed, and the luminescence quantum yield of the resin composition and its molded articles according to the present invention can be increased.

[0070] In general formula (II1) or general formula (II2), R a and R b The aromatic ring formed by and R c and R d The aromatic ring formed by may be different from or the same as the one formed by R. In general formula (II3) or general formula (II4), h and R i The aromatic ring formed by and R j and R k The aromatic ring formed may be different from or the same as the one formed. The BODIPY dye or DPP boron complex used in the present invention is easy to synthesize and tends to have a higher luminescence quantum yield, so R a and R b The aromatic ring and R that are formed c and R d The aromatic ring formed by, or R h and R i The aromatic ring and R that are formed j and R k The aromatic ring formed is preferably of the same type.

[0071] In general formula (II1) or general formula (II2), R e and R f These represent, independently of each other, a halogen atom or an oxygen atom. e and Rf When the atom is a halogen atom, fluorine, chlorine, bromine, or iodine atoms are preferred, fluorine or chlorine atoms are more preferred, and fluorine atoms are particularly preferred because they have a strong bond with boron atoms. e and R f Compounds containing fluorine atoms have high heat resistance, making them advantageous when melt-mixed with resins at high temperatures. Note that compounds represented by general formula (II1) or general formula (II2) include R e and R f Even if the substituent is not a halogen atom or an oxygen atom, but contains an atom that can bond with a boron atom, it can be included in the resin in the same way as the BODIPY dye used in the present invention. Such substituents are acceptable as long as they do not inhibit fluorescence.

[0072] In general formula (II1) or general formula (II2), R e and R f If R is an oxygen atom, e , R e The boron atom that bonds with R a , and R a The nitrogen atoms to which it is bonded may together form a ring, R f , R f The boron atom that bonds with R c , and R c The nitrogen atoms to which it is bonded may together form a ring. In other words, when a ring structure is formed, R e , R e The boron atom that bonds with R a The ring formed by the nitrogen atom to which it is bonded is R a and R b It condenses with the aromatic ring formed by R f , R f The boron atom that bonds with R c The ring formed by the nitrogen atom to which it is bonded is R c and R d It condenses with the aromatic ring that it forms. e The ring and R formed by the etc. f The ring formed by these is preferably a 6-membered ring.

[0073] In general formula (II1) or general formula (II2), R e This is the case when R is an oxygen atom. e If they do not form a ring, R e C is an oxygen atom having a substituent (an oxygen atom bonded to a substituent). The substituent may be C 1-20 Examples include alkyl groups, aryl groups, heteroaryl groups, alkylcarbonyl groups, arylcarbonyl groups, or heteroarylcarbonyl groups. Similarly, in general formula (II1) or general formula (II2), R f This is the case when R is an oxygen atom. f If they do not form a ring, R f C is an oxygen atom having a substituent (an oxygen atom bonded to a substituent). The substituent may be C 1-20 Examples include alkyl groups, aryl groups, heteroaryl groups, alkylcarbonyl groups, arylcarbonyl groups, or heteroarylcarbonyl groups. e and R f If both are oxygen atoms with substituents, R e The substituents and R f The substituents that it possesses may be of the same type or different types.

[0074] In general formula (II1) or general formula (II2), R e and R f If R is an oxygen atom, e , R f , and R e and R f The boron atoms bonded to it may together form a ring. For example, the ring structure may be R e and R f Structures in which the same aryl ring or heteroaryl ring is linked, R e and R f Examples include structures in which these groups are linked by alkylene groups.

[0075] In general formula (II3) or general formula (II4), R l , R m , R n , and R oThese are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 R represents an alkoxy group, an aryl group, or a heteroaryl group. l , R m , R n , or R o When the atom is a halogen atom, fluorine, chlorine, bromine, or iodine atoms are preferred, fluorine or chlorine atoms are more preferred, and fluorine atoms are particularly preferred because they have a strong bond with boron atoms. l , R m , R n , and R o However, compounds containing fluorine atoms have high heat resistance, which is advantageous when melt-mixing them with resins at high temperatures.

[0076] Furthermore, in the present invention and the present specification, "C 1-20 "Alkyl alkyl" refers to an alkyl group with 1 to 20 carbon atoms, and "C 1-20 The term "alkoxy group" refers to an alkoxy group having 1 to 20 carbon atoms.

[0077] R l , R m , R n , or R o C 1-20 In the case of alkyl groups, the alkyl group may be linear, branched, or cyclic (aliphatic ring group). Examples of such alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, t-butyl group, pentyl group, isoamyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, and the like.

[0078] R l , R m , R n , or R o C 1-20In the case of an alkoxy group, the alkyl group portion of the alkoxy group may be linear, branched, or cyclic (aliphatic ring group). Examples of such alkoxy groups include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, t-butyloxy group, pentyloxy group, isoamyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, undecyloxy group, and dodecyloxy group.

[0079] R l , R m , R n , or R o If the group is an aryl group, examples of such aryl groups include phenyl, naphthyl, indenyl, and biphenyl groups.

[0080] R l , R m , R n , or R o When the group is a heteroaryl group, examples of such heteroaryl groups include five-membered ring heteroaryl groups such as pyrrolyl, imidazolyl, pyrazolyl, thienyl, furanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, and thiadiazole groups; six-membered ring heteroaryl groups such as pyridinyl, pyrazinyl, pyrimidinyl, and pyridadinyl groups; and condensed heteroaryl groups such as indolyl, isoindolyl, indazolyl, quinolidinyl, quinolinyl, isoquinolinyl, benzofuranyl, isobenzofuranyl, clomenyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, and benzoisothiazolyl groups.

[0081] R l , R m , R n , or R o C represented by 1-20 Alkyl alkyl group, C 1-20Alkoxy groups, aryl groups, and heteroaryl groups may be unsubstituted or may have one or more hydrogen atoms substituted by substituents. Examples of substituents include halogen atoms, alkyl groups, alkoxy groups, nitro groups, cyano groups, hydroxyl groups, amino groups, thiol groups, carboxyl groups, aldehyde groups, sulfonic acid groups, isocyanate groups, thioisocyanate groups, aryl groups, and heteroaryl groups.

[0082] Compounds represented by general formula (II3) or general formula (II4) include R l , R m , R n , and R o Preferably, the element is a halogen atom, an unsubstituted aryl group, or a substituted aryl group, and may be a fluorine atom, a chlorine atom, a bromine atom, an unsubstituted phenyl group, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group is preferred, and may be a fluorine atom, a chlorine atom, an unsubstituted phenyl group, or C 1-10 Alkyl or C 1-10 Phenyl groups substituted with alkoxy groups are more preferred, and fluorine atoms or unsubstituted phenyl groups are particularly preferred.

[0083] In general formula (II3) or general formula (II4), R p and R q These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 R represents an alkoxy group, an aryl group, or a heteroaryl group. p and R q The halogen atom represented by C 1-20 Alkyl alkyl group, C 1-20 As for the alkoxy group, aryl group, and heteroaryl group, R of the general formula (II3) is... l , R m , R n , or R o Similar examples include the above.

[0084] Compounds represented by general formula (II3) or general formula (II4) include Rp and R q Preferably, it is a hydrogen atom or an aryl group, a hydrogen atom, an unsubstituted phenyl group, or C 1-20 Alkyl or C 1-20 Preferably, the phenyl group is substituted with an alkoxy group, and may be a hydrogen atom, an unsubstituted phenyl group, or C 1-20 A phenyl group substituted with an alkoxy group is more preferable, and may be a hydrogen atom, an unsubstituted phenyl group, or C 1-10 Phenyl groups substituted with alkoxy groups are particularly preferred.

[0085] In general formula (II1), R g R represents a hydrogen atom or an electron-withdrawing group. Also, in general formula (II3), R r and R s These groups independently represent a hydrogen atom or an electron-withdrawing group. Examples of such electron-withdrawing groups include methyl halides such as trifluoromethyl groups; nitro groups; cyano groups; aryl groups; heteroaryl groups; alkynyl groups; alkenyl groups; substituents having a carbonyl group such as carboxyl groups, acyl groups, carbonyloxy groups, amide groups, and aldehyde groups; sulfoxide groups; sulfonyl groups; alkoxymethyl groups; and aminomethyl groups. Aryl groups and heteroaryl groups having these electron-withdrawing groups as substituents can also be used. Among these electron-withdrawing groups, trifluoromethyl groups, nitro groups, cyano groups, and sulfonyl groups are preferred because they can function as strong electron-withdrawing groups in terms of extending the maximum fluorescence wavelength.

[0086] In the present invention, compounds represented by the following general formula (II1-0) or general formula (II2-0) are preferred as BODIPY dyes. Compounds having a borondipyrromethene skeleton are preferred because their maximum fluorescence wavelength is longer, and in particular, compounds in which a pyrrole ring is fused with an aromatic ring or a heteroaromatic ring, satisfying the following (p2), (p3), (q2), or (q3), are preferred as near-infrared fluorescent materials used in the present invention because their maximum fluorescence wavelength is even longer.

[0087] [ka] In general formula (II1-0) or general formula (II2-0), R 101 , R 102 , and R 103 It satisfies one of the following conditions (p1) to (p3): (p1) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group. (p2)R 101 and R 102 Both form an aromatic 5-membered ring or an aromatic 6-membered ring, R 103 is a hydrogen atom, halogen atom, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group, (p3)R 102 and R 103 Both form an aromatic 5-membered ring or an aromatic 6-membered ring, R 101 is a hydrogen atom, halogen atom, C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. In general formula (II1-0) or general formula (II2-0), R 104 , R 105 , and R 106 The following conditions (q1) to (q3) must be met: (q1) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group. (q2)R 104 and R 105 Both form an aromatic 5-membered ring or an aromatic 6-membered ring, R 106 is a hydrogen atom, halogen atom, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group, (q3)R 105 and R 106Both form an aromatic 5-membered ring or an aromatic 6-membered ring, R 104 is a hydrogen atom, halogen atom, C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. The halogen atoms in (p1)~(p3) or (q1)~(q3) above, C 1-20 Alkyl alkyl group, C 1-20 As for the alkoxy group, aryl group, and heteroaryl group, R is the correct term, respectively. a and R b Any group exemplified as "any group that does not inhibit the fluorescence of the compound" can be used. In the above (p2)~(p3) or (q2)~(q3), R 101 and R 102 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 104 and R 105 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 102 and R 103 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 105 and R 106 The aromatic five-membered ring or aromatic six-membered ring formed by these is preferably represented by any of the following general formulas (C-1) to (C-9), and more preferably by any of the following general formulas (C-1), (C-2), or (C-9). In the following general formulas (C-1) to (C-9), the parts marked with an asterisk are the parts that bond with the borondipyrromethene skeleton in general formula (II1-0) or general formula (II2-0).

[0088] [ka]

[0089] In the general formulas (C-1) to (C-8), Y 1 ~Y 8 These elements independently represent a sulfur atom, an oxygen atom, a nitrogen atom, or a phosphorus atom. 1 ~Y 8Preferably, these atoms are sulfur atoms, oxygen atoms, or nitrogen atoms, independently of each other, and more preferably, sulfur atoms or oxygen atoms, independently of each other.

[0090] In the general formulas (C-1) to (C-9), R 11 ~R 22 R represents a hydrogen atom or any group that does not inhibit the fluorescence of the compound, independently of each other. Examples of "any group that does not inhibit the fluorescence of the compound" include R. a and R b Any group that does not inhibit the fluorescence of the compound, as exemplified in R, can be used. 11 ~R 22 Preferably, the substituents are independently a hydrogen atom, an unsubstituted aryl group, a substituted aryl group, an unsubstituted heteroaryl group, or a substituted heteroaryl group; more preferably a hydrogen atom, an (unsubstituted) phenyl group, a p-methoxyphenyl group, a p-ethoxyphenyl group, a p-dimethylaminophenyl group, a dimethoxyphenyl group, a thienyl group, or a furanyl group; and even more preferably a hydrogen atom, an (unsubstituted) phenyl group, or a p-methoxyphenyl group. It is particularly preferable that the compound is substituted with at least one of the above unsubstituted aryl groups, substituted aryl groups, unsubstituted heteroaryl groups, or substituted heteroaryl groups, in order to enhance electron-donating ability and to suppress aggregation of the BODIPY skeleton by the bulky substituents.

[0091] As for compounds of general formula (II1-0) or general formula (II2-0), R 101 and R 104 , R 102 and R 105 , and R 103 and R 106 These may be different from each other, but it is preferable that they be of the same type. That is, R 101 , R 102 , and R 103 If the above (p1) is satisfied, R 104 , R 105 , and R 106 It is preferable that the above (q1) is satisfied, and R101 , R 102 , and R 103 If the above (p2) is satisfied, R 104 , R 105 , and R 106 It is preferable that the above (q2) is satisfied, R 101 , R 102 , and R 103 If the above (p3) is satisfied, R 104 , R 105 , and R 106 It is preferable that the above (q3) is satisfied.

[0092] As for compounds of general formula (II1-0) or general formula (II2-0), R 101 and R 102 They form a ring, R 104 and R 105 They form a ring, or R 102 and R 103 They form a ring, R 105 and R 106 It is preferable that the rings form a ring. That is, R 101 , R 102 , and R 103 The above (p2) or (p3) is satisfied, R 104 , R 105 , and R 106 It is preferable that the above-mentioned (q2) or (q3) is satisfied. This is because the condensation of an aromatic ring or heteroaromatic ring with the borondipyrrometene skeleton results in a longer wavelength for the maximum fluorescence wavelength.

[0093] In general formula (II1-0) or general formula (II2-0), R 107 and R 108 R represents a halogen atom or an oxygen atom. 107 and R 108 If it is an oxygen atom, R 107 , R 107 A boron atom bonded to it, a nitrogen atom bonded to the boron atom, R 101 , and R 101 The carbon atoms bonded to it may together form a ring, R 108 , R 108A boron atom bonded to it, a nitrogen atom bonded to the boron atom, R 104 , and R 104 The carbon atoms bonded to it may together form a ring. That is, R 107 and boron atoms and R 101 The ring formed by the etc., and R 108 and boron atoms and R 104 The rings formed by these structures all condense with the borondipyrromethene skeleton. 107 and boron atoms and R 101 The ring formed by the etc., and R 108 and boron atoms and R 104 The ring formed by these is preferably a 6-membered ring.

[0094] In general formula (II1-0) or general formula (II2-0), R 107 If it is an oxygen atom and does not form a ring, then R 107 C is an oxygen atom having a substituent (an oxygen atom bonded to a substituent). The substituent may be C 1-20 Examples include alkyl groups, aryl groups, or heteroaryl groups. Similarly, in general formula (II1-0) or general formula (II2-0), R 108 If it is an oxygen atom and does not form a ring, then R 108 C is an oxygen atom having a substituent (an oxygen atom bonded to a substituent). The substituent may be C 1-20 Examples include alkyl groups, aryl groups, or heteroaryl groups. 107 and R 108 If both are oxygen atoms with substituents, R 107 The substituents and R 108 The substituents that it possesses may be of the same type or different types.

[0095] In general formula (II1-0), R 109 R represents a hydrogen atom or an electron-withdrawing group. The electron-withdrawing group is R. gSimilar groups to those listed above can be cited. Among these, fluoroalkyl groups, nitro groups, cyano groups, aryl groups, and sulfonyl groups are preferred from the viewpoint of extending the maximum fluorescence wavelength, as they can function as strong electron-withdrawing groups. Trifluoromethyl groups, nitro groups, cyano groups, phenyl groups, and sulfonyl groups are more preferred, and trifluoromethyl groups, cyano groups, phenyl groups, and sulfonyl groups are even more preferred from the viewpoint of safety for living organisms. However, the substituents are not limited to these.

[0096] The BODIPY dye used in the present invention is a compound represented by general formula (II1-0) or general formula (II2-0), and R 101 and R 102 Both are rings represented by the above general formula (C-1), R 11 and R 12 One of them is a hydrogen atom, and the other is a halogen atom with 1 to 3 hydrogen atoms, C 1-20 Alkyl alkyl group, or C 1-20 A ring is formed which is a phenyl group, thienyl group, or furanyl group, which may be substituted with an alkoxy group, R 104 and R 105 Both are R 101 and R 102 It forms a ring of the same kind as the ring formed by R 103 and R 106 is a hydrogen atom, and R 107 and R 108 Compounds in which the atom is a halogen atom; R 101 and R 102 Both are rings represented by the above general formula (C-2), R 13 and R 14 One of them is a hydrogen atom, and the other is a halogen atom with 1 to 3 hydrogen atoms, C 1-20 Alkyl alkyl group, or C 1-20 A ring is formed which is a phenyl group, thienyl group, or furanyl group, which may be substituted with an alkoxy group, R 104 and R 105 Both are R 101 and R 102 It forms a ring of the same kind as the ring formed by R 103 and R106 is a hydrogen atom, and R 107 and R 108 Compounds in which the atom is a halogen atom; R 102 and R 103 Both are rings represented by the above general formula (C-1), R 11 and R 12 One of them is a hydrogen atom, and the other is a halogen atom with 1 to 3 hydrogen atoms, C 1-20 Alkyl alkyl group, or C 1-20 A ring is formed which is a phenyl group, thienyl group, or furanyl group, which may be substituted with an alkoxy group, R 105 and R 106 Both are R 102 and R 103 It forms a ring of the same kind as the ring formed by R 101 and R 104 is a hydrogen atom, and R 107 and R 108 Compounds in which the atom is a halogen atom; R 102 and R 103 Both are rings represented by the above general formula (C-2), R 13 and R 14 One of them is a hydrogen atom, and the other is a halogen atom with 1 to 3 hydrogen atoms, C 1-20 Alkyl alkyl group, or C 1-20 A ring is formed which is a phenyl group, thienyl group, or furanyl group, which may be substituted with an alkoxy group, R 105 and R 106 Both are R 101 and R 102 It forms a ring of the same kind as the ring formed by R 101 and R 104 is a hydrogen atom, and R 107 and R 108 Compounds in which the atom is a halogen atom; R 102 and R 103 Both are rings represented by the above general formula (C-9), R 19 ~R 22 One of the following is a halogen atom, C 1-20 Alkyl alkyl group, or C 1-20A phenyl group, thienyl group, or furanyl group which may be substituted with an alkoxy group, and the remaining three atoms form a ring with hydrogen atoms, R 105 and R 106 Both are R 101 and R 102 It forms a ring of the same kind as the ring formed by R 101 and R 104 hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, or C 1-20 A phenyl group, thienyl group, or furanyl group which may be substituted with an alkoxy group, R 107 and R 108 Compounds in which is a halogen atom; preferred. If these compounds are compounds represented by the general formula (II1-0), R 109 It is more preferable that the group is a trifluoromethyl group, a cyano group, a nitro group, or a phenyl group, and it is particularly preferable that the group is a trifluoromethyl group or a phenyl group.

[0097] As the near-infrared fluorescent material according to the present invention, compounds represented by any of the following general formulas (II3-1) to (II3-6), or compounds represented by any of the general formulas (II4-1) to (II4-6), are also preferred because their maximum fluorescence wavelength is longer.

[0098] [ka]

[0099] [ka]

[0100] In general formulas (II3-1) to (II3-6) and general formulas (II4-1) to (II4-6), R 23 , R 24 , R 25 , and R 26 These are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 R represents an alkoxy group, an aryl group, or a heteroaryl group.23 , R 24 , R 25 , or R 26 The halogen atom represented by C 1-20 Alkyl alkyl group, C 1-20 As for the alkoxy group, aryl group, and heteroaryl group, R of the general formula (II3) is... l , R m , R n , or R o Similar compounds can be cited. Compounds represented by any of the general formulas (II3-1) to (II3-6) or any of the general formulas (II4-1) to (II4-6) are considered to have high thermal stability, R 23 , R 24 , R 25 , and R 26 Preferably, the element is a halogen atom, an unsubstituted aryl group, or a substituted aryl group, specifically a fluorine atom, a chlorine atom, a bromine atom, an unsubstituted phenyl group, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group is preferred, and may be a fluorine atom, a chlorine atom, an unsubstituted phenyl group, or C 1-10 Alkyl or C 1-10 Phenyl groups substituted with alkoxy groups are more preferable, as they yield compounds that combine high luminescence efficiency and thermal stability; therefore, fluorine atoms or unsubstituted phenyl groups are particularly preferred.

[0101] In general formulas (II3-1) to (II3-6) and general formulas (II4-1) to (II4-6), R 27 and R 28 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 R represents an alkoxy group, an aryl group, or a heteroaryl group. 27 or R 28 The halogen atom represented by C 1-20 Alkyl alkyl group, C 1-20 As for the alkoxy group, aryl group, and heteroaryl group, R of the general formula (II3) is... p or R qSimilar compounds can be cited. Compounds represented by any of the general formulas (II3-1) to (II3-6) or any of the general formulas (II4-1) to (II4-6) include R 27 and R 28 It is preferable that the atom is a hydrogen atom or an aryl group, as this yields compounds with high luminescence efficiency. 1-20 Alkyl or C 1-20 Preferably, the phenyl group is substituted with an alkoxy group, and may be a hydrogen atom, an unsubstituted phenyl group, or a linear or branched C group. 1-20 A phenyl group substituted with an alkoxy group is more preferable, as it yields a compound with high luminescence efficiency and excellent compatibility with resins. 1-10 Phenyl groups substituted with alkoxy groups are particularly preferred.

[0102] In general formulas (II3-1) to (II3-6), R 29 and R 30 These independently represent a hydrogen atom or an electron-withdrawing group. 29 or R 30 The electron-withdrawing group represented by is R in the general formula (II3) above. r or R s Similar compounds can be cited. Compounds represented by any of the general formulas (II3-1) to (II3-6) can be obtained as compounds with high luminescence efficiency, R 29 and R 30 However, it is preferable that the group is a fluoroalkyl group, nitro group, cyano group, or aryl group that can function as a strong electron-withdrawing group, and more preferably a trifluoromethyl group, nitro group, cyano group, or phenyl group which may have substituents. A trifluoromethyl group or cyano group is even more preferable because it yields a compound with high luminescence efficiency and excellent compatibility with resins.

[0103] In general formulas (II3-1) and (II4-1), Y 9 and Y 10These independently represent a sulfur atom, an oxygen atom, a nitrogen atom, or a phosphorus atom. Compounds represented by general formula (II3-1) or general formula (II4-1) yield compounds with high luminescence efficiency, therefore Y 9 and Y 10 However, it is preferable that the atoms are independently sulfur atoms, oxygen atoms, or nitrogen atoms, and more preferably that they are independently sulfur atoms or oxygen atoms, as this yields a compound that combines high luminescence efficiency and thermal stability, and therefore it is even more preferable that they are both sulfur atoms or both oxygen atoms.

[0104] In general formulas (II3-3) to (II3-6) and general formulas (II4-3) to (II4-6), X 1 and X 2 These represent a nitrogen atom or a phosphorus atom independently of each other. Compounds represented by general formulas (II3-3) to (II3-6) or general formulas (II4-3) to (II4-6) include X 1 and X 2 However, compounds with high luminescence efficiency are preferable if both atoms are nitrogen or phosphorus, and compounds with both atoms are more preferable if both atoms are nitrogen, as this allows for the acquisition of compounds that combine high luminescence efficiency and thermal stability.

[0105] In general formulas (II3-1) and (II4-1), R 31 and R 32 The following conditions (p4) or (p5) are met: (p4) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group. (p5)R 31 and R 32 Both form an aromatic five-membered ring or an aromatic six-membered ring, which may have substituents. In general formulas (II3-1) and (II4-1), R 33 and R 34 The following conditions (q4) or (q5) are satisfied. (q4) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 Represents an alkoxy group, an aryl group, or a heteroaryl group, (q5)R 33 and R 34 Both form an aromatic five-membered ring or an aromatic six-membered ring, which may have substituents. In general formulas (II3-2) to (II3-6) and general formulas (II4-2) to (II4-6), R 35 , R 36 , R 37 , and R 38 It satisfies one of the following conditions (p6) to (p9). (p6) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. (p7)R 35 and R 36 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 37 and R 38 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. (p8)R 36 and R 37 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 35 and R 38 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. (p9)R 37 and R 38 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 35 and R 36 These are, independently of each other, hydrogen atoms, halogen atoms, and C1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group.

[0106] In general formulas (II3-2) to (II3-6) and general formulas (II4-2) to (II4-6), R 39 , R 40 , R 41 , and R 42 It satisfies any of the following conditions (q6) to (q9). (q6) Independently of each other, hydrogen atoms, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. (q7)R 39 and R 40 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 41 and R 42 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. (q8)R 40 and R 41 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 39 and R 42 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group. (q9)R 41 and R 42 Both form an aromatic 5-membered ring which may have substituents or an aromatic 6-membered ring which may have substituents, R 39 and R 40 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an aryl group, or a heteroaryl group.

[0107] The halogen atoms in (p4), (p6)~(p9) and (q4), (q6)~(q9), C 1-20 Alkyl alkyl group, C 1-20 As for the alkoxy group, aryl group, and heteroaryl group, R is the correct term, respectively. a and R b In the above, any group exemplified as "any group that does not inhibit the fluorescence of the compound" can be used.

[0108] In the above (p5), (p7)~(p9), (q5), (q7)~(q9), R 31 and R 32 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 33 and R 34 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 35 and R 36 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 36 and R 37 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 37 and R 38 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 39 and R 40 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 40 and R 41 A five-membered aromatic ring or a six-membered aromatic ring formed together, R 41 and R 42 The aromatic five-membered ring or aromatic six-membered ring formed by these is preferably one represented by any of the general formulas (C-1) to (C-9), and is more preferably represented by the general formula (C-9) because it yields a compound with high thermal stability.

[0109] The compound represented by (II3-1) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl, nitro, cyano, or phenyl groups; Y 9 and Y 10 Both are sulfur atoms or oxygen atoms; R 31 and R 32 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 31 and R 32 They both form a phenyl group which may have substituents; R 33 and R 34 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 33 and R 34 A compound that forms a phenyl group which may both have substituents is preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl groups, nitro groups, or cyano groups; Y 9 and Y 10 Both are sulfur atoms or oxygen atoms; R 31 and R 32 However, independently of each other, hydrogen atoms or C 1-20 It is an alkyl group, or R 31 and R 32 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group; R 33 and R 34 However, independently of each other, hydrogen atoms or C 1-20It is an alkyl group, or R 33 and R 34 Both are unsubstituted phenyl groups or C 1-10 Compounds that form phenyl groups substituted with alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0110] The compound represented by (II3-2) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl, nitro, cyano, or phenyl groups; R 35 , R 36 , R 37 , and R 38 However, independently of each other, hydrogen atoms or C 1-20 R is an alkyl group. 35 and R 36 They form a phenyl group which may both have substituents, R 37 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36 and R 37 They form a phenyl group which may both have substituents, R 35 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 They form a phenyl group which may both have substituents, R 35 and R 36 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group; R39 , R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 They form a phenyl group which may both have substituents, R 41 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 40 and R 41 They form a phenyl group which may both have substituents, R 39 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 They form a phenyl group which may both have substituents, R 39 and R 40 These are hydrogen atoms or C, which are independent of each other. 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl groups, nitro groups, or cyano groups; R 35 , R 36 , R 37 , and R 38 However, independently of each other, hydrogen atoms or C 1-20 R is an alkyl group. 35 and R 36 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 37 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36and R 37 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 and R 36 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group; R 39 , R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 41 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 40 and R 41 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 and R 40 These are hydrogen atoms or C, which are independent of each other. 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0111] The compound represented by (II3-3) above is R 23 , R 24 , R 25 , and R26 are both a halogen atom, an unsubstituted phenyl group, or a phenyl group substituted with a C 1-10 alkyl group or a C 1-10 alkoxy group; R 27 and R 28 are both a hydrogen atom, an unsubstituted phenyl group, or a phenyl group substituted with a C 1-20 alkyl group or a C 1-20 alkoxy group; R 29 and R 30 are both a trifluoromethyl group, a nitro group, a cyano group, or a phenyl group; X 1 and X 2 are both a nitrogen atom; R 36 , R 37 , and R 38 are each independently a hydrogen atom or a C 1-20 alkyl group, R 36 and R 37 together form a phenyl group which may have substituents, R 38 is a hydrogen atom or a C 1-20 alkyl group, or R 37 and R[[ID=S40]] 38 together form a phenyl group which may have substituents, R 36 is a hydrogen atom or a C 1-20 alkyl group; R 40 , R 41 , and R 42 are each independently a hydrogen atom or a C 1-20 alkyl group, R 40 and R<G 41 together form a phenyl group which may have substituents, R 42 is a hydrogen atom or a C 1-20 alkyl group, or R 41 and R 42 together form a phenyl group which may have substituents, R 40 is a hydrogen atom or a C 1-20 alkyl group, and a compound wherein R 23 , R 24 , R 25 , and R 26 are all a halogen atom or an unsubstituted phenyl group; R27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl groups, nitro groups, or cyano groups; X 1 and X 2 Both are nitrogen atoms; R 36 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36 and R 37 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 38 is a hydrogen atom or C 1-20 It is an alkyl group, or R 37 and R 38 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 36 is a hydrogen atom or C 1-20 It is an alkyl group; R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 40 and R 41 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 42 is a hydrogen atom or C 1-20 It is an alkyl group, or R 41 and R 42 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 40 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0112] The compound represented by (II3-4) above is R 23 , R24 , R 25 , and R 26 are both halogen atoms, unsubstituted phenyl groups, or phenyl groups substituted with a C 1-10 alkyl group or a C 1-10 alkoxy group; R 27 and R 28 are both hydrogen atoms, unsubstituted phenyl groups, or phenyl groups substituted with a C 1-20 alkyl group or a C 1-20 alkoxy group; R 29 and R 30 are both trifluoromethyl groups, nitro groups, cyano groups, or phenyl groups; X 1 and X 2 are both nitrogen atoms; R 35 , R 36 , and R 37 are each independently a hydrogen atom or a C 1-20 alkyl group, R 35 and R 36 together form a phenyl group which may have substituents, and R 37 is a hydrogen atom or a C 1-20 alkyl group, or R 36 and R 37 together form a phenyl group which may have substituents, and R 35 is a hydrogen atom or a C 1-20 alkyl group; R 39 , R 40 , and R 41 are each independently a hydrogen atom or a C 1-20 alkyl group, R 39 and R 40 together form a phenyl group which may have substituents, and R 41 is a hydrogen atom or a C 1-20 alkyl group, or R 40 and R 41 together form a phenyl group which may have substituents, and R 39 is a hydrogen atom or a C 1-20 alkyl group, and a compound wherein R 23 , R 24 , R 25 , and R 26Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl groups, nitro groups, or cyano groups; X 1 and X 2 Both are nitrogen atoms; R 35 , R 36 , and R 37 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 35 and R 36 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 37 is a hydrogen atom or C 1-20 It is an alkyl group, or R 36 and R 37 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 41 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 41 is a hydrogen atom or C 1-20 It is an alkyl group, or R 40 and R 41 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0113] The compound represented by (II3-5) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl, nitro, cyano, or phenyl groups; X 1 and X 2 Both are nitrogen atoms; R 35 , R 36 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 35 and R 36 They form a phenyl group which may both have substituents, R 38 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 39 and R 40 They form a phenyl group which may both have substituents, R 42 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30Both are trifluoromethyl groups, nitro groups, or cyano groups; X 1 and X 2 Both are nitrogen atoms; R 35 , R 36 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 35 and R 36 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 38 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 39 and R 40 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 42 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred because they have high luminescence efficiency and excellent compatibility with resins.

[0114] The compound represented by (II3-6) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl, nitro, cyano, or phenyl groups; X 1 and X 2 Both are nitrogen atoms; R 35 , R 37 , and R38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 They form a phenyl group which may both have substituents, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 They form a phenyl group which may both have substituents, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 29 and R 30 Both are trifluoromethyl groups, nitro groups, or cyano groups; X 1 and X 2 Both are nitrogen atoms; R 35 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 Both are unsubstituted phenyl groups or C1-10 Forms an alkyl-substituted phenyl group, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0115] The compound represented by (II4-1) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; Y 9 and Y 10 Both are sulfur atoms or oxygen atoms; R 31 and R 32 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 31 and R 32 They both form a phenyl group which may have substituents; R 33 and R 34 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 33 and R 34 A compound that forms a phenyl group which may both have substituents is preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; Y 9 and Y 10 Both are sulfur atoms or oxygen atoms; R 31 and R32 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 31 and R 32 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group; R 33 and R 34 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 33 and R 34 Both are unsubstituted phenyl groups or C 1-10 Compounds that form phenyl groups substituted with alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0116] The compound represented by (II4-2) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; R 35 , R 36 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 35 and R 36 They form a phenyl group which may both have substituents, R 37 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36 and R 37 They form a phenyl group which may both have substituents, R 35 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R37 and R 38 They form a phenyl group which may both have substituents, R 35 and R 36 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group; R 39 , R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 They form a phenyl group which may both have substituents, R 41 and R 42 However, independently of each other, hydrogen atoms or C 1-20 R is an alkyl group. 40 and R 41 They form a phenyl group which may both have substituents, R 39 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 They form a phenyl group which may both have substituents, R 39 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 35 , R 36 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 35 and R 36 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 37and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36 and R 37 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 and R 36 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group; R 39 , R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 41 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 40 and R 41 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0117] The compound represented by (II4-3) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2 Both are nitrogen atoms; R 36 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36 and R 37 They form a phenyl group which may both have substituents, R 38 is a hydrogen atom or C 1-20 It is an alkyl group, or R 37 and R 38 They form a phenyl group which may both have substituents, R 36 is a hydrogen atom or C 1-20 It is an alkyl group; R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 40 and R 41 They form a phenyl group which may both have substituents, R 42 is a hydrogen atom or C 1-20 It is an alkyl group, or R 41 and R 42 They form a phenyl group which may both have substituents, R 40 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; R 36 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 36 and R 37 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 38 is a hydrogen atom or C 1-20 It is an alkyl group, or R 37 and R 38 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 36 is a hydrogen atom or C 1-20 It is an alkyl group; R 40 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 40 and R 41 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 42 is a hydrogen atom or C 1-20 It is an alkyl group, or R 41 and R 42 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 40 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0118] The compound represented by (II4-4) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2 Both are nitrogen atoms; R 35 , R 36 , and R 37 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 35 and R 36 They form a phenyl group which may both have substituents, R 37 is a hydrogen atom or C 1-20 It is an alkyl group, or R 36 and R 37 They form a phenyl group which may both have substituents, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 41 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 They form a phenyl group which may both have substituents, R 41 is a hydrogen atom or C 1-20 It is an alkyl group, or R 40 and R 41 They form a phenyl group which may both have substituents, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2Both are nitrogen atoms; R 35 , R 36 , and R 37 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 35 and R 36 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 37 is a hydrogen atom or C 1-20 It is an alkyl group, or R 36 and R 37 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 41 These are hydrogen atoms or C, which are independent of each other. 1-20 R is an alkyl group. 39 and R 40 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 41 is a hydrogen atom or C 1-20 It is an alkyl group, or R 40 and R 41 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0119] The compound represented by (II4-5) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2 Both are nitrogen atoms; R 35 , R 36 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 35 and R 36 They form a phenyl group which may both have substituents, R 38 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 39 and R 40 They form a phenyl group which may both have substituents, R 42 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26 Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2 Both are nitrogen atoms; R 35 , R 36 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 35 and R 36 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 38 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 40 , and R 42 These are hydrogen atoms or C, which are independent of each other.1-20 It is an alkyl group, or R 39 and R 40 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 42 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0120] The compound represented by (II4-6) above is R 23 , R 24 , R 25 , and R 26 Both are halogen atoms, unsubstituted phenyl groups, or C 1-10 Alkyl or C 1-10 A phenyl group substituted with an alkoxy group; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or C 1-20 Alkyl or C 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2 Both are nitrogen atoms; R 35 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 They form a phenyl group which may both have substituents, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 They form a phenyl group which may both have substituents, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are preferred, R 23 , R 24 , R 25 , and R 26Both are halogen atoms or unsubstituted phenyl groups; R 27 and R 28 Both are hydrogen atoms, unsubstituted phenyl groups, or linear or branched C atoms. 1-20 A phenyl group substituted with an alkoxy group; X 1 and X 2 Both are nitrogen atoms; R 35 , R 37 , and R 38 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 37 and R 38 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 35 is a hydrogen atom or C 1-20 It is an alkyl group; R 39 , R 41 , and R 42 These are hydrogen atoms or C, which are independent of each other. 1-20 It is an alkyl group, or R 41 and R 42 Both are unsubstituted phenyl groups or C 1-10 Forms an alkyl-substituted phenyl group, R 39 is a hydrogen atom or C 1-20 Compounds that are alkyl groups are more preferable because they have high luminescence efficiency and excellent compatibility with resins.

[0121] The compound represented by any of (II3-1) to (II3-6) above is preferably a compound represented by any of the following general formulas (II3-7) to (II3-9), and the compound represented by any of (II4-1) to (II4-6) above is preferably a compound represented by any of the following general formulas (II4-7) to (II4-9).

[0122] [ka]

[0123] In general formulas (II3-7) and (II4-7), Y 23 and Y24 These represent, independently of each other, a carbon atom or a nitrogen atom. In general formulas (II3-7), etc., Y 23 and Y 24 It is preferable that these atoms are of the same type.

[0124] In general formulas (II3-8) and (II4-8), Y 13 and Y 14 These represent, independently of each other, an oxygen atom or a sulfur atom. In general formulas (II3-8), etc., Y 23 and Y 24 It is preferable that these atoms are of the same type.

[0125] In general formulas (II3-9) and (II4-9), Y 25 and Y 26 These represent, independently of each other, a carbon atom or a nitrogen atom. In general formulas (II3-9), etc., Y 25 and Y 26 It is preferable that these atoms are of the same type.

[0126] In general formulas (II3-7) to (II3-9), R 47 and R 48 These groups independently represent a hydrogen atom or an electron-withdrawing group, and are preferably trifluoromethyl, cyano, nitro, sulfonyl, or phenyl groups, with trifluoromethyl or cyano groups being particularly preferred, as they result in high fluorescence intensity. In general formula (II3-7), etc., R 47 and R 48 It is preferable that these are of the same type of functional group.

[0127] In general formulas (II3-7) to (II3-9) and (II4-7) to (II4-9), R 43 , R 44 , R 45 , and R 46 R represents a halogen atom or an aryl group which may have a substituent. a and R bIn the above, any group exemplified as "any group that does not inhibit the fluorescence of the compound" can be used. Furthermore, the substituent that the aryl group may have can be any group that does not inhibit the fluorescence of the compound, for example, C 1-6 Alkyl alkyl group, C 1-6 Examples include alkoxy groups, aryl groups, or heteroaryl groups. In general formulas (II3-7) to (II3-9) and (II4-7) to (II4-9), R 43 ~R 46 These may each be different groups, but it is preferable that they are all of the same type. Compounds represented by any of the general formulas (II3-7) to (II3-9) and (II4-7) to (II4-9) include R 43 ~R 46 However, it is preferable that all are halogen atoms of the same type, or that all are phenyl groups which may have substituents of the same type, more preferably that all are fluorine atoms or unsubstituted phenyl groups, and particularly preferably that all are fluorine atoms.

[0128] In general formulas (II3-7) to (II3-9) and (II4-7) to (II4-9), P 15 ~P 16 These are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an amino group, a monoalkylamino group, or a dialkylamino group. 15 ~P 16 C in 1-20 Alkyl alkyl group, C 1-20 The alkoxy group, monoalkylamino group, or dialkylamino group are, respectively, the R g The same items listed in (p1)~(p3) and (q1)~(q3) can be listed. 15 ~P 16 C 1-20 Alkyl alkyl group, C 1-20 It is preferable that the group is an alkoxy group, an (unsubstituted) phenyl group, a p-methoxyphenyl group, a p-ethoxyphenyl group, a p-dimethylaminophenyl group, a dimethoxyphenyl group, a thienyl group, or a furanyl group, and from the viewpoint of biosafety, C 1-20Alkyl alkyl group, C 1-20 More preferably, the substituent is an alkoxy group, a phenyl group, a p-methoxyphenyl group, a p-ethoxyphenyl group, a dimethoxyphenyl group, a thienyl group, or a furanyl group, and these substituents may have further substituents. However, safety can be improved by introducing other substituents as well, so the substituents are not limited to these.

[0129] In the general formulas (II3-7)~(II3-9) and (II4-7)~(II4-9), n15~n16 represent integers from 0 to 3, independently of each other. In one numerator, P 15 If there are multiple instances of (i.e., n15 is 2 or 3), multiple P 15 These may all be the same type of functional group, or they may be different types of functional groups. 16 The same applies to this matter.

[0130] In general formulas (II3-7) to (II3-9) and (II4-7) to (II4-9), A 15 ~A 16 These are, independently of each other, hydrogen atoms, halogen atoms, and C 1-20 Alkyl alkyl group, C 1-20 This represents a phenyl group which may have 1 to 3 substituents selected from the group consisting of alkoxy groups, amino groups, monoalkylamino groups, and dialkylamino groups. 1-20 Alkyl alkyl group, C 1-20 The alkoxy group, monoalkylamino group, or dialkylamino group are, respectively, the R g The same items listed in (p1)~(p3) and (q1)~(q3) are listed. A 15 ~A 16 Examples include an unsubstituted phenyl group, one or two carbon atoms. 1-20 A phenyl group having an alkoxy group as a substituent is preferred, as is an unsubstituted phenyl group or a single carbon atom. 1-20 A phenyl group having an alkoxy group as a substituent is more preferable, as is an unsubstituted phenyl group or a single carbon atom. 1-10A phenyl group having an alkoxy group as a substituent is even more preferred. Also, as a compound represented by general formula (II3-7), A 15 ~A 16 Preferably, all of them are of the same type of functional group.

[0131] Compounds represented by any of the above (II3-1) to (II3-6) include compounds represented by any of the following general formulas (6-1) to (6-12) and (7-1) to (7-12). In general formulas (6-7) to (6-12) and (7-7) to (7-12), Ph means an unsubstituted phenyl group. Among the DPP boron complexes used in the present invention, compounds represented by general formulas (6-4), (6-5), (6-7), (6-8), (7-4), (7-5), (7-7), and (7-8) are particularly preferred, and compounds represented by general formulas (6-4), (6-5), (6-7), and (6-8) are more preferred.

[0132] In general formulas (6-1) to (6-12), (7-1) to (7-12), P 5 ~P 8 These are, independently of each other, halogen atoms, C 1-20 Alkyl alkyl group, C 1-20 This represents an alkoxy group, an amino group, a monoalkylamino group, or a dialkylamino group. 5 ~P 8 C in 1-20 Alkyl alkyl group, C 1-20 The alkoxy group, monoalkylamino group, or dialkylamino group are, respectively, the R g The same items listed in (p1)~(p3) and (q1)~(q3) can be listed. 5 ~P 8 C 1-20 Alkyl alkyl group, C 1-20 It is preferable that the group is an alkoxy group, an (unsubstituted) phenyl group, a p-methoxyphenyl group, a p-ethoxyphenyl group, a p-dimethylaminophenyl group, a dimethoxyphenyl group, a thienyl group, or a furanyl group, and from the viewpoint of biosafety, C 1-20 Alkyl alkyl group, C 1-20It is more preferably an alkoxy group, a phenyl group, a p-methoxyphenyl group, a p-ethoxyphenyl group, a dimethoxyphenyl group, a thienyl group, or a furanyl group, C 1-20 Alkyl or C 1-20 It is even more preferable that it be an alkoxy group, C 1-10 Alkyl or C 1-10 It is even more preferable that the substituents be alkoxy groups, and these substituents may have further substituents. However, safety can be improved by introducing other substituents as well, so the substituents are not limited to these.

[0133] In the general formulas (6-1)~(6-12) and (7-1)~(7-12), n5~n8 represent integers from 0 to 3, independently of each other. In one numerator, P 5 If there are multiple instances of (i.e., n5 is 2 or 3), multiple P 5 These may all be the same type of functional group, or they may be different types of functional groups. 6 ~P 8 The same applies to this matter.

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138] Compounds represented by general formulas (6-1) to (6-12) and (7-1) to (7-12) include P 5 ~P8 C 1-20 Alkyl or C 1-20 It is an alkoxy group, and preferably n5 to n8 are independently 0 to 2, P 5 and P 6 C 1-20 It is an alkyl group, and n5 and n6 are independently 0 to 2, P 7 and P 8 C 1-20 It is more preferable that the alkoxy group has n7 and n8 independently of each other being 0 to 1, P 5 and P 6 C 1-20 It is an alkyl group, and n5 and n6 are independently 1 to 2, P 7 and P 8 C 1-20 It is more preferable that the alkoxy group has n7 and n8 as 1.

[0139] Compounds represented by general formulas (6-1) to (6-12) specifically include those represented by the following formulas (6-1-1) to (6-12-1). "λ" is the peak wavelength of the absorption spectrum in solution of each compound, and "Em" is the peak wavelength of the fluorescence spectrum.

[0140] [ka]

[0141] [ka]

[0142] The near-infrared fluorescent material (A) according to the present invention may be a commercially available product or a synthesized product. An example of a synthesis method is the one described in Chemistry A European Journal, 2009, Vol. 15, pp. 4857-4864.

[0143] The content of the near-infrared fluorescent material (A) is not particularly limited as long as the concentration of the near-infrared fluorescent material (A) can be mixed with the thermoplastic resin (B). However, from the viewpoint of fluorescence intensity and detection sensitivity, the content of the near-infrared fluorescent material (A) may be preferably in the range of 0.0005% by mass or more, more preferably 0.001% by mass or more, based on 100% by mass of the total of the near-infrared fluorescent material (A) and the thermoplastic resin (B), and from the viewpoint of detection sensitivity due to concentration quenching and reabsorption of fluorescence, it may be preferably in the range of 1% by mass or less, more preferably 0.8% by mass or less, and even more preferably 0.5% by mass or less.

[0144] The near-infrared fluorescent material used in this invention has a high molar extinction coefficient and a high quantum yield even in the resin, so its emission can be clearly seen with a camera or the like even if the concentration of the near-infrared fluorescent material in the resin is relatively low. A low concentration of the near-infrared fluorescent material is preferable because it reduces the possibility of elution, reduces the possibility of bleed-out from molded articles processed from the resin composition, and allows for the processing of molded articles where transparency is required.

[0145] <Thermoplastic resins other than polyamide resins (B)> The thermoplastic resin (B) other than polyamide resin used in the present invention forms a dispersed phase in a masterbatch, resin composition, or molded article together with a near-infrared fluorescent material.

[0146] The thermoplastic resin (B) used in the present invention is not particularly limited as long as it is a thermoplastic resin other than a polyamide resin. It can be appropriately selected from known resins, taking into consideration the type of near-infrared fluorescent substance to be blended, the required product quality when forming the molded article, etc. The thermoplastic resin (B) used in the present invention may be used alone or as a mixture of two or more types. When mixing two or more types, it is preferable to use resins that have high compatibility with each other. Furthermore, the thermoplastic resin (B) may be a commercially available product or a synthetic product.

[0147] Specific examples of the thermoplastic resin (B) used in the present invention include, for example, thermoplastic polyurethane (TPU); polycarbonate (PC) resin; polyvinyl chloride (PVC) and vinyl chloride-vinyl acetate copolymer resins; acrylic resins such as polyacrylic acid, polymethacrylic acid, polymethyl polyacrylate, polymethyl methacrylate (PMMA), and polyethyl methacrylate; polyester resins such as polyethylene terephthalate (PET), polybutylene terephthalate, polytrimethylene terephthalate, polyethylene naphthalate, and polybutylene naphthalate; polystyrene resins such as polystyrene (PS), imide-modified polystyrene, acrylonitrile-butadiene-styrene (ABS) resin, imide-modified ABS resin, styrene-acrylonitrile copolymer (SAN) resin, and acrylonitrile-ethylene-propylene-diene-styrene (AES) resin; olefin resins such as polyethylene (PE) resin, polypropylene (PP) resin, and cycloolefin resin; polyacetal (POM) resin; cellulose resins such as nitrocellulose and cellulose acetate; silicone resins; and fluororesins.

[0148] Among these thermoplastic resins (B), it is preferable that the thermoplastic resin (B) includes at least one selected from the group consisting of thermoplastic polyurethane (TPU) resin, polycarbonate (PC) resin, vinyl chloride resin, acrylic resin, polyester resin, polystyrene resin, olefin resin, and polyacetal (POM) resin, due to its high dispersibility of near-infrared fluorescent materials. In particular, when the resin composition according to the present invention is used as a medical material, considering its low solubility in bodily fluids such as blood, its resistance to leaching in the usage environment, and its biocompatibility, the thermoplastic resin (B) is more preferably TPU, PC, PVC, PMMA, PET, PS, PE, or PP, and even more preferably TPU, PC, PMMA, PS, or PE.

[0149] The content of the thermoplastic resin (B) is not particularly limited as long as the concentration of the near-infrared fluorescent material (A) can be mixed with the thermoplastic resin (B). However, from the viewpoint of fluorescence intensity and detection sensitivity, the content of the thermoplastic resin (B) may be preferably in the range of 99% by mass or more, more preferably 99.2% by mass or more, and even more preferably 99.5% by mass or more, and preferably 99.9995% by mass or less, and more preferably 99.999% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A) and the thermoplastic resin (B).

[0150] <Resin (C)> The resin (C) used in the present invention is a resin different from the thermoplastic resin (B), and forms a continuous phase in the masterbatch, resin composition, or molded article.

[0151] The resin (C) is not particularly limited as long as it is different from the thermoplastic resin (B), and may be a thermoplastic resin or a thermosetting resin. Polyamide resins and thermosetting resins that can deactivate the above-mentioned near-infrared fluorescent material can also be used as the resin (C) that forms the continuous phase, and a resin composition and molded articles thereof with high near-infrared fluorescence luminescence efficiency can be obtained.

[0152] Resin (C) may be used alone or as a mixture of two or more types. Furthermore, resin (C) may be a commercially available product or a synthetic product.

[0153] Specific examples of resin (C) used in the present invention include, for example, urethane resins such as polyurethane (PU) resin and thermoplastic polyurethane (TPU) resin; polycarbonate (PC) resin; vinyl chloride resins such as polyvinyl chloride (PVC) and vinyl chloride-vinyl acetate copolymer resin; acrylic resins such as polyacrylic acid, polymethacrylic acid, polymethyl polyacrylate, polymethyl methacrylate (PMMA), and polyethyl methacrylate; polyester resins such as polyethylene terephthalate (PET), polybutylene terephthalate, polytrimethylene terephthalate, polyethylene naphthalate, and polybutylene naphthalate; polyamide resins such as nylon (registered trademark); polystyrene (PS), imide-modified polystyrene, and acrylonitrile-butadiene Examples of polystyrene resins include styrene-styrene (ABS) resin, imide-modified ABS resin, styrene-acrylonitrile copolymer (SAN) resin, and acrylonitrile-ethylene-propylene-diene-styrene (AES) resin; olefin resins such as polyethylene (PE) resin, polypropylene (PP) resin, polybutylene resin, and cycloolefin resin; cellulose resins such as nitrocellulose and cellulose acetate; silicone resins; thermoplastic resins such as fluororesins; epoxy resins such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, isocyanurate-based epoxy resin, and hydantoin-based epoxy resin; amino resins such as melamine resin and urea resin; phenolic resins; and thermosetting resins such as unsaturated polyester resins.

[0154] Among these, from the viewpoint of deactivating the near-infrared fluorescent material (A) or improving its fluorescence intensity, it is preferable that the resin (C) contains at least one selected from the group consisting of polyamide resin, polyethylene resin, polypropylene resin, and thermosetting resin. Furthermore, from the viewpoint of heat resistance and chemical resistance, it is more preferable that the resin (C) contains polyamide resin. Also, from the viewpoint of insulation and dielectric strength, it is more preferable that the resin (C) contains thermosetting resin.

[0155] The content of resin (C) in the masterbatch according to the present invention is not particularly limited as long as the concentration allows the particles (powder) containing the near-infrared fluorescent material (A) and thermoplastic resin (B) to be mixed with resin (C). However, since resin (C) efficiently forms a continuous phase and the resin composition and molded articles produced via the masterbatch thereafter can obtain excellent luminescence efficiency, the content of resin (C) may preferably be in the range of 20% by mass or more, more preferably 30% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), thermoplastic resin (B), and resin (C).

[0156] Therefore, the total content of the near-infrared fluorescent material (A) and thermoplastic resin (B) in the masterbatch according to the present invention may be preferably 20% by mass or more, more preferably 30% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), thermoplastic resin (B), and resin (C).

[0157] <Method for producing masterbatches and resin compositions> The method for producing a masterbatch according to the present invention comprises the steps of: melting and kneading a near-infrared fluorescent material (A) and a thermoplastic resin other than a polyamide resin (B) to obtain a kneaded product; pulverizing the kneaded product obtained in the first step to obtain particles containing powdered near-infrared fluorescent material (A) and thermoplastic resin (B); and mixing or kneading the particles obtained in the first step with a resin (C).

[0158] First, the near-infrared fluorescent material (A) and thermoplastic resin (B) are blended as essential components in the above-mentioned proportions, and then uniformly mixed in a tumbler or Henschel mixer (registered trademark). Next, the mixture is fed into a melt-kneading extruder such as a twin-screw kneading extruder and melt-kneaded at a temperature range of above the melting temperature of the thermoplastic resin (B) and up to 100°C above that temperature, for example, between 180°C and 300°C, to obtain a mixture of the near-infrared fluorescent material, which will form the dispersed phase, and the thermoplastic resin (B). The melting temperature of the thermoplastic resin refers to the melting point for crystalline resins and the softening point (glass transition point) for amorphous resins (the same applies hereinafter). Next, the kneaded material is powdered. For example, the kneaded material can be extruded into strands and then cooled by leaving it at room temperature or by immersing it in water at a temperature range of 5°C to 60°C, and then cut to form pellets, chips, or other particles. After that, if necessary, the obtained particles can be freeze-dried to obtain powdered particles (powder) containing a near-infrared fluorescent material (A) and a thermoplastic resin (B) having a desired size. The average particle size of the particles (powder) after pulverization is not particularly limited, but is preferably in the range of 5 μm or more, more preferably in the range of 10 μm or more, even more preferably in the range of 15 μm or more, and preferably in the range of 500 μm or less, more preferably in the range of 200 μm or less, and even more preferably in the range of 100 μm or less.

[0159] Furthermore, at least the particles (powder) containing the near-infrared fluorescent material (A) and thermoplastic resin (B) obtained in this manner can be blended with resin (C) in the above-mentioned proportions, and then uniformly mixed in a tumbler or Henschel mixer (registered trademark) to obtain a resin mixture.

[0160] Subsequently, if resin (C) is a thermoplastic resin, the obtained resin mixture can be fed into a melt-kneading extruder such as a twin-screw kneading extruder and melt-kneaded in a range above the melting temperature of resin (C) and below the melting temperature of thermoplastic resin (B) to obtain the masterbatch of the present invention. Furthermore, the masterbatch can be extruded into strands and then cooled by leaving it at room temperature or by immersing it in water in a temperature range of 5°C to 60°C, and then cut to form pellets, chips, or other granular material.

[0161] When a thermosetting resin is used as resin (C), the resulting resin mixture is still an intermediate state between a prepolymer and an initial polycondensate. Therefore, a curing agent is added to the resin mixture as needed, and after further molding (shaping), a heating step is performed to cause resin (C) to form a three-dimensional structure, thereby obtaining the resin composition of the present invention as a molded article. During this polymerization process, it is preferable that the heating step is performed at a temperature range from room temperature to below the melting temperature of the thermoplastic resin (B).

[0162] Next, the resin composition of the present invention comprises the step of adding resin (D) as a diluent resin to the masterbatch and mixing or kneading it.

[0163] The aforementioned resin (D) is used as a diluent in the masterbatch, and the diluted resin (D) is a different resin from the thermoplastic resin (B), and together with the aforementioned resin (C), forms a continuous phase in the resin composition or molded article. Examples of diluent resin (D) include those similar to resin (C). While different types of resins may be used for resin (C) and diluent resin (D), it is preferable to use the same type of resin.

[0164] When using an epoxy resin as resin (D), it may be in the form of an epoxy resin composition containing a curing agent.

[0165] The resin (D) may be a resin having a crosslinked structure. In that case, a crosslinking agent for creating a crosslinked structure can be added to an olefin resin such as polyethylene resin or polybutylene resin, and then molded into a molded article. Examples of resins having a crosslinked structure include crosslinked olefin resins such as crosslinked polyethylene resin and crosslinked polybutylene resin, and silane-modified products thereof.

[0166] Furthermore, from the viewpoint of moldability and luminescence efficiency, the following configurations are preferred combinations of thermoplastic resin (B), resin (C), and resin (D); • A form in which the thermoplastic resin (B) is a polycarbonate resin, and resin (D) is, more preferably, resin (C) and resin (D) is a polyamide resin. • A form in which the thermoplastic resin (B) is a polycarbonate resin, and resin (D) is, more preferably, a cross-linked polyethylene resin, with resin (C) and resin (D) being cross-linked polyethylene resins. • A form in which the thermoplastic resin (B) is a polycarbonate resin, and resin (D) is, more preferably, resin (C) and resin (D) is an epoxy resin composition. • A form in which the thermoplastic resin (B) is a polycarbonate resin, and resin (D) is, more preferably, resin (C) and resin (D) are thermoplastic polyurethane resins. • A form in which the thermoplastic resin (B) is a polymethyl methacrylate resin, and resin (D) is, more preferably, a cross-linked polyethylene resin. A form in which the thermoplastic resin (B) is polypropylene resin, and resin (D), more preferably resin (C) and resin (D), are polyethylene resins.

[0167] The content of resin (D) in the resin composition according to the present invention is not particularly limited as long as the masterbatch can be mixed with resin (D) at a concentration. However, since resin (D) efficiently forms a continuous phase together with resin (C), and thereafter the resin composition and its molded article can obtain excellent luminescence efficiency, the content of resin (D) may be preferably in the range of 20% by mass or more, more preferably 30% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), thermoplastic resin (B), resin (C), and resin (D).

[0168] Therefore, the total content of the near-infrared fluorescent material (A), thermoplastic resin (B), and resin (C) in the resin composition according to the present invention may be preferably 20% by mass or more, more preferably 30% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), thermoplastic resin (B), resin (C), and resin (D).

[0169] As a method for producing the resin composition, if resin (D) is a thermoplastic resin, resin (D) is added to the masterbatch described above, and the mixture is uniformly mixed using a tumbler or Henschel mixer (registered trademark) to obtain a resin mixture. Subsequently, the obtained resin mixture is put into a melt-kneading extruder such as a twin-screw kneading extruder and melt-kneaded in a range above the melting temperature of resin (C) and resin (D) but below the melting temperature of thermoplastic resin (B) to obtain the resin composition of the present invention. Furthermore, the resin composition of the present invention can be extruded into strands and then cooled by leaving it at room temperature or by immersing it in water in a temperature range of 5°C to 60°C, and then cut to obtain pellets, chips, or other granular forms.

[0170] Furthermore, when producing a resin composition capable of forming a crosslinked structure such as a crosslinked polyolefin resin, conventionally known crosslinking methods such as a chemical crosslinking method using a crosslinking agent (organic peroxide), an active energy beam crosslinking method using electron beam or X-ray irradiation, or a water crosslinking method that uses the dehydration condensation reaction of alkoxysilane after silane modification of the polyolefin resin can be employed to obtain a molded resin according to a conventional method. Therefore, a molded article having a crosslinked structure can be obtained by uniformly mixing the resin (D) before crosslinking (and a crosslinking agent in the case of chemical crosslinking) with a masterbatch (or a thermoplastic resin (B) that has been pre-modified with silane in the case of water crosslinking), then kneading the resulting resin mixture using a known kneading device such as a two-roll machine, kneader, Banbury mixer, or extruder, under conditions where the temperature is in the range of above the melting temperatures of resin (C) and resin (D) and below the melting temperature of resin (B), and further, if a crosslinking agent is included, under conditions where the temperature is below the thermal decomposition temperature of the crosslinking agent, and then molding the mixture, followed by a crosslinking step according to each crosslinking method (for example, heating above the thermal decomposition temperature of the crosslinking agent in the chemical crosslinking method, irradiating with active energy rays in the active energy ray crosslinking method, and exposing to a water atmosphere in the water crosslinking method).

[0171] Furthermore, if resin (D) is a thermosetting resin (or, in the preferred form, if both resin (C) and resin (D) are thermosetting resins), resin (D) is added to the obtained masterbatch and stirred to produce a resin mixture. Since the obtained resin mixture is still an intermediate prepolymer or initial polycondensate, a curing agent can be added to the resin mixture as needed, followed by molding (shaping) and then a heating step to obtain a molded article in which resin (D) (or, in the preferred form, resin (C) and resin (D)) have formed a three-dimensional structure. Alternatively, resin (D) and a curing agent can be added to the obtained masterbatch and stirred to mix, followed by molding (shaping) and then a heating step to obtain a molded article in which resin (D) (or, in the preferred form, resin (C) and resin (D)) have formed a three-dimensional structure. During the polymerization process, the heating step is preferably conducted within a temperature range from room temperature to below the melting temperature of the thermoplastic resin (B).

[0172] The content of the near-infrared fluorescent material (A) in the resin composition according to the present invention is not particularly limited, but is preferably in the range of 0.000025% by mass or more, more preferably 0.00005% by mass or more, and even more preferably 0.0001% by mass or more, with respect to 100% by mass of the total of the near-infrared fluorescent material (A), thermoplastic resin (B), resin (C), and resin (D), and is preferably in the range of 0.6% by mass or less, more preferably 0.5% by mass or less, and even more preferably 0.48% by mass or less.

[0173] In the masterbatch according to the present invention, the diameter (dispersion diameter) of the dispersed phase formed by the near-infrared fluorescent material (A) and the thermoplastic resin (B) is preferably in the range of 1 nm or more, preferably in the range of 300 μm or less, and more preferably in the range of 200 μm or less. By setting it within this range, the luminescence efficiency of the resin composition and molded article produced via the masterbatch according to the present invention is further improved.

[0174] The diameter of the dispersed phase can be controlled by conditions such as the freeze-grinding conditions of the particles containing the near-infrared fluorescent material (A) and thermoplastic resin (B), the melt-kneading conditions when mixing the resin (C), and the mixing or kneading conditions when mixing the resin (D). Furthermore, the diameter of the dispersed phase can be measured by the method described in the examples.

[0175] When detecting the emission of light emitted from a molded body by irradiating it with excitation light, if a general light emission detector equipped with a filter to cut noise caused by the excitation light is used, if the Stokes shift of the resin composition according to the present invention is small, the emission will be cut off by the filter, making it difficult to detect with high sensitivity. For this reason, the resin composition according to the present invention preferably has a Stokes shift (difference between the maximum absorption wavelength and the maximum emission wavelength) of 10 nm or more, and more preferably a Stokes shift of 20 nm or more. The larger the Stokes shift, the more sensitively the emission emitted from the molded body can be detected, even when using a general detector equipped with a filter to cut noise caused by the excitation light.

[0176] However, even with a small Stokes shift, near-infrared fluorescence from the resin composition according to the present invention can be detected with high sensitivity under the following conditions. For example, if excitation can be performed with light of a shorter wavelength than the maximum absorption wavelength, fluorescence can be detected even with noise reduction. Also, if the fluorescence spectrum is broad, fluorescence can be sufficiently detected even with noise reduction. On the other hand, some fluorescent materials have multiple fluorescence peaks. In that case, even with a small Stokes shift, if there is a fluorescence peak (second peak) on the longer wavelength side, detection with high sensitivity is possible even when using a detector equipped with a noise reduction filter. When the resin composition according to the present invention has multiple fluorescence peaks, the difference between the fluorescence peak wavelength on the longer wavelength side and the maximum absorption wavelength should be 30 nm or more, and preferably 50 nm or more. Note that the above conditions are not limited if the excitation light source and cut filter are appropriately selected.

[0177] The resin composition according to the present invention, which contains a near-infrared fluorescent material (A), does not change color to the naked eye when excited by excitation light in the near-infrared region, and emits invisible near-infrared fluorescence that can be detected by a detector. Therefore, for excitation light in the near-infrared region, the maximum absorption wavelength should be 600 nm or higher, but from the viewpoint of absorption efficiency, it is preferable that the maximum absorption wavelength is close to the wavelength of the excitation light, more preferably 650 nm or higher, even more preferably 665 nm or higher, and particularly preferably 680 nm or higher. Furthermore, when used as a medical device such as an implant, 700 nm or higher is preferable.

[0178] The masterbatch, resin composition, and molded article obtained from the present invention, which contain a near-infrared fluorescent material (A), do not change the color of the irradiated object, and considering the detection sensitivity, there are no practical problems if the maximum fluorescence wavelength is 650 nm or higher, but it is preferable that it is 700 nm or higher, and more preferably 720 nm or higher. If there are multiple fluorescence peaks, even if the wavelength of the maximum fluorescence peak is 720 nm or lower, it is sufficient if there is a fluorescence peak with sufficient detection sensitivity at 740 nm or higher. In that case, it is preferable that the intensity of the long-wavelength fluorescence peak (second peak) is 5% or higher, and more preferably 10% or higher, of the intensity of the maximum fluorescence wavelength.

[0179] The resin composition and molded articles obtained from the present invention preferably exhibit strong absorption in the range of 650 nm to 1500 nm and emit strong fluorescence in this range. Light above 650 nm is less affected by hemoglobin, and light below 1500 nm is less affected by water. In other words, light in the range of 650 nm to 1500 nm has high skin permeability and is less affected by interfering substances in the body, making it suitable as a wavelength range of light used to visualize medical implants embedded subcutaneously, etc. When the maximum absorption wavelength and maximum fluorescence wavelength are in the range of 650 nm to 1500 nm, the resin composition and molded articles obtained from the present invention are suitable for detection using light in the range of 650 nm to 1500 nm and are suitable as medical devices, etc., used in the body.

[0180] The masterbatch or resin composition according to the present invention may contain other components besides the resin component and the near-infrared fluorescent material (A), as long as the effects of the present invention are not impaired. Examples of such other components include ultraviolet absorbers, heat stabilizers, light stabilizers, antioxidants, flame retardants, flame retardant aids, crystallization accelerators, plasticizers, antistatic agents, colorants, and mold release agents.

[0181] <Molded body> By molding the resin composition according to the present invention, a molded article capable of detecting light emission can be obtained. That is, according to another embodiment of the present invention, a molded article obtained from the resin composition according to the present invention is provided.

[0182] The molding method is not particularly limited and includes casting, injection molding using a mold, compression molding, and extrusion molding using a T-die, blow molding, etc.

[0183] In the manufacture of a molded article, it may be formed solely from the resin composition according to the present invention, or a combination of the resin composition according to the present invention and other resin compositions may be used as raw materials. For example, the entire molded article may be molded using the resin composition according to the present invention, or only a portion of the molded article may be molded using the resin composition according to the present invention. The resin composition according to the present invention is preferably used as a raw material to constitute the surface portion of the molded article. For example, when molding a catheter, by molding only the tip of the catheter using the resin composition according to the present invention and the remaining portion using a resin composition that does not contain near-infrared fluorescent material, a catheter in which only the tip emits near-infrared fluorescence can be manufactured. Furthermore, by alternately laminating the resin composition according to the present invention and a resin composition that does not contain near-infrared fluorescent material, a molded article that emits near-infrared fluorescence in a striped pattern can be manufactured. In addition, a surface coating may be applied to improve the visibility of the molded article.

[0184] Luminescence detection can be performed using commercially available fluorescence or phosphorescence detection devices and other conventional methods. Any light source can be used as the excitation light for fluorescence or phosphorescence detection; in addition to near-infrared lamps with a long wavelength range, lasers and LEDs with a narrow wavelength range can also be used.

[0185] A molded article obtained from the resin composition according to the present invention containing a near-infrared fluorescent material (A) does not change color when irradiated with light in the near-infrared region and emits near-infrared fluorescence that can be detected with higher sensitivity than conventional materials. Therefore, the molded article is particularly suitable for medical devices in which at least a portion is inserted or implanted in the patient's body.

[0186] When detecting fluorescence in a molded article obtained from a resin composition according to the present invention containing a near-infrared fluorescent material (A), it is preferable to irradiate it with excitation light in the near-infrared region. However, if it is acceptable for the color of the irradiated object to be slightly reddish, it is not always necessary to use excitation light in the near-infrared region. For example, when attempting to detect fluorescence in a medical device inside the body by irradiating it with excitation light, it is necessary to use excitation light in a wavelength range that has high penetration into living organisms such as skin. In this case, excitation light of 650 nm or higher, which has high penetration into living organisms, should be used.

[0187] Examples of such medical devices include stents, coil embolization devices, catheter tubes, injection needles, indwelling needles, ports, shunt tubes, drainage tubes, and implants.

[0188] <Detection method, detection device, verification system> The detection method of the present invention comprises the steps of irradiating the molded body with near-infrared light and detecting the near-infrared light emitted by the molded body using a device for detecting near-infrared light emission.

[0189] Furthermore, the detection device of the present invention includes means for irradiating the molded body with near-infrared light and means for detecting the near-infrared light emitted by the molded body.

[0190] As a means of irradiating the molded body with near-infrared light, any light source capable of irradiating excitation light used for light emission detection can be used, and in addition to near-infrared lamps with a long wavelength range, lasers and LEDs with a narrow wavelength range can be used. The wavelength of the irradiating light source should be any wavelength capable of exciting the near-infrared fluorescent dye contained in the molded body, and generally any wavelength called near-infrared light is acceptable, but for example, 650 nm or more is preferred, 700 nm or more is more preferred, 2500 nm or less is preferred, and 1100 nm or less is even more preferred.

[0191] The irradiation of the molded body with near-infrared light is not particularly limited as long as it is done by conventional methods. For example, one or more light sources may be used to irradiate the molded body from above or below in the vertical direction, from an oblique direction, or from different directions relative to the molded body. When the light source and the near-infrared emission detection device described later are placed in substantially the same position relative to the molded body, it is preferable to use ring illumination or line illumination as the light source.

[0192] As a means of detecting near-infrared emission, commercially available near-infrared emission detection devices are generally sufficient and are not particularly limited. For example, imaging devices such as digital cameras using image sensors such as CCDs (Charge Coupled Devices) or CMOSs ​​(Complementary MOS), or detection devices such as spectrometers, photomultiplier tubes, PbS detectors, and photodiodes can be used. The imaging device may be an area camera or a line camera. If a detector other than an imaging device, such as a photodiode, is used as a means of detecting near-infrared emission, the electrical signal from the detector can be amplified by a circuit board equipped with a signal amplification unit such as a head amplifier, and the presence or absence of emission can be detected by the output value of the amplified electrical signal.

[0193] Furthermore, by providing means for analyzing the presence or absence of near-infrared emission detection, it is possible to determine the presence or absence of the molded product of the present invention based on the emission information. The analysis means can be commercially available and is not particularly limited, but for example, a personal computer with image analysis software installed or hardware capable of implementing an image processing algorithm (e.g., a microcontroller, PLC (programmable controller), FPGA (Field-Programmable Gate Array), etc.) can be used.

[0194] The position confirmation system of the present invention further comprises a monitor that displays captured images, in addition to the detection device of the present invention. If the molded body of the present invention is a medical device, it can be used as a medical device position confirmation system, allowing the position of a medical device inserted or left in the body during surgery or the like to be visually confirmed. [Examples]

[0195] The present invention will be described in more detail using the following examples and comparative examples. However, the technical scope of the present invention is not limited to the following examples. In the following examples, the notations "%" and "parts" refer to "mass%" and "parts by mass" respectively, unless otherwise specified.

[0196] (Preparation of near-infrared fluorescent material (A)) Near-infrared fluorescent materials 1-3 (dyes 1-3 of the following formulas) were synthesized with reference to Chemistry A European Journal, 2009, Vol. 15, pp. 4857-4864.

[0197] Dye 1 (compound of the above chemical formula 6-4-1)

[0198] [ka]

[0199] Example of dye 1 synthesis

[0200] [ka]

[0201] <Synthesis of pigment 1> The synthesis of pigment 1 was carried out as follows, referring to Organic Letters, 2012, Vol. 4, pp. 2670-2673, and Chemestry A European Journal, 2009, Vol. 15, pp. 4857-4864.

[0202] In a 2L four-necked flask, 4-hydroxybenzonitrile (25.3g, 212 mmol), acetone (800 mL), potassium carbonate (100 g, 724 mmol), and 1-bromooctane (48 g, 249 mmol) were placed and heated under reflux overnight. After filtering out the inorganic salts, the acetone was removed under reduced pressure. Ethyl acetate was added to the resulting residue, and the organic layer was washed with water and saturated brine, then treated with anhydrous magnesium sulfate. After filtering out the magnesium sulfate and removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain a colorless, transparent liquid of 4-octoxybenzonitrile (1-1) (yield: 45.2 g, yield: 92%).

[0203] Next, under an argon stream, tert-butyloxypotassium (25.18 g, 224.4 mmol) and tert-amyl alcohol (160 mL) were placed in a 500 mL four-necked flask. Then, a solution of the previously synthesized compound (1-1) (14.8 g, 64 mmol) mixed with tert-amyl alcohol (7 mL) was added, and the mixture was heated under reflux. Under reflux, a solution of diisopropyl succinate (6.5 g, 32 mmol) mixed with tert-amyl alcohol (10 mL) was added dropwise over approximately 3 hours. After the addition was complete, the mixture was heated under reflux for 6 hours. After returning to room temperature, the resulting highly viscous reaction solution was placed in a solution of acetic acid:methanol:water = 1:1:1 (volume ratio), and heated under reflux for several minutes, at which point a red solid precipitated. The solid was filtered and washed with heated methanol and water to obtain a red solid of 3,6-(4-octyloxyphenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione(1-2) (yield: 5.6 g, yield: 32%).

[0204] In addition, 4-tert-butylaniline (10 g, 67 mmol), acetic acid (70 mL), and sodium thiocyanate (13 g, 160 mmol) were placed in a 200 mL three-necked flask. While maintaining the system temperature below 15°C, bromine (4.5 mL, 87 mmol) was added dropwise over approximately 20 minutes, and then the mixture was stirred at below 15°C for 3.5 hours. The reaction mixture was placed in 28% aqueous ammonia (150 mL), stirred for a while, and the precipitated solid was filtered off. The solid was then extracted with diethyl ether, and the organic layer was washed with water. After removing the diethyl ether under reduced pressure, the residue was purified by silica gel column chromatography (eluent: dichloromethane / ethyl acetate) to obtain 2-amino-6-tert-butylbenzothiazole (1-3) as a pale yellow solid (yield: 10.32 g, yield: 69%).

[0205] Next, under water cooling, potassium hydroxide (75.4 g, 1340 mmol) and ethylene glycol (175 mL) were placed in a 1 L four-necked flask. The system was subjected to an argon atmosphere, compound (1-3) (7.8 g, 37.8 mmol) was added, and after bubbling with argon to remove oxygen from the system, the reaction was carried out at 110°C for 18 hours. The reaction solution was cooled with water to below 40°C, and 2 mol / L hydrochloric acid, which had been pre-bubbled with argon, was added dropwise to the system to neutralize it (around pH 7). The precipitated white solid was filtered off, washed with water, and dried under reduced pressure. Subsequently, the white solid was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain a white solid of 4-tert-butyl-2-mercaptoaniline (1-4) (yield: 2.39 g, yield: 35%).

[0206] Furthermore, acetic acid (872 mg, 14.5 mmol) and acetonitrile (30 mL) were placed in a 100 mL three-necked flask, and the system was subjected to an argon atmosphere. Under the argon atmosphere, malononitrile (2.4 g, 36.3 mmol) and compound (1-4) (2.39 g, 13.2 mmol) were added, and the mixture was heated under reflux for 2 hours. Acetonitrile was removed under reduced pressure, the residue was dissolved in ethyl acetate, the organic layer was washed with water and saturated brine, and treated with anhydrous magnesium sulfate. Magnesium sulfate was filtered off, and after removing the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain a pale yellow solid of 2-(6-tert-butylbenzothiazole-2-yl)acetonitrile (1-5) (yield: 1.98 g, yield: 65%).

[0207] Next, under an argon stream, compound (1-2) (1.91 g, 3.5 mmol), compound (1-5) (1.77 g, 7.68 mmol), and anhydrous toluene (68 mL) were added to a 200 mL three-necked flask and heated under reflux. Under reflux, phosphoryl chloride (2.56 mL, 27.4 mmol) was added dropwise using a syringe, and the mixture was heated under reflux for a further 2 hours. After the reaction was complete, while cooling with ice, dichloromethane (40 mL) and saturated sodium bicarbonate aqueous solution (40 mL) were added, and the mixture was extracted with dichloromethane. The organic layer was treated with anhydrous magnesium sulfate, the magnesium sulfate was filtered off, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate) to roughly remove impurities. The residue obtained by distilling off the solvent was purified again by silica gel column chromatography (eluent: hexane / dichloromethane) to obtain the green solid precursor (1-6) (yield: 1.56 g, yield: 46%).

[0208] Finally, under an argon stream, precursor (1-6) (1.52 g, 1.57 mmol), toluene (45 mL), triethylamine (4.35 mL, 31.4 mmol), and boron trifluoride diethyl ether complex (7.88 mL, 62.7 mmol) were added to a 200 mL three-necked flask and heated under reflux for 1 hour. The reaction mixture was cooled on ice, the precipitated solid was filtered off, and the solid was washed with water, saturated sodium bicarbonate aqueous solution, 50% methanol aqueous solution, and methanol, and dried under reduced pressure. The resulting residue was dissolved in toluene, and methanol was added to precipitate the dark green solid of dye 1 (yield: 1.25 g, yield: 75%).

[0209] Dye 2 (compound of the above chemical formula 6-5-1)

[0210] [ka]

[0211] Example of dye 2 synthesis

[0212] [ka]

[0213] <Synthesis of pigment 2> Pigment 2 was prepared as follows, referring to Organic Letters, 2012, Vol. 4, pp. 2670-2673, and Chemestry A European Journal, 2009, Vol. 15, pp. 4857-4864.

[0214] In a 300 mL three-necked flask, 4-tert-butylaniline (29.8 g, 0.2 mol) and 6 mol / L hydrochloric acid (100 mL) were added, and crotonaldehyde (15.4 g, 0.22 mol) was added dropwise under reflux, and reflux was continued for another 2 hours. Reflux was stopped, and zinc chloride (27.2 g, 0.2 mol) was added while still hot, and the mixture was stirred overnight at room temperature. The supernatant was removed, and isopropanol was added to the yellow syrup-like residue and refluxed for 2 hours. The mixture was cooled to 70°C, petroleum ether (200 mL) was added, and the precipitated crystals were filtered, washed with diethyl ether, and dried to obtain a zinc complex. This zinc complex was added to a mixture of water / ammonia (120 mL / 60 mL) and extracted three times with diethyl ether (80 mL). The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a yellow liquid of 6-tert-butyl-2-methyl-quinoline (2-1) (yield 16.2 g, yield 41%).

[0215] Next, compound (2-1) (16.0 g, 80 mmol) and chloroform (50 mL) were placed in a 200 mL two-necked flask and stirred. Trichloroisocyanuric acid (6.52 g, 28 mmol) was added in portions. After refluxing the mixture for 1 hour, the precipitated solid was filtered and washed with chloroform. The resulting organic layer was extracted three times with 1 mol / L sulfuric acid. The aqueous layers were combined, the pH was adjusted to 3 with aqueous sodium carbonate solution, and the mixture was extracted three times with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated to obtain pale yellow crystals of 2-chloromethyl-6-tert-butyl-quinoline (2-2) (yield 4.8 g, yield 25.7%).

[0216] Furthermore, compound (2-2) (4.7 g, 20 mmol), sodium cyanide (1.47 g, 30 mmol), a small amount of sodium iodide, and DMF (50 mL) were placed in a 100 mL three-necked flask and reacted at 60 °C for 2 hours. After cooling the reaction mixture, it was extracted with water (200 mL) / ethyl acetate (300 mL), and the resulting ethyl acetate layer was further washed with water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized with petroleum ether to obtain white crystals of 2-(6-tert-butylquinoline-2-yl)acetonitrile (2-3) (yield 1.9 g, yield 42.4%).

[0217] Next, under an argon stream, compounds (1-2) (2.18 g, 4.0 mmol), (2-3) (1.9 g, 8.5 mmol), and anhydrous toluene (68 mL) used in the synthesis of dye 1 were added to a 200 mL three-necked flask and heated under reflux. Under reflux, phosphorus oxychloride (2.62 mL, 28 mmol) was added dropwise with a syringe, and the mixture was heated under reflux for a further 2 hours. After the reaction was complete, while cooling with ice, dichloromethane (40 mL) and saturated sodium bicarbonate aqueous solution (40 mL) were added, and the mixture was extracted with dichloromethane. The organic layer was treated with anhydrous magnesium sulfate, and after filtering off the magnesium sulfate, the solvent was removed under reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: hexane / ethyl acetate) to roughly remove impurities. The residue obtained by distilling off the solvent was purified again by silica gel column chromatography (eluent: hexane / dichloromethane) to obtain the green solid precursor (2-4) (yield: 1.84 g, yield: 48%).

[0218] Finally, under an argon stream, precursor (2-4) (1.72 g, 1.8 mmol), toluene (45 mL), triethylamine (4.35 mL, 31.4 mmol), and boron trifluoride diethyl ether complex (7.88 mL, 62.7 mmol) were added to a 200 mL three-necked flask and heated under reflux for 1 hour. The reaction mixture was cooled on ice, and the precipitated solid was filtered off. The solid was then washed with water, saturated sodium bicarbonate aqueous solution, 50% methanol aqueous solution, and methanol, and dried under reduced pressure. The resulting residue was dissolved in toluene, methanol was added, and precipitation was performed to obtain a dark green solid of dye 2 (yield: 1.10 g, yield: 58%).

[0219] Dye 3 (compound of the above chemical formula 6-11-1)

[0220] [ka]

[0221] <Synthesis of pigment 3> For dye 3, precursors 2-4, which were used in the synthesis of dye 2, were used. Under an argon stream, precursors (2-4) (630 mg, 0.65 mmol), N,N-diisopropylethylamine (258 mg, 2.0 mmol), and dichloromethane (20 mL) were placed in a 100 mL two-necked flask, and chlorodiphenylborane (600 mg, 3.0 mmol) was added under reflux, and the reaction was carried out overnight. After washing the reaction mixture with water, the organic layer was dried over anhydrous magnesium sulfate and concentrated. After washing the residue with methanol, it was purified by column chromatography (eluent: dichloromethane / ethyl acetate = 100 / 10) to obtain the brown solid of dye 3 (yield: 186 mg, yield: 22%).

[0222] (Manufacturing Examples 1-9) Preparation of resin compositions for dispersed phases The near-infrared fluorescent material (A) and thermoplastic resin (B) were pre-mixed in a tumbler in the proportions listed in Table 1 below, and then melt-kneaded in a 30 mmφ twin-screw vented extruder at the set temperature listed in Table 1. After the resulting mixture was cooled, it was pelletized using a pelletizer to produce pellets for Production Examples 1-8 (pellets (1)-(8)).

[0223] The following thermoplastic resin (B) was used. Also, the values ​​in Table 1 are based on parts by mass: • B1: Polycarbonate resin (manufactured by Sumika Polycarbonate Co., Ltd., SD Polycarbonate (trademark) 301-4) • B2: Polymethyl methacrylate (PMMA) resin (manufactured by Mitsubishi Chemical Corporation, Acrypet® VH001) B3: Polystyrene resin (manufactured by DIC Corporation, DIC Styrene CR-4500) • B4: Polypropylene resin (manufactured by Prime Polymer Co., Ltd., Prime PolyPro® J106G)

[0224] • Grinding of resin compositions for dispersed phases Next, the pellets (1) to (8) obtained above were pulverized using a JFC-2000 cryogenic pulverizer manufactured by Nippon Analytical Industry Co., Ltd. Specifically, the pellets and tungsten steel balls were placed in a stainless steel container, the lid was closed, and cryogenic pulverization was performed under the conditions of pre-cooling with liquid nitrogen for 10 minutes, pulverization time for 15 minutes, and reciprocating motion rate of 1200 times / minute to obtain powder. Next, the powder was dispersed in ethanol, and the resulting dispersion was pressure filtered using a filter with a fixed capture particle size (300 μm) to obtain powders (1) to (8) having the average particle size listed in Table 1.

[0225] Separately, pellet (1) was freeze-milled using a similar cryogenic pulverizer under the conditions of pre-cooling with liquid nitrogen for 5 minutes, pulverization time for 8 minutes, and reciprocating speed of 1200 cycles / minute to obtain powder. Next, the powder was dispersed in ethanol, and the resulting dispersion was pressure-filtered using a filter with a fixed capture particle size (500 μm) to obtain powder (9) having the average particle size listed in Table 1. The maximum particle size of powder (9) measured by the method described below (Measurement of average particle size of pulverized material) was 324 μm.

[0226] (Measurement of average particle size of crushed material) The volume-average particle size of the obtained powder was determined using an image analysis particle size distribution analyzer (JASCO International Co., Ltd.: IF-3200) with Solmix® A-7 (manufactured by Nippon Alcohol Sales Co., Ltd.). For powder (9), the maximum particle size (cumulative 100%) was also determined.

[0227] (Emission evaluation) The luminescence of the obtained powders (1) to (9) was evaluated using the following method.

[0228] Camera: Omron Sentec Corporation, STC-MBCM200U3V-NIR Light source unit: Manufactured by Rebox Co., Ltd., with a lamp emitting wavelengths of 720-850nm mounted on an SPL-CC substrate. The distance between the light source and the sample (0.5 g of powder placed flat on a 52 x 76 mm glass plate) was set to 20 cm. The sample was placed horizontally, and the camera was positioned vertically at a distance of 30 cm from the sample. The camera's imaging condition was then visually evaluated based on the following criteria: A...Very clear B...Clear C...Luminous confirmation ×...Luminescence not confirmed (did not emit light).

[0229] The composition and evaluation results of powders (1) to (9) are shown in Table 1 below. A blank space in Table 1 indicates that the material was not used.

[0230] [Table 1]

[0231] (Example 1: Production Example 1 (dye-encapsulated PC) Island and polyamide sea MB and sheet) 60 parts by mass of the powder (1) obtained in Production Example 1 and 40 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 220°C), and subsequently pelletized to produce masterbatch (1).

[0232] 33.4 parts by mass of masterbatch (1) and 66.6 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 220°C) to produce a sheet sample (1) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0233] (Example 2: Islands and cross-linked polyethylene MB and sheets of Production Example 1 (dye-encapsulated PC) and seas of cross-linked polyethylene) 60 parts by mass of the powder (1) obtained in Production Example 1 and 40 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.) were stirred and mixed in a tumbler. The mixture was then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 140°C) to form pellets and produce a masterbatch (2).

[0234] 33.4 parts by mass of masterbatch (2), 64.6 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.), and 2 parts by mass of crosslinking agent (Perhexa® 25B-40, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, manufactured by NOF Corporation) were blended in a tumbler. The blend was then kneaded with two rolls at 125°C, and the mixture was heated and pressed at 200°C for 2 minutes at 10 MPa to produce a sheet sample (2) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0235] (Example 3: (Island of Production Example 2 (Dye-encapsulated PMMA) and Sea of ​​Cross-linked Polyethylene) 60 parts by mass of the powder (2) obtained in Production Example 2 and 40 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.) were stirred and mixed in a tumbler, and then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 140°C) to form pellets and produce a masterbatch (3).

[0236] After blending 33.4 parts by mass of masterbatch (3) and 64.6 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.) in a tumbler, the blend was kneaded with two rolls at a 125°C environment, and then heated and pressed at 200°C for 2 minutes at 10 MPa to produce a sheet sample (3) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0237] (Example 4: MB and sheet of island and cross-linked polyethylene sea of ​​Production Example 3 (dye-encapsulated PS)) 60 parts by mass of the powder (3) obtained in Production Example 3 and 40 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.) were stirred and mixed in a tumbler. The mixture was then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 140°C) to form pellets and produce a masterbatch (4).

[0238] 33.4 parts by mass of masterbatch (4), 64.6 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.), and 2 parts by mass of crosslinking agent (Perhexa® 25B-40, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, manufactured by NOF Corporation) were blended in a tumbler. The blend was then kneaded with two rolls at 125°C, and heated and pressed at 200°C for 2 minutes at 10 MPa to produce a sheet sample (4) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0239] (Example 5: Island and epoxy resin sea of ​​Production Example 1 (pigment-encapsulated PC)) 60 parts by mass of the powder (1) obtained in Production Example 1 and 40 parts by mass of the epoxy resin composition (DIC Corporation, Epiclon® 850) were stirred and mixed in a stirrer, and then degassed under reduced pressure to obtain a masterbatch (5).

[0240] Next, 33.4 parts by mass of the obtained masterbatch (5) was mixed with 66.6 parts by mass of epoxy resin composition (100 parts by mass of Epiclon® 850, manufactured by DIC Corporation, and 90 parts by mass of curing agent (Epiclon® B-5001, manufactured by DIC Corporation)) using a stirrer. After stirring and mixing, degassing was performed under reduced pressure to obtain resin composition (5). Next, the obtained resin composition (5) was injected into a mold and then heated and cured at 120°C for 1 hour to produce a sheet sample (5) with a length of 127 mm, a width of 12.7 mm, and a thickness of 1 mm.

[0241] (Example 6: MB and sheet of island and sea of ​​polyethylene resin from Manufacturing Example 4 (dye-encapsulated PP)) 60 parts by mass of the powder (4) obtained in Production Example 4 and 40 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.) as resin (C) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 140°C), and subsequently pelletized to produce a masterbatch (6).

[0242] 33.4 parts by mass of masterbatch (6) and 66.6 parts by mass of polyethylene resin (Novatec® LL UJ580, linear low-density polyethylene, manufactured by Nippon Polyethylene Co., Ltd.) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 140°C) to produce a sheet sample (6) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0243] (Example 7: MB and sheet of the island and sea of ​​TPU resin from Manufacturing Example 1 (dye-encapsulated PC)) 60 parts by mass of powder (1) obtained in Production Example 1 and 40 parts by mass of thermoplastic polyurethane resin (Tecoflex EG65D, manufactured by Lubrizol) as resin (C) were stirred and mixed in a tumbler. Then, the mixture was melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 190°C), and subsequently pelletized to produce a masterbatch (7).

[0244] 33.4 parts by mass of masterbatch (7) and 66.6 parts by mass of thermoplastic polyurethane resin (Tecoflex EG65D, manufactured by Lubrizol) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 200°C) to produce a sheet sample (7) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0245] (Example 8: Island and polyamide sea MB and sheet of Production Example 5 (dye-encapsulated PC)) 60 parts by mass of the powder (5) obtained in Production Example 5 and 40 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 200°C), and subsequently pelletized to produce a masterbatch (8).

[0246] 33.4 parts by mass of masterbatch (8) and 66.6 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 220°C) to produce a sheet sample (8) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0247] (Example 9: MB and sheet of the island and polyamide sea of ​​Production Example 6 (dye-encapsulated PC)) 60 parts by mass of the powder (6) obtained in Production Example 6 and 40 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 200°C), and subsequently pelletized to produce a masterbatch (9).

[0248] After blending 33.4 parts by mass of masterbatch (9) and 66.6 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) in a tumbler, the blend was melt-molded in an extruder equipped with a T-die (set temperature 220°C) to produce a sheet sample (9) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0249] (Example 10: Island and polyamide sea MB and sheet of manufacturing example 7 (dye-encapsulated PC)) 60 parts by mass of the powder (7) obtained in Production Example 7 and 40 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 200°C), and subsequently pelletized to produce a masterbatch (10).

[0250] 33.4 parts by mass of masterbatch (10) and 66.6 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 220°C) to produce a sheet sample (10) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0251] (Example 11: Island and polyamide sea MB and sheet of Production Example 8 (dye-encapsulated PC)) 60 parts by mass of the powder (8) obtained in Production Example 8 and 40 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 200°C), and subsequently pelletized to produce a masterbatch (11).

[0252] 33.4 parts by mass of masterbatch (11) and 66.6 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 220°C) to produce a sheet sample (11) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0253] (Example 12: Island and polyamide sea MB and sheet of manufacturing example 9 (dye-encapsulated PC coarse material)) 60 parts by mass of the powder (9) obtained in Production Example 9 and 40 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were stirred and mixed in a tumbler, then melt-kneaded in a 30 mmφ twin-screw vented extruder (set temperature 200°C), and subsequently pelletized to produce a masterbatch (12).

[0254] 33.4 parts by mass of masterbatch (12) and 66.6 parts by mass of polyamide resin (Arkema, PEBAX® 4033SA01) were blended in a tumbler. The blend was then melt-molded in an extruder equipped with a T-die (set temperature 220°C) to produce a sheet sample (12) measuring 127 mm in length, 12.7 mm in width, and 1 mm in thickness.

[0255] [evaluation] (Diameter of the dispersed phase) The average diameter of the dispersed phase in the obtained sheet samples (1) to (12) was evaluated by the following method.

[0256] Specifically, sheet samples (1) to (12) were cut perpendicular to the surface, the exposed cut surfaces were polished to make them smooth, and then observed and images were taken using a digital microscope (Keyence Corporation: VHX-7000). Next, 50 arbitrary, non-overlapping dispersed phases (island portions of a sea-island structure) were selected at a magnification of 200x, measured as equivalent diameters, and their particle size distribution was determined. The average diameter was calculated as the number average.

[0257] (Luminous efficiency) The luminescence efficiency of the obtained sheet samples (1) to (12) was evaluated by the following method: Camera: STC-MBCM200U3V-NIR, manufactured by Sentec Corporation. Light source unit: Manufactured by Rebox Co., Ltd., with a 720-850nm lamp mounted on an SPL-CC substrate in a darkroom. The distance between the light source and the sheet sample was set to 20 cm. The sheet sample was placed horizontally, and the sample was positioned 30 cm from a vertically positioned camera. Images were then captured by the camera (see Figure 1). The obtained images were processed using the image processing software "Image" and evaluated in 256 steps from 0 to 255. No light emission was represented as step 0, and the highest step number in the image was considered the luminescence efficiency of the sheet. A higher step number indicates higher luminescence efficiency.

[0258] The evaluation results are shown in Table 2 below.

[0259] [Table 2]

[0260] As is clear from Table 2 above, the resin compositions of Examples 1 to 12 were found to exhibit excellent luminescence efficiency. [Explanation of Symbols]

[0261] 1 camera, 2 analysis device, 3 light source units, 4. Sample (sheet sample).

Claims

1. The material comprises a near-infrared fluorescent material (A), a thermoplastic resin other than a polyamide resin (B), and a resin (C) different from the thermoplastic resin (B). A masterbatch in which the resin (C) forms a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase, The near-infrared fluorescent material (A) is The following general formula (II 1) 【Chemistry 1】 [In formula (II 1 ), Ra and Rb, together with the nitrogen atom to which Ra is bonded and the carbon atom to which Rb is bonded, form an aromatic five-membered ring, an aromatic six-membered ring, or a condensed aromatic ring formed by the condensation of two or three five-membered or six-membered rings; R c and R d, together with the nitrogen atom to which R c is bonded and the carbon atom to which R d is bonded, form an aromatic five-membered ring, an aromatic six-membered ring, or a condensed aromatic ring formed by the condensation of two or three five-membered or six-membered rings; Re and Rf independently represent a halogen atom or an oxygen atom; R g represents a hydrogen atom or an electron-withdrawing group. However, if Re and Rf are oxygen atoms, Re, the boron atom bonded to Re, Ra, and the nitrogen atom bonded to Ra may all form a ring, and Rf, the boron atom bonded to Rf, Rc, and the nitrogen atom bonded to Rc may all form a ring. If Re is an oxygen atom and does not form a ring, then Re is a substituted oxygen atom, and if Rf is an oxygen atom and does not form a ring, then Rf is a substituted oxygen atom. The following general formula (II 2) 【Chemistry 2】 Compounds represented by [Formula (II 2), where Ra a to R f are the same as in Formula (II 1)] The following general formula (II 3) 【Transformation 3】 [In formula (II 3 ), Rh and Ri, together with the nitrogen atom to which Rh is bonded and the carbon atom to which Ri is bonded, form an aromatic five-membered ring, an aromatic six-membered ring, or a condensed aromatic ring formed by the condensation of two or three five-membered or six-membered rings; R j and R k, together with the nitrogen atom to which R j is bonded and the carbon atom to which R k is bonded, form an aromatic five-membered ring, an aromatic six-membered ring, or a condensed aromatic ring formed by the condensation of two or three five-membered or six-membered rings; R l, R m, R n, and R o independently represent a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group; R p and R q independently represent a hydrogen atom, a halogen atom, a C1-20 alkyl group, a C1-20 alkoxy group, an aryl group, or a heteroaryl group; R r and R s independently represent a hydrogen atom or an electron-withdrawing group. [The compound represented by...] Furthermore, the following general formula (II 4) 【Chemistry 4】 [In formula (II 4), R h to R q are the same as in formula (II 3).] At least one compound selected from the group consisting of compounds represented by: A masterbatch with a maximum fluorescence wavelength of 650 nm or higher.

2. The near-infrared fluorescent material (A) is The following general formula (II ３ -1) to (II ３ -6) 【Transformation 5】 [Formula (II)] ３ -1) Middle R ２３ 、R ２４ 、R ２５ 、and R ２６ are, independently of one another, a halogen atom, C １－２０ alkyl group, C １－２０ alkoxy group, aryl group, or heteroaryl group; R ２７ and R ２８ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Represents an alkoxy group, aryl group, or heteroaryl group; R ２９ and R ３０ These independently represent a hydrogen atom or an electron-withdrawing group; Y ９ and Y １０ These represent, independently of each other, a sulfur atom, an oxygen atom, a nitrogen atom, or a phosphorus atom; R ３１ and R ３２ teeth, (p4) Independently of each other, hydrogen atoms, halogen atoms, C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group, (p5) R ３１ and R ３２ Both form an optionally substituted aromatic five-membered ring or an optionally substituted aromatic six-membered ring; R ３３ and R ３４ teeth, (q4) Independently of each other, hydrogen atoms, halogen atoms, C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group, (q5)R ３３ and R ３４ Both form an aromatic five-membered ring or an aromatic six-membered ring, which may have substituents. 【Transformation 6】 [Formula (II ３ -2) ~ (II ３ -6) Medium, R ２３ ~R ３０ is the above formula (II ３ -1) is the same as; X １ and X ２ These represent, independently of each other, a nitrogen atom or a phosphorus atom; R ３５ , R ３６ , R ３７ , and R ３８ teeth, (p6) Independently of each other, hydrogen atoms, halogen atoms, C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group. (p7) R ３５ and R ３６ Both form an aromatic five-membered ring or an aromatic six-membered ring which may have substituents, R ３７ and R ３８ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group. (p8) R ３６ and R ３７ Both form an aromatic five-membered ring or an aromatic six-membered ring which may have substituents, R ３５ and R ３８ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group, (p9) R ３７ and R ３８ Both form an aromatic five-membered ring or an aromatic six-membered ring which may have substituents, R ３５ and R ３６ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Represents an alkoxy group, aryl group, or heteroaryl group; R ３９ , R ４０ , R ４１ , and R ４２ teeth, (q6) Independently of each other, hydrogen atoms, halogen atoms, C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group. (q7)R ３９ and R ４０ Both form an aromatic five-membered ring or an aromatic six-membered ring which may have substituents, R ４１ and R ４２ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group. (q8)R ４０ and R ４１ Both form an aromatic five-membered ring or an aromatic six-membered ring which may have substituents, R ３９ and R ４２ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Represents an alkoxy group, an aryl group, or a heteroaryl group, (x9)R ４１ and R ４２ Both form an aromatic five-membered ring or an aromatic six-membered ring which may have substituents, R ３９ and R ４０ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ Compounds represented by any of the following general formulas (II) represent an alkoxy group, an aryl group, or a heteroaryl group, as well as compounds represented by the following general formula (II) ４ -1) to (II ４ -6) 【Transformation 7】 [In formula (II ４ -1) to (II ４ -6), R ２３ to R ２８ is the same as the said formula (II ３ -1). In formula (II ４ -1), R ３１ to R ３４ , Y ９ , and Y １０ are the same as the said formula (II ３ -1), and in formula (II ４ -2) to (II ４ [[ID=2​​​​​​​​​​​​​​​​

3. The near-infrared fluorescent material (A) is The following general formula (II ３ -7) ~ (II ３ -9) and (II ４ -7) ~ (II ４ -9) 【Transformation 8】 [In the formula, Y ２３ and Y ２４ Each represents a carbon atom or a nitrogen atom independently of the other; Y １３ and Y １４ These represent, independently of each other, an oxygen atom or a sulfur atom; Y ２５ and Y ２６ Each represents a carbon atom or a nitrogen atom independently of the other; R ４７ and R ４８ These independently represent a hydrogen atom or an electron-withdrawing group; R ４３ , R ４４ , R ４５ , and R ４６ Each represents independently of the other an aryl group which may have a halogen atom or substituent; P １５ and P １６ These are, independently of each other, halogen atoms, C 1-20 alkyl group, C 1-20 This represents alkoxy groups, amino groups, monoalkylamino groups, and dialkylamino groups; n15 and n16 represent integers between 0 and 3, independently of each other; A １５ and A １６ These are, independently of each other, hydrogen atoms, halogen atoms, and C １－２０ alkyl group, C １－２０ This represents a phenyl group which may have one to three substituents selected from the group consisting of alkoxy groups, amino groups, monoalkylamino groups, and dialkylamino groups. The masterbatch according to claim 2, comprising at least one compound selected from the group consisting of compounds represented by any of the following.

4. The masterbatch according to claim 1 or 2, wherein the content of the near-infrared fluorescent material (A) relative to 100% by mass of the total of the near-infrared fluorescent material (A) and the thermoplastic resin (B) other than the polyamide resin is 0.001% by mass or more and 0.5% by mass or less.

5. A near-infrared fluorescent material (A), a thermoplastic resin other than a polyamide resin (B), and a resin (C) different from the thermoplastic resin (B), A masterbatch in which the resin (C) forms a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase, A masterbatch in which the content of the near-infrared fluorescent material (A) is 0.001% by mass or more and 0.5% by mass or less, relative to 100% by mass of the total of the near-infrared fluorescent material (A) and the thermoplastic resin (B) other than the polyamide resin.

6. The masterbatch according to claim 1 or 5, wherein the thermoplastic resin (B) other than the polyamide resin comprises at least one selected from the group consisting of thermoplastic polyurethane (TPU) resin, polycarbonate (PC) resin, vinyl chloride resin, acrylic resin, polyester resin, polystyrene resin, olefin resin, and polyacetal (POM) resin.

7. The masterbatch according to claim 1 or 5, wherein the resin (C) comprises at least one selected from the group consisting of polyamide resin, polyethylene resin, polypropylene resin, and thermosetting resin.

8. The masterbatch according to claim 1 or 5, wherein the resin (C) comprises a polyamide resin.

9. The masterbatch according to claim 1 or 5, wherein the resin (C) comprises a thermosetting resin.

10. The masterbatch according to claim 1 or 5, wherein the total content of the near-infrared fluorescent material (A) and the thermoplastic resin (B) is in the range of 20% by mass or more and 80% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), the thermoplastic resin (B), and the resin (C).

11. The process comprises the steps of: melting and kneading a near-infrared fluorescent material (A) and a thermoplastic resin other than a polyamide resin (B) to obtain a kneaded product; pulverizing the kneaded product obtained in the first step to obtain particles containing powdered near-infrared fluorescent material (A) and thermoplastic resin (B); and mixing or kneading the particles obtained in the first step with a resin (C). A method for manufacturing a masterbatch in which the resin (C) forms a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase.

12. The process comprises adding a diluent resin (D) to the masterbatch according to claim 1 or 5, and then mixing or kneading it. The material comprises a near-infrared fluorescent material (A), a thermoplastic resin other than polyamide resin (B), a resin different from the thermoplastic resin (B) (C), and a resin different from the thermoplastic resin (B) (D). A method for producing a resin composition, wherein the resins (C) and (D) form a continuous phase, and a dispersed phase containing the near-infrared fluorescent material (A) and the thermoplastic resin (B) is formed in the continuous phase.

13. The method for producing the resin composition according to claim 12, wherein the resin (D) comprises at least one selected from the group consisting of polyamide resin, polyethylene resin, polypropylene resin, thermosetting resin, and crosslinked polyethylene resin.

14. A method for producing a resin composition according to claim 12, wherein the content of the resin (D) is in the range of 20% by mass or more and 80% by mass or less, based on 100% by mass of the total of the near-infrared fluorescent material (A), the thermoplastic resin (B), the resin (C), and the resin (D).

15. A method for producing the resin composition according to claim 12, wherein the resin composition is used as a medical material.

16. A method for producing the resin composition according to claim 12, wherein at least a portion of the resin composition is used as a material for a medical device used in the body of a patient.

17. A method for manufacturing a molded article, comprising the step of melt-molding a resin composition obtained by the manufacturing method of claim 12.

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