Compound

Abstract

To provide a new compound that can be used as a ligand of a metal-complex compound.SOLUTION: The present invention provides a compound represented by formula (III) [where X11 and X12 independently represent an aromatic group or the like, and Z1 represents a 2,6-dioxo-1,2,5,6-tetrahydropyridine group substituted with a dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborine structure-containing group or a dimethylindolin-2-ylideneethylidene group.SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a compound.

Background Art

[0002] Metal complex compounds such as rare earth complexes have been studied for use in various applications such as luminescent materials (for example, Patent Documents 1 to 3). Metal complex compounds are usually used together with ligands.

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0004] One aspect of the present invention aims to provide a new compound that can be used as a ligand for a metal complex compound.

Means for Solving the Problems

[0005] One aspect of the present invention relates to a compound represented by the following formula (III).

Chemical Formula

Chemical formula

Chemical formula

[0006] In the above compound, Z 1 may be a group represented by the following formula (Ib) or (IIb).

Chemical formula

Chemical formula

[0007] Another aspect of the present invention relates to a metal complex containing a metal ion and the above compound coordinated to the metal ion.

[0008] Another aspect of the present invention relates to a compound represented by the following formula (3).

Chemical formula

[0009] According to one aspect of the present invention, a new compound that can be used as a ligand of a metal complex compound can be provided. The compound according to one aspect of the present invention exhibits fluorescence emission and can form a complex compound that is colored with visible light in a solid or in a solution. [Brief Description of the Drawings]

[0010]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Mode for Carrying Out the Invention

[0011] Hereinafter, embodiments of the present invention will be described. However, the present invention is not limited to the following embodiments.

[0012] One embodiment of the present invention is a compound represented by the following formula (III).

Chemical formula

[0013] In the formula, X 11 and X 12 each independently represents an aromatic group, a heteroaromatic group, a C 1~12 alkyl group, a C 3~12 alkenyl group, a C 3~12 cycloalkyl group, a C 3~12 cycloalkenyl group, a C 3~12 alkynyl group, an aromatic oxy group, a heteroaromatic oxy group, a C 1~12 alkyloxy group, a C 3~12 alkenyloxy group, a C 3~12 cycloalkyloxy group, a C 3~12 cycloalkenyloxy group, or a C 3~12 alkynyl oxy group.

[0014] The aromatic group may be a phenyl group, a naphthyl group, a biphenyl group, etc. The heteroaromatic group may be a pyrrolyl group, a furaryl group, an indolyl group, a thienyl group, etc. At least a part of the hydrogen atoms bonded thereto may be substituted with other groups, for example, at least one substituent selected from the group consisting of a hydroxy group, a nitro group, an amino group, a sulfo group, a cyano group, a silyl group, a phosphonic acid group, a diazo group, a mercapto group, and a halogen atom.

[0015] C 1~12 The alkyl group is an alkyl group having 1 to 12 carbon atoms. C 1~12 The alkyl group (C n H 2n+1 : n = 1 to 12) may have a straight chain or a branch. C 1~12 At least one hydrogen atom of the alkyl group may or may not be substituted with another group. The C having a substituent 1~12 The alkyl group is, for example, a perfluoroalkyl group (C n F 2n+1 : n = 1 to 12) and a perchloroalkyl group (C n Cl 2n+1 : n = 1 to 12), etc., which may be a perhalogenated alkyl group having a straight chain or a branch. The alkyl group having a substituent includes, for example, an aralkyl group such as a benzyl group and a phenethyl group, and a perhalogenated aralkyl group such as a perfluorobenzyl group. 1~12

[0016] C 3~12 The alkenyl group is an alkenyl group having 3 to 12 carbon atoms. C 3~12 The alkenyl group may have a straight chain or a branch. C 3~12 Examples of the alkenyl group include an allyl group and a butenyl group. C 3~12 At least one hydrogen atom of the alkenyl group may or may not be substituted with another group. The C having a substituent 3~12 The alkenyl group having a substituent is, for example, a perfluoroalkenyl group such as a perfluorovinyl group, a perfluoroallyl group and a perfluorobutenyl group, and a perchloroalkenyl group, etc., which have a straight chain or a branch 3~12 perhalogenated alkenyl group.

[0017] C 3~12 The cycloalkyl group is a cycloalkyl group having 3 to 12 carbon atoms. C 3~12 The alkenyl group may have a straight chain or a branch. C 3~12 ​At least one hydrogen atom of the cycloalkyl group may or may not be substituted with another group. The C with a substituent 3~12 The cycloalkyl group is, for example, a perfluorocycloalkyl group (C n F 2n-1 : n = 3 to 12) and a perchlorocycloalkyl group (C n Cl 2n-1 : n = 3 to 12), etc. C 3~12 Perhalogenated cycloalkyl groups are exemplified.

[0018] C 3~12 The cycloalkenyl group is a cycloalkenyl group having 3 to 50 carbon atoms. C 3~12 Examples of the cycloalkenyl group include a cyclopentenyl group and a cyclohexenyl group. C 3~12 At least one hydrogen atom of the cycloalkenyl group may or may not be substituted with another group. The C with a substituent 3~12 The cycloalkenyl group may be, for example, a perfluorocycloalkenyl group or a perchlorocycloalkenyl group, etc. C 3~12 Perhalogenated cycloalkenyl group.

[0019] C 3~12 The alkynyl group is an alkynyl group having 3 to 12 carbon atoms. C 3~12 At least one hydrogen atom of the alkynyl group may or may not be substituted with another group.

[0020] The aromatic oxy group is a group in which the above aromatic group and an oxy group (-O-) are bonded. The heteroaromatic oxy group is a group in which the above heteroaromatic group and an oxy group are bonded. C 1~12 The alkyloxy group is a group in which the above C 1~12 Alkyl group and an oxy group are bonded. C 3~12 The alkenyloxy group is a group in which the above C 3~12 Alkenyl group and an oxy group are bonded. C 3~12 The cycloalkyloxy group is a group in which the above C 3~12 Cycloalkyl group and an oxy group are bonded. C3~12 The cycloalkenyloxy group is a group in which the above cycloalkenyl group and oxy group are bonded. C 3~12 The alkynyloxy group of C 3~12 is a group in which the above alkynyl group of C 3~12 and the oxy group are bonded.

[0021] X 11 and X 12 The above groups represented by may have one or more -COO- and -CO- inserted between the C-C single bonds at any position thereof.

[0022] X 11 and X 12 may each independently be an aromatic group and may be a phenyl group.

[0023] Z 1 may be a group represented by the following formula (I).

Chemical formula

[0024] In formula (I), * represents a bond. n and m each independently represent an integer from 0 to 3. n and m may each independently be 0 to 2, 0 to 1, or 0.

[0025] R 11 and R 12 each independently represent a monovalent organic group containing a second bonding group, an alkyl group, a cyano group, a hydroxy group, or a halogen atom. The second bonding group may be at least one selected from the group consisting of a carbonyl group (-C(=O)-), an ester group (-COO-), an amide group (-NH-C(=O)-), an ether group (-O-), and a thioether group (-S-). R 11 and R 12The number of carbon atoms of the alkyl group represented by [alkyl group] may be, for example, 1 to 20, 1 to 15, 1 to 10, or 1 to 6. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. The halogen atom may be, for example, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. When m is 2 or more, a plurality of Rs 11 may be the same or different, and when n is 2 or more, a plurality of Rs 12 may be the same or different.

[0026] L 1 represents a divalent organic group containing a first linking group, an alkylene group, or a phenylene group. The first linking group may be at least one selected from the group consisting of a carbonyl group (-C(=O)-), an ester group (-COO-), an amide group (-NH-C(=O)-), an ether group (-O-), and a thioether group (-S-). L 1 may be, for example, an alkylene group containing a first linking group, an arylene group containing a first linking group (for example, a phenylene group), or a group consisting of a first linking group, an alkylene group, and an arylene group. The group represented by formula (I) may be bonded to a ligand via an ether group (-O-) or a thioether group (-S-).

[0027] The group represented by formula (I) may be, for example, a group represented by the following formula (Ia). In this case, a complex compound that exhibits more excellent fluorescence emission properties and is colored with visible light in a solid or solution can be formed. [Chemical formula]

[0028] In formula (Ia), m, n, R 11 , R 12 and * have the same meanings as described above. o represents an integer of 0 to 4. o may be 0 to 3, 0 to 2, 0 to 1, or 0. R 13represents a monovalent organic group containing a fourth linking group, an alkyl group, a cyano group, a hydroxy group, a nitro group, a sulfo group, an amino group, a silyl group, a phosphonic acid group, a diazo group, a mercapto group, or a halogen atom. The fourth linking group may be at least one selected from the group consisting of a carbonyl group, an ester group, an amide group, an ether group, and a thioether group. R 13 Specific examples of 11 and R 12 may be the same as those described above.

[0029] L 2 represents an alkylene group or an arylene group. The number of carbon atoms of the alkylene group represented by L 2 may be, for example, 1 to 20, 1 to 15, 1 to 10, or 1 to 6. The alkylene group represented by L 2 may be, for example, a methylene group (-CH2-), an ethylene group, a propylene group, a butylene group, a pentylene group, or a hexylene group. The arylene group represented by L 2 may be, for example, a phenylene group (-C6H4-), a naphthylene group (-C 10 H6-).

[0030] The group represented by formula (I) may be a group represented by the following formula (Ib) in which m, n, and o are 0 and L 2 is a methylene group.

Chemical formula

[0031] Z 1 may be a group represented by the following formula (II).

Chemical formula

[0032] In formula (II), p represents an integer from 0 to 4. p may be 0 to 3, 0 to 2, 0 to 1, or 0. * represents a bond.

[0033] R 21represents a monovalent organic group containing a third linking group, an alkyl group, a cyano group, a hydroxy group, a nitro group, an amino group, a sulfo group, a cyano group, a silyl group, a phosphonic acid group, a diazo group, a mercapto group, or a halogen atom. The third linking group is at least one selected from the group consisting of a carbonyl group, an ester group, an amide group, an ether group, and a thioether group. When p is 2 or more, a plurality of R 21 may be the same or different. The details of the substituent represented by R 21 may be the same as those of the substituents represented by R 11 and R 12 .

[0034] R 22 ~R 25 each independently represents a C 1-12 alkyl group. The C 22 ~R 25 alkyl group represented by is an alkyl group having 1 to 12 carbon atoms. R 1-12 ~R 22 ~R 25 may be, for example, a C 1-12 alkyl group having 1 to 12 carbon atoms, a C 1-6 alkyl group having 1 to 10 carbon atoms, or a C 1-6 alkyl group having 1 to 6 carbon atoms. The C 1-12 alkyl group may be, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

[0035] L 3 represents an alkylene group or an arylene group. The details of the alkylene group and arylene group represented by L 3 may be as described above.

[0036] The group represented by formula (II) may be a group represented by the following formula (IIa) in which p is 0, R 22 ~R 25 are methyl groups, and L 3 is an n-propylene group (-CH2-CH2-CH2-). In this case, a complex compound having better fluorescence emission properties and being colored with visible light in the solid state or in solution can be formed. [Chem.]

[0037] Specifically, the compound according to this embodiment may be a compound represented by the following formula (A-1) or (A-2). [Chem.] [Chem.]

[0038] Another embodiment of the present invention is a metal complex containing a metal ion and the above compound coordinated to the metal ion.

[0039] The metal ion may be a rare earth ion. Hereinafter, the rare earth complex, which is a metal complex when the metal ion is a rare earth ion, will be described in detail.

[0040] The rare earth ion is a divalent to tetravalent rare earth ion, and may be a divalent or trivalent rare earth ion. The rare earth ion may be, for example, an ion of a lanthanide series element such as La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and Lu. The rare earth ion may be an Eu ion or a Tb ion.

[0041] Among conventional rare earth complexes, some are excited by light in the ultraviolet region and exhibit fluorescence in the visible light region. However, usually these complexes do not show absorption in the visible light region that does not contain light in the ultraviolet region, so they are colorless or slightly yellowish. On the other hand, the rare earth complex according to this embodiment has absorption in the wavelength range of 400 to 600 nm also in the visible light region, so that the rare earth complex itself exhibits a distinct color in the visible light region. That is, it is possible to provide a rare earth complex colored in a wide wavelength region (wavelength range) from the ultraviolet region to the visible light region. This property is considered useful, for example, in applications as a dye for coloring a target substance. Here, the target substance may be either a liquid or a solid. When a rare earth complex that is excited only in the ultraviolet region and an organic dye having absorption in the visible region, at least two kinds of compounds are used in combination, there is a problem that it is difficult to ensure the dyeability to the target substance due to differences in solubility and the like. According to the rare earth complex according to the present embodiment, since the rare earth complex alone can impart coloring and fluorescence emission properties to the target substance, it is easy to maintain dyeability, and the functional imparting becomes simpler.

[0042] The rare earth complex according to the present embodiment may be, for example, a complex represented by the following formula (IV).

Chemical formula

[0043] In the formula, Ln represents a rare earth element, n1 represents an integer of 2 to 4, n2 represents an integer of 2 to 4, and n3 represents an integer of 1 to 2. Z 2 has the same meaning as Z in formula (III). That is, Z 1 represents a group represented by the above formula (I) or (II). 2

[0044] X 21 and X 22 each independently represents an aromatic group, a heteroaromatic group, a C 1~12 alkyl group, a C 3~12 alkenyl group, a C 3~12 cycloalkyl group, a C 3~12 cycloalkenyl group, a C 3~12 alkynyl group, an aromatic oxy group, a heteroaromatic oxy group, a C 1~12 alkyloxy group, a C 3~12 alkenyloxy group, a C 3~12 cycloalkyloxy group, a C 3~12 cycloalkenyloxy group, or a C 3~12 alkynyloxy group.

[0045] Y 1 and Y 2is, independently of each other, an aromatic group, a heteroaromatic group, a C 1~12 alkyl group, a C 3~12 alkenyl group, a C 3~12 cycloalkyl group, a C 3~12 cycloalkenyl group or a C 3~12 alkynyl group. Examples of the heteroaromatic group include a thiophenyl group and the like.

[0046] X 21 、X 22 、Y 1 and Y 2 represented by C 1~12 alkyl group, a C 3~12 alkenyl group, a C 3~12 cycloalkyl group, and a C 3~12 cycloalkenyl group may have some or all of the hydrogen atoms substituted with halogen atoms, for example, fluorine atoms or chlorine atoms.

[0047] X 21 、X 22 、Y 1 and Y 2 The specific examples of the substituents represented by may be as described above.

[0048] Y 3 represents a hydrogen atom or a deuterium atom.

[0049] [Method for producing rare earth complex] The rare earth complex can be produced by a method including a step of reacting a complex precursor containing a rare earth ion with the compound represented by the above formula (III) to coordinate the compound represented by the formula (III) to the rare earth ion. The reaction may be carried out while heating. Examples of specific reaction conditions may be as described in the examples below.

[0050] The compound represented by the above formula (III) can be produced according to a normal synthesis method. Examples of the synthesis method are shown in the examples below.

[0051] For example, the compound (Compound B) represented by the following formula (B) can be synthesized according to the following reaction scheme. [Chemical formula]

[0052] Compound B can be obtained by a method including a step of reacting compound (compound 1) represented by formula (1), ethyl cyanoacetate, compound (compound 2) represented by formula (2), and a base to obtain compound (compound 3) represented by formula (3), and a step of reacting compound 3, compound (compound 4) represented by formula (4), and acetic anhydride to obtain compound B.

[0053] In the formula, X 31 and X 32 have the same meanings as X 21 and X 22 in formula (IV). q has the same meaning as p in formula (II). R 31 ~R 35 have the same meanings as R 21 ~R 25 in formula (II). R 36 represents a hydrocarbon group such as an alkyl group. R 31 may be, for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, or a hexyl group.

[0054] Compound 1 can be produced according to a conventional synthesis method. Examples of the synthesis method of compound 1 are as described in the examples below.

[0055] The reaction for obtaining compound 3 is usually carried out in the presence of a base. The base may be, for example, piperidine, pyridine, triethylamine, and / or hexamethyleneimine. The reaction for obtaining compound 3 may be carried out in the presence of a solvent. Examples of the solvent include ethanol, dichloromethane, tetrachloroethane, carbon tetrachloride, diethyl ether, tetrahydrofuran, benzene, toluene, etc. The reaction for obtaining compound 3 may be carried out while heating. After the reaction is completed, post-treatment may be carried out by a conventional method. Specific examples of the reaction conditions are as described in the examples below.

[0056] Compound 3 is useful as a precursor compound of Compound B. Another embodiment of the present invention is a compound represented by formula (3). In the compound represented by formula (3), R 35 may be a C 1-10 alkyl group, may be a C 1-6 alkyl group, and may be a methyl group. L 4 may be an alkylene group, for example, an n-propylene group. The compound represented by formula (3) may specifically be a compound represented by the following formula (3-1). [Chemical formula]

[0057] [Resin composition] Another embodiment of the present invention is a resin composition containing the above rare earth complex and a resin.

[0058] Examples of the resin include polymethyl (meth) acrylate, polycarbonate, polystyrene, polyurethane, polycarbonate, polyester, polyether, polyamide, polyvinyl chloride, silicone, epoxy resin, fluororesin, polyethylene, polypropylene, etc. The resin may be a copolymer obtained by combining various monomers or a mixture of a plurality of resins.

[0059] The shape of the resin may be film-like, sheet-like, fibrous, woven fabric, paper, particulate, pellet-like, or liquid.

[0060] The rare earth complex can be incorporated into the resin composition by the following methods. For example, a method of impregnating and drying an object in the form of a film, fiber, or particle in a solution containing the rare earth complex, or a method of dissolving the rare earth complex and the resin in an organic solvent and applying and drying them on a substrate using various coating techniques, or a method of adding a dye solution to a resin fine particle dispersion and dyeing, or a method of directly adding the rare earth complex during the melt-kneading of resin pellets. A plurality of methods can be selected, such as these.

[0061] The content of the rare earth complex in the resin composition is appropriately selected according to the purpose of the resin composition. For example, the content of the rare earth complex in the resin composition may be 0.001 parts by mass or more, or 0.01 parts by mass or more, and may be 0.5 parts by mass or less, or 0.4 parts by mass or less, based on 1 part by mass of the resin.

[0062] The content of the resin may be appropriately adjusted according to the use, required properties, etc. of the resin composition. The content of the resin in the resin composition may be 50% by mass or more, or 60% by mass or more, and may be 99.9% by mass or less, or 99% by mass or less, based on the total mass of the resin composition.

[0063] The resin composition may contain inorganic substances inside and / or within the resin. Examples of the inorganic substances include ceramic fillers such as silica, alumina, silicon nitride, boron nitride, or metal particles such as iron, nickel, cobalt, etc.

[0064] The resin composition may further contain other components. Examples of the other components include additives such as antioxidants, ultraviolet absorbers, light stabilizers, flame retardants, lubricants, plasticizers, antistatic agents, thixotropic agents, surfactants, thickeners, inorganic fillers, pigments, etc.

[0065] The resin composition can be produced by a method including a step of mixing the resin and the rare earth complex.

[0066] The resin composition can be used, for example, in dyeing of plastic raw materials, coating and film-forming materials such as paints and printing inks, paint materials, writing instruments such as paints and pens, toys, resins for 3D printers, agricultural films, display plates for safety, disaster prevention, and crime prevention supplies, fluorescent labeling agents for biomolecules such as proteins and nucleic acids, labeling agents for immunoassay methods, etc.

Examples

[0067] Hereinafter, the present invention will be described in more detail based on examples, but the present invention is not limited to the following examples. In the following description, "TTA" is an abbreviation for tenoyltrifluoroacetone, and "TOPO" is an abbreviation for trioctylphosphine oxide.

[0068] <Synthesis of Ligand 1> Synthesis Example 1-1: Synthesis of (3-aminopropyl)diphenylphosphine oxide

Chemical Formula

[0069] 10 mL of dry benzene and 5 mL of chloroform were added to 3.8 mol of 3-chloropropylamine hydrochloride. Then, 8.3 mmol of triethylamine solution (dissolved in 3.3 mL of dry benzene and 1.7 mL of chloroform) was added. After stirring for 20 minutes, it was cooled to 2 - 4 °C, and 3.8 mmol of diphenylchlorophosphine solution (dissolved in 6.6 mL of dry benzene and 3.4 mL of chloroform) was added. After stirring for 1 hour, the temperature was raised to reflux and stirred for another 1 hour. The temperature was lowered to room temperature, and the solvent was distilled off. The residue was dissolved in 50 mL of chloroform and extracted with 100 mL of distilled water. The organic layer was removed, an aqueous sodium hydroxide solution was added until pH = 10, and then extracted with 100 mL of chloroform. Chloroform was distilled off to obtain the compound represented by the above formula (1-1) as the target product. The yield was 75%.

[0070] Synthesis Example 1-2: Synthesis of 1-(3-diphenylphosphoryl)propyl)-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Chemical Formula

[0071] 1 mmol of the compound represented by the above formula (1-1), 1 mmol of ethyl cyanoacetate, and 5 mL of ethanol were added, and the mixture was stirred at room temperature for 6 hours. Then, 1.1 mmol of ethyl acetoacetate and 0.1 mL of piperidine were added, and the mixture was stirred at 110 °C. After cooling to room temperature, the solvent was distilled off, and 10 mL of 10% hydrochloric acid was added. The resulting precipitate was collected by filtration, washed with distilled water and hexane, and dried to obtain the compound represented by the above formula (1-2) as the target product. The yield was 65%.

[0072] Synthesis Example 1-3: Synthesis of (Z)-5-(2-((E)-3,3-dimethylindolin-2-ylidene)ethylidene)-1-(3-(diphenylphosphoryl)propyl)-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile

Chemical formula

[0073] 1.05 mmol of 2-(1,3,3-trimethylindolin-2-ylidene)acetaldehyde and 3 mL of acetic anhydride were added to 1 mmol of the compound represented by the above formula (1-2), and the mixture was refluxed for 15 minutes. After the resulting precipitate was collected by filtration, it was washed with hexane and dried to obtain the compound represented by the above formula (1-3). The yield was 82%. 31 P-NMR: 32.4 ppm (solvent: chloroform)

[0074] The fact that the compound represented by the above formula (1-3) was obtained was confirmed by X-ray crystal structure analysis. The results of the X-ray crystal structure analysis are shown in Figure 1. The measurement was performed using D8 VENTURE, and the analysis was performed using VESTA.

[0075] <Synthesis of the rare earth complex of the example> Synthesis Example 1-4: Synthesis of the Eu complex of the example

Chemical formula

[0076] To 1 mmol of the compound represented by the above formula (1-3), 1 mmol of Eu(TTA)3·2H2O and 10 mL of isopropanol were added, and the mixture was refluxed at 80 °C for 4 hours. The solvent was distilled off to obtain the Eu complex of the target example. The yield was 87%. 31 P-NMR: -93.1 ppm (solvent: chloroform), nanoESI-MS: 1414.1064 (C 59 H 46 O9N3F9PS3Eu+Na + , theoretical value: 1414.1095)

[0077] <Synthesis of Ligand 2> Synthesis Example 2-1: Synthesis of 4-(5,5-difluoro-5H-4l4,5l4-dipyrrolo[1,2-c:2’,1’-f][1,3,2]diazaborinin-10-yl)benzyldiphenylphosphinate

Chemical formula

[0078] <Synthesis of Rare Earth Complex of Comparative Example> Comparative Synthesis Example: Synthesis of Eu(TTA)3·(TOPO)2

Chemical formula

[0079] 1 mmol of Eu(TTA)3·2H2O and 2 mmol of TOPO (trioctylphosphine oxide) were added to 10 mL of ethanol and stirred at room temperature. The solvent was distilled off to obtain the target product. Recrystallization was performed using ethanol and distilled water for purification. Thus, the Eu complex (Eu(TTA)3·(TOPO)2) of the comparative example was obtained. The yield was 78%. 31 P-NMR: -49.8 ppm (solvent: chloroform), nanoESI-MS: 1611.6082 (C 72 H 114 O8F9P2S3Eu+Na + , theoretical value: 1611.6117)

[0080] Evaluation 0.35 mmol of the Eu complex was dissolved in 10 mL of chloroform and diluted 1000-fold to obtain a measurement sample.

[0081] For the measurement of the absorption wavelength, a Jasco V-650 spectrophotometer was used to measure the absorbance. For the measurement of the excitation wavelength and the fluorescence wavelength, a Hitachi High-Tech F-7000 and a long-pass filter: LPF-39 were used to measure the photoluminescence intensity (PL Intensity). A square cell (□10 mm, made of quartz) was used for each measurement. For the measurement of the excitation wavelength, 615 nm was set as the monitor wavelength. For the measurement of the fluorescence wavelength, 350 nm was set as the excitation wavelength.

[0082] The measurement results of the absorption wavelength, excitation wavelength, and fluorescence wavelength of the Eu complex of the example (the Eu complex represented by the above formula (1-4)) are shown in FIGS. 2 to 4. The measurement results of the absorption wavelength, excitation wavelength, and fluorescence wavelength of the Eu complex of the comparative example are shown in FIGS. 5 to 7.

[0083] <Preparation and Evaluation of Colored Resin Composition> 8.0 g of chloroform was dissolved with 2.0 g of a general-purpose polystyrene resin and 0.050 g of the compound represented by the formula (1-4) to prepare a resin solution. The resin solution was applied onto a glass plate with a bar coater, and the solvent was air-dried to create a colored resin film with a film thickness of 10 μm. For this film, absorption wavelength and fluorescence wavelength measurements were performed. For the absorption wavelength measurement, a Jasco V-650 spectrophotometer was used. For the fluorescence wavelength measurement, an Otsuka Electronics MCPD9800 was used, and the excitation wavelength was set to 365 nm. The results of the absorption wavelength measurement and the fluorescence wavelength measurement are shown in FIGS. 8 to 9, respectively.

Claims

1. A compound represented by the following formula (III). 【Chemical 1】 [In the formula,[[]] X １１ and X １２ each independently represents an aromatic group, a heteroaromatic group, a C １～１２ alkyl group, a C ３～１２ alkenyl group, a C ３～１２ cycloalkyl group, a C ３～１２ cycloalkenyl group, a C ３～１２ alkynyl group, an aromatic oxy group, a heteroaromatic oxy group, a C １～１２ alkyloxy group, a C ３～１２ alkenyloxy group, a C ３～１２ cycloalkyloxy group, a C ３～１２ cycloalkenyloxy group, or a C ３～１２ alkynyloxy group, and Z １ represents a group represented by the following formula (Ib) or (IIb). 【Chemical Formula 2】 [Chemical Formula 3]

2. A metal complex comprising a metal ion and the compound according to Claim 1 coordinated to the metal ion.

3. A compound represented by the following formula (3). [Chemical Formula 4] [In formula (3),[[]] X ３１ and X ３２ each independently represents an aromatic group, a heteroaromatic group, a C １～１２ alkyl group, a C ３～１２ alkenyl group, a C ３～１２ cycloalkyl group, a C ３～１２ cycloalkenyl group, or a C ３～１２ alkynyl group, and R ３５ represents a C １－１２ alkyl group, L ４ represents an alkylene group or an arylene group.

4. R ３５ The compound according to claim 3, wherein R is a methyl group and L4 is an n-propylene group.

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