Lyleneimide compounds, luminescent materials containing them, and their applications.

Abstract

Provided are a novel releneimide compound, a luminescent material containing the same, and a luminescent ink using the same. 【Solution means】The releneimide compound is represented by the following structural formula. TIFF2026115064000033.tif3273 [X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 、 X 8 、 X 9 and X 10 are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a heteroaromatic group having 3 to 6 carbon atoms. Y 1 is an alkylene group having 1 to 6 carbon atoms in which one or more hydrogen atoms are substituted with a group selected from the group consisting of a sulfanyl group, a hydrocarbon thio group, a hydroxy group, a carboxy group, an amino group, an amide group, a guanidino group, an imidazolyl group, a phenyl group, a hydroxyphenyl group, and an indolyl group. Y 2 is an oxygen atom or a nitrogen atom.]

Description

[Technical Field]

[0001] This disclosure relates to leyleneimide compounds, luminescent materials containing the same, and applications thereof. [Background technology]

[0002] Liquid light-emitting materials that exhibit liquid-like fluidity at room temperature (hereinafter referred to as room-temperature liquid light-emitting materials) are attracting attention because they can be miscible with other solute molecules without using environmentally harmful organic solvents and can emit emission wavelengths dependent on the solute molecule, making them suitable for applications such as anti-counterfeiting inks and recording media.

[0003] Patent Document 1 and Non-Patent Document 1 disclose a room-temperature liquid material consisting of a tetracarboxylic acid diimide skeleton. This room-temperature liquid material exhibits almost no luminescence on its own, but a solution prepared using it as a solvent for dissolving a naphthalene derivative becomes a room-temperature liquid luminescent material exhibiting luminescence properties. Furthermore, depending on the type of naphthalene derivative dissolved, this room-temperature liquid luminescent material shows maximum peaks at various emission wavelengths.

[0004] Non-patent document 2 discloses a room-temperature liquid material consisting of a naphthaleneimide compound in which a bromine atom is substituted. This room-temperature liquid luminescent material exhibits phosphorescence at room temperature, but the luminescence intensity is extremely low (absolute luminescence quantum yield of 0.1%), and its luminescence properties are not sufficient for use as a luminescent material. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] Japanese Patent Publication No. 2024-109062 [Non-patent literature]

[0006] [Non-Patent Document 1] Isoda et al., Chemical Communications, 2024, 60, 9352.

Non-Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0007] The room-temperature liquid compound composed of the naphthalene imide compound substituted with a bromine atom disclosed in Non-Patent Document 2 has a significantly low luminescence intensity (absolute quantum yield is 0.1%), so it does not have sufficient properties for use as a material. Therefore, the development of a room-temperature liquid compound that exhibits luminescence with higher efficiency has been demanded.

[0008] From the above, one aspect of the present disclosure aims to provide a room-temperature liquid compound, a room-temperature liquid material, and an ink containing the same that exhibit luminescence with higher efficiency.

Means for Solving the Problems

[0009] The present inventors achieved an improvement in the absolute quantum yield of luminescence by introducing a bulky amino acid into the rylene imide compound. Furthermore, they found that it is useful as a luminescent material for dissolving various π-conjugated compounds at high concentrations, and by using the rylene imide compound, it is possible to provide luminescent materials, luminescent inks, and luminescent paints that exhibit various luminescent properties and luminescent colors, and thus completed the present invention.

[0010] The first aspect of the present invention is a rylene imide compound represented by formula (1).

Chemical Formula

[0011] A second aspect of the present invention is a luminescent material containing a leyleneimide compound represented by formula (1). [ka] [In formula (1), R 1 , X 1 ~X 10 , Y 1 , Y 2 , m, and n are synonymous with those stated above.

[0012] A third aspect of the present invention is a fluorescent paint for inkjet printing, a fluorescent ink for security, a fluorescent ink for writing instruments, a fluorescent dye for clothing, a dye for medical use, a light-emitting material for an electroluminescent element, or a wavelength conversion material, which includes a light-emitting material according to the second aspect. [Effects of the Invention]

[0013] The present invention provides a light-emitting material and a light-emitting ink that exhibit a highly efficient absolute luminescence quantum yield. [Brief explanation of the drawing]

[0014] [Figure 1] This figure shows the results of the thermogravimetric measurements for (A-1) and (A-2). [Figure 2] This figure shows the results of UV-Vis spectrophotometric measurements, spectrofluorescence measurements, and quantum yield measurements at room temperature for (A-1) and (A-2). [Modes for carrying out the invention]

[0015] Preferred embodiments of the present invention will be described in detail below.

[0016] <Lyleneimide compounds> [ka] In formula (1), X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 、 X 8 、 X9 and X 10 Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydrocarbon group with 1 to 6 carbon atoms, an aromatic hydrocarbon group with 6 to 12 carbon atoms, or a heteroaromatic group with 3 to 6 carbon atoms. 1 ~X 3 , X 9 and X 10 and X 4 ~X 6 , X 7 and X 8 These elements may be joined together to form a ring. n is an integer between 0 and 2. It is preferable that n be between 0 and 1 because the raw materials are readily available, and it is more preferable that n be 0 because the synthesis is easy. In terms of exhibiting phosphorescence, X 1 ~X 10 At least one of them is preferably a halogen atom, and more preferably a bromine atom or an iodine atom. Also, X 3 or X 4 It is especially preferable that one of them is a bromine atom. X 1 ~X 10 The hydrocarbon group having 1 to 6 carbon atoms represented by can be linear, branched, or cyclic, and examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-methylpropyl group, 2-methylcyclopropyl group, 3-methylpropyl group, pentyl group, 2-methylbutyl group, 3-methylbutyl group, 4-methylbutyl group, hexyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,3-dimethylbutyl group, 3-ethylpentyl group, etc. X 1 ~X 10 The aromatic hydrocarbon group having 6 to 12 carbon atoms represented by is preferably 6 to 10 carbon atoms. The aromatic hydrocarbon group may be a monocyclic aromatic hydrocarbon group, an aromatic hydrocarbon group in which two or more aromatic rings are linked, or a fused aromatic hydrocarbon group. Examples of such aromatic hydrocarbon groups include phenyl group, biphenylyl group, naphthyl group, etc. X 1 ~X 10The heteroaromatic group having 3 to 6 carbon atoms represented by may be a monocyclic heteroaromatic group, a heteroaromatic group in which two or more aromatic rings are linked, or a fused heteroaromatic group. If the heteroaromatic group has multiple aromatic rings, it is sufficient that at least one of the aromatic rings contains a heteroatom (e.g., an oxygen atom, a nitrogen atom, a sulfur atom, etc.). Examples of such heteroaromatic groups include pyrrolyl group, thienyl group, furyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, pyridyl group, pyrimidyl group, pyrazyl group, 1,3,5-triazinyl group, etc. Adjacent X 1 ~X 3 , X 9 and X 10 and X 4 ~X 6 , X 7 and X 8 These groups may bond to each other to form a ring, and examples of rings formed by the bonding of these groups include aromatic rings with 4 to 30 nuclear atoms. The aromatic ring may be an aromatic hydrocarbon ring, a heteroaromatic ring, an annulene aromatic ring, or a troponoid aromatic ring, with aromatic hydrocarbon rings or heteroaromatic rings being preferred due to their ease of synthesis. Examples of aromatic hydrocarbon rings include benzene rings, naphthalene rings, anthracene rings, tetracene rings, pyrene rings, triphenylene rings, phenanthrene rings, perylene rings, coronene rings, and the like. Examples of the heteroaromatic rings include pyrazole rings, imidazole rings, thiophene rings, furan rings, pyrrole rings, benzofuran rings, benzothiophene rings, dibenzofuran rings, dibenzothiophene rings, pyrimidine rings, pyrazine rings, pyridine rings, quinoline rings, isoquinoline rings, phthalazine rings, naphthyridine rings, quinoxaline rings, quinazoline rings, acridine rings, phenanthroline rings, and the like.

[0017] Y 1Each of these independently represents an alkylene group having 1 to 6 carbon atoms, which may be substituted with one or more hydrogen atoms by a group selected from the group consisting of a sulfanyl group, a hydrocarbon thio group, a hydroxyl group, a carboxyl group, an amino group, an amide group, a guanidino group, an imidazolyl group, a phenyl group, a hydroxyphenyl group, and an indolyl group. 1 In terms of ease of synthesis, the group represented by any of the following formulas (a-1) to (a-18) is preferred, the group represented by formulas (a-1), (a-2), (a-3), (a-4), (a-5), or (a-16) is more preferred, and the group represented by formulas (a-1), (a-2), (a-3), (a-4), or (a-5) is particularly preferred. [ka] Note that the divalent linking group represented by formula (an) (where n is an integer from 2 to 18) encompasses both of the two optical isomers. That is, since the divalent methine carbons in formulas (a-2) to (a-18), excluding formula (a-1), are chiral carbons, two optical isomers may exist: the D-form represented by formulas (a-2D) to (a-18D) and the L-form represented by formulas (a-2L) to (a-18L). The divalent methine carbon is assumed to be directly bonded to the nitrogen atom of the imide on the left side and to the carbon atom on the right side. For convenience, this specification uses the notation (an), which encompasses the above-mentioned D and L optical isomers. [ka] [ka]

[0018] Y 2 Y represents an oxygen atom or a nitrogen atom. 2 If it is an oxygen atom, then m is 1, and R 1This represents a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or a linear hydrocarbon group having 8 to 18 carbon atoms in which one or more -CH2- are replaced by -O-, -S-, or -(SiMe2)-, and there are no consecutive -O- or -S- groups. Y 2 If is a nitrogen atom, then m is 1 or 2, and R 1 This represents a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or a linear hydrocarbon group having 8 to 18 carbon atoms, where one or more -CH2- may be replaced by -O-, -S-, or -(SiMe2)-, but there are no consecutive -O- or -S- groups. In terms of lowering the glass transition temperature, Y 2 It is preferable that it is an oxygen atom. R 1 However, when it is a linear hydrocarbon group having 8 to 24 carbon atoms, examples include octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group, eicosyl group, eicosyl group, docosyl group, tricosyl group, tetracosyl group, etc. R 1 Examples of branched hydrocarbon groups having 8 to 24 carbon atoms include 2-octyl group, 2-ethylhexyl group, 5-methylheptyl group, 2-ethyloctyl group, 3,7-dimethyloctyl group, 2-ethyldecyl group, 2-butyldodecyl group, 2-(hexa-2-yl)-5-methyloctyl group, 3,7,11-trimethyldodecyl group, 2-hexyldodecyl group, 2-hexyltetradecyl group, 2-octyldodecyl group, 2-octyltetradecyl group, 2-octylhexyldecyl group, and 2-decyltetradecyl group. In terms of ease of synthesis, R 1 The group is preferably a branched hydrocarbon group having 12 to 22 carbon atoms, more preferably a group represented by any of the following formulas (b-1) to (b-8), and particularly preferably formulas (b-1), (b-2), (b-3), (b-4), or (b-5). [ka]

[0019] R 1 In a linear hydrocarbon group having 8 to 18 carbon atoms represented by , one or more -CH2- may be replaced with -O-, -S-, or -(SiMe2)-, but there will not be two or more consecutive -O- or three or more consecutive -S-. Such a linear hydrocarbon group is not particularly limited, but examples include groups represented by any of the following formulas (C-1) to (C-48). [ka] TIFF2026115064000009.tif106110

[0020] R 1The fluorohydrocarbon group having 8 to 16 carbon atoms represented by can be linear, branched, or cyclic, and is not particularly limited, but may include perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, perfluorododecyl, perfluorotridecyl, perfluorotetradecyl, perfluoropentadecyl, perfluorohexadecyl, 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl, 5,5,6,6,7,7,8,8,8-nonafluorooctyl, 6,6,7,7,8,8,8-heptafluorooctyl group, 7,7,8,8,8-pentafluorooctyl group, 8,8,8-trifluorooctyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-pentadecafluorononyl group, 5,5,6,6,7,7,8,8,9,9,9-undecafluorononyl group, 7,7,8,8,9,9,9-heptafluorononyl group, 8,8,9,9,9-pentafluorononyl group, 9,9,9-trifluorononyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10- Heptadecafluorodecyl group, 5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodecyl group, 7,7,8,8,9,9,10,10,10-nonafluorodecyl group, 8,8,9,9,10,10,10-heptafluorodecyl group, 9,9,10,10,10-pentafluorodecyl group, 10,10,10-trifluorodecyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-nonafluoroundecyl group, 5,5,6,6,7,7,8,8,9,9,10,10,11,1 1,11-pentadecafluoroundecyl group, 7,7,8,8,9,9,10,10,11,11,11-undecafluoroundecyl group, 9,9,10,10,11,11,11-heptafluoroundecyl group, 10,10,11,11,11-pentafluoroundecyl group, 11,11,11-trifluoroundecyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-henicosafluorododecyl group, 5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,12-Heptadecafluorododecyl group, 8,8,9,9,10,10,11,11,12,12,12-Undecafluorododecyl group, 9,9,10,10,11,11,12,12,12-Nonafluorododecyl group, 10,10,11,11,12,12,12-Heptafluorododecyl group, 11,11,12,12,12-Pentafluorododecyl group, 12,12,12-Trifluorododecyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Tricosafluorotridecyl group ,9,10,10,11,11,12,12,13,13,13-undecafluorotridecyl group, 11,11,12,12,13,13,13-heptafluorotridecyl group, 12,12,13,13,13-pentafluorotridecyl group, 13,13,13-trifluorotridecyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,14-pentacosafluorotetradecyl group, 10,10,11,11,12,12,13,13,14,14,14-undecafluoro Orotetradecyl group, 12,12,13,13,14,14,14-heptafluorotetradecyl group, 13,13,14,14,14-pentafluorotetradecyl group, 14,14,14-trifluorotetradecyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,15-heptacosafluoropentadecyl group, 11,11,12,12,13,13,14,14,15,15,15-undecafluoropentadecyl group, 13,13,14,14,15,15, 15-Heptafluoropentadecyl group, 14,14,15,15,15-Pentafluoropentadecyl group, 15,15,15-Trifluoropentadecyl group, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,14,14,15,15,16,16,16-Nonacosafluorohexadecyl group, 12,12,13,13,14,14,15,15,16,16,16-Undecafluorohexadecyl group, 14,14,15,15,16,16,16-Heptafluorohexadecyl group, 15,15,Examples include the 16,16,16-pentafluorohexadecyl group and the 16,16,16-trifluorohexadecyl group.

[0021] The leyleneimide compound represented by formula (1) in this embodiment (hereinafter sometimes referred to as "leyleneimide compound (1)") is not particularly limited, but examples include compounds represented by any of the following formulas (A-1) to (A-50) and (B-1) to (B-40). Compounds represented by any of the following formulas (A-1) to (A-12) are preferred because they are easy to synthesize, and compounds represented by any of the following formulas (A-1) to (A-6) are particularly preferred. [ka] TIFF2026115064000011.tif137101TIFF2026115064000012.tif138101TIFF2026115064000013.tif147101TIFF2026115064000014.tif148101 TIFF2026115064000015.tif117101TIFF2026115064000016.tif124101TIFF2026115064000017.tif129119TIFF2026115064000018.tif132118

[0022] In this specification, "hydrogen atom" refers collectively to light hydrogen atoms and deuterium atoms, and deuterium atom means deuterium (D) or tritium (T).

[0023] In this specification, "room temperature" refers to a temperature range of 5°C to 40°C, and "liquid" refers to all substances that are in a liquid state, regardless of their viscosity. It may also include supercooled liquids that remain liquid even after being heated and then cooled below their melting point.

[0024] The ryleneimide compound (1) of this embodiment is preferably liquid at room temperature in order to have excellent coatability as a light-emitting material. More specifically, in order to maintain a stable liquid state, the melting point or glass transition temperature of the ryleneimide compound (1) of the present invention is preferably 30°C or lower, and more preferably 5°C or lower. Furthermore, since the decomposition temperature of the ryleneimide compound (1) of the present invention is 300°C or higher, it is possible to maintain a liquid state over a wide temperature range from room temperature to the decomposition temperature.

[0025] The yleneimide compound (1) according to this embodiment can maintain its liquid state over the processing temperature range for use as an ink, so there is no change in its properties during processing. Furthermore, since the yleneimide compound (1) according to the present invention can maintain its liquid state over the temperature range in which ordinary inks are used, high reliability can be ensured. Moreover, since the yleneimide compound (1) according to the present invention can maintain its liquid state at room temperature, it can exhibit high solubility in various solvents.

[0026] <Method for producing liyleneimide compounds> The ryleneimide compound (1) of this embodiment can be produced by reacting the compound represented by formula (2) and the compound represented by formula (3) in the presence of additive (4), as shown in step 1 below. [ka] In equation (1), in equation (2), and in equation (3), R 1 , X 1 ~X 10 , Y 1 , Y 2 m and n are equivalent to those stated above. By applying the reaction conditions disclosed in Examples 1 to 6, or general esterification or amidation reaction conditions, the ryleneimide compound (1) of this embodiment can be obtained in good yield.

[0027] The compound represented by formula (2) can be synthesized, for example, based on the methods disclosed in the literature (ACS Catalys, 2012, 2, 122; Chemical Communications, 2024, 60, 1770; Organic Letters, 2008, 10, 5473; Synthesis, 2013, 45, 2079; Angewandte Chemie, International Edition, 2015, 54, 2729), or commercially available products may be used.

[0028] The compound represented by formula (3) is, for example, described in the literature (JP 2008-31149; Macromolecules, 2015, 48, 520; Journal of Organic Chemistry, 1962, 27, 2821; Angewandte Chemie, International Edition, 2018, 57, 8493; Journal of the American Chemical Society, 2016, 138, 4210; JP FR1573705; International Publication No. 2010 / 126030; ACS Omega, 2017, 2, 2483; Journal of the American Chemical Society, 2018, 140, 515; ACS Macro Letters, 2012, 1, 136; Journal of Materials Chemistry C:2015, 31, 33; ACS Applied Materials & It can be synthesized based on the method disclosed in Interfaces, 2017, 9, 16967), or a commercially available product may be used. The equivalent amount of formula (3) used in step 1 is preferably in the range of 0.5 to 2.0 equivalents relative to formula (2) in terms of good reaction yield of the ryleneimide compound (1) in this embodiment, and more preferably in the range of 0.7 to 1.2 equivalents in terms of ease of purification.

[0029] Step 1 can be carried out in a solvent. Various solvents can be selected considering the solubility of the substrate, such as a carboxylic acid or alcohol. For example, ethers such as diethyl ether, diisopropyl ether, methyl-tert-butyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, tetrahydrofuran, and 1,4-dioxane; halogenated hydrocarbons such as dichloromethane, dichloroethane, chloroform, and chlorobenzene; amides such as dimethylformamide, dimethyl sulfoxide, and hexamethyl phosphate triamide; and imidazoles such as imidazole, methylimidazole, and dimethylimidazolidinone can be used. These may be used individually or mixed in any ratio. There are no particular restrictions on the amount of solvent used. Of these, dichloromethane and chloroform are preferred in terms of high reaction yield, and dichloromethane is more preferred in terms of economy and ease of post-treatment.

[0030] Step 1 can be carried out in the presence of an acid. Examples of the acid include inorganic acid solvents such as hydrochloric acid, nitric acid, sulfuric acid, and phosphoric acid; and organic acids such as formic acid, acetic acid, trifluoroacetic acid, propionic acid, butyric acid, valeric acid, hexanoic acid, oxalic acid, methanesulfonic acid, and trifluoromethanesulfonic acid. Acetic acid or propionic acid is preferred because it has a high reaction yield. Step 1 can be carried out in the presence of a base. Examples of such bases include organic bases such as triethylamine, pyridine, 4-dimethylaminopyridine, 1,8-diazabicyclo[5.4.0]undeca-7-ene, tetramethylethylenediamine, and 1,4-diazabicyclo[2.2.2]octane; metal hydroxides such as sodium hydroxide, potassium hydroxide, cesium hydroxide, magnesium hydroxide, calcium hydroxide, and barium hydroxide; metal carbonates such as sodium carbonate, potassium carbonate, lithium carbonate, and cesium carbonate; metal acetates such as potassium acetate and sodium acetate; metal phosphates such as potassium phosphate and sodium phosphate; metal fluoride salts such as sodium fluoride, potassium fluoride, and cesium fluoride; and metal alkoxides such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium isopropyl oxide, potassium tert-butoxide, and sodium tert-butoxide. Triethylamine, pyridine, or 4-(dimethylamino)pyridine are preferred due to the readily available raw materials, and triethylamine is more preferred due to its high reaction yield.

[0031] Step 1 can be carried out in the presence of a condensing agent. The condensing agent may be 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, N,N'-diisopropylcarbodiimide, N,N'-carbonyldiimidazole, 1,1'-carbonyldi(1,2,4-triazole), 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride n hydrate, or 1H-benzotriazole-1-yl Bromotris(dimethylamino)phosphonium hexafluorophosphate, 1H-benzotriazole-1-yloxytripyrrolidinophosphonium hexafluorophosphate, (7-azabenzotriazole-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, chlorotripyrrolidinophosphonium hexafluorophosphate, bromotris(dimethylamino)phosphonium hexafluorophosphate, 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazine-4(3H)-one, O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, O-(3,4-dihydro-4-oxo-1,2,3-ben Zotriazin-3-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, S-(1-oxide-2-pyridyl)-N,N,N',N'-tetramethylthiuronium tetrafluoroborate, O-[2-oxo-1(2H)-pyridyl]-N,N,N',N'-tetramethyluronium tetrafluoroborate, {{[(1-cyano-2-ethoxy-2-oxoethylidene)amino]oxy}-4-morpholinomethylene}dimethylammonium hexafluorophosphate, 2-chloro-1,Examples of condensing agents include 3-dimethylimidazolinium hexafluorophosphate, 1-(chloro-1-pyrrolidinylmethylene)pyrrolidinium hexafluorophosphate, 2-fluoro-1,3-dimethylimidazolinium hexafluorophosphate, fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate, 1-hydroxybenzotriazole, 1-hydroxy-7-azabenzotriazole, N-hydroxysuccinimide, and N,N'-disuccinimidyl carbonate; however, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and N,N'-dicyclohexylcarbodiimide are preferred due to their high reaction yield.

[0032] The acid, base, and coupling agent may each be used individually or mixed in any ratio. For high reaction yield, it is preferable to use 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, N,N'-dicyclohexylcarbodiimide, or N,N'-diisopropylcarbodiimide as the coupling agent and triethylamine, pyridine, or 4-dimethylaminopyridine as the base. For high product purity, it is more preferable to use 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride as the coupling agent and 4-dimethylaminopyridine as the organic base. Furthermore, the equivalent amounts of these additives are preferably in the range of 1.0 to 2.4 equivalents, and more preferably in the range of 1.5 to 2.0 equivalents, relative to formula (2), for good reaction yield of the ryleneimide compound (1) in this embodiment.

[0033] Step 1 can be carried out at a temperature appropriately selected from -80°C to 100°C, but it is preferable to carry it out at a temperature appropriately selected from -20°C to 60°C in order to obtain a high reaction yield of the ryleneimide compound (1).

[0034] <Liquid light-emitting material and method for manufacturing liquid light-emitting material> The room-temperature liquid luminescent material of this embodiment preferably contains a leyleneimide compound represented by formula (1) above, and further preferably contains a π-conjugated compound. The π-conjugated compound contained in the room-temperature liquid luminescent material of this embodiment is an aromatic compound having 6 to 20 carbon atoms or a heteroaromatic compound having 3 to 14 carbon atoms. There are no particular limitations, but examples of substituted compounds include naphthalene, anthracene, tetracene, pyrene, triphenylene, phenanthrene, perylene, coronene, stilbene, phenylenevinylene, phenyleneethynylene, phenanthrene, fluorene, tetraphenylethene, thiophene, 2,2'-bithiophene, 2,2':5',2''-terthiophene, pyrrole, furan, silole, thiazole, thiadiazole, pyridine, pyrazine, triazine, quinoxaline, phenazine, triphenylamine, etc. These may be used individually or in combination in any ratio. Aromatic compounds having 6 to 16 carbon atoms or heteroaromatic compounds having 3 to 10 carbon atoms are preferred due to their high solubility in lylenimide compound (1), and naphthalene, anthracene, and pyrene are more preferred.

[0035] The room-temperature liquid light-emitting material of this embodiment can be produced, for example, by kneading the ryleneimide compound (1) of the present invention with a π-conjugated compound (hereinafter referred to as step 2). The kneading method can be a general method such as stirring, shaking, or a ball mill.

[0036] The mixing conditions in step 2 are not particularly limited. For example, by applying the conditions disclosed in Example ##, the room-temperature liquid light-emitting materials (A-3-a), (A-3-b), (A-3-c), (A-3-d), and (A-3-e) of this embodiment can be efficiently obtained.

[0037] Step 2 can be carried out by heating at a temperature appropriately selected from 20 to 150°C for 5 minutes or more, and it is preferable to carry it out by heating at a temperature appropriately selected from 20 to 60°C for 5 minutes or more, as this makes preparation easier.

[0038] The amount of yleneimide compound (1) contained in the room-temperature liquid light-emitting material of this embodiment is preferably in the range of 50 to 99.9% by weight, and more preferably in the range of 70 to 99.6% by weight, based on the total amount of the liquid light-emitting material, in order to obtain good light-emitting properties.

[0039] <Method for manufacturing luminescent ink and luminescent ink> The luminescent ink of this embodiment comprises the room-temperature liquid luminescent material and solvent of the present invention.

[0040] The content of the leyleneimide compound (1) in the luminescent ink of this embodiment is preferably in the range of 30 to 70% by weight, based on the total amount of the luminescent ink, in order to obtain good luminescence characteristics.

[0041] The solvent contained in the luminescent ink of this embodiment can be an alcohol, acetone, hexane, dichloromethane, chloroform, ethyl acetate, toluene, acetonitrile, etc., and in terms of safety, it is preferable that it be at least one organic solvent selected from the group consisting of C2-C6 alcohols, C6-C10 isoparaffinic hydrocarbons, and C6-C14 alicyclic hydrocarbons.

[0042] The C2-C6 alcohols may be used individually or in combination of two or more. The C2-C6 alcohols may include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, tert-butyl alcohol, isobutyl alcohol, n-pentanol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-1-propanol, 1-methoxy-2-propanol, 3-methoxy-n-butanol, etc.

[0043] The isoparaffinic hydrocarbons may be used as the main component of the solvent, either individually or in combination of two or more. Isoparaffinic hydrocarbons having 6 to 10 carbon atoms are obtained by refining and / or synthesizing petroleum raw materials. From the viewpoint of obtaining excellent low odor properties, saturated isoparaffinic hydrocarbons are preferred. Examples of commercially available isoparaffinic hydrocarbons include IP Solvent 1016, IP Solvent 1620, IP Solvent 2028 and IP Solvent 2835 (all manufactured by Idemitsu Kosan Co., Ltd., trade names), the Isosol series (manufactured by Nippon Oil Corporation, trade name), Shellsol TG, Shellsol TK and Shellsol TM (all manufactured by Showa Shell Sekiyu Co., Ltd., trade names), Isopar E and Isopar G (manufactured by ExxonMobil Corporation, trade names), and so on.

[0044] The alicyclic hydrocarbons having 6 to 14 carbon atoms may be used as the main component of the solvent, either individually or in combination of two or more. Examples of alicyclic hydrocarbons having 6 to 14 carbon atoms include methylcyclohexane and ethylcyclohexane.

[0045] The luminescent ink of this embodiment can be manufactured, for example, by dissolving and dispersing the room-temperature liquid luminescent material of the present invention in a solvent (hereinafter referred to as step 3). General methods such as stirring, shaking, and ball milling can be used for dissolving and dispersing.

[0046] <Applications of room-temperature liquid light-emitting materials and light-emitting inks> The room-temperature liquid light-emitting material and light-emitting ink of this embodiment can be used, for example, in fluorescent paints for inkjet printing, fluorescent inks for security, fluorescent inks for writing instruments, fluorescent dyes for clothing, medical dyes, light-emitting materials for electroluminescent devices, wavelength conversion materials, and the like.

[0047] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In addition, 1For the measurement of 1H-NMR, Bruker ASCEND HD (400 MHz; manufactured by Bruker) was used. 1 1H-NMR was measured using deuterated chloroform (CDCl3) as the measurement solvent and tetramethylsilane (TMS) as the internal standard substance.

[0048] Synthesis Example 1: Rilenimide Compound (A-1)

Chemical Structure

[0049] Synthesis Example 2: Lyleneimide Compound (A-2) [ka] Under an argon atmosphere, 2-(1,3-dioxo-1H-benzo[de]isoquinoline-2(3H)-yl)-4-methylvaleric acid (6.0 g, 20.2 mmol), 2-hexyl-decanol (5.33 g, 22.2 mmol), EDC (7.71 g, 40.3 mmol), and DMAP (4.95 g, 40.3 mmol) were suspended in CH2Cl2 (100 ml) and stirred overnight at room temperature. Distilled water and 1 M HCl were then added, and the organic layer was separated. The organic layer was then dehydrated with magnesium sulfate. After solvent removal, the target compound (A-2) was obtained as a colorless liquid (3.40 g, 32%) by silica gel column chromatography (CHCl3:hexane = 9:1). 1 HNMR(400MHz,CDCl3):δ8.61(dd,J=7.3,1.0Hz,2H),8.24(dd,J=8.2,1.0Hz,2H),7.77(dd,J=8.2, 7.3Hz,2H),5.78(dd,J=9.0,5.0Hz,1H),4.05(dd,J=10.8,6.0Hz,1H),3.97(dd,J=10.8,6.0Hz,1H) ,2.25(ddd,J=14.4,9.0,5.0Hz,1H),2.10(ddd,J=14.4,9.0,5.0Hz,1H),1.46-1.67(m,2H),0.95-1 .33(m,24H),1.01(d,J=6.5Hz,3H),0.93(d,J=6.5Hz,3H),0.87(t,J=7.2Hz,3H),0.78-0.84(m,3H)

[0050] Synthesis Example 3: Lyleneimide (A-3) [ka] Under an argon atmosphere, 2-(6-bromo-1,3-dioxo-1H-benzo[de]isoquinoline-2(3H)-yl)-4-methylvaleric acid (0.976 g, 2.50 mmol), 1-decanol (0.450 g, 2.75 mmol), EDC (0.960 g, 5.00 mmol), and DMAP (1.28 g, 10.0 mmol) were suspended in CH2Cl2 (35.0 mL) and stirred overnight at room temperature. Distilled water and 1 M HCl were then added, and the organic layer was separated. The organic layer was then dehydrated with magnesium sulfate. After solvent removal, the target compound (A-3) was obtained as a yellow powder (0.410 g, 31%) by recrystallization (CHCl3 / CH3OH). 1 HNMR(400MHz,CDCl3):δ8.67(dd,J=7.3,1.1Hz,1H),8.61(dd,J=8.5,1.1Hz,1H),8.42(d,J=7.9Hz,1H),8 .06(d,J=7.9Hz,1H),7.87(dd,J=8.5,7.3Hz,1H),5.74(dd,J=9.2,5.0Hz,1H),4.16(dt,J=10.7,6.7Hz,1 H),4.07(dt,J=10.7,6.7Hz,1H),2.23(ddd,J=14.4,9.2,5.0Hz,1H),2.09(ddd,J=14.4,9.2,5.0Hz,1H), 1.48-1.63(m,3H),1.03-1.32(m,14H),1.01(d,J=6.7Hz,3H),0.92(d,J=6.7Hz,3H),0.87(t,J=7.1Hz,3H)

[0051] Synthesis Example 4: Lyleneimide (A-4) [ka] Under an argon atmosphere, 2-(1,3-dioxo-1H-benzo[de]isoquinoline-2(3H)-yl)-4-methylvaleric acid (1.00 g, 2.56 mmol), 1-decanol (0.322 g, 2.05 mmol), EDC (0.988 g, 5.13 mmol), and DMAP (0.614 g, 5.13 mmol) were suspended in CH2Cl2 (30.0 mL) and stirred overnight at room temperature. Distilled water and 1 M HCl were then added, and the organic layer was separated. The organic layer was then dehydrated with magnesium sulfate. After solvent removal, the target compound (A-4) was obtained as a pale yellow liquid (0.26 g, 22%) by silica gel column chromatography (Â:hexane = 2:1). 1 HNMR(400MHz,CDCl3):δ8.61(dd,J=7.3,1.0Hz,2H),8.24(dd,J=8.2,1.0Hz,2H),7.77(dd,J=8.2, 7.3Hz,2H),5.78(dd,J=9.0,5.0Hz,1H),4.05(dd,J=10.8,6.0Hz,1H),3.97(dd,J=10.8,6.0Hz,1H) ,2.25(ddd,J14.4,9.0,5.0Hz,1H),2.10(ddd,J=14.4,9.0,5.0Hz,1H),1.46-1.67(m,2H),0.95-1 .33(m,24H),1.01(d,J=6.5Hz,3H),0.93(d,J=6.5Hz,3H),0.87(t,J=7.2Hz,3H),0.78-0.84(m,3H)

[0052] Synthesis Example 5: Lyleneimide (A-5) [ka] Under an argon atmosphere, 2-(6-bromo-1,3-dioxo-1H-benzo[de]isoquinoline-2(3H)-yl)-4-methylvaleric acid (1.00 g, 2.57 mmol), triethylene glycol monomethyl ether (0.328 g, 2.06 mmol), EDC (0.985 g, 5.14 mmol), and DMAP (0.626 g, 5.14 mmol) were suspended in CH2Cl2 (16.0 mL) and stirred overnight at room temperature. Distilled water and 1 M HCl were then added to separate the organic layer. The organic layer was then washed with saturated brine and dehydrated with magnesium sulfate. After solvent removal, the target compound (A-5) was obtained as a yellow solid (0.240 g, 17%) by recrystallization (Â / hexane) and silica gel column chromatography (Â:hexane = 2:1). 1 HNMR (400MHz, CDCl3): δ8.66(dd,J=7.3,1.1Hz,1H),8.61(dd,J=8.5,1.1Hz,1H),8.42(d,J=7.9Hz,1H),8.07( d,J=7.9Hz,1H),7.87(dd,J=8.5,7.3Hz,1H),5.77(dd,J=9.2,5.0Hz,1H),4.33(ddd,J=11.9,6.0,4.1Hz,1H),4 .24(ddd,J=11.9,6.0,4.1Hz,1H),3.57-3.68(m,2H),3.37-3.53(m,8H),3.35(s,3H),2.23(ddd,J=14.3,9.2, 5.0Hz,1H),2.08(ddd,J=14.3,9.2,5.0Hz,1H),1.54-1.61(m,1H),1.01(d,J=6.7Hz,3H),0.92(d,J=6.7Hz,3H)

[0053] Synthesis Example 6: Lyleneimide (A-6) [ka] Under an argon atmosphere, 2-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)-4-methylvaleric acid (1.01 g, 3.21 mmol), triethylene glycol monomethyl ether (0.425 g, 2.57 mmol), EDC (1.23 g, 6.42 mmol) and DMAP (0.776 g, 6.42 mmol) were suspended in CH2Cl2 (16.0 mL) and stirred at room temperature overnight. Next, distilled water and 1 M HCl were added, and the organic layer was separated. Then, the organic layer was washed with saturated brine and dehydrated with magnesium sulfate. After evaporation of the solvent, silica gel column chromatography (EtOAc:hexane = 1:2) was performed to obtain the target compound (A-6) as a yellow solid (0.460 g, 31%). 1 HNMR(400MHz,CDCl3):δ8.60(dd,J=7.3,0.9Hz,2H),8.24(d,J=8.2,0.9Hz,2H),7.77(t,J=8.2,7.3Hz,2H),5.79(dd,J=9.1,5.0Hz,1H),4.34(ddd,J=11.8,5.7,4.1Hz,1H),4.24(ddd,J=11.8,5.7,4.1Hz,1H),3.57 - 3.68(m,2H),3.34 - 3.53(m,8H),3.34(s,3H),2.24(ddd,J=14.4,9.2,5.0Hz,1H),2.09(ddd,J=14.4,9.2,5.0Hz,1H),1.52 - 1.65(m,1H),1.01(d,J=6.6Hz,3H),0.92(d,J=6.6Hz,3H)

[0054] Using a thermogravimetric analyzer (TG / DTA6200, manufactured by Hitachi High-Technologies Corporation), the decomposition temperatures of the relenimide compounds (A-1) and (A-2) were measured. The measurement conditions were as follows: under an argon atmosphere, heating rate of 10 o °C / min from 20 o °C to 1000 o °C, and the weight changes of (A-1) and (A-2) were measured. The results are shown in Figure 1, which will be described later.

[0055] The absorption spectra of (A-1) and (A-2) were measured using a UV-Vis spectrophotometer (JASCOV-770, manufactured by JASCO Corporation, UV / vis bandwidth: 2.0 nm, UV / vis response: 0.24 sec, scanning mode: continuous scan, scanning speed: 1000 nm / min). The measurements were performed by transmission using a film in which the sample was coated on a quartz substrate. The results are shown in Figure 2.

[0056] The emission spectra and absolute quantum yields of (A-1) and (A-2) were measured using a spectrofluorometer (JASCOFP-8500, manufactured by JASCO Corporation; excitation bandwidth: 5 nm, fluorescence bandwidth: 5 nm, response: 10 msec, sensitivity: Manual, scanning mode: continuous scan, scanning speed: 100 nm / min). The samples used for measurement were films coated on a quartz substrate. The emission spectra when excited at the excitation wavelength (shown in Figure 2) are shown in Figure 2 and will be described later.

[0057] From the thermogravimetric results in Figure 1, the temperature at which (A-1) loses 5% of its weight is 243°C. o The temperature at which C, (A-2) loses 5% of its weight is 289°C. o It has been confirmed that C is thermally stable even in high-temperature environments.

[0058] As shown in Figure 2, (A-1) exhibits yellow emission with an emission maximum peak at 536 nm (absolute quantum yield Φ = 9.7%), and (A-2) exhibits cyan emission with an emission maximum peak at 451 nm (absolute quantum yield Φ = 0.9%). In other words, it was confirmed that (A-1) and (A-2) of the present invention can achieve the expression of various emission colors and high absolute quantum yield.

Claims

1. A leyleneimide compound represented by formula (1). 【Chemistry 1】 [In formula (1), X １ 、 X ２ 、 X ３ 、 X ４ 、 X ５ 、 X ６ 、 X ７ 、 X ８ 、 X ９ and X １０ each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a heteroaromatic group having 3 to 6 carbon atoms. Adjacent X １ ~X ３ , X ９ and X １０ and X ４ ~X ６ , X ７ and X ８ These elements may be joined together to form a ring. Y １ Each of these independently represents an alkylene group having 1 to 6 carbon atoms, which may be substituted with one or more hydrogen atoms by a group selected from the group consisting of a sulfanyl group, an alkylthio group, a hydroxyl group, a carboxyl group, an amino group, an amide group, a guanidino group, an imidazolyl group, a phenyl group, a hydroxyphenyl group, and an indolyl group. Y ２ This represents an oxygen atom or a nitrogen atom. Y ２ If it is an oxygen atom, then m is 1, and R １ This is a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or one or more -CH groups. ２ - is -O-, -S- or -(SiMe ２ ) - may be substituted, but it represents a linear hydrocarbon group having 8 to 18 carbon atoms where there are no consecutive -O- or -S- groups. Y ２ If it is a nitrogen atom, then m is 1 or 2, and R １ This is a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or one or more -CH groups. ２ - is -O-, -S- or -(SiMe ２ ) - may be substituted, but it represents a linear hydrocarbon group having 8 to 18 carbon atoms where there are no consecutive -O- or -S- groups. n represents an integer between 0 and 2.

2. The yleneimide compound according to claim 1, wherein the melting point, freezing point, or glass transition temperature is 30°C or lower.

3. In equation (1), X １ ~X １０ The yleneimide compound according to claim 1 or 2, wherein at least one of the atoms is a halogen atom.

4. In equation (1), X １ ~X １０ The yleneimide compound according to claim 1 or 2, wherein the halogen atom is a bromine atom or an iodine atom.

5. In equation (1), X ３ or X ４ The yleneimide compound according to claim 1 or 2, wherein one of the atoms is a bromine atom or an iodine atom.

6. In equation (1), R １ The yleneimide compound according to claim 1 or 2, wherein is a branched hydrocarbon group having 8 to 24 carbon atoms.

7. In equation (1), Y １ The yleneimide compound according to claim 1 or 2, wherein is an optionally substituted alkylene group represented by any of the following formulas (a-1) to (a-18). 【Chemistry 2】

8. The yleneimide compound according to claim 1 or 2, wherein the yleneimide compound represented by formula (1) is a compound represented by any of formulas (A-1) to (A-6). 【Transformation 3】

9. Compound represented by formula (2) 【Chemistry 4】 (In formula (2), X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ 、 X ８ 、 X ９ and X １０ Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a heteroaromatic group having 3 to 6 carbon atoms. Adjacent X １ ~X ３ , X ９ and X １０ and X ４ ~X ６ , X ７ and X ８ These elements may be joined together to form a ring. Y １ Each of these independently represents an alkylene group having 1 to 6 carbon atoms, which may be substituted with one or more groups selected from the group consisting of a sulfanyl group, an alkylthio group, a hydroxyl group, a carboxyl group, an amino group, an amide group, a guanidino group, an imidazolyl group, a phenyl group, a hydroxyphenyl group, and an indolyl group. n represents an integer between 0 and 2.) and the compound shown in formula (3). 【Transformation 5】 (In formula (3), Y ２ This represents an oxygen atom or a nitrogen atom. Y ２ If it is an oxygen atom, then m is 1, and R １ This is a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or one or more -CH groups. ２ - is -O-, -S- or -(SiMe ２ ) - may be substituted, but it represents a linear hydrocarbon group having 8 to 18 carbon atoms where there are no consecutive -O- or -S- groups. Y ２ If it is a nitrogen atom, then m is 1 or 2, and R １ This is a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or one or more -CH groups. ２ - is -O-, -S- or -(SiMe ２ ) which may be replaced with -, but represents a linear hydrocarbon group having 8 to 18 carbon atoms in which there are no consecutive -O- or -S- groups.) is reacted with at least one additive selected from the group consisting of acids, bases, and condensing agents, formula (1) 【Transformation 6】 (In formula (1), R １ , X １ ~X １０ , Y １ , Y ２ A method for producing a leyleneimide compound represented by ). , m, and n are as defined above.

10. The manufacturing method according to claim 9, wherein the additive is an acid, a base, or a carbodiimide compound.

11. A luminescent material containing a leyleneimide compound represented by formula (1). 【Transformation 7】 [In formula (1), X １ , X ２ , X ３ , X ４ , X ５ , X ６ , X ７ 、 X ８ 、 X ９ and X １０ Each of these independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 carbon atoms, or a heteroaromatic group having 3 to 6 carbon atoms. Adjacent X １ ~X ３ 、X ９ and X １０ as well as X ４ ~X ６ 、X ７ and X ８ may be combined with each other to form a ring. Y １ Each of these independently represents an alkylene group having 1 to 6 carbon atoms, which may be substituted with one or more groups selected from the group consisting of a sulfanyl group, a hydrocarbon thio group, a hydroxyl group, a carboxyl group, an amino group, an amide group, a guanidino group, an imidazolyl group, a phenyl group, a hydroxyphenyl group, and an indolyl group. Y ２ This represents an oxygen atom or a nitrogen atom. Y ２ When Y is an oxygen atom, m is 1, and R １ is a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or one or more -CH ２ - may be replaced by -O-, -S- or -(SiMe ２ )-, and represents a linear hydrocarbon group having 8 to 18 carbon atoms in which two or more -O- or three or more -S- do not continuously appear. Y ２ If it is a nitrogen atom, then m is 1 or 2, and R １ This is a linear or branched hydrocarbon group having 8 to 24 carbon atoms, or one or more -CH groups. ２ - is -O-, -S- or -(SiMe ２ ) - may be substituted, but it represents a linear hydrocarbon group having 8 to 18 carbon atoms where there are no consecutive -O- or -S- groups. n represents an integer between 0 and 2.

12. The luminescent material according to claim 11, further comprising a π-conjugated compound.

13. The luminescent material according to claim 12, wherein the π-conjugated compound is an aromatic compound having 6 to 20 carbon atoms or a heteroaromatic compound having 3 to 14 carbon atoms.

14. The luminescent material according to claim 11, wherein the content of the leyleneimide compound represented by formula (1) is in the range of 50 to 99.9% by weight.

15. A light-emitting ink comprising a light-emitting material according to any one of claims 11 to 14 and a solvent.

16. The luminescent ink according to claim 15, wherein the solvent is at least one organic solvent selected from the group consisting of C2-C6 alcohols, C6-C10 isoparaffinic hydrocarbons, and C6-C14 alicyclic hydrocarbons, and the content of the luminescent material represented by formula (1) is in the range of 30-70% by weight.

17. A fluorescent paint for inkjet printing, a fluorescent ink for security, a fluorescent ink for writing instruments, a fluorescent dye for clothing, a dye for medical use, a light-emitting material for an electroluminescent element, or a wavelength conversion material, containing the light-emitting material described in any one of claims 11 to 14.

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