Light-emitting compound, method for producing light-emitting compound, polymeric light-emitting compound, light-emitting composition, material for organic device, and organic electroluminescent element

Abstract

To provide a light-emitting compound having a narrow half-value width and a stable skeleton, for example a novel polycyclic aromatic compound applicable to blue light emission, and to provide a method for producing a light-emitting compound that is capable of producing such a polycyclic aromatic compound, preferably using a non-noble metal catalyst, which is suitable for a sustainable society.SOLUTION: According to one embodiment of the present invention, a light-emitting compound is a polycyclic aromatic compound represented by the following formula (I).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a light-emitting compound, a method for producing a light-emitting compound, a polymer light-emitting compound, a light-emitting composition, a material for an organic device, and an organic electroluminescent element. [Background technology]

[0002] Organic electroluminescent devices using organic materials have been studied because of their potential for lightweight and power-saving operation. Examples of such organic electroluminescent devices include OLEDs, OPVs, OFETs, perovskite solar cells, and multilayer thin-film semiconductor devices such as perovskite quantum dots. In multilayer thin-film semiconductor devices, organic semiconductor materials and organic-inorganic semiconductor materials are used as functional molecules such as hole transport materials, hole introduction materials, hole extraction materials, electron transport materials, electron introduction materials, electron extraction materials, and host materials. Fused aromatic rings are widely used as the cores of such functional molecules.

[0003] In particular, blue-emitting compounds, which are one of the three primary colors of light, have been widely studied in order to improve their poor durability and color purity. For example, Patent Document 1 and Non-Patent Document 1 disclose that boron-containing polycyclic aromatic compounds are useful as materials for organic electroluminescent devices. However, due to its Lewis acidity, boron atoms are easily affected by the external environment (water molecules and oxygen), resulting in insufficient weather resistance. Furthermore, boron-containing polycyclic aromatic compounds must be synthesized using a multi-step reaction pathway using a noble metal catalyst, resulting in poor overall yields and requiring complex purification methods to achieve a purity suitable for organic devices. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2023-95774 [Non-patent literature]

[0005] [Non-Patent Document 1] Angew.Chem.Int.Ed.Engl.,2018,57,11316-11320. Summary of the Invention [Problem to be solved by the invention]

[0006] In view of the above circumstances, the present invention aims to provide a luminescent compound having a stable skeleton and a narrow full width half maximum (FWHM, spectral width), for example, a novel polycyclic aromatic compound (particularly, a condensed polycyclic aromatic compound) that can also be used to emit blue light, and a method for producing a luminescent compound suitable for a sustainable society, which can produce such a polycyclic aromatic compound preferably using a non-precious metal catalyst. [Means for solving the problem]

[0007] According to one aspect of the present invention, there is provided a light-emitting compound, which is a polycyclic aromatic compound represented by the following formula (I): [ka] [In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a , R b , R c and R deach independently represents an optionally substituted aromatic hydrocarbon ring group, an optionally substituted aromatic heterocyclic group, an optionally substituted aliphatic hydrocarbon group, an optionally substituted amino group, an optionally substituted silyl group, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a and R b and / or R c and R d may form a ring via a linking group.]

[0008] According to this embodiment, it is possible to provide a light-emitting compound having a fluorescence spectrum with a maximum peak and a narrow half-width, that is, an excellent fluorescence spectrum. DETAILED DESCRIPTION OF THE INVENTION

[0009] Hereinafter, embodiments of the present invention will be described. Various features shown in the following embodiments can be combined with each other. Furthermore, the explanation of the components described below is an example (typical example) of an embodiment of the present invention, and the present invention is not limited to these contents as long as it does not deviate from the gist of the present invention.

[0010] The light-emitting compound of this embodiment is a polycyclic aromatic compound represented by the following formula (I). [ka] [In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a , R b , R c and Rd each independently represents an optionally substituted aromatic hydrocarbon ring group, an optionally substituted aromatic heterocyclic group, an optionally substituted aliphatic hydrocarbon group, an optionally substituted amino group, an optionally substituted silyl group, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a and R b and / or R c and R d may form a ring via a linking group.] Such a luminescent compound can have a fluorescence spectrum with a maximum peak and a narrow half-width, i.e., a superior fluorescence spectrum.

[0011] Each functional group defined in this specification will be explained below. Examples of such functional groups include those described in Kagaku Dojin's "Guide to Naming Organic Compounds" (1990), specifically as follows: In addition, in this specification, functional groups not specifically labeled "divalent" represent "monovalent" functional groups. <Aromatic hydrocarbon ring group> As the aromatic hydrocarbon ring group (aryl group), for example, a group containing an aryl ring having 6 to 30 carbon atoms is preferred, a group containing an aryl ring having 6 to 16 carbon atoms is more preferred, a group containing an aryl ring having 6 to 12 carbon atoms is even more preferred, and a group containing an aryl ring having 6 to 10 carbon atoms is particularly preferred.

[0012] Specific examples of the "aryl ring" include a monocyclic benzene ring, a bicyclic bicyclic bicyclic naphthalene ring and an indene ring, a tricyclic terphenyl ring (m-terphenyl, o-terphenyl, p-terphenyl) and an anthracene ring, fused tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, and anthracene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthacene ring, and chrysene ring, fused pentacyclic perylene ring and pentacene ring, and the like. The fluorene ring, benzofluorene ring, and indene ring also include structures in which a fluorene ring, a benzofluorene ring, a cyclopentane ring, or the like is spiro-bonded, respectively. The fluorene ring, benzofluorene ring, and indene ring also include structures in which two hydrogen atoms of the methylene group in the structure are each substituted with an alkyl group such as a methyl group, resulting in a dimethylfluorene ring, a dimethylbenzofluorene ring, a dimethylindene ring, etc.

[0013] <Aromatic heterocyclic group> As the aromatic heterocyclic group (group containing a heteroaryl ring), for example, a group containing a heteroaryl ring having from 2 to 30 carbon atoms is preferred, a group containing a heteroaryl ring having from 2 to 25 carbon atoms is more preferred, a group containing a heteroaryl ring having from 2 to 20 carbon atoms is even more preferred, a group containing a heteroaryl ring having from 2 to 15 carbon atoms is particularly preferred, and a group containing a heteroaryl ring having from 2 to 10 carbon atoms is most preferred. Furthermore, examples of the "heteroaryl ring" include heterocycles containing, in addition to carbon as ring-constituting atoms, 1 to 5 heteroatoms selected from oxygen atoms, sulfur atoms, nitrogen atoms, selenium atoms, phosphorus atoms, and tellurium atoms.

[0014] Specific examples of the "heteroaryl ring" include a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, an oxadiazole ring (such as a furazan ring), a thiadiazole ring, a triazole ring, a tetrazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, an indole ring, an isoindole ring, a 1H-indazole ring, a benzimidazole ring, a benzoxazole ring, a benzothiazole ring, a 1H-benzotriazole ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, and quinazoline. ring, quinoxaline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiin ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazasiline ring, indolizine ring, furan ring, benzofuran ring, dibenzothiophene ring, thianthrene ring, indolocarbazole ring, benzoindolocarbazole ring, dibenzoindolocarbazole ring, naphthobenzofuran ring, dioxin ring, dihydroacridine ring, xanthene ring, thioxanthene ring, dibenzodioxin ring, benzoselenophene ring, and the like.

[0015] Furthermore, the dihydroacridine ring, xanthene ring, and thioxanthene ring each include structures in which each of the two hydrogen atoms of the methylene group in the structure is substituted with an alkyl group such as a methyl group, resulting in a dimethyldihydroacridine ring, a dimethylxanthene ring, a dimethylthioxanthene ring, etc. Further, bicyclic rings such as a bipyridine ring, a phenylpyridine ring, and a pyridylphenyl ring, and tricyclic rings such as a terpyridyl ring, a bispyridylphenyl ring, and a pyridylbiphenyl ring are also included as "heteroaryl rings". The "heteroaryl ring" also includes a pyran ring.

[0016] <Aliphatic hydrocarbon group> The aliphatic hydrocarbon group (alkyl group) may be either linear or branched, and examples thereof include linear alkyl groups having from 1 to 24 carbon atoms, and branched alkyl groups having from 3 to 24 carbon atoms. Alkyl groups having from 1 to 18 carbon atoms (branched alkyl groups having from 3 to 18 carbon atoms) are preferred, alkyl groups having from 1 to 12 carbon atoms (branched alkyl groups having from 3 to 12 carbon atoms) are more preferred, alkyl groups having from 1 to 6 carbon atoms (branched alkyl groups having from 3 to 6 carbon atoms) are even more preferred, alkyl groups having from 1 to 5 carbon atoms (branched alkyl groups having from 3 to 5 carbon atoms) are particularly preferred, and alkyl groups having from 1 to 4 carbon atoms (branched alkyl groups having from 3 to 4 carbon atoms) are most preferred.

[0017] Specific examples of the "alkyl group" include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a 1-ethyl-1-methylpropyl group, a 1,1-diethylpropyl group, a 1,1,2-trimethylpropyl group, a 1,1,2,2-tetramethylpropyl group, a 1-ethyl-1,2,2-trimethylpropyl group, an n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a 2-ethylbutyl group, a 1,1-dimethylbutyl group, a 3,3-dimethylbutyl group, a 1,1-diethylbutyl group, a 1-ethyl-1-methylbutyl group, a 1-propyl-1-methylbutyl group, a 1,1,3-trimethylbutyl group, a 1-ethyl-1,3-dimethylbutyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl (t-amyl) group, a 1-methylpentyl group, a 2-propylpentyl group, a 1,1-dimethylpentyl group, a 1-ethyl-1-methylpentyl group, a 1-propyl -1-methylpentyl group, 1-butyl-1-methylpentyl group, 1,1,4-trimethylpentyl group, n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 1,1-dimethylhexyl group, 1-ethyl-1-methylhexyl group, 1,1,5-trimethylhexyl group, 3,5,5-trimethylhexyl group, n-butyl group, 1-methylheptyl group, 1-hexylheptyl group, 1,1-dimethylheptyl group, 2,2-dimethylhexyl group Examples include a methylheptyl group, a 2,6-dimethyl-4-heptyl group, an n-octyl group, a t-octyl (1,1,3,3-tetramethylbutyl) group, a 1,1-dimethyloctyl group, an n-nonyl group, an n-decyl group, a 1-methyldecyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, and an n-eicosyl group.

[0018] The alkyl group may be a cyclic alkyl group (cycloalkyl group). The cycloalkyl group is, for example, preferably a cycloalkyl group having 3 to 24 carbon atoms, more preferably a cycloalkyl group having 3 to 20 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms, even more preferably a cycloalkyl group having 3 to 14 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms, particularly preferably a cycloalkyl group having 5 to 10 carbon atoms or a cycloalkyl group having 5 to 8 carbon atoms, and most preferably a cycloalkyl group having 5 to 6 carbon atoms or a cycloalkyl group having 5 carbon atoms.

[0019] Specific examples of the "cycloalkyl group" include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, or a substituent of these groups substituted with an alkyl group having from 1 to 5 carbon atoms or from 1 to 4 carbon atoms (particularly, a methyl group), a bicyclo[1.1.0]butyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.0]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[3.1.0]hexyl group, a bicyclo[2.2.1]heptyl(norbornyl) group, a bicyclo[2.2.2]octyl group, an adamantyl group, a diamantyl group, a decahydronaphthalenyl group, and a decahydroazulenyl group.

[0020] <Substituted Silyl Group> Examples of silyl groups having a substituent (substituted silyl groups) include silyl groups substituted with at least one substituent selected from the group consisting of an aryl group, an alkyl group, and a cycloalkyl group, and a triarylsilyl group, a trialkylsilyl group, a tricycloalkylsilyl group, a dialkylcycloalkylsilyl group, or an alkyldicycloalkylsilyl group is preferred. A "triarylsilyl group" is a silyl group substituted with three aryl groups, and for details of this aryl group, the specific examples given above for the "aryl group" can be cited. Specific examples of "triarylsilyl" include a triphenylsilyl group, a diphenylmononaphthylsilyl group, a monophenyldinaphthylsilyl group, and a trinaphthylsilyl group.

[0021] A "trialkylsilyl group" is a silyl group substituted with three alkyl groups, and for details of this alkyl group, the specific examples given in the above-mentioned "alkyl group" can be cited. Specific examples of the "trialkylsilyl group" include a trimethylsilyl group, a triethylsilyl group, a tri-n-propylsilyl group, a triisopropylsilyl group, a tri-n-butylsilyl group, a triisobutylsilyl group, a tri-s-butylsilyl group, a tri-t-butylsilyl group, an ethyldimethylsilyl group, an n-propyldimethylsilyl group, an isopropyldimethylsilyl group, an n-butyldimethylsilyl group, an isobutyldimethylsilyl group, an s-butyldimethylsilyl group, a t-butyldimethylsilyl group, a methyldiethylsilyl group, an n-propyl Examples thereof include a diethylsilyl group, an isopropyldiethylsilyl group, an n-butyldiethylsilyl group, an s-butyldiethylsilyl group, a t-butyldiethylsilyl group, a methyldi-n-propylsilyl group, an ethyldi-n-propylsilyl group, an n-butyldi-n-propylsilyl group, an s-butyldi-n-propylsilyl group, a t-butyldi-n-propylsilyl group, a methyldiisopropylsilyl group, an ethyldiisopropylsilyl group, an n-butyldiisopropylsilyl group, an s-butyldiisopropylsilyl group, and a t-butyldiisopropylsilyl group.

[0022] A "tricycloalkylsilyl group" is a silyl group substituted with three cycloalkyl groups, and for details of this cycloalkyl group, the specific examples given above for the "cycloalkyl group" can be cited. Specific examples of the "tricycloalkylsilyl group" include a tricyclopentylsilyl group and a tricyclohexylsilyl group. The "dialkylcycloalkylsilyl group" is a silyl group substituted with two alkyl groups and one cycloalkyl group. For details of the alkyl group and the cycloalkyl group, the specific examples given above for the "alkyl group" and the "cycloalkyl group" can be cited. The "alkyldicycloalkylsilyl group" is a silyl group substituted with one alkyl group and two cycloalkyl groups. For details of the alkyl group and the cycloalkyl group, the specific examples given above for the "alkyl group" and the "cycloalkyl group" can be cited.

[0023] <Halogen atom> Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms. From the viewpoint of electron-withdrawing groups, a fluorine atom is preferred as a halogen atom. Furthermore, for carrying out a C—C bond coupling reaction, an iodine or bromine atom is preferred as a halogen atom.

[0024] <Substituent> When the aromatic hydrocarbon ring group, aromatic heterocyclic group, aliphatic hydrocarbon group, or silyl group has a substituent, it may have only one substituent, or may have two or more substituents within the range of allowable substitution positions. Furthermore, the two or more substituents may be the same or different. Examples of this substituent include groups described in Kagaku Dojin's "Guide to Naming Organic Compounds" (1990).

[0025] Examples of the substituent include a halogen atom, a hydroxyl group, a nitro group, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthio group, an arylthio group, a heteroarylthio group, an amino group, an acyl group, an aminoacyl group, a ureido group, a sulfonamido group, a carbamoyl group, a sulfamoyl group, a sulfamoylamino group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heteroaryloxycarbonyl group, an alkylsulfonyl group, an arylsulfonyl group, a heteroarylsulfonyl group, an imido group, and a silyl group.

[0026] Specific examples of the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; alkyl groups having from 1 to about 15 carbon atoms, such as a methyl group and an ethyl group; alkenyl groups having from 2 to about 10 carbon atoms, such as an ethynyl group and a propylenyl group; alkynyl groups having from 2 to about 10 carbon atoms, such as an acetylenyl group; aryl groups having from 6 to about 20 carbon atoms, such as a phenyl group and a naphthyl group; heteroaryl groups having from 3 to about 20 carbon atoms, such as a thienyl group, a furyl group, and a pyridyl group; alkoxy groups having from 1 to about 15 carbon atoms, such as a methoxy group, an ethoxy group, and a propoxy group; aryloxy groups having from 6 to about 20 carbon atoms, such as a phenoxy group and a naphthoxy group; heteroaryloxy groups having from 3 to about 20 carbon atoms, such as a pyridyloxy group and a thienyloxy group; alkylthio groups having from 1 to about 15 carbon atoms, such as a methylthio group and an ethylthio group; and arylthio groups having from 6 to about 20 carbon atoms, such as a phenylthio group and a naphthylthio group.

[0027] Specific examples of the substituent include heteroarylthio groups having from 3 to 20 carbon atoms, such as a pyridylthio group and a thienylthio group; amino groups having from 1 to 20 carbon atoms, such as a dimethylamino group and a diphenylamino group, which may have a substituent; acyl groups having from 2 to 20 carbon atoms, such as an acetyl group and a pivaloyl group; acylamino groups having from 2 to 20 carbon atoms, such as an acetylamino group and a propionylamino group; ureido groups having from 2 to 20 carbon atoms, such as a 3-methylureido group; and methanesulfonyl. and sulfonamido groups having from 1 to 20 carbon atoms such as a benzenesulfonamido group, carbamoyl groups having from 1 to 20 carbon atoms such as a dimethylcarbamoyl group and an ethylcarbamoyl group, sulfamoyl groups having from 1 to 20 carbon atoms such as an ethylsulfamoyl group, sulfamoylamino groups having from 1 to 20 carbon atoms such as a dimethylsulfamoylamino group, and alkoxycarbonyl groups having from 2 to 6 carbon atoms such as a methoxycarbonyl group and an ethoxycarbonyl group.

[0028] Further specific examples of the substituent include aromatic hydrocarbon oxycarbonyl groups having from 7 to 20 carbon atoms, such as a phenoxycarbonyl group and a naphthoxycarbonyl group; aromatic heterocyclic hydrocarbon oxycarbonyl groups having from 6 to 20 carbon atoms, such as a pyridyloxycarbonyl group; alkylsulfonyl groups having from 1 to 6 carbon atoms, such as a methanesulfonyl group, an ethanesulfonyl group, and a trifluoromethanesulfonyl group; arylsulfonyl groups having from 6 to 20 carbon atoms, such as a benzenesulfonyl group and a monofluorobenzenesulfonyl group; heteroaryloxysulfonyl groups having from 3 to 20 carbon atoms, such as a thienylsulfonyl group; imido groups having from 4 to 20 carbon atoms, such as phthalimide; and silyl groups substituted with three substituents selected from the group consisting of alkyl groups and aryl groups.

[0029] R a and R b and a ring formed via a linking group, and R c and R d Specific examples of the ring formed by and via a linking group include the aromatic hydrocarbon ring or aromatic heterocycle as described above, and preferred examples thereof include saturated or unsaturated 5-, 6-, 7-, and 8-membered rings. Specific examples of saturated rings include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Specific examples of the unsaturated ring include a benzene ring, a naphthalene ring, a thiophene ring, a furan ring, and a pyrrole ring.

[0030] The light-emitting compound preferably has a maximum peak FWHM of the fluorescence spectrum in an organic solvent of about 25 nm or less, more preferably about 23 nm or less, even more preferably about 20 nm or less, and particularly preferably about 17 nm or less. The above-mentioned luminescent compound is made from a starting material having five or more fused rings (including aromatic and aliphatic rings) and then the aromatic ring is expanded. Therefore, the structure tends to be "rigid" and vibration is reduced, which is thought to narrow the half-width. At the same time, the nitrogen atom contained in the fused ring is sp 2 To take a hybrid form, sp3 Because they have weaker electron donating properties than hybridized types, they can produce emission maxima with narrow half-widths in a preferred wavelength range. This tendency is thought to be particularly pronounced when fused rings with high molecular symmetry, especially four or more fused rings containing nitrogen, are used as starting materials. Such a luminescent compound can also emit fluorescence with high color purity and sufficient luminescence intensity.

[0031] The lower limit of the half-value width is not particularly limited, but is about 10 nm. Therefore, the half-value width can be set to about 10 nm or more and 25 nm or less. The FWHM of the fluorescence spectrum of the light-emitting compound is measured by the method described in the Examples section below. The light-emitting compound having such a narrow half-width as described above is preferably one that emits fluorescence in any wavelength range, but is particularly preferably one that emits blue fluorescence. Specifically, it is preferable that the maximum peak of the fluorescence spectrum be in a wavelength range of about 430 nm or more and 490 nm or less, more preferably in a wavelength range of about 440 nm or more and 480 nm or less, and even more preferably in a wavelength range of about 445 nm or more and 470 nm or less. The organic solvent used for measuring the fluorescence spectrum may be any solvent that can dissolve the luminescent compound, and examples thereof include halogen-based solvents such as chloroform, dichloromethane, and dichloroethane, and aromatic solvents such as chlorobenzene, dichlorobenzene, and toluene.

[0032] In the method for producing a light-emitting compound of this embodiment, the oxime ether represented by the following formula (II) is reacted with an acetylene derivative in the presence of a catalyst to obtain the light-emitting compound. [ka] [In formula (II), R 9 and R 10each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R e , R f , R g and R h each independently represents an aliphatic hydrocarbon group which may have a substituent, or a silyl group which may have a substituent, and R a , R b , R c and R d each independently represents an optionally substituted aromatic hydrocarbon ring group, an optionally substituted aromatic heterocyclic group, an optionally substituted aliphatic hydrocarbon group, an optionally substituted amino group, an optionally substituted silyl group, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a and R b and / or R c and R d may form a ring via a linking group.] According to the method for producing a light-emitting compound, a light-emitting compound having a stable skeleton can be produced relatively easily.

[0033] Here, the aromatic hydrocarbon ring group, aromatic heterocyclic group, aliphatic hydrocarbon group, amino group, silyl group and substituent are the same as those described above. R e , R f , R g and R h represents an aliphatic hydrocarbon group which may have a substituent, or a silyl group which may have a substituent, and specific examples thereof include the above-mentioned alkyl groups and silyl groups having an alkyl group. Among these, from the viewpoint of reactivity with acetylene derivatives, R e , R f , R g and R h is preferably a methyl group, an ethyl group, or a trimethylsilyl group.

[0034] <Starting material: acetylene derivative> Examples of the acetylene derivative include compounds described in "Modern Acetylene Chemistry" edited by P. Stang, published in 2008, Wiley-VCH; "Acetylene Chemistry: Chemistry, Biology, and Material Science" edited by F. Diederich, published in 2005, Wiley-VCH; and "Synthesis of Acetylenes, Allenes, and Cumulenes" edited by B. Lambert, published in 2004, Elsevier.

[0035] A specific example of the acetylene derivative is preferably a compound represented by the following formula (X). [ka] [In formula (X), R 15 and R 16 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an amino group which may have a substituent, or a silyl group which may have a substituent.

[0036] Here, the aromatic hydrocarbon ring group, aromatic heterocyclic group, aliphatic hydrocarbon group, amino group, silyl group and substituent are the same as those described above. Specific examples of the compound represented by formula (X) include the following compounds. In the following, "Me" represents a methyl group, "Et" represents an ethyl group, "Pr" represents a propyl group, and "TMS" represents a trimethylsilyl group.

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] In the method for producing a luminescent compound, the catalyst preferably contains a trivalent iron compound, a trivalent phosphorus compound, and a trialkylaluminum. The use of such catalysts can sufficiently promote the production of luminescent compounds. Furthermore, these catalysts dissolve in the aqueous layer during post-treatment and can be easily separated from the organic layer containing the product, so they do not interfere with the luminescence of the resulting luminescent compounds. Furthermore, since these catalysts are non-noble metal catalysts, a method for producing luminescent compounds suitable for a sustainable society can be provided.

[0041] <Trivalent iron compounds> The trivalent iron compound that is allowed to coexist in the reaction system means that the iron in the compound is trivalent. Specific examples of trivalent iron compounds include FeCl3, FeBr3, FeI3, Fe(OAc)3, and Fe(acac)3, where "OAc" is an acetoxy group and "acac" is an acetylacetonato group. The amount of the trivalent iron compound to be present in the reaction system is not particularly limited, but is preferably about 1 to 10 equivalents, and more preferably about 1.5 to 5 equivalents, relative to one oxime ether. If the amount of the trivalent iron compound present is equal to or greater than the above lower limit, it is preferred from the viewpoint of the yield of the light-emitting compound (target compound), and if it is equal to or less than the above upper limit, it is preferred from the viewpoint of not reducing the stirring efficiency in the reaction system and of facilitating removal of the iron catalyst after the reaction.

[0042] <Trivalent phosphorus compounds> The trivalent phosphorus compound coexisting in the reaction system means that the phosphorus in the compound is trivalent. For example, triphenylphosphine and tri(o-tolyl)phenylphosphine can be used, but a trivalent phosphorus compound including a compound represented by the following formula (III) is more preferred from the viewpoint of improving the yield of the light-emitting compound.

[0043] [ka] [In formula (III), R 11 and R 12 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aliphatic hydrocarbon group which may have a substituent; Ar 1 represents an aromatic hydrocarbon ring group which may have a substituent, or an aromatic heterocyclic group which may have a substituent.

[0044] Here, the aromatic hydrocarbon ring group, aromatic heterocyclic group, aliphatic hydrocarbon group and substituent are the same as those described above. R 11 and R 12 From the viewpoint of ease of handling of the trivalent phosphorus compound, each of the groups is preferably an aromatic hydrocarbon group which may have a substituent, and more preferably an aromatic hydrocarbon group having a monocyclic aromatic ring (for example, a phenyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a mesityl group, etc.). Ar 1 As the ring, a monocyclic aromatic hydrocarbon ring group, a bicondensed aromatic hydrocarbon ring group, or a bicondensed aromatic heterocyclic ring is preferred. As the trivalent phosphorus compound, the specific compounds shown below are more preferred.

[0045] [ka] Here, "Ph" represents a phenyl group, and "Tol" represents a tolyl group.

[0046] The trivalent phosphorus compound also functions as a ligand for the trivalent iron compound, and its coexistence amount in the reaction system is preferably about 1 equivalent or more and 5 equivalents or less, and more preferably about 1.1 equivalents or more and 3.3 equivalents or less, per mol of the trivalent iron compound. When the amount of the trivalent phosphorus compound present is equal to or greater than the lower limit, the reaction is initiated significantly, whereas when the amount is equal to or less than the upper limit, purification is facilitated, which is preferable.

[0047] <Trialkylaluminum> The alkyl group of the trialkylaluminum to be present in the reaction system is generally, for example, a methyl group, an ethyl group, an isobutyl group, etc., but an isopropyl group or an isobutyl group, which have high steric hindrance, is preferred. By using a trialkylaluminum having such an alkyl group with high steric hindrance, the yield of the light-emitting compound can be increased.

[0048] The amount of trialkylaluminum coexisting in the reaction system is preferably about 10 to 50 equivalents, more preferably about 20 to 30 equivalents, per mol of the trivalent iron compound. If the amount of trialkylaluminum present is equal to or greater than the lower limit, the reaction will start remarkably, whereas if it is equal to or less than the upper limit, the post-treatment procedure for deactivating the trialkylaluminum after the reaction will be easy.

[0049] <Catechol> The reaction system may contain additives other than the trivalent iron compound, the trivalent phosphorus compound, and the trialkylaluminum. Specifically, in the method for producing a light-emitting compound, the reaction is preferably carried out in the presence of a bidentate catechol, which coordinates with the trialkylaluminum, thereby driving the iron catalytic cycle.

[0050] When catechol is used, the amount of catechol to be coexisted in the reaction system is preferably about 10 equivalents or more and 50 equivalents or less, and more preferably about 20 equivalents or more and 30 equivalents or less, per mol of the trivalent iron compound.

[0051] <Solvent> In the method for producing a luminescent compound, the reaction is preferably carried out in the presence of at least one reaction solvent selected from the group consisting of ether solvents, aromatic solvents, and halogenated solvents, which can further increase the production efficiency of the luminescent compound. Specific examples of ether solvents include tetrahydrofuran (THF), cyclopentyl methyl ether (CPME), 2-methyltetrahydrofuran (MTHF), and methyl tert-butyl ether (MTBE). Specific examples of aromatic solvents include xylene and toluene. Specific examples of halogenated solvents include dichloromethane, dichloroethane, chlorobenzene, and dichlorobenzene.

[0052] As the reaction solvent, one of the above solvents may be used alone, or two or more of them may be used in combination (mixed). For example, when a solvent with low solubility of the substrate, etc. is used, the reaction results are improved by combining it with a halogenated solvent or an ether solvent. Also, when a high-boiling point solvent is used to increase the reaction temperature, the reaction results are improved by preferably combining it with an aromatic solvent.

[0053] <Reaction conditions> The reaction is preferably carried out at a reaction temperature ranging from about -5°C or higher, preferably about 0°C or higher, more preferably about 10°C or higher, and particularly preferably about 25°C or higher to the boiling point of the solvent used. The reaction temperature can be set arbitrarily up to the reflux temperature of the solvent used, depending on the rate of reaction progression. In particular, it is preferable to carry out the reaction using a solvent with a boiling point of 100°C or higher and 150°C or lower, as this increases the rate of production of the luminescent compound. When the yield of the light-emitting compound is not sufficient, the reaction solution may be irradiated with ultrasonic waves or microwaves, or an autoclave may be used to heat the reaction solution.

[0054] The reaction time is usually about 30 minutes to 48 hours, but may be set arbitrarily since it depends on the type of solvent used and other reaction conditions. The degree of progress of the reaction is confirmed using thin layer chromatography (TLC), high performance liquid chromatography (HPLC), or the like, and it is preferable to carry out post-treatment immediately after the end point of the reaction is confirmed. After the reaction is complete, the luminescent compound can be recovered (isolated and purified) using a conventional work-up method. From the viewpoint of removing trivalent iron compounds, the recovery operation is preferably carried out by liquid separation extraction using a dilute aqueous hydrochloric acid solution.

[0055] <Starting material: oxime ether> Specific examples (skeleton examples) of carbonyl compounds used as starting materials for obtaining oxime ethers to be subjected to the above reaction are shown below. As shown here, the oxime ether skeleton may contain an electron transport group or a hole transport group, or may contain a halogen atom or a triflate group and introduce an electron transport group or a hole transport group in an intermediate step. However, the starting materials are not limited to these.

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka]

[0061] <Method of producing oxime ether> The oxime ether used as the raw material compound can be produced by using the above carbonyl compound as a starting material and converting the carbonyl group of the carbonyl compound into an oxime ether group. The carbonyl group can be converted into an oxime ether group, for example, by the method described in "The Chemistry of Hydroamines, Oximes and Hydroxamic Acids" by Rappoport (2009, John Wiley & Sons).

[0062] Specifically, the oxime ether can be obtained by reacting a carbonyl compound with hydroxylamine (or a derivative thereof) to convert the carbonyl group into an oxime ether group, preferably in the presence of an organic base and a Lewis acid. Examples of the organic base include triethylamine, triisopropylamine, diisopropylamine, pyridine, 2,6-dimethylpyridine, 2,4-dimethylpyridine, 2,6-tert-butylpyridine, piperidine, and pyrrolidine. Examples of Lewis acids include titanium (IV) chloride, aluminum (III) chloride, ZnCl2, BF3-Et2O, and SnCl4.

[0063] <Luminescent compound (target compound)> Specific examples of the luminescent compound are shown below. However, the luminescent compound is not limited to these.

[0064] [ka]

[0065] [ka]

[0066] In the following compounds, R I and R IIare each independently the R I and R II is selected from. [ka]

[0067] In the following compounds, R I and R II are each independently the R I and R II is selected from. [ka]

[0068] The light-emitting polymer compound of this embodiment is a conjugated polymer having the light-emitting compound as a unit. The weight-average molecular weight (Mw) of the conjugated polymer is preferably about 10 K or more and 100 K or less, and more preferably about 15 K or more and 100 K or less from the viewpoint of solubility. These conjugated polymers can be adjusted to a desired molecular weight by CC or C-H coupling reaction.

[0069] In an organic solvent, the polymeric light-emitting compound preferably has a FWHM of the maximum peak of its fluorescence spectrum of about 25 nm or less, more preferably about 23 nm or less, even more preferably about 20 nm or less, and particularly preferably about 17 nm or less. The lower limit of the half-width is not particularly limited, but is about 10 nm. Therefore, the half-width can be about 10 nm or more and 25 nm or less. Such a polymeric light-emitting compound can emit fluorescence with high color purity and sufficient luminescence intensity. The polymer light-emitting compound having such a narrow half-width as described above is preferably one that emits fluorescence in any wavelength range, but is particularly preferably one that emits blue fluorescence. Specifically, it is preferable that the maximum peak of the fluorescence spectrum be in the wavelength range of about 430 nm or more and 490 nm or less, more preferably in the wavelength range of about 440 nm or more and 480 nm or less, and even more preferably in the wavelength range of about 445 nm or more and 470 nm or less. The organic solvent used for measuring the fluorescence spectrum may be any as long as it can dissolve the polymer light-emitting compound, and examples thereof include halogen-based solvents such as chloroform, dichloromethane, and dichloroethane, and aromatic solvents such as chlorobenzene, dichlorobenzene, and toluene.

[0070] The light-emitting composition of the present embodiment contains the light-emitting compound or the light-emitting polymer compound. This makes it possible to obtain a light-emitting composition with excellent light-emitting properties.

[0071] The material for an organic device of this embodiment contains the above-mentioned light-emitting compound or the above-mentioned polymer light-emitting compound. This makes it possible to obtain a material for an organic device having excellent light-emitting properties.

[0072] The organic electroluminescent device of this embodiment contains the above-mentioned light-emitting compound or the above-mentioned polymer light-emitting compound. This provides an organic electroluminescent device with excellent light-emitting properties. An organic light-emitting element has, for example, an anode, a cathode, a light-emitting layer provided between them, a layer having a hole transport function (hole transport layer) provided between the light-emitting layer and the anode, and a layer having an electron transport function (electron transport layer) provided between the light-emitting layer and the cathode. The light-emitting layer contains the light-emitting compound or the polymer light-emitting compound. The hole-transporting layer may contain, for example, a hole-transporting material or a hole-introducing material. The electron-transporting layer may contain, for example, an electron-transporting material or an electron-introducing material.

[0073] As described above, various embodiments of the present invention have been described, but these are presented as examples and do not limit the scope of the invention in any way. The novel embodiments can be embodied in various other forms, and various omissions, substitutions, and modifications can be made without departing from the spirit of the invention. Such embodiments and their modifications are intended to be included within the scope and spirit of the invention, as well as within the scope of the inventions and their equivalents as set forth in the claims.

[0074] Furthermore, it may be provided in the following aspects.

[0075] (1) A light-emitting compound, which is a polycyclic aromatic compound represented by the following formula (I): [ka] [In formula (I), R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a , R b , R c and R d each independently represents an optionally substituted aromatic hydrocarbon ring group, an optionally substituted aromatic heterocyclic group, an optionally substituted aliphatic hydrocarbon group, an optionally substituted amino group, an optionally substituted silyl group, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a and R b and / or R c and R d may form a ring via a linking group.]

[0076] (2) The light-emitting compound according to (1) above, wherein the full width at half maximum of the maximum peak of the fluorescence spectrum in an organic solvent is 25 nm or less.

[0077] (3) A method for producing the luminescent compound according to (1) or (2) above, comprising reacting an oxime ether represented by the following formula (II) with an acetylene derivative in the presence of a catalyst to obtain the luminescent compound: [ka] [In formula (II), R 9 and R 10 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R e , R f , R g and R h each independently represents an aliphatic hydrocarbon group which may have a substituent, or a silyl group which may have a substituent, and R a , R b , R c and R d each independently represents an optionally substituted aromatic hydrocarbon ring group, an optionally substituted aromatic heterocyclic group, an optionally substituted aliphatic hydrocarbon group, an optionally substituted amino group, an optionally substituted silyl group, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R a and R b and / or R c and R d may form a ring via a linking group.]

[0078] (4) The method for producing a luminescent compound according to (3) above, wherein the catalyst contains a trivalent iron compound, a trivalent phosphorus compound, and a trialkylaluminum.

[0079] (5) The method for producing a luminescent compound according to (4) above, wherein the trivalent phosphorus compound includes a compound represented by the following formula (III): [ka] [In formula (III), R 11 and R 12 each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aliphatic hydrocarbon group which may have a substituent; Ar 1 represents an aromatic hydrocarbon ring group which may have a substituent, or an aromatic heterocyclic group which may have a substituent.

[0080] (6) The method for producing a luminescent compound according to (4) or (5) above, wherein the reaction is carried out further in the presence of a bidentate catechol.

[0081] (7) The method for producing a luminescent compound according to any one of (3) to (6) above, wherein the reaction is carried out in the presence of at least one reaction solvent selected from the group consisting of ether solvents, aromatic solvents, and halogenated solvents.

[0082] (8) A polymer light-emitting compound, which is a conjugated polymer having the light-emitting compound according to (1) or (2) as a unit, and the weight-average molecular weight (Mw) of the conjugated polymer is 10K or more and 100K or less.

[0083] (9) The polymer light-emitting compound according to (8) above, wherein the half-width of the maximum peak of the fluorescence spectrum in an organic solvent is 25 nm or less.

[0084] (10) A light-emitting composition, comprising the light-emitting compound according to (1) or (2) above, or the polymer light-emitting compound according to (8) or (9).

[0085] (11) A material for an organic device, comprising the light-emitting compound according to (1) or (2) above, or the polymer light-emitting compound according to (8) or (9).

[0086] (12) An organic electroluminescent device, comprising the light-emitting compound according to (1) or (2) above, or the polymer light-emitting compound according to (8) or (9). Of course, this is not the case. [Example]

[0087] Hereinafter, embodiments of the light-emitting compound will be described in more detail with reference to examples, but the light-emitting compound is not limited to the following examples as long as it does not depart from the gist of the compound.

[0088] 1. Measurement 1-1. High resolution mass spectrometry (HRMS) The produced compounds were identified using TOF-MS spectra (model number: Shimadzu LCMS-IT-TOF).

[0089] 1-2.Measuring method for the wavelength (λem) of the maximum peak of the fluorescence spectrum and its full width at half maximum (FWHM) Absorption spectrum (in dichloromethane, approximately 1.0 × 10 -5 The fluorescence spectrum (in dichloromethane, approximately 1.0 × 10 -6 M or approximately 1.0 x 10 -7 The absolute luminescence quantum yields were measured on a Hamamatsu Photonics C9920-02 spectrometer equipped with an integrating sphere. Dichloromethane for spectroscopic analysis (Fujifilm Wako Pure Chemical Industries, Ltd.) was used.

[0090] 2. Preparation of oxime ethers Pentacene-5,7,12,14-tetraone (677 mg, 2.0 mmol), O-methylhydroxylamine hydrochloride (1.7 g, 20 mmol), dehydrated pyridine (5.0 mL), and dehydrated dichloromethane (20 mL) were mixed in an oven-dried Schlenk tube. Then, a solution of TiCl4 in toluene (1.0 mol / L, 5.0 mL, 5.0 mmol) was added at room temperature.

[0091] The reaction mixture was stirred for 24 hours at 100° C. After completion of the reaction, the reaction mixture was cooled to room temperature, carefully diluted with dichloromethane (20 mL), and quenched with water (20 mL). The aqueous layer was extracted with dichloromethane (20 mL × 3), and the solvent in the combined organic layers was removed under reduced pressure. The resulting crude product was purified by silica gel chromatography (eluent: hexane / dichloromethane) to give the following oxime ether in 92% yield.

[0092] [ka] HRMS (ESI+): m / z calculated for C 26 H 22 N4O4[M+H + ] 455.1714; found: 455.1709.

[0093] 3. Preparation of Luminescent Compounds (General manufacturing example) In an oven-dried Schlenk tube, tetramethyltetraoxime (0.5 mmol), the acetylene derivative (3 mmol), catechol (4 mmol), TP1 (0.22 mmol), Fe(acac) (0.20 mmol), and xylene (4 mL) were added under a stream of argon. Then, a solution of Al(i-Bu) in toluene (1.0 mol / L, 4 mL, 4 mmol) was added at room temperature, and the reaction mixture was stirred at room temperature for 5 minutes, then heated at 140°C for 24 hours.

[0094] The reaction mixture was cooled to room temperature, diluted with dichloromethane (20 mL), and excess Al(i-Bu)3 was quenched with methanol (1 mL). The reaction mixture was diluted with dichloromethane and vigorously stirred until all the crude product was dissolved. The mixture was poured into a mixture of 300 mL of methanol and 30 mL of triethylamine, and a yellow precipitate immediately formed. The resulting precipitate was filtered and washed with a mixture of methanol (200 mL) and triethylamine (20 mL) to obtain the luminescent compound.

[0095] [ka]

[0096] Example 1 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and diphenylacetylene was used as the acetylene derivative, and the following example compound 1 was obtained as a light-emitting compound in 80% yield.

[0097] [ka] HRMS (ESI+): m / z scaled for C 78 H 46 N4[M+H] 1039.3795; found: 1039.3755.

[0098] Example 2 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 2 was used as the acetylene derivative, and the following example compound 2 was obtained as a light-emitting compound in 76% yield. [ka]

[0099] [ka] HRMS (ESI+): m / z scaled for C 86 H 62 N4[M+H] 1151.5053; found: 1151.5028.

[0100] Example 3 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 3 was used as the acetylene derivative, and the following example compound 3 was obtained as a light-emitting compound in 82% yield. [ka]

[0101] [ka] HRMS (ESI+): m / z scaled for C 62 H 30 N4S8[M+H] 1087.0314; found: 1087.0321.

[0102] Example 4 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 4 was used as the acetylene derivative, and the following example compound 4 was obtained as a light-emitting compound in a yield of 76%. [ka]

[0103] [ka] HRMS (ESI+): m / z scaled for C 54 H 62 N4[M+H] 767.5053; found: 767.5074.

[0104] Example 5 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 5 was used as the acetylene derivative, and the following example compound 5 was obtained as a light-emitting compound in 84% yield. [ka]

[0105] [ka] HRMS (ESI+): m / z scaled for C 66 H 62 N4Si4[M+H] 1023.4130; found: 1023.4089.

[0106] Example 6 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 6 was used as the acetylene derivative, and the following example compound 6 was obtained as a light-emitting compound in 81% yield. [ka]

[0107] [ka] HRMS (ESI+): m / z caled for C86H62N4 [M+H] 1151.5053; found: 1151.5066.

[0108] Example 7 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 7 was used as the acetylene derivative, to obtain the following example compound 7 as a light-emitting compound in a yield of 77%. [ka]

[0109] [ka] HRMS (ESI+): m / z scaled for C 78 H 94 N4[M+H] 1087.7557; found: 1087.7541.

[0110] Example 8 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 8 was used as the acetylene derivative, to obtain the following example compound 8 as a light-emitting compound in 81% yield. [ka]

[0111] [ka] HRMS (ESI+): m / z scaled for C 94 H 78 N4[M+H] 1264.6338; found: 1264.6323.

[0112] Example 9 The reaction was carried out in the same manner as in the general production example, except that the compound 1 produced above was used as the tetramethyltetraoxime and the following compound 9 was used as the acetylene derivative, to obtain the following example compound 9 as a light-emitting compound in 71% yield. [ka]

[0113] [ka] HRMS (ESI+): m / z scaled for C 54 H 78 N8Si8[M+H] 1007.4459; found: 1007.4465.

[0114] (Comparative Example) The comparative compound (TBN-TPA) shown below was produced according to the method described in Angew. Chem. Int. Ed. Engl., 2018, 57, 11316-11320.

[0115] [ka]

[0116] The measurement results for the obtained luminescent compound are shown in Table 1 below. [Table 1]

Claims

1. A light-emitting compound comprising: A light-emitting compound which is a polycyclic aromatic compound represented by the following formula (I): 【Chemistry 1】 [In formula (I), R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ９ and R １０ each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R ａ , R ｂ , R ｃ and R ｄ each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an amino group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R ａ and R ｂ and / or R ｃ and R ｄ may form a ring via a linking group.

2. 2. The luminescent compound of claim 1, A luminescent compound having a fluorescence spectrum with a maximum peak half-width of 25 nm or less in an organic solvent.

3. A method for producing the luminescent compound according to claim 1 or claim 2, comprising: A method for producing a luminescent compound, comprising reacting an oxime ether represented by the following formula (II) with an acetylene derivative in the presence of a catalyst to obtain the luminescent compound: 【Chemistry 2】 [In formula (II), R ９ and R １０ each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R ｅ , R ｆ , R ｇ and R ｈ each independently represents an aliphatic hydrocarbon group which may have a substituent, or a silyl group which may have a substituent; R ａ , R ｂ , R ｃ and R ｄ each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, an aliphatic hydrocarbon group which may have a substituent, an amino group which may have a substituent, a silyl group which may have a substituent, a nitrile group, a nitro group, a halogen atom, or a hydrogen atom; R ａ and R ｂ and / or R ｃ and R ｄ may form a ring via a linking group.

4. 4. The method for producing a luminescent compound according to claim 3, A method for producing a luminescent compound, wherein the catalyst comprises a trivalent iron compound, a trivalent phosphorus compound, and a trialkylaluminum.

5. 5. The method for producing a luminescent compound according to claim 4, The method for producing a light-emitting compound, wherein the trivalent phosphorus compound includes a compound represented by the following formula (III): 【Transformation 3】 [In formula (III), R １１ and R １２ each independently represents an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aliphatic hydrocarbon group which may have a substituent; Ar １ represents an aromatic hydrocarbon ring group which may have a substituent, or an aromatic heterocyclic group which may have a substituent.]

6. 5. The method for producing a luminescent compound according to claim 4, The method for producing a light-emitting compound, wherein the reaction is further carried out in the presence of a bidentate catechol.

7. 4. The method for producing a luminescent compound according to claim 3, The method for producing a light-emitting compound comprises carrying out the reaction in the presence of at least one reaction solvent selected from the group consisting of ether solvents, aromatic solvents, and halogenated solvents.

8. A polymeric light-emitting compound, A conjugated polymer having the light-emitting compound according to claim 1 or 2 as a unit, The polymer light-emitting compound, wherein the weight average molecular weight (Mw) of the conjugated polymer is 10K or more and 100K or less.

9. The polymeric light-emitting compound according to claim 8, A polymeric light-emitting compound having a fluorescence spectrum maximum peak half-width of 25 nm or less in an organic solvent.

10. 1. A light-emitting composition comprising: A light-emitting composition comprising the light-emitting compound according to claim 1 or claim 2, or the light-emitting polymer compound according to claim 8 or claim 9.

11. A material for an organic device, comprising: A material for an organic device, comprising the light-emitting compound according to claim 1 or 2, or the polymer light-emitting compound according to claim 8 or 9.

12. An organic electroluminescent device, An organic electroluminescent device comprising the light-emitting compound according to claim 1 or 2, or the polymer light-emitting compound according to claim 8 or 9.

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