Metal complex, composition, film and light-emitting device

Abstract

To provide a metal complex with a narrow emission spectrum width.SOLUTION: The invention provides a compound represented by formula (1). In the formula, M represents an iridium atom or the like; n1 represents 1 to 3; n2 represents 0 to 2; ring RC1, ring RC2 and ring RC3 represent aromatic rings or the like; X1 and X2 represent groups represented by -C(RX)2-; RX represents a hydrogen atom or the like; and A1-G1-A2 represents an anionic bidentate ligand.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a metal complex (specifically, a metal complex having luminescence properties), and a composition, a film, and a light-emitting device containing the metal complex. [Background technology]

[0002] Light-emitting elements such as organic electroluminescence elements can be suitably used for display and lighting applications. For example, Non-Patent Document 1 proposes a metal complex CM2 represented by the following formula as a light-emitting material for use in light-emitting elements. In addition, for example, Patent Document 1 proposes a metal complex 1 represented by the following formula as a light-emitting material for use in light-emitting elements.

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2002-066552 [Non-patent literature]

[0005] [Non-Patent Document 1] MA Baldo et al., "Very high-efficiency green organic light-emitting devices based on electrophosphorescence", Applied Physics Letters, 75, 4 (1999), pp. 4-6 Summary of the Invention [Problem to be solved by the invention]

[0006] However, the emission spectrum width of the above metal complexes was not sufficiently narrow. Therefore, an object of the present invention is to provide a metal complex having a narrow emission spectrum width. Another object of the present invention is to provide a composition containing the metal complex, a film containing the metal complex, and a light-emitting device containing the metal complex. [Means for solving the problem]

[0007] Conventionally (for example, when the metal complex described in the above document is used in a light-emitting element), the emission spectrum width of the light-emitting element was not narrow enough, and it was necessary to reduce the extra emission color other than the desired emission color. Therefore, the present inventors focused on utilizing the emission that was conventionally reduced in the light-emitting element, and thought that by narrowing the emission spectrum width of the metal complex to narrow the emission spectrum width of the light-emitting element, the reduced emission can be reduced and more emission can be utilized in the light-emitting element, thereby obtaining a light-emitting element with excellent emission characteristics such as luminous efficiency. Based on the above idea, the present inventors conducted extensive research and found that the emission spectrum width of the metal complex can be narrowed by satisfying a specific structure, and thus completed the present invention. That is, the present invention provides the following.

[0008] A metal complex represented by formula (1).

[0009] [ka]

[0010] [In the formula, M represents a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1 represents 1, 2 or 3; n 2 represents 0, 1, or 2. However, when M is a rhodium atom or an iridium atom, n 1 +n 2 is 3, and when M is a platinum atom or a palladium atom, n 1 +n 2 is 2. Ring RC1 represents an aromatic heterocycle, and the aromatic heterocycle may have a substituent. C1 When multiple are present, they may be the same or different. Ring R C2 represents a monocyclic aromatic hydrocarbon ring, a monocyclic aromatic heterocycle, or a fused ring formed by condensing two or more rings selected from the group consisting of a monocyclic aromatic hydrocarbon ring and a monocyclic aromatic heterocycle, and these rings may have a substituent. C2 When multiple are present, they may be the same or different. Ring R C3 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. C2 When multiple are present, they may be the same or different. X 1 and X 2 are each independently -C(R X ) 2 - represents a group represented by the formula: R X represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, or two R x These groups may have a substituent. x may be the same or different. A 1 -G 1 -A 2 represents an anionic bidentate ligand. 1 is a single bond or A 1 and A 2 Represents an atomic group that, together with A, constitutes a bidentate ligand. 1 and A 2 each independently represents a carbon atom, an oxygen atom, or a nitrogen atom, or an atomic group having any of them, and these atomic groups may be atomic groups constituting a ring.

[0011] Ring R C2is a benzene ring, a pyridine ring or a diazabenzene ring, and these rings may have a substituent.

[0012] Ring R C3 is a benzene ring, a pyridine ring or a diazabenzene ring, and these rings may have a substituent.

[0013] Ring R C1 is a pyridine ring or a diazabenzene ring, and these rings may have a substituent.

[0014] Ring R C2 Any of the above metal complexes, at least one of which has a group represented by formula (DA), formula (DB) or formula (DC) as a substituent.

[0015] [ka]

[0016] [In the formula, m DA1 , m DA2 and m DA3 each independently represents an integer of 0 or greater. G DA represents a nitrogen atom, a trivalent aromatic hydrocarbon group, or a trivalent heterocyclic group, and these groups may have a substituent. Ar DA1 , Ar DA2 and Ar DA3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 and Ar DA3 When multiple are present, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]

[0017] [ka]

[0018] [In the formula, m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 each independently represents an integer of 0 or greater. G DA represents a nitrogen atom, a trivalent aromatic hydrocarbon group, or a trivalent heterocyclic group, and these groups may have a substituent. DA may be the same or different. Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 When multiple are present, they may be the same or different. T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]

[0019] [ka]

[0020] [In the formula, m DA1 represents an integer greater than or equal to 0; Ar DA1represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ar DA1 When more than one is present, they may be the same or different; T DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.]

[0021] Any of the above metal complexes, which is a metal complex represented by formula (1-1):

[0022] [ka]

[0023] [In the formula, M, n 1 , n 2 , R X and A 1 -G 1 -A 2 has the same meaning as above; R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R C21 , R C22 , R C23 and R C24 R each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R C21 , R C22 , R C23 and R C24 When multiple are present, they may be the same or different.

[0024] R C21 , R C22 , RC23 and R C24 At least one of the above is a group represented by formula (DA).

[0025] R X Any of the above metal complexes, wherein R is a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups may have a substituent.

[0026] M is an iridium atom, n 1 Any of the above metal complexes, wherein

[0027] Any of the above metal complexes, At least one compound selected from the group consisting of compounds represented by formula (H-1) and polymer compounds containing a structural unit represented by formula (Y), A composition comprising:

[0028] [ka]

[0029] [In the formula, Ar H1 and Ar H2 each independently represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. n H1 and n H2 Each independently represents 0 or 1. H1 When there are multiple n's, they may be the same or different. H2 may be the same or different. n H3 represents an integer greater than or equal to 0. L H1 represents an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. H1 When multiple are present, they may be the same or different. L H2 -N(-R H21)-represents a group represented by L H2 When there are multiple R, they may be the same or different. H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

[0030] [ka]

[0031] [In the formula, Ar Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded to each other, and these groups may have a substituent.]

[0032] Any of the above metal complexes, at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent; A composition comprising:

[0033] A film containing any one of the above metal complexes.

[0034] A light-emitting device containing any one of the above metal complexes. Effect of the Invention

[0035] According to the present invention, a metal complex having a narrow emission spectrum can be provided. Furthermore, according to the present invention, a composition containing the metal complex, a film containing the metal complex, and a light-emitting device containing the metal complex can be provided. The emission spectrum of the composition, film, and light-emitting device containing the metal complex of the present invention is narrow. [Brief description of the drawings]

[0036] [Figure 1] 1 is a graph showing an emission spectrum of a metal complex M1 of Example 1, an emission spectrum of a metal complex CM1 of Comparative Example 1, and an emission spectrum of a metal complex CM2 of Comparative Example 2. [Diagram 2] 1 is a graph in which the peaks of the emission spectra of metal complexes CM1 and CM2 of Comparative Examples 1 and 2 are superimposed on the peak positions of the emission spectra of metal complexes M1 and M1 of Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0037] Preferred embodiments of the present invention will now be described in detail.

[0038] <Explanation of common terms> Terms commonly used in this specification have the following meanings unless otherwise specified.

[0039] Me represents a methyl group, Et represents an ethyl group, t-Bu represents a tert-butyl group, Bu represents a butyl group, and Ph represents a phenyl group.

[0040] The hydrogen atom may be a deuterium atom or a protium atom. In the formula representing a metal complex, the solid line representing a bond to a central metal means an ionic bond, a covalent bond or a coordinate bond.

[0041] "Polymer compounds" are compounds that have a molecular weight distribution and have a number average molecular weight of 1 x 10 3 or more (e.g., 1×10 3 ~1×10 8 ) means a polymer in which The polymer compound may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms. The end group of the polymer compound is preferably a stable group, since if the polymerization active group remains as it is, the light-emitting properties or luminance life may be reduced when the polymer compound is used to prepare a light-emitting device. The end group of the polymer compound is preferably a group that is conjugated with the main chain, and examples of the end group include an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond. The term "structural unit" refers to a unit that exists in a polymer compound, one or more of which are present.

[0042] A "low molecular weight compound" is a compound that does not have a molecular weight distribution and has a molecular weight of 1×10 4 The following compound is meant:

[0043] The "alkyl group" may be either linear or branched. The number of carbon atoms in a linear alkyl group, not including the number of carbon atoms in the substituent, is usually 1 to 50, preferably 1 to 30, and more preferably 1 to 10. The number of carbon atoms in a branched alkyl group, not including the number of carbon atoms in the substituent, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 10. The alkyl group may have a substituent. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isoamyl group, a 2-ethylbutyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a 3-propylheptyl group, a decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, a 2-hexyldecyl group, a dodecyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like (for example, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3-(4-methylphenyl)propyl group, a 3-(3,5-di-hexylphenyl)propyl group, and a 6-ethyloxyhexyl group). The number of carbon atoms in a "cycloalkyl group", not including the number of carbon atoms in the substituent, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 10. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0044] The term "aryl group" refers to an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in the aryl group, not including the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18, and even more preferably 6 to 10. The aryl group may have a substituent. Examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, a 4-phenylphenyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc. The aryl group includes a group in which a plurality of these groups are bonded.

[0045] The "alkoxy group" may be either linear or branched. The number of carbon atoms of a linear alkoxy group, not including the number of carbon atoms of the substituent, is usually 1 to 40, and preferably 4 to 10. The number of carbon atoms of a branched alkoxy group, not including the number of carbon atoms of the substituent, is usually 3 to 40, and preferably 4 to 10. The alkoxy group may have a substituent. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, a lauryloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. The number of carbon atoms of the "cycloalkoxy group", not including the number of carbon atoms of the substituent, is usually 3 to 40, and preferably 4 to 10. The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group.

[0046] The number of carbon atoms in the "aryloxy group", not including the number of carbon atoms of the substituent, is usually 6 to 60, and preferably 6 to 48. The aryloxy group may have a substituent. Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracynyloxy group, a 9-anthracynyloxy group, a 1-pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.

[0047] The term "aromatic hydrocarbon group" refers to an atomic group remaining after removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. For example, a "trivalent aromatic hydrocarbon group" refers to an atomic group remaining after removing three hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the aromatic hydrocarbon group, not including the number of carbon atoms of the substituent, is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18. The aromatic hydrocarbon group may have a substituent. Examples of aromatic hydrocarbon groups include groups in which one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring are removed from benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, naphthacene, fluorene, pyrene, perylene, or chrysene, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents. The aromatic hydrocarbon group includes groups in which a plurality of these groups are bonded.

[0048] The term "arylene group" refers to an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in the arylene group, not including the number of carbon atoms in the substituent, is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18. The arylene group may have a substituent. Examples of the arylene group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, a chrysenediyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents. The arylene group is preferably a group represented by formula (A-1) to formula (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

[0049] [ka]

[0050] [ka]

[0051] [ka]

[0052] [ka] [Wherein, R and R a each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. a may be the same or different, R a may be bonded to each other to form a ring together with the atoms to which they are bonded.

[0053] The term "P-valent heterocyclic group" (P is an integer of 1 or more) refers to an atomic group remaining after removing P hydrogen atoms from among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring of a heterocyclic compound. Among the P-valent heterocyclic groups, a "P-valent aromatic heterocyclic group" which is an atomic group remaining after removing P hydrogen atoms from among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring of an aromatic heterocyclic compound is preferred. The term "aromatic heterocyclic compound" refers to a compound in which the heterocycle itself exhibits aromaticity, such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, or dibenzophosphole, and a compound in which an aromatic ring is condensed with a heterocycle, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, or benzopyran, even if the heterocycle itself does not exhibit aromaticity. The number of carbon atoms of the P-valent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 20, not including the number of carbon atoms of the substituent. The P-valent heterocyclic group may have a substituent. Examples of the P-valent heterocyclic group include groups in which one or more hydrogen atoms have been removed from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, or triazole, among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents. The P-valent heterocyclic group includes a group in which a plurality of these groups are bonded. Among the p-valent heterocyclic groups, examples of monovalent heterocyclic groups include a thienyl group, a pyrrolyl group, a furyl group, a pyridinyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, a triazinyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like. The number of carbon atoms of the divalent heterocyclic group, not including the number of carbon atoms of the substituent, is usually 2 to 60, preferably 3 to 20, more preferably 4 to 20, and further preferably 4 to 15. The divalent heterocyclic group may have a substituent. Examples of the divalent heterocyclic group include divalent groups obtained by removing two hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring of pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, or triazole, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents. The divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

[0054] [ka]

[0055] [ka]

[0056] [ka]

[0057] [ka]

[0058] [ka]

[0059] [ka]

[0060] [ka] [Wherein, R and R a has the same meaning as above.]

[0061] The term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0062] The "amino group" may have a substituent, and a substituted amino group is preferable. The substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. The substituted amino group is preferably a disubstituted amino group. Examples of the disubstituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group. Examples of the substituted amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis(4-methylphenyl)amino group, a bis(4-tert-butylphenyl)amino group, and a bis(3,5-di-tert-butylphenyl)amino group.

[0063] The "crosslinking group" is a group capable of generating a new bond by being subjected to heating, ultraviolet light irradiation, near-ultraviolet light irradiation, visible light irradiation, infrared light irradiation, radical reaction, etc. The crosslinking group is preferably a crosslinking group represented by formulae (XL-1) to (XL-19).

[0064] [ka] [In the formula, R XL represents a methylene group, an oxygen atom, or a sulfur atom; n XL represents an integer from 0 to 5. XL When multiple are present, they may be the same or different. XLWhen there are a plurality of groups, they may be the same or different. *1 represents the bonding position. These bridging groups may have a substituent, and when there are a plurality of such substituents, they may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.]

[0065] The "substituent" refers to a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, or a cycloalkynyl group. The substituent may be a bridging group.

[0066] In this specification, "narrow emission spectrum width" means that the half width of the emission spectrum (expressed as FWHM: Full Width at Half Maximum) is narrow. The half width of the emission spectrum can be obtained by calculating the difference between the longest wavelength at which the emission intensity is 0.5 and the shortest wavelength at which the emission intensity is 0.5 when the emission spectrum is normalized so that the emission intensity is 1.

[0067] The emission spectrum can be obtained by preparing a film by the same method as the film preparation method described below, and measuring the PL spectrum of the film at room temperature.

[0068] <Metal complex represented by formula (1)> The metal complex according to this embodiment is represented by the formula (1). The maximum peak wavelength of the emission spectrum of the metal complex represented by formula (1) may be 380 nm or more and 750 nm or less, 400 nm or more and 640 nm or less, 450 nm or more and 620 nm or less, 495 nm or more and 570 nm or less, or 500 nm or more and 550 nm or less. The half width of the emission spectrum of the metal complex represented by formula (1) may be 100 nm, 80 nm or less, 60 nm or less, or 40 nm or less, and is preferably 35 nm or less, more preferably 30 nm or less, since the light-emitting element of this embodiment has excellent light-emitting properties.

[0069] The metal complex represented by formula (1) is a metal complex having M (a rhodium atom, a palladium atom, an iridium atom, or a platinum atom) and a subscript n 1 The ligands whose number is specified by the subscript n 2 and ligands whose number is regulated by

[0070] M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, since the emission spectrum width of the metal complex of this embodiment becomes narrower.

[0071] n 1 When M is a rhodium atom or an iridium atom, the emission spectrum width of the metal complex of the present embodiment becomes narrow, so n is preferably 2 or 3, and more preferably 3. 1 is preferably 2 when M is a platinum atom or a palladium atom, since the emission spectrum width of the metal complex of this embodiment becomes narrow.

[0072] Ring R C1 Examples of the aromatic heterocycle in the above formula include the aromatic heterocycles exemplified in the section "P-valent heterocyclic group", and these rings may have a substituent. Ring R C1 The substituent that may be substituted is preferably a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and even more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent. Ring R C1The aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are preferably groups represented by the below-described formula (DA), formula (DB) or formula (DC), and more preferably groups represented by formula (DA). Ring R C1 The substituent that the optionally substituted group may further have is preferably a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and even more preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent, but preferably do not have a further substituent. Ring R C1 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be further possessed by the substituent that may be possessed by the ring R C1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group.

[0073] Ring R C2 Examples of the monocyclic aromatic hydrocarbon ring in the above embodiment include monocyclic aromatic hydrocarbon rings exemplified in the section "Aromatic Hydrocarbon Group". Preferably, the monocyclic aromatic hydrocarbon ring is a benzene ring which may have a substituent, since this narrows the emission spectrum width of the metal complex of this embodiment. Ring R C2 Examples of the monocyclic aromatic heterocycle in the above embodiment include monocyclic aromatic heterocycles exemplified in the section "P-valent heterocyclic group". Since the emission spectrum width of the metal complex of the present embodiment is narrowed, a pyridine ring or a diazabenzene ring is preferable, and these rings may have a substituent. Ring R C2In the above, examples and preferred ranges of the monocyclic aromatic hydrocarbon ring and the monocyclic aromatic heterocycle in the fused ring in which two or more rings selected from the group consisting of the monocyclic aromatic hydrocarbon ring and the monocyclic aromatic heterocycle are fused are respectively represented by the ring R C2 The examples and preferred ranges of the monocyclic aromatic hydrocarbon ring and the monocyclic aromatic heterocycle are the same as those in the above. Ring R C2 In the above, the number of rings in the fused ring formed by condensing two or more rings selected from the group consisting of monocyclic aromatic hydrocarbon rings and monocyclic aromatic heterocycles is usually 2 to 10, preferably 2 to 5, more preferably 2 or 3, and further preferably 2. C2 In the above, the fused ring formed by condensing two or more rings selected from the group consisting of monocyclic aromatic hydrocarbon rings and monocyclic aromatic heterocycles is preferably an aromatic hydrocarbon ring formed by condensing two or more monocyclic aromatic hydrocarbon rings, and this ring may have a substituent. C2 In the above, the fused ring formed by condensing two or more rings selected from the group consisting of monocyclic aromatic hydrocarbon rings and monocyclic aromatic heterocycles is preferably a naphthalene ring, an anthracene ring, a phenanthrene ring, an azanaphthalene ring, a diazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, an azaphenanthrene ring, or a diazaphenanthrene ring, since this narrows the emission spectral width of the metal complex of this embodiment, and is more preferably a naphthalene ring, and these rings may have a substituent.

[0074] Ring R C2 The substituent that may be substituted is preferably a halogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and even more preferably an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may further have a substituent. Ring R C2Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by ring R C1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group. Ring R C2 Examples of the substituents which may be further substituted by the substituents which may be substituted by the ring R C1 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0075] Ring R C3 Examples of the aromatic hydrocarbon ring in include the aromatic hydrocarbon rings exemplified in the section "Aromatic Hydrocarbon Group" above. Since the emission spectrum width of the metal complex of this embodiment is narrowed, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, or a fluorene ring is preferable, a benzene ring or a naphthalene ring is more preferable, and a benzene ring is even more preferable. These rings may have a substituent. Ring R C3 Examples of the aromatic heterocycle represented by the formula (I) include the aromatic heterocycles exemplified in the section "P-valent heterocyclic group" above. Since the emission spectrum width of the metal complex of this embodiment is narrow, the aromatic heterocycle is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring, more preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, or a diazanaphthalene ring, and even more preferably a pyridine ring or a diazabenzene ring, and these rings may have a substituent. Ring R C3 Examples of the substituents that may be possessed by the ring R C1 The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0076] R Xis preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since the emission spectral width of the metal complex of this embodiment is narrowed, and is more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and is further preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and these groups may have a substituent. R X Examples of the substituents that may be possessed by the ring R C1 The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0077] "Two R x "together to form a divalent group" means that R x Two of these R x means that two carbon atoms directly bonded to are bonded via the divalent group. Examples of the divalent group include an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, an oxygen atom, a sulfur atom, and a group represented by -N(Ry)-, and preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, and more preferably an alkylene group or an arylene group, and these groups may have a substituent. The divalent group includes a group in which a plurality of these groups are bonded. Examples of the substituent that the divalent group may have and the preferred range thereof are as follows: Ring R C1 The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group. The number of carbon atoms of the "alkylene group", not including the number of carbon atoms of the substituent, is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, and further preferably 1 to 5. The alkylene group may have a substituent. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, and an octylene group.

[0078] The number of carbon atoms of the "cycloalkylene group", not including the number of carbon atoms of the substituent, is usually 3 to 20, and preferably 4 to 10. The cycloalkylene group may have a substituent. Examples of the cycloalkylene group include a cyclohexylene group. The alkylene group in the divalent group is preferably a methylene group, an ethylene group or a propylene group, and these groups may have a substituent. The arylene group in the divalent group is preferably a phenylene group, a naphthalenediyl group, or a fluorenediyl group, more preferably a phenylene group, and even more preferably a group represented by formula (A-3), and these groups may have a substituent. The arylene group in the divalent group is preferably a phenylene group, a naphthalenediyl group, or a fluorenediyl group, more preferably a phenylene group, and even more preferably a group represented by formula (A-3), and these groups may have a substituent. The divalent heterocyclic group in the divalent group is preferably a divalent group obtained by removing two hydrogen atoms from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, or dibenzothiophene, among the hydrogen atoms directly bonded to the carbon atoms or hetero atoms constituting the ring, and more preferably a divalent group obtained by removing two hydrogen atoms from pyridine, diazabenzene, or triazine, among the hydrogen atoms directly bonded to the carbon atoms or hetero atoms constituting the ring, and these groups may have a substituent. Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. Ry is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent. Examples of the substituent that Ry may have and the preferred range thereof are as follows: C1 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0079] [Anionic bidentate ligand] A 1 -G 1 -A 2 Examples of the anionic bidentate ligand represented by the formula include the ligand represented by the formula: 1 -G 1 -A 2 The anionic bidentate ligand represented by the subscript n 1 The number of ligands is defined as different from that of the ligands.

[0080] [ka]

[0081] [ka] [In the formula, * denotes the site that binds to M; R L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups may have a substituent; L1 may be the same or different; R L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups may have a substituent.

[0082] Ring R C2 is preferably a monocyclic aromatic hydrocarbon ring or a monocyclic aromatic heterocycle, more preferably a benzene ring, a pyridine ring or a diazabenzene ring, and even more preferably a benzene ring, since the emission spectrum width of the metal complex of this embodiment is narrowed. These rings may have a substituent.

[0083] Ring R C3 is preferably a benzene ring, a pyridine ring or a diazabenzene ring, and more preferably a benzene ring, since the emission spectrum width of the metal complex of this embodiment is narrowed. These rings may have a substituent.

[0084] Ring R C1 is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, or a diazanaphthalene ring, more preferably a pyridine ring or a diazabenzene ring, and even more preferably a pyridine ring, since the emission spectral width of the metal complex of this embodiment is narrow. These rings may have a substituent.

[0085] Since the emission spectrum width of the metal complex of this embodiment is narrow, the ring R C2 At least one of the above preferably has a substituent, more preferably has a group represented by formula (DA), formula (DB) or formula (DC) as a substituent, and further preferably has a group represented by formula (DA) as a substituent. "Ring R C2 "at least one of the rings R has a substituent" means C2 If there are multiple (n 1 is 2 or 3), multiple rings R C2 At least one of the rings R may have a substituent. However, since the emission spectrum width of the metal complex of this embodiment becomes narrow, it is preferable that a plurality of rings R C2 It is preferable that at least two of the rings R have a substituent. C2 It is more preferable that all of the groups have a substituent.

[0086] [Group represented by formula (DA), formula (DB) or formula (DC)] m DA1 ~m DA7 is usually an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, and even more preferably 0 or 1. DA2 ~m DA7 are preferably the same integer, and m DA1 ~m DA7 are more preferably the same integer.

[0087] G DAis preferably a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group, more preferably a group in which three hydrogen atoms directly bonded to carbon atoms or nitrogen atoms constituting the ring have been removed from a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, or a carbazole ring, even more preferably a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from a benzene ring, a pyridine ring, a pyrimidine ring, or a triazine ring, and particularly preferably a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from a benzene ring, and these groups may have a substituent. G DA The substituent that may be present is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and even more preferably an alkyl group or a cycloalkyl group. These groups may have a substituent, but preferably do not further have a substituent.

[0088] G DA is preferably a group represented by formula (GDA-11) to formula (GDA-15), more preferably a group represented by formula (GDA-11) to formula (GDA-14), and even more preferably a group represented by formula (GDA-11).

[0089] [ka] [In the formula, * denotes Ar in formula (DA). DA1 , Ar in formula (DB) DA1 , Ar in formula (DB) DA2 Or, Ar in formula (DB) DA3 Represents a bond with. ** indicates Ar in formula (DA). DA2 , Ar in formula (DB) DA2 , Ar in formula (DB) DA4 Or, Ar in formula (DB) DA6 Represents a bond with. *** represents Ar in formula (DA).DA3 , Ar in formula (DB) DA3 , Ar in formula (DB) DA5 Or, Ar in formula (DB) DA7 Represents a bond with. R DA R represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. DA When multiple are present, they may be the same or different.

[0090] R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group. These groups may have a substituent, but preferably do not have a further substituent. R DA Examples of the substituents that may be substituted by G DA The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0091] Ar DA1 ~Ar DA7 is preferably a phenylene group, a fluorenediyl group, or a carbazolediyl group, more preferably a group represented by formulae (ArDA-1) to (ArDA-6), even more preferably a group represented by formulae (ArDA-1) to (ArDA-3), and particularly preferably a group represented by formula (ArDA-1), and these groups may have a substituent.

[0092] Ar DA1 ~Ar DA7 Examples of the substituents that may be substituted by G DA The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0093] [ka] [In the formula, R DAhas the same meaning as above. R DB R represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. DB When multiple are present, they may be the same or different.

[0094] R DB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent.

[0095] R DB Examples of the substituents that may be substituted by G DA The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0096] T DA Examples of the substituents that may be substituted by G DA The examples and preferred ranges of the substituents which may be possessed by the group are the same as those of the substituents which may be possessed by the group.

[0097] T DA is preferably a group represented by formula (TDA-1) to formula (TDA-3), and more preferably a group represented by formula (TDA-1).

[0098] [ka] [In the formula, R DA and R DB has the same meaning as above.]

[0099] The group represented by formula (DA) is preferably a group represented by formulae (D-A1) to (D-A5), and more preferably a group represented by formula (D-A1).

[0100] [ka] [In the formula, R p1 , R p2 , R p3 and R p4 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 , R p2 and R p4 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. A plurality of np1 may be the same or different.]

[0101] The group represented by formula (DB) is preferably a group represented by formulae (D-B1) to (D-B3), and more preferably a group represented by formula (D-B1).

[0102] [ka] [In the formula, R p1 , R p2 and R p3 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 and R p2 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. When there are a plurality of np1 and a plurality of np2, they may be the same or different.

[0103] The group represented by formula (DC) is preferably a group represented by formulae (D-C1) to (D-C4).

[0104] [ka] [In the formula, R p4 , R p5 and R p6R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p4 , R p5 and R p6 When there are multiple, they may be the same or different. np4 represents an integer from 0 to 4, np5 represents an integer from 0 to 5, and np6 represents an integer from 0 to 5.

[0105] np1 is preferably an integer of 0 to 2, more preferably 0 or 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0. np4 is preferably an integer of 0 to 2, more preferably 0. np5 is preferably an integer of 0 to 3, more preferably 0 or 1. np6 is preferably an integer of 0 to 2, more preferably 0 or 1.

[0106] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 The alkyl group or cycloalkyl group in is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a cyclohexyl group or a tert-octyl group.

[0107] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 The alkoxy group or cycloalkoxy group in is preferably a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group.

[0108] R p1 , R p2 , R p3 , R p4 , R p5 and R p6is preferably an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent, more preferably an alkyl group which may have a substituent, and even more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group.

[0109] The metal complex represented by formula (1) is preferably a metal complex represented by formula (1-1) since the emission spectrum width of the metal complex of this embodiment is narrower.

[0110] R 1 and R 4 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and even more preferably a hydrogen atom, and these groups may have a substituent. R 1 and R 4 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the ring R C1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group. R 1 and R 4 Examples of the substituents that may be possessed by the ring R C1 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0111] R 5 , R 6 , R 7 and R 8 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and even more preferably a hydrogen atom, and these groups may have a substituent. R 5 , R 6 , R 7and R 8 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the ring R C1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group. R 5 , R 6 , R 7 and R 8 Examples of the substituents that may be possessed by the ring R C1 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0112] R C21 , R C22 , R C23 and R C24 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent. R C21 , R C22 , R C23 and R C24 Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the ring R C1 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group. R C21 , R C22 , R C23 and R C24 Examples and preferred ranges of the substituents which may be further substituted by the ring R C1 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0113] Since the emission spectrum width of the metal complex of this embodiment is narrow, R C21 , R C22 , R C23 and R C24At least one of the above is preferably the above formula (DA), the above formula (DB) or the above formula (DC), more preferably the above formula (DA) or the above formula (DC), and even more preferably the above formula (DA).

[0114] Since the emission spectrum width of the metal complex of this embodiment is narrow, R C21 , R C22 , R C23 and R C24 Of these, R C22 or R C23 is preferably a group of the above formula (DA), the above formula (DB) or the above formula (DC), and R C22 is more preferably the above formula (DA), the above formula (DB) or the above formula (DC).

[0115] R X is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group, and further preferably a methyl group, since this facilitates the synthesis of the present embodiment.

[0116] Since the emission spectrum width of the metal complex of this embodiment is narrow, M is an iridium atom, and n 1 It is preferred that the number is 3.

[0117] Specific examples of the metal complex of this embodiment include metal complexes represented by the following formulae (Ir-101) to (Ir-122).

[0118] [ka]

[0119] [ka]

[0120] [ka]

[0121] [ka]

[0122] [ka]

[0123] [ka]

[0124] [ka]

[0125] [ka]

[0126] [ka]

[0127] [ka]

[0128] [ka]

[0129] The metal complexes of the present embodiment may be used alone or in combination of two or more kinds.

[0130] The metal complex of this embodiment may have multiple geometric isomers, and any geometric isomer may be used; however, since the half-width of the emission spectrum of the metal complex of this embodiment is superior, the facial isomer is preferably 80 mol % or more of the entire metal complex, more preferably 90 mol % or more, even more preferably 99 mol % or more, and particularly preferably 100 mol % (i.e., no other geometric isomers are included).

[0131] <Method for producing metal complex represented by formula (1)> The method for producing the metal complex of this embodiment will be described.

[0132] [Manufacturing method] The metal complex represented by formula (1) can be produced, for example, by reacting a compound serving as a ligand with a metal compound. If necessary, a functional group conversion reaction of the ligand of the metal complex may be carried out.

[0133] In the metal complex represented by formula (1), M is an iridium atom, and n 1 is 2 or 3, for example: (i) a step A1 of synthesizing a metal complex represented by the following formula (M1-2) by reacting a compound represented by the following formula (M1-1) with an iridium compound or a hydrate thereof; and (ii) A metal complex represented by the following formula (M1-2) and a compound represented by the following formula (M1-1) or 1 -G 1 -A 2 Step B1 of reacting a precursor of a ligand represented by the formula: The composition can be produced by a method comprising the steps of:

[0134] [ka]

[0135] [ka]

[0136] [In the above formula (M1-1) and formula (M1-2), ring R C1 , ring R C2 , ring R C3 , X 1 and X 2 respectively represent the ring R in the above formula (1). C1 , ring R C2 , ring R C3 , X 1 and X 2 It has the same meaning as:

[0137] In step A1, examples of the iridium compound include iridium chloride, tris(acetylacetonato)iridium(III), chloro(cyclooctadiene)iridium(I) dimer, and iridium(III) acetate. Examples of the hydrate of the iridium compound include iridium chloride trihydrate.

[0138] Step A1 and step B1 are usually carried out in a solvent. Examples of the solvent include alcohol-based solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, and 2-ethoxyethanol; ether-based solvents such as diethyl ether, tetrahydrofuran, dioxane, cyclopentyl methyl ether, and diglyme; halogen-based solvents such as methylene chloride and chloroform; nitrile-based solvents such as acetonitrile and benzonitrile; hydrocarbon-based solvents such as hexane, decalin, toluene, xylene, and mesitylene; amide-based solvents such as N,N-dimethylformamide and N,N-dimethylacetamide; and acetone, dimethylsulfoxide, and water.

[0139] In step A1 and step B1, the reaction time is usually 30 minutes to 150 hours, and the reaction temperature is usually between the melting point and the boiling point of the solvent present in the reaction system.

[0140] In step A1, the amount of the compound represented by formula (M1-1) is usually 2 to 20 moles per mole of the iridium compound or a hydrate thereof.

[0141] In step B1, a compound represented by formula (M1-1) or A 1 -G 1 -A 2 The amount of the ligand precursor represented by the formula (M1-2) is usually 1 to 100 mol per 1 mol of the metal complex represented by the formula (M1-2).

[0142] In step B1, the reaction is preferably carried out in the presence of a silver compound such as silver trifluoromethanesulfonate. When the silver compound is used, the amount thereof is usually 2 to 20 moles per mole of the metal complex represented by formula (M1-2).

[0143] The compound represented by the above formula (M1-1) can be synthesized, for example, by subjecting a compound represented by the following formula (M1-3) and a compound represented by the following formula (M1-4) to a coupling reaction such as Suzuki reaction, Kumada reaction, Stille reaction, or the like.

[0144] [ka] [In the above formula (M1-3), ring R C1 , ring R C3 , X 1 and X 2 respectively represent the ring R in the above formula (1). C1 , ring R C2 , ring R C3 , X 1 and X 2 In addition, in formula (M1-4), ring R C2 is the ring R in the above formula (1). C2 It has the same meaning as: W 1 and W 2 -B(OR W1 ) 2 embedded image embedded image represents an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom, and these groups may have a substituent. R W1represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an amino group, and these groups may have a substituent. W1 may be the same or different and may be bonded to each other to form a ring structure together with the oxygen atom to which they are bonded.

[0145] -B(OR W1 ) 2 Examples of the group represented by the formula (W-1) include groups represented by the following formulas (W-1) to (W-10).

[0146] [ka]

[0147] The compounds, catalysts and solvents used in the reactions explained in the above section "<Production method of metal complex represented by formula (1)>" may each be used alone or in combination of two or more kinds.

[0148] <Composition> The composition according to this embodiment contains a metal complex represented by formula (1).

[0149] In addition, the composition according to the present embodiment may further contain, in addition to the metal complex represented by formula (1), at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (different from the metal complex represented by formula (1)), an antioxidant, and a solvent.

[0150] The composition according to this embodiment may contain one type of metal complex represented by formula (1), or may contain two or more types of metal complexes.

[0151] [Host material] The metal complex of the present embodiment is combined with a host material having at least one function selected from hole injection, hole transport, electron injection, and electron transport, to form a composition, which allows the light-emitting device obtained by using the metal complex of the present embodiment to have a better external quantum yield. The composition of the present embodiment may contain one or more types of host materials.

[0152] In a composition containing the metal complex of this embodiment and a host material, the content of the metal complex of this embodiment is usually 0.01 to 80 parts by mass, preferably 0.1 to 60 parts by mass, more preferably 0.5 to 40 parts by mass, and even more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total of the metal complex of this embodiment and the host material.

[0153] The lowest excited triplet state (T 1 ) is a metal complex of this embodiment, since the external quantum yield of the light-emitting device obtained by using the composition of this embodiment is excellent, the lowest excited triplet state (T 1 ) or a higher energy level.

[0154] From the viewpoint of producing a light-emitting element obtained by using the composition of this embodiment by a solution coating process, it is preferable that the host material be soluble in a solvent capable of dissolving the metal complex of this embodiment.

[0155] Host materials are classified into small molecule hosts and polymeric hosts.

[0156] Small molecule host The low molecular weight host is preferably a compound represented by formula (H-1).

[0157] [ka]

[0158] Ar H1 and ArH2 is preferably a phenyl group, a fluorenyl group, a spirobifluorenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a thienyl group, a benzothienyl group, a dibenzothienyl group, a furyl group, a benzofuryl group, a dibenzofuryl group, a pyrrolyl group, an indolyl group, an azaindolyl group, a carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group, or a phenothiazinyl group, more preferably a phenyl group, a fluorenyl group, a spirobifluorenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, or an azacarbazolyl group, and further preferably a phenyl group, a fluorenyl group, a spirobifluorenyl group, a dibenzothienyl group, a dibenzofuryl group, or a carbazolyl group, and these groups may have a substituent. Ar H1 and Ar H2 The substituent that may be substituted is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and even more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent. Ar H1 and Ar H2 The substituent that the optionally substituted group may further have is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but preferably do not further have a substituent.

[0159] n H1 is preferably 1. H2 is preferably 0. n H3 is usually an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1.

[0160] L H1 is preferably an arylene group or a divalent heterocyclic group. L H1 Examples of the alkyl group include groups represented by formulae (A-1) to (A-20) and groups represented by formulae (AA-1) to (AA-34). Groups represented by formulae (A-1), (A-2), (A-8), (A-9), (AA-1) to (AA-4), (AA-10) to (AA-15) or (AA-29) to (AA-34) are preferred, groups represented by formulae (A-1), (A-2), (A-8), (A-9), (AA-2), (AA-4) or (AA-10) to (AA-15) are more preferred, and groups represented by formulae (A-1), (A-2), (AA-2), (AA-4) or (AA-14) are even more preferred.

[0161] L H1 The substituent that may be substituted is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. L H1 Examples of the substituents that may be further substituted by the substituents that may be substituted by Ar H1 and Ar H2 The examples and preferred ranges of the substituents which may be further possessed by the group are the same as those of the substituents which may be further possessed by the group.

[0162] R H21 is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. R H21 Examples and preferred ranges of the aryl group and monovalent heterocyclic group represented by the formula: H1 and Ar H2 The examples and preferred ranges of the aryl group and monovalent heterocyclic group represented by the following formula are the same as those of the aryl group and monovalent heterocyclic group represented by the following formula: R H21 Examples of the substituents that may be substituted by ArH1 and Ar H2 The examples and preferred ranges of the substituents which may be possessed by are the same as those of the substituents which may be possessed by the group.

[0163] The compound represented by formula (H-1) is preferably a compound represented by formula (H-2).

[0164] [ka] [In the formula, Ar H1 , Ar H2 , n H3 and L H1 has the same meaning as above.]

[0165] Specific examples of the low molecular weight compound used as the host material include compounds represented by the following formulas.

[0166] [ka]

[0167] [ka]

[0168] [ka]

[0169] Polymer host Examples of the polymer compound used as the host material include a polymer compound serving as a hole transport material, which will be described later, and a polymer compound serving as an electron transport material, which will be described later.

[0170] A polymer compound preferable as a host compound (hereinafter, also referred to as a "polymer host") will be described.

[0171] The polymer host is preferably a polymer compound containing a constitutional unit represented by formula (Y).

[0172] Ar Y1 The arylene group represented by the formula (A-1), (A-2), (A-6) to (A-10), (A-19) or (A-20) is more preferred, and (A-1), (A-2), (A-7), (A-9) or (A-19) is even more preferred, and these groups may have a substituent. Ar Y1 The divalent heterocyclic group represented by the formula (AA-1) to (AA-4), (AA-10) to (AA-15), (AA-18) to (AA-21), (AA-33) or (AA-34) is more preferred, and the group represented by the formula (AA-4), (AA-10), (AA-12), (AA-14) or (AA-33) is even more preferred, and these groups may have a substituent. Ar Y1 In the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, the more preferred ranges of the arylene group and the divalent heterocyclic group are respectively as defined above in Ar Y1 The more preferred and further preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula:

[0173] Examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" include groups represented by the following formulae, which may have a substituent.

[0174] [ka]

[0175] Ar Y1 The substituent that the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups may further have a substituent. Ar Y1The substituent that the group represented by the formula (I) may have further is preferably an alkyl group or a cycloalkyl group. These groups may have further substituents, but preferably do not have further substituents.

[0176] Examples of the structural unit represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-10). From the viewpoint of the luminous efficiency of the light-emitting element of this embodiment, structural units represented by formulas (Y-1) to (Y-3) are preferred. From the viewpoint of electron transport properties, structural units represented by formulas (Y-4) to (Y-7) are preferred. From the viewpoint of hole transport properties, structural units represented by formulas (Y-8) to (Y-10) are preferred.

[0177] [ka] [In the formula, R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. X Y1 is -C(R Y2 ) 2 -, -C(R Y2 )=C(R Y2 )- or C(R Y2 ) 2 -C(R Y2 ) 2 R represents a group represented by the formula: Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. Y2 may be the same or different, R Y2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0178] R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0179] X Y1 In the above, -C(R Y2 ) 2 Two R Y2 The combination of R is preferably such that both are alkyl groups or cycloalkyl groups, both are aryl groups, both are monovalent heterocyclic groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group or monovalent heterocyclic group, more preferably one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent. Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 ) 2 The group represented by - is preferably a group represented by formulae (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), and these groups may have a substituent.

[0180] [ka]

[0181] X Y1 In the above, -C(R Y2 )=C(R Y2 Two R in the group represented by Y2 The combination of the above is preferably such that both are alkyl groups or cycloalkyl groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

[0182] X Y1 In the above, -C(R Y2 ) 2 -C(R Y2 ) 2 - represents one of the four R Y2 is preferably an alkyl group or a cycloalkyl group which may have a substituent. Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 ) 2 -C(R Y2 ) 2 The group represented by - is preferably a group represented by formula (Y-B1) to formula (Y-B5), more preferably a group represented by formula (Y-B3), and these groups may have a substituent.

[0183] [ka] [In the formula, R Y2 has the same meaning as above.]

[0184] X Y1 is preferably C(R Y2 ) 2 - is a group represented by the formula:

[0185] [ka]

[0186] [ka] [In the formula, R Y1 has the same meaning as above. R Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

[0187] R Y3is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0188] [ka]

[0189] [In the formula, R Y1 has the same meaning as above. R Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

[0190] R Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0191] R Y1 ~R Y4 and R Y11 The preferred range of the substituent that may be possessed by the group represented by Ar Y1 The preferred range of the substituent that may be possessed by the group represented by the following formula is the same as that of the substituent that may be possessed by the group represented by the following formula:

[0192] Examples of the structural unit represented by formula (Y) include structural units composed of arylene groups represented by formulas (Y-101) to (Y-121), structural units composed of divalent heterocyclic groups represented by formulas (Y-201) to (Y-206), and structural units composed of divalent groups in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other represented by formulas (Y-301) to (Y-304).

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] A structural unit represented by the formula (Y), Y1 The structural unit having an arylene group is preferably 0.5 to 100 mol %, and more preferably 60 to 95 mol %, of the total amount of structural units contained in the polymer host, since the light emitting device of this embodiment has excellent luminous efficiency.

[0203] A structural unit represented by the formula (Y), Y1A structural unit in which is a divalent heterocyclic group or a divalent group in which at least one type of arylene group and at least one type of divalent heterocyclic group are directly bonded to each other has excellent charge transport properties, and therefore the amount of the structural unit is preferably 0.5 to 30 mol %, and more preferably 3 to 20 mol %, based on the total amount of the structural units contained in the polymer host.

[0204] The polymer host may contain only one type of constitutional unit represented by formula (Y), or may contain two or more types of constitutional units.

[0205] Since the polymer host has excellent hole transport properties, it is preferable that the polymer host further contains a constitutional unit represented by formula (X).

[0206] [ka]

[0207] [In the formula, a X1 and a X2 each independently represents an integer of 0 or greater. Ar X1 and Ar X3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Ar X2 and Ar X4 each independently represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other, and these groups may have a substituent. X2 and Ar X4 When multiple are present, they may be the same or different. R X1 , R X2 and R X3 R each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. X2 and R X3 When multiple are present, they may be the same or different.

[0208] a X1 is usually an integer of 0 to 5, preferably an integer of 0 to 2, and more preferably 0 or 1. X2 is usually an integer of 0 to 5, preferably an integer of 0 to 2, and more preferably 0.

[0209] R X1 , R X2 and R X3 The preferred range, more preferred range, of R Y4 The preferred and more preferred ranges are the same as those of the above. Ar X1 , Ar X2 , Ar X3 and Ar X4 The preferred and more preferred ranges of the arylene group and the divalent heterocyclic group represented by the following formula are respectively: Y1 The preferred and more preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula: Ar X2 and Ar X4 Examples and preferred ranges of the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded are as follows: Y1 and at least one divalent heterocyclic group are directly bonded to each other. Ar X1 , Ar X2 , Ar X3 and Ar X4 is preferably an arylene group which may have a substituent. Ar X1 ~Ar X4 and R X1 ~R X3 A preferred range of the substituent that may be possessed by the group represented by Ar Y1 The preferred range of the substituent that may be possessed by the group represented by the following formula is the same as that of the substituent that may be possessed by the group represented by the following formula: The content of the structural unit represented by formula (X) is preferably 0.1 to 99 mol %, more preferably 1 to 50 mol %, and even more preferably 5 to 30 mol %, based on the total amount of structural units contained in the polymer compound.

[0210] The polymer host may contain only one type of constitutional unit represented by formula (X), or may contain two or more types of constitutional units.

[0211] The structural unit represented by formula (X) has excellent hole transport properties, and therefore the amount of the structural unit is preferably 0.1 to 50 mol %, more preferably 1 to 40 mol %, and even more preferably 2 to 30 mol %, based on the total amount of the structural units contained in the polymer host.

[0212] Examples of the constitutional unit represented by formula (X) include constitutional units represented by formulas (X1-1) to (X1-11).

[0213] [ka]

[0214] [ka]

[0215] [ka]

[0216] [ka]

[0217] [ka]

[0218] The polymer host may contain only one type of constitutional unit represented by formula (X), or may contain two or more types.

[0219] Examples of the polymer host include polymer compounds P-1 to P-7 in Table 1. Here, the "other" structural units refer to structural units other than the structural units represented by formula (Y) and the structural units represented by formula (X).

[0220] [Table 1]

[0221] In the table, p, q, r, s, and t indicate the molar ratio of each structural unit. p+q+r+s+t=100, and 100≧p+q+r+s≧70. Other structural units refer to structural units other than the structural units represented by formula (Y) and the structural units represented by formula (X).

[0222] The polymer host may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other embodiments. From the above viewpoint, however, it is preferable that the polymer host is a copolymer obtained by copolymerizing a plurality of raw material monomers.

[0223] <Method of Producing Polymer Host> The polymer host can be produced by a known polymerization method described in, for example, Chem. Rev., Vol. 109, pp. 897-1091 (2009). Examples of the polymerization method include a coupling reaction using a transition metal catalyst, such as the Suzuki reaction, the Yamamoto reaction, the Buchwald reaction, the Stille reaction, the Negishi reaction, and the Kumada reaction.

[0224] In the above polymerization method, examples of the method for feeding the monomers include a method in which the entire amount of the monomers is fed into the reaction system all at once, a method in which a part of the monomers is fed and reacted, and then the remaining monomers are fed all at once, continuously or in portions, and a method in which the monomers are fed continuously or in portions.

[0225] The transition metal catalyst is not particularly limited, but examples thereof include palladium catalysts and nickel catalysts.

[0226] The post-treatment of the polymerization reaction is carried out by a known method, for example, a method of removing water-soluble impurities by liquid separation, a method of adding the reaction liquid after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying the precipitate, either alone or in combination. When the purity of the polymer host is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, etc.

[0227] [Hole transport material] The hole transport material is classified into a low molecular weight compound and a high molecular weight compound. The hole transport material may have a crosslinking group.

[0228] Examples of low molecular weight compounds include aromatic amine compounds such as triphenylamine and its derivatives, N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (α-NPD), and N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (TPD).

[0229] Examples of the polymeric compound include polyvinylcarbazole and its derivatives; polyarylene and its derivatives having an aromatic amine structure in the side chain or main chain. The polymeric compound may be a compound to which an electron-accepting moiety is bonded. Examples of the electron-accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, etc., and fullerene is preferred.

[0230] In the composition according to this embodiment, the amount of the hole transport material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, based on 100 parts by mass of the metal complex represented by formula (1).

[0231] The hole transport material may be used alone or in combination of two or more kinds.

[0232] The hole injection material and the electron injection material are classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injection material and the electron injection material may have a crosslinking group.

[0233] Examples of low molecular weight compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.

[0234] Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylenevinylene, polyphenylenevinylene, polyquinoline, polyquinoxaline, and derivatives thereof; and conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain.

[0235] In the composition according to this embodiment, the amount of the hole injection material and the electron injection material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, per 100 parts by mass of the metal complex represented by formula (1).

[0236] The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.

[0237] [Electron transport material] The electron transport material is classified into a low molecular weight compound and a high molecular weight compound. The electron transport material may have a crosslinking group.

[0238] Examples of low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazolyl, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, as well as derivatives thereof.

[0239] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

[0240] In the composition according to this embodiment, the amount of the electron transport material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, based on 100 parts by mass of the metal complex represented by formula (1).

[0241] The electron transporting materials may be used alone or in combination of two or more kinds.

[0242] [Luminescent materials] The luminescent material (different from the metal complex represented by formula (1)) is classified into a low molecular weight compound and a high molecular weight compound. The luminescent material may have a crosslinking group.

[0243] Examples of low molecular weight compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triplet luminescent complexes having iridium, platinum, or europium as a central metal.

[0244] Examples of the polymer compound include polymer compounds containing a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a group represented by formula (X), a carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, and the like.

[0245] The light-emitting material preferably comprises a triplet light-emitting complex and / or polymer compound.

[0246] In the composition according to this embodiment, the content of the light emitting material is usually 0.1 to 400 parts by mass with respect to 100 parts by mass of the metal complex represented by formula (1).

[0247] [solvent] The composition according to the present embodiment may be a liquid composition (also called ink) containing the metal complex represented by formula (1) and a solvent. Such an ink is suitable for producing a light-emitting device using a printing method such as an ink-jet method or a nozzle printing method.

[0248] The viscosity of the ink can be adjusted depending on the type of printing method; however, when applied to a printing method in which the solution passes through a discharge device, such as inkjet printing, the viscosity is preferably 1 to 20 mPa s at 25°C, since this prevents clogging and deflection during discharge.

[0249] The solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of the solvent include chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as THF, dioxane, anisole, and 4-methylanisole; aromatic hydrocarbon-based solvents such as toluene, xylene, mesitylene, ethylbenzene, hexylbenzene, and cyclohexylbenzene; and aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, pentane, hexane, heptane, octane, nonane, decane, dodecane, and bicyclohexyl. Examples of the solvent include ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate; polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; and amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide. The solvents may be used alone or in combination of two or more.

[0250] In the ink, the blending amount of the solvent is usually 1,000 to 100,000 parts by mass, and preferably 2,000 to 20,000 parts by mass, per 100 parts by mass of the metal complex represented by formula (1).

[0251] [Antioxidants] The antioxidant is preferably a compound that is soluble in the same solvent as the metal complex represented by formula (1) and does not inhibit light emission and charge transport. Examples of the antioxidant include phenol-based antioxidants and phosphorus-based antioxidants.

[0252] In the composition according to this embodiment, the amount of the antioxidant is usually 0.001 to 10 parts by mass with respect to 100 parts by mass of the metal complex represented by formula (1).

[0253] The antioxidants may be used alone or in combination of two or more kinds.

[0254] <Membrane> The film contains the metal complex of this embodiment. The film is suitable as a light-emitting layer in a light-emitting device.

[0255] The film can be prepared using an ink by, for example, spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, inkjet printing, capillary coating, or nozzle coating.

[0256] The thickness of the film is usually from 1 nm to 10 μm.

[0257] <Light emitting element> The light-emitting device according to this embodiment contains a metal complex represented by formula (1).

[0258] The light emitting device according to this embodiment may have, for example, electrodes consisting of an anode and a cathode, and a layer containing a metal complex represented by formula (1) provided between the electrodes.

[0259] [Layer composition] The layer containing the metal complex represented by formula (1) is usually one or more of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer, and is preferably a light-emitting layer. Each of these layers contains a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. Each of these layers can be formed by dissolving the material of each layer in the above-mentioned solvent to prepare an ink, and using the same method as the above-mentioned film preparation.

[0260] The light-emitting element according to the present embodiment may have a light-emitting layer between the anode and the cathode. From the viewpoint of hole injection and hole transport properties, the light-emitting element according to the present embodiment preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light-emitting layer, and from the viewpoint of electron injection and electron transport properties, preferably has at least one layer of an electron injection layer and an electron transport layer between the cathode and the light-emitting layer.

[0261] Materials for the hole transport layer, electron transport layer, light-emitting layer, hole injection layer and electron injection layer include the metal complex represented by formula (1) as well as the hole transport material, electron transport material, light-emitting material, hole injection material and electron injection material described above, respectively.

[0262] The material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer may have a crosslinking group, and after each layer is formed using a material having a crosslinking group, the material may be crosslinked to make the layer insoluble, thereby preventing the material of each layer from dissolving in a solvent used in forming the adjacent layer.

[0263] In the light-emitting element according to this embodiment, examples of the method for forming each layer, such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, include, when a low molecular weight compound is used, a vacuum deposition method from a powder, and a method of film formation from a solution or molten state. When a high molecular weight compound is used, examples of the method include a method of film formation from a solution or molten state.

[0264] The order, number and thickness of the layers to be laminated are adjusted taking into consideration the external quantum efficiency and luminance life.

[0265] [Substrate / electrode] The substrate in the light-emitting device is preferably a substrate on which an electrode can be formed and which is not chemically changed when an organic layer is formed. The substrate may be, for example, a substrate made of a material such as glass, plastic, silicon, etc. The substrate is preferably transparent or semi-transparent, and in the case of an opaque substrate, the electrode furthest from the substrate is preferably transparent or semi-transparent.

[0266] Examples of materials for the anode include conductive metal oxides and translucent metals, and preferred are indium oxide, zinc oxide, tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; a composite of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.

[0267] Examples of the cathode material include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of these metals; alloys of one or more of these metals with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys.

[0268] The anode and the cathode may each have a laminated structure of two or more layers.

[0269] [Application] In order to obtain planar light emission using a light-emitting element, planar anodes and cathodes may be arranged so as to overlap. In order to obtain patterned light emission, there are a method of placing a mask with patterned windows on the surface of a planar light-emitting element, a method of forming a layer to be a non-light-emitting portion extremely thick to make it substantially non-light-emitting, and a method of forming the anode or cathode, or both electrodes, in a pattern. By forming a pattern by any of these methods and arranging some electrodes so that they can be turned on / off independently, a segment-type display device capable of displaying numbers, letters, etc. is obtained. In order to obtain a dot-matrix display device, both anodes and cathodes may be formed in stripes and arranged so as to be perpendicular to each other. By a method of painting a plurality of types of polymer compounds with different light-emitting colors, or a method of using a color filter or a fluorescent conversion filter, partial color display and multi-color display are possible. The dot-matrix display device can be passively driven, or can be actively driven in combination with a TFT or the like. These display devices can be used for displays of computers, televisions, mobile terminals, etc. Planar light-emitting elements can be suitably used as planar light sources for backlighting liquid crystal display devices, or as planar light sources for illumination. If a flexible substrate is used, it can also be used as a curved light source and display device. EXAMPLES

[0270] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0271] LC-MS was measured by the following method. The measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (Agilent, product name: 1290 Infinity LC and 6230 TOF LC / MS). The mobile phase of LC-MS was a mixture of acetonitrile and tetrahydrofuran, with the ratio being varied, and the flow rate was 1.0 mL / min. The column used was SUMIPAX ODS Z-CLUE (Sumika Analysis Center, inner diameter: 4.6 mm, length: 250 mm, particle size: 3 μm).

[0272] NMR was measured by the following method. 5 to 10 mg of a measurement sample was dissolved in approximately 0.5 mL of deuterated chloroform (CDCl3), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N,N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol or deuterated methylene chloride, and measured using an NMR device (JEOL RESONANCE, product name: JNM-ECZ400S / L1, or Bruker, product name: AVANCE600).

[0273] As an index of the purity of the compound, the value of the area percentage of high performance liquid chromatography (HPLC) was used. This value is the value at UV=254 nm in HPLC (manufactured by Shimadzu Corporation, product name: LC-20A) unless otherwise specified. In this case, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2 mass%, and 1 to 10 μL was injected into the HPLC depending on the concentration. The mobile phase of the HPLC was used with a ratio of acetonitrile / tetrahydrofuran changed from 100 / 0 to 0 / 100 (volume ratio), and was run at a flow rate of 1.0 mL / min. The column used was SUMIPAX ODS Z-CLUE (manufactured by Sumika Chemical Analysis Center, inner diameter: 4.6 mm, length: 250 mm, particle size: 3 μm) or an ODS column with equivalent performance. The detector used was a photodiode array detector (manufactured by Shimadzu Corporation, product name: SPD-M20A).

[0274] The emission spectrum of the thin film at room temperature was measured using a spectrophotometer (FP-6500, manufactured by JASCO Corporation) at room temperature. The half-width (hereinafter, also referred to as "FWHM") of the emission spectrum was measured using a spectrophotometer (FP-6500, manufactured by JASCO Corporation) at room temperature. The compound was dissolved in xylene at a concentration of about 8 × 10 -4 A xylene solution containing 100% by mass of ZnO was used as a sample. The sample was formed into a thin film of 80 nm on a quartz substrate by spin coating. Ultraviolet (UV) light with a wavelength of 325 nm was used as the excitation light.

[0275] <Example 1> Synthesis of metal complex M1 Metal complex M1 was synthesized by the following method.

[0276] [ka]

[0277] [ka]

[0278] [ka]

[0279] [ka]

[0280] (Synthesis of compound L1F) Compound L1F was synthesized according to the method described in JP 2017-052709 A.

[0281] (Stage 1: Synthesis of compound L1B) After the inside of the reaction vessel was filled with nitrogen, compound L1A (14.3 g) and tetrahydrofuran (191 g) were added and cooled to 0°C. Boron trifluoride (11.5 mL) was slowly added thereto and stirred at 0°C for 1 hour. After cooling to -30°C, a benzyl magnesium chloride-lithium chloride tetrahydrofuran solution (0.4 M, 250 mL) prepared in advance was dropped over 1 hour. Then, the mixture was stirred at -30°C for 1 hour. Chloranil (22.5 g) was slowly added thereto. After the obtained reaction solution was brought to room temperature, ion-exchanged water (180 g) and n-heptane (180 g) were slowly added thereto and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, magnesium sulfate was added to the obtained organic layer to dry it, and then it was filtered. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and n-hexane) and dried under reduced pressure at 50° C. to obtain compound L1B (11.8 g). When compound L1B was analyzed by high performance liquid chromatography (HPLC), the HPLC area percentage value of compound L1B was 92.3%. 1 H-NMR (400MHz, CD 2 Cl 2 )δ(ppm)=8.84(s, 1H),7.34-7.29(m, 2H),7.25(t, 1H),7.19-7.13(m, 2H),7.11(s, 1H),4.37(s, 2H),3.88(s, 3H).

[0282] (Stage 2: Synthesis of compound L1C) After the inside of the reaction vessel was filled with nitrogen, compound L1B (18.3 g) and tetrahydrofuran (191 g) were added and cooled to 0°C. Methyl magnesium chloride tetrahydrofuran solution (1 M, 200 mL) was added dropwise over 2 hours. Then, the mixture was stirred at 0°C for 2 hours. 1 M hydrochloric acid (200 mL) was slowly added thereto. After the obtained reaction solution was brought to room temperature, ion-exchanged water (180 g) and heptane (180 g) were slowly added and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of ethyl acetate and n-hexane), washed with a mixed solvent of ethyl acetate and n-hexane, and dried under reduced pressure at 50°C to obtain compound L1C (9.1 g). When compound L1C was analyzed by HPLC, the HPLC area percentage value of compound L1C was 97.5%. 1 H-NMR (400MHz, CD 2 Cl 2 )δ(ppm)=8.40(s, 1H),7.32(t, 2H),7.26(t, 1H),7.13(d, 2H),6.96(s, 1H),4.41(s, 2H),1.68(s, 6H).

[0283] (Stage 3: Synthesis of compound L1D) After the inside of the reaction vessel was filled with nitrogen, sulfuric acid (60 mL) was added and cooled to 0°C. Compound L1C (6.0 g) was added thereto. After stirring at 0°C for 1 hour, the obtained reaction solution was added to ice water. NaOH aqueous solution and heptane (60 g) were slowly added to the obtained aqueous solution, and the water layer was removed. The obtained organic layer was washed with ion-exchanged water and then filtered. The obtained organic layer was washed with ion-exchanged water and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of ethyl acetate and n-hexane) and dried under reduced pressure at 50°C to obtain compound L1D (3.5 g) as a white solid. When compound L1D was analyzed by HPLC, the HPLC area percentage value of compound L1D was 99.0%. 1H-NMR (400MHz, CD 2 Cl 2 )δ(ppm)=8.51(s, 1H),7.55(d, 2H),7.33-7.20(m, 4H),4.05(s, 2H),1.63(s, 6H).

[0284] (Stage 4: Synthesis of compound L1E) After the inside of the reaction vessel was filled with nitrogen, 60% sodium hydride (1.7 g), methyl iodide (10.2 g), tetrahydrofuran (21 mL), and dimethylformamide (11 mL) were added and cooled to 0°C. A mixed solution of compound L1D (3.5 g) and tetrahydrofuran (14 mL) was added dropwise thereto over 1 hour. The temperature was raised to room temperature and stirred for 1 hour, and then the temperature was raised to 55°C and stirred for 4 hours. The obtained reaction solution was cooled to room temperature, and then ion-exchanged water (14 mL) and n-heptane (28 mL) were added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of ethyl acetate and n-hexane), and then repeatedly crystallized from a mixed solvent of toluene and n-heptane, and dried under reduced pressure at 50°C to obtain compound L1E (2.2 g). Compound L1E was analyzed by HPLC, and the HPLC area percentage value of compound L1E was 99.2%. 1 H-NMR (400MHz, CD 2 Cl 2 )δ(ppm)=8.56(s,1H),7.55-7.47(m,2H),7.43(s,1H),7.31-7.25(m,2H),1.70(s,6H),1.64(s,6H).

[0285] (Stage 5: Synthesis of compound L1G) After the inside of the reaction vessel was filled with nitrogen, compound L1F (40.0 g), 1-bromo-4-iodobenzene (21.4 g), tetrakis(triphenylphosphine)palladium(0) (1.59 g), 20% by mass tetraethylammonium hydroxide aqueous solution (152.2 g), and toluene (400 mL) were added and stirred at 80° C. for 4 hours. The obtained reaction solution was cooled to room temperature, and then ion-exchanged water (200 mL) was added and the water layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and n-hexane), crystallized with toluene and methanol, and dried under reduced pressure at 50° C. to obtain compound L1G (36.7 g). When compound L1G was analyzed by HPLC, the HPLC area percentage value of compound L1G was 99.0%.

[0286] (Stage 6: Synthesis of compound L1H) After the inside of the reaction vessel was filled with nitrogen, compound L1G (36.0 g), bis(pinacolato)diboron (16.5 g), dimethoxyethane (360 mL), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride·dichloromethane adduct (1.2 g), and potassium acetate (17.4 g) were added and stirred at 80°C for 5 hours. Celite (6.9 g) was added to the reaction solution, which was then filtered through a filter lined with silica gel. The filtrate was concentrated under reduced pressure to obtain a crude product. Toluene and activated carbon were added to the crude product, which was stirred at room temperature for 30 minutes, filtered through a filter lined with Celite, and the filtrate was concentrated under reduced pressure. Compound L1H (35.6 g) was obtained as a white solid by crystallizing with toluene and methanol and drying at 50°C under reduced pressure. When compound L1H was analyzed by HPLC, the HPLC area percentage value of compound L1H was 98.9%.

[0287] (Stage 7: Synthesis of compound L1) After the inside of the reaction vessel was filled with nitrogen, compound L1E (0.8 g), compound L1H (2.1 g), tris(dibenzylideneacetone)dipalladium(0) (40.0 mg), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (60.9 mg), 10% by mass tetrabutylammonium hydroxide aqueous solution (22.9 g), and toluene (16 mL) were added and stirred at 90 ° C for 5 hours. After the obtained reaction liquid was cooled to room temperature, ion-exchanged water (130 mL) was added and the water layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was crystallized with toluene and acetonitrile, and dried under reduced pressure at 50 ° C to obtain compound L1 (2.0 g). When compound L1 was analyzed by HPLC, the HPLC area percentage value of compound L1 was 99.5% or more. 1 H-NMR (400MHz, CD 2 Cl 2 )δ(ppm)=8.90(s, 1H), 8.18(d, 2H), 7.93-7.84(m, 6H), 7.69(d, 4H), 7.60-7.48(m, 6H), 7.33-7.27(m, 2H), 1.83(s, 4H), 1.77(s, 6H), 1.75(s, 6H), 1.43(s, 12H), 0.78(s, 18H).

[0288] (Stage 8: Synthesis of metal complex M1a) After the inside of the light-shielded reaction vessel was filled with argon gas, iridium(III) chloride hydrate (250 mg), compound L1 (1.2 g) and 2-ethoxyethanol (12.5 mL) were added and stirred at 130° C. for 18 hours. The resulting reaction product was cooled to room temperature, then added to methanol (16 mL) and stirred at room temperature for 1 hour. Then, filtration was performed, and the resulting residue was dried under reduced pressure to obtain a yellow solid (0.80 g) containing the metal complex M1a.

[0289] (Stage 9: Synthesis of metal complex M1) After the inside of a light-shielded reaction vessel was filled with an argon gas atmosphere, a red solid containing metal complex M1a (0.77 g), compound L1 (0.35 g), silver(I) trifluoromethanesulfonate (0.15 g), 2,6-lutidine (69 μL) and diethylene glycol dimethyl ether (15 mL) were added and stirred at 150° C. for 4 hours. The resulting reaction product was cooled to room temperature, then added to methanol (50 mL) and stirred at room temperature for 1 hour, then filtered, toluene (50 mL) was added to the resulting residue, filtered through a filter covered with Celite, and the resulting filtrate was concentrated under reduced pressure to obtain a solid. The solid obtained was purified by silica gel column chromatography (toluene / hexane) and crystallization (toluene / ethanol), and then dried under reduced pressure to obtain metal complex M1 (0.54 g, IrCl when iridium(III) chloride hydrate was converted to trihydrate). 3 3H 2 Metal complex M1 was obtained as a yellow solid (yield: 49%) based on the amount of O charged. When metal complex M1 was analyzed by HPLC, the HPLC area percentage value of metal complex M1 was 98.5%. LC-MS(APCI positive):m / z=2488.5[M] + 1 H-NMR (400MHz, CD 2 Cl 2 )δ(ppm)=8.08(s,3H), 7.95(s, 3H), 7.89-7.86(m, 6H), 7.84(d, 3H), 7. 79(s, 3H), 7.70(d, 3H), 7.53(d, 3H), 7.52-7.46(m, 6H), 7.43(d, 3H), 7 .36(d, 3H), 7.30-7.20(m, 6H), 7.11(d, 12H), 1.79(s, 9H), 1.73(s, 9H) , 1.61(s, 9H), 1.52(s, 24H), 1.32(s, 9H), 1.20(s, 36H), 0.61(s, 54H).

[0290] (Synthesis of polymer compound IP1) Polymer compound IP1 was synthesized by the method described in JP-A-2012-036388 using monomer PM1, monomer PM2, and monomer PM3, which were synthesized according to the method described in JP-A-2012-036388.

[0291] [ka]

[0292] The polymer compound IP1 is a copolymer composed of structural units derived from monomer PM1, structural units derived from monomer PM2, and structural units derived from monomer PM3 in a molar ratio of 50:40:10, according to the theoretical value calculated from the amounts of the charged raw materials.

[0293] (Preparation and evaluation of thin film L1) Polymer compound P1 and metal complex M1 (polymer compound P1 / metal complex M1=70% by mass / 30% by mass) were dissolved in xylene at a concentration of 2% by mass solid content. The resulting xylene solution was used to form a thin film L1 with a thickness of 80 nm on a quartz substrate by spin coating.

[0294] The maximum peak wavelength of the emission spectrum of the thin film L1 at room temperature was measured using a spectrophotometer (JASCO Corporation, FP-6500) at room temperature. By exciting the thin film with ultraviolet (UV) light of 325 nm, emission with a peak at 526 nm, the maximum intensity of the emission spectrum, was observed. Figure 1 shows the emission spectrum of the metal complex M1.

[0295] The half width of the emission spectrum was 30 nm. The results are shown in Table 1 below.

[0296] <Comparative Example 1> Synthesis of metal complex CM1 Metal complex CM1 was synthesized by the following method.

[0297] [ka]

[0298] [ka]

[0299] (Stage 1: Synthesis of compound CL1) After the inside of the reaction vessel was filled with nitrogen, compound CL1A (25.0 g), compound CL1B (52.5 g), tetrakis(triphenylphosphine)palladium(0) (1.23 g), 20% by mass tetraethylammonium hydroxide aqueous solution (315 g), and toluene (440 mL) were added and stirred at 70° C. for 4 hours. The obtained reaction liquid was cooled to room temperature, and then ion-exchanged water (125 mL) was added and the water layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (toluene), crystallized with toluene and acetonitrile, and dried under reduced pressure at 50° C. to obtain compound CL1 (41.5 g). When compound CL1 was analyzed by HPLC, the HPLC area percentage value of compound CL1 was 99.5% or more.

[0300] (Stage 8: Synthesis of metal complex CM1a) After the inside of a light-shielded reaction vessel was filled with argon gas, iridium(III) chloride hydrate (1.25 g), compound CL1 (3.92 g), ion-exchanged water (18.0 mL) and 2-ethoxyethanol (81.5 mL) were added and stirred at 105° C. for 21 hours. The resulting reaction product was cooled to room temperature, then added to methanol (16 mL) and stirred at room temperature for 1 hour. Then, filtration was performed, and the resulting residue was washed with toluene and methanol and dried under reduced pressure to obtain a yellow solid (3.48 g) containing the metal complex CM1a.

[0301] (Stage 9: Synthesis of metal complex CM1) After the inside of a light-shielded reaction vessel was filled with an argon gas atmosphere, a yellow solid containing metal complex CM1a (1.00 g), compound CL1 (2.04 g), silver(I) trifluoromethanesulfonate (0.23 g), 2,6-lutidine (0.14 g) and diethylene glycol dimethyl ether (9.5 g) were added and stirred at 160° C. for 3 hours. The resulting reaction product was cooled to room temperature, then added to methanol (50 mL) and stirred at room temperature for 1 hour, then filtered, toluene (50 mL) was added to the resulting residue, filtered through a filter covered with Celite, and the resulting filtrate was concentrated under reduced pressure to obtain a solid. The solid obtained was purified by silica gel column chromatography (toluene / hexane) and crystallization (toluene / heptane), and then dried under reduced pressure to obtain metal complex CM1 (0.93 g, IrCl when iridium(III) chloride hydrate was converted into trihydrate). 3 3H 2 Metal complex M1 was obtained as a yellow solid (yield 79%) based on the amount of O charged. When metal complex M1 was analyzed by HPLC, the HPLC area percentage value of metal complex M1 was 99.5% or more. LC-MS(ESI positive):m / z=1714.8[M+K] +

[0302] (Preparation and evaluation of thin film CL1) A thin film CL1 was prepared in the same manner as in Example 1, except that metal complex CM1 was used instead of metal complex M1.

[0303] The maximum peak wavelength of the emission spectrum of thin film CL1 at room temperature was measured using a spectrophotometer (JASCO Corporation, FP-6500) at room temperature. By exciting the thin film with ultraviolet (UV) light at a wavelength of 325 nm, emission with a peak at 535 nm, the maximum intensity of the emission spectrum, was observed. Figure 1 shows the emission spectrum of metal complex CM1.

[0304] The half width of the emission spectrum was 40 nm. The results are shown in Table 1 below.

[0305] <Comparative Example 2> Synthesis of metal complex CM2 The metal complex CM2 used was manufactured by American Dye Source.

[0306] [ka]

[0307] (Preparation and evaluation of thin film CL2) A thin film CL2 was prepared in the same manner as in Example 1, except that metal complex CM2 was used instead of metal complex M1.

[0308] The maximum peak wavelength of the emission spectrum of the thin film CL2 at room temperature was measured using a spectrophotometer (JASCO Corporation, FP-6500) at room temperature. By exciting the thin film with ultraviolet (UV) light at a wavelength of 325 nm, emission with a peak at 506 nm, the maximum intensity of the emission spectrum, was observed. Figure 1 shows the emission spectrum of the metal complex CM2.

[0309] The half width of the emission spectrum was 56 nm. The results are shown in Table 1 below.

[0310] [Table 2]

[0311] FIG. 2 is a graph in which the peak positions of the emission spectrum of metal complex M1 of Example 1 are superimposed with the peak positions of the emission spectrum of metal complex CM1 of Comparative Example 1 and the peak positions of the emission spectrum of metal complex CM2 of Comparative Example 2.

[0312] The half-width values ​​shown in Table 1 and the difference in the width of the emission spectrum compared to FIG. 2 show that the width of the emission spectrum of the metal complex of the present invention is narrower than that of the metal complex of the comparative example. [Industrial Applicability]

[0313] According to the present invention, it is possible to provide a metal complex having a narrow emission spectrum width. Furthermore, according to the present invention, it is possible to provide a composition containing the metal complex and a light-emitting device containing the metal complex.

Claims

1. A metal complex represented by formula (1): 【Chemistry 1】 [In the formula, M represents a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n １ represents 1, 2 or 3; n ２ represents 0. However, when M is a rhodium atom or an iridium atom, n １ +n ２ is 3, and when M is a platinum atom or a palladium atom, n １ +n ２ is 2. Ring R Ｃ１ represents a pyridine ring, and the pyridine ring may have an alkyl group or a cycloalkyl group as a substituent. Ｃ１ When multiple are present, they may be the same or different. Ring R Ｃ２ represents a benzene ring, a pyridine ring or a diazabenzene ring, and these rings may have a group represented by formula (DA), formula (DB) or formula (DC) as a substituent. Ｃ２ When multiple are present, they may be the same or different. Ring R Ｃ３ represents a benzene ring, a pyridine ring or a diazabenzene ring, and these rings may have an alkyl group or a cycloalkyl group as a substituent. Ｃ３ When multiple are present, they may be the same or different. X １ and X ２ Each independently represents -C(R Ｘ ) ２ - represents a group represented by the formula: R Ｘ represents a hydrogen atom, an alkyl group, or a cycloalkyl group. ｘ may be the same or different. 【Chemistry 2】 [In the formula, m ＤＡ１ , m ＤＡ２ and m ＤＡ３ each independently represents an integer of 0 or more. G ＤＡ represents a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from the benzene ring, and may have an alkyl group or a cycloalkyl group as a substituent. Ar ＤＡ１ , Ar ＤＡ２ and Ar ＤＡ３ each independently represents a phenylene group, and may have an alkyl group or a cycloalkyl group as a substituent. ＤＡ１ , Ar ＤＡ２ and Ar ＤＡ３ When multiple are present, they may be the same or different. T ＤＡ represents a phenyl group, which may have an alkyl group or a cycloalkyl group as a substituent. ＤＡ may be the same or different. 【Chemistry 3】 [In the formula, m ＤＡ１ , m ＤＡ２ , m ＤＡ３ , m ＤＡ４ , m ＤＡ５ , m ＤＡ６ and m ＤＡ７ each independently represents an integer of 0 or more. G ＤＡ represents a group in which three hydrogen atoms directly bonded to carbon atoms constituting the ring have been removed from the benzene ring, and may have an alkyl group or a cycloalkyl group as a substituent. ＤＡ may be the same or different. Ar ＤＡ１ , Ar ＤＡ２ , Ar ＤＡ３ , Ar ＤＡ４ , Ar ＤＡ５ , Ar ＤＡ６ and Ar ＤＡ７ each independently represents a phenylene group, and may have an alkyl group or a cycloalkyl group as a substituent. ＤＡ１ , Ar ＤＡ２ , Ar ＤＡ３ , Ar ＤＡ４、 Ar ＤＡ５ , Ar ＤＡ６ and Ar ＤＡ７ When multiple are present, they may be the same or different. T ＤＡ represents a phenyl group, which may have an alkyl group or a cycloalkyl group as a substituent. ＤＡ may be the same or different. 【Chemistry 4】 [In the formula, m ＤＡ１ represents an integer of 0 or more; Ar ＤＡ１ represents a phenylene group, which may have an alkyl group or a cycloalkyl group as a substituent. ＤＡ１ When multiple are present, they may be the same or different; T ＤＡ represents a phenyl group, which may have an alkyl group or a cycloalkyl group as a substituent.

2. The metal complex according to claim 1, which is a metal complex represented by formula (1-1). 【Chemistry 5】 [In the formula, M, n １ , n ２ , R Ｘ and A １ -G １ -A ２ has the same meaning as above; R １ , R ４ , R ５ , R ６ , R ７ and R ８ each independently represents a hydrogen atom, an alkyl group, or a cycloalkyl group; R Ｃ２１ , R Ｃ２２ , R Ｃ２３ and R Ｃ２４ R each independently represents a hydrogen atom or a group represented by formula (DA), formula (DB) or formula (DC). １ , R ４ , R ５ , R ６ , R ７ , R ８ , R Ｃ２１ , R Ｃ２２ , R Ｃ２３ and R Ｃ２４ When there are multiple, they may be the same or different.

3. R Ｃ２１ , R Ｃ２２ , R Ｃ２３ and R Ｃ２４ The metal complex according to claim 2, wherein at least one of the above is a group represented by formula (DA).

4. The metal complex according to any one of claims 1 to 3, wherein M is an iridium atom and n1 is 3.

5. A metal complex according to any one of claims 1 to 4, At least one compound selected from the group consisting of compounds represented by formula (H-1) and polymer compounds containing a structural unit represented by formula (Y), A composition comprising: 【Chemistry 6】 [In the formula, Ar Ｈ１ and Ar Ｈ２ each independently represents an aryl group or a monovalent heterocyclic group, and these groups may have an alkyl group or a cycloalkyl group as a substituent. n Ｈ１ and n Ｈ２ Each independently represents 0 or 1. Ｈ１ When there are a plurality of n, they may be the same or different. Ｈ２ may be the same or different. n Ｈ３ represents an integer of 0 or greater. L Ｈ１ represents an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, and these groups may have an alkyl group or a cycloalkyl group as a substituent. Ｈ１ When multiple are present, they may be the same or different. L Ｈ２ is -N(-R Ｈ２１ )- represents a group represented by L Ｈ２ When there are a plurality of R, they may be the same or different. Ｈ２１ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have an alkyl group or a cycloalkyl group as a substituent. 【Chemistry 7】 [In the formula, Ar Ｙ１ represents an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded to each other, and these groups may have an alkyl group or a cycloalkyl group as a substituent.

6. A metal complex according to any one of claims 1 to 4, at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent; A composition comprising:

7. A film containing the metal complex according to any one of claims 1 to 4.

8. A light-emitting device comprising the metal complex according to any one of claims 1 to 4.

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