Metal complex, composition containing same, and light-emitting device

Abstract

To provide a metal complex useful for production of a light-emitting element exhibiting an improved luminance life.SOLUTION: A metal complex is exemplified by a following formula.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a metal complex, a composition containing the metal complex, and a light-emitting device containing the metal complex. [Background technology]

[0002] As a light-emitting material used in the light-emitting layer of a light-emitting element, various phosphorescent compounds that emit light from a triplet excited state have been studied. As such phosphorescent compounds, many metal complexes in which the central metal is a transition metal belonging to the fifth or sixth period have been studied. For example, Patent Document 1 proposes a metal complex having a fluorenylquinoline structure as a ligand (for example, a metal complex represented by the following formula).

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

[0004] [Patent Document 1] JP 2006-151888 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, the luminance life of the light-emitting element produced using the above metal complex is not necessarily sufficient.

[0006] Therefore, an object of the present invention is to provide a metal complex useful for producing a light-emitting device exhibiting an improved luminance life. Another object of the present invention is to provide a composition containing the metal complex and a light-emitting device containing the metal complex. [Means for solving the problem]

[0007] The present invention provides the following [1] to

[12] .

[0008] [1] A metal complex represented by the following formula (0): [ka] [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; 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; n 1 If is 2 or 3, the subscript n 1 The ligands whose numbers are defined by may be the same or different; n 2 If is 2, then the subscript n 2 Each of the ligands, the number of which is defined by, may be the same or different; Subscript n 1 In each or one of the ligands, the number of which is defined by C1 and ring R C2 each independently represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which they are bonded; Subscript n 1 In each or one of the ligands, the number of which is defined by X a and X b One of them is a single bond and the other is -C(R Xa )2-, -C(R Xa )2-C(R Xa )2-, or -C(R Xa )=C(R Xa )- is a group represented by R Xarepresents 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. When a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which each is bonded, and when a plurality of R Xa may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are attached; Subscript n 1 For each or one of the ligands, the number of which is defined by E 1 , E 2 , E 3 , E 4 , E 5 , and E 6 each independently represents a nitrogen atom or a carbon atom, and at least E 1 and E 2 , E 2 and E 3 , E 3 and E 4 , E 4 and E 5 , or E 5 and E 6 is a carbon atom; 1 When is a nitrogen atom, R 1 does not exist;E 2 When is a nitrogen atom, R 2 does not exist;E 3 When is a nitrogen atom, R 3 does not exist;E 4 When is a nitrogen atom, R 4 does not exist;E 5 When is a nitrogen atom, R 5 does not exist;E 6 When is a nitrogen atom, R 6 does not exist; Subscript n 1 In each or one of the ligands, the number of which is defined by R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R4 and R 5 , and R 5 and R 6 R which does not form a group represented by the following formula (P) 1 , R 2 , R 3 , R 4 , R 5 , and R 6 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. When a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which they are bonded; the subscript n 1 In each ligand or one ligand, the number of which is defined by R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 When a plurality of are present, they may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded; Subscript n 2 In each or one of the ligands, the number of which is defined by A 1 -G 1 -A 2 represents an anionic bidentate ligand, G 1 A 1 and A 2 Represents an atomic group constituting a bidentate ligand together with A 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. [ka] [In the formula, The dotted line is E 1 , E2 , E 3 , E 4 , E 5 , or E 6 Showing bond with; Ring R C3 represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent, and when a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which each is bonded; Y a and Y b One of them is a single bond and the other is -C(R Ya )2-, where R Ya 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. When a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which they are bonded; when a plurality of R Ya may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded. [2] In the formula (0), the subscript n 1 In each or one of the ligands, the number of which is defined by R 2 and R 3 and (B) are combined with each other to form a group represented by formula (P). [3] The metal complex according to [1] or [2], wherein the formula (P) is represented by the following formula (P′): [ka] [In the formula, The dotted line is E 1 , E 2 , E 3 , E 4 , E 5 , or E 6 Showing bond with; Y a and Y brespectively represent Y in the formula (P). a and Y b Means the same as; R C31 , R C32 , R C33 and R C34 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; R C31 and R C32 , R C32 and R C33 , and R C33 and R C34 may be bonded to each other to form a ring together with the atoms to which they are bonded. [4] The metal complex according to [3], wherein the metal complex represented by formula (0) is a metal complex represented by the following formula (2-A1), the following formula (2-B1), or the following formula (2-C1): [ka] [ka] [ka] [In formula (2-A1), formula (2-B1), and formula (2-C1), M, n 1 , n 2 , X a , X b , E 1 , E 4 , E 5 , E 6 , R 1 , R 4 , R 5 , R 6 , and A 1 -G 1 -A 2 respectively represent M and n in the formula (0). 1 , n 2 , X a , Xb , E 1 , E 4 , E 5 , E 6 , R 1 , R 4 , R 5 , R 6 , and A 1 -G 1 -A 2 It means the same as;Y a and Y b respectively represent Y in the formula (P). a and Y b It has the same meaning as;R C31 , R C32 , R C33 , and R C34 are R in the formula (P′), C31 , R C32 , R C33 , and R C34 Means the same as; R in formula (2-A1) C11 and R C14 , R in formula (2-B1) C13 and R C14 and R in formula (2-C1) C11 and R C12 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; R C21 , R C22 , R C23 and R C24 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; the subscript n 1 In each or one of the ligands, the number of which is defined by R C11 and R C12 , R C13 and R C14 , R C21 and R C22 , RC22 and R C23 , and R C23 and R C24 may be bonded to each other to form a ring together with the atoms to which they are bonded. [5] The metal complex according to [4], wherein the metal complex represented by formula (2-A1) is a metal complex represented by the following formula (2-A1-1): [ka] [In the formula, M, n 1 , n 2 , E 1 , E 4 , E 5 , E 6 , R 1 , R 4 , R 5 , R 6 , and A 1 -G 1 -A 2 respectively represent M and n in the formula (0). 1 , n 2 , E 1 , E 4 , E 5 , E 6 , R 1 , R 4 , R 5 , R 6 , and A 1 -G 1 -A 2 It means the same as;Y a and Y b respectively represent Y in the formula (P). a and Y b It has the same meaning as;R C31 , R C32 , R C33 , and R C34 are R in the formula (P′), C31 , R C32 , R C33 , and R C34 It has the same meaning as;R C11 , R C14 , R C21 , R C22 , RC23 , and R C24 are R in the above formula (2-A1), C11 , R C14 , R C21 , R C22 , R C23 , and R C24 Means the same as; R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 and R C48 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; the subscript n 1 In each or one of the ligands, the number of which is defined by R C41 and R C42 , R C42 and R C43 , R C43 and R C44 , R C45 and R C46 , R C46 and R C47 , and R C47 and R C48 may be bonded to each other to form a ring together with the atoms to which they are bonded. [6] The ring R C1 , the ring R C2 or the ring R C3 has a group represented by the following formula (DA), the following formula (DB), or the following formula (DC) as a substituent: [ka] [In the formula, m DA1 , m DA2 and m DA3 each independently represents an integer of 0 or more; G DArepresents a nitrogen atom, an aromatic hydrocarbon group or a 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; Ar 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, which may have a substituent; DA may be the same or different.] [ka] [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 nitrogen atom, an aromatic hydrocarbon group or a 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 DArepresents an aryl group or a monovalent heterocyclic group, which may have a substituent; DA may be the same or different.] [ka] [In the formula, m DA1 represents an integer greater than or equal to 0; Ar DA1 represents an arylene group or a divalent heterocyclic group, which 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. [7] R that does not form a group represented by the formula (P) 1 , R 2 , R 3 , R 4 , R 5 , or R 6 is a group represented by the formula (DA), the formula (DB) or the formula (DC). [8] R that does not form a group represented by the formula (P) 4 or R 5 is a group represented by the formula (DA), the formula (DB), or the formula (DC). [9] The M is an iridium atom, and the n 1 The metal complex according to any one of [1] to [8], wherein

[10] [1] to [9], and at least one material selected from the group consisting of a host material, a light-emitting material other than the metal complex, an antioxidant, and a solvent; A composition comprising:

[11] The composition according to

[10] , wherein the host material contains at least one of a low molecular weight compound represented by the following formula (H-1) and a high molecular weight compound containing a constitutional unit represented by the following formula (Y): [ka] [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; n H1 When multiple are present, they may be the same or different; H2 If there are multiple n H2 may be the same or different; n H3 represents an integer greater than or equal to 0; L H1 is an arylene group, a divalent heterocyclic group, or -[C(R H11 )2]n H11 -, which may have a substituent; L H1 When multiple are present, they may be the same or different, and n H11 represents an integer between 1 and 10; R H11 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. H11 may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are attached; L H2 -N(-L H21 -R H21 )-represents a group represented by the formula: L H2 If there are multiple L H2 may be the same or different; L H21 represents a single bond, an arylene group, or a divalent heterocyclic group, each of which may have a substituent; RH21 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. [ka] [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.

[12] A light-emitting device comprising the metal complex according to any one of [1] to [9]. Effect of the Invention

[0009] According to the present invention, it is possible to provide a metal complex useful for producing a light-emitting device exhibiting an improved luminance life. In addition, 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. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] Preferred embodiments of the present invention will now be described in detail.

[0011] <Explanation of common terms> Terms commonly used in this specification have the following meanings unless otherwise specified.

[0012] Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, i-Pr represents an isopropyl group, and t-Bu represents a tert-butyl group.

[0013] The hydrogen atom may be a deuterium atom or a protium atom.

[0014] In the formula representing a metal complex, the solid line representing a bond to a central metal means a covalent bond or a coordinate bond.

[0015] A "low molecular weight compound" is a compound that does not have a molecular weight distribution and has a molecular weight of 1×10 4The following compound is meant:

[0016] "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 term "structural unit" refers to a unit that exists in a polymer compound in one or more instances. A structural unit that exists in a polymer compound in two or more instances is generally called a "repeating unit."

[0017] The polymer compound may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, and the like, or may be in 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 deteriorated when the polymer compound is used for producing a light-emitting device. The end group of the polymer compound is preferably a group conjugated with the main chain, and examples thereof include an aryl group or a monovalent heterocyclic group bonded to the main chain of the polymer compound via a carbon-carbon bond.

[0018] 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 3 to 30, and more preferably 4 to 20. 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 20. 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, and a dodecyl group. The alkyl group may be a group in which some or all of the hydrogen atoms in these groups are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and / or a fluorine atom. Examples of such alkyl groups include trifluoromethyl, pentafluoroethyl, perfluorobutyl, perfluorohexyl, perfluorooctyl, 3-phenylpropyl, 3-(4-methylphenyl)propyl, 3-(3,5-di-hexylphenyl)propyl, and 6-ethyloxyhexyl groups.

[0019] The number of carbon atoms of the "cycloalkyl group", not including the number of carbon atoms of the substituent, is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

[0020] 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 is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10, not including the number of carbon atoms of the substituent. 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, and a 4-phenylphenyl group. The aryl group may be a group in which some or all of the hydrogen atoms in these groups are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and / or a fluorine atom.

[0021] 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, and a lauryloxy group. The alkoxy group may be a group in which some or all of the hydrogen atoms in these groups are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and / or a fluorine atom, etc.

[0022] The number of carbon atoms in the "cycloalkoxy group" is usually 3 to 40, and preferably 4 to 10, not including the number of carbon atoms of the substituents. The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group.

[0023] The number of carbon atoms in the "aryloxy group" is usually 6 to 60, and preferably 6 to 48, not including the number of carbon atoms of substituents. 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-anthracenyloxy group, a 9-anthracenyloxy group, and a 1-pyrenyloxy group. The aryloxy group may be a group in which some or all of the hydrogen atoms in these groups are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and / or a fluorine atom, etc.

[0024] 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 the carbon atoms or heteroatoms constituting the ring of a heterocyclic compound. Among 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 the carbon atoms or heteroatoms constituting the ring of an aromatic heterocyclic compound is preferred. The term "aromatic heterocyclic compound" refers to compounds 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, and dibenzophosphole, as well as compounds in which an aromatic ring is condensed with a heterocycle, even if the heterocycle itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, and benzopyran.

[0025] The monovalent heterocyclic group has usually 2 to 60 carbon atoms, and preferably 4 to 20 carbon atoms, not including the number of carbon atoms of the substituent. The monovalent heterocyclic group may have a substituent. Examples of the monovalent heterocyclic group 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, and a triazinyl group. The monovalent heterocyclic group may be a group in which some or all of the hydrogen atoms in these groups are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, and / or a cycloalkoxy group.

[0026] The term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0027] The "amino group" may have a substituent, and is preferably a substituted amino group (preferably a secondary amino group or a tertiary amino group, more preferably a tertiary amino group). The substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. When the amino group has a plurality of substituents, they may be the same or different, and may be bonded to each other to form a ring together with the nitrogen atom to which they are bonded. Examples of the substituted amino group include dialkylamino groups (e.g., dimethylamino group, diethylamino group), dicycloalkylamino groups, diarylamino groups (e.g., diphenylamino group), bis(4-methylphenyl)amino group, bis(4-tert-butylphenyl)amino group, and bis(3,5-di-tert-butylphenyl)amino group.

[0028] The "alkenyl group" may be either linear or branched. The number of carbon atoms in a linear alkenyl group, not including the number of carbon atoms in the substituent, is usually 2 to 30, and preferably 3 to 20. The number of carbon atoms in a branched alkenyl group, not including the number of carbon atoms in the substituent, is usually 3 to 30, and preferably 4 to 20. The number of carbon atoms in a "cycloalkenyl group" is usually 3 to 30, and preferably 4 to 20, not including the number of carbon atoms of substituents. The alkenyl group and the cycloalkenyl group may have a substituent. Examples of the alkenyl group include vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, and 7-octenyl group, as well as groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent. Examples of the cycloalkenyl group include cyclohexenyl group, cyclohexadienyl group, cyclooctatrienyl group, and norbornylenyl group, as well as groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent.

[0029] The "alkynyl group" may be either linear or branched. The number of carbon atoms in a linear alkynyl group, not including the carbon atoms of the substituent, is usually 2 to 20, and preferably 3 to 20. The number of carbon atoms in a branched alkynyl group, not including the carbon atoms of the substituent, is usually 4 to 30, and preferably 4 to 20. The number of carbon atoms in the "cycloalkynyl group" is usually 4 to 30, and preferably 4 to 20, not including the carbon atoms of the substituents. The alkynyl group and the cycloalkynyl group may have a substituent. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, and a 5-hexynyl group, as well as groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent. Examples of the cycloalkynyl group include a cyclooctynyl group, as well as groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent.

[0030] 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 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent. 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, and a chrysenediyl group, as well as 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 the following formulae (A-1) to (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

[0031] [ka]

[0032] [ka]

[0033] [ka]

[0034] [ka]

[0035] In the above formulas (A-1) to (A-20), 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.

[0036] The divalent heterocyclic group has usually 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms, and more preferably 4 to 15 carbon atoms, not including the number of carbon atoms of the substituent. 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 from pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, or triazole. The divalent heterocyclic group may be a group 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 the following formulae (AA-1) to (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] [ka]

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] In the above formulas (AA-1) to (AA-34), R and R a R and R in the above formulas (A-1) to (A-20) a It has the same meaning as:

[0045] 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, and / or radical reaction, etc. The crosslinking group is preferably a group represented by any one of the following formulae (B-1) to (B-17). These groups may have a substituent.

[0046] [ka]

[0047] 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.

[0048] <Metal complex> The metal complex of this embodiment is a metal complex represented by the above formula (0).

[0049] In the above formula (0), the subscript n 1 It is believed that the ligands, the number of which is defined by the formula (I), improve the electron transport property of the metal complex of this embodiment. The improvement in the electron transport property of the metal complex leads to a reduction in the driving voltage and an expansion of the light-emitting region in a light-emitting device produced using the metal complex, and as a result, leads to an improvement in the luminance life of the light-emitting device.

[0050] The metal complex of this embodiment is usually a metal complex that exhibits phosphorescence at room temperature (25° C.), and is preferably a metal complex that exhibits luminescence from a triplet excited state at room temperature.

[0051] The metal complex of this embodiment is a compound having a central metal M and a subscript n 1 The ligands whose number is specified by the subscript n 2 and ligands whose number is regulated by

[0052] Preferably, n 1 If is 2 or 3, the subscript n 1 The ligands whose numbers are defined by are identical to each other.

[0053] Preferably, n 2 If is 2, then the subscript n 2 The ligands whose numbers are defined by are identical to each other.

[0054] M is preferably an iridium atom because the light-emitting device using the metal complex of this embodiment exhibits high external quantum efficiency.

[0055] n 2 is preferably 0 because the light-emitting element using the metal complex of this embodiment exhibits high external quantum efficiency.

[0056] Ring R C1 , ring R C2 and ring R C3 In the above formula, the number of carbon atoms in the aromatic hydrocarbon ring is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms in the substituent.

[0057] Ring R C1 , ring R C2 and ring R C3Examples of the aromatic hydrocarbon ring represented by the formula (I) include a benzene ring, a naphthalene ring, an anthracene ring, an indene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a pyrene ring, a chrysene ring and a triphenylene ring. Of these, a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring or a dihydrophenanthrene ring is preferable, a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring is more preferable, and a benzene ring is even more preferable. These rings may have a substituent.

[0058] Ring R C1 , ring R C2 and ring R C3 In the above formula, the number of carbon atoms in the aromatic heterocycle is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15, not including the number of carbon atoms in the substituent.

[0059] Ring R C1 , ring R C2 and ring R C3Examples of the aromatic heterocycle represented by the formula (I) include a pyrrole ring, a diazole ring, a triazole ring, a furan ring, a thiophene ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, a triazaphenanthrene ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzosilole ring, a dibenzophosphole ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a phenoxazine ring, a phenothiazine ring, Examples of the ring include a dihydroacridine ring and a dihydrophenazine ring. Of these, a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, an azaanthracene ring, a diazaphenanthrene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a phenoxazine ring, a phenothiazine ring, a dihydroacridine ring, or a dihydrophenazine ring is preferable, a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a dibenzofuran ring, a dibenzothiophene ring, or a carbazole ring is more preferable, and a pyridine ring or a diazabenzene ring is even more preferable, and these rings may have a substituent.

[0060] Ring R C3 is preferably an aromatic hydrocarbon ring, particularly a benzene ring, since this facilitates synthesis.

[0061] Ring R C1 , ring R C2 and ring R C3 Among these, it is preferable that at least one of them is an aromatic hydrocarbon ring (particularly a benzene ring), and it is more preferable that two or more of them are aromatic hydrocarbon rings (particularly a benzene ring). C1 , ring R C2 and ring R C3 It is more preferable that all of them are aromatic hydrocarbon rings (particularly benzene rings).

[0062] Ring R C1 , ring R C2 and ring R C3The substituent that may be contained in is preferably 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, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, further preferably an aryl group or a monovalent heterocyclic group, and particularly preferably a monovalent heterocyclic group. These groups may further have a substituent.

[0063] Ring R C1 , ring R C2 and ring R C3 In the substituent that may be present, the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 25, not including the number of carbon atoms of the substituent.

[0064] Ring R C1 , ring R C2 and ring R C3 Among the substituents that may be possessed by the aryl group, for example, a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring is removed from a benzene ring, a naphthalene ring, an anthracene ring, an indene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a pyrene ring, a chrysene ring, a triphenylene ring, or a ring in which these rings are condensed, is mentioned. Preferably, it is a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring is removed from a benzene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, or a triphenylene ring, more preferably, it is a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring is removed from a benzene ring, a fluorene ring, or a spirobifluorene ring, and even more preferably, it is a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring is removed from a benzene ring, and these groups may further have a substituent.

[0065] Ring R C1 , ring R C2 and ring R C3 Among the substituents which may be possessed by the alkyl group, the aryloxy group is, for example, -O-Ar 2 (Ar2 represents an aryl group, and the aryl group may have a substituent. 2 Examples and preferred ranges of the aryl group are the ring R C1 , ring R C2 and ring R C3 The examples and preferred range of the aryl group as the substituent that may be possessed by the alkyl group are the same as those of the aryl group which may be possessed by the alkyl group.

[0066] Ring R C1 , ring R C2 and ring R C3 Among the substituents which may be possessed by the group, the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 to 30, and more preferably 3 to 15, not including the number of carbon atoms of the substituent.

[0067] Ring R C1 , ring R C2 and ring R C3Among the substituents which may be possessed by the formula, examples of the monovalent heterocyclic group include a pyrrole ring, a diazole ring, a triazole ring, a furan ring, a thiophene ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a triazaanthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, a triazaphenanthrene ring, a dibenzofuran ring, a dibenzothiophene ring, a dibenzo Examples of the ring include a silole ring, a dibenzophosphole ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a phenoxazine ring, a phenothiazine ring, a dihydroacridine ring, a dihydrophenazine ring, or a ring in which an aromatic ring is condensed with any of these rings, from which one hydrogen atom directly bonded to a carbon atom or heteroatom constituting the ring has been removed. Preferred are a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, an azacarbazo ring, and a cycloalkyl ring. a group in which one hydrogen atom directly bonded to a carbon atom or hetero atom constituting the ring is removed from a pyridine ring, a diazacarbazole ring, a phenoxazine ring, a phenothiazine ring, a dihydroacridine ring, or a dihydrophenazine ring, and more preferably a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring is removed from a pyridine ring, a diazabenzene ring, a triazine ring, a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a phenoxazine ring, a phenothiazine ring, a dihydroacridine ring, or a dihydrophenazine ring. or a group in which one hydrogen atom directly bonded to a heteroatom constituting the ring has been removed, more preferably a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring or a heteroatom has been removed from a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a phenoxazine ring, a phenothiazine ring, a dihydroacridine ring, or a dihydrophenazine ring, and particularly preferably a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring has been removed from a dibenzofuran ring or a dibenzothiophene ring, and these rings may have a substituent.

[0068] Ring R C1 , ring R C2 and ring R C3Among the substituents that may be possessed by the amino group, the substituted amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. Examples and preferred ranges of the aryl group as the substituent possessed by the amino group are as follows: C1 , ring R C2 and ring R C3 Examples and preferred ranges of the aryl group as a substituent that may be possessed by the amino group are the same as those of the monovalent heterocyclic group as a substituent that may be possessed by the ring R C1 , ring R C2 and ring R C3 The examples and preferred range of the monovalent heterocyclic group as the substituent that may be possessed by are the same as those of the monovalent heterocyclic group that may be possessed by the group.

[0069] Ring R C1 , ring R C2 and ring R C3 Among the substituents which may be possessed by the group, as the halogen atom, a fluorine atom or a chlorine atom is preferable, and a fluorine atom is more preferable.

[0070] Ring R C1 , ring R C2 and ring R C3 The substituent that may be further substituted by the substituent that may be substituted by the substituent is preferably 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, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, further preferably an alkyl group or an aryl group, and particularly preferably an aryl group, and these groups may further have a substituent (for example, an alkyl group).

[0071] Ring R C1 , ring R C2 and ring R C3 The aryl group as a substituent which the optionally substituted aryl group may further have is preferably a phenyl group, and this phenyl group may further have a substituent (for example, an alkyl group).

[0072] Ring R C1, ring R C2 and ring R C3 The alkyl group as a substituent which the optionally substituted group may further have is preferably an alkyl group having 3 to 9 carbon atoms.

[0073] Ring R C1 , ring R C2 and ring R C3 Examples and preferred ranges of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom which may be further substituted by the substituent which may be substituted by the ring R C1 , ring R C2 and ring R C3 The examples and preferred ranges of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom as the substituent that may be possessed by the alkyl group are the same as those of the alkyl group, the alkyl group, the aryloxy group, the monovalent heterocyclic group, the substituted amino group and the halogen atom which may be possessed by the alkyl group.

[0074] Since the long-term deterioration of the light-emitting device containing the metal complex of this embodiment is further suppressed, the ring R C2 and ring R C3 At least one of the rings R C2 ) has an aryl group or a monovalent heterocyclic group as a substituent, and / or R 3 , R 4 and R 5 At least one of the following (especially R 4 or R 5 It is preferable that the ring R is an aryl group or a monovalent heterocyclic group. C2 and ring R C3 At least one of the rings R C2 ) has an aryl group or a monovalent heterocyclic group as a substituent, and R 3 , R 4 and R 5 At least one of the following (especially R 4 or R 5 ) is particularly preferably an aryl group or a monovalent heterocyclic group.

[0075] Ring R C1 , ring R C2 and ring R C3 At least one of the rings R C2) has an aryl group or a monovalent heterocyclic group as a substituent, and / or R 3 , R 4 and R 5 At least one of the following (especially R 4 or R 5 When is an aryl group or a monovalent heterocyclic group, the aryl group is particularly preferably a phenyl group, and this group may further have a substituent.

[0076] Ring R C1 , ring R C2 and ring R C3 (Especially Ring R C2 At least one of R has an aryl group or a monovalent heterocyclic group as a substituent, and / or R 3 , R 4 and R 5 At least one of the following (especially R 4 or R 5 ) is an aryl group or a monovalent heterocyclic group, the monovalent heterocyclic group is particularly preferably a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring has been removed from a pyrimidine ring or a triazine ring (particularly a triazine ring), and these groups may further have a substituent.

[0077] Since the long-term deterioration of the light-emitting device containing the metal complex of this embodiment is further suppressed, the ring R C1 , ring R C2 and ring R C3 At least one of the rings R C1 , ring R C2 and ring R C3 It is more preferable that at least one of the rings R C2 More preferably, has an aryl group as a substituent.

[0078] Ring R C1 , ring R C2 and ring R C3 The aryl group as the substituent of is particularly preferably a phenyl group, and this phenyl group may further have a substituent.

[0079] Ring R C1 , ring R C2 and ring R C3 The monovalent heterocyclic group as the substituent of is particularly preferably a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring has been removed from a pyrimidine ring or triazine ring (particularly a triazine ring), and these groups may further have a substituent.

[0080] Ring R C1 , ring R C2 , or ring R C3 may have a group represented by the above formula (DA), the above formula (DB) or the above formula (DC) as a substituent. C1 , ring R C2 , or ring R C3 However, when the metal complex has a group represented by the above formula (DA), the above formula (DB) or the above formula (DC) as a substituent, aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0081] Ring R C3 Examples of the group include the group represented by the above formula (P').

[0082] R C31 , R C32 , R C33 and R C34 Examples and preferred ranges of an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group and a halogen atom as the ring R C1 , ring R C2 and ring R C3 The examples and preferred ranges of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom as the substituent that may be possessed by are the same as those of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom which may be possessed by the alkyl group.

[0083] R C31 , R C32 , R C33 and R C34 Examples and preferred ranges of the substituents which may be further substituted by the ring R C1 , ring R C2and ring R C3 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.

[0084] R C31 , R C32 , R C33 and R C34 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and even more preferably a hydrogen atom, an alkyl group, or an aryl group, because this facilitates the synthesis of the metal complex of this embodiment.

[0085] R C31 , R C32 , R C33 or R C34 R may be a group represented by the above formula (DA), the above formula (DB) or the above formula (DC). C31 , R C32 , R C33 or R C34 is a group represented by the above formula (DA), the above formula (DB) or the above formula (DC), aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0086] The metal complex of this embodiment is R 2 and R 3 , R 3 and R 4 , and R 5 and R 6 More preferably, a metal complex is a group represented by the above formula (P), 2 and R 3 , and R 3 and R 4 More preferably, a metal complex is a metal complex in which one combination of the following is taken together to form a group represented by the above formula (P); 2 and R 3Particularly preferred is a metal complex in which the combination of R 2 and R 3 A metal complex in which the combination of the above is taken together to form a group represented by the above formula (P) is hereinafter referred to as "metal complex X".

[0087] Examples of the metal complex X include metal complexes represented by the above formula (2-A1), (2-B1), or (2-C1). Since they can be easily synthesized, the metal complexes represented by the above formula (2-A1) or (2-B1) are more preferred, and the metal complexes represented by the above formula (2-A1) are even more preferred.

[0088] E 1 , E 2 , E 3 , E 4 , E 5 and E 6 is preferably a carbon atom since this facilitates the synthesis of the metal complex of the present embodiment.

[0089] X a and X b Since the metal complex of this embodiment can be easily synthesized, X a -C(R Xa )2-, or -C(R Xa )2-C(R Xa )2-, and X b is preferably a group represented by a single bond, a -C(R Xa )2-, and X b It is more preferable that the group is represented by a single bond.

[0090] X a Or X b -C(R Xa )2-, R Xa are each independently preferably an alkyl group (particularly an alkyl group having 1 to 8 carbon atoms) or an aryl group (particularly a phenyl group), or -C(R Xa)2- is preferably a group represented by the following formula (XAB-1).

[0091] [ka] [In the formula, R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 and R C48 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.

[0092] In the above formula (XAB-1), R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 and R C48 are preferably each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

[0093] Y a and Y b Since the metal complex of this embodiment can be easily synthesized, Y a is a single bond, and Y b -C(R Ya )2- is preferred.

[0094] Y a Or Y b -C(R Ya )2-, R Ya are each independently preferably an alkyl group (particularly an alkyl group having 1 to 8 carbon atoms) or an aryl group (particularly a phenyl group) (more preferably an alkyl group), or -C(R Ya )2- is preferably a group represented by the above formula (XAB-1).

[0095] R 1 , R 2 , R 3 , R 4 , R 5 and R 6 Examples and preferred ranges of an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, and a halogen atom as the ring R C1 , ring R C2 and ring R C3 The examples and preferred ranges of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom as the substituent that may be possessed by are the same as those of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom which may be possessed by the alkyl group.

[0096] R 1 , R 2 , R 3 , R 4 , R 5 and R 6 Examples and preferred ranges of the substituents which may be further substituted by the ring R C1 , ring R C2 and ring R C3 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.

[0097] R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and even more preferably a hydrogen atom, because this facilitates the synthesis of the metal complex of the present embodiment.

[0098] Since the long-term deterioration of the light-emitting element containing the metal complex of this embodiment is further suppressed, R 1 , R 2 , R 3 , R 4 , R 5 or R 6 At least one of the following (especially R 4or R 5 ) is preferably an aryl group or a monovalent heterocyclic group.

[0099] R 1 , R 2 , R 3 , R 4 , R 5 or R 6 At least one of the following (especially R 4 or R 5 When is an aryl group, the aryl group is particularly preferably a phenyl group, and this phenyl group may further have a substituent.

[0100] R 1 , R 2 , R 3 , R 4 , R 5 or R 6 At least one of the following (especially R 4 or R 5 ) is a monovalent heterocyclic group, the monovalent heterocyclic group is particularly preferably a group in which one hydrogen atom directly bonded to a carbon atom constituting the ring has been removed from a triazine ring, and the monovalent heterocyclic group may further have a substituent.

[0101] R 1 , R 2 , R 3 , R 4 , R 5 or R 6 (Especially R 3 or R 5 R ) may be a group represented by the above formula (DA), the above formula (DB) or the above formula (DC). 1 , R 2 , R 3 , R 4 , R 5 or R 6 (Especially R 3 or R 5 ) has a group represented by the above formula (DA), the above formula (DB) or the above formula (DC), aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0102] In particular, R 3 , R 4 or R 5 (And R 4 or R 5 ) may be a group represented by the above formula (DA), the above formula (DB) or the above formula (DC). 3 , R 4 or R 5 (And R 4 or R 5 ) has a group represented by the above formula (DA), the above formula (DB) or the above formula (DC), aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0103] An example of the metal complex represented by the above formula (2-A1) is the metal complex represented by the above formula (2-A1-1).

[0104] R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 and R C48 Examples and preferred ranges of an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group and a halogen atom as the ring R C1 , ring R C2 and ring R C3 The examples and preferred ranges of the aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group and halogen atom as the substituent that may be possessed by the alkyl group are the same as those of the alkyl group, the alkyl group, the aryloxy group, the monovalent heterocyclic group, the substituted amino group and the halogen atom which may be possessed by the alkyl group.

[0105] R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 and R C48 Examples and preferred ranges of the substituents which may be further substituted by the ring R C1 , ring R C2 and ring RC3 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.

[0106] R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 and R C48 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and even more preferably a hydrogen atom, because this facilitates the synthesis of the metal complex of the present embodiment.

[0107] R C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 or R C48 R may be a group represented by the above formula (DA), the above formula (DB) or the above formula (DC). C41 , R C42 , R C43 , R C44 , R C45 , R C46 , R C47 or R C48 However, when the metal complex has a group represented by the above formula (DA), the above formula (DB) or the above formula (DC), aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0108] <Groups represented by formulae (DA) to (DC)> m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7is 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 DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.

[0109] G DA is preferably an aromatic hydrocarbon group or a heterocyclic group, and more preferably a group consisting of a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, or a carbazole ring, by removing three hydrogen atoms directly bonded to carbon atoms or nitrogen atoms constituting the ring, and these groups may have a substituent.

[0110] G DA The substituent which may be substituted is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may be substituted.

[0111] G DA is preferably a group represented by the following formulae (GDA-11) to (GDA-15).

[0112] [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 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 further have a substituent; R DA When multiple are present, they may be the same or different.

[0113] Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7 is preferably a phenylene group, a fluorenediyl group, or a carbazolediyl group, and more preferably a group represented by the following formulas (ArDA-1) to (ArDA-5), and these groups may have a substituent.

[0114] Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and 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.

[0115] [ka] [In the formula, R DA is R in the above formulas (GDA-11) to (GDA-15). DA Means the same as; R DB 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; R DB When multiple are present, they may be the same or different.

[0116] T DA The substituent that may be substituted 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, still more preferably an alkyl group or an aryl group, and particularly preferably an alkyl group, and these groups may further have a substituent.

[0117] T DA is preferably a group represented by the following formulae (TDA-1) to (TDA-3), and more preferably a group represented by the following formula (TDA-1).

[0118] [ka] [In the formula, R DA and R DB R in the above formulas (ArDA-1) to (ArDA-5) DA and R DB It has the same meaning as:

[0119] Examples of the group represented by formula (DA) above include groups represented by formulas (DA-1) to (DA-12) below.

[0120] [ka]

[0121] [ka] [In the formula, R D represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and these groups may have a substituent; R D When multiple are present, they may be the same or different.

[0122] Examples of the group represented by formula (DB) include groups represented by formulas (DB-1) to (DB-7) below.

[0123] [ka]

[0124] [ka] [In the formula, R D R in the above formulas (DA-1) to (DA-12) D It has the same meaning as:

[0125] Examples of the group represented by formula (DC) above include groups represented by formulas (DC-1) to (DC-14) below.

[0126] [ka] [In the formula, R D R in the above formulas (DA-1) to (DA-12) D It has the same meaning as:

[0127] In one embodiment of the present disclosure, the metal complex is a ring R C1 , ring R C2 , or ring R C3 The metal complex has a structure in which a group represented by the above formula (DA), formula (DB), or formula (DC) is bonded to the ring R C1 , ring R C2 , or ring R C3 When the metal complex has a structure in which a group represented by the above formula (DA), formula (DB), or formula (DC) is bonded to the metal complex, aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0128] In another embodiment of the present disclosure, the metal complex is represented by the ring R C2Or ring R C3 to which a group represented by the above formula (DA), formula (DB), or formula (DC) is bonded, or R 3 Or R 5 is a group represented by the above formula (DA), formula (DB), or formula (DC). C2 Or ring R C3 to which a group represented by the above formula (DA), formula (DB), or formula (DC) is bonded, or R 3 Or R 5 is a group represented by the above formula (DA), formula (DB), or formula (DC), aggregation of the metal complex is suppressed, and the luminance life of the light-emitting element formed using the metal complex may be further improved.

[0129] <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.

[0130] [ka]

[0131] [ka]

[0132] [ka] [In the formula, * denotes the site that binds to M; R L1represents 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.

[0133] Specific examples of the metal complex of this embodiment include metal complexes represented by the following formulae (Ir-101) to (Ir-136).

[0134] [ka]

[0135] [ka]

[0136] [ka]

[0137] [ka]

[0138] [ka]

[0139] [ka]

[0140] [ka]

[0141] [ka]

[0142]

change

[0143]

change

[0144]

change

[0145]

change

[0146]

change

[0147]

change

[0148]

change

[0149]

change

[0150]

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[0151]

change

[0152] The metal complexes of the present embodiment may be used alone or in combination of two or more kinds.

[0153] 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).

[0154] <Method for producing metal complex represented by formula (0)> A method for producing the above-mentioned metal complex X, which is a representative metal complex among the metal complexes of this embodiment, will be described.

[0155] [Manufacturing method 1] Metal complex X can be produced, for example, by reacting a compound that serves 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. Among the metal complexes represented by the above formula (0), metal complexes other than metal complex X can also be produced in the same manner.

[0156] Among the metal complexes X, those in which M is an iridium atom and n1 is 2 or 3 include, for example, (i) a step A1 of synthesizing a metal complex represented by the following formula (M2-2) by reacting a compound represented by the following formula (M2-1) with an iridium compound or a hydrate thereof; and (ii) A metal complex represented by the following formula (M2-2) and a compound represented by the following formula (M2-1) 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:

[0157] [ka] [ka] [In the above formula (M2-1) and formula (M2-2), ring R C1 , ring R C2 , ring R C3 , X a , X b , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 and E 6 are the rings R in the above formula (0), C1 , ring R C2 , ring R C3 , X a , X b , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 and E 6 In each of the ligands constituting the formula (M2-1) and the formula (M2-2), the ring R C1 , ring R C2 , and ring R C3 At least one ring among these has a group represented by the above formula (DA), formula (DB) or formula (DC).

[0158] 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.

[0159] 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.

[0160] 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.

[0161] In step A1, the amount of the compound represented by formula (M2-1) is usually 2 to 20 moles per mole of the iridium compound or a hydrate thereof.

[0162] In step B1, a compound represented by formula (M2-1) or A 1 -G 1 -A 2 The amount of the ligand precursor represented by the formula (M2-2) is usually 1 to 100 mol per 1 mol of the metal complex represented by the formula (M2-2).

[0163] 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 (M2-2).

[0164] The compound represented by the above formula (M2-1) 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.

[0165] [ka] [In formula (M1-3), ring R C1 , ring R C2 , ring R C3 , X a , X b , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 and E 6 are the rings R in the above formula (0), C1 , ring R C2 , ring R C3 , X a , X b , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 and E 6 has the same meaning as; except that the ring R C1 , ring R C2 , and ring R C3 At least one ring of the formula (M2-1) is selected from the group represented by formula (DA), formula (DB) or formula (DC), and is replaced by -B(OR W1 ) a group represented by the formula (2), an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom as a substituent; R W1 represents 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. [In formula (M1-4), Z 1represents a group represented by the above formula (DA), formula (DB) or formula (DC). 1 -B(OR W1 ) a group represented by the formula (2), 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 W1 is R in formula (M1-3). W1 It has the same meaning as:

[0166] -B(OR W1 Examples of the group represented by formula (W-2) include groups represented by the following formulae (W-1) to (W-10).

[0167] [ka]

[0168] W 1 Examples of the alkylsulfonyloxy group represented by the formula (I) include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group. W 1 An example of the arylsulfonyloxy group represented by the following formula (I) is a p-toluenesulfonyloxy group.

[0169] W 1 As the group represented by the formula (W-7), a chlorine atom, a bromine atom, or the group represented by the formula (W-7) is more preferable because the coupling reaction between the compound represented by the formula (M1-4) and the metal complex represented by the formula (M1-3) proceeds easily.

[0170] Ring R C1 , ring R C2 , and ring R C3 The alkylsulfonyloxy group, cycloalkylsulfonyloxy group and arylsulfonyloxy group as the substituents which at least one ring of the formula (DA), formula (DB) or formula (DC) has instead of the group represented by the above formula (DA), formula (DB) or formula (DC) are each represented by W 1The alkylsulfonyloxy group, the cycloalkylsulfonyloxy group and the arylsulfonyloxy group represented by the following formula (1) have the same meaning as the alkylsulfonyloxy group, the cycloalkylsulfonyloxy group and the arylsulfonyloxy group represented by the following formula (1):

[0171] Z 1 As the alkyl group, the group represented by the above formula (DA) is preferable, and the groups represented by the above formulae (D-A1) to (D-A3) are more preferable.

[0172] The coupling reaction between the compound represented by the above formula (M1-3) and the compound represented by the above formula (M1-4) is usually carried out in a solvent. The solvent, reaction time and reaction temperature used may be the same as those described in step A1 and step B1.

[0173] In the coupling reaction between the compound represented by the above formula (M1-3) and the compound represented by the above formula (M1-4), the amount of the compound represented by the formula (M1-4) is usually 0.05 to 20 moles per mole of the compound represented by the formula (M1-3).

[0174] Examples of the compound represented by the above formula (M1-4) include Z 1 is a group represented by the above formula (D-A1) to formula (D-A3), and W 1 -B(OR W1 ) 2, a trifluoromethanesulfonyloxy group, a bromine atom or an iodine atom.

[0175] The compound represented by the following formula (M1-4-1), which is one embodiment of the compound represented by the above formula (M1-4), can be synthesized, for example, by the following method.

[0176] [ka] [In the formula, R p1 represents an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group; R p1When a plurality of np1 are present, they may be the same or different; np1 represents an integer of 0 to 5; a plurality of np1 may be the same or different; W 2 -B(OR W1 ) a group represented by the formula (2), 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.]

[0177] The compound represented by the above formula (M1-4-1) can be produced, for example, by coupling reaction between the compound represented by the above formula (M1-4-1a) and the compound represented by the above formula (M1-4-1b). This coupling reaction may be the same as that described for the compound represented by the above formula (M2-1).

[0178] The compound represented by the following formula (M1-4-2), which is one embodiment of the compound represented by the above formula (M1-4), can be synthesized, for example, by the following method.

[0179] [ka] [In the formula, R p1 , n p1 and W 2 is R in the above formula M(1-4-1) and formula M(1-4-1b). p1 , n p1 and W 2 It has the same meaning as:

[0180] The compound represented by the above formula (M1-4-2c) can be produced, for example, by coupling reaction between the compound represented by the above formula (M1-4-2a) and the compound represented by the above formula (M1-4-2b). This coupling reaction may be the same as that described for the compound represented by the above formula (M2-1).

[0181] The compound represented by the above formula (M1-4-2) can be synthesized, for example, by subjecting a compound represented by the above formula (M1-4-2c) and a compound represented by the above formula (M1-4-2d) to the Ishiyama-Miyaura-Hartwig reaction.

[0182] The compound represented by the above formula (M1-3) can be produced, for example, by coupling reaction between a compound represented by the following formula (M1-5) and a compound represented by the following formula (M1-6). This coupling reaction may be the same as that described for the compound represented by the above formula (M2-1).

[0183] [ka] [In formula (M1-5), ring R C1 , ring R C2 , X a and X b are the rings R in the above formula (0), C1 , ring R C2 , X a and X b Means the same as; In formula (M1-6), ring R C3 , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 and E 6 are the rings R in the above formula (0), C3 , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 and E 6 has the same meaning as; except that the ring R C1 , ring R C2 , and ring R C3At least one ring of the formula (DA), formula (DB) or formula (DC) is replaced by -B(OR W1 ) a group represented by the formula (2), an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom as a substituent; W 3 and W 4 are each independently -B(OR W1 ) a group represented by the formula (2), 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.]

[0184] Among the metal complexes X, those in which M is an iridium atom and n1 is 1 include, for example, (i)A 1 -G 1 -A 2 A step A1' of reacting a precursor of a ligand represented by the following formula (I): with an iridium compound or a hydrate thereof; and (ii) Step B1', in which the metal complex obtained in Step A1' is reacted with the compound represented by the above formula (M2-1) The composition can be produced by a method comprising the steps of: Step A1' and step B1' can be carried out in accordance with step A1 and step B1, respectively.

[0185] [Manufacturing method 2] The above metal complex X can also be produced, for example, by a method of reacting a precursor of the metal complex with a precursor of the ligand of the metal complex.

[0186] Metal complex X can be produced, for example, by coupling reaction of the compound represented by formula (M1-4) above with a metal complex represented by formula (M1-7) below. This coupling reaction may be the same as that described for the compound represented by formula (M2-1) above.

[0187] [ka] [In formula (M1-7), n1, n2, ring R C1 , ring R C2 , ring R C3 , X a , X b , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 , E 6 , and A 1 -G 1 -A 2 respectively represent n1, n2, and ring R in the above formula (0). C1 , ring R C2 , ring R C3 , X a , X b , Y a , Y b , R 1 , R 4 , R 5 , R 6 , E 1 , E 4 , E 5 , E 6 , and A 1 -G 1 -A 2 except that the subscript n 1 In each or one of the ligands, the number of which is defined by C1 , ring R C2 , and ring R C3 At least one ring of the formula (DA), formula (DB) or formula (DC) is replaced by -B(OR W1 ) a group represented by the formula (2), an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom as a substituent; R W1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an amino group, and these groups may have a substituent. W1may 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.

[0188] The metal complex represented by the above formula (M1-7) can be synthesized, for example, by using the compound represented by the above formula (M1-3) instead of the compound represented by the above formula (M2-1) in step A1 and step B1 of the above "production method 1".

[0189] The compounds, catalysts and solvents used in the reactions explained in the above section "<Production method of metal complex represented by formula (0)>" may each be used alone or in combination of two or more kinds.

[0190] <Composition> The composition of the present embodiment contains at least one material selected from the group consisting of a host material, a light-emitting material different from the metal complex of the present embodiment, an antioxidant, and a solvent, and the metal complex of the present embodiment.

[0191] The composition of the present embodiment may contain one type of metal complex of the present embodiment alone, or two or more types of metal complexes of the present embodiment.

[0192] [Host material] The "host material" is a material having at least one function selected from hole injection, hole transport, electron injection, and electron transport. The host material can be used together with a guest material to form a composition. An example of the guest material is the metal complex of this embodiment. By forming a composition with the metal complex of this embodiment and a host material, the luminance life of the light-emitting element obtained by using the metal complex of this embodiment becomes better. In the composition of this embodiment, the host material may be contained alone or in combination of two or more types.

[0193] 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 parts by mass to 80 parts by mass, preferably 0.05 parts by mass to 40 parts by mass, more preferably 0.1 parts by mass to 20 parts by mass, and even more preferably 1 part by mass 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.

[0194] The lowest excited triplet state (T1) of the host material is preferably at an energy level equivalent to or higher than the lowest excited triplet state (T1) of the metal complex of this embodiment, since this leads to a longer luminance life of the light-emitting element obtained by using the composition of this embodiment.

[0195] As the host material, since the light-emitting device obtained by using the composition of this embodiment can be produced 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.

[0196] The host material is classified into a low molecular weight compound used as a host material (hereinafter also referred to as a "low molecular weight host") and a high molecular weight compound used as a host material (hereinafter also referred to as a "high molecular weight host"). Examples of the host material include the following preferred low molecular weight hosts and high molecular weight hosts, as well as the following hole injection materials, hole transport materials, electron injection materials, and electron transport materials.

[0197] <Small molecule host> The low molecular weight host is preferably a compound represented by the following formula (H-1).

[0198] [ka] [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 H2Each independently represents 0 or 1. H1 When multiple are present, they may be the same or different; H2 If there are multiple n H2 may be the same or different; n H3 represents an integer greater than or equal to 0; L H1 is an arylene group, a divalent heterocyclic group, or -[C(R H11 )2]n H11 -, which may have a substituent; L H1 When multiple are present, they may be the same or different; H11 represents an integer between 1 and 10; R H11 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; H11 may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are attached; L H2 -N(-L H21 -R H21 )-represents a group represented by the formula: L H2 If there are multiple L H2 may be the same or different; L H21 represents a single bond, an arylene group, or a divalent heterocyclic group, and these groups may have a substituent; R 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.

[0199] Ar H1 and Ar H2is 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, and

[0133] Preferably, the aryl group is a phenyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group, or an azacarbazolyl group; more preferably, the aryl group is a phenyl group, a pyridyl group, a carbazolyl group, or an azacarbazolyl group; still more preferably, the aryl group is a phenyl group, a pyridyl group, a carbazolyl group, or an azacarbazolyl group; particularly preferably, the aryl group is a group represented by the above formula (TDA-1) or formula (TDA-3); and especially preferably, the aryl group is a group represented by the above formula (TDA-3), and these groups may have a substituent.

[0200] 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, or a monovalent heterocyclic group, more preferably an alkyl group, an alkoxy group, or a cycloalkoxy group, and even more preferably an alkyl group or a cycloalkoxy group, and these groups may further have a substituent.

[0201] n H1 is preferably 1. H2 is preferably 0.

[0202] 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.

[0203] n H11 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and even more preferably 1.

[0204] RH11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, or a cycloalkyl group, and even more preferably a hydrogen atom or an alkyl group, and these groups may have a substituent.

[0205] L H1 is preferably an arylene group or a divalent heterocyclic group.

[0206] L H1 is preferably a group represented by the above formula (A-1) to formula (A-3), formula (A-8) to formula (A-10), formula (AA-1) to formula (AA-6), formula (AA-10) to formula (AA-21) or formula (AA-24) to formula (AA-34), more preferably a group represented by the above formula (A-1), formula (A-2), formula (A-8), formula (A-9), formula (AA-1) to formula (AA-4), formula (AA-10) to formula (AA-15) or formula (AA-29) to formula (AA-34), and -2), formula (A-8), formula (A-9), formula (AA-2), formula (AA-4), formula (AA-10) to formula (AA-15), more preferably a group represented by the above formula (A-1), formula (A-2), formula (A-8), formula (AA-2), formula (AA-4), formula (AA-10), formula (AA-12) or formula (AA-14), and particularly preferably a group represented by the above formula (A-1), formula (A-2), formula (AA-2), formula (AA-4) or formula (AA-14).

[0207] 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, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and even more preferably an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent.

[0208] L H21is preferably a single bond or an arylene group, more preferably a single bond, and this arylene group may have a substituent.

[0209] L H21 Examples and preferred ranges of the arylene group or divalent heterocyclic group represented by L H1 The examples and preferred ranges of the arylene group or divalent heterocyclic group represented by the following formula are the same as those of the arylene group or divalent heterocyclic group represented by the following formula:

[0210] R H21 is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

[0211] 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:

[0212] R H21 Examples of the substituents that may be substituted by Ar H1 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.

[0213] The compound represented by the above formula (H-1) is preferably a compound represented by the following formula (H-2).

[0214] [ka] [In the formula, Ar H1 , Ar H2 , n H3 and L H1 respectively represent Ar H1 , Ar H2 , n H3 and L H1 It has the same meaning as:

[0215] Specific examples of the low molecular weight host include compounds represented by the following formulas:

[0216] [ka]

[0217] <Polymer host> Examples of the polymer host include polymer compounds that are hole transport materials, which will be described later, and polymer compounds that are electron transport materials, which will be described later.

[0218] A polymer compound preferable as the host material will be described.

[0219] The polymer host is preferably a polymer compound containing a constitutional unit represented by the following formula (Y).

[0220] [ka] [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.]

[0221] 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 the group represented by the formula (A-1), (A-2), (A-7), (A-9) or (A-19) is even more preferred, and these groups may have a substituent.

[0222] 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), (A-33) or (A-34) is more preferred, and the divalent heterocyclic 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.

[0223] Ar Y1 In the divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, more preferred and even more preferred ranges of the arylene group and the divalent heterocyclic group are respectively as defined above for 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:

[0224] Examples of the "divalent group in which an arylene group and a divalent heterocyclic group are directly bonded" include groups represented by the following formulae, which may have a substituent.

[0225] [ka] [In the formula, R XX 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.

[0226] R XX is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0227] Ar Y1 The substituent which the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.

[0228] Examples of the constitutional unit represented by the above formula (Y) include constitutional units represented by the following formulae (Y-1), (Y-2), and (Y-4) to (Y-10).

[0229] [ka] [In the formula, R Y1represents 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.

[0230] R Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0231] [ka] [In the formula, R Y1 is R in the above formula (Y-1) Y1 It means the same as;X Y1 is -C(R Y2 )2-, -C(R Y2 )=C(R Y2 )- or C(R Y2 )2-C(R Y2 )2-represents a group represented by R 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.

[0232] 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.

[0233] X Y1 Regarding -C(R Y2 )2-, where R Y2The 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 The group represented by 2- is preferably a group represented by the following formulae (Y-A1) to (Y-A5), more preferably a group represented by the following formula (Y-A4), and these groups may have a substituent.

[0234] [ka]

[0235] X Y1 Regarding -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.

[0236] X Y1 Regarding -C(R Y2 )2-C(R Y2 )2-, where 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 Y2The group represented by the formula (Y-B1) to (Y-B5) below is preferably a group represented by the formula (Y-B3) below, and these groups may have a substituent.

[0237] [ka] [In the formula, R Y2 is R in the above formula (Y-2) Y2 It has the same meaning as:

[0238] [ka]

[0239] [ka] [In the formula, R Y1 is R in the above formula (Y-1). Y1 It has the same meaning as;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.

[0240] R Y3 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.

[0241] [ka] [In the formula, R Y1 is R in the above formula (Y-1) Y1 It has the same meaning as;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.

[0242] 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.

[0243] Examples of the constitutional unit represented by formula (Y) above include constitutional units composed of arylene groups represented by formulas (Y-101) to (Y-121) below, constitutional units composed of divalent heterocyclic groups represented by formulas (Y-201) to (Y-206) below, and constitutional units composed of divalent groups in which an arylene group and a divalent heterocyclic group are directly bonded to each other represented by formulas (Y-301) to (Y-304) below.

[0244] [ka]

[0245] [ka]

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249] [ka]

[0250] [ka]

[0251] [ka]

[0252] [ka]

[0253] The structural unit represented by the above formula (Y) is Ar 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 the structural units contained in the polymer compound, since the luminance life of a light-emitting device using a composition of a polymer host and the metal complex of this embodiment is excellent.

[0254] The structural unit represented by the above formula (Y) is Ar Y1 The structural unit which is a divalent heterocyclic group or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded to each other provides excellent charge transport properties for a light-emitting device using a composition of a polymer host and the metal complex of this embodiment, and therefore the structural unit is preferably 0.5 to 30 mol %, and more preferably 3 to 20 mol %, relative to the total amount of structural units contained in the polymer compound.

[0255] The polymer host may contain only one type of the structural unit represented by the above formula (Y), or may contain two or more types.

[0256] Since the polymer host has excellent hole transport properties, it is preferable that the polymer host further contains a constitutional unit represented by the following formula (X) in addition to the constitutional unit represented by the above formula (Y).

[0257] [ka] [In the formula, a X1 and a X2 each independently represents an integer of 0 or more; Ar X1 and Ar X3each 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 an arylene group and a divalent heterocyclic group are directly bonded to each other, and these groups may have a substituent; R X1 , R X2 and R X3 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.

[0258] a X1 is preferably 2 or less, and more preferably 1, since the luminance life of a light-emitting device using a composition of a polymer host and the metal complex of this embodiment is excellent.

[0259] a X2 is preferably 2 or less, and more preferably 0, since the luminance life of a light-emitting device using a composition of a polymer host and the metal complex of this embodiment is excellent.

[0260] R X1 , R X2 and R X3 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0261] Ar X1 and Ar X3 The arylene group represented by the formula (A-1) or (A-9) is more preferably a group represented by the formula (A-1) above, and further preferably a group represented by the formula (A-1) above, and these groups may have a substituent.

[0262] Ar X1 and Ar X3 The divalent heterocyclic group represented by the formula (AA-1), (AA-2) or (AA-7) to (AA-26) is more preferred, and these groups may have a substituent.

[0263] Ar X1 and Ar X3 is preferably an arylene group which may have a substituent.

[0264] Ar X2 and Ar X4 The arylene group represented by the formula (A-1), (A-6), (A-7), (A-9) to (A-11) or (A-19) is more preferably a group represented by the formula (A-1), (A-6), (A-7), (A-9) to (A-11) or (A-19), and these groups may have a substituent.

[0265] Ar X2 and Ar X4 A more preferred range of the divalent heterocyclic group represented by Ar X1 and Ar X3 The more preferred range is the same as that of the divalent heterocyclic group represented by the following formula:

[0266] Ar X2 and Ar X4 In the divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, more preferred and even more preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, X1 and Ar X3 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:

[0267] Ar X2 and Ar X4 The divalent group in which an arylene group and a divalent heterocyclic group are directly bonded to each other is represented by the formula (Y): Y1 and a divalent heterocyclic group directly bonded to an arylene group represented by the following formula:

[0268] Ar X2 and Ar X4 is preferably an arylene group which may have a substituent.

[0269] Ar X1 ~Ar X4 and RX1 ~R X3 The substituent which the group represented by the formula (I) may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.

[0270] The constitutional unit represented by the above formula (X) is preferably a constitutional unit represented by the following formulas (X-1) to (X-7).

[0271] [ka]

[0272] [ka]

[0273] [ka]

[0274] [ka] [In the formula, R X4 and R X5 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 halogen atom, a monovalent heterocyclic group, or a cyano group, and these groups may have a substituent; X4 may be the same or different; multiple R X5 may be the same or different, and adjacent R X5 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.

[0275] The structural unit represented by the above 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.

[0276] Examples of the constitutional unit represented by the above formula (X) include constitutional units represented by the following formulas (X1-1) to (X1-17).

[0277] [ka]

[0278] [ka]

[0279] [ka]

[0280] [ka]

[0281] [ka]

[0282] [ka]

[0283] [ka]

[0284] The polymer host may contain only one type of constitutional unit represented by the above formula (X), or may contain two or more types.

[0285] Examples of the polymer host include polymer compounds P-1 to P-7 in Table 1. Here, the "other" structural unit in Table 1 refers to a structural unit represented by the following formula (V) other than the structural unit represented by the above formula (Y) and the structural unit represented by the above formula (X).

[0286] [ka]

[0287] In formula (V), V represents an oxygen atom, a sulfur atom, a methylene group which may have a substituent, -N(R V )-, where R V 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.), or represents a monocyclic or condensed ring arylene group which may have a substituent, and formula (V) does not correspond to formula (Y) or formula (X).

[0288] Examples of the substituent that V in the above formula (V) may have include a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a substituted amino group, and a halogen atom.

[0289] [Table 1]

[0290] In Table 1, 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. The other structural units refer to structural units represented by the above formula (V) other than the structural units represented by the above formula (Y) and the structural units represented by the above formula (X).

[0291] 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.

[0292] 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.

[0293] In the 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 at once, a method in which a part of the monomers is fed and reacted, and then the remaining monomers are fed at once, continuously or in portions, and a method in which the monomers are fed continuously or in portions.

[0294] Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst.

[0295] The post-treatment of the polymerization reaction can be carried out by any of known methods, such as 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, either alone or in combination. When the purity of the polymer host is low, it can be purified by a conventional method such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

[0296] [Hole transport material] The hole transport material is classified into a low molecular weight compound and a polymeric compound, with the polymeric compound being preferred, and a polymeric compound having a crosslinking group being more preferred.

[0297] Examples of the polymer compound constituting the hole transport material include polyvinylcarbazole and its derivatives; polyarylene and its derivatives having an aromatic amine structure in the side chain or main chain. The polymer compound constituting the hole transport material may be a polymer compound containing a structural unit represented by the above formula (Y) and optionally a structural unit represented by the above formula (X), and preferably the polymer compound further has a structural unit having a crosslinking group. Examples of the structural unit having a crosslinking group include those in which the arylene group or divalent heterocyclic group in the structural unit represented by the above formula (Y) has a crosslinking group. The polymer compound constituting the hole transport material may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, and preferably fullerene.

[0298] When the composition of this embodiment contains a hole transport material, the amount of the hole transport 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 of this embodiment.

[0299] The hole transport material may be used alone or in combination of two or more kinds.

[0300] [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.

[0301] Examples of low molecular weight compounds that constitute the electron transport material include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, diphenoquinone, and derivatives thereof.

[0302] Examples of the polymer compound constituting the electron transport material include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal. The polymer compound constituting the electron transport material may be a polymer compound containing a structural unit represented by the above formula (Y), and the polymer compound may further have a structural unit having a crosslinking group. Examples of the structural unit having a crosslinking group include those in which the arylene group or divalent heterocyclic group in the structural unit represented by the above formula (Y) has a crosslinking group.

[0303] When the composition of this embodiment contains an electron transport material, the amount of the electron transport 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 of this embodiment.

[0304] The electron transporting materials may be used alone or in combination of two or more kinds.

[0305] [Hole injection material and electron injection material] 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.

[0306] Examples of low molecular weight compounds constituting the hole injection material and the electron injection material 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.

[0307] Examples of the polymer compounds constituting the hole injection material and the electron injection material include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, polyquinoxaline, and derivatives thereof; and conductive polymers such as polymers containing a group represented by the above formula (X) in the main chain or side chain.

[0308] When the composition of the present embodiment contains a hole injection material and / or an electron injection material, the amount of the hole injection material and the electron injection material is usually 1 part by mass to 400 parts by mass, and preferably 5 parts by mass to 150 parts by mass, per 100 parts by mass of the metal complex of the present embodiment.

[0309] The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.

[0310] [Ion doping] When the hole injection material and / or the electron injection material includes a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1×10 -5 S / cm~1×10 3 In order to set the electrical conductivity of the conductive polymer in this range, the conductive polymer can be doped with an appropriate amount of ions.

[0311] The type of ion to be doped is an anion for a hole injection material, and a cation for an electron injection material. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

[0312] The doping ions may be of one type or two or more types.

[0313] [Luminescent materials] The luminescent material (different from the metal complex of the present embodiment) is classified into a low molecular weight compound and a high molecular weight compound. The luminescent material may have a crosslinking group.

[0314] Examples of low molecular weight compounds constituting the light emitting material include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triplet light emitting complexes having iridium, platinum, or europium as a central metal.

[0315] Examples of the polymer compound constituting the light-emitting material include polymer compounds containing a phenylene group, a naphthalenediyl group, an anthracenediyl group, a fluorenediyldiyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a group represented by the above formula (X), a carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, and / or a pyrenediyl group.

[0316] The light-emitting material may include low molecular weight compounds and high molecular weight compounds, and preferably includes triplet light-emitting complexes and high molecular weight compounds.

[0317] Examples of triplet light-emitting complexes include the metal complexes shown below.

[0318] [ka]

[0319] [ka]

[0320] When the composition of this embodiment contains a light emitting material, the content of the light emitting material is usually 0.1 parts by mass to 400 parts by mass with respect to 100 parts by mass of the metal complex of this embodiment.

[0321] [solvent] The composition containing the metal complex of this embodiment and a solvent (hereinafter, sometimes referred to as "ink") is suitable for producing a light-emitting device using a printing method such as inkjet printing or nozzle printing.

[0322] The viscosity of the ink may 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 to prevent clogging and deflection during discharge.

[0323] 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 tetrahydrofuran, dioxane, anisole, and 4-methylanisole; aromatic hydrocarbon-based solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; and fatty solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-decane, and bicyclohexyl. Examples of the solvent include aromatic hydrocarbon solvents, 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.

[0324] The amount of the solvent in the ink is usually 1,000 parts by mass to 100,000 parts by mass, and preferably 2,000 parts by mass to 20,000 parts by mass, per 100 parts by mass of the metal complex of this embodiment.

[0325] The antioxidant may be any compound that does not inhibit light emission and charge transport, and examples of the antioxidant include phenol-based antioxidants and phosphorus-based antioxidants. When the composition contains a solvent, the antioxidant is preferably soluble in the solvent.

[0326] When the composition of the present embodiment contains an antioxidant, the amount of the antioxidant is usually 0.0001 parts by mass to 10 parts by mass with respect to 100 parts by mass of the metal complex of the present embodiment.

[0327] The antioxidants may be used alone or in combination of two or more kinds.

[0328] <Membrane> The film contains the metal complex of this embodiment. The film also includes an insolubilized film obtained by insolubilizing the metal complex of the present embodiment in a solvent through crosslinking. The insolubilized film is a film obtained by crosslinking the metal complex of the present embodiment through an external stimulus such as heating (the temperature is usually 25 to 300° C.) and / or light irradiation (the light is, for example, ultraviolet light, near-ultraviolet light, or visible light). Since the insolubilized film is substantially insoluble in a solvent, it can be suitably used for laminating light-emitting elements. The film is suitable as a hole transport layer or a hole injection layer in a light emitting device.

[0329] 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.

[0330] The thickness of the film is usually from 1 nm to 10 μm.

[0331] <Light emitting element> The light-emitting device of this embodiment is a light-emitting device containing the metal complex of this embodiment. The light-emitting device of this embodiment may have, for example, a configuration including electrodes composed of an anode and a cathode, and a layer containing the metal complex of this embodiment provided between the electrodes.

[0332] [Layer composition] The layers constituting the light-emitting device of this embodiment are usually one or more layers selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer. At least one of the layers constituting the light-emitting device of this embodiment contains the metal complex of this embodiment, and preferably the light-emitting layer contains the metal complex of this embodiment.

[0333] The light-emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, and the electron injection layer can be formed by the same method as the preparation of the above-mentioned film, using an ink prepared by dissolving the material constituting the layer in the above-mentioned solvent. The materials of the light-emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, and the electron injection layer include the above-mentioned host material, a light-emitting material different from the metal complex of the present embodiment, a hole transport material, a hole injection material, an electron transport material, and an electron injection material, in addition to the metal complex of the present embodiment. The light-emitting layer can contain, for example, the metal complex of the present embodiment and the host material, and can further contain a light-emitting material different from the metal complex of the present embodiment. In addition, the hole transport layer, the hole injection layer, the electron transport layer, and the electron injection layer can contain a hole transport material, a hole injection material, an electron transport material, and an electron injection material, respectively.

[0334] The light-emitting element has a light-emitting layer between an anode and a cathode. From the viewpoint of hole injection and hole transport properties, the light-emitting element of 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.

[0335] When the material of the hole transport layer, the material of the electron transport layer and the material of the light emitting layer are soluble in a solvent used for forming the hole transport layer, the electron transport layer and the layer adjacent to the light emitting layer in the preparation of the light emitting device, the material preferably has a crosslinking group in order to prevent the material from dissolving in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

[0336] In the light-emitting element of this embodiment, examples of methods for forming each layer, such as the light-emitting layer, hole transport layer, electron transport layer, hole injection layer, and 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, and when a high molecular weight compound is used, for example, a method of film formation from a solution or molten state.

[0337] The order, number and thickness of the layers to be stacked may be adjusted taking into consideration, for example, the external quantum efficiency and the device life.

[0338] [Substrate / electrode] The substrate in the light-emitting element may be any substrate on which the electrodes can be formed and which is not chemically changed when the organic layers are formed, and may be made of materials such as glass, plastic, silicon, etc. In the case of an opaque substrate, it is preferable that the electrode furthest from the substrate is transparent or semi-transparent.

[0339] Anode materials include, for example, conductive metal oxides, translucent metals, and preferably indium oxide, zinc oxide, and tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; silver palladium copper composite (APC); and NESA, gold, platinum, silver, and copper.

[0340] Examples of the cathode material include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium, and alloys of two or more of these metals; alloys of one or more of lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.

[0341] The anode and the cathode may each have a laminated structure of two or more layers.

[0342] [Application] The light-emitting element of this embodiment is useful for, for example, displays and lighting.

[0343] Although the preferred embodiments of the present invention have been described above, the present invention is not limited to the above-described embodiments. EXAMPLES

[0344] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0345] 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).

[0346] 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).

[0347] 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).

[0348] Example 1 Synthesis of metal complex M1

[0349] [ka]

[0350] [ka]

[0351] (Synthesis of compound L1F) Compound L1F was synthesized according to the method described in International Publication No. 2019 / 017697.

[0352] (Stage 1: Synthesis of compound L1B) After the inside of the reaction vessel was filled with nitrogen, compound L1A (12.2 g) and tetrahydrofuran (600 g) were added and cooled to -70°C. 1.6M n-butyllithium n-hexane solution (18 mL) was slowly added thereto and stirred at -70°C for 1 hour. Pinacol isopropoxyboronate (7.2 g) was slowly added thereto and then stirred at -65°C for 1 hour. After the obtained reaction solution was brought to room temperature, ion-exchanged water (180 g) and toluene (180 g) were slowly added and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, dried over magnesium sulfate, and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was crystallized using toluene and acetonitrile, and then dried under reduced pressure at 50°C to obtain compound L1B (8.9 g). The LC area percentage value of compound L1B was 99.4%.

[0353] (Stage 2: Synthesis of compound L1D) After the inside of the reaction vessel was filled with nitrogen, compound L1B (8.0 g), compound L1C (8.7 g), tetrakis(triphenylphosphine)palladium(0) (1.8 g), 20% by mass tetraethylammonium hydroxide aqueous solution (50.9 g), ion-exchanged water (50.9 mL), ethanol (80 ml) and toluene (400 mL) were added and stirred at 50 ° C for 1 hour. The obtained reaction solution was cooled to room temperature, 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 ethanol, and dried under reduced pressure at 50 ° C to obtain compound L1D (7.1 g). The HPLC area percentage value of compound L1D was 99.2%. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=7.94-7.93(m, 3H),7.82-7.75(m, 2H),7.52(dd, 1H) ,7.42(td, 2H),7.15(td, 2H),7.03(s, 1H),6.83(d, 1H),6.69(d, 2H),1.23(s, 12H).

[0354] (Stage 3: Synthesis of compound L1E) After the inside of the reaction vessel was filled with nitrogen, compound L1D (6.5 g), bis(pinacolato)diboron (2.7 g), dimethoxyethane (130 mL), toluene (130 ml), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride·dichloromethane adduct (359 mg), and potassium acetate (1.7 g) were added and stirred at 80°C for 9 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 then stirred at room temperature for 30 minutes, filtered through a filter lined with Celite, the filtrate was concentrated under reduced pressure, washed with toluene and acetonitrile, and dried at 50°C under reduced pressure to obtain compound L1E (6.6 g) as a white solid. The HPLC area percentage value of compound L1E was 99.5% or more. 1 H-NMR (400MHz, CD2Cl2) δ (ppm) = 8.91 (dd, 1H), 8.54 (d, 4H), 8.08 (d, 1H), 8.03 (d, 1H), 7,97 (d, 2H), 7.86(d, 1H),7.60-7.52(m, 5H),7.46(t, 2H),7.18(t, 2H),6.86(d, 1H),6.79(d, 2H),1.38(s, 18H).

[0355] (Stage 4: Synthesis of compound L1G) After the inside of the reaction vessel was filled with nitrogen, compound L1E (6.0 g), compound L1F (2.6 g), tetrakis(triphenylphosphine)palladium(0) (882 mg), 20% by mass tetraethylammonium hydroxide aqueous solution (44.6 g), ion-exchanged water (44.6 mL), and toluene (480 mL) were added and stirred at 95 ° C. for 5 hours. After the obtained reaction liquid was cooled to room temperature, ion-exchanged water (120 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 ethanol, and dried under reduced pressure at 50 ° C. to obtain compound L1G (7.0 g). The HPLC area percentage value of compound L1G was 99.5% or more. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=8.91(d,1H),8.54(d,4H),8.13(d,1H),8.05-7.96(m,4H),7.85(d ,1H),7.56(d,4H),7.46(t,2H),7.17(t,2H),7.05(s,1H),6.76(d,2H),1.38(s,18),1.25(s,12H).

[0356] (Stage 5: Synthesis of compound L1) After the inside of the reaction vessel was filled with nitrogen, compound L1G (6.8 g), compound L1H (3.0 g), tris(dibenzylideneacetone)dipalladium(0) (98.5 mg), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (150.0 mg), 40% by mass tetrabutylammonium hydroxide aqueous solution (14.1 g), ion-exchanged water (14.1 mL), and toluene (136 mL) were added and stirred at 80 ° C. for 1 hour. 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 ethanol, and dried under reduced pressure at 50 ° C. to obtain compound L1 (8.3 g). The HPLC area percentage value of compound L1 was 99.5% or more. 1H-NMR (400MHz, CD2Cl2)δ(ppm)=8.94(dd, 1H), 8.55(dd, 4H), 8.35(dd, 4H), 8.1 8-8.13(m, 3H), 8.11(s, 1H), 8.06-8.02(m, 3H), 7.72(s, 1H), 7.70-7.63(m, 2H), 7.57(d, 4H), 7.51-7.45(m, 3H), 7.38-7.27(m, 2H), 7.26-7.10(m, 8H), 6.87(d, 2) H), 2.69(t, 4H), 1.69(quin, 4H), 1.58(s, 6H), 1.46-1.30(m, 30H), 0.90(t, 6H).

[0357] (Stage 6: Synthesis of metal complex M1a) After the inside of the light-shielded reaction vessel was filled with argon gas, iridium(III) chloride hydrate (390 mg), compound L1 (2.80 g) and 2-ethoxyethanol (12 mL) were added and stirred at 140° C. for 24 hours. The resulting reaction product was cooled to room temperature, then added to methanol (20 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 red solid (1.98 g) containing the metal complex M1a.

[0358] (Stage 7: 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 (1.98 g), compound L1 (946.5 mg), silver(I) trifluoromethanesulfonate (272.4 mg), 2,6-lutidine (124 μL) and diethylene glycol dimethyl ether (20 mL) were added and stirred at 157° C. for 72 hours. The resulting reaction product was cooled to room temperature, then added to methanol (60 mL) and stirred at room temperature for 1 hour, then filtered, toluene (50 mL) was added to the resulting residue, and the mixture was filtered through a filter covered with Celite, and the resulting filtrate was concentrated under reduced pressure to obtain a solid. The resulting solid was purified by silica gel column chromatography (toluene / hexane) and crystallization (toluene / ethanol), followed by drying under reduced pressure to obtain metal complex M1 (705 mg, 24% yield based on the amount of IrCl3·3H2O charged when iridium(III) chloride hydrate was treated as a trihydrate) as a red solid. The HPLC area percentage value of metal complex M1 was 99.4%. LC-MS(APCI positive):m / z=3632.9[M] + 1 H-NMR (400MHz, CD2Cl2) δ (ppm) = 8.85-8.78 (m, 6H), 8.53 (d, 12H), 8.20 (s, 3H), 8 .09(s, 3H), 8.02-7.95(m, 6H), 7.91(s, 3H), 7.72-7.63(m, 6H), 7.62-7.45(m, 21 H), 7.41(t, 3H), 7.30-7.11(m, 21H), 7.09(t, 3H), 7.02(d, 3H), 6.86(d, 3H), 2.6 6(t, 12H), 1.65(t, 12H), 1.45(m, 90H), 0.85(s, 18H), 0.51(s, 9H), 0.16(s, 9H).

[0359] Example 2 Synthesis of metal complex M2

[0360] [ka]

[0361] [ka]

[0362] (Stage 1: Synthesis of compound L2B) After the inside of the reaction vessel was filled with nitrogen, compound L2A (13.9 g), compound L1F (9.0 g), tetrakis(triphenylphosphine)palladium(0) (3.3 g), 20% by mass tetraethylammonium hydroxide aqueous solution (84.2 g), and toluene (180 mL) were added and stirred at 65 ° C for 2 hours. After the obtained reaction liquid was cooled to room temperature, the solid was filtered and washed with ion-exchanged water, ethanol, and toluene. The obtained solid was dissolved in chloroform, filtered with a filter covered with celite and silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained crude product was crystallized with toluene and ethanol, and dried under reduced pressure at 50 ° C to obtain compound L2B (14.1 g). The HPLC area percentage value of compound L2B was 99.5% or more.

[0363] (Stage 2: Synthesis of compound L2) After the inside of the reaction vessel was filled with nitrogen, compound L2B (13.0 g), compound L1H (8.96 g), tris(dibenzylideneacetone)dipalladium(0) (307 mg), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (453 mg), 40% by mass tetrabutylammonium hydroxide aqueous solution (42.7 g), ion-exchanged water (42.7 mL), and toluene (260 mL) were added and stirred at 60 ° C for 4 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 ethanol, and dried under reduced pressure at 50 ° C to obtain compound L2 (15.6 g). The HPLC area percentage value of compound L2 was 99.5% or more. 1H-NMR (400MHz, CDCl3)δ(ppm)=8.33(dd, 1H), 8.12(s, 1H), 8.09(s, 1H), 8. 01(d, 1H), 7.93-7.85(m, 3H), 7.65(d, 1H), 7.58(s, 1H), 7.53(d, 1H), 7.45 (d, 1H), 7.42-7.26(m, 5H), 7.16-7.08(m, 6H), 6.79(d, 2H), 6.72(d, 1H), 2 .67(t, 4H), 1.67(quin, 4H), 1.58(s, 6H), 1.44-1.26(m, 12H), 0.89(t, 6H).

[0364] (Stage 3: Synthesis of metal complex M2a) After the inside of the light-shielded reaction vessel was filled with argon gas, iridium(III) chloride hydrate (1.5 g), compound L2 (7.2 g) and 2-ethoxyethanol (45 mL) were added and stirred at 130° C. for 24 hours. The resulting reaction product was cooled to room temperature, then added to methanol (75 g) and stirred at room temperature for 1 hour, followed by filtration, and the resulting residue was dried under reduced pressure to obtain a red solid (7.5 g) containing the metal complex M2a.

[0365] (Stage 4: Synthesis of metal complex M2) After the inside of a light-shielded reaction vessel was filled with an argon gas atmosphere, a red solid containing metal complex M2a (7.40 g), compound L2 (3.41 g), silver(I) trifluoromethanesulfonate (1.40 g), 2,6-lutidine (628 μL) and diethylene glycol dimethyl ether (74 mL) were added and stirred at 150° C. for 72 hours. The resulting reaction product was cooled to room temperature, then added to methanol (100 mL) and stirred at room temperature for 1 hour. Then, filtration was performed, toluene (120 mL) was added to the resulting residue, and the mixture was filtered through a filter covered with Celite. The 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) in that order, and then dried under reduced pressure to obtain metal complex M2 (3.0, 29% yield based on the amount of IrCl3·3H2O charged when iridium(III) chloride hydrate was treated as a trihydrate) as a red solid. The HPLC area percentage value of metal complex M2 was 99.5% or more. 1H-NMR (400MHz, CD2Cl2) δ (ppm) = 8.76 (s, 3H), 8.16 (s, 3H), 7.93-7.84 (m, 9H), 7.58 (d, 3H), 7.50-7.42 (m, 6H), 7.39-7.29 (m, 6H), 7.28-7.08 (m, 24H), 7.06-6.97(m, 12H), 6.74(d, 3H), 6.54(d, 3H), 2.64(t, 12H), 1.63( quin, 12H), 1.40-1.20(m, 36H), 0.88(t, 18H), 0.48(s, 9H), 0.13(s, 9H).

[0366] <Comparative Examples 1 and 2> Obtaining metal complexes CM1 and CM2 Metal complexes CM1 and CM2 used were manufactured by Luminescense Technology.

[0367] [ka]

[0368] Comparative Example 3 Synthesis of metal complex CM3

[0369] [ka]

[0370] [ka]

[0371] (Stage 1: Synthesis of compound CL3B) After the inside of the reaction vessel was filled with nitrogen, compound CL3A (6.4 g), compound L1F (9.0 g), tetrakis(triphenylphosphine)palladium(0) (3.3 g), 20% by mass tetraethylammonium hydroxide aqueous solution (48.2 g), ion-exchanged water (36 g), and toluene (180 g) were added and stirred at 70° C. for 3 hours. The obtained reaction solution was cooled to room temperature, and then ion-exchanged water (90 g) was 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 dissolved in toluene, filtered with a filter covered with silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was crystallized with toluene and ethanol, and dried under reduced pressure at 50° C. to obtain compound CL3B (8.2 g). The HPLC area percentage value of compound CL3B was 99.3%. This process was repeated until the required amount of compound CL3B was obtained.

[0372] (Stage 2: Synthesis of compound CL3) After the inside of the reaction vessel was filled with nitrogen, compound CL3B (8.8 g), compound L1H (10.1 g), tris(dibenzylideneacetone)dipalladium(0) (347 mg), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (512 mg), 40% by mass tetrabutylammonium hydroxide aqueous solution (48.1 g), ion-exchanged water (48.1 g), and toluene (88.0 g) were added and stirred at 70°C for 2 hours. The reaction solution obtained was cooled to room temperature, and then ion-exchanged water (88.0 g) was added and the water layer was removed. The organic layer obtained was washed with ion-exchanged water, filtered, and the filtrate obtained was concentrated under reduced pressure to obtain a crude product. The crude product obtained was purified by silica gel column chromatography (toluene / hexane) and dried under reduced pressure at 50°C to obtain compound CL3 (12.6 g). The HPLC area percentage value of compound CL3 was 99.3% or more. 1H-NMR (400MHz, CDCl3)δ(ppm)=8.26-8.20(m, 4H), 7.81(s, 1H), 7.71(d, 1H), 7.56-7.44(m, 4H), 7.39-7.30(m, 2 H), 7.30-7.35(m, 2H), 7.18(s, 1H), 2.72(t, 4H), 1.73(quin, 4H), 1.63(s, 6H), 1.49-1.25(m, 12H), 0.90(t, 6H).

[0373] (Stage 3: Synthesis of metal complex CM3a) After the inside of a light-shielded reaction vessel was filled with an argon gas atmosphere, iridium(III) chloride hydrate (1.46 g), compound CL3 (5.19 g) and 2-ethoxyethanol (44 mL) were added and stirred at 140° C. for 24 hours. The reaction mixture was cooled to room temperature, added to methanol (73 mL), and stirred at room temperature for 1 hour. Then, the mixture was filtered, and the residue was dried under reduced pressure to obtain a red solid (3.67 g) containing the metal complex CM3a.

[0374] (Stage 4: Synthesis of metal complex CM3) After the inside of a light-shielded reaction vessel was filled with an argon gas atmosphere, a red solid containing metal complex CM3a (1.98 g), compound CL3 (946.5 mg), silver(I) trifluoromethanesulfonate (272.4 mg), 2,6-lutidine (124 μL) and diethylene glycol dimethyl ether (20 mL) were added and stirred at 150° C. for 48 hours. The resulting reaction product was cooled to room temperature, then added to methanol (60 mL) and stirred at room temperature for 1 hour, then filtered, toluene (50 mL) was added to the resulting residue, and the mixture was 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) in that order, and then dried under reduced pressure to obtain the metal complex CM3 (1.15 g, 16% yield based on the amount of IrCl3·3H2O charged when iridium(III) chloride hydrate was treated as a trihydrate) as a red solid. The HPLC area percentage value of the metal complex CM3 was 99.0%. 1 H-NMR (400MHz, CD2Cl2)δ(ppm)=8.75(s, 3H), 8.27(s, 3H), 8.17(s, 3H), 7.89(d, 3H), 7.63(d, 3H), 7.30-7.13(m, 15H), 7.07(d, 3H), 6.89(t, 3H), 6.72(t, 3H), 6.52(d, 3H), 2.74(t, 12H), 1.72(quin, 12H), 1.46-1.22(m, 36H), 0.88(t, 18H), 0.53(s, 9H), 0.22(s, 9H).

[0375] <Synthesis Example 1> Synthesis of polymer compound IP1 Polymer compound IP1 was synthesized by the method described in JP 2012-144722 A using monomer PM1 synthesized according to the method described in JP 2011-174062 A, monomer PM2 synthesized according to the method described in WO 2005 / 049546 A, monomer PM3 synthesized according to the method described in WO 2002 / 045184 A, and monomer PM4 synthesized according to the method described in JP 2008-106241 A.

[0376] [ka]

[0377] The polymer compound IP1 is a copolymer composed of structural units derived from monomer PM1, structural units derived from monomer PM2, structural units derived from monomer PM3, and structural units derived from monomer PM4 in a molar ratio of 50:30:12.5:7.5, according to the theoretical value calculated from the amounts of the charged raw materials.

[0378] <Synthesis Example 2> Synthesis of polymer compound P1 Polymer compound P1 was synthesized by the method described in WO 2012 / 133381 using the above-mentioned monomer PM3, monomer PM5 synthesized according to the method described in WO 2005 / 056633, and monomer PM6 synthesized according to the method described in WO 2011 / 078391.

[0379] [ka]

[0380] Polymer compound P1 is a copolymer composed of structural units derived from monomer PM3, structural units derived from monomer PM5, and structural units derived from monomer PM6 in a molar ratio of 50:5:45, according to the theoretical value calculated from the amounts of the charged raw materials.

[0381] Example D1 <Fabrication of Light-Emitting Element D1> (Formation of anode and hole injection layer) An ITO film was attached to a glass substrate by sputtering to a thickness of 45 nm to form an anode. A hole injection material ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) was formed on the anode by spin coating to a thickness of 65 nm. The substrate on which the hole injection layer was laminated was heated on a hot plate at 50°C for 3 minutes in an air atmosphere, and further heated at 240°C for 15 minutes to form a hole injection layer.

[0382] (Formation of Hole Transport Layer) Polymer compound IP1, which is a hole transport material, was dissolved in xylene as a solvent at a concentration of 0.6% by mass. The resulting xylene solution was used to form a film with a thickness of 20 nm on the hole injection layer by spin coating, and the film was heated on a hot plate at 180°C for 60 minutes in a nitrogen gas atmosphere to form a hole transport layer.

[0383] (Formation of the light-emitting layer) A polymer compound P1 and a metal complex M1 (P1 / M1=92% by mass / 8% by mass), which are host materials, were dissolved in a xylene solvent at a concentration of 2% by mass. The resulting xylene solution was used to form a film with a thickness of 90 nm on the hole transport layer by spin coating, and the film was heated at 150° C. for 10 minutes in a nitrogen gas atmosphere to form an emitting layer.

[0384] (Cathode formation) The substrate on which the light-emitting layer was formed was placed in the deposition chamber and 1.0×10 -4 After reducing the pressure to below 1 Pa, sodium fluoride was deposited on the light-emitting layer to a thickness of about 4 nm, and then aluminum was deposited on the sodium fluoride layer to a thickness of about 80 nm to form a cathode. After deposition, the device was sealed using a glass substrate to produce light-emitting device D1.

[0385] Evaluation of Light-emitting Device D1 By applying a voltage to the light-emitting element D1, light emission having a maximum peak in the emission spectrum at 625 nm was observed. CIE chromaticity coordinates (x, y)=(0.67, 0.33), 1000 cd / m 2 The external quantum efficiency was 12.6% at a current density of 50 mA / cm 2 After setting the current value so that the LED was driven at a constant current density, the change in luminance over time was measured to evaluate the luminance life. It took 128 hours for the luminance to reach 80% of the initial luminance. The results are shown in Table 2 below.

[0386] Example D2 <Fabrication and Evaluation of Light-Emitting Device D2> A light-emitting device D2 was produced in the same manner as in Example D1, except that metal complex M2 was used instead of metal complex M1. By applying a voltage to the light-emitting element D2, light emission having a maximum peak in the emission spectrum at 610 nm was observed. CIE chromaticity coordinates (x, y) = (0.65, 0.35), 1000 cd / m 2 The external quantum efficiency was 15% at a current density of 50 mA / cm 2After setting the current value so that the LED was driven at a constant current density, the change in luminance over time was measured to evaluate the luminance life. It took 24 hours for the luminance to reach 80% of the initial luminance. The results are shown in Table 2 below.

[0387] <Comparative Example CD1> <Fabrication and Evaluation of Light-Emitting Device CD1> A light-emitting element CD1 was produced in the same manner as in Example D1, except that metal complex CM1 was used instead of metal complex M1. By applying a voltage to the light-emitting element CD1, light emission having a maximum peak in the emission spectrum at 590 nm was observed. CIE chromaticity coordinates (x, y) = (0.57, 0.42), 1000 cd / m 2 The external quantum efficiency was 5.4% at a current density of 50 mA / cm 2 After setting the current value so that the LED was driven at a constant current density, the change in luminance over time was measured to evaluate the luminance life. It took 3 hours for the luminance to reach 80% of the initial luminance. The results are shown in Table 2 below.

[0388] <Comparative Example CD2> <Fabrication and Evaluation of Light-Emitting Device CD2> A light-emitting device CD2 was produced in the same manner as in Example D1, except that metal complex CM2 was used instead of metal complex M1 in Example D1. By applying a voltage to the light-emitting element CD2, light emission having a maximum peak in the emission spectrum at 620 nm was observed. CIE chromaticity coordinates (x, y) = (0.67, 0.33), 1000 cd / m 2 The external quantum efficiency was 3.8% at a current density of 50 mA / cm 2 After setting the current value so that the LED was driven at a constant current density, the change in luminance over time was measured to evaluate the luminance life. It took 7 hours for the luminance to reach 80% of the initial luminance. The results are shown in Table 2 below.

[0389] <Comparative Example CD3> <Fabrication and Evaluation of Light-Emitting Device CD3> A light-emitting device CD3 was produced in the same manner as in Example D1, except that metal complex CM3 was used instead of metal complex M1 in Example D1. By applying a voltage to the light-emitting element CD3, light emission was observed with a maximum peak in the emission spectrum at 600 nm. CIE chromaticity coordinates (x, y) = (0.61, 0.39), 1000 cd / m 2 The external quantum efficiency was 9.3% at a current density of 50 mA / cm 2 After setting the current value so that the LED was driven at a constant current density, the change in luminance over time was measured to evaluate the luminance life. It took 13 hours for the luminance to reach 80% of the initial luminance. The results are shown in Table 2 below.

[0390] [Table 2] [Industrial Applicability]

[0391] According to the present invention, it is possible to provide a metal complex useful for producing a light-emitting device exhibiting an improved luminance life. In addition, 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 the following formula (00): 【Chemistry 1】 [In the formula, M represents an iridium atom; n １ represents 3; Subscript n １ Each of the ligands, the number of which is defined by, may be the same or different; Subscript n １ each ligand whose number is defined by the formula (I) has a spirobifluorene structure, in which a ring R C1 , a ring R C2 , X a and X b together form the spirobifluorene structure, one of X a and X b is a single bond, the ring R C1 and the ring R C2 together with the single bond X a or X b form one fluorene structure constituting the spirobifluorene structure, and the non-single bond X a or X b forms the other fluorene structure constituting the spirobifluorene structure, the spirobifluorene structure may have a substituent, and when a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which each is bonded; Subscript n １ In each ligand, the number of which is defined by E １ , E ２ , E ３ , E ４ , E ５ , and E ６ each independently represents a nitrogen atom or a carbon atom, １ and E. ２ , E ２ and E. ３ , E ３ and E. ４ , E ４ and E. ５ , or E ５ and E. ６ is a carbon atom; １ When is a nitrogen atom, R １ does not exist; E ２ When is a nitrogen atom, R ２ does not exist; E ３ When is a nitrogen atom, R ３ does not exist; E ４ When is a nitrogen atom, R ４ does not exist; E ５ When is a nitrogen atom, R ５ does not exist; E ６ When is a nitrogen atom, R ６ does not exist; Subscript n １ In each ligand, the number of which is defined by R １ and R ２ , R ２ and R ３ , and R ３ and R4 are combined together to form a group represented by the following formula (P); R that does not form a group represented by the following formula (P) １ , R ２ , R ３ , R ４ , and R ６ 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, these groups may have a substituent, and when a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which they are bonded, and R 5 is an aryl group having two alkyl groups; Here, the "substituent" represents 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, and the substituent may be a bridging group.] 【Chemistry 2】 [In the formula, The dotted line is E １ , E ２ , E ３ , E ４ , E ５ , or E ６ Showing the bond with; Ring R Ｃ３ represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent, and when a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which each of them is bonded; Y ａ and Y ｂ One of them is a single bond, and the other is -C(R Ｙａ ) ２ -, and R Ｙａ 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. When a plurality of substituents are present, they may be bonded to each other to form a ring together with the atom to which each is bonded; Ｙａ may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded. Here, the "substituent" represents 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, and the substituent may be a bridging group.

2. In the formula (00), the subscript n １ In each ligand, the number of which is defined by R ２ and R ３ and (B) are combined together to form a group represented by formula (P).

3. The metal complex according to claim 1 or 2, wherein the formula (P) is represented by the following formula (P'): 【Chemistry 3】 [In the formula, The dotted line is E １ , E ２ , E ３ , E ４ , E ５ , or E ６ Showing the bond with; Y ａ and Y ｂ respectively represent Y in the formula (P). ａ and Y ｂ It means the same thing as; R Ｃ３１ , R Ｃ３２ , R Ｃ３３ and R Ｃ３４ 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; R Ｃ３１ and R Ｃ３２ , R Ｃ３２ and R Ｃ３３ , and R Ｃ３３ and R Ｃ３４ may be bonded to each other to form a ring together with the atoms to which they are bonded.

4. The metal complex according to claim 3, wherein the metal complex represented by the formula (00) is a metal complex represented by the following formula (2-A10), the following formula (2-B10), or the following formula (2-C10): 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 [In formulas (2-A10), (2-B10), and (2-C10), X a and X b and the two benzene rings adjacent thereto together form the spirobifluorene structure; M, n １ , X ａ , X ｂ , E １ , E ４ , E ５ , E ６ , R １ , R ４ , R ５ , and R6 are respectively M, n １ , X ａ , X ｂ , E １ , E ４ , E ５ , E ６ , R １ , R ４ , R ５ and R6 have the same meaning; Y ａ and Y ｂ respectively represent Y in the formula (P). ａ and Y ｂ It has the same meaning as R Ｃ３１ , R Ｃ３２ , R Ｃ３３ , and R Ｃ３４ are R in the formula (P'), Ｃ３１ , R Ｃ３２ , R Ｃ３３ , and R Ｃ３４ It means the same thing as; R in formula (2-A10) Ｃ１１ and R Ｃ１４ , R in formula (2-B10) Ｃ１３ and R Ｃ１４ and R in formula (2-C10) Ｃ１１ and R Ｃ１２ 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; R Ｃ２１ , R Ｃ２２ , R Ｃ２３ and R Ｃ２４ 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; the subscript n １ In each ligand, the number of which is defined by R Ｃ１１ and R Ｃ１２ , R Ｃ１３ and R Ｃ１４ , R Ｃ２１ and R Ｃ２２ , R Ｃ２２ and R Ｃ２３ , and R Ｃ２３ and R Ｃ２４ may be bonded to each other to form a ring together with the atoms to which they are bonded.

5. The metal complex according to claim 4, wherein the metal complex represented by the formula (2-A10) is a metal complex represented by the following formula (2-A1-10): 【Chemistry 7】 [In the formula, M, n １ , E １ , E ４ , E ５ , E ６ , R １ , R ４ , R ５ , and R6 are respectively M, n １ , E １ , E ４ , E ５ , E ６ , R １ , R ４ , R ５ and R6 have the same meaning; Y ａ and Y ｂ respectively represent Y in the formula (P). ａ and Y ｂ It has the same meaning as R Ｃ３１ , R Ｃ３２ , R Ｃ３３ , and R Ｃ３４ are R in the formula (P'), Ｃ３１ , R Ｃ３２ , R Ｃ３３ , and R Ｃ３４ It has the same meaning as R Ｃ１１ , R Ｃ１４ , R Ｃ２１ , R Ｃ２２ , R Ｃ２３ , and R Ｃ２４ are R in the above formula (2-A1), Ｃ１１ , R Ｃ１４ , R Ｃ２１ , R Ｃ２２ , R Ｃ２３ , and R Ｃ２４ It means the same thing as; R Ｃ４１ , R Ｃ４２ , R Ｃ４３ , R Ｃ４４ , R Ｃ４５ , R Ｃ４６ , R Ｃ４７ and R Ｃ４８ 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; the subscript n １ In each or one of the ligands, the number of which is defined by Ｃ４１ and R Ｃ４２ , R Ｃ４２ and R Ｃ４３ , R Ｃ４３ and R Ｃ４４ , R Ｃ４５ and R Ｃ４６ , R Ｃ４６ and R Ｃ４７ , and R Ｃ４７ and R Ｃ４８ may be bonded to each other to form a ring together with the atoms to which they are bonded.

6. The ring R Ｃ１ , the ring R Ｃ２ Or the ring R Ｃ３ has a group represented by the following formula (DA), the following formula (DB), or the following formula (DC) as a substituent, 【Chemistry 8】 [In the formula, m ＤＡ１ , m ＤＡ２ and m ＤＡ３ each independently represents an integer of 0 or more; G ＤＡ represents a nitrogen atom, an aromatic hydrocarbon group or a 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; Ar 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. 【Chemistry 9】 [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 nitrogen atom, an aromatic hydrocarbon group or a 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; Ar 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. 【Chemistry 10】 [In the formula, m ＤＡ１ represents an integer of 0 or more; Ar ＤＡ１ represents 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.

7. R which does not form a group represented by formula (P) １ , R ２ , R ３ , R or R ６ is a group represented by the formula (DA), the formula (DB), or the formula (DC).

8. The metal complex according to claim 7, wherein R4 which does not form a group represented by formula (P) is a group represented by formula (DA), formula (DB), or formula (DC).

9. A metal complex according to any one of claims 1 to 8, At least one material selected from the group consisting of a host material, a light-emitting material other than the metal complex, an antioxidant, and a solvent; A composition comprising:

10. The composition according to claim 9, wherein the host material contains at least one of a low molecular weight compound represented by the following formula (H-1) and a polymer compound containing a structural unit represented by the following formula (Y): 【Chemistry 11】 [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; n Ｈ１ When multiple are present, they may be the same or different; Ｈ２ If there are multiple n Ｈ２ may be the same or different; n Ｈ３ represents an integer of 0 or more; L Ｈ１ is an arylene group, a divalent heterocyclic group, or -[C(R Ｈ１１ ) ２ ]n Ｈ１１ -, which may have a substituent; L Ｈ１ When multiple are present, they may be the same or different, and n Ｈ１１ represents an integer of 1 or more and 10 or less; R Ｈ１１ 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. Ｈ１１ may be the same or different and may be bonded to each other to form a ring together with the carbon atom to which they are bonded; L Ｈ２ is -N(-L Ｈ２１ -R Ｈ２１ )- represents a group represented by the formula: Ｈ２ If there are multiple L Ｈ２ may be the same or different; L Ｈ２１ represents a single bond, an arylene group, or a divalent heterocyclic group, and these groups may have a substituent; R 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. 【Chemistry 12】 [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.

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

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