Composition, polymer compound and light-emitting device

Abstract

To provide a composition useful for producing a light emitting device having high external quantum efficiency.SOLUTION: A composition has at least one selected from the group consisting of a condensed ring compound (1-1) represented by formula (1) and a polymer compound (1-2) having the constitutional unit formed by removing one or more hydrogen atoms from the condensed ring compound (1-1), and a polymer compound (2-1) having a constitutional unit represented by formula (Y).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a composition, a polymer compound, and a light-emitting device. [Background technology]

[0002] Organic electroluminescence elements (hereinafter also referred to as light-emitting elements) can be suitably used for, for example, displays and lighting applications. For example, Patent Document 1 proposes a compound represented by formula (B0) as a light-emitting material used in a light-emitting layer of the light-emitting element. [ka] [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2020 / 080528 Summary of the Invention [Problem to be solved by the invention]

[0004] However, the external quantum efficiency of the light-emitting device produced using the compound described in Patent Document 1 was not necessarily sufficient.

[0005] Therefore, an object of the present invention is to provide a composition that is useful for producing a light-emitting device having high external quantum efficiency. [Means for solving the problem]

[0006] The present invention provides the following [1] to

[11] . [1] At least one member selected from the group consisting of a fused ring compound (1-1) represented by formula (1) and a polymer compound (1-2) having a structural unit obtained by removing one or more hydrogen atoms from the fused ring compound (1-1); A composition comprising a polymer compound (2-1) having a structural unit represented by formula (Y): [ka] [In formula (1), Ring A, ring B and ring C each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. Y 1 represents B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R. R represents an aryl group, an alkyl group, or a cycloalkyl group, and these groups may have a substituent. X 1 represents N or CR. X 2 are O, N-R', and C(-R''). 2 , S or Se. R' represents an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, which may have a substituent. R'' represents a hydrogen atom, an aryl group, an alkyl group or a cycloalkyl group, which may have a substituent. R' and R'' may each be bonded to ring A and / or ring C via a linking group or a single bond. X 1 When is N, some or all of two adjacent A rings may be bonded to each other via a single bond. n is an integer of 1 or greater. In formula (1), multiple symbols may be the same or different. When the fused ring compound (1-1) represented by formula (1) has hydrogen atoms, at least one of the hydrogen atoms may be substituted with a deuterium atom, a cyano group, or a halogen atom.] [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.] [2] Ring A, ring B and ring C are aromatic hydrocarbon rings which may have a substituent; X 1 is N, Y 1 is B, X 2 is O or N-R', The composition described in [1], wherein n is 1 or 2. [3] The composition according to [1] or [2], which contains the fused ring compound (1-1). [4] Ar Y1 is a phenylene group which may have a substituent, a fluorenediyl group which may have a substituent, or a group represented by formula (YY). [ka] [In the formula, Ar YY1 and Ar YY3 each independently represents an arylene group which may have a substituent; Ar YY2 represents a divalent nitrogen-containing aromatic heterocyclic group which may have a substituent. [5] A polymer compound comprising a structural unit obtained by removing one or more hydrogen atoms from a fused ring compound represented by formula (1), and a structural unit represented by formula (Y). [ka] [In formula (1), Ring A, ring B and ring C each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. Y 1 represents B, P, P=O, P=S, Al, Ga, As, Si-R, or Ge-R. R represents an aryl group, an alkyl group, or a cycloalkyl group, and these groups may have a substituent. X 1 represents N or CR. X 2are O, N-R', and C(-R''). 2 , S or Se. R' represents an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, which may have a substituent. R'' represents a hydrogen atom, an aryl group, an alkyl group or a cycloalkyl group, which may have a substituent. R' and R'' may each be bonded to ring A and / or ring C via a linking group or a single bond. X 1 When is N, some or all of two adjacent A rings may be bonded to each other via a single bond. n is an integer of 1 or greater. In formula (1), multiple symbols may be the same or different. When the fused ring compound (1-1) represented by formula (1) has hydrogen atoms, at least one of the hydrogen atoms may be substituted with a deuterium atom, a cyano group, or a halogen atom.] [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.] [6] Ring A, ring B and ring C are aromatic hydrocarbon rings which may have a substituent; X 1 is N, Y 1 is B, X 2 is O or N-R', The polymer compound according to [5], wherein n is 1 or 2. [7] Ar Y1 is a phenylene group which may have a substituent, a fluorenediyl group which may have a substituent, or a group represented by formula (YY). [ka] [In the formula, Ar YY1 and Ar YY3 each independently represents an arylene group which may have a substituent; Ar YY2 represents a divalent nitrogen-containing aromatic heterocyclic group which may have a substituent. [8] A composition comprising the polymer compound according to any one of [5] to [7]. [9] The composition according to any one of [1] to [4] and [8], further comprising a metal complex represented by formula (Z): [ka] [In the formula, M 1 represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1 represents an integer of 1 or more, and n 2 represents an integer of 0 or more. However, M 1 When is a ruthenium atom, a rhodium atom, or an iridium atom, n 1 +n 2 is 3, and M 1 When n is a palladium atom or a platinum atom, 1 +n 2 is 2. E 1 and E 2 each independently represents a nitrogen atom or a carbon atom. Ring L 1 and ring L 2 each independently represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which they are bonded. A 1 -G 1 -A 2 represents an anionic bidentate ligand. 1 and A 2Each of G independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. 1 is a single bond or A 1 and A 2 Together, these represent the atomic groups that constitute a bidentate ligand. In formula (Z), a plurality of symbols may have the same or different meanings.

[10] The composition according to any one of [1] to [4], [8] and [9], further comprising at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent.

[11] A light-emitting device comprising the composition according to any one of [1] to [4] and [8] to

[10] , or the polymer compound according to any one of [5] to [7].

[12] A light-emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode, the first organic layer contains the composition according to any one of [1] to [4] and [8] to

[10] , or the polymer compound according to any one of [5] to [7]; The light-emitting device according to

[11] , wherein the second organic layer contains a crosslinked body of a crosslinkable material. Effect of the Invention

[0007] According to the present invention, a composition useful for manufacturing a light-emitting device having high external quantum efficiency can be provided. In addition, according to the present invention, a polymer compound useful for preparing the composition can be provided. In addition, according to the present invention, a light-emitting device having high external quantum efficiency containing the composition can be provided. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] Preferred embodiments of the present invention will now be described in detail.

[0009] <Explanation of common terms> Terms commonly used in this specification have the following meanings unless otherwise specified. 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. The hydrogen atom may be a deuterium atom or a protium atom. In the formula representing a metal complex, the solid line representing a bond with a metal means an ionic bond, a covalent bond or a coordinate bond.

[0010] "Polymer compounds" are compounds that have a molecular weight distribution and have a number average molecular weight of 1 x 10 3 or more (e.g. 1×10 3 ~1×10 8 ) means a polymer in which The polymer compound may be any one of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, 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 reduced when the polymer compound is used to prepare a light-emitting device. The end group of the polymer compound is preferably a group that is conjugated with the main chain, and examples of the end group include an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond. A "low molecular weight compound" is a compound that does not have a molecular weight distribution and has a molecular weight of 1×10 4 The following compound is meant: 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."

[0011] 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 also be a group in which some or all of the hydrogen atoms in these groups have been substituted with a substituent (e.g., a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.) (e.g., a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, a 3-(4-methylphenyl)propyl group, a 3-(3,5-di-hexylphenyl)propyl group, or a 6-ethyloxyhexyl group).

[0012] The number of carbon atoms in a "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms in the substituent. The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group, a cyclohexylmethyl group, a cyclohexylethyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent (e.g., an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).

[0013] An "aromatic hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms directly bonded to an atom constituting a ring from an aromatic hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from an aromatic hydrocarbon is also called an "aryl group." A group obtained by removing two hydrogen atoms directly bonded to an atom constituting a ring from an aromatic hydrocarbon is also called an "arylene group." The aromatic hydrocarbon group has usually 6 to 60 carbon atoms, preferably 6 to 40 carbon atoms, and more preferably 6 to 20 carbon atoms, not including the number of carbon atoms of the substituent. Examples of the "aromatic hydrocarbon group" include monocyclic aromatic hydrocarbons (e.g., benzene) or polycyclic aromatic hydrocarbons (e.g., bicyclic aromatic hydrocarbons such as naphthalene and indene; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, and fluorene; tetracyclic aromatic hydrocarbons such as benzoanthracene, benzophenanthrene, benzofluorene, pyrene, and fluoranthene; pentacyclic aromatic hydrocarbons such as dibenzanthracene, dibenzophenanthrene, dibenzofluorene, perylene, and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene; and heptacyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene). The aromatic hydrocarbon group includes groups in which a plurality of these groups are bonded. The aromatic hydrocarbon group may have a substituent.

[0014] The number of carbon atoms of the aryl group, not including the number of carbon atoms of the substituent, is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10. The aryl group may have a substituent. Examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-pyrenyl group, a 2-pyrenyl group, a 4-pyrenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, a 4-phenylphenyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent (for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).

[0015] The number of carbon atoms of 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, a chrysenediyl group, and groups in which a part or all of the hydrogen atoms in these groups are substituted with a substituent. The arylene group is preferably a group represented by formula (A-1) to formula (A-20). The arylene group includes a group in which a plurality of these groups are bonded. [ka] [ka] [ka] [ka] In the formula, 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.

[0016] The "alkoxy group" may be either linear or branched. The number of carbon atoms of a linear alkoxy group, not including the number of carbon atoms of the substituent, is usually 1 to 40, and preferably 4 to 10. The number of carbon atoms of a branched alkoxy group, not including the number of carbon atoms of the substituent, is usually 3 to 40, and preferably 4 to 10. The alkoxy group may have a substituent. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, a lauryloxy group, and groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent (e.g., a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.). 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, and examples thereof include a cyclohexyloxy group.

[0017] 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, and examples thereof include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, a 1-pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents (for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, etc.).

[0018] 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 a compound in which the heterocycle itself exhibits aromaticity, such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, or dibenzophosphole, and a compound in which an aromatic ring is condensed with a heterocycle, such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, or benzopyran, even if the heterocycle itself does not exhibit aromaticity.

[0019] 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, and examples thereof include a thienyl group, a pyrrolyl group, a furyl group, a pyridyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, a triazinyl group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents (for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, etc.).

[0020] 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 hetero atoms constituting the ring of pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, or triazole. The divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded. [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the formula, R and R a has the same meaning as above.

[0021] The term "halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0022] 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 a dialkylamino group, a dicycloalkylamino group, and a diarylamino group. Examples of the substituted amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis(4-methylphenyl)amino group, a bis(4-tert-butylphenyl)amino group, and a bis(3,5-di-tert-butylphenyl)amino group.

[0023] 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, 7-octenyl group, and 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, norbornylenyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with a substituent.

[0024] The "alkynyl group" may be either linear or branched. The number of carbon atoms of the alkynyl group, not including the carbon atoms of the substituent, is usually 2 to 20, preferably 3 to 20. The number of carbon atoms of the branched alkynyl group, not including the carbon atoms of the substituent, is usually 4 to 30, 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, a 5-hexynyl group, and 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 and groups in which some or all of the hydrogen atoms in this group are substituted with a substituent.

[0025] The "crosslinking group" refers to a group capable of generating a new bond by being subjected to heat treatment, ultraviolet ray irradiation treatment, near-ultraviolet ray irradiation treatment, visible light irradiation treatment, infrared ray irradiation treatment, radical reaction, or the like, and is preferably a crosslinking group represented by formulae (XL-1) to (XL-19) in Crosslinking Group Group A, more preferably a crosslinking group represented by formulae (XL-1), (XL-3), (XL-9), (XL-10), (XL-16) or (XL-17) to (XL-19), still more preferably a crosslinking group represented by formulae (XL-1), (XL-16) or (XL-17) to (XL-19), and particularly preferably a crosslinking group represented by formula (XL-1) or (XL-17). [ka] In the formula, R XL represents a methylene group, an oxygen atom, or a sulfur atom; n XL represents an integer from 0 to 5. XL When multiple are present, they may be the same or different. XL When there are multiple, they may be the same or different. *1 indicates the bonding position. These bridging groups may have a substituent, and when there are multiple such substituents, 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.

[0026] The "substituent" is preferably 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.

[0027] <Fused ring compound (1-1)> The fused ring compound (1-1) is a compound represented by formula (1). The fused ring compound (1-1) may be used alone or in combination of two or more kinds.

[0028] The number of carbon atoms in the aromatic hydrocarbon ring in ring A, ring B and ring C, not including the number of carbon atoms of the substituent, is usually 6 to 60, preferably 6 to 18, more preferably 6 to 10, and particularly preferably 6. Examples of the aromatic hydrocarbon ring include benzene, fluorene, naphthalene, anthracene and phenanthrene, and preferably benzene.

[0029] The number of carbon atoms in the aromatic heterocycle in ring A, ring B and ring C, not including the number of carbon atoms of the substituent, is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15. Examples of the aromatic heterocycle include pyridine, diazabenzene, azanaphthalene, diazanaphthalene, carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan and thiophene.

[0030] Examples of the substituents that the A ring, the B ring, and the C ring may have include a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or unsubstituted arylheteroarylamino group (an amino group having an aryl group and a heteroaryl group), a substituted or unsubstituted diarylboryl group (two aryl groups may be bonded via a single bond or a linking group), a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, and a substituted or unsubstituted alkoxy group are preferred, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted alkyl group, and a substituted or unsubstituted cycloalkyl group are more preferred, a substituted or unsubstituted aryl group, and a substituted or unsubstituted alkyl group are particularly preferred, and a substituted or unsubstituted alkyl group is particularly preferred. When these groups have a substituent, examples of the substituent include an aryl group, a heteroaryl group, an alkyl group, and a cycloalkyl group.

[0031] The A ring, the B ring and the C ring each represent Y 1 and X1 Multiple six-membered rings including Y 1 and X 2 It is preferable that the ring has a 5-membered ring or a 6-membered ring that shares a bond with a condensed structure of a plurality of 6-membered rings including the ring A. Here, examples of the "6-membered ring that shares a bond with the condensed structure" include the ring a (benzene ring), the ring b (benzene ring) and the ring c (benzene ring) in the compound shown in formula (2). In addition, "the ring A has a 6-membered ring that shares a bond with the condensed structure" means that the ring A is formed only by this 6-membered ring, or that another ring is condensed to this 6-membered ring to form the ring A. In other words, "the ring A has a 6-membered ring that shares a bond with the condensed structure" means that the 6-membered ring that constitutes all or a part of the ring A is condensed to the condensed structure. The same explanation applies to the "ring B", "ring C" and "5-membered ring".

[0032] [ka]

[0033] The A ring, B ring and C ring in formula (1) are each independently a ring a and its multiple substituents R a , b ring and its multiple substituents R b and ring c and its multiple substituents R c That is, it can be said that the formula (2) is a compound in which 6-membered rings are selected as the A ring, the B ring, and the C ring of the formula (1).

[0034] In formula (2), adjacent R on the a ring a They may be bonded to each other to form ring A (aromatic hydrocarbon ring or aromatic heterocycle) together with ring a. In addition, in formula (2), adjacent R on ring b b They may be bonded to each other to form ring B (aromatic hydrocarbon ring or aromatic heterocycle) together with ring b. In addition, in formula (2), adjacent R on ring c may c They may be bonded together to form a ring C (aromatic hydrocarbon ring or aromatic heterocycle) together with the ring c. The formed ring may have a substituent, and examples of the substituent include the substituents that the ring A, ring B, and ring C may have.

[0035] That is, in formula (2), R a represents a hydrogen atom or a substituent, or the adjacent R a R and R are bonded together to form an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent together with the a ring. b represents a hydrogen atom or a substituent, or the adjacent R b R and R are bonded together to form an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent together with the b ring. c represents a hydrogen atom or a substituent, or the adjacent R c R is bonded to the ring c to form an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent together with the ring c. a , R b and R c Examples of the substituent in the above formula include the substituents which the above-mentioned A ring, B ring and C ring may have.

[0036] In one preferred embodiment, R a may be a hydrogen atom or a substituent. b is a set of three R on one b-ring. b Two adjacent R b are bonded to each other to form an aromatic hydrocarbon ring or an aromatic heterocycle together with the b ring, and the remaining R b may be a hydrogen atom or a substituent. C is a set of four R c Two adjacent R c are bonded together to form an aromatic hydrocarbon ring or an aromatic heterocycle together with the c ring, and the remaining two R c may be a hydrogen atom or a substituent.

[0037] In another preferred embodiment, R a is three R on one a-ring. a Two adjacent R a are bonded together to form an aromatic hydrocarbon ring or an aromatic heterocycle together with the a ring, and the remaining Ra may be a hydrogen atom or a substituent. b and R c may each independently be a hydrogen atom or a substituent.

[0038] In yet another preferred embodiment, R a , R b and R c may each independently be a hydrogen atom or a substituent.

[0039] R a , R b or R c The ring formed with the ring a, ring b, or ring c may be, for example, a fused ring formed by fusing a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring to the ring a, ring b, or ring c which is a benzene ring. The fused ring may be, for example, a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

[0040] Y in formula (1) 1 represents B, P, P=O, P=S, Al, Ga, As, Si-R or Ge-R, preferably B, P, P=O, P=S or Si-R, more preferably B. R represents an aryl group, an alkyl group or a cycloalkyl group, which may have a substituent. As the substituent that R may have, an aryl group or an alkyl group is preferable, and an aryl group is more preferable.

[0041] X in formula (1) 1 represents N or CR, and is preferably N. R has the same meaning as above.

[0042] X in formula (1) 2 are O, N-R', and C(-R''). 2 , S or Se, preferably O, N-R' or C(-R'') 2and more preferably O or N-R', and even more preferably O. R' represents an aryl group, a heteroaryl group, an alkyl group, or a cycloalkyl group, which may have a substituent. R'' represents a hydrogen atom, an aryl group, an alkyl group, or a cycloalkyl group, which may have a substituent. As the substituent that R' may have, an aryl group or a heteroaryl group is preferable, and an aryl group is more preferable. As the substituent that R'' may have, an aryl group, a heteroaryl group, or an alkyl group is preferable, and an aryl group or an alkyl group is more preferable.

[0043] R' and R'' may be bonded to ring A and / or ring C via a linking group or a single bond. Examples of the linking group include O, S, C(-R'') 2 R″ is as defined above.

[0044] The two Xs in Equation (1) 2 may both be O, both be NR, or one be O and the other be NR.

[0045] The provision in formula (1) that "R' and R'' may each be bonded to ring A and / or ring C via a linking group or a single bond" corresponds to the provision in formula (2) that "R' and R'' may each be bonded to ring a and / or ring c via a linking group or a single bond."

[0046] The provision in formula (1) that "R' and R'' may be bonded to ring A and / or ring C via a linking group or a single bond" may be used in the case of, for example, X 2 The compound can be expressed as a compound having a ring structure in which X is incorporated into the fused ring C'. For example, the compound can be expressed as a compound having a ring structure in which X is incorporated into the fused ring C' in the ring c in formula (2). 2 It can also be said that the compound has a ring C' formed by condensing another ring so as to incorporate the ring C. The ring C' formed may be, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or the like. In addition, the provision in formula (1) that "R' and R'' may be bonded to ring A and / or ring C via a linking group or a single bond" is applicable to, for example, X represented by formula (2-1-2): 2 The compound can also be expressed as a compound having a ring structure in which X is incorporated into the fused ring A'. For example, the compound can be expressed as a compound having a ring structure in which X is incorporated into the fused ring A' in the formula (2). 2 It can also be said that the compound has an A' ring formed by condensing another ring so as to incorporate the ring. The A' ring formed may be, for example, a phenoxazine ring, a phenothiazine ring, an acridine ring, or the like. [ka] [ka]

[0047] X 1 When n is N, some or all of two adjacent A rings may be bonded together via a single bond. In such a case, it is preferable that all two adjacent A rings are bonded together via a single bond. When n is 2 or more, the number of A rings is 3 or more, and two or more adjacent A rings are bonded together, so "some or all" means "some positions" or "all positions" among these multiple positions.

[0048] The following is an example of formula (2): 1 is N, and some or all of the two adjacent a rings are bonded to each other by a single bond. Each symbol in each formula is defined as above. a Part of R b and R c has been omitted. [ka]

[0049] The fused ring compound (1-1) represented by formula (1) is 1 is N and Y 1 is B and X2 is preferably O or N-R'.

[0050] In formula (1), n ​​is preferably 1 or 2, and more preferably 1.

[0051] When n in formula (1) is 1, the following compounds can be mentioned. Each symbol in each formula is the same as defined above. In the following examples, X 1 is N and Y 1 is B and X 2 Although the examples where X is O or N-R' have been shown, 1 , Y 1 and X 2 There are also other combinations of rings A. There are also other combinations of rings A that are adjacent to each other and are bonded together by a single bond. [ka]

[0052] When n in formula (1) is 2, the following compounds can be mentioned. Each symbol in each formula is the same as defined above. In the following examples, X 1 is N and Y 1 is B and X 2 Although the examples where X is O or N-R' have been shown, 1 , Y 1 and X 2 Other combinations are also possible. Examples in which two adjacent A rings are bonded to each other via a single bond are also possible. Examples in which some or all of two adjacent A rings are bonded to each other via a single bond are also possible. [ka]

[0053] When n in formula (2) is 1, the following compounds can be mentioned. Each symbol in each formula is the same as defined above. In the following, R a , R b , R c, and the substituents on R' (phenyl group in the formula) of N-R' are omitted. 1 is B and X 1 is N and X 2 Although the examples where X is O or N-R' have been shown, 1 , Y 1 and X 2 There are other combinations of the rings. There are also examples in which two adjacent a rings are bonded together by a single bond. [ka]

[0054] The following examples show that R' (phenyl group in the formula) of N-R' is bonded to ring c (or ring a). Note that, although the following examples show cases where the linking group for bonding is a single bond or O, there are also cases where the linking group is another group. [ka]

[0055] When n in formula (2) is 2, the following compounds can be mentioned. Each symbol in each formula is the same as defined above. In the following, R a , R b , R c , and the substituents on R' (phenyl group in the formula) of N-R' are omitted. 1 is B and X 1 is N and X 2 Although the examples where X is O or N-R' have been shown, 1 , Y 1 and X 2 Other combinations of the rings may also exist. In addition, some or all of the adjacent rings a may be bonded to each other via a single bond. [ka]

[0056] The following examples show that R' (phenyl group in the formula) of N-R' is bonded to ring c (or ring a). Note that, although the following examples show cases where the linking group for bonding is a single bond or O, there are also cases where the linking group is another group. [ka]

[0057] Next, the structures of the A ring, B ring and C ring (CA, CB and CC) will be described in more detail. [ka]

[0058] Specific examples of the structure (CA) of the A ring include structures represented by formulae (CA01) to (CA38). Since the external quantum efficiency of the light-emitting device is excellent, the structures represented by formulae (CA01) to (CA19) are preferred, the structures represented by formulae (CA01) to (CA05) are more preferred, and the structure represented by formula (CA01) is even more preferred. [ka] [ka] [ka] [ka] [In the formula, R Ca represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group. Ca may be the same or different, R Ca may be bonded to each other to form a ring together with the atoms to which they are bonded. R CY2represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. CY2 ) 2 -, -CR CY2 =CR CY2 - or -C(R CY2 ) 2 -C(R CY2 ) 2 In the group represented by -, multiple R CY2 Of these, two R CY2 may be bonded to each other to form a ring. CY2 may be the same or different. R CY4 R represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. CY4 When multiple are present, they may be the same or different. In the formula, the hydrogen atom may be replaced by a substituent which the ring A may have.]

[0059] R Ca 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.

[0060] R CY2 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.

[0061] R CY4 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 even more preferably an aryl group, and these groups may have a substituent.

[0062] Specific examples of the structure (CB) of the B ring include structures represented by formulae (CB01) to (CB24). Since the external quantum efficiency of the light-emitting device is excellent, the structures represented by formulae (CB01) to (CB13) are preferred, the structures represented by formulae (CB01) to (CB05) are more preferred, and the structure represented by formula (CB01) is particularly preferred. [ka] [ka] [ka] [In the formula, R CY2 , R CY4 and R Ca has the same meaning as above. In the formula, a hydrogen atom may be replaced by a substituent which the ring B may have.]

[0063] Specific examples of the structure (CC) of the C ring include structures represented by formulae (CC01) to (CC24), preferably structures represented by formulae (CC01) to (CC13), more preferably structures represented by formulae (CC01) to (CC05), and even more preferably structures represented by formula (CC01). [ka] [ka] [ka] [In the formula, R CY2 , R CY4 and R Ca has the same meaning as above. In the formula, a hydrogen atom may be replaced by a substituent which the C ring may have.]

[0064] In the formulae (CA02) to (CA05), (CB02) to (CB05), and (CC02) to (CC05), -C(R CY2 ) 2 Two R CY2 The combination of -C(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 such that one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent. CY2 ) 2 - in the group represented by CY2 When they are bonded to each other to form a ring together with the carbon atom, -C(R CY2 ) 2 The group represented by - is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups may have a substituent. [ka]

[0065] In the formulae (CA09) to (CA12), (CB08) to (CB10), and (CC08) to (CC10), -C(R CY2 )=C(R CY2 Two R in the group represented by CY2 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.

[0066] In the formulae (CA13) to (CA16), (CB11), (CB12), (CC11), and (CC12), -C(R CY2 ) 2 -C(R CY2 ) 2 - represents one of the four R CY2is preferably an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent. CY2 may be bonded to each other to form a ring together with the carbon atom to which they are bonded, R CY2 When forms a ring, -C(R CY2 ) 2 -C(R CY2 ) 2 The group represented by - is preferably a group represented by formula (Y-B11) to formula (Y-B15), more preferably a group represented by formula (Y-B13), and these groups may have a substituent. [ka] [In the formula, R CY2 has the same meaning as above.]

[0067] In this embodiment, the combination of ring A, ring B and ring C is preferably a combination in which ring A has a structure represented by formulae (CA01) to (CA05), ring B has a structure represented by formulae (CB01) to (CB05), and ring C has a structure represented by formulae (CC01) to (CC05), more preferably a combination in which ring A has a structure represented by formula (CA01), ring B has a structure represented by formulae (CB01) to (CB05), and ring C has a structure represented by formulae (CC01) to (CC05), and even more preferably a combination in which ring A has a structure represented by formula (CA01), ring B has a structure represented by formula (CB01), and ring C has a structure represented by formula (CC01).

[0068] Examples of the fused ring compound (1-1) represented by formula (1) include compounds represented by formulas (1-101) to (1-146). [ka] [ka] [ka] [ka] [ka] [ka]

[0069] <High molecular compound (1-2), high molecular compound (2-1)> The polymer compound (1-2) is a polymer compound having a structural unit (1-2-a) obtained by removing one or more (preferably two or more, more preferably two) hydrogen atoms from the fused ring compound (1-1). The polymer compound (1-2) may be used alone or in combination of two or more. The polymer compound (1-2) may have only one type of structural unit (1-2-a) or may have two or more types of structural unit (1-2-a). The polymer compound (1-2) may have a group in the terminal structure obtained by removing one hydrogen atom from the fused ring compound (1-1).

[0070] The polymer compound (2-1) is a polymer compound having a structural unit represented by formula (Y) (hereinafter, also referred to as structural unit (Y)). The polymer compound (2-1) does not have a structural unit (1-2-a). The polymer compound (2-1) may be used alone or in combination of two or more kinds. The polymer compound (2-1) may have only one kind of structural unit (Y), or may have two or more kinds of structural unit (Y).

[0071] The polymer compound (1-2) may have the structural unit (1-2-a) as a repeating unit. The polymer compound (1-2) may be a homopolymer having only one type of structural unit (1-2-a) as a repeating unit, a copolymer having two or more types of structural units (1-2-a) as a repeating unit, or a copolymer having the structural unit (1-2-a) and another structural unit (e.g., a structural unit represented by formula (Y)) as a repeating unit.

[0072] The polymer compound (2-1) may have a structural unit (Y) as a repeating unit. The polymer compound (2-1) may be a homopolymer having only one type of structural unit (Y) as a repeating unit, a copolymer having two or more types of structural units (Y) as a repeating unit, or a copolymer having the structural unit (Y) and other structural units.

[0073] The structural unit (1-2-a) is preferably a structural unit obtained by removing two or more hydrogen atoms (more preferably two) from the fused ring compound (1-1).

[0074] The structural unit (1-2-a) may be a structural unit in which one or more hydrogen atoms (preferably two or more, more preferably two) have been removed from ring A, ring B or ring C of the fused ring compound (1-1), and from the viewpoint of synthesis, it is preferably a structural unit in which one or more hydrogen atoms (preferably two or more, more preferably two) have been removed from ring A or ring C, and more preferably a structural unit in which one or more hydrogen atoms (preferably two or more, more preferably two) have been removed from ring C. The structural unit (1-2-a) may be a structural unit obtained by removing one or more hydrogen atoms (preferably two or more, more preferably two) from the substituent of the A ring, the substituent of the B ring, the substituent of the C ring, R, R', or R'' of the fused ring compound (1-1). From the viewpoint of synthesis, it is a structural unit obtained by removing one or more hydrogen atoms (preferably two or more, more preferably two) from the R' or R'' of the fused ring compound (1-1), and more preferably a structural unit obtained by removing one or more hydrogen atoms (preferably two or more, more preferably two) from the R' of the fused ring compound (1-1). In the structural unit having a plurality of R' or R'' and having two or more hydrogen atoms removed, it is preferable that the structural unit is a structural unit obtained by removing one hydrogen atom from each of the different R' or R''.

[0075] When the polymer compound (1-2) is a copolymer having the structural unit (1-2-a) and the structural unit (Y), the structural unit (1-2-a) and the structural unit (Y) may be bonded directly or via a substituent.

[0076] Examples of the structural unit (1-2-a) include structural units represented by formulas (2-101) to (2-132). [ka] [ka] [ka] [ka] [ka]

[0077] The structural unit (Y) is a structural unit different from the structural unit (1-2-a). The structural unit (Y) may be contained in the polymer compound in one type or in two or more types, and preferably in two or more types.

[0078] 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, and these groups may have a substituent. The substituent that these groups may have 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, and these groups may further have a substituent.

[0079] Ar Y1 is preferably a phenylene group, a fluorenediyl group, or a divalent group represented by the formula (YY), and these groups may have a substituent.

[0080] Ar Y1 The arylene group represented by the formula (A-1), (A-2), (A-6) to (A-10), (A-19) or (A-20) is particularly preferably a group represented by the formula (A-1), (A-2), (A-7), (A-9) or (A-19), and these groups may have a substituent.

[0081] Ar Y1 The divalent heterocyclic group represented by the formula (AA-1) to (AA-4), (AA-10) to (AA-15), (AA-18) to (AA-21), (AA-33) or (AA-34) is particularly preferably a group represented by formula (AA-4), (AA-10), (AA-12), (AA-14) or (AA-33), and these groups may have a substituent.

[0082] Ar Y1In the divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, the particularly preferred ranges of the arylene group and the divalent heterocyclic group are the same as those in the above-mentioned Ar Y1 The particularly preferred ranges and especially preferred ranges are the same as those of the arylene group and divalent heterocyclic group represented by the following formula:

[0083] Examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" include groups represented by the following formulae, which may have a substituent. [ka] [In the formula, R XX represents a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

[0084] R XX is preferably an alkyl group or an aryl group, and these groups may have a substituent.

[0085] Ar Y1 The substituent which the group represented by the following formula may have is preferably an alkyl group or an aryl group, and these groups may further have a substituent.

[0086] As the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded", a group represented by formula (YY) is preferable.

[0087] In formula (YY), Ar YY1 and Ar YY3As the arylene group in the formula (I), a phenylene group, a biphenylene group, a naphthalenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a fluorenediyl group, and a pyrenediyl group are preferable, a phenylene group, a biphenylene group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, and a fluorenediyl group are more preferable, and a phenylene group and a biphenylene group are even more preferable, and these groups may have a substituent.

[0088] In formula (YY), Ar YY3 The divalent nitrogen-containing aromatic heterocyclic group in the above means a divalent group obtained by removing two hydrogen atoms from a compound having a nitrogen-containing aromatic heterocycle, among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the nitrogen-containing aromatic heterocycle. Examples of the compound having a nitrogen-containing aromatic heterocycle include pyridine, diazabenzene, triazine, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, etc., preferably triazine and carbazole, more preferably triazine.

[0089] The constitutional unit represented by formula (Y) may be a group in which two or more types of arylene groups are directly bonded.

[0090] Examples of the structural unit represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-10). From the viewpoint of achieving a superior luminance life during initial driving of the light-emitting element, preferred are structural units represented by formulas (Y-1) to (Y-3). From the viewpoint of electron transport properties, preferred are structural units represented by formulas (Y-4) to (Y-7). From the viewpoint of hole transport properties, preferred are structural units represented by formulas (Y-8) to (Y-10).

[0091] [ka] [In the formula, R Y1represents a hydrogen atom, an alkyl group, an alkoxy 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.

[0092] R Y1 is preferably a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.

[0093] The formula (Y-1) may contain only one type, or may contain two or more types, and preferably contains two or more types.

[0094] The constitutional unit represented by formula (Y-1) may be a constitutional unit represented by formula (Y-1'). [ka] [In the formula, R Y11 represents an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. Y11 may be the same or different.]

[0095] R Y11 is preferably an alkyl group or an aryl group, more preferably an alkyl group, and these groups may have a substituent.

[0096] [ka] [In the formula, R Y1 has the same meaning as above. X Y1 is -C(R Y2 ) 2 -, -C(R Y2 )=C(R Y2 )-or-C(R Y2 ) 2 -C(R Y2 )2 R represents a group represented by the formula: Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, 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.

[0097] X Y1 is -C(R Y2 ) 2 -or-C(R Y2 )=C(R Y2 )-, and -C(R Y2 ) 2 It is more preferable that the group is a group represented by -.

[0098] R Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group or an aryl group, and these groups may have a substituent. As the substituent that the alkyl group or aryl group may have, an alkyl group or an aryl group is preferable, and these may further have a substituent.

[0099] X Y1 In the above, -C(R Y2 ) 2 Two R Y2 The combination of is preferably such that both are alkyl groups, both are aryl groups, both are monovalent heterocyclic groups, or one is an alkyl group and the other is an aryl group or a monovalent heterocyclic group, and more preferably, both are aryl groups, or one is an alkyl group and the other is an aryl group, and these groups may have a substituent. The substituent that the aryl group may have is preferably an alkyl group or an aryl group (more preferably an aryl group), and the substituent that the alkyl group may have is preferably an alkyl group or an aryl group, which may further have a substituent. Two R Y2may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 ) 2 The group represented by - is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups may have a substituent. [ka]

[0100] X Y1 In the above, -C(R Y2 )=C(R Y2 Two R in the group represented by Y2 The combination of the above is preferably such that both are alkyl groups, or one is an alkyl group and the other is an aryl group, and these groups may have a substituent.

[0101] X Y1 In the above, -C(R Y2 ) 2 -C(R Y2 ) 2 - represents one of the four R Y2 is preferably an alkyl group which may have a substituent. Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, R Y2 When forms a ring, -C(R Y2 ) 2 -C(R Y2 ) 2 The group represented by - is preferably a group represented by formula (Y-B1) to formula (Y-B5), more preferably a group represented by formula (Y-B3), and these groups may have a substituent. [ka] [In the formula, R Y2 has the same meaning as above.]

[0102] The constitutional unit represented by formula (Y-2) may be a constitutional unit represented by formula (Y-2'). [ka] [In the formula, R Y1 and X Y1 has the same meaning as above.]

[0103] [ka] [In the formula, R Y1 and X Y1 has the same meaning as above.]

[0104] The constitutional unit represented by formula (Y-3) may be a constitutional unit represented by formula (Y-3'). [ka] [In the formula, R Y11 and X Y1 has the same meaning as above.]

[0105] [ka] [In the formula, R Y1 has the same meaning as above. Y3 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

[0106] R Y3 is preferably an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0107] The constitutional unit represented by formula (Y-4) may be a constitutional unit represented by formula (Y-4'), and the constitutional unit represented by formula (Y-6) may be a constitutional unit represented by formula (Y-6'). [ka] [In the formula, R Y1 and R Y3 has the same meaning as above.]

[0108] [ka] [In the formula, R Y1 R has the same meaning as above. Y4 represents a hydrogen atom, an alkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

[0109] R Y4 is preferably an alkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.

[0110] Examples of the structural unit represented by formula (Y) include structural units composed of arylene groups represented by formulas (Y-101) to (Y-132), structural units composed of divalent heterocyclic groups represented by formulas (Y-201) to (Y-207), and structural units composed of divalent groups in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other represented by formulas (Y-301) to (Y-308). [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0111] The polymer compound (1-2) and the polymer compound (2-1) may each further contain a constitutional unit represented by formula (V). [ka] [In the formula, a V1 and a V2 each independently represents an integer of 0 or greater. Ar VA1 and Ar VA3 each independently represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. VA1 and Ar VA3at least one of the atoms adjacent to the atom that forms a bond with an adjacent structural unit has an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group as a substituent, and these substituents may further have a substituent. Ar VA2 and Ar VA4 each independently represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other, and these groups may have a substituent. R VA1 , R VA2 and R VA3 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.

[0112] The content of the structural unit (1-2-a) in the polymer compound (1-2) is preferably 0.01 to 50 mol %, more preferably 0.1 to 15 mol %, and even more preferably 0.5 to 5 mol %, based on the total amount of all structural units in the polymer compound (1-2).

[0113] In the polymer compound (1-2), the structural unit (Y) is Ar Y1 The content of the structural unit in which is an arylene group is preferably 10 to 95 mol %, and more preferably 30 to 90 mol %, based on the total amount of all structural units in the polymer compound (1-2), since this results in better external quantum efficiency of the light-emitting device.

[0114] In the polymer compound (1-2), the structural unit (Y) is Ar Y1 The content of the structural unit which is a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other is preferably 0.5 to 30 mol %, and more preferably 3 to 20 mol %, based on the total amount of all structural units in the polymer compound (1-2), in order to achieve better external quantum efficiency of the light-emitting device.

[0115] In the polymer compound (2-1), the structural unit (Y) is Ar Y1 The content of the structural unit in which is an arylene group is preferably 10 to 95 mol %, and more preferably 30 to 90 mol %, based on the total amount of all structural units in the polymer compound (2-1), since this results in better external quantum efficiency of the light-emitting device.

[0116] In the polymer compound (2-1), the structural unit (Y) is Ar Y1 The content of the structural unit which is a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other is preferably 0.5 to 30 mol %, and more preferably 3 to 20 mol %, based on the total amount of all structural units in the polymer compound (2-1), in order to achieve better external quantum efficiency of the light-emitting device.

[0117] Examples of the polymer compound (1-2) include polymer compounds P-1 to P-4 shown in Table 1.

[0118] [Table 1]

[0119] In Table 1, p, q, r, and s represent the molar ratio of each structural unit. p+q+r+s=100, and 70≦p+q+r≦100. Other structural units refer to structural units other than the structural units (1-2-a), and the structural units represented by formula (Y) and formula (V).

[0120] Examples of the polymer compound (2-1) include polymer compounds P-5 to P-8 shown in Table 2.

[0121] [Table 2]

[0122] In Table 2, q', r', and s' represent the molar ratio of each structural unit, where q'+r'+s'=100 and 70≦q'+r'≦100. Other structural units refer to structural units other than those represented by formula (Y) and formula (V).

[0123] In this embodiment, the weight average molecular weight (Mw) of the polymer compound in terms of polystyrene is preferably 5.0×10 because the external quantum efficiency of the light-emitting device is superior. 3 ~1.0×10 6 and more preferably 1.0×10 4 ~5.0×10 5 and more preferably 1.0×10 4 ~4.0×10 5 and particularly preferably 1.0×10 4 ~3.5×10 5 It is.

[0124] In this embodiment, the number average molecular weight (Mn) of the polymer compound in terms of polystyrene is preferably 2.5×10 because the external quantum efficiency of the light-emitting device is superior. 3 ~5.0×10 5 and more preferably 5.0×10 3 ~2.5×10 4 and more preferably 5.0×10 3 ~2.0×10 5 and particularly preferably 5.0×10 3 ~1.8×10 5 It is.

[0125] The end group of the polymer compound of this embodiment is preferably a stable group, since if the polymerization active group remains as it is, the light-emitting properties or luminance life may be reduced when the polymer compound is used to prepare a light-emitting device. The end group of the polymer compound is preferably a group that is conjugated with the main chain, and examples of the end group include an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond.

[0126] The polymer compound of the present embodiment may be any one of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be in other forms, but is preferably a copolymer obtained by copolymerizing a plurality of types of raw material monomers.

[0127] <Method of producing polymer compound> Next, a method for producing the polymer compound of this embodiment will be described. The polymer compound of this embodiment can be produced, for example, by condensation polymerization of a compound represented by formula (M-1) and a compound represented by formula (M-2), condensation polymerization of a compound represented by formula (M-1) and a compound represented by formula (M-4), condensation polymerization of a compound represented by formula (M-3) and a compound represented by formula (M-2), condensation polymerization of a compound represented by formula (M-3) and a compound represented by formula (M-4), condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-2), and a compound represented by formula (M-3), condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-2), and a compound represented by formula (M-4), or condensation polymerization of a compound represented by formula (M-1), a compound represented by formula (M-3), and a compound represented by formula (M-4). In this specification, the compounds used in the production of a polymer compound may be collectively referred to as "raw material monomers". [ka] [ka] [ka] [ka] [In the formula, Ar Y1 has the same meaning as above. Ar Y2 represents a group obtained by removing two hydrogen atoms from the fused ring compound (1-1). ZC1 ~Z C4 each independently represents a group selected from the group consisting of Substituent Group A and Substituent Group B.]

[0128] For example, Z C1 and Z C2 is a group selected from the substituent group A, Z C3 and Z C4 is selected from the substituent group B.

[0129] For example, Z C1 and Z C2 is a group selected from the substituent group B, Z C3 and Z C4 is a group selected from the substituent group A.

[0130] For example, Z C1 and Z C3 is a group selected from the substituent group A, Z C2 and Z C4 is selected from the substituent group B.

[0131] <Substituent group A> Chlorine atom, bromine atom, iodine atom, and -OS(=O) 2 R C1 (In the formula, R C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

[0132] <Substituent group B> -B(OR C2 ) 2 (In the formula, R C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. C2 may be the same or different and may be linked to each other to form a ring structure together with the oxygen atom and boron atom to which they are bonded; -B.F. 3 A group represented by Q' (wherein Q' represents Li, Na, K, Rb, or Cs); A group represented by -MgY' (wherein Y' represents a chlorine atom, a bromine atom, or an iodine atom); -ZnY″ (wherein Y″ represents a chlorine atom, a bromine atom, or an iodine atom); and -Sn(R C3 ) 3 (In the formula, R C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. C3 may be the same or different and may be linked to each other to form a ring structure together with the tin atom to which they are bonded.

[0133] -B(OR C2 ) 2 Examples of the group represented by the formula include groups represented by the following formulas: [ka]

[0134] A compound having a group selected from the substituent group A and a compound having a group selected from the substituent group B are condensation polymerized by a known coupling reaction to bond carbon atoms bonded to a group selected from the substituent group A and a group selected from the substituent group B. Therefore, by subjecting a compound having two groups selected from the substituent group A and a compound having two groups selected from the substituent group B to a known coupling reaction, a condensation polymer of these compounds can be obtained by condensation polymerization.

[0135] The condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, and may be carried out in the coexistence of a phase transfer catalyst, if necessary.

[0136] Examples of the catalyst include palladium complexes such as bis(triphenylphosphine)palladium(II) dichloride, bis(tris-o-methoxyphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone)dipalladium(0), and palladium acetate; transition metal complexes such as tetrakis(triphenylphosphine)nickel(0), [1,3-bis(diphenylphosphino)propane)nickel(II) dichloride, and bis(1,4-cyclooctadiene)nickel(0); and complexes of these transition metal complexes further having ligands such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, 1,3-bis(diphenylphosphino)propane, and bipyridyl. The catalyst may be used alone or in combination of two or more.

[0137] The amount of the catalyst used is usually 0.00001 to 3 molar equivalents in terms of the amount of transition metal relative to the total number of moles of the raw material monomers.

[0138] Examples of the base and phase transfer catalyst include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate, etc.; organic bases such as tetrabutylammonium fluoride, tetraethylammonium hydroxide, tetrabutylammonium hydroxide, etc.; and phase transfer catalysts such as tetrabutylammonium chloride, tetrabutylammonium bromide, etc. The base and phase transfer catalyst may each be used alone or in combination of two or more kinds.

[0139] The amount of the base and the phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of the raw material monomers.

[0140] Examples of the solvent include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N,N-dimethylacetamide, and N,N-dimethylformamide, and water. The solvent may be used alone or in combination of two or more.

[0141] The amount of the solvent used is usually 10 to 100,000 parts by mass per 100 parts by mass of the total of the raw material monomers.

[0142] The reaction temperature of the condensation polymerization is usually −100 to 200° C. The reaction time of the condensation polymerization is usually 1 hour or longer.

[0143] Post-treatment of the polymerization reaction can be carried out by any of the known methods, for example, a method of removing water-soluble impurities by liquid separation, a method of adding the reaction liquid after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying the precipitate, or a combination of these methods. When the purity of the polymer compound is low, it can be purified by a normal method such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, column chromatography, etc.

[0144] <Metal complex> The fused ring compound (1-1) of this embodiment can be used as a composition capable of forming a light-emitting device having superior external quantum efficiency by combining with the polymer compound (2-1) and a metal complex. The polymer compound (1-2) of this embodiment can be used as a composition capable of forming a light-emitting device having superior external quantum efficiency by combining with a metal complex.

[0145] As the metal complex, the compound represented by formula (Z) is preferred since it provides a light-emitting device with superior external quantum efficiency. [ka] [In the formula, M 1 represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1represents an integer of 1 or more, and n 2 represents an integer of 0 or more. However, M 1 When is a ruthenium atom, a rhodium atom, or an iridium atom, n 1 +n 2 is 3, and M 1 When n is a palladium atom or a platinum atom, 1 +n 2 is 2. E 1 and E 2 each independently represents a nitrogen atom or a carbon atom. Ring L 1 and ring L 2 each independently represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atom to which they are bonded. A 1 -G 1 -A 2 represents an anionic bidentate ligand. 1 and A 2 Each of G independently represents a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. 1 is a single bond or A 1 and A 2 Together, these represent the atomic groups that constitute a bidentate ligand. In formula (Z), a plurality of symbols may have the same or different meanings.

[0146] In formula (Z), M 1 is preferably an iridium atom. 1 and E 2 is preferably a carbon atom.

[0147] Ring L 1 is a 5- or 6-membered aromatic heterocycle, and these rings may have substituents.

[0148] Ring L 2is preferably a 5- or 6-membered aromatic hydrocarbon ring or a 5- or 6-membered aromatic heterocycle, more preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocycle, and even more preferably a 6-membered aromatic hydrocarbon ring, and these rings may have a substituent. 2 When E is a 6-membered aromatic heterocycle, 2 is preferably a carbon atom.

[0149] Ring L 1 and ring L 2 is preferably a ring constituted by atoms selected from the group consisting of hydrogen atoms, carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms, and a substituent of the ring is preferably constituted by atoms selected from the group consisting of hydrogen atoms, carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

[0150] Ring L 1 and Ring L 2 The ligand composed of is preferably a ligand composed of atoms selected from the group consisting of hydrogen atoms, carbon atoms, nitrogen atoms, and oxygen atoms, and more preferably a ligand composed of hydrogen atoms, carbon atoms, and nitrogen atoms.

[0151] In formula (Z), 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. [ka] [ka] [ka] [In the formula, *M 1 represents the site of binding to R L1 represents a hydrogen atom, an alkyl group, a cycloalkyl 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, or a halogen atom, and these groups may have a substituent.

[0152] Ring L 1 The number of carbon atoms of the aromatic heterocycle represented by the following formula (1) is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15, not including the number of carbon atoms of the substituent. Ring L 1 Examples of the ring include a diazole ring, a triazole ring, a tetrazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, and a diazanaphthalene ring. A pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring, or a diazole ring is preferable, and a pyridine ring, a quinoline ring, an isoquinoline ring, a triazole ring, or a diazole ring is more preferable, and these rings may have a substituent.

[0153] Ring L 2 The number of carbon atoms in the aromatic hydrocarbon ring represented by the following formula (1) 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. 2 Examples of the aromatic hydrocarbon ring represented by the formula (I) include a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, and rings formed by condensing two or more and five or less of these rings. Since the external quantum efficiency of the light-emitting element is more excellent, a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, or a dihydrophenanthrene ring is preferred, a benzene ring, a fluorene ring, or a dihydrophenanthrene ring is more preferred, and a benzene ring is even more preferred, and these rings may have a substituent. Ring L2 The number of carbon atoms of the aromatic heterocycle represented by the following formula (1) is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15, not including the number of carbon atoms of the substituent. 2 Examples of the aromatic heterocycle represented by the formula (I) include a pyrrole ring, a diazole ring, a furan ring, a thiophene ring, a pyridine ring, a diazabenzene ring, and rings in which 1 to 5 aromatic rings are condensed to these rings. Since the external quantum efficiency of the light-emitting device is more excellent, a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, an indole ring, a benzofuran ring, a benzothiophene ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is preferred, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is more preferred, and a pyridine ring, a dibenzofuran ring, or a dibenzothiophene ring is even more preferred, and these rings may have a substituent. Ring L 2 is preferably a benzene ring, a fluorene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring, since the external quantum efficiency of the light-emitting element is further improved, more preferably a benzene ring, a pyridine ring, a dibenzofuran ring, or a dibenzothiophene ring, and further preferably a benzene ring, and these rings may have a substituent.

[0154] Ring L 1 and ring L 2 The substituent that may be substituted 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, still more preferably an alkyl group, an aryl group, or a monovalent heterocyclic group, and particularly preferably an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent.

[0155] Ring L 1 and ring L2 The aryl group in the substituent which may be present is preferably a phenyl group, a naphthyl group, a phenanthrenyl group, a dihydrophenantrenyl group or a fluorenyl group, more preferably a phenyl group or a fluorenyl group, and even more preferably a phenyl group, and these groups may have a substituent. Ring L 1 and ring L 2 The monovalent heterocyclic group in the substituent which may be contained in the ring is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group, or a phenothiazinyl group, more preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group, and even more preferably a pyridyl group, a pyrimidinyl group, or a triazinyl group, and these groups may have a substituent. Ring L 1 and ring L 2 In the substituted amino group in the substituent that may be possessed by ring L, the substituent that the amino group has 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 in the substituent that the amino group has are as follows: 1 and ring L 2 Examples and preferred ranges of the aryl group in the substituent that may be possessed by the amino group are the same as those of the monovalent heterocyclic group in the ring L. 1 and ring L 2 The examples and preferred range of the monovalent heterocyclic group in the substituent that may be possessed by are the same as those of the monovalent heterocyclic group.

[0156] Ring L 1 and ring L 2The substituent that the optionally substituted group may further have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, or an aryl group, and even more preferably an alkyl group. These groups may further have a substituent.

[0157] Ring L 1 and ring L 2 The aryl group, monovalent heterocyclic group or substituted amino group in the substituent that may be possessed by the group is preferably a group represented by formula (DA), formula (DB) or formula (DC), more preferably a group represented by formula (DA) or formula (DB), since the external quantum efficiency of the light-emitting device is more excellent.

[0158] Ring L 1 and ring L 2 At least one ring among these preferably has a group represented by formula (DA), formula (DB) or formula (DC) as a substituent, and more preferably has a group represented by formula (DA) or formula (DB) as a substituent.

[0159] [ka] [In the formula, m DA1 , m DA2 and m DA3 each independently represents an integer of 0 or greater. G DA represents a nitrogen atom, 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. DA1 , Ar DA2 and Ar DA3 When there are multiple, they may be the same or different. T DArepresents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. DA may be the same or different.]

[0160] [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 greater. 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 there are multiple, 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.]

[0161] [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, and these groups may have a substituent. Ar DA1 When there are multiple, 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.]

[0162] m DA1 , m DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 is usually an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, and even more preferably 0 or 1. DA2 , m DA3 , m DA4 , m DA5 , m DA6 and m DA7 are preferably the same integer.

[0163] 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. G DA The substituent that may be contained in the alkyl group is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, or a cycloalkoxy group, and even more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent. G DA is preferably a group represented by formula (GDA-11) to formula (GDA-15), more preferably a group represented by formula (GDA-11) to formula (GDA-14), and even more preferably a group represented by formula (GDA-11) or formula (GDA-14). [ka] [In the formula, * denotes Ar in formula (DA). DA1 Or, Ar in formula (DB) DA1 , Ar DA2 , or Ar DA3 Represents a bond with. ** indicates Ar in formula (DA). DA2 Or, Ar in formula (DB) DA2 , Ar DA4 , or Ar DA6 Represents a bond with. *** represents Ar in formula (DA). DA3 Or, Ar in formula (DB) DA3 , Ar DA5 , or Ar DA7 Represents a bond with. R DA R represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. DA When there are multiple, they may be the same or different.

[0164] R DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups may have a substituent.

[0165] Ar DA1 , Ar DA2 , Ar DA3 , Ar DA4 , Ar DA5 , Ar DA6 and Ar DA7is preferably a phenylene group, a fluorenediyl group, or a carbazolediyl group, more preferably a group represented by formulae (ArDA-1) to (ArDA-5), still more preferably a group represented by formulae (ArDA-1) to (ArDA-3), and particularly preferably a group represented by formula (ArDA-2), and these groups may have a substituent. [ka] [In the formula, R DA has the same meaning as above. R DB R represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. DB When there are multiple, they may be the same or different.

[0166] R DB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent.

[0167] 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.

[0168] T DA is preferably a group represented by formula (TDA-1) to formula (TDA-3), and more preferably a group represented by formula (TDA-1). [ka] [In the formula, R DA and RDB has the same meaning as above.]

[0169] The group represented by formula (DA) is preferably a group represented by formula (D-A1) to formula (D-A5), more preferably a group represented by formula (D-A1) or formula (D-A3) to formula (D-A5), and even more preferably a group represented by formula (D-A1), formula (D-A3) or formula (D-A5). [ka] [In the formula, R p1 , R p2 , R p3 and R p4 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 , R p2 and R p4 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. A plurality of np1 may be the same or different.]

[0170] The group represented by formula (DB) is preferably a group represented by formulae (D-B1) to (D-B3), and more preferably a group represented by formula (D-B1). [ka] [In the formula, R p1 , R p2 and R p3 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p1 and R p2 When there are multiple, they may be the same or different. np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. When there are a plurality of np1 and a plurality of np2, they may be the same or different.]

[0171] The group represented by formula (DC) is preferably a group represented by formulae (D-C1) to (D-C4), more preferably a group represented by formulae (D-C1) to (D-C3), still more preferably a group represented by formula (D-C1) or formula (D-C2), and particularly preferably a group represented by formula (D-C1). [ka] [In the formula, R p4 , R p5 and R p6 R each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. p4 , R p5 and R p6 When there are multiple, they may be the same or different. np4 represents an integer from 0 to 4, np5 represents an integer from 0 to 5, and np6 represents an integer from 0 to 5.

[0172] np1 is preferably an integer of 0 to 2, more preferably 0 or 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0. np4 is preferably an integer of 0 to 2, more preferably 0. np5 is preferably an integer of 0 to 3, more preferably 0 or 1. np6 is preferably an integer of 0 to 2, more preferably 0 or 1.

[0173] R p1 , R p2 , R p3 , R p4 , R p5 and R p6The alkyl group or cycloalkyl group in is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a cyclohexyl group or a tert-octyl group.

[0174] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 The alkoxy group or cycloalkoxy group in is preferably a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group.

[0175] R p1 , R p2 , R p3 , R p4 , R p5 and R p6 is preferably an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent, more preferably an alkyl group which may have a substituent, and even more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group.

[0176] Ring L 1 When there are a plurality of substituents that may be possessed by Ring L, it is preferable that they are not bonded to each other to form a ring together with the atom to which they are bonded. 2 When there are a plurality of substituents that may be possessed by Ring L, it is preferable that they are not bonded to each other to form a ring together with the atom to which they are bonded. 1 and the ring L 2 It is preferred that the substituents which may be possessed by the group R1 and R2 do not bond to each other to form a ring together with the atoms to which they are bonded.

[0177] The metal complex represented by formula (Z) is preferably a metal complex represented by formula (Z-1) since the metal complex has a higher external quantum efficiency than the metal complex represented by formula (Z). [ka]

[0178] M 1 , n 1 , n 2 , E 1 and A 1 -G 1 -A 2 has the same meaning as above. Ring L 1A represents a 5- or 6-membered aromatic heterocycle. Ring L 1A is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring, or a diazole ring, since the external quantum efficiency of the light-emitting element is more excellent, more preferably a pyridine ring, a quinoline ring, an isoquinoline ring, a triazole ring, or a diazole ring, even more preferably a pyridine ring, a quinoline ring, or an isoquinoline ring, and particularly preferably a pyridine ring, and these rings may have a substituent. Ring L 1A Examples of the substituents which may be possessed by the ring L and the preferred range thereof are as follows: 1 and ring L 2 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. Ring L 1A When there are a plurality of optional substituents, it is preferred that they are not bonded to each other (do not form a ring).

[0179] E 21A , E 22A , E 23A and E 24A Each of E independently represents a nitrogen atom or a carbon atom. 21A , E 22A , E 23A and E 24A When multiple are present, they may be the same or different. 21A When is a nitrogen atom, R 21A does not exist. 22A When is a nitrogen atom, R 22A does not exist. 23A When is a nitrogen atom, R 23A does not exist.24A When is a nitrogen atom, R 24A does not exist. R 21A , R 22A , R 23A and R 24A R each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. 21A , R 22A , R 23A and R 24A When multiple R are present, they may be the same or different. 21A and R 22A , R 22A and R 23A , R 23A and R 24A , and ring L 1A The substituents that may be present on R 21A may be bonded to each other to form a ring together with the atoms to which they are bonded. Ring L 2A represents a benzene ring, a pyridine ring or a diazabenzene ring.

[0180] The metal complex represented by formula (Z-1) is preferably a metal complex represented by formulas (1-Z1) to (1-Z10), more preferably a metal complex represented by formulas (1-Z6) to (1-Z10), and further preferably a metal complex represented by formula (1-Z6). [ka] [ka] [In the formula, M 1 , n 1 , n 2 , R 11A , R 12A , R 13A , R 21A , R 22A , R 23A , R24A and A 1 -G 1 -A 2 has the same meaning as above.]

[0181] R 11B , R 12B , R 13B , R 14B , R 15B , R 16B , R 17B and R 18B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since this results in a more excellent external quantum efficiency of the light-emitting element, and is more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent.

[0182] In formula (1-Z1), formula (1-Z3), formula (1-Z4) and formula (1-Z5), R 11A is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent. In formula (1-Z3) and formula (1-Z4), R 12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or an aryl group, even more preferably a hydrogen atom or an alkyl group, and particularly preferably a tertiary alkyl group, and these groups may have a substituent.

[0183] In formula (1-Z2) and formula (1-Z5), R 12A is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group, and these groups may have a substituent. In formula (1-Z5), R 11Ais preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or an aryl group, and even more preferably a hydrogen atom, and these groups may have a substituent.

[0184] In formula (1-Z1), formula (1-Z2), formula (1-Z4) and formula (1-Z5), R 13A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, more preferably a hydrogen atom, an alkyl group, or an aryl group, and even more preferably an aryl group, and these groups may have a substituent.

[0185] R 11A ~R 13A Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in 1 and ring L 2 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group. R 11A ~R 13A Examples of the substituents which may be possessed by the ring L and the preferred range thereof are as follows: 1 and ring L 2 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.

[0186] In formulas (1-Z1) to (1-Z4), R 11A and R 12A , R 12A and R 13A , and R 11A and R 21A are preferably not bonded to each other (do not form a ring).

[0187] In formula (1-Z6), R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , and R 11B and R21A may be bonded to each other to form a ring together with the atom to which each is bonded. 13B and R 14B , R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 11B and R 12B , R 12B and R 13B , R 11B and R 21A , R 13B and R 14B , R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 18B and R 21A may be bonded to each other to form a ring together with the atom to which they are bonded. 11B and R 18B , R 14B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11B and R 21A may be bonded to each other to form a ring together with the atom to which each is bonded. 11B and R 12B , R 12B and R 18B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , and R 11Band R 21A may be bonded to each other to form a ring together with the atoms to which they are bonded. R 11B ~R 18B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since this results in a more excellent external quantum efficiency of the light-emitting element, and is more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent.

[0188] R 11B and R 14B ~R 18B is preferably a hydrogen atom since this facilitates the synthesis of the metal complex, and these groups may have a substituent. R 12B is preferably a hydrogen atom, and these groups may have a substituent. R 13B is preferably a group represented by a hydrogen atom, and these groups may have a substituent.

[0189] R 11B ~R 18B Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in 1 and ring L 2 The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by are the same as those of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that may be possessed by the alkyl group. R 11B ~R 18B Examples of the substituents which may be possessed by the ring L and the preferred range thereof are as follows: 1 and ring L 2 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.

[0190] In formulas (1-Z6) to (1-Z10), R 11B and R 12B , R 12B and R 13B , R 13B and R 14B , R 11B and R 21A, R 13B and R 15B , R 15B and R 16B , R 16B and R 17B , R 17B and R 18B , R 18B and R 21A , R 11B and R 18B , R 14B and R 15B , and R 12B and R 18B It is preferred that they do not bond to each other to form a ring with the atoms to which they are each bonded.

[0191] Examples of the metal complex represented by formula (Z) include metal complexes represented by formulae (Ir-1) to (Ir-34). [ka] [ka] [ka] [ka] [In the formula, Z 1 represents a group represented by formula (DA), formula (DB) or formula (DC). 1 may be the same or different. R L5 R is an alkyl group, a cycloalkyl group, a halogen atom, an aryl group, a 1,3,5-triazinyl group having aryl groups as substituents at the 2- and 4-positions, a group represented by formula (DA), a group represented by formula (DB), or a group represented by formula (DC). L5 When multiple are present, they may be the same or different.

[0192] In formulas (Ir-1) to (Ir-34), RL5 is preferably a group represented by any one of formulae (II-01) to (II-22) in Group II.

[0193] <Group II> [ka] [ka] [ka]

[0194] In formulas (Ir-1) to (Ir-34), R L5 is preferably a group represented by any one of formulas (II-16) to (II-22).

[0195] Examples of the metal complex represented by formula (Z) include metal complexes represented by formulae (Ir-35) to (Ir-43). [ka] [ka] [ka] [In the formula, Z 2 represents a group represented by formula (DA), formula (DB) or formula (DC). 2 may be the same or different. R L6 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. L6 may be the same or different. R L7represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. L7 may be the same or different.]

[0196] Examples of the metal complex represented by formula (Z) include metal complexes represented by the following formula: [ka] [ka] [ka] [ka] [ka]

[0197] Phosphorescent transition metal complexes are available from Aldrich, Luminescence Technology Corp., American Dye Source, and others. In addition, it is also possible to produce the compound by a known method described in documents such as "Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)", "Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984)", JP-T-2004-530254, JP-A-2008-179617, JP-A-2011-105701, JP-T-2007-504272, WO 2006 / 121811, JP-A-2013-147450, and JP-A-2014-224101.

[0198] In the present embodiment, the metal complexes may be used alone or in combination of two or more kinds.

[0199] The metal complex represented by formula (Z) may have multiple geometric isomers, and any geometric isomer may be used. However, since the external quantum efficiency of the light-emitting device 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 %.

[0200] <Metal Complex Manufacturing Method> ·Manufacturing method 1 The metal complex can be produced, for example, by reacting a compound serving as a ligand with a metal compound. If necessary, a functional group conversion reaction of the ligand of the metal complex may be carried out.

[0201] The compound represented by formula (Z) can be prepared, for example, by reacting a compound represented by formula (MM-1) with an iridium compound or a hydrate thereof in step A, and reacting a metal complex represented by formula (MM-2) with a compound represented by formula (MM-1) or a hydrate thereof in step B. 1 -G 1 -A 2 and (B) reacting a precursor of a ligand represented by the following formula (I): [ka] [In the formula, E 1 , E 2 , ring L 1 , ring L 2 and M 1 has the same meaning as above.]

[0202] In step A, 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.

[0203] Step A and Step B 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 (THF), 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; acetone, dimethyl sulfoxide, and water.

[0204] In step A and step B, 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.

[0205] In step A, the compound represented by formula (MM-1) is usually used in an amount of 2 to 20 moles per mole of the iridium compound or a hydrate thereof.

[0206] In step B, a compound represented by formula (MM-1) or A 1 -G 1 -A 2 The amount of the precursor of the ligand represented by the formula (MM-2) is usually 1 to 100 mol per 1 mol of the metal complex represented by the formula (MM-2).

[0207] In step B, the reaction is preferably carried out in the presence of a silver compound such as silver trifluoromethanesulfonate. When a silver compound is used, the amount thereof is usually 2 to 20 moles per mole of the metal complex represented by formula (MM-2).

[0208] The compound represented by formula (MM-1) can be synthesized, for example, by subjecting a compound represented by formula (MM-3) and a compound represented by formula (9) to a coupling reaction such as Suzuki reaction, Kumada reaction, Stille reaction, or Negishi reaction. [ka] [In the formula, E 1 , E 2 , ring L 1 and ring L 2 has the same meaning as above. W 1 and W 2 are each independently -B(OR W1 ) 2 R represents a group represented by the formula (I), 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. 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.

[0209] -B(OR W1 ) 2 Examples of the group represented by the formula include groups represented by the formulae (W-1) to (W-10). [ka]

[0210] W 1 and W 2 Examples of the alkylsulfonyloxy group represented by the formula (I) include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group. 1 and W 2 Examples of the arylsulfonyloxy group represented by the following formula include a p-toluenesulfonyloxy group.

[0211] W 1 and W 2is preferably -B(OR W1 ) 2 A group represented by the formula (W-7): a trifluoromethanesulfonyloxy group, a bromine atom or an iodine atom.

[0212] These reactions are usually carried out in a solvent. The solvent, reaction time and reaction temperature are the same as those described in Step A and Step B. In these reactions, the amount of the compound represented by formula (9) is usually 0.05 to 20 mol per 1 mol of the compound represented by formula (MM-3).

[0213] In the coupling reaction, a catalyst such as a palladium catalyst may be used to promote the reaction. Examples of the palladium catalyst include palladium acetate, bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), and tris(dibenzylideneacetone)dipalladium(0). The palladium catalyst may be used in combination with a phosphorus compound such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, or 1,1'-bis(diphenylphosphino)ferrocene.

[0214] When a palladium catalyst is used in the coupling reaction, the amount thereof is usually an effective amount, for example, per 1 mole of the compound represented by Formula (MM-3), and preferably 0.00001 to 10 moles in terms of palladium element. In the coupling reaction, a base is used in combination, if necessary.

[0215] The compounds, catalysts and solvents used in the reactions explained in <Method for Producing Metal Complex> may each be used alone or in combination of two or more kinds.

[0216] <Composition> In the composition of this embodiment, there are present a structure (1-2-a) obtained by removing one or more hydrogen atoms from a fused ring compound (1-1) and a structure (Y) represented by the formula (Y). In the composition of this embodiment, the structure (1-2-a) may be present as a partial structure in the fused ring compound (1-1), and the structure (1-2-a) may be present as a structural unit in the polymer compound (1-2). In addition, in the composition of this embodiment, the structure (Y) may be present as a structural unit in the polymer compound (1-2), and the structure (Y) may be present as a structural unit in the polymer compound (2-1).

[0217] That is, the composition of the present embodiment contains at least one selected from the group consisting of fused ring compounds (1-1) and polymer compounds (1-2), and also contains a polymer compound having a structural unit (Y).

[0218] The amount of the structure (1-2-a) present in the composition of the present embodiment is preferably 0.01 to 50 mass%, more preferably 0.1 to 30 mass%, still more preferably 0.1 to 10 mass%, and particularly preferably 0.5 to 5 mass%, based on the total amount of the composition.

[0219] The amount of the structure (Y) present in the composition of the present embodiment is preferably 30 to 99.9 mass %, more preferably 60 to 99 mass %, and even more preferably 80 to 99 mass %, based on the total amount of the composition.

[0220] The composition of the present embodiment preferably further contains the above-mentioned metal complex.

[0221] The content of the metal complex in the composition of the present embodiment is preferably 1 to 70 mass %, more preferably 10 to 60 mass %, and even more preferably 15 to 50 mass %, based on the total amount of the composition.

[0222] When the composition of the present embodiment contains a metal complex, efficient energy transfer from the metal complex to the compound having the structure (1-2-a) can be achieved, thereby making it possible to realize a light-emitting device with even more excellent external quantum efficiency. The value of the energy level of the lowest triplet excited state of the metal complex is T P (eV), the value of the energy level of the lowest triplet excited state of the compound represented by formula (1) (fused ring compound (1-1)) or the polymer compound (1-2) is T F (eV), T P and T F Since the external quantum efficiency of the light-emitting device is excellent, it is preferable that formula (A) is satisfied. |T P |≧|T F |···(A)

[0223] The value of the energy level of the lowest singlet excited state of the compound represented by formula (1) (condensed ring compound (1-1)) or the polymer compound (1-2) is expressed as S F (eV), T P and S F Since the external quantum efficiency of the light-emitting device is excellent, it is preferable that formula (B) is satisfied. |T P |≧|S F |···(B)

[0224] A first embodiment of the composition of the present embodiment is a composition containing a fused ring compound (1-1) and a polymer compound (2-1), a second embodiment is a composition containing a polymer compound (1-2) and a polymer compound (2-1), and a third embodiment is a composition containing a polymer compound (1-2) having a structural unit (Y).

[0225] In the first embodiment, the content of the fused ring compound (1-1) is preferably 0.01 to 50 mass%, more preferably 0.1 to 30 mass%, still more preferably 0.1 to 10 mass%, and particularly preferably 0.5 to 5 mass%, based on the total amount of the composition.

[0226] In the first embodiment, the content of the polymer compound (2-1) is, based on the total amount of the composition, preferably 50 to 99.99 mass%, more preferably 70 to 99.9 mass%, even more preferably 90 to 99.9 mass%, and particularly preferably 95 to 99.5 mass%, when the composition does not contain a metal complex; and preferably 50 to 99 mass%, more preferably 50 to 90 mass%, and even more preferably 50 to 85 mass%, when the composition contains a metal complex.

[0227] In the second embodiment, the content of the polymer compound (1-2) is preferably 10 to 98 mass%, more preferably 20 to 98 mass%, even more preferably 30 to 95 mass%, and particularly preferably 50 to 80 mass%, based on the total amount of the composition.

[0228] In the second embodiment, the content of the polymer compound (2-1) is preferably 2 to 90 mass %, more preferably 2 to 80 mass %, still more preferably 5 to 70 mass %, and particularly preferably 20 to 50 mass %, based on the total amount of the composition.

[0229] In the third embodiment, the content of the polymer compound (2-1) is, based on the total amount of the composition, preferably 50 to 100 mass%, more preferably 70 to 100 mass%, even more preferably 90 to 100 mass%, and particularly preferably 95 to 100 mass%, when the composition does not contain a metal complex; and preferably 50 to 99.9 mass%, more preferably 50 to 90 mass%, and even more preferably 50 to 85 mass%, when the composition contains a metal complex.

[0230] As the composition of the first type, for example, the composition shown in Table 3 can be mentioned.

[0231] [Table 3] [In the table, t, u, v, and w represent the mass ratio of each component. t+u+v+w=100, and 70≦t+u+v≦100. The other components refer to components other than the fused ring compound (1-1), the polymer compound (2-1), and the metal complex.]

[0232] Examples of the second and third embodiments include the compositions shown in Table 4.

[0233] [Table 4] [In the table, t', u', v', and w' represent the mass ratio of each component. t'+u'+v'+w'=100, and 70≦t'+u'+v'≦100. Other components refer to components other than the polymer compound (1-2), the polymer compound (2-1), and the metal complex.]

[0234] In the second embodiment (a composition containing a polymer compound (1-2) and a polymer compound (2-1)), the number of moles of the structural unit (1-2-a) contained in the polymer compound (1-2) is preferably 0.01 to 50%, more preferably 0.1 to 30%, even more preferably 0.5 to 15%, and particularly preferably 0.5 to 5%, based on the total number of moles of the structural units of the polymer compound (1-2) and the polymer compound (2-1).

[0235] In the third embodiment (a composition containing a polymer compound (1-2) having a structural unit (Y)), the number of moles of the structural unit (1-2-a) contained in the polymer compound (1-2) is preferably 0.01 to 50%, more preferably 0.1 to 30%, even more preferably 0.5 to 15%, and particularly preferably 0.5 to 5%, based on the total number of moles of the structural units of the polymer compound (1-2). The number of moles of the structural unit (Y) contained in the polymer compound (1-2) is preferably 50 to 99.9%, more preferably 70 to 99.8%, even more preferably 85 to 99.5%, and particularly preferably 95 to 99.5%, based on the total number of moles of the structural units of the polymer compound (1-2).

[0236] The composition of the present embodiment may further contain at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent.

[0237] [Hole transport material] The hole transport material is classified into a low molecular weight compound and a high molecular weight compound, and the high molecular weight compound is preferred. The hole transport material is more preferably a compound having a crosslinking group (crosslinking material). The crosslinking material is preferably a low molecular weight compound having at least one crosslinking group selected from the crosslinking group A group, or a high molecular weight compound containing a crosslinking structural unit having at least one crosslinking group selected from the crosslinking group A group.

[0238] Examples of the polymeric compound include polyvinylcarbazole and its derivatives; polyarylenes having an aromatic amine structure in the side chain or main chain and its derivatives. The polymeric compound may be a compound to which an electron-accepting moiety is bonded. Examples of the electron-accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, etc., and fullerene is preferred.

[0239] In the composition of the present embodiment, 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 total amount of the fused ring compound (1-1), the polymer compound (1-2), the polymer compound (2-1), and the metal complex in the composition.

[0240] The hole transport material may be used alone or in combination of two or more kinds.

[0241] [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.

[0242] Examples of low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone, as well as derivatives thereof.

[0243] Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

[0244] In the composition of the present embodiment, 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 total amount of the fused ring compound (1-1), the polymer compound (1-2), the polymer compound (2-1), and the metal complex in the composition.

[0245] The electron transporting materials may be used alone or in combination of two or more kinds.

[0246] [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.

[0247] Examples of low molecular weight compounds include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.

[0248] Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, and polyquinoxaline, as well as derivatives thereof; and conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain.

[0249] In the composition of the present embodiment, the amount of the hole injection material and the electron injection material is usually 1 to 400 parts by mass, and preferably 5 to 150 parts by mass, per 100 parts by mass of the total amount of the fused ring compound (1-1), the polymer compound (1-2), the polymer compound (2-1), and the metal complex in the composition.

[0250] The hole injection material and the electron injection material may each be used alone or in combination of two or more kinds.

[0251] [Ion doping] When the hole injection material 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.

[0252] 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.

[0253] The doping ions may be of one type or two or more types.

[0254] [Luminescent materials] The light-emitting materials are classified into low molecular weight compounds and high molecular weight compounds. The light-emitting materials may have a crosslinking group.

[0255] Examples of low molecular weight compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triplet luminescent complexes having iridium, platinum, or europium as a central metal.

[0256] Examples of the polymer compound include polymer compounds containing a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a carbazolediyl group, a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, and the like.

[0257] 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.

[0258] In the composition of the present embodiment, the content of the light-emitting material is usually 0.1 to 400 parts by mass per 100 parts by mass of the total amount of the fused ring compound (1-1), the polymer compound (1-2), the polymer compound (2-1), and the metal complex in the composition.

[0259] [Antioxidants] The antioxidant may be any compound that is soluble in the same solvent as the polymer compound of this embodiment and does not inhibit light emission and charge transport, and examples of such antioxidants include phenol-based antioxidants and phosphorus-based antioxidants.

[0260] In the composition of the present embodiment, the amount of the antioxidant is usually 0.001 to 10 parts by mass per 100 parts by mass of the total amount of the fused ring compound (1-1), the polymer compound (1-2), the polymer compound (2-1), and the metal complex in the composition.

[0261] The antioxidants may be used alone or in combination of two or more kinds.

[0262] <Ink> The composition of the present embodiment may contain a solvent. Hereinafter, a composition containing a solvent will be referred to as "ink."

[0263] The ink of the present embodiment can be suitably used for coating methods such as 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, and nozzle coating.

[0264] The viscosity of the ink in this embodiment may be adjusted depending on the type of application 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 mPa s to 30 mPa s at 25°C, since clogging and deflection during discharge are less likely to occur.

[0265] The solvent contained in the ink of this embodiment 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; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane, n-dodecane, and bicyclohexyl. Examples of the solvent include aliphatic hydrocarbon solvents such as acetone, methyl ethyl ketone, cyclohexanone, acetophenone, and the like; ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, phenyl acetate, and the like; polyhydric alcohol solvents such as ethylene glycol, glycerin, 1,2-hexanediol, and the like; alcohol solvents such as isopropyl alcohol, cyclohexanol, and the like; sulfoxide solvents such as dimethyl sulfoxide, and the like; and amide solvents such as N-methyl-2-pyrrolidone, N,N-dimethylformamide, and the like. The solvents may be used alone or in combination of two or more kinds.

[0266] In the ink of this embodiment, the amount of the solvent is usually 1,000 to 100,000 parts by mass, and preferably 2,000 to 20,000 parts by mass, per 100 parts by mass of the total amount of the fused ring compound (1-1), polymer compound (1-2), polymer compound (2-1), and metal complex in the composition.

[0267] <Membrane> The film contains the composition of the present embodiment.

[0268] The film is suitable as a light-emitting layer in a light-emitting device.

[0269] The film can be produced 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.

[0270] The thickness of the film is usually from 1 nm to 10 μm.

[0271] <Light emitting element> The light-emitting device of this embodiment is a light-emitting device containing the composition of this embodiment. The light-emitting device of this embodiment has, for example, electrodes consisting of an anode and a cathode, and a layer containing the composition of this embodiment provided between the electrodes.

[0272] [Layer composition] The layer containing the composition of the present embodiment is usually one or more of the following layers: a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer, and an electron-injecting layer, and is preferably a light-emitting layer. Each of these layers contains a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. Each of these layers can be formed by dissolving the light-emitting material, the hole-transporting material, the hole-injecting material, the electron-transporting material, and the electron-injecting material in the above-mentioned solvent, preparing an ink, and using the ink, using the same method as for producing the above-mentioned film.

[0273] 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.

[0274] Examples of materials for the hole transport layer, electron transport layer, light-emitting layer, hole injection layer, and electron injection layer include the composition of the present embodiment as well as the hole transport material, electron transport material, light-emitting material, hole injection material, and electron injection material described above, respectively.

[0275] 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.

[0276] In the light-emitting element of the present embodiment, examples of the method 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. When a high molecular weight compound is used, examples of the method include a method of film formation from a solution or molten state.

[0277] The order, number and thickness of the layers to be laminated are adjusted taking into consideration the external quantum efficiency and luminance life.

[0278] [Substrate / electrode] The substrate in the light-emitting element may be any substrate on which an electrode can be formed and which is not chemically changed when an organic layer is formed, and may be made of a material 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.

[0279] Examples of materials for the anode include conductive metal oxides and translucent metals, and preferably include indium oxide, zinc oxide, and tin oxide; conductive compounds such as indium tin oxide (ITO) and indium zinc oxide; a composite of silver, palladium, and copper (APC); NESA, gold, platinum, silver, and copper.

[0280] Examples of the cathode material include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of these metals; alloys of one or more of these metals with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys. The anode and the cathode may each have a laminated structure of two or more layers.

[0281] [Application] The light-emitting device of this embodiment is useful for displays, lighting, and the like. EXAMPLES

[0282] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0283] In the examples, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. The SEC measurement conditions were as follows:

[0284] <Measurement conditions> The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into the SEC. The mobile phase was run at a flow rate of 0.6 mL / min. The columns used were a TSKguardcolumn SuperAW-H, a TSKgel Super AWM-H, and a TSKgel SuperAW3000 (all manufactured by Tosoh) connected in series. The detector used was a UV-VIS detector (manufactured by Tosoh, product name: UV-8320GPC).

[0285] 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).

[0286] <Synthesis of compound HTL-1> The compound HTL-1 used was synthesized according to the method described in JP-A-2011-174062. Compound HTL-1 is a copolymer composed of a structural unit derived from compound S1, a structural unit derived from compound S2, and a structural unit derived from compound S3 in a molar ratio of 50:42.5:7.5. [ka]

[0287] <Synthesis of compound P1> Compound P1 was synthesized according to the method described in JP 2012-036388 A. Compound P1 is a copolymer composed of a structural unit derived from compound S1, a structural unit derived from compound S4, and a structural unit derived from compound S5 in a molar ratio of 50:26:24. [ka]

[0288] <Synthesis of compound P2> [ka] Compound S6 used was synthesized according to the method described in International Publication No. 2012 / 86671. Compound S7 used was synthesized according to the method described in International Publication No. 2009 / 131255. After the inside of the reaction vessel was filled with an inert gas atmosphere, compound S1 (1.519 g, 3.05 mmol), compound S6 (1.454 g, 2.26 mmol), compound S7 (0.387 g, 0.61 mmol), compound S2 (0.101 g, 0.18 mmol), palladium acetate (1.0 mg), tris-o-methoxyphenylphosphine (6.4 mg), 20 mass% tetraethylammonium hydroxide aqueous solution (10.8 g), and toluene (41 g) were added and stirred under reflux for 4 hours. Then, phenylboronic acid (37.2 mg) was charged and stirred under reflux for 8 hours. Then, an aqueous solution of sodium diethyldithiacarbamate was added and stirred at 85 ° C. for 2 hours. The oil layer was separated from the aqueous layer, washed with water and 3 mass% acetic acid water, and then passed through an alumina column and a silica gel column, and the obtained oil layer was dropped into methanol to obtain a precipitate. The precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain a number average molecular weight of Mn = 6.4 × 10 4 , weight average molecular weight Mw=1.4×10 5 Compound P2 was obtained.

[0289] <Compound M1> Compound M1 was purchased from AK Scientific. [ka]

[0290] <Synthesis of compound M2> Compound M2 was synthesized according to the method described in WO 2007 / 058368. [ka]

[0291] <Synthesis of compound MC-1> Compound MC-1 was synthesized according to the method described in JP 2013-147551 A, and the compound showed an HPLC area percentage value of 99.5% or more was used. [ka]

[0292] <Synthesis of compound MC-2> Compound MC-2 was synthesized according to the method described in International Publication No. 2009 / 131255, and the compound showed an HPLC area percentage value of 99.5% or more was used. [ka]

[0293] <Synthesis of Compound D1> Compound D1 was synthesized according to the method described in International Publication No. 2020 / 080528. [ka]

[0294] <Synthesis of compound S8> Compound S8 was synthesized in the following manner. [ka] After the inside of the reaction vessel was conditioned under nitrogen, picolinic acid (739 mg, 6.0 mmol), 3,5-dibromo-tert-butylbenzene (8.8 g, 30 mmol), potassium phosphate (8.1 g, 38 mmol), 3-chlorophenol (1.9 g, 15 mmol), and N-methylpyrrolidone (80 mL) were added and stirred at 130° C. for 40 hours. After cooling to room temperature, toluene (200 mL) and 1N aqueous hydrochloric acid solution (200 mL) were added and stirred. The obtained organic phase was taken out and washed three times with ion-exchanged water (100 mL). The obtained organic phase was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane) to obtain compound S8a (2.9 g, colorless transparent oil). Compound S8a 1 The purity determined by H-NMR measurement was 97% or more. 1 H-NMR (400 MHz, CDCl 3 )δ(ppm)=7.29-7.24(m,2H),7.11-7.09(m,1H),7.01-6.99(m,2H),6.93(t,1H),6.86-6.90(m,1H),1.29(s,9H).

[0295] After the inside of the reaction vessel was conditioned under nitrogen, (2',6'-dimethoxybiphenyl)-dicyclohexylphosphine (82 mg, 0.2 mmol), tris(dibenzylideneacetone)dipalladium(0) (88 mg, 96 μmol), compound S8a (2.8 g, 8.0 mmol), p-toluidine (343 mg, 3.2 mmol), sodium tert-butoxide (769 mg, 8.0 mmol), and toluene (30 mL) were added and stirred at 90°C for 40 hours. After cooling to room temperature, the mixture was filtered through a filter lined with Florisil and washed with toluene. The resulting solution was concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography (mixed solvent of hexane and dichloromethane) to obtain compound S8b (1.4 g, white solid). Compound S8b 1 The purity determined by H-NMR measurement was 97% or more. This procedure was repeated to obtain the required amount of compound S8b. 1 H-NMR (400 MHz, CDCl3 )δ(ppm)=7.18(t,2H),7.05-6.98(m,6H),6.93-6.92(m,4H),6.82(d,2H),6.67(s,2H),6.50(s,2H),2.30(s,3H),1.21(s,18H).

[0296] After the inside of the reaction vessel was conditioned under nitrogen, compound S8b (3.8 g, 6.0 mmol), boron triiodide (9.4 g, 24.0 mmol), and 1,2,4-trichlorobenzene (40 mL) were added and stirred at 180°C for 20 hours. After cooling in an ice bath, dichloromethane and phosphate buffer (pH 6, 250 mL) were added and stirred at 0°C. The resulting aqueous phase was washed three times with dichloromethane (150 mL). All the resulting organic phases were combined and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (mixed solvent of hexane and dichloromethane). The resulting solid was washed four times with acetonitrile (200 mL) to obtain compound S8c (457 mg, yellow solid). Compound S8c 1 The purity determined by H-NMR measurement was 97% or more. 1 H-NMR (400 MHz, CDCl 3 )δ(ppm)=8.48(s,2H),8.36(d,2H),7.95(s,2H),7.54(s,2H),7.29-7.31(m,4H),2.59(s,3H),1.38(s,18H).

[0297] After the inside of the reaction vessel was conditioned with argon gas, compound S8c (145 mg, 0.23 mmol), bis(pinacolato)diboron (196 mg, 0.68 mmol), dimethoxyethane (20 mL), and potassium acetate (134 mg, 1.36 mmol) were added and stirred. Tris(dibenzylideneacetone)dipalladium(0) (5 mg, 0.01 mmol) and dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (12 mg, 0.02 mmol) were added thereto and stirred at 85°C for 18 hours. After cooling to room temperature, toluene was added and the mixture was filtered through a filter covered with silica gel. The obtained filtrate was concentrated. The obtained crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene), recrystallized several times using toluene, acetonitrile, and chlorobenzene, and then dried under reduced pressure at 50° C. to obtain compound S8 (90 mg, yellow solid). The HPLC area percentage value of compound S8 was 98.0%. 1 H-NMR (600MHz, CD 2 Cl 2 -d 2 )δ(ppm)=8.69(s,2H),8.57(d,2H),7.95(s,2H),7.94(s,2H),7.74(d,2H),7.31(s,2H),1.39(s,24H),1.35(s,18H).

[0298] Example 1: Synthesis of compound P3 Compound P3 was synthesized in the following manner. [ka] After making the inside of the reaction vessel an inert gas atmosphere, compound S1 (0.5056 g, 1.01 mmol), compound S8 (0.0179 g, 0.02 mmol), compound S4 (0.4725 g, 0.55 mmol), compound S5 (0.4311 g, 0.51 mmol), bis(tris-o-methoxyphenylphosphine)dichloropalladium (0.9 mg), methyltrioctylammonium chloride (0.04 g), 17.5 mass% aqueous sodium carbonate solution (20 g), and toluene (24 g) were added, and the mixture was stirred under reflux for 9 hours. Next, phenylboronic acid (51.9 mg) was charged, and the mixture was stirred under reflux for 5 hours. Next, an aqueous sodium diethyldithiocarbamate solution was added, and the mixture was stirred at 85 °C for 2 hours. The oil layer was separated from the aqueous layer, washed with water and 3 mass% aqueous acetic acid, then passed through an alumina column and a silica gel column, and the obtained oil layer was dropped into methanol to obtain a precipitate. The precipitate was filtered, washed with methanol, and dried under reduced pressure to obtain a compound P3 with a number average molecular weight Mn = 7.9×10 4 , weight average molecular weight Mw = 32.3×10 4 .

[0299] <Example D1> Fabrication of Light-Emitting Element D1 <ITO Substrate and Hole Injection Layer An anode was formed by forming an ITO film with a thickness of 45 nm on a glass substrate by sputtering. Plexcore (registered trademark) OC AQ-1200, which is a hole injection material, was formed into a film by spin coating (thickness 50 nm), and dried on a hot plate heated to 170 °C for 15 minutes in an air atmosphere. Thereby, a hole injection layer was formed. <Hole Transport Layer Compound HTL-1 was dissolved in xylene at a concentration of 0.9 mass%. Using the obtained xylene solution, a film was formed with a thickness of 30 nm on the hole injection layer, and heated on a hot plate at 200 °C for 30 minutes in a nitrogen gas atmosphere. Thereby, a hole transport layer was formed. <Light-Emitting Layer Compound P2 and compound D1 (compound P2:compound D1=98% by mass:2% by mass) were dissolved in xylene at a concentration of 1.4% by mass. The resulting xylene solution was used to form a film with a thickness of 70 nm on the hole transport layer by spin coating, and heated on a hot plate at 150° C. for 10 minutes in a nitrogen gas atmosphere. This formed an emitting layer. <Cathode formation> The substrate on which the light-emitting layer was formed was placed in the deposition machine and -4 After reducing the pressure to below 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 as a cathode. After the deposition, the substrate on which the cathode was formed was sealed with a glass substrate to produce light-emitting device D1.

[0300] <Light-emitting elements D2 to D4 and light-emitting elements CD1 to CD4> Fabrication of light-emitting elements D2 to D4 and light-emitting elements CD1 to CD4 The light-emitting element D1 was fabricated in the same manner as the light-emitting element D1, except that the materials in Table 5 were used instead of "compound P2 and compound D1 (compound P2:compound D1=98% by mass:2% by mass)."

[0301] Example D5: Preparation of light-emitting element D5 A light-emitting element D5 can be produced in the same manner as the light-emitting element D1, except that in the <light-emitting layer> of the light-emitting element D1, "compound P2 and compound D1 (compound P2: compound D1 = 98% by mass: 2% by mass)" is changed to "compound P3".

[0302] <Examples D6 to D10> Fabrication of Light-Emitting Devices D6 to D10 Light-emitting devices D6 to D10 can be fabricated in the same manner as for light-emitting device D1, except that "compound D1" in the <light-emitting layer> of light-emitting device D1 to D4 and comparative example CD4 is changed to "compound P3."

[0303] Example D11: Preparation of light-emitting element D11 Light-emitting element D11 can be produced in the same manner as light-emitting element D1, except that "compound P2" in the <light-emitting layer> of light-emitting element D1 is changed to "compound P3."

[0304] <Examples D12 to D16> Fabrication of Light-emitting Devices D12 to D16 Light-emitting devices D12 to D16 can be fabricated in the same manner as light-emitting device D1, except that "compound P1" in the <light-emitting layer> of light-emitting devices D2 to D4 and comparative examples CD1 to CD2 is changed to "compound P3", respectively.

[0305] <Light Emitting Characteristics of Light Emitting Device> By applying a voltage to the light-emitting element D1, light emission having a maximum peak in the emission spectrum at 505 nm was observed. The external quantum efficiency was 19.6%, and the CIE1931 color coordinates (x, y) were (0.12, 0.63). The light-emitting elements D2 to D4 and the light-emitting elements CD1 to CD4 were similarly determined for their light-emitting characteristics. The light-emitting characteristics of Examples D5 to D16 can also be determined in the same manner.

[0306] The results of Examples D1 to D4 and Comparative Examples CD1 to CD4 are shown in Table 5.

[0307] [Table 5]

Claims

1. A fused ring compound (1-1) represented by formula (1), A polymer compound (2-1) having a structural unit represented by formula (Y), A composition comprising a metal complex represented by formula (1-Z1): 【Chemistry 1】 [In formula (1), Ring A, ring B and ring C each independently represent an aromatic hydrocarbon ring which may have a substituent. Y １ represents B. X １ represents N. X ２ represents O or N-R'. R' represents an aryl group, a heteroaryl group, an alkyl group or a cycloalkyl group, and these groups may have a substituent. R' may be bonded to ring A and / or ring C via a linking group or a single bond. Some or all of two adjacent A rings may be bonded to each other via a single bond. n is 1 or 2. In formula (1), multiple symbols may be the same or different. When the fused ring compound (1-1) represented by formula (1) has hydrogen atoms, at least one of the hydrogen atoms may be substituted with a deuterium atom, a cyano group, or a halogen atom.] 【Chemistry 2】 [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. 【Chemistry 3】 [In the formula, M 1 represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, or a platinum atom. n 1 represents an integer of 1 or more, and n 2 represents an integer of 0 or more, provided that when M 1 is a ruthenium atom, a rhodium atom or an iridium atom, n 1 +n 2 is 3, and when M 1 is a palladium atom or a platinum atom, n 1 +n 2 is 2. R 11A represents an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. R 13A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. R 21A , R 22A , R 23A and R 24A each independently represent 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 there are a plurality of R 21A , R 22A , R 23A and R 24A , they may be the same or different. R 21A and R 22A , R 22A and R 23A , R 23A and R 24A , and R 11A and R 21A may each be bonded to form a ring together with the atom to which they are bonded. A 1 -G 1 -A 2 represents an anionic bidentate ligand. A 1 and A 2 each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. G 1 represents a single bond or an atomic group constituting a bidentate ligand together with A 1 and A 2 . In formula (1-Z1), multiple symbols may have the same or different meanings.

2. Ar Ｙ１ The composition according to claim 1 , wherein is an optionally substituted phenylene group, an optionally substituted fluorenediyl group, or a group represented by formula (YY): 【Chemistry 4】 [In the formula, Ar ＹＹ１ and Ar ＹＹ３ each independently represents an arylene group which may have a substituent; Ar ＹＹ２ represents a divalent nitrogen-containing aromatic heterocyclic group which may have a substituent.

3. The composition according to claim 1 or 2, further comprising at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent.

4. A light-emitting device comprising the composition according to any one of claims 1 to 3.

5. A light-emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode, The first organic layer comprises the composition according to any one of claims 1 to 3, The light-emitting device according to claim 4 , wherein the second organic layer contains a crosslinked product of a crosslinkable material.

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