JP2023050135A - Composition and light emitting element containing the same - Google Patents

Abstract

An object of the present invention is to provide a composition useful for manufacturing a light-emitting device with a low driving voltage, and to provide a light-emitting device containing the composition.
At least one selected from the group consisting of a metal complex represented by formula (1) and a polymer compound (A), a low-molecular-weight compound (B), and the low-molecular-weight compound (B) At least one selected from the group consisting of a polymer compound (B) containing a structural unit having a group from which one or more hydrogen atoms are removed, a compound represented by formula (H-1), and a polymer compound and at least one selected from the group consisting of
[Selection figure] None

Description

The present disclosure relates to compositions and light emitting devices containing the same.

A light-emitting device such as an organic electroluminescence device can be suitably used for display and lighting applications. As a light-emitting material used for a light-emitting layer of a light-emitting element, for example, Patent Document 1 describes a composition containing a compound H1, a metal complex Firpic, and a compound B1.

WO2020/203209

However, a light-emitting element manufactured using the above composition does not necessarily have a sufficiently low driving voltage.
Accordingly, an object of one embodiment of the present disclosure is to provide a composition useful for manufacturing a light-emitting device with a low driving voltage, and to provide a light-emitting device containing the composition.

The present disclosure provides the following <1> to <13>.

<1> A group consisting of the metal complex represented by the formula (1) and the polymer compound (A) containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by the above formula (1) at least one selected from
A low-molecular-weight compound (B) having a condensed heterocyclic skeleton (b) containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an ^sp3 carbon atom and a nitrogen atom in the ring and at least one selected from the group consisting of a polymer compound (B) containing a structural unit having a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (B),
A compound represented by formula (H-1) and at least one structural unit selected from the group consisting of structural units represented by formula (X) and structural units represented by formula (Y) at least one selected from the group consisting of polymer compounds;
A composition comprising

[In the formula,
M represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
ⁿ¹ represents an integer of 1 or more, and ⁿ² represents an integer of 0 or more. However, n ¹ +n ² is 3 when M is a rhodium atom or an iridium atom, and n ¹ +n ² is 2 when M is a palladium atom or a platinum atom.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. When multiple E ¹ and E ² are present, they may be the same or different.
Ring L ¹ represents an aromatic heterocyclic ring containing a 5-membered ring, and the ring may have a substituent. 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 atoms to which they are bonded. When multiple rings L ¹ are present, they may be the same or different.
Ring ^L2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. 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 atoms to which they are bonded. When there is more than one ring ^L2 , they may be the same or different.
The substituent that ring L ¹ may have and the substituent that ring L ² may have may be the same or different, and are bonded to each other to form a ring together with the atoms to which they are bonded. may be formed.
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 forming a bidentate ligand together with A ¹ and A ² . When multiple A ¹ -G ¹ -A ² are present, they may be the same or different. ]

[In the formula,
Ar ^H1 and Ar ^H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. 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 atoms to which they are bonded.
n ^H1 represents an integer of 0 or more.
L ^H1 represents a divalent group, and the divalent group may have a substituent. 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 atoms to which they are bonded. When multiple L ^H1 are present, they may be the same or different, and they may be directly bonded to each other or bonded via a divalent group to form a ring.
Ar ^H1 and Ar ^H2 may be directly bonded or bonded via a divalent group to form a ring. L ^H1 and Ar ^H1 may be directly bonded or bonded via a divalent group to form a ring. L ^H1 and Ar ^H2 may be directly bonded or bonded via a divalent group to form a ring. ]

[In the formula,
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^{1 X1} and Ar 2 ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.
Ar ^X2 and Ar ^X4 each independently represent 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; and these groups may have a substituent. 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 atoms to which they are bonded. When multiple Ar ^X2 are present, they may be the same or different. When multiple Ar ^X4 are present, they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded. When multiple R ^X2 are present, they may be the same or different. When multiple R ^X3 are present, they may be the same or different. ]

[Wherein, Ar ^Y 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, The group may have a substituent. 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 atoms to which they are bonded. ]
<2> The ring L ² is an aromatic hydrocarbon ring containing a 5- or 6-membered ring, or an aromatic heterocyclic ring containing a 5- or 6-membered ring, and these rings have substituents. The composition according to <1> above.

<3> The ring L ² is a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring, or a monocyclic, bicyclic or tricyclic aromatic heterocyclic ring, The composition according to <1> or <2> above, wherein the ring may have a substituent.
<4> The ring ^L2 is a benzene ring, a fluorene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these rings may have a substituent. > to the composition according to any one of <3>.
<5> The composition according to any one of <1> to <4> above, wherein the ring L ¹ is a diazole ring or a triazole ring, and these rings may have a substituent.
<6> The composition according to any one of <1> to <5>, wherein the ring L ¹ is an optionally substituted triazole ring.
<7> The above <1> to <6>, wherein the condensed heterocyclic skeleton (b) contains a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring. The composition according to any one of
<8> The composition according to any one of <1> to <7>, wherein the condensed heterocyclic skeleton (b) contains a boron atom and a nitrogen atom in the ring.
<9> The low-molecular-weight compound (B) is a compound represented by formula (1-1), a compound represented by formula (1-2), or a compound represented by formula (1-3). The composition according to any one of <1> to <6> above.

[In the formula,
Ar ¹ , Ar ² and Ar ³ each independently represent an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.
Y ¹ represents an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, an alkylene group or a cycloalkylene group, and these groups may have a substituent. 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 atoms to which they are bonded.
Y ² and Y ³ each independently represent a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, a group represented by -B(Ry)-, an alkylene group, It represents a cycloalkylene group, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.
Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded. When two or more Ry are present, they may be the same or different.
Y ¹ and Ar ¹ may be directly bonded or bonded via a divalent group to form a ring. Y ¹ and Ar ² may be directly bonded or bonded via a divalent group to form a ring. Y ² and Ar ¹ may be directly bonded or bonded via a divalent group to form a ring. Y ² and Ar ³ may be directly bonded or bonded via a divalent group to form a ring. Y ³ and Ar ² may be directly bonded or bonded via a divalent group to form a ring. Y ³ and Ar ³ may be directly bonded or bonded via a divalent group to form a ring. ]
<10> The composition according to <9>, wherein Y ¹ , Y ² and Y ³ are an oxygen atom, a sulfur atom or a group represented by -N(Ry)-.
<11> The composition according to <9> or <10>, wherein Y ¹ , Y ² and Y ³ are groups represented by -N(Ry)-.
<12> The above <1> to <11, further containing at least one 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. The composition according to any one of .
<13> A light-emitting element having an anode, a cathode, and an organic layer provided between the anode and the cathode,
A light-emitting device, wherein the organic layer is a layer containing the composition according to any one of <1> to <12>.

According to one embodiment of the present disclosure, it is possible to provide a composition useful for manufacturing a light-emitting device with low driving voltage. Further, according to one embodiment of the present disclosure, a light-emitting device containing the composition can be provided.

Preferred embodiments of the present disclosure are described in detail below.

<Description of common terms>
Terms commonly used in this specification have the following meanings unless otherwise specified.

"Room temperature" means 25°C.
Me is a methyl group, Et is an ethyl group, Bu is a butyl group, i-Pr is an isopropyl group, and t-Bu is a tert-butyl group.
A hydrogen atom may be a deuterium atom or a protium atom.
In the formulas representing the metal complexes, solid lines representing bonds with the central metal mean ionic bonds, covalent bonds or coordinate bonds.

A "low-molecular-weight compound" means a compound having no molecular weight distribution and a molecular weight of 1×10 ⁴ or less.
A "polymer compound" means a polymer having a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1×10 ³ or more (for example, 1×10 ³ to 1×10 ⁸ ).
A "structural unit" means a unit that exists at least one in a polymer compound. Two or more structural units present in a polymer compound are generally called "repeating units".
The polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms.
The terminal group of the polymer compound is preferably a stable group from the viewpoint of the light emitting properties of the light emitting device.
The terminal group of the polymer compound is preferably a group conjugated to the main chain of the polymer compound, for example, an aryl group or 1 valent heterocyclic groups.

The "alkyl group" may be either linear or branched. The number of carbon atoms in the linear alkyl group is generally 1-50, preferably 1-20, more preferably 1-10, not including the number of carbon atoms in the substituents. The number of carbon atoms in the branched alkyl group is usually 3-50, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
The alkyl group may have a substituent. Examples of alkyl groups include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group and heptyl. group, octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group, and hydrogen atoms in these groups Some or all of the groups substituted with substituents (e.g., trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl)propyl group, 3-(3,5-di-hexylphenyl)propyl group and 6-ethyloxyhexyl group).
The number of carbon atoms in the "cycloalkyl group" is usually 3-50, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituents.
A cycloalkyl group may have a substituent. Cycloalkyl groups include, for example, cyclohexyl groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
The number of carbon atoms in the "alkylene group" is generally 1-20, preferably 1-15, more preferably 1-10, not including the number of carbon atoms in the substituents.
The alkylene group may have a substituent. The alkylene group includes, for example, a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, an octylene group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents.
The number of carbon atoms in the "cycloalkylene group" is usually 3 to 20, preferably 4 to 10, more preferably 5 to 7, not including the number of carbon atoms in substituents.
A cycloalkylene group may have a substituent. The cycloalkylene group includes, for example, a cyclohexylene group and a group in which some or all of the hydrogen atoms in the group are substituted with substituents.

“Aromatic hydrocarbon group” means a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. A group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon is also referred to as an "aryl group". A group obtained by removing two hydrogen atoms directly bonded to carbon atoms forming a ring from an aromatic hydrocarbon is also referred to as an "arylene group".
The number of carbon atoms in the aromatic hydrocarbon group is generally 6-60, preferably 6-40, more preferably 6-20, not including the number of carbon atoms in the substituents.
The "aromatic hydrocarbon group" includes, for example, monocyclic aromatic hydrocarbons (e.g., benzene), or polycyclic aromatic hydrocarbons (e.g., naphthalene, indene, naphthoquinone, indenone and tetralone; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenanthoquinone and fluorenone; benzoanthracene, benzophenanthrene and benzofluorene. tetracyclic aromatic hydrocarbons; pentacyclic aromatic hydrocarbons such as dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene ; and seven-ring aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene). mentioned. Aromatic hydrocarbon group is a monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon group in which one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring are removed, and a plurality of groups are bonded. may be The aromatic hydrocarbon group may have a substituent.

An "alkoxy group" may be either linear or branched. The straight-chain alkoxy group usually has 1 to 40 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, not including the carbon atoms of the substituents. The number of carbon atoms in the branched alkoxy group is usually 3-40, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
The alkoxy group may have a substituent. Examples of alkoxy groups include methoxy, ethoxy, isopropyloxy, butyloxy, hexyloxy, 2-ethylhexyloxy, 3,7-dimethyloctyloxy, lauryloxy, and hydrogen in these groups. Groups in which some or all of the atoms are substituted with substituents are included.
The number of carbon atoms in the "cycloalkoxy group" is usually 3-40, preferably 3-20, more preferably 4-10, not including the number of carbon atoms in the substituents.
A cycloalkoxy group may have a substituent. Cycloalkoxy groups include, for example, cyclohexyloxy groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.
The number of carbon atoms in the "aryloxy group" is generally 6-60, preferably 6-40, more preferably 6-20, not including the number of carbon atoms in the substituents.
The aryloxy group may have a substituent. Examples of the aryloxy group include phenoxy group, naphthyloxy group, anthracenyloxy group, pyrenyloxy group, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.

A “heterocyclic group” means a group obtained by removing one or more hydrogen atoms directly bonded to atoms (carbon atoms or heteroatoms) constituting a ring from a heterocyclic compound. Among the heterocyclic groups, an "aromatic heterocyclic group", which is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound, is preferred. A group obtained by removing p hydrogen atoms (p represents an integer of 1 or more) directly bonded to atoms constituting a ring from a heterocyclic compound is also referred to as a "p-valent heterocyclic group". A group obtained by removing p hydrogen atoms directly bonded to atoms constituting a ring from an aromatic heterocyclic compound is also referred to as a "p-valent aromatic heterocyclic group".
Examples of the "aromatic heterocyclic compound" include compounds in which the heterocycle itself exhibits aromaticity, such as azole, thiophene, furan, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, and carbazole, and phenoxazine. , phenothiazine, benzopyran, and the like, compounds in which an aromatic ring is condensed to a heterocyclic ring, even if the heterocyclic ring itself does not exhibit aromaticity.
The number of carbon atoms in the heterocyclic group is generally 1-60, preferably 2-40, more preferably 3-20, not including the number of carbon atoms in the substituent. The number of heteroatoms in the heterocyclic group, not including the number of heteroatoms in the substituent, is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. is.
Heterocyclic groups include, for example, monocyclic heterocyclic compounds such as furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, tetrazole, pyridine, diazabenzene and triazine, or Polycyclic heterocyclic compounds (e.g. azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, benzothiophene dioxide, benzothiophene oxide and bicyclic heterocyclic compounds such as benzopyranone; dibenzofuran, dibenzothiophene, dibenzothiophene dioxide, dibenzothiophene oxide, dibenzopyranone, dibenzoborol, dibenzosilol, dibenzophosphole, dibenzoselenophene, carbazole, azacarbazole , diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, phenazaborine, phenophosphadine, phenoselenazine, phenazacillin, azaanthracene, diazaanthracene, azaphenanthrene and diaza tricyclic heterocyclic compounds such as phenanthrene; tetracyclic heterocyclic compounds such as hexaazatriphenylene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran and benzonaphthothiophene; dibenzocarbazole, India Pentacyclic heterocyclic compounds such as locarbazole, indenocarbazole, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole and diazaindenocarbazole; carbazolocarbazole, benzoindolocarbazole and benzoindenocarbazole Hexacyclic heterocyclic compounds such as; and heptacyclic heterocyclic compounds such as dibenzoindolocarbazole and dibenzoindenocarbazole. Groups excluding one or more may be mentioned. A heterocyclic group is a group in which a plurality of groups are bonded by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic heterocyclic compound or a polycyclic heterocyclic compound, good too. The heterocyclic group may have a substituent.

A "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The "amino group" may have a substituent, preferably a substituted amino group (that is, a secondary amino group or a tertiary amino group, more preferably a tertiary amino group). Preferred substituents on the amino group are alkyl groups, cycloalkyl groups, aryl groups and monovalent heterocyclic groups, and these groups may further have substituents. 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 each is bonded.
Substituted amino groups include, for example, dialkylamino groups, dicycloalkylamino groups, diarylamino groups, and groups in which some or all of the hydrogen atoms in these groups have been further substituted with substituents.
Substituted amino groups include, for example, dimethylamino group, diethylamino group, diphenylamino group, bis(methylphenyl)amino group, bis(3,5-di-tert-butylphenyl)amino group, and hydrogen in these groups. Groups in which some or all of the atoms are further substituted with substituents are included.

An "alkenyl group" may be either linear or branched. The straight-chain alkenyl group usually has 2 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 10 carbon atoms, not including the carbon atoms of the substituents. The number of carbon atoms in the branched alkenyl group is generally 3-30, preferably 4-20, more preferably 4-10, not including the number of carbon atoms in the substituent.
The number of carbon atoms in the "cycloalkenyl group" is generally 3-30, preferably 4-20, more preferably 5-10, not including the number of carbon atoms in the substituents.
Alkenyl groups and cycloalkenyl groups may have a substituent. Examples of alkenyl groups include vinyl group, 1-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 have been substituted with substituents. The cycloalkenyl group includes, for example, a cyclohexenyl group, a cyclohexadienyl group, a cyclooctatrienyl group, a norbornylenyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents. .
An "alkynyl group" may be either linear or branched. The number of carbon atoms in the alkynyl group is usually 2-30, preferably 3-10, not including the carbon atoms of the substituents. The number of carbon atoms in the branched alkynyl group is generally 4-30, preferably 4-10, not including the carbon atoms of the substituents.
The number of carbon atoms in the "cycloalkynyl group" is usually 4-30, preferably 4-10, not including the carbon atoms of the substituents.
The alkynyl group and cycloalkynyl group may have a substituent. Examples of alkynyl groups include ethynyl, 1-propynyl, 2-propynyl, 2-butynyl, 3-butynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 5-hexynyl, and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents. Cycloalkynyl groups include, for example, cyclooctynyl groups and groups in which some or all of the hydrogen atoms in the groups are substituted with substituents.

A “crosslinking group” is a group capable of forming a new bond by subjecting it to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, or the like. The cross-linking group is preferably at least one cross-linking group selected from Group A of cross-linking groups (that is, at least one group selected from groups represented by formulas (XL-1) to (XL-19)). .
(Crosslinking group A group)

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

The "substituent" includes, for example, 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, Alkenyl groups, cycloalkenyl groups, alkynyl groups and cycloalkynyl groups are included. A substituent may be a bridging group. In addition, when multiple substituents are present, they may be the same or different. In addition, when there are multiple substituents, they may bond with each other to form a ring together with the atoms to which they are bonded, but preferably do not form a ring.

The "divalent group" includes, for example, an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ⁰ )-, represented by -B(R ⁰ )- group represented by -P(R ⁰ )-, group represented by -(O=)P(R ⁰ )-, group represented by -O-, represented by -S- a group represented by -Se-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ - and a group represented by -C(=O)- are mentioned. The divalent group may be a group in which a plurality of these groups are bonded. A divalent group may have a substituent. 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 atoms to which they are bonded. R ⁰ represents a hydrogen atom or a substituent.
R ⁰ includes, for example, 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, a halogen atom and a cyano group. , preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.

In this specification, the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state (hereinafter also referred to as “ΔE _ST ”) is calculated by the following method. is required. First, the ground state of the compound is structurally optimized by density functional theory at the B3LYP level. At that time, 6-31G* is used as a basis function. Then, using the obtained structurally optimized structure, _ΔEST of the compound is calculated by B3LYP-level time-dependent density functional theory. However, when 6-31G* contains an atom that cannot be used, LANL2DZ is used for that atom. Gaussian09 is used as a quantum chemical calculation program.

<Composition>
The composition of the present disclosure comprises at least one compound (hereinafter also referred to as "compound (A)") selected from the group consisting of the metal complex represented by formula (1) and the polymer compound (A). , at least one compound (hereinafter also referred to as “compound (B)”) selected from the group consisting of low-molecular compound (B) and high-molecular compound (B), and represented by formula (H-1) and a polymer compound (hereinafter referred to as "first and at least one compound selected from the group consisting of (hereinafter also referred to as "first compound"). That is, the composition of this embodiment is a composition containing compound (A), compound (B), and a first compound.

The composition of the present disclosure can be suitably used, for example, as a composition for light-emitting devices. In addition, a light-emitting device containing the composition of the present disclosure (hereinafter also referred to as a “light-emitting device of the present disclosure”) has a lower driving voltage.

In one embodiment, the composition of the present disclosure may contain only one type of compound (A), compound (B) and first compound, respectively, or may contain two or more types.

In the composition of the present disclosure, the total content of the compound (A), the compound (B) and the first compound is Any range is acceptable as long as the function can be achieved.
In one embodiment of the composition of the present disclosure, the total content of compound (A), compound (B) and the first compound may be, for example, 1 to 100% by mass based on the total amount of the composition. , Since the driving voltage of the light emitting device of the present disclosure is lower, it is preferably 10 to 100% by mass, more preferably 30 to 100% by mass, still more preferably 50 to 100% by mass, and particularly preferably 70 to 100% by mass, particularly preferably 90 to 100% by mass.
In the composition of the present disclosure, the content of compound (B) may be within a range in which the function of the composition is exhibited.
In one embodiment of the composition of the present disclosure, the content of the compound (B) is, for example, 0 when the total content of the compound (A), the compound (B) and the first compound is 100 parts by mass. 0.01 to 99 parts by mass, and the drive voltage of the light-emitting device of the present disclosure is lower, so it is preferably 0.01 to 90 parts by mass, more preferably 0.05 to 70 parts by mass, and even more preferably is 0.1 to 50 parts by mass, particularly preferably 0.5 to 30 parts by mass, particularly preferably 1 to 25 parts by mass.
In the composition of the present disclosure, the content of compound (A) may be within a range in which the function of the composition is exhibited. In the composition of the present disclosure, the content of compound (A) is, for example, 0.01 to 99 when the total content of compound (A), compound (B) and the first compound is 100 parts by mass. It is preferably 0.1 to 95 parts by mass, more preferably 0.5 to 90 parts by mass, and even more preferably 1 to 70 parts by mass, since the driving voltage of the light emitting device of the present disclosure is lower. parts by mass, particularly preferably 5 to 50 parts by mass, particularly preferably 10 to 30 parts by mass.

In one embodiment of the composition of the present disclosure, it is preferred that compound (A), compound (B) and the first compound interact physically, chemically or electrically. This interaction can, for example, enhance or tune the light emitting properties, charge transport properties or charge injection properties of the compositions of the present disclosure, resulting in lower driving voltages for the light emitting devices of the present disclosure.

In one embodiment of the composition of the present disclosure, taking the luminescent material as an example, the first compound, the compound (A), and the compound (B) electrically interact, and the first compound to the compound ( By efficiently transferring electric energy to A) and further efficiently transferring electric energy from compound (A) to compound (B), compound (B) can be made to emit light more efficiently, and the present disclosure , the driving voltage of the light emitting element becomes lower.

In view of the above, in one embodiment of the composition of the present disclosure, the first compound has hole-injecting properties, hole-transporting properties, electron-injecting properties, and electron More preferably, it has at least one function selected from transportability.
From the above viewpoint, in one embodiment of the composition of the present disclosure, the driving voltage of the light-emitting device of the present disclosure is lower, so the compound (A) has hole-injecting, hole-transporting, electron-injecting, and electron More preferably, it has at least one function selected from transportability.
From the above point of view, in one embodiment of the composition of the present disclosure, the compound (B) more preferably has light-emitting properties, since the driving voltage of the light-emitting device of the present disclosure is lower.
From the above viewpoint, in one embodiment of the composition of the present disclosure, the lowest excited singlet state (S ₁ ) possessed by the first compound lowers the driving voltage of the light-emitting device of the present disclosure. is preferably a higher energy level than the lowest excited singlet state (S ₁ ) possessed by .
From the above viewpoint, in one embodiment of the composition of the present disclosure, the lowest excited singlet state (S ₁ ) possessed by the first compound lowers the driving voltage of the light-emitting device of the present disclosure. is preferably a higher energy level than the lowest excited singlet state (S ₁ ) possessed by .
From the above point of view, in one embodiment of the composition of the present disclosure, the lowest excited singlet state (S ₁ ) possessed by compound (A) lowers the driving voltage of the light-emitting device of the present disclosure. is preferably a higher energy level than the lowest excited singlet state (S ₁ ) possessed by .
From the above viewpoint, in one embodiment of the composition of the present disclosure, the lowest excited triplet state (T ₁ ) possessed by the first compound lowers the driving voltage of the light-emitting device of the present disclosure. is preferably at an energy level higher than the lowest excited triplet state (T ₁ ) of .
From the above point of view, in one embodiment of the composition of the present disclosure, the lowest excited triplet state (T ₁ ) possessed by the first compound lowers the driving voltage of the light-emitting device of the present disclosure. is preferably at an energy level higher than the lowest excited triplet state (T ₁ ) of .
From the above point of view, in one embodiment of the composition of the present disclosure, the lowest excited triplet state (T ₁ ) possessed by compound (A) lowers the driving voltage of the light-emitting device of the present disclosure. is preferably at an energy level higher than the lowest excited triplet state (T ₁ ) of .

The compound (A) preferably exhibits solubility in a solvent capable of dissolving the compound (B), since the light-emitting device of the present disclosure can be produced by a wet method.
The first compound preferably exhibits solubility in a solvent capable of dissolving the compound (B) and the compound (A), since the light-emitting device of the present disclosure can be produced by a wet method. .

In one embodiment of the composition of the present disclosure, the first compound is preferably a host material, an assisting dopant material, or a dopant material because the driving voltage of the light-emitting device of the present disclosure is lower. It is more preferably a dopant material, and even more preferably a host material.
In one embodiment of the composition of the present disclosure, the compound (A) is preferably a host material, an assist dopant material, or a dopant material because the driving voltage of the light-emitting device of the present disclosure is lower. A dopant material is more preferred, and an assist dopant material is even more preferred.
In one embodiment of the composition of the present disclosure, the compound (B) is preferably a host material, an assist dopant material, or a dopant material because the driving voltage of the light-emitting device of the present disclosure is lower. Dopant materials are more preferred, and dopant materials are even more preferred.

In one embodiment of the composition of the present disclosure, the host material is preferably a material that physically, chemically or electrically interacts with the assisting dopant material. In one embodiment of the composition of the present disclosure, the host material is preferably a material that physically, chemically or electrically interacts with the dopant material. In one embodiment of the composition of the present disclosure, the assisting dopant material is preferably a material that physically, chemically or electrically interacts with the dopant material. In one embodiment of the composition of the present disclosure, it is preferred that the host material, assisting dopant material and dopant material interact physically, chemically or electrically. These interactions make it possible, for example, to enhance or tune the light emitting properties, charge transport properties or charge injection properties of the compositions of the present disclosure, resulting in lower driving voltages of the light emitting devices of the present disclosure.

In the composition of the present disclosure, taking the light-emitting material as an example, the host material, the assisting dopant material, and the dopant material electrically interact to efficiently transfer electrical energy from the host material to the assisting dopant material, and further By efficiently transferring electrical energy from the assisting dopant material to the dopant material, the dopant material can emit light more efficiently, resulting in a lower driving voltage for the light emitting device of the present disclosure.

In view of the above, in one embodiment of the composition of the present disclosure, the host material has hole-injecting, hole-transporting, electron-injecting and electron-transporting properties, as the driving voltage of the light-emitting device of the present disclosure is lower. It is more preferable to have at least one function selected from
In view of the above, in one embodiment of the composition of the present disclosure, the assist dopant material has hole-injecting, hole-transporting, electron-injecting and electron-transporting properties, so that the driving voltage of the light-emitting device of the present disclosure is lower. It is more preferable to have at least one function selected from nature.
From the above point of view, in one embodiment of the composition of the present disclosure, the dopant material is preferably luminescent, since the driving voltage of the light emitting device of the present disclosure is lower.
From the above point of view, in one embodiment of the composition of the present disclosure, the lowest excited singlet state (S ₁ ) of the host material is the lowest of the assist dopant material, since the driving voltage of the light emitting device of the present disclosure is lower. An energy level higher than the excited singlet state (S ₁ ) is preferred.
From the above point of view, in one embodiment of the composition of the present disclosure, the lowest excited singlet state (S ₁ ) of the host material is the lowest excited singlet state of the dopant material, since the light-emitting device of the present disclosure has a lower driving voltage. An energy level higher than the singlet state (S ₁ ) is preferred.
From the above viewpoint, in one embodiment of the composition of the present disclosure, the lowest excited singlet state (S 1 ) possessed by the assist dopant material is the lowest excited singlet state (S ₁ ) possessed by the dopant material, since the driving voltage of the light emitting device of the present disclosure is lower. An energy level higher than the excited singlet state (S ₁ ) is preferred.
From the above viewpoint, in one embodiment of the composition of the present disclosure, the lowest excited triplet state (T ₁ ) of the host material is the lowest of the assist dopant material, since the driving voltage of the light emitting device of the present disclosure is lower. An energy level higher than the excited triplet state (T ₁ ) is preferred.
From the above viewpoint, in one embodiment of the composition of the present disclosure, the lowest excited triplet state (T ₁ ) possessed by the host material is the lowest excited triplet state possessed by the dopant material, since the driving voltage of the light emitting device of the present disclosure is lower. An energy level higher than the triplet state (T ₁ ) is preferred.
From the above point of view, in one embodiment of the composition of the present disclosure, the lowest excited triplet state (T 1 ) possessed by the assist dopant material is the lowest excited triplet state (T ₁ ) possessed by the dopant material, since the driving voltage of the light emitting device of the present disclosure is lower. An energy level higher than the excited triplet state (T ₁ ) is preferred.

In the composition of the present disclosure, the total content of the host material, the assist dopant material, and the dopant material may be within a range in which the composition functions. In one embodiment of the composition of the present disclosure, the total content of the host material, the assisting dopant material and the dopant material may be, for example, 1 to 100% by mass based on the total amount of the composition. Since the drive voltage of the device becomes lower, it is preferably 10 to 100% by mass, more preferably 30 to 100% by mass, still more preferably 50 to 100% by mass, and particularly preferably 70 to 100% by mass. and particularly preferably 90 to 100% by mass.
In the composition of the present disclosure, the content of the dopant material may be within a range in which the function of the composition is exhibited. In one embodiment of the composition of the present disclosure, the content of the dopant material is, for example, 0.01 to 99 parts by mass when the total content of the host material, assist dopant material and dopant material is 100 parts by mass. Since the driving voltage of the light emitting device of the present disclosure is lower, it is preferably 0.01 to 90 parts by mass, more preferably 0.05 to 70 parts by mass, and still more preferably 0.1 to 50 parts by mass. parts, particularly preferably 0.5 to 30 parts by mass, particularly preferably 1 to 10 parts by mass.
In the composition of the present disclosure, the content of the assist dopant material may be within a range in which the function of the composition is exhibited. In one embodiment of the composition of the present disclosure, the content of the assist dopant material is, for example, 0.01 to 99 parts by mass when the total content of the host material, the assist dopant material and the dopant material is 100 parts by mass. is preferably 0.1 to 95 parts by mass, more preferably 0.5 to 90 parts by mass, and still more preferably 1 to 70 parts by mass, since the driving voltage of the light emitting device of the present disclosure is lower. , particularly preferably 5 to 50 parts by mass, particularly preferably 10 to 30 parts by mass.

The assist dopant material preferably exhibits solubility in a solvent capable of dissolving the dopant material, since the light-emitting device of the present disclosure can be produced by a wet method. The host material preferably exhibits solubility in a solvent capable of dissolving the assist dopant material and the dopant material, since the light-emitting device of the present disclosure can be produced by a wet method.

[Compound (B)]
The compound (B) is at least one selected from the group consisting of low-molecular-weight compounds (B) and high-molecular-weight compounds (B).

(Low molecular weight compound (B))
The low ^- molecular-weight compound (B) is a condensed heterocyclic skeleton (b ) is a low-molecular-weight compound.
In the low-molecular-weight compound (B), when the condensed heterocyclic skeleton (b) contains a nitrogen atom, at least one of the nitrogen atoms contained in the condensed heterocyclic skeleton (b) is a nitrogen that does not form a double bond. It is preferably an atom, and more preferably all of the nitrogen atoms contained in the condensed heterocyclic skeleton (b) are nitrogen atoms that do not form double bonds.
The low-molecular-weight compound (B) is preferably a low-molecular-weight compound containing no transition metal element (that is, a low-molecular-weight compound composed only of typical elements).

The number of carbon atoms in the condensed heterocyclic skeleton (b) is generally 1 to 60, preferably 5 to 40, more preferably 10 to 25, not including the number of carbon atoms of substituents.
The number of heteroatoms in the condensed heterocyclic skeleton (b) is usually 2 to 30, preferably 2 to 15, more preferably 2 to 10, more preferably 2 to 10, not including the number of heteroatoms in the substituents. is 2 to 5, particularly preferably 2 or 3.
The number of boron atoms in the condensed heterocyclic skeleton (b) is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, still more preferably 1 to 3, not including the number of boron atoms in the substituents. is 1.
The total number of oxygen atoms, sulfur atoms, selenium atoms, ^sp3 carbon atoms and nitrogen atoms in the condensed heterocyclic skeleton (b) is usually 1 to 20, preferably 1 to 20, not including the number of substituent atoms. 10, more preferably 1 to 5, still more preferably 1 to 3, and particularly preferably 2.

The condensed heterocyclic skeleton (b) contains a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring, since the driving voltage of the light-emitting device of the present disclosure is lower. It is more preferable to contain a boron atom and a nitrogen atom in the ring, and it is even more preferable to contain a nitrogen atom that does not form a double bond with the boron atom in the ring.

The condensed heterocyclic skeleton (b) is preferably a 3- to 12-ring condensed heterocyclic skeleton, more preferably a 3- to 6-ring condensed heterocyclic skeleton, because the driving voltage of the light-emitting device of the present disclosure is lower. and more preferably a pentacyclic condensed heterocyclic skeleton.

The condensed heterocyclic skeleton (b) can also be referred to as a compound having a heterocyclic group (b') containing the condensed heterocyclic skeleton (b).

The heterocyclic group (b') is a polycyclic heterocyclic group containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an ^sp3 carbon atom and a nitrogen atom in the ring. It may be a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a cyclic compound, and the group may have a substituent.
In the heterocyclic group (b′), a polycyclic heterocyclic compound preferably consists of boron atoms, oxygen atoms, sulfur atoms and nitrogen atoms, because the driving voltage of the light-emitting device of the present disclosure is lower. A polycyclic heterocyclic compound containing in the ring at least one selected from the group, more preferably a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom in the ring More preferably, it is a polycyclic heterocyclic compound containing a boron atom and a nitrogen atom not forming a double bond in the ring.
In the heterocyclic group (b′), the polycyclic heterocyclic compound is preferably a 3- to 12-cyclic heterocyclic compound, more preferably a heterocyclic compound, since the driving voltage of the light-emitting device of the present disclosure is lower. is a 3- to 6-ring heterocyclic compound, more preferably a pentacyclic heterocyclic compound.

Examples of substituents that the heterocyclic group (b′) may have include halogen atoms, cyano groups, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryloxy groups, aryl groups, monovalent heterocyclic groups. A cyclic group or a substituted amino group is preferable, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, an alkyl group, a cycloalkyl group, an aryl group, A monovalent heterocyclic group or a substituted amino group is more preferred, and an alkyl group, cycloalkyl group or aryl group is particularly preferred, and these groups may further have a substituent.

The aryl group in the substituent optionally possessed by the heterocyclic group (b′) is preferably a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon to an atom constituting the ring. A group excluding one directly bonded hydrogen atom, more preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon in which one hydrogen atom directly bonded to a ring-constituting atom is more preferably benzene, naphthalene, anthracene, phenanthrene or fluorene from which one hydrogen atom directly bonded to a ring-constituting atom has been removed, particularly preferably a phenyl group; The group may have a substituent.
The monovalent heterocyclic group in the substituent that the heterocyclic group (b') may have is preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound, A group in which one hydrogen atom directly bonded to a constituent atom is removed, and one hydrogen atom directly bonded to a ring-constituting atom is removed from a monocyclic, bicyclic or tricyclic heterocyclic compound. more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, excluding one hydrogen atom directly bonded to a ring-constituting atom and particularly preferably a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from pyridine, diazabenzene or triazine, and these groups may have a substituent.
In the substituted amino group in the substituent optionally possessed by the heterocyclic group (b′), the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group. The group may further have a substituent. Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in the substituents of the amino group are, respectively, the aryl group and the monovalent heterocyclic ring in the substituents that the heterocyclic group (b') may have It is the same as the example and preferred range of the group.

Substituents which the heterocyclic group (b′) may further have include halogen atoms, cyano groups, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl An oxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is preferred, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group or An aryl group is more preferred, and an alkyl group or a cycloalkyl group is particularly preferred. These groups may further have a substituent, but preferably have no further substituent.
Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent that the heterocyclic group (b′) may further have are The same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that the ring group (b') may have.

A "nitrogen atom that does not form a double bond" means a nitrogen atom that is bonded to three other atoms via single bonds.
"Containing a nitrogen atom that does not form a double bond in the ring" means -N(-R ^N )- (wherein R ^N represents a hydrogen atom or a substituent) or the formula:

It means that the group represented by is included.

The low-molecular-weight compound (B) is preferably a thermally activated delayed fluorescence (TADF) compound, since the driving voltage of the light-emitting device of the present disclosure is lower.
Here, the heat-activated delayed fluorescence compound is a compound having heat-activated delayed fluorescence.

_ΔEST of the low-molecular-weight compound (B) may be 2.0 eV or less, 1.5 eV or less, 1.0 eV or less, or 0.80 eV or less. However, it is preferably 0.60 eV or less, more preferably 0.55 eV or less, and even more preferably 0.50 eV or less, because the driving voltage of the light-emitting device of the present disclosure becomes lower. _ΔEST of the low-molecular-weight compound (B) may be 0.001 eV or more, 0.01 eV or more, 0.10 eV or more, or 0.20 eV or more. may be 0.30 eV or more, or 0.40 eV or more.

The molecular weight of the low molecular weight compound (B) is preferably 1×10 ² to 5×10 ³ , more preferably 2×10 ² to 3×10 ³ , still more preferably 3×10 ² to 1.5. ×10 ³ , particularly preferably 4×10 ² to 1×10 ³ .

Claim 6
The low-molecular-weight compound (B) is a compound represented by formula (1-1), formula (1-2), or formula (1-3) because the driving voltage of the light-emitting device of the present disclosure is lower. is preferred, a compound represented by formula (1-2) or formula (1-3) is more preferred, and a compound represented by formula (1-2) is even more preferred.

Ar ¹ , Ar ² and Ar ³ are preferably monocyclic or bicyclic to hexacyclic aromatic hydrocarbons, or monocyclic or A group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a bicyclic to hexacyclic heterocyclic compound, more preferably monocyclic, bicyclic or tricyclic or a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic, bicyclic or tricyclic heterocyclic compound, more preferably , a group obtained by removing one or more hydrogen atoms directly bonded to the atoms constituting the ring from a monocyclic aromatic hydrocarbon or a monocyclic heterocyclic compound, particularly preferably benzene, pyridine or diazabenzene is a group obtained by removing one or more hydrogen atoms directly bonded to ring-constituting atoms from benzene, and particularly preferably a group obtained by removing one or more hydrogen atoms directly bonded to ring-constituting atoms from benzene. , these groups may have a substituent.
Examples and preferred ranges of substituents that Ar ¹ , Ar ² and Ar ³ may have are the same as examples and preferred ranges of substituents that the heterocyclic group (b′) may have.

Y ¹ is preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)- or an alkylene group, more preferably an oxygen atom, since the driving voltage of the light-emitting device of the present disclosure is lower. , a sulfur atom or a group represented by -N(Ry)-, more preferably a group represented by -N(Ry)-, and these groups may have a substituent.

Y ² and Y ³ are preferably a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, -B A group represented by (Ry)-, an alkylene group or a cycloalkylene group, more preferably a single bond, an oxygen atom, a sulfur atom, a group represented by -N(Ry)-, or -B(Ry)- A group or an alkylene group represented by, more preferably an oxygen atom, a sulfur atom, a group represented by -N(Ry)- or an alkylene group, particularly preferably an oxygen atom, a sulfur atom or -N It is a group represented by (Ry)-, particularly preferably a group represented by -N(Ry)-, and these groups may have a substituent.

The arylene group for Y ² and Y ³ is preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from a monocyclic or bicyclic to hexacyclic aromatic hydrocarbon. and more preferably a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene from which two hydrogen atoms directly bonded to carbon atoms constituting a ring are removed; particularly preferably, benzene, naphthalene or fluorene constitutes a ring; It is a group excluding two hydrogen atoms directly bonded to a carbon atom, particularly preferably a phenylene group, and these groups may have a substituent.
The divalent heterocyclic group for Y ² and Y ³ is preferably a monocyclic or bicyclic to hexacyclic heterocyclic compound directly bonded to a ring-constituting atom (preferably a carbon atom). A group excluding two hydrogen atoms, more preferably a monocyclic, bicyclic or tricyclic heterocyclic compound, a hydrogen directly bonded to an atom (preferably a carbon atom) constituting a ring A group with two atoms removed, more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10- A group obtained by removing two hydrogen atoms directly bonded to ring-constituting atoms (preferably carbon atoms) from dihydroacridine or 5,10-dihydrophenazine, particularly preferably pyridine, diazabenzene, triazine, carbazole, phenoxy a group obtained by removing two hydrogen atoms directly bonded to ring-constituting atoms (preferably carbon atoms) from sazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine, particularly preferably pyridine , diazabenzene or triazine by removing two hydrogen atoms directly bonded to atoms (preferably carbon atoms) constituting the ring, and these groups may have a substituent.
The alkylene group for Y ¹ , Y ² and Y ³ is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.

Since the driving voltage of the light-emitting device of the present disclosure is lower, all of Y ¹ , Y ² and Y ³ are preferably an oxygen atom, a sulfur atom or a group represented by -N(Ry)-, and Y All of ¹ , Y ² and Y ³ are more preferably groups represented by -N(Ry)-.

Examples and preferred ranges of substituents that Y ¹ , Y ² and Y ³ may have are the same as examples and preferred ranges of substituents that the heterocyclic group (b′) may have.

Ry is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group; The group may have a substituent.
Examples and preferred ranges of the aryl group and monovalent heterocyclic group in Ry are respectively examples and preferred examples of the aryl group and monovalent heterocyclic group in the substituent that the heterocyclic group (b′) may have Same as range.
Examples and preferred ranges of substituents that Ry may have are the same as examples and preferred ranges of substituents that the heterocyclic group (b') may have.

Y ¹ and Ar ¹ may be directly bonded or bonded via a divalent group to form a ring. preferably not.
When Y ¹ and Ar ¹ are bonded through a divalent group to form a ring, the divalent group is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent hetero a cyclic group, a group represented by -N(R ⁰ )-, a group represented by -B(R ⁰ )-, a group represented by -O-, a group represented by -S- or -Se- and more preferably an alkylene group, a cycloalkylene group, a group represented by -N(R ⁰ )-, a group represented by -B(R ⁰ )-, and a group represented by -O- a group represented by -S- or a group represented by -Se-, more preferably an alkylene group, a group represented by -N(R ⁰ )-, a group represented by -O- or a group represented by -S-, particularly preferably a group represented by -O-, a group represented by -S- or a group represented by -N(R ⁰ )- , particularly preferably a group represented by -N(R ⁰ )-, and these groups may have a substituent.
When Y ¹ and Ar ¹ are bonded via a divalent group to form a ring, examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in the divalent group are They are the same as the examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group for ^Y2 and ^Y3 , respectively.
When Y ¹ and Ar ¹ are bonded via a divalent group to form a ring, examples and preferred ranges of substituents that the divalent group may have include Y ² and Y It is the same as the examples and preferred range of the substituent that ³ may have.
When Y ¹ and Ar ¹ are bonded through a divalent group to form a ring, examples and preferred ranges of R ⁰ in the divalent group are the same as examples and preferred ranges of Ry .

Y ¹ and Ar ² may be directly bonded or bonded via a divalent group to form a ring. preferably not. Examples and preferred ranges of the divalent group when Y ¹ and Ar ² are bonded via a divalent group to form a ring are Y ¹ and Ar ¹ via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
Y ² and Ar ¹ may be directly bonded or bonded via a divalent group to form a ring. preferably not. Examples and preferred ranges of the divalent group when Y ² and Ar ¹ are bonded via a divalent group to form a ring are Y ¹ and Ar ¹ via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
Y ² and Ar ³ may be directly bonded or bonded via a divalent group to form a ring. preferably not. Examples and preferred ranges of the divalent group when Y ² and Ar ³ are bonded via a divalent group to form a ring are Y ¹ and Ar ¹ via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
Y ³ and Ar ² may be directly bonded or bonded via a divalent group to form a ring. preferably not. Examples and preferred ranges of the divalent group when Y ³ and Ar ² are bonded via a divalent group to form a ring are Y ¹ and Ar ¹ via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
Y ³ and Ar ³ may be directly bonded or bonded via a divalent group to form a ring. preferably not. Examples and preferred ranges of the divalent group when Y ³ and Ar ³ are bonded via a divalent group to form a ring are Y ¹ and Ar ¹ via a divalent group are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.

Examples of the low-molecular-weight compound (B) include compounds represented by the following formula and compounds B1 to B11 described later. In the formula, Z ¹ represents an oxygen atom or a sulfur atom. When multiple Z ¹ are present, they may be the same or different.

The maximum peak wavelength of the emission spectrum of the low-molecular-weight compound (B) at 25° C. is preferably 380 nm or longer, more preferably 400 nm or longer, even more preferably 420 nm or longer, and particularly preferably 440 nm or longer. The maximum peak wavelength of the emission spectrum of the low-molecular-weight compound (B) at 25° C. is preferably 750 nm or less, more preferably 620 nm or less, even more preferably 570 nm or less, particularly preferably 495 nm or less. It is preferably 480 nm or less.
The half width of the maximum peak of the emission spectrum of the low-molecular-weight compound (B) at 25° C. is preferably 50 nm or less, more preferably 40 nm or less, even more preferably 30 nm or less, and particularly preferably 25 nm or less. .
The maximum peak wavelength of the emission spectrum of the compound at room temperature can be determined by dissolving the compound in an organic solvent such as xylene, toluene, chloroform, or tetrahydrofuran to prepare a dilute solution (1×10 ⁻⁶ mass % to 1×10 ⁻³ mass %). %), which can be evaluated by measuring the PL spectrum of the dilute solution at room temperature. Xylene is preferred as the organic solvent for dissolving the compound.

(Polymer compound (B))
The polymer compound (B) is a polymer compound containing a structural unit (hereinafter also referred to as “structural unit (B)”) having a group obtained by removing one or more hydrogen atoms from the low molecular weight compound (B).
The structural unit (B) is preferably a structural unit having a group obtained by removing 1 or more and 5 or less hydrogen atoms from the low-molecular-weight compound (B), and more preferably, because the synthesis of the polymer compound (B) is easy. is a structural unit having a group in which 1 to 3 hydrogen atoms are removed from the low-molecular-weight compound (B), more preferably a group in which 1 or 2 hydrogen atoms are removed from the low-molecular-weight compound (B) is a structural unit having
The structural unit (B) is preferably represented by the formula (BP-1) or the formula (BP- 2) or a structural unit represented by formula (BP-3), more preferably a structural unit represented by formula (BP-1) or formula (BP-2).

[In the formula,
^MBP1 represents a group obtained by removing one hydrogen atom from the low-molecular-weight compound (B).
^MBP2 represents a group obtained by removing two hydrogen atoms from the low-molecular-weight compound (B).
^MBP3 represents a group obtained by removing three hydrogen atoms from the low-molecular-weight compound (B).
L ^BP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^BP1 )-, an oxygen atom or a sulfur atom, and these groups are It may have a substituent. 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 atoms to which they are bonded. ^RBP1 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. 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 atoms to which they are bonded. When multiple ^LBP1 are present, they may be the same or different.
^nBP1 represents an integer of 0 or more and 10 or less.
Ar ^BP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded. ]

L ^BP1 is preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, more preferably an alkylene group or an arylene group, still more preferably an arylene group, these groups may have a substituent.
Examples and preferred ranges of the arylene group and divalent heterocyclic group in ^LBP1 are the same as those of the arylene group and divalent heterocyclic group in Ar ^Y1 described below.
The alkylene group in ^LBP1 is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.
Examples and preferred ranges of R ^BP1 are the same as examples and preferred ranges of R ^X1 to R ^X3 described later.

^nBP1 is preferably an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, still more preferably 0.

The hydrocarbon group for Ar ^BP1 includes an optionally substituted aromatic hydrocarbon group and an optionally substituted aliphatic hydrocarbon group. The hydrocarbon group in Ar ^BP1 includes groups in which multiple of these groups are bonded.
In Ar ^BP1 , the aliphatic hydrocarbon group includes a group obtained by removing one hydrogen atom nBP from an alkylene group or a cycloalkylene group, preferably a group obtained by removing ^one hydrogen atom ^nBP from an alkylene group, These groups may have a substituent. Examples and preferred range of this alkylene group include the examples and preferred range of the alkylene group in L ^H1 described later.
In Ar ^BP1 , the aromatic hydrocarbon group includes a group obtained by removing one hydrogen atom n ^BP from an arylene group, and this group may have a substituent. Examples and preferred ranges of the arylene group include the examples and preferred ranges of the arylene group in Ar ^Y1 described later.
The heterocyclic group for Ar ^BP1 includes a group obtained by removing one hydrogen atom n ^BP from a divalent heterocyclic group, and this group may have a substituent. Examples and preferred ranges of the divalent heterocyclic group include the examples and preferred ranges of the divalent heterocyclic group in Ar ^Y1 described later.
Examples and preferred examples of substituents that L ^BP1 and Ar ^{2 BP1} may have are the same as examples and preferred ranges of substituents that the group represented by Ar ^Y1 may have, which will be described later.

Examples of the structural unit (B) include structural units represented by the following formula.

[In the formula,
^RTS is 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 further have a substituent. A plurality of R ^TS may be the same or different. ]

Examples and preferred ranges of the aryl ^group , monovalent heterocyclic group and substituted amino group in R ^TS are, respectively, the aryl group, monovalent heterocyclic It is the same as the examples and preferred ranges of the cyclic group and the substituted amino group.
Examples and preferred ranges of substituents that R ^TS may have include examples and preferred ranges of substituents that the group represented by Ar ^Y1 described later may further have. are the same.

The content of the structural unit (B) contained in the polymer compound (B) may be within a range where the function of the polymer compound (B) is exhibited. The content of the structural unit (B) contained in the polymer compound (B) is, for example, 0.01 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (B). , preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, because the driving voltage of the light-emitting device of the present disclosure is lower. , particularly preferably 0.5 to 30 mol %, particularly preferably 1 to 10 mol %. Only one type of structural unit (B) may be contained in the polymer compound (B), or two or more types thereof may be contained.

Since the polymer compound (B) lowers the driving voltage of the light emitting device of the present disclosure, it is a group consisting of a structural unit represented by the formula (X) described later and a structural unit represented by the formula (Y) described later. It is preferable to further contain at least one structural unit selected from the above. That is, the polymer compound (B) contains at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later; It is preferably a polymer compound containing the unit (B).
The polymer compound (B) comprises at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later, and a structural unit ( B), the structural unit (B) is preferably different from the structural unit represented by the formula (X) described later and the structural unit represented by the formula (Y) described later.
The polymer compound (B) preferably further contains a structural unit represented by the formula (Y) described below, since the driving voltage of the light-emitting device of the present disclosure is lower.
The polymer compound (B) has an excellent hole-transporting property of the polymer compound (B), and the driving voltage of the light-emitting device of the present disclosure is lower. is preferably further included.
The polymer compound (B) has an excellent hole-transport property of the polymer compound (B) and further lowers the driving voltage of the light-emitting device of the present disclosure. and preferably further comprises a structural unit represented by formula (Y) described later.

When the polymer compound (B) contains a structural unit represented by the below-described formula (X), the content of the structural unit represented by the below-described formula (X) is such that the polymer compound (B) functions as It can be any range as long as it can be played. When the polymer compound (B) contains a structural unit represented by the below-described formula (X), the content of the structural unit represented by the below-described formula (X) is the constitution contained in the polymer compound (B). For example, it is 0.01 to 99.9 mol% with respect to the total content of the units, the hole transport property of the polymer compound (B) is excellent, and the driving voltage of the light emitting device of the present disclosure is higher. Since the mol %, particularly preferably 1 to 10 mol %.
The structural unit represented by formula (X) may be contained in the polymer compound (B) singly or in combination of two or more.

When the polymer compound (B) contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is within a range in which the polymer compound (B) functions. If it is When the polymer compound (B) contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is the total of the structural units contained in the polymer compound (B). With respect to the content, it is, for example, 1 to 99.99 mol %, and since the driving voltage of the light-emitting device of the present disclosure is lower, it is preferably 10 to 99.95 mol %, more preferably 30 to 99 mol %. 0.9 mol %, more preferably 50 to 99.8 mol %, particularly preferably 70 to 99.5 mol %, particularly preferably 90 to 99 mol %.
The structural unit represented by formula (Y) may be contained in the polymer compound (B) singly or in combination of two or more.

When the polymer compound (B) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (B), it is represented by the formula (X) The total content of the structural unit represented by the formula (Y) and the structural unit (B) may be within a range in which the function of the polymer compound (B) can be exhibited. When the polymer compound (B) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (B), it is represented by the formula (X) The total content of the structural unit represented by the formula (Y) and the structural unit (B) is, for example, 1 It is preferably 10 to 100 mol %, more preferably 10 to 100 mol %, because the hole transport property of the polymer compound (B) is excellent and the driving voltage of the light emitting device of the present disclosure is lower. It is 30 to 100 mol %, more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, particularly preferably 90 to 100 mol %.

Examples of the polymer compound (B) include polymer compounds BP-1 to BP-4. Here, "other" means a structural unit other than the structural unit (B), the structural unit represented by formula (X), and the structural unit represented by formula (Y).

[In the table, p ^b , q ^b , r ^b and s ^b represent the molar ratio (mol %) of each structural unit. p ^b +q ^b +r ^b +s ^b =100 and 70≦p ^b +q ^b +r ^b ≦100. ]

The polymer compound (B) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other modes. It is preferably a copolymer obtained by copolymerizing monomers.

The example and preferred range of the polystyrene-equivalent number average molecular weight of the polymer compound (B) are the same as the example and preferred range of the polystyrene-equivalent number average molecular weight of the first polymer compound described below. The example and preferred range of the polystyrene-equivalent weight average molecular weight of the polymer compound (B) are the same as the example and preferred range of the polystyrene-equivalent weight average molecular weight of the first polymer compound described below.

(Method for producing polymer compound (B))
The polymer compound (B) can be produced by the same method as the method for producing the first polymer compound described below.

[Compound (A)]
The compound (A) is at least one selected from the group consisting of the metal complex represented by Formula (1) and the polymer compound (A).

(Metal complex represented by formula (1))
The metal complex represented by formula (1) is preferably a low-molecular-weight compound.
The molecular weight of the metal complex represented by formula (1) is preferably 3×10 ² to 1×10 ⁴ , more preferably 4×10 ² to 7×10 ³ , still more preferably 5×10 2 to 7×10 3 . 10 ² to 5×10 ³ , particularly preferably 6×10 ² to 3×10 ³ , particularly preferably 7×10 ² to 2×10 ³ .

M is preferably an iridium atom or a platinum atom, more preferably an iridium atom, since the driving voltage of the light-emitting device of the present disclosure is lower.
When M is a rhodium atom or an iridium atom, ⁿ¹ is preferably 2 or 3, more preferably 3.
ⁿ¹ is preferably 2 when M is a palladium atom or a platinum atom.

At least one of E ¹ and E ² is preferably a carbon atom, more preferably E ¹ and E ² are carbon atoms.
E ¹ and E ² are preferably the same because the metal complex represented by formula (1) can be easily synthesized. In addition, since the metal complex represented by formula (1) can be easily synthesized, when there are a plurality of E ¹ 's, it is preferable that at least two of the plurality of E ^{1 's} are the same. are all the same. In addition, since the metal complex represented by formula ⁽ 1) can be easily synthesized, when there are a plurality of E ² , it is preferable that at least two of the plurality of E ² are the same. are all the same.

The number of carbon atoms in the aromatic heterocyclic ring containing a 5-membered ring in ring L ¹ is preferably 1 to 30, more preferably 1 to 10, more preferably 1 to 10, not including the number of carbon atoms in the substituents. 1 to 5, particularly preferably 1 to 3.
The number of heteroatoms in the aromatic heterocyclic ring in ring L ¹ is preferably 1 to 30, more preferably 1 to 10, still more preferably 1 to 5, not including the number of heteroatoms in the substituents. , particularly preferably 1 to 3.
Examples of the ring L ¹ include, among the aromatic heterocycles exemplified in the section of the heterocyclic group described above, an aromatic heterocycle containing a 5-membered ring containing one or more nitrogen atoms in the ring, The aromatic heterocycle may have a substituent. Among these, ring L ¹ is preferably an aromatic heterocyclic ring containing a 5-membered ring containing 2 or more and 4 or less nitrogen atoms in the ring, because the driving voltage of the light-emitting device of the present disclosure is lower. , more preferably an aromatic heterocyclic ring containing a 5-membered ring containing 2 or 3 nitrogen atoms in the ring, still more preferably an aromatic heterocyclic ring containing a 5-membered ring containing 3 nitrogen atoms in the ring ring, and these rings may have a substituent.
Ring L ¹ is preferably a pyrrole ring, a diazole ring, a triazole ring or a tetrazole ring, more preferably a diazole ring, a triazole ring or a tetrazole ring, since the driving voltage of the light-emitting device of the present disclosure is lower. A diazole ring or a triazole ring is more preferred, and a triazole ring is particularly preferred, and these rings may have a substituent.
Since the metal complex represented by formula (1) can be easily synthesized, when a plurality of ring L ¹ are present, it is preferable that at least two of the plurality of ring L ¹ are the same. ¹ are more preferably the same.

The number of carbon atoms in the aromatic hydrocarbon ring in ring L ² is preferably 6 to 60, more preferably 6 to 40, still more preferably 6 to 20, not including the number of carbon atoms in substituents. be.
Examples of the aromatic hydrocarbon ring in the ring L ² include the aromatic hydrocarbon rings exemplified in the section of the aromatic hydrocarbon group above, preferably an aromatic hydrocarbon ring containing a 5- or 6-membered ring. It is a hydrogen ring, and these aromatic hydrocarbon rings may have a substituent. Among these, the aromatic hydrocarbon ring in the ring L ² is preferably a monocyclic or bicyclic ring exemplified in the section of the aromatic hydrocarbon group above, because the driving voltage of the light-emitting element of the present disclosure is lower. a cyclic or tricyclic aromatic hydrocarbon ring (preferably an aromatic hydrocarbon ring containing a 5- or 6-membered ring), more preferably a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring or a dihydrophenanthrene It is a ring, more preferably a benzene ring or a fluorene ring, particularly preferably a benzene ring, and these rings may have a substituent.
The number of carbon atoms in the aromatic heterocyclic ring in ring L ² is preferably 1 to 60, more preferably 2 to 40, still more preferably 3 to 20, not including the number of carbon atoms in substituents. . The number of heteroatoms in the aromatic heterocyclic ring in ring L ² is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, not including the number of heteroatoms in substituents. .
Examples of the aromatic heterocyclic ring in ring L ² include the aromatic heterocyclic rings exemplified in the section of the heterocyclic group described above, preferably an aromatic heterocyclic ring containing a 5- or 6-membered ring, These aromatic heterocycles may have a substituent. Among these, the aromatic heterocyclic ring in the ring L ² is preferably monocyclic, bicyclic or tricyclic, as exemplified in the section of the heterocyclic group above, since the driving voltage of the light-emitting device of the present disclosure is lower. cyclic aromatic heterocycle (preferably aromatic heterocycle containing 5- or 6-membered ring), more preferably pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, indole ring, benzofuran ring, benzothiophene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring or dibenzothiophene ring, more preferably pyridine ring, diazabenzene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring; A dibenzothiophene ring or a dibenzofuran ring is particularly preferred, and these rings may have a substituent.
Ring L ² is preferably an aromatic hydrocarbon ring containing a 5- or 6-membered ring, or an aromatic A heterocyclic ring is preferable, and these rings may have a substituent.
Ring L ² is preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring (preferably a 5-membered ring or 6-membered ring (an aromatic hydrocarbon ring containing is a benzene ring, a fluorene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, more preferably a benzene ring, a dibenzothiophene ring or a dibenzofuran ring, and these rings have substituents. You may have
Since the metal complex represented by formula (1) can be easily synthesized, when there are a plurality of ring L ² , it is preferable that at least two of the plurality of ring L ² are the same. ² are more preferably the same.

Since the driving voltage of the light-emitting device of the present disclosure is further lowered, ring L ¹ is a pyrrole ring, diazole ring, triazole ring or tetrazole ring, and ring L ² is a benzene ring, a fluorene ring, a pyridine ring, a diazabenzene ring, A carbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is preferable, ring L ¹ is a diazole ring or triazole ring, and ring L ² is a benzene ring, fluorene ring, pyridine ring, diazabenzene ring, carbazole ring, or dibenzofuran ring. or more preferably a dibenzothiophene ring, ring L ¹ is a triazole ring, and ring L ² is a benzene ring, fluorene ring, pyridine ring, diazabenzene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring. is more preferred, and it is particularly preferred that ring L ¹ is a triazole ring and ring L ² is a benzene ring, dibenzothiophene ring or dibenzofuran ring, and these rings may have a substituent.

Preferred substituents that the ring L ¹ and ring L ² may have (hereinafter also referred to as "primary substituents") include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group and an aryl group. , an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably is an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups are further substituted (hereinafter referred to as "secondary substituted Also referred to as "group").

At least one of ring L ¹ and ring L ² preferably has a primary substituent, as this results in a lower driving voltage for the light-emitting device of the present disclosure.
In the metal complex represented by formula (1), when at least one of ring L ¹ and ring L ² has a primary substituent and there are a plurality of ring L ¹ and ring L 2, a plurality of ring L 1 and ring L ² are present At least one ring out of ring L ¹ and ring L ² should have a primary substituent, but the driving voltage of ^the light-emitting device of the present disclosure is lower. At least two of ² preferably have a primary substituent, and more preferably at least three of the plurality of ring L ¹ and ring L ² have a primary substituent. Further, in the metal complex represented by formula (1), when at least one of ring L ¹ and ring L ² has a primary substituent, and a plurality of ring L ¹ and ring L ² are present, the present Since the driving voltage of the disclosed light-emitting device is lower, at least two of the plurality of rings L ¹ have primary substituents, or at least two of the plurality of rings L ² have primary substituents. More preferably, all of the plurality of ring L ¹ have a primary substituent, or all of the plurality of ring L ² have a primary substituent, and all of the plurality of ring L ¹ It is further preferred that has a primary substituent.
In the metal complex represented by formula (1), when at least one of ring L ¹ and ring L ² has a primary substituent, at least one of ring L ¹ and ring L ² has a primary substituent The number is usually 1 to 10, and preferably 1 to 5 because the metal complex represented by formula (1) can be easily synthesized and the driving voltage of the light emitting device of the present disclosure is lower. , more preferably 1 to 3, still more preferably 1 or 2.
In the metal complex represented by formula (1), when at least one of ring L ¹ and ring L ² has a primary substituent and M is a rhodium atom or an iridium atom, ring L ¹ and ring The total number of primary substituents that L ² has is usually 1 to 30, the metal complex represented by formula (1) can be easily synthesized, and the driving voltage of the light-emitting device of the present disclosure is Since it becomes lower, it is preferably 1 to 18, more preferably 2 to 12, and still more preferably 3 to 6.
In the metal complex represented by formula (1), when at least one of ring L ¹ and ring L ² has a primary substituent and M is a palladium atom or a platinum atom, ring L ¹ and ring The total number of primary substituents that L ² has is usually 1 to 20, the metal complex represented by formula (1) can be easily synthesized, and the driving voltage of the light-emitting device of the present disclosure is Since it becomes lower, it is preferably 1 to 12, more preferably 1 to 8, and still more preferably 2 to 4.

The aryl group in the primary substituent is preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon group excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, A phenyl group, a naphthyl group or a fluorenyl group is more preferred, and a phenyl group is even more preferred, and these groups may have a substituent.
As the monovalent heterocyclic group in the primary substituent, preferably, one hydrogen atom directly bonded to a carbon atom or heteroatom constituting a ring from a monocyclic, bicyclic or tricyclic heterocyclic compound and more preferably a pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring directly to a carbon atom or heteroatom constituting the ring. A group in which one hydrogen atom is removed, more preferably a group in which one hydrogen atom directly bonded to a ring-constituting carbon atom is removed from a pyridine ring, a diazabenzene ring or a triazine ring, and these groups may have a substituent.
In the substituted amino group in the primary substituent, the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. . Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent of the amino group are the same as those of the aryl group and monovalent heterocyclic group in the primary substituent.

Examples and preferred ranges of the secondary substituents (substituents that the primary substituent may further have) are the same as the examples and preferred ranges of the primary substituents.
The secondary substituent may further have a substituent (hereinafter also referred to as "tertiary substituent"). Examples and preferred ranges of tertiary substituents (substituents that secondary substituents may further have) are the same as examples and preferred ranges of primary substituents.
The tertiary substituent may further have a substituent (hereinafter also referred to as "quaternary substituent"). The quaternary substituent (substituent that the tertiary substituent may further have) is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent a cyclic group, a substituted amino group or a fluorine 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, a cycloalkyl group or An aryl group, particularly preferably an alkyl group or a cycloalkyl group, which may further have a substituent, because the metal complex represented by the formula (1) can be easily synthesized. , and preferably have no substituents.
Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the secondary substituent, tertiary substituent and quaternary substituent are respectively the aryl group, monovalent heterocyclic group and It is the same as the example and preferred range of the substituted amino group.

(anionic bidentate ligand)
Examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² include ligands represented by the following formulae. However, the anionic bidentate ligand represented by A ¹ -G ¹ -A ² is different from the ligand whose number is defined by the subscript n ¹ .

[In the formula, * represents a site that binds to M. ]

Examples of the metal complex represented by formula (1) include the metal complexes shown below and metal complexes MC5 to MC9 described later.

(Polymer compound (A))
The polymer compound (A) is a polymer containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (1) (hereinafter also referred to as "structural unit (A)"). is a compound.
Structural unit (A) is preferably a structural unit having a group obtained by removing 1 or more and 5 or less hydrogen atoms from the metal complex represented by formula (1), since synthesis of polymer compound (A) is easy. more preferably a structural unit having a group obtained by removing 1 or more and 3 or less hydrogen atoms from the metal complex represented by formula (1), and still more preferably a metal complex represented by formula (1) It is a structural unit having a group obtained by removing one or two hydrogen atoms from
The structural unit (A) is preferably represented by formula (AP-1) or formula (AP- 2) or a structural unit represented by formula (AP-3), more preferably a structural unit represented by formula (AP-1) or formula (AP-2), still more preferably a structural unit represented by formula ( It is a structural unit represented by AP-1).

[In the formula,
^MAP1 represents a group obtained by removing one hydrogen atom from the metal complex represented by formula (1).
^MAP2 represents a group obtained by removing two hydrogen atoms from the metal complex represented by formula (1).
^MAP3 represents a group obtained by removing three hydrogen atoms from the metal complex represented by formula (1).
L ^AP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^AP1 )-, an oxygen atom or a sulfur atom, and these groups are It may have a substituent. 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 atoms to which they are bonded. ^RAP1 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. 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 atoms to which they are bonded. When multiple ^LAP1 are present, they may be the same or different.
n ^AP1 represents an integer of 0 or more and 10 or less.
Ar ^AP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded. ]

The examples and preferred ranges of L ^AP1 are the same as the examples and preferred ranges of L ^BP1 .
The examples and preferred ranges of ^RAP1 are the same as the examples and preferred ranges of ^RBP1 .
The examples and preferred ranges of ^nAP1 are the same as the examples and preferred ranges of ^nBP1 .
The examples and preferred ranges of Ar ^AP1 are the same as the examples and preferred ranges of Ar ^BP1 .

Examples of structural units (A) include structural units represented by the following formulas.

[In the formula,
Z ² represents a group represented by -CH= or a group represented by -N=. When multiple Z ² are present, they may be the same or different.
^RA represents a hydrogen atom or a primary substituent. When multiple ^RAs are present, they may be the same or different. ]

The content of the structural unit (A) contained in the polymer compound (A) may be within a range in which the function of the polymer compound (A) is exhibited. The content of the structural unit (A) contained in the polymer compound (A) is, for example, 0.01 to 100 mol% with respect to the total content of the structural units contained in the polymer compound (A). is preferably 0.1 to 99 mol%, more preferably 0.5 to 90 mol%, still more preferably 1 to 70 mol%, because the driving voltage of the light-emitting device of the present disclosure is lower. , particularly preferably 5 to 50 mol %, particularly preferably 10 to 30 mol %. 1 type of structural units (A) may be contained in the polymer compound (A), and 2 or more types may be contained.

Since the polymer compound (A) lowers the driving voltage of the light emitting device of the present disclosure, it is a group consisting of a structural unit represented by the formula (X) described later and a structural unit represented by the formula (Y) described later. It is preferable to further contain at least one structural unit selected from the above. That is, the polymer compound (A) includes at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later; It is preferably a polymer compound containing the unit (A).
The polymer compound (A) comprises at least one structural unit selected from the group consisting of structural units represented by the formula (X) described later and structural units represented by the formula (Y) described later, and a structural unit ( A), the structural unit (A) is preferably different from the structural unit represented by the formula (X) described later and the structural unit represented by the formula (Y) described later.
It is preferable that the polymer compound (A) further contains a structural unit represented by formula (Y), which will be described later, since the driving voltage of the light-emitting device of the present disclosure is lower.
The polymer compound (A) has an excellent hole-transport property, and the driving voltage of the light-emitting device of the present disclosure is lower. It is preferable to further include
The polymer compound (A) has an excellent hole-transport property, and the driving voltage of the light-emitting device of the present disclosure is lower. and preferably further comprises a structural unit represented by formula (Y) described later.

When the polymer compound (A) contains a structural unit represented by formula (X) described later, the content of the structural unit represented by formula (X) described later is such that the function of the polymer compound (A) is It can be any range as long as it can be played. When the polymer compound (A) contains a structural unit represented by the formula (X) described below, the content of the structural unit represented by the formula (X) described below is the constitution included in the polymer compound (A). For example, it is 0.01 to 99.9 mol% with respect to the total content of the units, the hole transport property of the polymer compound (B) is excellent, and the driving voltage of the light emitting device of the present disclosure is higher. Since the mol %, particularly preferably 1 to 10 mol %.
The structural unit represented by formula (X) may be contained in the polymer compound (A) singly or in combination of two or more.

When the polymer compound (A) contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is within the range in which the polymer compound (A) functions. If it is When the polymer compound (A) contains the structural unit represented by the formula (Y), the content of the structural unit represented by the formula (Y) is the total of the structural units contained in the polymer compound (A). With respect to the content, it is, for example, 0.1 to 99.99 mol%, and since the driving voltage of the light-emitting device of the present disclosure is lower, it is preferably 1 to 99.9 mol%, more preferably 10 99.5 mol %, more preferably 30 to 99 mol %, particularly preferably 50 to 95 mol %, particularly preferably 70 to 90 mol %.
The structural unit represented by formula (Y) may be contained in the polymer compound (A) singly or in combination of two or more.

When the polymer compound (A) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (A), it is represented by the formula (X) The total content of the structural unit represented by the formula (Y), the structural unit represented by the formula (Y), and the structural unit (A) may be within a range in which the function of the polymer compound (A) can be exhibited. When the polymer compound (A) contains the structural unit represented by the formula (X) and/or the structural unit represented by the formula (Y), and the structural unit (A), it is represented by the formula (X) The total content of the structural unit represented by the formula (Y) and the structural unit (A) is, for example, 1 It is preferably 10 to 100 mol %, more preferably 10 to 100 mol %, because the hole transport property of the polymer compound (A) is excellent and the driving voltage of the light emitting device of the present disclosure is lower. It is 30 to 100 mol %, more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, particularly preferably 90 to 100 mol %.

Examples of the polymer compound (A) include polymer compounds AP-1 to AP-4. Here, "other" means a structural unit other than the structural unit (A), the structural unit represented by formula (X), and the structural unit represented by formula (Y).

[In the table, p ^a , q ^a , r ^a and ^sa represent the molar ratio (mol %) of each structural unit. p ^a +q ^{a +} ra +s ^a =100 and 70≦ ^pa +q ^a + ^ra ≦100. ]

The polymer compound (A) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may be in other forms. It is preferably a copolymer obtained by copolymerizing monomers.

The example and preferred range of the polystyrene-equivalent number average molecular weight of the polymer compound (A) are the same as the example and preferred range of the polystyrene-equivalent number average molecular weight of the first polymer compound described below. The example and preferred range of the polystyrene-equivalent weight average molecular weight of the polymer compound (A) are the same as the example and preferred range of the polystyrene-equivalent weight average molecular weight of the first polymer compound described below.

(Method for producing polymer compound (A))
The polymer compound (A) can be produced by a method similar to the method for producing the first polymer compound described below.

[First compound]
The first compound is at least one selected from the group consisting of the compound represented by formula (H-1) and the first polymer compound.

(Compound represented by formula (H-1))
The compound represented by formula (H-1) is preferably a low-molecular-weight compound.
Since the driving voltage of the light-emitting device of the present disclosure is further lowered, the molecular weight of the compound represented by formula (H-1) is preferably 1×10 ² to 5×10 ³ , more preferably 2×10 ^{2 .} 3×10 3 to 3×10 ³ , more preferably 3×10 ² to 1.5×10 ³ , particularly preferably 4×10 ² to 1×10 ³ .
The compound represented by formula (H-1) is preferably a compound different from compound (B), and more preferably a compound that does not have a condensed heterocyclic skeleton (b).

The aryl groups in Ar ^H1 and Ar ^H2 are preferably directly bonded to ring-constituting atoms of monocyclic or 2- to 7-cyclic aromatic hydrocarbons, because the driving voltage of the light-emitting device of the present disclosure is lower. is a group in which one hydrogen atom is removed, more preferably a monocyclic or bi- to five-ring aromatic hydrocarbon group in which one hydrogen atom directly bonded to an atom constituting a ring is removed More preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, and these groups have substituents. You may have
Aryl groups in Ar ^H1 and Ar ^H2 are preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene, benzofluorene, dibenzo a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from anthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene or benzofluoranthene, more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene or benzofluorene, from which one hydrogen atom directly bonded to a ring-constituting atom is removed, more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or A group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from fluorene, particularly preferably benzene, naphthalene or anthracene, with one hydrogen atom directly bonded to a ring-constituting atom removed. groups, and these groups may have a substituent.

The monovalent heterocyclic group in Ar ^H1 and Ar ^H2 is a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from a heterocyclic compound that does not contain a condensed heterocyclic skeleton (b). is preferred, and this group may have a substituent. In the monovalent heterocyclic group for Ar ^H1 and Ar ^H2 , the heterocyclic compound that does not contain a condensed heterocyclic skeleton (b) includes, for example, among the heterocyclic compounds described in the section on the heterocyclic group above, , a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an ^sp3 carbon atom and a nitrogen atom in the ring.
The monovalent heterocyclic groups in Ar ^H1 and Ar ^H2 are preferably monocyclic or di- to hepta-cyclic heterocyclic compounds (preferably condensed A group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from a monocyclic or 2- to 7-ring heterocyclic compound containing no heterocyclic skeleton (b)), more preferably Atoms constituting a ring from a monocyclic or bi- to pentacyclic heterocyclic compound (preferably a monocyclic or bi- to pentacyclic heterocyclic compound containing no condensed heterocyclic skeleton (b)) is a group excluding one hydrogen atom directly bonded to the (monocyclic, bicyclic or tricyclic heterocyclic compound) by removing one hydrogen atom directly bonded to an atom constituting the ring, particularly preferably tricyclic heterocyclic compound (Preferably, a tricyclic heterocyclic compound that does not contain a condensed heterocyclic skeleton (b)) is a group in which one hydrogen atom directly bonded to an atom constituting the ring is removed, and these groups are substituted You may have a group.
The monovalent heterocyclic groups in Ar ^H1 and Ar ^H2 are preferably furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, pyridine, diazabenzene, since the driving voltage of the light-emitting device of the present disclosure is further lowered. , triazine, azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine , phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracene, diazaanthracene, azaphenanthrene, diazaphenanthrene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene , dibenzocarbazole, indolocarbazole, indenocarbazole, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole or diazaindenocarbazole, with one hydrogen atom directly bonded to a ring-constituting atom removed. and more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10- dihydrophenazine, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole or di A group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from zaindenocarbazole, more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, aza carbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine with one hydrogen atom directly bonded to a ring-constituting atom removed, particularly preferably pyridine , diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, or carbazole from which one hydrogen atom directly bonded to a ring-constituting atom is removed, particularly preferably dibenzofuran, dibenzothiophene, or carbazole. It is a group in which one hydrogen atom is directly bonded to a ring-constituting atom, and these groups may have a substituent.

In the substituted amino group for Ar ^H1 and Ar ^H2 , the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. good too. Examples and preferred ranges of the aryl group, which is a substituent of the amino group, are the same as the examples and preferred ranges of the aryl group in Ar ^H1 and Ar ^H2 . Examples and preferred ranges of the monovalent heterocyclic group which is a substituent of the amino group are the same as the examples and preferred range of the monovalent heterocyclic group in Ar ^{1 H1} and Ar ^{2 H2} .

At least one of Ar ^H1 and Ar ^H2 is preferably an aryl group or a monovalent heterocyclic group, and both Ar ^H1 and Ar ^H2 are aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
The aryl group and monovalent heterocyclic group in Ar ^H1 and Ar ^H2 are monocyclic, bicyclic or tricyclic aromatic hydrocarbons, or , a monocyclic, bicyclic or tricyclic heterocyclic compound (preferably a monocyclic, bicyclic or tricyclic heterocyclic compound that does not contain a condensed heterocyclic skeleton (b)) , is preferably a group in which one hydrogen atom directly bonded to an atom constituting the ring is removed, and the ring is selected from benzene, naphthalene, fluorene, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, or carbazole. A group in which one hydrogen atom directly bonded to a constituent atom is removed is more preferable, and a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzothienyl group or a dibenzofuryl group is more preferable, and a phenyl group, a naphthyl group or a carbazolyl group. is particularly preferred, and these groups may have a substituent.

Preferred substituents that Ar ^H1 and Ar ^H2 may have are a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, and a monovalent A heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group , a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, even if these groups further have a substituent good.
Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that Ar ^H1 and Ar ^H2 may have are the aryl group and monovalent heterocyclic group in Ar ^H1 and Ar ^H2 , respectively. It is the same as the examples and preferred ranges of the cyclic group and the substituted amino group.

Preferred substituents that the substituents Ar ^H1 and Ar ^H2 may further have include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably , an alkyl group, a cycloalkyl group or an aryl group, particularly preferably an alkyl group or a cycloalkyl group, and these groups may further have a substituent, but should not have a further substituent. is preferred.
Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents which the substituents which Ar ^H1 and Ar ^H2 may further have are respectively Ar ^H1 and The same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in Ar ^H2 .

The divalent group for L ^H1 is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, —N(R ⁰ ), since the driving voltage of the light-emitting device of the present disclosure is lower. A group represented by -, a group represented by -(O=)P(R ⁰ )-, a group represented by -O-, a group represented by -S-, and -S(=O) ₂ - or a group represented by -C(=O)-, more preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, or -N(R ⁰ )- a group represented by -O- or a group represented by -S-, more preferably an alkylene group, a cycloalkylene group, an arylene group or a divalent heterocyclic group, particularly preferably is an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
At least one of the divalent groups in L ^H1 is preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, since the driving voltage of the light emitting device of the present disclosure is lower, and more An arylene group or a divalent heterocyclic group is preferable, and these groups may have a substituent.

Among the divalent groups in L ^H1 , the arylene group is preferably a monocyclic or bi- to seven-cyclic aromatic hydrocarbon ring-constituting atom because the driving voltage of the light-emitting device of the present disclosure is lower. A group in which two hydrogen atoms directly bonded to are removed, more preferably a monocyclic or 2- to 5-cyclic aromatic hydrocarbon in which two hydrogen atoms directly bonded to the atoms constituting the ring are removed group, more preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting the ring from a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, and these groups are substituted You may have a group.
Among the divalent groups in L ^H1 , arylene groups are preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzoanthracene, benzophenanthrene, benzo a group obtained by removing two hydrogen atoms directly bonded to ring-constituting atoms from fluorene, dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene or benzofluoranthene, more preferably benzene, naphthalene or anthracene , phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene or benzofluorene, from which two hydrogen atoms directly bonded to atoms constituting the ring are removed, more preferably benzene, naphthalene, anthracene, phenanthrene, A group obtained by removing two hydrogen atoms directly bonded to ring-constituting atoms from dihydrophenanthrene or fluorene, and particularly preferably benzene, naphthalene or anthracene with two hydrogen atoms directly bonded to ring-constituting atoms. These groups may have a substituent.

In the divalent group in L ^H1 , the divalent heterocyclic group is a hydrogen atom directly bonded to a ring-constituting atom (preferably a carbon atom) from a heterocyclic compound that does not contain a condensed heterocyclic skeleton (b). It is preferably a group excluding two, and this group may have a substituent. In the divalent group in L ^H1 , the heterocyclic compound that does not contain a condensed heterocyclic skeleton (b) in the divalent heterocyclic group includes the heterocyclic compounds described in the section on the heterocyclic group above. , a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an ^sp3 carbon atom and a nitrogen atom in the ring.
Among the divalent groups in L ^H1 , a divalent heterocyclic group is preferably a monocyclic or di- to hepta-cyclic heterocyclic compound (preferably is a monocyclic or 2- to 7-ring heterocyclic compound that does not contain a condensed heterocyclic skeleton (b)), except for two hydrogen atoms directly bonded to the atoms (preferably carbon atoms) constituting the ring more preferably a monocyclic or bi- to pentacyclic heterocyclic compound (preferably a monocyclic or bi- to pentacyclic heterocyclic ring that does not contain a condensed heterocyclic skeleton (b) A group obtained by removing two hydrogen atoms directly bonded to atoms (preferably carbon atoms) constituting a ring from the formula compound), more preferably a monocyclic, bicyclic or tricyclic heterocyclic compound A hydrogen atom directly bonded to an atom (preferably a carbon atom) constituting a ring from (preferably a monocyclic, bicyclic or tricyclic heterocyclic compound that does not contain a condensed heterocyclic skeleton (b)) A group excluding two, particularly preferably a tricyclic heterocyclic compound (preferably a tricyclic heterocyclic compound containing no condensed heterocyclic skeleton (b)) to form a ring. It is a group excluding two hydrogen atoms directly bonded to an atom (preferably a carbon atom), and these groups may have a substituent.
Among the divalent groups in L ^H1 , divalent heterocyclic groups are preferably furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole , phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracene, diazaanthracene, azaphenanthrene, diazaphenanthrene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, directly bonded to a ring-constituting atom (preferably a carbon atom) of benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindolocarbazole, diazaindolocarbazole, azaindenocarbazole or diazaindenocarbazole; more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9, 10-dihydroacridine, 5,10-dihydrophenazine, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindolocarbazole, diazaine dolocarbazole, azaindenocarbazole or diazaindenocarbazole without two hydrogen atoms directly bonded to atoms (preferably carbon atoms) constituting the ring, more preferably pyridine, diazabenzene, triazine, Ring-constituting atoms (preferably carbon atoms) of azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine ) excluding two hydrogen atoms directly bonded to ), particularly preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, or carbazole atoms forming a ring (preferably carbon atoms ) in which two hydrogen atoms are directly bonded to ), and particularly preferably a group in which two hydrogen atoms are directly bonded to a ring-constituting atom (preferably a carbon atom) from dibenzofuran, dibenzothiophene or carbazole. and these groups may have a substituent.

In the divalent group for L ^H1 , the alkylene group is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.

Examples and preferred ranges of substituents that L ^H1 may have are the same as examples and preferred ranges of substituents that Ar ^H1 and Ar ^H2 may have.

In the divalent group for L ^H1 , R ⁰ 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, An aryl group is more preferable, and these groups may have a substituent.
Examples and preferred ranges of the aryl group and monovalent heterocyclic group for R ⁰ in the divalent group for L ^H1 are the examples and preferred ranges for the aryl group and monovalent heterocyclic group for Ar ^H1 and Ar ^H2 , respectively. is the same as
In the divalent group L ^H1 , examples and preferred ranges of substituents R ⁰ may have are the same as examples and preferred ranges of substituents Ar ^H1 and Ar ^H2 may have. .

n ^H1 is usually an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 7 or less, more preferably an integer of 1 or more and 5 or less, and still more preferably an integer of 1 or more and 3 or less, 1 or 2 is particularly preferred.

Ar ^H1 and Ar ^H2 may be directly bonded or bonded via a divalent group to form a ring, but the compound represented by formula (H-1) is easy to synthesize. Therefore, it is preferred not to form a ring.
When Ar ^H1 and Ar ^H2 are bonded via a divalent group to form a ring, the divalent group is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent hetero A cyclic group, a group represented by -N(R ⁰ )-, a group represented by -(O=)P(R ⁰ )-, a group represented by -O-, a group represented by -S- , a group represented by -S(=O) ₂ - or a group represented by -C(=O)-, more preferably an alkylene group, a cycloalkylene group, or a group represented by -N(R ⁰ )- a group represented by -O- or a group represented by -S-, more preferably an alkylene group, a group represented by -O- or a group represented by -S- , these groups may have a substituent.
When Ar ^H1 and Ar ^H2 are bonded via a divalent group to form a ring, examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in the divalent group are They are the same as the examples and preferred ranges of the arylene group, divalent heterocyclic group and alkylene group in L ^H1 , respectively.
When Ar ^H1 and Ar ^H2 are bonded through a divalent group to form a ring, examples and preferred ranges of R ⁰ in the divalent group are R ⁰ in the divalent group of L ^H1 is the same as the example and preferred range of
When Ar ^{1 H1} and Ar 2 ^H2 are bonded via a divalent group to form a ring, examples and preferred ranges of substituents that the divalent group may have include Ar ^H1 and Ar It is the same as the example and preferred range of the substituent that ^H2 may have.

L ^{1 H1} and Ar ^{1 H1} may be directly bonded or bonded via a divalent group to form a ring, but the compound represented by formula (H-1) is easy to synthesize. Therefore, it is preferred not to form a ring. Examples and preferred ranges of the divalent group in the case where L ^H1 and Ar ^H1 are bonded via a divalent ^group to form ^a ring are: are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.
L ^H1 and Ar ^H2 may be directly bonded or bonded via a divalent group to form a ring, but the compound represented by formula (H-1) is easily synthesized. Therefore, it is preferred not to form a ring. Examples and preferred ranges of ^{the divalent group in the case where L H1 and Ar H2 are bonded} via a divalent group to form a ^ring are: are the same as the examples and preferred ranges of the divalent group in the case of forming a ring by combining with each other.

Examples of the compound represented by formula (H-1) include compounds represented by the following formula.

(First polymer compound)
The first polymer compound is a polymer compound containing at least one structural unit selected from the group consisting of structural units represented by formula (X) and structural units represented by formula (Y).
The first polymer compound is preferably a polymer compound different from the polymer compound (A) and the polymer compound (B), and is a polymer compound that does not contain the structural unit (A) and the structural unit (B). is more preferable.

The first polymer compound preferably contains a structural unit represented by formula (Y), since the driving voltage of the light-emitting device of the present disclosure is lower.
When the first polymer compound contains a structural unit represented by formula (Y), the content of the structural unit represented by formula (Y) contained in the first polymer compound is Any range is acceptable as long as it functions as a molecular compound. When the first polymer compound contains a structural unit represented by formula (Y), the content of the structural unit represented by formula (Y) contained in the first polymer compound is For example, it is 1 to 100 mol% with respect to the total content of structural units contained in the molecular compound, and is preferably 10 to 100 mol% because the driving voltage of the light-emitting device of the present disclosure is lower, It is more preferably 30 to 100 mol %, still more preferably 50 to 100 mol %, particularly preferably 70 to 100 mol %, particularly preferably 90 to 100 mol %.
In the first polymer compound, the structural unit represented by the formula (Y) may be contained alone or in combination of two or more.

The first polymer compound contains a structural unit represented by formula (X) because the first polymer compound has excellent hole-transport properties and the driving voltage of the light-emitting device of the present disclosure is lower. is preferred.
When the first polymer compound contains a structural unit represented by formula (X), the content of the structural unit represented by formula (X) contained in the first polymer compound is Any range is acceptable as long as the function as a molecular compound is exhibited. When the first polymer compound contains a structural unit represented by formula (X), the content of the structural unit represented by formula (X) contained in the first polymer compound is For example, it is 0.01 to 100 mol% with respect to the total content of the structural units contained in the molecular compound, the hole transport property of the first polymer compound is excellent, and the light emitting device of the present disclosure is obtained. Since the driving voltage becomes lower, it is preferably 0.05 to 90 mol%, more preferably 0.1 to 70 mol%, still more preferably 0.2 to 50 mol%, particularly preferably 0 .5 to 30 mol %, particularly preferably 1 to 10 mol %.
In the first polymer compound, the structural unit represented by formula (X) may be contained alone or in combination of two or more.

Since the first polymer compound has an excellent hole-transport property and the driving voltage of the light-emitting device of the present disclosure is further lowered, the structural unit represented by formula (Y) and the formula It preferably contains a structural unit represented by (X).
When the first polymer compound contains a structural unit represented by the formula (Y) and a structural unit represented by the formula (X), it is represented by the formula (Y) contained in the first polymer compound The total content of the structural units and the structural units represented by formula (X) may be within a range in which the function as the first polymer compound can be exhibited. When the first polymer compound contains a structural unit represented by the formula (Y) and a structural unit represented by the formula (X), it is represented by the formula (Y) contained in the first polymer compound The total content of the structural units and the structural units represented by the formula (X) is, for example, 1 to 100 mol%, the hole transport property of the first polymer compound is excellent, and the light emission of the present disclosure Since the drive voltage of the device is further lowered, it is preferably 10 to 100 mol%, more preferably 30 to 100 mol%, even more preferably 50 to 100 mol%, and particularly preferably 70 to 100 mol%. and particularly preferably 90 to 100 mol %.

The arylene group represented by the structural unit Ar ^Y1 represented by the formula (Y) is preferably monocyclic or bicyclic to hexacyclic because the driving voltage of the light-emitting device of the present disclosure is lower. A group obtained by removing two hydrogen atoms directly bonded to atoms constituting a ring from an aromatic hydrocarbon, more preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon, A group in which two hydrogen atoms directly bonded to the constituent atoms are removed, more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, and two hydrogen atoms directly bonded to the ring-constituting atoms are removed. is a group from which benzene, phenanthrene, dihydrophenanthrene or fluorene is removed, and particularly preferably a group from which two hydrogen atoms directly bonded to atoms constituting the ring are removed from benzene, phenanthrene, dihydrophenanthrene or fluorene; may
The divalent heterocyclic group represented by Ar 2 ^Y1 is preferably selected from monocyclic or bicyclic to hexacyclic heterocyclic compounds, since the driving voltage of the light-emitting device of the present disclosure is lower. is a group excluding two hydrogen atoms that are directly bonded to the atoms that constitute a group with two hydrogen atoms removed, more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10 - A group obtained by removing two hydrogen atoms directly bonded to a ring-constituting atom (preferably a carbon atom or a nitrogen atom, more preferably a carbon atom) from dihydrophenazine, particularly preferably pyridine, diazabenzene, triazine, A group obtained by removing two hydrogen atoms directly bonded to a ring-constituting atom (preferably a carbon atom or a nitrogen atom, more preferably a carbon atom) from carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, and The group may have a substituent.
In the divalent group in which at least one arylene group and at least one divalent heterocyclic group represented by Ar ^Y1 are directly bonded, the preferred ranges of the arylene group and the divalent heterocyclic group are, respectively, It is the same as the preferred range of the arylene group and divalent heterocyclic group represented by Ar ^Y1 .

In Ar ^Y1 , the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" includes, for example, groups represented by the following formulae, The group may have a substituent.

Ar ^{2 Y1} is preferably an optionally substituted arylene group because the driving voltage of the light-emitting device of the present disclosure is lower.

The substituent that the group represented by Ar ^Y1 may have 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 or a fluorine atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group or a cycloalkyl A group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.
The aryl group in the substituent that the group represented by Ar ^Y1 may have is preferably a monocyclic or bicyclic to hexacyclic aromatic group because the driving voltage of the light-emitting element of the present disclosure is lower. a group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from a group hydrocarbon, more preferably a monocyclic, bicyclic or tricyclic aromatic hydrocarbon more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene or fluorene, excluding one hydrogen atom directly bonded to a ring-constituting atom. and particularly preferably a group obtained by removing one hydrogen atom directly bonded to a ring-constituting atom from benzene, phenanthrene, dihydrophenanthrene or fluorene, and these groups further have a substituent. may
The monovalent heterocyclic group in the substituent that the group represented by Ar ^Y1 may have is preferably monocyclic or bicyclic to 6 A group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from a cyclic heterocyclic compound, more preferably a monocyclic, bicyclic or tricyclic heterocyclic compound , a group in which one hydrogen atom directly bonded to a ring-constituting atom is removed, more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine, excluding one hydrogen atom directly bonded to an atom (preferably a carbon atom or a nitrogen atom) constituting a ring, particularly preferably pyridine, diazabenzene, triazine, carbazole, dibenzofuran, dibenzothiophene, phenoxazine or phenothiazine, with one hydrogen atom directly bonded to a ring-constituting atom (preferably a carbon atom or a nitrogen atom) removed, and these groups are Furthermore, it may have a substituent.
In the substituted amino group in the substituent that may be possessed by the group represented by Ar ^Y1 , the substituent possessed by the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group. The group may further have a substituent. Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent of the amino group are the aryl group and monovalent heterocyclic group in the substituent that the group represented by Ar ^Y1 may have, respectively. is the same as the example and preferred range of

The substituent that the group represented by Ar ^Y1 may further have preferably has an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, monovalent heterocyclic group, substituted amino group or fluorine atom, more preferably alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group or substituted amino group, still more preferably alkyl group, a cycloalkyl group or an aryl group, particularly preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent, but preferably have no further substituent. .
Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the group represented by Ar Y1 may further have are ^{Ar Y1} are the same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that the group may have.

The structural unit represented by formula (Y) is preferably a structural unit represented by formula (Y-1) or formula (Y-2) because the driving voltage of the light-emitting device of the present disclosure is lower. .

[In the formula,
R ^Y1 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 fluorine atom, and these groups are substituents may have 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 atoms to which they are bonded. A plurality of R ^Y1 may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
X ^Y1 represents a group represented by -C(R ^Y2 ) ₂ -, -C(R ^Y2 )=C(R ^Y2 )- or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -. R ^Y2 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 fluorine atom, and these groups are substituents may have 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 atoms to which they are bonded. A plurality of ^RY2 may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

R ^Y1 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, a cycloalkyl group or an aryl group. more preferably a hydrogen atom or an alkyl group, and these groups may have a substituent.

In formula (Y-1), at least one of R ^{1 Y1} (preferably at least two of R ^{1 Y1} ) is preferably an alkyl group, a cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or fluorine atom, more preferably alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group It is a cyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group or an aryl group, particularly preferably an alkyl group, and these groups may have a substituent.

R ^Y2 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, since the driving voltage of the light emitting device of the present disclosure is lower. , more 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 have substituents. may

Examples and preferred ranges of ^the aryl group, monovalent heterocyclic group and substituted amino group for R ^Y1 and R ^Y2 are, respectively, the aryl group and the monovalent It is the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.
Examples and preferred ranges of substituents that R ^Y1 and R ^Y2 may have are the same as examples and preferred ranges of substituents that the group represented by Ar ^Y1 may have.

X ^Y1 is preferably a group represented by -C(R ^Y2 ) ₂ - or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -, since the driving voltage of the light-emitting element of the present disclosure is lower. and more preferably a group represented by —C(R ^Y2 ) ₂ —.

Examples of structural units represented by formula (Y) include structural units comprising at least one arylene group represented by formulas (Y-101) to (Y-141), formulas (Y-201) to A structural unit consisting of at least one divalent heterocyclic group represented by formula (Y-209), at least one arylene group represented by formulas (Y-301) to (Y-306) and at least Structural units composed of a divalent group directly bonded to one type of divalent heterocyclic group can be mentioned.

Structural units a ^X1 and a ^X2 represented by formula (X) are usually integers of 0 to 10, and are preferably integers of 0 to 5 because the driving voltage of the light-emitting device of the present disclosure is lower. , more preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1.

R ^X1 , R ^X2 and R ^X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, because the driving voltage of the light-emitting device of the present disclosure is lower. or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.
Examples and preferred ranges of the aryl group and the monovalent heterocyclic group in R ^X1 , R ^X2 and R ^X3 are, respectively, the aryl group and the monovalent heterocyclic group in the substituent that the group represented by Ar ^Y1 may have. It is the same as the example and preferred range of the cyclic group.

Ar ^X1 , Ar ^X2 , Ar ^X3 and Ar ^X4 are preferably arylene groups optionally having substituents, since the driving voltage of the light-emitting device of the present disclosure becomes lower.
Examples and preferred ranges of the arylene group and divalent heterocyclic group for Ar ^X1 , Ar ^X2 , Ar ^X3 and Ar ^X4 are the same as the examples and preferred ranges of the arylene group and divalent heterocyclic group for Ar ^Y1 respectively. be.
Examples and preferred arylene groups and divalent heterocyclic groups in the divalent group in which at least one arylene group and at least one divalent heterocyclic group represented by Ar ^X2 and Ar ^X4 are directly bonded The ranges are the same as the examples and preferred ranges of the arylene group and the divalent heterocyclic group in Ar ^Y1 , respectively.
The divalent group in which at least one arylene group and at least one divalent heterocyclic group in Ar ^X2 and Ar ^X4 are directly bonded includes at least one arylene group and at least one divalent heterocyclic group in Ar ^Y1 . Examples thereof include the same divalent groups to which a valent heterocyclic group is directly bonded.

Examples and preferred ranges of the substituents that the groups represented by Ar ^X1 to Ar ^X4 and R ^X1 to R ^X3 may have are the examples and preferred ranges of the substituents that the group represented by Ar ^Y1 may have. Same as range.

Examples of structural units represented by formula (X) include structural units represented by the following formulas.

Examples of the first polymer compound include polymer compounds HP-1 to HP-3.

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

The first polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, or a graft copolymer. It is preferably a copolymer obtained by copolymerizing monomers.
The polystyrene equivalent number average molecular weight of the first polymer compound is preferably 5×10 ³ to 1×10 ⁶ , more preferably 1×10 ⁴ to 5×10 ⁵ , still more preferably 2×10 ⁴ to 2×10 ⁵ . The polystyrene equivalent weight average molecular weight of the first polymer compound is preferably 1×10 ⁴ to 2×10 ⁶ , more preferably 2×10 ⁴ to 1×10 ⁶ , still more preferably 5×10 ⁴ to 5×10 ⁵ .

(Method for producing first polymer compound)
The first polymer compound can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), Suzuki reaction, Yamamoto , Buchwald reaction, Stille reaction, Negishi reaction, Kumada reaction, and other coupling reactions using a transition metal catalyst.
In the above polymerization method, the method of charging the monomers includes a method of charging the entire amount of the monomers into the reaction system at once, a method of charging a part of the monomers and reacting them, and then charging the remaining monomers all at once. Examples thereof include a method of continuously or dividedly charging, a method of continuously or dividingly charging a monomer, and the like.
Examples of transition metal catalysts include palladium catalysts and nickel catalysts.
The post-treatment of the polymerization reaction is performed by a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and drying it. method, etc., is performed singly or in combination. When the purity of the first polymer compound is low, it can be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

[Other ingredients]
The composition of the present disclosure comprises a compound (A), a compound (B), a first compound, a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, an antioxidant and It may be a composition containing at least one selected from the group consisting of solvents. However, the hole-transporting material, hole-injecting material, electron-transporting material, electron-injecting material, and light-emitting material are different from the compound (A), the compound (B), and the first compound.

A composition containing the compound (A), the compound (B), the first compound, and a solvent (hereinafter referred to as "ink") can be prepared by, for example, a spin coating method, a casting method, or a microgravure coating method. , gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method It is suitable for fabricating a light-emitting device using, for example.
The viscosity of the ink may be adjusted depending on the type of printing method, but when applying to a printing method such as an inkjet printing method in which a solution passes through an ejection device, it is necessary to prevent clogging and flight deflection during ejection. , preferably 1 mPa·s to 20 mPa·s at 25°C.

The solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of solvents include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate and phenyl acetate. polyhydric alcohol solvents such as ethylene glycol, glycerin, and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N , and N-dimethylformamide. A solvent may be used individually by 1 type, or may use 2 or more types together.

In the ink, the content of the solvent is usually 1000 parts by mass to 1000000 parts by mass when the total content of the compound (A), the compound (B) and the first compound is 100 parts by mass.

(Hole transport material)
Hole-transporting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds. The hole-transporting material may have a cross-linking group.
Examples of low-molecular-weight compounds include triphenylamine and its derivatives, N,N'-di-1-naphthyl-N,N'-diphenylbenzidine (α-NPD), and N,N'-diphenyl-N, Aromatic amine compounds such as N'-di(m-tolyl)benzidine (TPD) can be mentioned.
Polymer compounds include, for example, polyvinylcarbazole and derivatives thereof; polyarylenes and derivatives thereof having aromatic amine structures in side chains or main chains. The polymer compound may be a compound having electron-accepting moieties such as fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene and trinitrofluorenone bound thereto.
In one embodiment of the composition of the present disclosure, when a hole-transporting material is included, the content of the hole-transporting material is the total content of the compound (A), the compound (B), and the first compound. When 100 parts by mass, it is usually 1 to 1000 parts by mass.
The hole transport materials may be used singly or in combination of two or more.

(Electron transport material)
Electron transport materials are classified into low-molecular-weight compounds and high-molecular-weight compounds. The electron transport material may have a cross-linking group.
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.
Polymer compounds include, for example, polyphenylene, polyfluorene, and derivatives thereof. The polymeric compounds may be doped with metals.
In one embodiment of the composition of the present disclosure, when an electron-transporting material is included, the content of the electron-transporting material is the total content of the compound (A), the compound (B), and the first compound, which is 100 mass When expressed as parts, it is usually 1 to 1000 parts by mass.
The electron transport materials may be used singly or in combination of two or more.

(Hole injection material and electron injection material)
Hole-injecting materials and electron-injecting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds, respectively. The hole-injecting material and the electron-injecting material may have cross-linking groups.
Examples of low-molecular 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.
Polymer compounds include, for example, polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain; and a flexible polymer.
In one embodiment of the composition of the present disclosure, when a hole-injection material and/or an electron-injection material is included, the content of the hole-injection material and the electron-injection material is, respectively, compound (A) and compound (B) When the total content of and the first compound is 100 parts by mass, it is usually 1 to 1000 parts by mass.
Each of the hole injection material and the electron injection material may be used alone or in combination of two or more.

- Ion doping The hole-injecting material or the electron-injecting material may be doped with ions. For example, if the hole-injecting material or electron-injecting material comprises a conductive polymer, the electrical conductivity of the conductive polymer is preferably between 1×10 ⁻⁵ S/cm and 1×10 ³ S/cm. The conductive polymer can be doped with an appropriate amount of ions in order to set the electrical conductivity of the conductive polymer within this range.
The type of ions to be doped into the hole injection material or the electron injection material is, for example, an anion for the hole injection material, and a cation for the electron injection material. Anions include, for example, polystyrene sulfonate, alkylbenzene sulfonate, and camphor sulfonate. Cations include, for example, lithium ion, sodium ion, potassium ion and tetrabutylammonium ion.
Ions for doping may be used alone or in combination of two or more.

(Luminous material)
Light-emitting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds. The luminescent material may have a cross-linking group.
Examples of low-molecular-weight compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and phosphorescent compounds having iridium, platinum, or europium as a central metal.
Examples of polymer compounds include polymer compounds containing structural units represented by formula (Y) and/or structural units represented by formula (X).

Examples of the phosphorescent compound include metal complexes shown below.

In one embodiment of the composition of the present disclosure, when a light-emitting material is included, the content of the light-emitting material is 100 parts by mass of the total content of the compound (A), the compound (B), and the first compound. When used, it is usually 1 to 1000 parts by mass.
A luminescent material may be used individually by 1 type, or may use 2 or more types together.

(Antioxidant)
The antioxidant may be a compound that is soluble in the same solvent as the compound (A), the compound (B), and the first compound and does not inhibit light emission and charge transport. system antioxidants and the like.
In one embodiment of the composition of the present disclosure, when an antioxidant is included, the content of the antioxidant is the total content of the compound (A), the compound (B), and the first compound, which is 100 mass When expressed as parts, it is usually 0.001 to 10 parts by mass.
Antioxidants may be used singly or in combination of two or more.

<Membrane>
The membranes of the present disclosure contain the compositions of the present disclosure described above.
The film of the present disclosure is suitable as a light-emitting layer in a light-emitting device. The membranes of the present disclosure can be made by wet methods, using inks, for example. In addition, the film of the present disclosure can be produced, for example, by a dry method such as a vacuum deposition method. Methods for producing the film of the present disclosure by a dry method include, for example, a method of vapor-depositing the composition described above and a method of co-depositing compound (A), compound (B), and the first compound.
The film thickness is typically between 1 nm and 10 μm.

<Light emitting element>
The light-emitting device of the present disclosure contains the composition described above.
A light-emitting device of the present disclosure may comprise, for example, an anode, a cathode, and an organic layer containing the composition described above provided between the anode and the cathode.

[Layer structure]
The layer containing the composition of the present disclosure is usually one or more layers selected from the group consisting of a light-emitting layer, a hole-transporting layer, a hole-injecting layer, an electron-transporting layer and an electron-injecting layer, preferably This is the light-emitting layer. These layers each contain 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 from a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material using the same method as for the above-described films.

A 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 device of the present disclosure preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light emitting layer. From the viewpoint of injection properties and electron transport properties, it is preferable to have at least one layer of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.

Materials for the hole-transporting layer, electron-transporting layer, light-emitting layer, hole-injecting layer, and electron-injecting layer include, in addition to the composition of the present disclosure, the hole-transporting material, electron-transporting material, light-emitting material, and electron-injecting layer described above, respectively. Examples include hole-injecting materials and electron-injecting materials.

The materials for the hole-transporting layer, the electron-transporting layer, and the light-emitting layer are selected from the solvents used in forming the layers adjacent to the hole-transporting layer, the electron-transporting layer, and the light-emitting layer, respectively, in the manufacture of the light-emitting device. When dissolved, it is preferred that the material has cross-linking groups to avoid dissolving the material in the solvent. After forming each layer using a material having a cross-linking group, the layer can be made insoluble by cross-linking the cross-linking group.

In the light-emitting device of the present disclosure, as a method for forming each layer such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, when using a low-molecular compound, for example, vacuum deposition from powder Dry methods such as methods, wet methods such as methods by film formation from a solution or a molten state, and wet methods such as methods by film formation from a solution or a molten state, for example, when using a polymer compound. . The order, number and thickness of the layers to be laminated are adjusted in consideration of, for example, driving voltage and the like.

[Substrate/Electrode]
The substrate in the light emitting device may be a substrate on which an electrode can be formed and which does not change chemically when the organic layer is formed. In the case of opaque substrates, it is preferred that the electrodes furthest from the substrate be transparent or translucent.
Examples of materials for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium-tin-oxide (ITO), indium-zinc-oxide, etc. conductive compounds of; silver-palladium-copper composite (APC); NESA, gold, platinum, silver, copper.
Examples of cathode materials include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, and indium; alloys of two or more of them; alloys of one or more species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, tin; and graphite and graphite intercalation compounds. Examples of 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.
Each of the anode and the cathode may have a laminated structure of two or more layers.

[Use]
The light-emitting element of the present disclosure is suitable as a light source for backlight of a liquid crystal display device, a light source for illumination, organic EL lighting, a display device such as a computer, a television, and a mobile terminal (e.g., an organic EL display and an organic EL television). can be used.

Hereinafter, one embodiment of the present disclosure will be described in more detail with reference to Examples, but the present disclosure is not limited to these Examples.

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 a mobile phase. In addition, each measurement condition of SEC is as follows.
A polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL of the solution was injected into SEC. Mobile phase was run at a flow rate of 2.0 mL/min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as a detector.

LC-MS was measured by the following method.
A sample to be measured was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg/mL, and about 1 μL was injected into an LC-MS (manufactured by Agilent, trade name: 1100LCMSD). The mobile phase for LC-MS was acetonitrile and tetrahydrofuran with varying ratios and flowed at a flow rate of 0.2 mL/min. The column used was L-column 2 ODS (3 μm) (manufactured by Chemicals Evaluation and Research Institute, inner diameter: 2.1 mm, length: 100 mm, particle size: 3 μm).

TLC-MS was measured by the following method.
The measurement sample is dissolved in any solvent of toluene, tetrahydrofuran and chloroform at an arbitrary concentration, applied to a DART TLC plate (manufactured by Techno Applications, trade name: YSK5-100), and subjected to TLC-MS (JEOL Ltd. The measurement was performed using a JMS-T100TD (The AccuTOF TLC) manufactured by Manufacture, trade name. The helium gas temperature during measurement was adjusted in the range of 200 to 400.degree.

NMR was measured by the following method.
5 to 10 mg of a measurement sample was added to about 0.5 mL of heavy chloroform (CDCl ₃ ), heavy tetrahydrofuran, heavy dimethylsulfoxide, heavy acetone, heavy N,N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol. Or dissolved in methylene dichloride, NMR equipment (manufactured by Agilent, trade name: INOVA300 or MERCURY
400 VX).

High performance liquid chromatography (HPLC) area percentage values were used as an index of compound purity. Unless otherwise specified, this value is the value at UV=254 nm in HPLC (trade name: LC-20A, manufactured by Shimadzu Corporation). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform to a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL was injected into the HPLC depending on the concentration. Acetonitrile/tetrahydrofuran was used as the mobile phase for HPLC while changing the ratio from 100/0 to 0/100 (volume ratio), and flowed at a flow rate of 1.0 mL/min. The column was a Kaseisorb LC ODS
2000 (manufactured by Tokyo Kasei Kogyo Co., Ltd.) or an ODS column having equivalent performance was used. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as the detector.

Calculation of the _ΔEST value of the compound was performed as follows.
First, the ground state of the compound was structurally optimized by density functional theory at the B3LYP level. At that time, 6-31G* was used as a basis function.
Then, using the obtained optimized structure, _ΔEST of the compound was calculated by time-dependent density functional theory at the B3LYP level. The calculation was performed using Gaussian09 as a quantum chemical calculation program.

The maximum peak wavelength of the emission spectrum of the compound at room temperature was measured at room temperature with a spectrophotometer (manufactured by JASCO Corporation, FP-6500). A xylene solution in which a compound was dissolved in xylene at a concentration of about 8×10 ⁻⁴ mass % was used as a sample. Ultraviolet (UV) light with a wavelength of 325 nm was used as excitation light.

<Synthesis and acquisition of compounds H1 to H3, polymer compound HP4 and compound ET1>
Compounds H1 to H3, polymer compound HP4 and compound ET1 were manufactured by Luminescence Technology.

<Synthesis and acquisition of metal complexes MC1 to MC11>
Metal complexes MC1 and MC4 were synthesized according to the method described in JP-A-2013-147551.
Metal complex MC2 was synthesized according to the method described in WO2017/130977.
A metal complex MC3 (metal complex Firpic) manufactured by Luminescence Technology was used.
Metal complex MC5 was synthesized according to the method described in WO2017/170916.
Metal complexes MC6 to MC8 and MC10 were synthesized by the method described below.
Metal complex MC9 was synthesized according to the method described in WO2016/006523.
Metal complex MC11 was synthesized according to the methods described in WO2008/090795 and WO2006/121811.

<Synthesis of metal complex MC6>
A metal complex MC6 was synthesized by the following method.

After making the inside of the reaction vessel an argon atmosphere, 2,2'-dimethylhexanoic acid (23.8 g), chloroform (143 mL), and N,N'-dimethylformamide (0.12 g) were added and stirred at 50°C. bottom. Thionyl chloride (21.6 g) was added dropwise thereto, and the mixture was stirred at 50°C for 3 hours to generate 2,2'-dimethylhexanoyl chloride.
After a nitrogen gas atmosphere was created in a separately prepared reaction vessel, 5-bromo-2-methylaniline (29.3 g), chloroform (293 mL), and triethylamine (21.9 mL) were added and stirred. After that, the reaction vessel was cooled with an ice bath, and 2,2'-dimethylhexanoyl chloride prepared above was added dropwise thereto. After the dropwise addition, stirring was continued at room temperature for 2.5 hours, then 1 mol/L sodium carbonate aqueous solution (165 mL) was added and the mixture was stirred at room temperature. After liquid separation, 1 mol/L hydrochloric acid (83 mL) was added to the obtained organic layer and the mixture was stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, recrystallized twice using heptane, and dried under reduced pressure at 40° C. to obtain compound MC6A (39 g, white solid) with a yield of 76%. The HPLC area percentage value of compound MC6A was 98.7%.

The NMR measurement results of compound MC6A were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 8.06 (1H, d), 7.25-7.11 (2H, m), 7.04 (1H, d), 2.17 ( 3H, s), 1.60-1.53 (2H, m), 1.32-1.22 (10 H, m), 0.87 (3H, s).

After making the inside of the reaction vessel an argon gas atmosphere, compound MC6A (25 g), monochlorobenzene (200 mL), 2-fluoropyridine (7.6 mL) and trifluoromethanesulfonic anhydride (15 mL) were added, and the mixture was stirred at room temperature for 30 minutes. Stirred. Benzoyl hydrazine (12 g) was added thereto, and the mixture was stirred at 90° C. for 3.5 hours. After that, ion-exchanged water (250 mL) was added thereto to wash the organic layer. After liquid separation, a 1 mol/L sodium hydrogencarbonate aqueous solution (66 mL) was added to the obtained organic layer to extract the organic layer, and the obtained organic layer was washed with ion-exchanged water. An oily matter was obtained by concentrating the obtained organic layer under reduced pressure. A mixed solvent of chloroform and THF (volume ratio: 8:2, 50 mL) was added to the resulting oil to dissolve it, followed by filtration through a filter lined with silica gel, and the resulting filtrate was concentrated under reduced pressure. After that, it was recrystallized using heptane and dried at 50° C. under reduced pressure to obtain compound MC6B (27.3 g) as a white solid with a yield of 83%. The HPLC area percentage value of compound MC6B was 99.1%.

The NMR measurement results of compound MC6B were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 7.58-7.50 (2H, m), 7.35-7.22 (5H, m), 7.12-7.07 (1H , d), 1.71 (3H, s), 1.67-1.57 (1H, m), 1.45-1.07 (11H, m), 0.88 (3H, t).

After making the inside of the reaction vessel an argon gas atmosphere, compound MC6B (7.0 g), 2-([1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3 , 2-dioxaborolan (5.2 g) and toluene were added and stirred at room temperature. Bis(di-tert-butyl(4-dimethylaminobiphenyl)phosphine)dichloropalladium (60 mg) was added thereto and heated to 80°C. After that, a 40% by mass tetrabutylammonium aqueous solution (66 g) was added dropwise, and the mixture was stirred at 80° C. for 16 hours. After that, the reaction vessel was cooled to room temperature and separated. The obtained organic layer was washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was washed with ion-exchanged water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. Activated carbon was added to the obtained filtrate, and the mixture was stirred at room temperature for 30 minutes and then filtered through a filter covered with celite. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and ethyl acetate (volume ratio 9:1). Thereafter, recrystallization was performed three times using a mixed solvent of heptane and 2-propanol (volume ratio: 5:1), followed by drying at 50°C under reduced pressure to obtain compound MC6C (5.5 g, white solid) with a yield of 66%. I got it in The HPLC area percentage value of compound MC6C was greater than 99.5%.

The measurement results of LC-MS and NMR of compound MC6C were as follows.
LC-MS (APCI, positive): m/z=542 [M+H] ^+
1 H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 7.82 (1H, t),
7.73-7.71 (2H, m), 7.64-7.57 (4H, m), 7.53 (1H, t), 7.45 (2H, t), 7.40-7. 33 (3H, m), 7.32-7.25 (2H, m), 7.22 (2H, t), 1.80 (3H, s), 1.78-1.67 (1H, m) , 1.52-1.42 (1H, m), 1.37 (3H, s), 1.35-1.16 (4H, m), 1.14 (3H, s), 0.82 (3H , t).

After the inside of the reaction vessel was replaced with an argon gas atmosphere, trisacetylacetonatoiridium (1.2 g), compound MC6C (5.0 g) and pentadecane (25 mL) were added, and the mixture was stirred under reflux with heating for 55 hours. After that, toluene was added thereto, and after filtering through a filter covered with silica gel, a yellow solution containing metal complex MC6 was extracted using a mixed solvent of toluene and ethyl acetate. The obtained solution was concentrated under reduced pressure to obtain a solid, and then the obtained solid was purified by silica gel column chromatography (mobile phase solvent: mixed solvent of toluene and ethyl acetate) to obtain a solid. The obtained solid was recrystallized using a mixed solvent of toluene and acetonitrile, and recrystallized using a mixed solvent of toluene and ethanol several times, and dried under reduced pressure at 50 ° C. to obtain metal complex MC6 (3 .5 g, yellow solid) was obtained in 82% yield. The HPLC area percentage value for metal complex MC6 was 96%.

The LC-MS and NMR measurement results of the metal complex MC6 were as follows.
LC-MS (APPI, positive): m/z = 1645.8 [M+H] ^+
1 H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.89-7.69 (9H, m), 7.67-7.31 (27H, m), 6.99-6.38 (9H, m), 6.12-6.10 (3H, m), 2.23-1.82 (9H, m), 1.47-0.84 (36H, m), 0.78-0 .46(9H, m).

<Synthesis of metal complex MC7>
A metal complex MC7 was synthesized by the following method.

After the inside of the reaction vessel was replaced with an argon atmosphere, 2,2'-dimethylhexanoic acid (11.8 g), chloroform (60 mL) and N,N'-dimethylformamide (0.07 g) were added and stirred at 50°C. Thionyl chloride (11.3 g) was added dropwise thereto, and the mixture was stirred at 50°C for 3 hours to generate 2,2'-dimethylhexanoyl chloride.
After making the inside of a separately prepared reaction vessel a nitrogen gas atmosphere, 2-methyl-5-(3-phenylphenyl)aniline hydrochloride (22.0 g), chloroform (176 mL) and triethylamine (20.7 mL) were added and stirred. bottom. After that, the reaction vessel was cooled with an ice bath, and the 2,2'-dimethylhexanoyl chloride solution prepared above was added dropwise thereto. After the dropwise addition, stirring was continued at room temperature for 2.5 hours, then 1 mol/L sodium carbonate aqueous solution (82 mL) was added and the mixture was stirred at room temperature. After liquid separation, 1 mol/L hydrochloric acid (41 mL) was added to the obtained organic layer and the mixture was stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, recrystallized using heptane, and dried under reduced pressure at 40° C. to obtain compound MC7D (27 g, white solid) with a yield of 94%. The HPLC area percentage value of compound MC7D was greater than 99.5%.

The NMR measurement results of compound MC7D were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 8.08 (1H, d), 7.91 (1H, t), 7.64 (2H, d), 7.57 (2H, t) , 7.51-7.41 (3H, m), 7.38-7.31 (2H, m), 7.28 (1H, d), 7.24 (1H, br), 2.28 (3H , s), 1.60 (2H, m), 1.37-1.30
(10H, m), 0.88 (3H, t)

After making the inside of the reaction vessel an argon gas atmosphere, compound MC7D (25 g), monochlorobenzene (84 mL), 2-fluoropyridine (2.6 mL) and trifluoromethanesulfonic anhydride (5 mL) were added, and the mixture was stirred at room temperature for 30 minutes. Stirred. 3-Bromobenzoylhydrazine (6.4 g) was added thereto and stirred at 90° C. for 4.5 hours. After that, ion-exchanged water (105 mL) and heptane (105 mL) were added thereto to wash the organic layer. After liquid separation, a 1 mol/L sodium hydrogencarbonate aqueous solution (45 mL) was added to the organic layer to extract the organic layer, and the resulting organic layer was washed with ion-exchanged water. An oily matter was obtained by concentrating the obtained organic layer under reduced pressure. A mixed solvent of chloroform and THF (volume ratio: 8:2, 50 mL) was added to the resulting oil to dissolve it, followed by filtration through a filter lined with silica gel, and the resulting filtrate was concentrated under reduced pressure. After that, it was recrystallized using heptane and dried under reduced pressure at 50° C. to obtain compound MC7E (14.3 g) as a white solid with a yield of 93%. The HPLC area percentage value of compound MC7E was greater than 99.5%.

After making the inside of the reaction vessel an argon gas atmosphere, compound MC7E (13.6 g), 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.4 g), toluene (136 mL) ) was added and stirred at room temperature. [(Di(1-adamantyl)-N-butylphosphine)-2-(2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate (175 mg) was added thereto and heated to 80°C. heated. After that, a mixed liquid of 40% by mass tetrabutylammonium aqueous solution (38 g) and ion-exchanged water (56 mL) was added dropwise, and the mixture was stirred at 80° C. for 16 hours. After that, the reaction vessel was cooled to room temperature and separated. The obtained organic layer was washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was washed with ion-exchanged water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. Silica gel (49 g) was added to the obtained filtrate, and the mixture was stirred at room temperature for 30 minutes and then filtered through a filter covered with celite. The filter top was washed with a mixed solvent of chloroform and tetrahydrofuran (volume ratio: 1). The resulting filtrate was concentrated under reduced pressure, recrystallized three times using a mixed solvent of heptane and 2-propanol (volume ratio 8:1), and dried under reduced pressure at 50°C to obtain compound MC7F (12.2 g, white solid) was obtained in 90% yield. The HPLC area percentage value of compound MC7F was greater than 99.5%.

The measurement results of LC-MS and NMR of compound MC7F were as follows.
LC-MS (APPI, positive): m/z = 562 [M+H] ^+
1 H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 7.82 (2H, t),
7.75 (1H, d), 7.63-7.60 (4H, m), 7.59-7.53 (3H, m), 7.49-7.43 (3H, m), 7. 38-7.33 (3H, m), 7.26-7.22 (5H, m), 1.80-1.73 (4H, m), 1.56-1.40 (4
H, m), 1.35-1.18 (7H, m), 0.82 (3H, t).

After the inside of the reaction vessel was replaced with an argon gas atmosphere, trisacetylacetonatoiridium (2.2 g), compound MC7F (10 g) and pentadecane (40 mL) were added, and the mixture was stirred under reflux with heating for 67 hours. After that, toluene was added thereto, and after filtering through a filter covered with silica gel, a yellow solution containing metal complex MC7 was extracted using a mixed solvent of toluene and ethyl acetate. The obtained solution was concentrated under reduced pressure to obtain a solid, and then the obtained solid was purified by silica gel column chromatography (mobile phase solvent: mixed solvent of toluene and ethyl acetate) to obtain a solid. The obtained solid was recrystallized using a mixed solvent of toluene and acetonitrile, and recrystallized using a mixed solvent of toluene and ethanol several times, and dried under reduced pressure at 50 ° C. to obtain metal complex MC7 (3 .5 g, yellow solid) was obtained in 82% yield. The HPLC area percentage value of metal complex MC7 was 99.5% or higher.

The measurement results of LC-MS and NMR of metal complex MC7 were as follows.
LC-MS (APCI, positive): m/z=1874.9 [M+H] ^+
1 H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.93-7.68 (m, 9H), 7.65-7.28 (m, 27H), 7.21-7.04 (m, 15H), 7.00-6.71 (m, 6H), 6.40-6.25 (m, 3H), 2.33-1.82 (m, 9H), 1.80-1 .54 (m, 3H), 1.48-0.80 (m, 33H), 0.79-0.32 (m, 9H).

<Synthesis of metal complex MC8>
A metal complex MC8 was synthesized by the following method.

After making the inside of the reaction vessel an argon gas atmosphere, compound MC7D (40 g), monochlorobenzene (320 mL), 2-fluoropyridine (9.8 mL) and trifluoromethanesulfonic anhydride (19 mL) were added, and the mixture was stirred at room temperature for 30 minutes. Stirred. 3-tert-Butylbenzoylhydrazine (22 g) was added thereto and stirred at 90° C. for 3.5 hours. After that, ion-exchanged water (360 mL) was added thereto to wash the organic layer. After liquid separation, a 1 mol/L sodium hydrogencarbonate aqueous solution (77 mL) was added to the obtained organic layer to extract the organic layer, and the obtained organic layer was washed with ion-exchanged water. An oily matter was obtained by concentrating the obtained organic layer under reduced pressure. A mixed solvent of chloroform and THF (volume ratio: 8:2, 90 mL) was added to the resulting oil to dissolve it, followed by filtration through a filter lined with silica gel, and the resulting filtrate was concentrated under reduced pressure. Thereafter, recrystallization was performed using a mixed solvent of heptane and 2-propanol (volume ratio 5:0.3, 295 mL), and dried under reduced pressure at 50°C to yield compound MC8G (47.6 g) as a white solid. 85% obtained. The HPLC area percentage value of compound MC8G was 99.9%.

The NMR measurement results of compound MC8G were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.79 (1H, t), 7.73 (1H, d), 7.68 (1H, dd), 7.65-7. 58 (3H, m), 7.58-7.50 (2H, m), 7.48-7.40 (3H, m), 7.35 (1H, tt), 7.33-7.27 ( 2H, m), 7, 23-7.18 (2H, m), 1.80 (3H, s), 1.78-1.68 (1H, m), 1.53-1.41 (1H, m), 1.38 (3H, s), 1.35-1.18 (4H, m), 1.16 (3H, s), 1.06 (9H, s), 0.81 (3H, t ).
TLC-MS (positive): m/z=542.3 [M+H] ⁺

After the inside of the reaction vessel was replaced with an argon gas atmosphere, trisacetylacetonatoiridium (1.5 g), compound MC8G (6.8 g) and pentadecane (34 mL) were added, and the mixture was stirred under heating under reflux for 30 hours. After that, toluene was added thereto, and after filtering through a filter covered with silica gel, a yellow solution containing metal complex MC8 was extracted using a mixed solvent of toluene and ethyl acetate. The obtained solution was concentrated under reduced pressure to obtain a solid, and then the obtained solid was purified by silica gel column chromatography (mobile phase solvent: mixed solvent of toluene and ethyl acetate) to obtain a solid. The obtained solid was recrystallized several times using a mixed solvent of heptane and 2-propanol, and dried under reduced pressure at 50°C to obtain metal complex MC8 (4.3 g, yellow solid) with a yield of 75%. rice field. The HPLC area percentage value of metal complex MC8 was 94%.

The measurement results of LC-MS and NMR of metal complex MC8 were as follows.
TLC-MS (positive): m/z=1814.7 [M+H] ^+
1 H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.89-7.28 (72H, m), 6.95-6.30 (6H, m), 6.02-6.20 (3H, m), 2.23-0.50 (45H, m).

<Synthesis of metal complex MC10>
Metal complex MC10 was synthesized by the following method.

After making the inside of the reaction vessel an argon gas atmosphere, 2,6-dimethyl-4-tert-butylphenylhydrazine hydrochloride (101 g) and tert-butyl methyl ether (1070 mL) were added, and the reaction vessel was placed in an ice bath. cooled. After that, an aqueous sodium hydroxide solution (1 mol/L, 1330 mL) was added thereto, and the mixture was stirred for 30 minutes while cooling the reaction vessel in an ice bath. The organic layer of the resulting reaction solution was extracted to obtain a tert-butyl methyl ether solution as the organic layer.
After the inside of a separately prepared reaction vessel was filled with an argon gas atmosphere, compound MC10-c (145 g) and chloroform (3200 mL) were added, and the reaction vessel was placed in an ice bath for cooling. Then, the tert-butyl methyl ether solution obtained above was added thereto. After that, the reaction vessel was stirred for 7 hours while cooling in an ice bath, and then stirred at room temperature for 70 hours. Ion-exchanged water (3200 mL) was added to the resulting reaction solution, the organic layer was extracted, toluene (500 mL) was added, and the organic layer was partially concentrated under reduced pressure to obtain a toluene solution. The resulting toluene solution was purified by silica gel column chromatography (mobile phase solvent: toluene solvent), and then recrystallized twice using a mixed solvent of ethanol and methanol (mass ratio 1:1). After that, by drying under reduced pressure at 50°C, compound (H) (129 g, yield 66%) was obtained as a white solid. The HPLC area percentage value of compound (H) was 99.5% or more.

The measurement results of LC-MS and NMR of compound (H) were as follows.
LC-MS (ESI, positive): m/z=542.4 [M+H] ^+
1 H-NMR (CDCl ₃ , 400 MHz): δ (ppm) = 7.90 (2H, s), 7.80 (1H, d), 7.58-7.55 (1H, m), 7.48 (1H, d), 7.
38 (1H, t), 7.27-7.10 (3H, m), 2.35 (6H, s), 1.94 (6H, s), 1.34 (9H, s).

After making the inside of the reaction vessel an argon gas atmosphere, compound (H) (87 g), 4-tert-butylphenylboronic acid (35 g), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium ( II) (1.3 g), toluene (1500 mL) and 20 mass % tetrabutylammonium hydroxide aqueous solution (555 g) were added, and the mixture was stirred under reflux with heating for 4 hours. After cooling to room temperature, ion-exchanged water was added thereto, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water to obtain an organic layer. After drying the obtained organic layer with anhydrous sodium sulfate, silica gel (170 g) was added and filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The resulting solid was recrystallized twice using a mixed solvent of ethyl acetate and acetonitrile (volume ratio 1:1). Then, it was dried under reduced pressure at 50° C. to obtain compound (I) (73 g, yield 76%) as a white solid. The HPLC area percentage value of compound (I) was 99.5% or more.

The LC-MS measurement results of compound (I) were as follows.
LC-MS (ESI, positive): m/z = 486.3 [M+H] ⁺

After making the inside of the reaction vessel an argon gas atmosphere, iridium chloride n-hydrate (10.1 g), compound (I) (32.3 g), ion-exchanged water (81 mL) and diglyme (253 mL) were added, and the mixture was heated at 140°C. The mixture was heated and stirred for 48 hours. After that, toluene was added thereto and washed with ion-exchanged water to obtain an organic layer. A solid was obtained by concentrating the obtained organic layer under reduced pressure. The resulting solid was purified by silica gel chromatography (mobile phase solvent: mixed solvent of toluene and ethanol). Then, it was dried under reduced pressure at 50° C. to obtain a yellowish brown solid (38.0 g).
After an argon gas atmosphere was created in a separately prepared reaction vessel, the solid obtained above (30.8 g), silver trifluoromethanesulfonate (11.2 g), compound (I) (19.7 g), and diphenyl ether (76 mL) were mixed. ) and 2,6-lutidine (16.9 mL) were added, and the mixture was heated and stirred at 165° C. for 50 hours. After that, the mixture was cooled to room temperature, toluene was added, and the mixture was filtered through a filter covered with celite. Silica gel (228 g) was added to the obtained filtrate, the obtained filtrate was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a yellow liquid. . Hexane (760 mL) was added to the resulting liquid, and the mixture was stirred at 0°C for 1 hour to precipitate a precipitate. The precipitate was collected by filtration, and the obtained precipitate was recrystallized twice using a mixed solvent of toluene and heptane (volume ratio: 3:10). Then, by drying under reduced pressure at 50° C., metal complex MC10 (15.8 g, yield 30%) was obtained as a yellow solid. The HPLC area percentage value of metal complex MC10 was 99.5% or more.

The LC-MS and NMR measurement results of the metal complex MC10 were as follows.
LC-MS (APCI, positive): m/z=1815.0 [M+H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 8.03 (s, 6H), 7.35 (s, 6H), 7.31-7.26 (m, 6H), 7 .11-7.03 (m, 6H), 6.98-6.90 (m, 6H) 6.62-6.57 (m, 3H), 6.52 (d, 3H), 2.11 ( s, 18H), 1.97 (s, 9H), 1.68 (s, 9H), 1
. 46 (s, 27H), 1.33 (s, 27H).

<Synthesis and acquisition of compounds B1 to B9>
The compound B1 used was manufactured by Luminescence Technology.
Compound B2 was synthesized by the method described below.
Compounds B3 and B4 were synthesized according to the method described in WO2015/102118.
Compounds B5 to B8 were synthesized by the following method.
Compound B9 is described in Angew. Chem. Int. Ed. 2020, 59, 17442-17446.

The _ΔEST of compound B1 was 0.49 eV. The maximum peak wavelength of the emission spectrum of compound B1 at room temperature was 452 nm. The maximum peak half width of the emission spectrum of compound B1 at room temperature was 22 nm.
The _ΔEST of compound B2 was 0.43 eV. The maximum peak wavelength of the emission spectrum of compound B2 at room temperature was 465 nm. The maximum peak half width of the emission spectrum of compound B2 at room temperature was 21 nm.
The _ΔEST of compound B3 was 0.46 eV. The maximum peak wavelength of the emission spectrum of compound B3 at room temperature was 454 nm. The maximum peak half width of the emission spectrum of compound B3 at room temperature was 21 nm.
The _ΔEST of compound B4 was 0.47 eV. The maximum peak wavelength of the emission spectrum of compound B4 at room temperature was 440 nm. The maximum peak half width of the emission spectrum of compound B4 at room temperature was 19 nm.
The _ΔEST of compound B5 was 0.45 eV. The maximum peak wavelength of the emission spectrum of compound B5 at room temperature was 465 nm. The maximum peak half width of the emission spectrum of compound B5 at room temperature was 18 nm.
The _ΔEST of compound B6 was 0.46 eV. The maximum peak wavelength of the emission spectrum of compound B6 at room temperature was 469 nm. The maximum peak half width of the emission spectrum of compound B6 at room temperature was 19 nm.
The _ΔEST of compound B7 was 0.38 eV. The maximum peak wavelength of the emission spectrum of compound B7 at room temperature was 471 nm. The maximum peak half width of the emission spectrum of compound B7 at room temperature was 20 nm.
The _ΔEST of compound B8 was 0.41 eV. The maximum peak wavelength of the emission spectrum of compound B8 at room temperature was 477 nm. The maximum peak half width of the emission spectrum of compound B8 at room temperature was 21 nm.
The _ΔEST of compound B9 was 0.32 eV. The maximum peak wavelength of the emission spectrum of compound B9 at room temperature was 514 nm. The half width of the maximum peak of the emission spectrum of compound B9 at room temperature was 38 nm.

<Synthesis of Compound B2>
Compound B2 was synthesized by the following method.

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound B2A (22.5 g) synthesized by the method described in Angewandte Chemie, International Edition, 2018, Vol. 57, pp. 11316-11320 ) and chlorobenzene were added and stirred, boron triiodide (16.4 g) was added, and the mixture was heated and stirred at 90° C. for 6 hours. Then, it was cooled to room temperature, N,N-diisopropylethylamine (14.3 mL) was added dropwise, and stirring was continued at room temperature for 15 minutes. A 10% by mass sodium sulfite aqueous solution (70 mL) was added to the resulting solution. The above operation was repeated twice, and the obtained organic layers were mixed and washed with a 10 mass % sodium sulfite aqueous solution and ion exchange. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate, and then filtered through a filter loaded with 45 g of florisil. After concentrating the obtained filtrate, acetonitrile (340 mL) was added thereto, stirred for 1 hour, and the obtained solid was filtered. The resulting solid was dissolved in toluene (790 mL). Carborafin (33 g) was added to the resulting solution, and the mixture was stirred for 1 hour and then filtered through a filter covered with celite, which was repeated three times. The resulting solution was concentrated under reduced pressure, and the resulting solid was recrystallized multiple times using a mixed solvent of toluene and acetonitrile and a mixed solvent of toluene and ethanol, and dried under reduced pressure at 50°C to obtain compound B2 (30.9 g , yellow solid).

The measurement results of LC-MS and NMR of compound B2 were as follows.
LC-MS (APCI, positive): m/z = 922 [M+H] ^+
1 H-NMR (CDCl ₃ , 400 MHz) δ (ppm) = 9.05 (d, 1H), 9.00 (d, 1H), 8.32 (d, 1H), 8.15 (d, 1H) , 7.52 (td, 2H), 7.43 (d, 1H) 7.38 (d, 1H), 7.32-7.22 (m, 6H), 7.20 (td, 2H)7. 13 (td, 4H), 6.65 (d, 1H), 6.16 (d, 1H), 1.62 (s, 9H), 1.48 (s, 9H), 1.43 (s, 9H) ), 1.36(s, 18H), 1.34(s, 9H).

<Synthesis of compound B5>
Compound B5 was synthesized by the following method.

After making the inside of the reaction vessel an argon atmosphere, 4-bromo-4′-tert-butylbiphenyl (30 g), 4-chloro-2,6-dimethylaniline (17.76 g), Pd ₂ (dba) ₃ (dba) _0.92 (0.88 g), t-Bu ₃ PHBF ₄ (0.95 g), t-BuONa (14.95 g) and toluene (900 mL) were added and stirred at 50° C. for 4 hours. Then, it was cooled to room temperature, and the reaction solution was filtered through a short column laminated with silica gel and celite. A crude product was obtained by concentrating the filtrate under reduced pressure. This crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene) and concentrated under reduced pressure. After that, it was recrystallized with a mixed solution of toluene and isopropyl alcohol and then dried to obtain compound B5A (25.2 g, white solid). The HPLC area percentage value for compound B5A was 99%.

The NMR measurement results of compound B5A were as follows.
¹ H-NMR (CD ₂ Cl ₂ -d ₂ , 400 MHz): δ (ppm) = 7.44-7.36 (m, 6H), 7.11 (s, 2H), 6.52 (td, 2H ), 5.26 (br, 1H), 2.18 (s, 6H), 1.31 (s, 9H)

After making the inside of the reaction vessel an argon atmosphere, compound B5A (24.30 g), 1,3-dibromo-5-tert-butylbenzene (9.7 g), Pd ₂ (dba) ₃ (dba) _0.92 (0 .56 g), t-Bu ₃ PHBF ₄ (0.60 g), t-BuONa (7.98 g) and toluene (291 mL) were added and stirred at 50° C. for 4 hours. Then, it was cooled to room temperature, and the reaction solution was filtered through a short column laminated with silica gel and celite. A crude product was obtained by concentrating the filtrate under reduced pressure. The crude product was purified by silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure, and dried to obtain compound B5B (18.1 g, white solid). The HPLC area percentage value for compound B5B was 99%.

The NMR measurement results of compound B5B were as follows.
¹ H-NMR (CD ₂ Cl ₂ -d ₂ , 400 MHz): δ (ppm) = 7.47-7.45 (m, 4H), 7.41-7.38 (m, 8H), 7.09 (s, 4H), 6.92 (td, 4H), 6.52 (d, 2H), 6.48 (t, 1H), 1.97 (s, 12H), 1.32 (s, 18H) , 1.10(s, 9H).

After making the inside of the reaction vessel an argon atmosphere, compound B5B (18.1 g) and chloroform (363 mL) were added, and after cooling to 0° C., N-bromosuccinimide (3.93 g) was added in portions and stirred. bottom. After that, the extract was washed with an aqueous sodium sulfite solution and then concentrated under reduced pressure. After that, toluene (180 mL) was added, filtered through a short column laminated with silica gel/Celite, and concentrated under reduced pressure. Thereafter, the compound B5C (17.5 g, white solid) was obtained by recrystallizing with a mixed solution of toluene and ethanol and then drying. The HPLC area percentage value for compound B5C was 99%.

The NMR measurement results of Compound B5C were as follows.
¹ H-NMR (CD ₂ Cl ₂ -d ₂ , 400 MHz): δ (ppm) = 7.49-7.33 (m, 14H), 7.06 (s, 2H), 6.99 (s, 2H ), 6.88 (s, 1H), 6.84 (d, 2H), 6.65 (br, 2H), 6.32 (s, 1H), 1.89 (s, 12H), 1.42 (s, 9H), 1.31 (s, 18H).

After making the inside of the reaction vessel an argon atmosphere, compound B5C and xylene (429.5 mL) were added, and after cooling to -40°C, a sec-BuLi/cyclohexane solution (1.0 M, 18.3 mL) was slowly added thereto. added. The reaction was stirred at -10°C for 1 hour. The reaction was then cooled to −60° C., BBr ₃ (3.57 mL) was added and stirred for 1 hour. After that, the temperature was gradually raised to 90° C. to cause the reaction. After that, the reaction solution was cooled to room temperature, N,N-diisopropylamine (31.4 mL) and toluene (258 mL) were added, and the organic layer was washed with an aqueous sodium sulfite solution and deionized water. The obtained organic layer was concentrated under reduced pressure to obtain a yellow solid. The resulting solid was purified by silica gel column chromatography (mobile phase solvent: mixed solvent of hexane and toluene), concentrated under reduced pressure, and dried. After that, it was recrystallized with a mixed solution of toluene and ethanol and then dried to obtain compound B5D (6.6 g, yellow solid). The HPLC area percentage value for compound B5D was 99%.

The NMR measurement results of compound B5D were as follows.
¹ H-NMR (CD ₂ Cl ₂ -d ₂ , 400 MHz): δ (ppm) = 9.36 (d, 2H), 7.75-7.71 (m, 6H), 7.51 (d, 4H ), 7.39 (s, 4H), 6.74 (d, 2H), 6.18 (s, 2H), 1.91 (s, 12H), 1.37 (s, 18H), 1.04 (s, 9H).

After the inside of the reaction vessel was replaced with an argon atmosphere, compound B5D (10 g), bis(pinacolato)diboron (5.72 g), potassium acetate (6.5 g), Pd ₂ (dba) ₃ (dba) _0.92 (0.92 g) were added. 21 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.38 g) and cyclopentyl methyl ether (130 mL) were added and heated with stirring for 45 hours. After that, toluene (130 ml) was added, the mixture was filtered through a filter lined with celite, the obtained filtrate was concentrated under reduced pressure, acetonitrile was added, and the obtained solid was collected by filtration. Then, toluene and activated carbon are added, and the mixture is stirred at room temperature for 30 minutes, filtered through a filter lined with celite, the resulting filtrate is concentrated under reduced pressure, and further recrystallized with a mixed solvent of toluene and acetonitrile to give the compound. B5E (5.8 g) was obtained as a yellow solid. The HPLC area percentage value of compound B5E showed more than 99.5%.

The NMR measurement results of compound B5E were as follows.
¹ H-NMR (CD ₂ Cl ₂ -d ₂ , 400 MHz): δ (ppm) = 9.37 (d, 2H), 7.77 (s, 4H), 7.73 (d, 4H), 7. 68 (dd, 2H), 7.51 (d, 4H), 6.68 (d, 2H), 6.19 (s, 2H), 1.93 (s, 12H), 1.38-1.37 (m, 42H), 1.00 (s, 9H).

After making the inside of the reaction vessel an argon atmosphere, compound B5E (2.3 g), 2-bromo-4,6-di(4-tert-butylphenyl)benzene (1.9 g), Pd ₂ (dba) ₃ (dba) ) _0.92 (0.02 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.04 g), toluene (115 ml), and 40 mass % tetrabutylammonium hydroxide aqueous solution (7.1 g) , ion-exchanged water (28 mL) was added, and the mixture was heated and stirred for 1 hour. After cooling the resulting reaction solution to room temperature, ion-exchanged water (40 mL) was added, and the aqueous layer was removed. The resulting organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered, and the resulting filtrate was concentrated under reduced pressure. Toluene and activated carbon were added, the mixture was stirred at room temperature for 30 minutes, filtered through a filter covered with celite, and the resulting filtrate was concentrated under reduced pressure. Compound B5 (3.0 g) was obtained as a yellow solid by recrystallization with a mixed solvent of toluene and acetonitrile. The HPLC area percentage value of compound B5 showed 99.0% or more.

The measurement results of LC-MS and NMR of compound B5 were as follows.
LC-MS (APCI positive): m/z=1476.9 [M+H] ^+
1 H-NMR (CD ₂ Cl ₂ -d ₂ , 400 MHz): δ (ppm) = 9.46 (d, 2H), 7.98 (d, 4H), 7.88 (t, 2H), 7. 74-7.82 (m, 18H), 7.54-7.59 (m, 12H), 6.94 (d, 2H), 6.35 (s, 2H), 2.07 (t, 12H) , 1.34-1.45 (m, 54H), 1.04-1.08 (m, 9H)

<Synthesis of Compound B6>
Compound B6 was synthesized by the following method.

After making the inside of the reaction vessel an argon atmosphere, N-(3-chloro-4-methylphenyl)-2,6-dimethyl-benzenamine (20.0 g), 1,3-dibromo-5-tert-butylbenzene ( 11.7 g), tris(dibenzylideneacetone) dipalladium (1.1 g), tri-tert-butylphosphonium tetrafluoroborate (0.72 g), sodium tert-butoxide (9.6 g), and toluene (500 mL) was added and stirred at 50° C. for 4 hours. After that, water (400 mL) was added and stirred at room temperature. The reaction liquid was liquid-separated and washed with ion-exchanged water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, toluene was added to the obtained oily substance to dissolve it, followed by filtration through a filter covered with silica gel, and the obtained filtrate was concentrated under reduced pressure. Thereafter, recrystallization was performed twice using a mixed solvent of toluene, ethyl acetate, and acetonitrile, and dried under reduced pressure at 40°C to obtain compound B6A (19.2 g, white solid) with a yield of 77%. The LC area percentage value of compound B6A was 98.6%.

The NMR measurement results of compound B6A were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 7.11-7.03 (m, 6H), 6.97 (d, 2H), 6.88 (d, 2H), 6.67 ( dd, 2H), 6.51 (t, 1H), 6.42 (d, 2H), 2.34 (s, 6H), 1.92 (s, 12H), 1.07 (s, 9H).

After the inside of the reaction vessel was replaced with an argon atmosphere, compound B6A (5.5 g), boron triiodide (6.9 g) and 1,2-dichlorobenzene (66 mL) were added and stirred at 120° C. for 75 hours. After that, N,N-diisopropylethylamine (6.8 mL) and 10% by mass sodium sulfite aqueous solution (23 mL) were added and stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, recrystallized once using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 40° C. to give compound B6B (2.0 g, yellow solid) with a yield of 40%. Obtained. The LC area percentage value of compound B6B was 96.9%. The required amount of compound B6B was obtained by repeating the above steps.

The NMR measurement results of compound B6B were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 8.74 (s, 2H), 7.41-7.29 (md, 6H), 6.68 (s, 2H), 6.05 ( s, 2H), 2.56 (s, 6H), 1.90 (s, 12H), 0.98 (s, 9H).

After making the inside of the reaction vessel an argon atmosphere, compound B6B (8.0 g), 3,6-di-tert-butylcarbazole (7.1 g), tris(dibenzylideneacetone) dipalladium (0.45 g), 2- Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.66 g), a toluene solution of lithium (bistrimethylsilyl)amide (1 mol/L, 28 mL), and xylene (76 mL) and stirred at 130° C. for 6 hours. Then, it was separated and washed with ion-exchanged water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and heptane. Thereafter, recrystallization was performed multiple times using a mixed solvent of toluene and acetonitrile, and drying was performed under reduced pressure at 40°C to obtain compound B6 (4.0 g, yellow solid) with a yield of 28%. The LC area percentage value of compound B6 was 97.0%.

The NMR measurement results of compound B6 were as follows.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 9.09 (s, 2H), 8.13 (d, 4H), 7.42 (dd, 4H), 7.24 (d, 6H) , 7.00 (d, 4H), 6.82 (s, 2H), 6.12 (s, 2H), 2.11 (s, 6H), 1.99 (s, 12H), 1.47 ( s, 36H), 1.00 (s, 9H).
LC-MS (APCI, positive): m/z=1115.7 [M+H] ⁺

<Synthesis of compound B7>
Compound B7 was synthesized by the following method.

After making the inside of the reaction vessel an argon atmosphere, N-(3-chlorophenyl)-2,6-dimethyl-benzenamine (10.0 g), 1,3-dibromo-5-tert-butylbenzene (5.8 g), Tris(dibenzylideneacetone) dipalladium (0.35 g), tri-tert-butylphosphonium tetrafluoroborate (0.34 g), sodium tert-butoxide (5.7 g), and toluene (250 mL) were added and C. for 5 hours. After that, water (100 mL) was added and stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and heptane (volume ratio 1:9). Thereafter, recrystallization was performed once using a mixed solvent of toluene, ethyl acetate and methanol, and drying was performed under reduced pressure at 40° C. to obtain compound B7A (8.3 g, white solid) with a yield of 71%. The LC area percentage value for compound B7A was 97.8%.

The NMR measurement results of compound B7A were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.14-7.02 (8H, m), 6.79 (2H, t), 6.73 (4H, td), 6. 53 (1H, t), 6.50 (2H, d), 1.95 (12H, s), 1.05 (9H, s).
TLC-MS (positive): m/z = 593.2 [M+H] ⁺

After the inside of the reaction vessel was replaced with an argon atmosphere, compound B7A (2.0 g), boron triiodide (2.6 g) and 1,2-dichlorobenzene (40 mL) were added and stirred at 120° C. for 90 hours. After that, N,N-diisopropylethylamine (8.9 g) and 10 mass % sodium sulfite aqueous solution (20 mL) were added and stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. The obtained filtrate was concentrated under reduced pressure, recrystallized once using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 40° C. to give compound B7B (0.76 g, yellow solid) with a yield of 30%. Obtained. The LC area percentage value of compound B7B was 97.6%.

The NMR measurement results of compound B7B were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 8.81 (2H, d), 7.43-7.32 (6H, m), 7.20 (2H, dd), 6. 65 (2H,d), 6.12 (2H,s), 1.88 (12H,s), 0.95 (9H,s).
TLC-MS (positive): m/z = 601.2 [M+H] ⁺

After making the inside of the reaction vessel an argon atmosphere, compound B7B (0.10 g), 4-(1,1-dimethylethyl)-N-[4-(1,1-dimethylethyl)phenyl]-N-[4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-benzenamine (0.18 g), [(di(1-adamantyl)-N-butylphosphine)- 2-(2′-Amino-1,1′-biphenyl)]palladium (II) methanesulfonate (4.8 mg), 5% by mass sodium carbonate aqueous solution (13 mL), and toluene (10 mL) were added, and 80 C. for 5 hours. Then, it was separated and washed with ion-exchanged water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and heptane. Thereafter, recrystallization was performed once using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 40° C. to obtain compound B7 (0.19 g, yellow solid) with a yield of 83%. The LC area percentage value of compound B7 was 99.9%.

The NMR measurement results of compound B7 were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 9.01 (2H, d), 7.48 (2H, d), 7.42-7.30 (10H, m), 7. 28 (8H, d), 7.03-6.95 (12H, m), 6.85 (2H, d), 6.12 (2H, s), 1.
92 (12H,s), 1.29 (36H,s), 0.98 (9H,s).
TLC-MS (positive): m/z=1243.5 [M+H] ⁺

<Synthesis of compound B8>
Compound B8 was synthesized by the following method.

After making the inside of the reaction vessel an argon atmosphere, 2-bromo-5-tert-butyl-1,3-dimethylbenzene (5.0 g), 3-chloroaniline (3.2 g), tris(dibenzylideneacetone) dipalladium (0.10 g), tri-tert-butylphosphonium tetrafluoroborate (0.10 g), sodium tert-butoxide (4.0 g) and toluene (90 mL) were added and stirred at 50° C. for 5 hours. After that, water (10 mL) was added and the mixture was stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and heptane (volume ratio 2:8). Then, it was recrystallized once using methanol and dried under reduced pressure at 40° C. to obtain compound B8A (3.8 g, white solid) with a yield of 64%. The GC area percentage value of compound B8A was 99.7%.

The NMR measurement results of compound B8A were as follows.
₁ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.12-7.07 (3H, m), 7.04 (1H, t), 6.69 (1H, t), 6.69 (1H, t); 82 (1H, d), 6.77 (1H, d), 6.44 (1H, d), 6.17 (1H, d), 6.10 (1H, t), 5.70 (1H, broad -s), 5.19 (1H, broad-s), 2.19 (6H, s), 1.29 (9H, s).
TLC-MS (positive): m/z = 288.1 [M+H] ⁺

After making the inside of the reaction vessel an argon atmosphere, compound B8A (3.7 g), 1,3-dibromo-5-tert-butylbenzene (1.9 g), tris(dibenzylideneacetone) dipalladium (0.11 g), Tri-tert-butylphosphonium tetrafluoroborate (0.11 g), sodium tert-butoxide (1.8 g) and toluene (44 mL) were added and stirred at 50° C. for 5 hours. After that, water (20 mL) was added and stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and heptane (volume ratio 1:9). Thereafter, recrystallization was performed once using a mixed solvent of toluene, ethyl acetate, and acetonitrile, and dried under reduced pressure at 40°C to obtain compound B8B (2.5 g, white solid) with a yield of 55%. The LC area percentage value for compound B8B was 97.7%.

The NMR measurement results of compound B8B were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.06 (4H, s), 7.02 (2H, t), 6.78 (2H, t), 6.73-6. 68 (4H,m), 6.58 (2H,d), 6.36 (1H,t), 1.92 (12H,s), 1.30 (18H,s), 1.08 (9H,s) ).
TLC-MS (positive): m/z=705.3 [M+H] ⁺

After the inside of the reaction vessel was replaced with an argon atmosphere, compound B8B (2.0 g), boron triiodide (2.2 g) and 1,2-dichlorobenzene (40 mL) were added and stirred at 120° C. for 90 hours. After that, N,N-diisopropylethylamine (7.5 g) and 10 mass % sodium sulfite aqueous solution (20 mL) were added and stirred at room temperature. It was separated and washed with deionized water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure, recrystallized once using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 40° C. to give compound B8C (1.1 g, yellow solid) with a yield of 50%. Obtained. The LC area percentage value of compound B8C was 92.0%.

The NMR measurement results of compound B8C were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 8.80 (2H, d), 7.36 (4H, s), 7.19 (2H, dd), 6.72 (2H, d), 6.07 (2H,s), 1.85 (12H,s), 1.41 (18H,s), 0.94 (9H,s).
TLC-MS (positive): m/z=713.3 [M+H] ⁺

After making the inside of the reaction vessel an argon atmosphere, compound B8C (0.30 g), 2-[4,4′-bis(1,1-dimethylethyl)[1,1′:3′,1′-terphenyl] -5′-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.43 g), [(di(1-adamantyl)-N-butylphosphine)-2-(2 '-Amino-1,1'-biphenyl)]palladium (II) methanesulfonate (12 mg), 5 wt% sodium carbonate aqueous solution (15 mL), and toluene (15 mL) were added and stirred at 80°C for 5 hours. . Then, it was separated and washed with ion-exchanged water. The obtained washing liquid was separated, and the obtained organic layer was dried with magnesium sulfate and then filtered. After the obtained filtrate was concentrated under reduced pressure, silica gel column purification was performed using a mixed solvent of toluene and heptane. After that, recrystallization was performed once using a mixed solvent of toluene and acetonitrile, and dried under reduced pressure at 40° C. to obtain compound B8 (0.34 g, yellow solid) with a yield of 61%. The LC area percentage value of compound B8 was 99.7%.

The NMR measurement results of compound B8 were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 9.11 (2H, d),
7.75 (2H, t), 7.70 (4H, d), 7.66 (2H, dd), 7.57 (8H, d), 7.48 (8H, d), 7.40 (4H , s), 7.06 (2H, d), 6.26 (2H, s), 1.94 (12H, s), 1.41 (18H, s), 1.36 (36H, s), 1 .12(9H,s).
TLC-MS (positive): m/z=1324.6 [M+H] ⁺

<Synthesis of Compounds M1 to M12, B10 and B11, and Metal Complex MC12>
Compound M1 was synthesized according to the method described in WO2015/145871.
Compound M2 was synthesized according to the method described in WO2013/146806.
Compound M3 was synthesized according to the method described in WO2005/049546.
Compound M4 was synthesized according to the method described in JP-A-2010-180630.
Compound M5 was synthesized according to the method described in International Publication No. 2013/191088.
Compound M6 was synthesized according to the method described in WO2015/145871.
Compound M7 was synthesized according to the method described in JP-A-2011-174062.
Commercially available products were used for compound M8 and compound M9.
Compound M10 was synthesized according to the method described in WO2012/086671.
Compound M11 was synthesized according to the method described in WO2016/031639.
Compound M12 was synthesized according to the method described in JP-A-2012-036388.
Compounds B10 and B11 were synthesized according to the method described in WO2019/004248.
Metal complex MC12 was synthesized according to the method described in JP-A-2015-038195.

<Synthesis of polymer compound HTL-1>
Polymer compound HTL-1 was synthesized using compound M1, compound M2 and compound M3 according to the method described in WO 2015/145871. The Mn of the polymer compound HTL-1 was 2.3×10 ⁴ and the Mw was 1.2×10 ⁵ .
In the polymer compound HTL-1, the theoretical values obtained from the amounts of the raw materials charged are the structural units derived from the compound M1, the structural units derived from the compound M2, and the structural units derived from the compound M3. It is a copolymer composed of a molar ratio of 45:5:50.

<Synthesis of polymer compound BP1>
(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound M4 (0.3444 g), compound M5 (0.5762 g), compound B10 (0.0851 g), dichlorobis(tris-o-methoxyphenylphosphine) Palladium (0.27 mg) and toluene (30 mL) were added and heated to 80°C.
(Step 2) Thereafter, a 20% by mass tetraethylammonium hydroxide aqueous solution (16.0 g) was added dropwise thereto, and refluxed for 6 hours.
(Step 3) After that, phenylboronic acid (45.7 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.27 mg) were added thereto and stirred at 80° C. for 3 hours.
(Step 4) After cooling the reaction mixture, an aqueous sodium diethyldithiacarbamate solution was added, and the mixture was stirred at 40°C for 1 hour. After cooling the reaction solution and removing the aqueous layer, the resulting organic layer was washed twice with 3 mass % aqueous ammonia and twice with water. The resulting solution was added dropwise to methanol and stirred to cause precipitation. The precipitate was dissolved in toluene (44 mL), alumina (26 g) was added, and the mixture was stirred for 3 hours, and the resulting suspension was passed through a silica gel column for purification. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The resulting precipitate was collected by filtration and dried to obtain 0.51 g of polymer compound BP1. Mn of the polymer compound BP1 was 6.2×10 ⁴ and Mw was 1.5×10 ⁵ .
In the polymer compound BP1, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M4, the structural unit derived from the compound M5, and the structural unit derived from the compound B10 are 50: It is a copolymer made up of a 45:5 molar ratio.

<Synthesis of polymer compound BP2>
(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound M4 (0.3070 g), compound M5 (0.6403 g), compound B11 (0.0927 g), dichlorobis(tris-o-methoxyphenylphosphine) Palladium (0.27 mg) and toluene (31 mL) were added and heated to 80°C.
(Step 2) Thereafter, a 20% by mass tetraethylammonium hydroxide aqueous solution (15.7 g) was added dropwise thereto, and refluxed for 6 hours.
(Step 3) After that, phenylboronic acid (45.7 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.27 mg) were added thereto and stirred at 80° C. for 3 hours.
(Step 4) After cooling the reaction mixture, an aqueous sodium diethyldithiacarbamate solution was added, and the mixture was stirred at 40°C for 1 hour. After cooling the reaction solution and removing the aqueous layer, the resulting organic layer was washed twice with 3 mass % aqueous ammonia and twice with water. The resulting solution was added dropwise to methanol and stirred to cause precipitation. After the precipitate was dissolved in toluene (44 mL), alumina (27 g) was added, and the mixture was stirred for 3 hours, the resulting suspension was passed through a silica gel column for purification. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The precipitate was collected by filtration and dried to obtain 0.52 g of polymer compound BP2.
The polymer compound BP2 had Mn of 6.3×10 ⁴ and Mw of 1.5×10 ⁵ .
In the polymer compound BP2, the theoretical value obtained from the amount of the charged raw material is 45: It is a copolymer made up of a 50:5 molar ratio.

(Synthesis of polymer compound BP3)
Polymer compound BP3 was synthesized using compound M9, compound M11, compound M10 and compound B10 according to the method described in WO2019/004248. The polymer compound BP3 had an Mn of 4.5×10 ⁴ and an Mw of 1.1×10 ⁵ .
According to the theoretical values obtained from the amount of the starting material, the polymer compound BP3 has a structural unit derived from the compound M9, a structural unit derived from the compound M11, a structural unit derived from the compound M9, and a structural unit derived from the compound B10. The derived structural units are copolymers made up in a molar ratio of 45:5:49:1.

(Synthesis of polymer compound MP1)
Polymer compound MP1 was synthesized using compound M4, compound M5, compound M6, and metal complex MC12 according to the method described in JP-A-2015-038195. The Mn of the polymer compound MP1 was 9.0×10 ⁴ and the Mw was 2.3×10 ⁵ .
According to the theoretical values obtained from the amount of the charged raw material, the polymer compound MP1 has a structural unit derived from the compound M4, a structural unit derived from the compound M5, a structural unit derived from the compound M6, and a metal complex MC12. is a copolymer composed of structural units derived from and in a molar ratio of 50:15:20.5:14.5.

<Synthesis Example ET2> Synthesis of Polymer Compound ET2 (Synthesis of Polymer Compound ET2a)
Polymer compound ET2a is compound ET2-1 synthesized according to the method described in JP-A-2012-33845, and compound ET2-2 synthesized according to the method described in JP-A-2012-33845. It was synthesized according to the method described in JP-A-2012-33845.

Mn of the polymer compound ET2a was 5.2×10 ⁴ .

The polymer compound ET2a is composed of structural units derived from the compound ET2-1 and structural units derived from the compound ET2-2 at a molar ratio of 50:50, according to the theoretical values obtained from the amounts of the raw materials. It is a copolymer that has been

(Synthesis of polymer compound ET2)
After making the inside of reaction container into inert gas atmosphere, high molecular compound ET2a (200 mg), tetrahydrofuran (20 mL), and ethanol (20 mL) were added, and it heated at 55 degreeC. After that, cesium hydroxide (200 mg) dissolved in water (2 mL) was added thereto, and the mixture was stirred at 55°C for 6 hours. Then, after cooling to room temperature, a solid was obtained by concentrating under reduced pressure. The resulting solid was washed with water and dried under reduced pressure to obtain polymer compound ET2 (150 mg, pale yellow solid). From the NMR spectrum of the polymer compound ET2 obtained, it was confirmed that the signal derived from the ethyl group in the ethyl ester moiety of the polymer compound ET2a completely disappeared.

<Synthesis of polymer compound HP1>
Polymer compound HP1 was synthesized using compound M7 and compound M8 according to the method described in International Publication No. 2012/086670.
The polymer compound HP1 had an Mn of 1.3×10 ⁵ and an Mw of 3.6×10 ⁵ .
According to the theoretical value obtained from the amount of the raw material charged, the polymer compound HP1 is a copolymer composed of structural units derived from the compound M7 and structural units derived from the compound M8 at a molar ratio of 50:50. It is a coalescence.

<Synthesis of polymer compound HP2>
Polymer compound HP2 was synthesized using compound M4, compound M10 and compound M12 according to the method described in JP-A-2012-36388.
The polymer compound HP2 had an Mn of 9.6×10 ⁴ and an Mw of 2.2×10 ⁵ .
In the polymer compound HP2, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M4, the structural unit derived from the compound M10, and the structural unit derived from the compound M12 are 50: It is a copolymer made up of a 40:10 molar ratio.

<Synthesis of polymer compound HP3>
Polymer compound HP3 was synthesized using compound M4, compound M5 and compound M6 according to the method described in WO 2015/008851.
The Mn of the polymer compound HP3 was 8.5×10 ⁴ and the Mw was 2.2×10 ⁵ .
In the polymer compound HP3, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M4, the structural unit derived from the compound M5, and the structural unit derived from the compound M6 are 50: It is a copolymer made up of a 26:24 molar ratio.

<Example D1> Production and evaluation of light emitting device D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed into a film with a thickness of 35 nm by a spin coating method to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and further heated at 230° C. for 15 minutes to form a hole injection layer.

(Formation of hole transport layer)
A polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the xylene solution thus obtained, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method. A pore transport layer was formed. By this heating, the polymer compound HTL-1 was in a crosslinked state.

(Formation of light-emitting layer)
Compound H1, metal complex MC1 and compound B1 (compound H1/metal complex MC1/compound B1=73 mass %/25 mass %/2 mass %) were dissolved in toluene at a concentration of 1.8 mass %. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

(Formation of cathode)
After reducing the pressure of the substrate on which the light-emitting layer is formed to 1.0×10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride of about 4 nm is deposited on the light-emitting layer as a cathode, and then on the sodium fluoride layer. About 80 nm of aluminum was evaporated. After vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate to produce a light-emitting device D1.

(Evaluation of Light Emitting Element)
EL light emission was observed by applying a voltage to the light emitting element D1. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D1 at 10 mA/cm ² were measured.

<Example D2> Preparation and evaluation of light-emitting element D2 In the same manner as in Example D1 except that "metal complex MC2" was used instead of "metal complex MC1" in (formation of light-emitting layer) of Example D1. , a light-emitting device D2 was produced.
EL light emission was observed by applying a voltage to the light emitting element D2. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D2 at 10 mA/cm ² were measured.

<Comparative Example CD1> Production and evaluation of light-emitting element CD1 A light-emitting element CD1 was produced in the same manner as in Example D1, except that (formation of light-emitting layer) of Example D1 was changed to (formation of light-emitting layer CD1).

(Formation of light-emitting layer CD1)
Compound H1, metal complex MC3 and compound B1 (compound H1/metal complex MC3/compound B1=73 mass %/25 mass %/2 mass %) were dissolved in chlorobenzene at a concentration of 1.8 mass %. Using the obtained chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by spin coating, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .
EL light emission was observed by applying a voltage to the light emitting element CD1. The driving voltage [V] and CIE chromaticity coordinates of the light emitting element CD1 at 10 mA/cm ² were measured.

Table 4 shows the results of Examples D1 to D2 and Comparative Example CD1. In Table 4, the driving voltage difference [V] indicates the difference between the driving voltage [V] of the light emitting element CD1 and the driving voltage [V] of the light emitting elements D1 and D2.

<Example D3> Production and evaluation of light emitting device D3 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed into a film with a thickness of 35 nm by a spin coating method to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and further heated at 230° C. for 15 minutes to form a hole injection layer.

(Formation of hole transport layer)
A polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the xylene solution thus obtained, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method. A pore transport layer was formed. By this heating, the polymer compound HTL-1 was in a crosslinked state.

(Formation of light-emitting layer)
Compound H1, metal complex MC1 and compound B1 (compound H1/metal complex MC1/compound B1=73% by mass/25% by mass/2% by mass) were dissolved in chlorobenzene at a concentration of 1.8% by mass. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

(Formation of electron transport layer)
Compound ET1 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.4% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 20 nm was formed on the light-emitting layer by spin coating. An electron transport layer was formed by heating at 130° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After reducing the pressure of the substrate on which the electron transport layer was formed to 1.0 × 10 ^-4 Pa or less in a vapor deposition machine, as a cathode, sodium fluoride was deposited on the light emitting layer to about 4 nm, and then on the sodium fluoride layer. About 80 nm of aluminum was vapor-deposited on the substrate. After vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate to produce a light-emitting element D3.

(Evaluation of Light Emitting Element)
EL light emission was observed by applying a voltage to the light emitting element D3. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D3 at 50 mA/cm ² were measured.

<Example D4> Production and evaluation of light-emitting element D4 In the same manner as in Example D3, except that "metal complex MC2" was used instead of "metal complex MC1" in (formation of light-emitting layer) of Example D3. , a light-emitting device D4 was produced.
EL light emission was observed by applying a voltage to the light emitting element D4. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D4 at 50 mA/cm ² were measured.

<Comparative Example CD2> Preparation and Evaluation of Light-Emitting Element CD2 In the same manner as in Example D3, except that "Metal Complex MC3" was used instead of "Metal Complex MC1" in (Formation of Light-Emitting Layer) of Example D3. , a light-emitting device CD2 was fabricated.
EL light emission was observed by applying a voltage to the light emitting element CD2. The driving voltage [V] and CIE chromaticity coordinates of the light emitting device CD2 at 50 mA/cm ² were measured.

Table 5 shows the results of Examples D3 to D4 and Comparative Example CD2. In Table 5, the driving voltage difference [V] indicates the difference between the driving voltage [V] of the light emitting element CD2 and the driving voltage [V] of the light emitting elements D3 and D4.

<Examples D5 to D21 and Comparative Example CD3> Production and Evaluation of Light-Emitting Elements D5 to D21 and Light-Emitting Element CD3 Instead of "Compound H1, Metal Complex MC1 and Compound B1" in (Formation of Light-Emitting Layer) of Example D3 , Light-emitting elements D5 to D21 and light-emitting element CD3 were fabricated in the same manner as in Example D3, except that the materials shown in Table 6 were used.
EL light emission was observed by applying a voltage to the light emitting elements D5 to D21 and the light emitting element CD3. Driving voltage [V] and CIE chromaticity coordinates at 1 mA/cm ² of the light emitting elements D5 to D21 and the light emitting element CD3 were measured.

Table 6 shows the results of Examples D5 to D21 and Comparative Example CD3. In Table 6, the driving voltage difference [V] indicates the difference between the driving voltage [V] of the light emitting element CD3 and the driving voltage [V] of the light emitting elements D5 to D21.

<Examples D22 to D27> Production and evaluation of light-emitting elements D22 to D27 Instead of “compound H1, metal complex MC1 and compound B1” in (formation of light-emitting layer) of Example D3, the materials shown in Table 7 were used. Light-emitting devices D22 to D27 were produced in the same manner as in Example D3, except that
EL light emission was observed by applying a voltage to the light emitting elements D22 to D27. The driving voltage [V] and CIE chromaticity coordinates of the light emitting elements D22 to D27 at 10 mA/cm ² were measured.

Table 7 shows the results of Examples D22 to D27. In Table 7, the driving voltage difference [V] indicates the difference between the driving voltage [V] of the light emitting element D27 and the driving voltage [V] of the light emitting elements D22 to D26.

<Examples D28 to D33 and Comparative Example CD4> Production and evaluation of light emitting elements D28 to D33 and light emitting element CD4 Light emission was performed in the same manner as in Example D3 except that the materials and composition ratios (% by mass) shown in Table 8 were used instead of "metal complex MC1/compound B1 = 73% by mass/25% by mass/2% by mass)". Devices D28 to D33 and light-emitting device CD4 were produced.
EL light emission was observed by applying a voltage to the light emitting elements D28 to D33 and the light emitting element CD4. The driving voltage [V] and CIE chromaticity coordinates of the light emitting elements D28 to D33 at 5 mA/cm ² were measured.

Table 8 shows the results of Examples D28 to D33 and Comparative Example CD4. In Table 8, the drive voltage difference [V] indicates the difference between the drive voltage [V] of the light emitting elements D28 to D33 with respect to the drive voltage [V] of the light emitting element CD4.

<Example D34> Preparation and evaluation of light emitting device D34 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed into a film with a thickness of 35 nm by a spin coating method to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and further heated at 230° C. for 15 minutes to form a hole injection layer.

(Formation of hole transport layer)
A polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the xylene solution thus obtained, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method. A pore transport layer was formed. By this heating, the polymer compound HTL-1 was in a crosslinked state.

(Formation of light-emitting layer)
Compound H1, metal complex MC1 and compound B1 (compound H1/metal complex MC1/compound B1=73 mass %/25 mass %/2 mass %) were dissolved in toluene at a concentration of 1.8 mass %. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

(Formation of electron transport layer)
A polymer compound ET2 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.4% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 20 nm was formed on the light-emitting layer by spin coating. An electron transport layer was formed by heating at 130° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After reducing the pressure of the substrate on which the electron transport layer was formed to 1.0 × 10 ^-4 Pa or less in a vapor deposition machine, as a cathode, sodium fluoride was deposited on the light emitting layer to about 4 nm, and then on the sodium fluoride layer. About 80 nm of aluminum was vapor-deposited on the substrate. After vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate to produce a light-emitting device D34.

(Evaluation of Light Emitting Element)
EL light emission was observed by applying a voltage to the light emitting element D34. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D34 at 10 mA/cm ² were measured.

<Examples D35 to D41> Production and evaluation of light emitting elements D35 to D41 In (formation of light emitting layer) of Example D34, “Compound H1, metal complex MC1 and compound B1 (compound H1/metal complex MC1/compound B1 = 73 Light-emitting elements D35 to D41 were produced in the same manner as in Example D34, except that the materials and composition ratios (% by mass) shown in Table 9 were used instead of "% by mass/25% by mass/2% by mass."
EL light emission was observed by applying a voltage to the light emitting elements D35 to D41. Driving voltage [V] and CIE chromaticity coordinates of the light-emitting elements D35 to D41 at 10 mA/cm ² were measured.

<Comparative Example CD5> Preparation and evaluation of light-emitting element CD5 Light-emitting element CD5 was produced in the same manner as in Example D34, except that (formation of light-emitting layer) of Example D34 was changed to the following (formation of light-emitting layer CD-5). was made.
EL light emission was observed by applying a voltage to the light emitting element CD5. The driving voltage [V] and CIE chromaticity coordinates of the light emitting element CD5 at 10 mA/cm ² were measured.

(Formation of light-emitting layer CD-5)
Polymer compound MP1 and polymer compound BP2 (polymer compound MP1/polymer compound BP2=25% by mass/75% by mass) were dissolved in toluene at a concentration of 1.0% by mass. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

Table 9 shows the results of Examples D34 to D41 and Comparative Example CD5. In Table 10, the driving voltage difference [V] indicates the difference between the driving voltage [V] of the light emitting element CD5 and the driving voltage [V] of the light emitting elements D34 to D41.

<Example D42> Production and evaluation of light emitting device D42 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed into a film with a thickness of 35 nm by a spin coating method to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and further heated at 230° C. for 15 minutes to form a hole injection layer.

(Formation of hole transport layer)
A polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the xylene solution thus obtained, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method. A pore transport layer was formed. By this heating, the polymer compound HTL-1 was in a crosslinked state.

(Formation of light-emitting layer)
Compound H1, metal complex MC4 and compound B1 (compound H1/metal complex MC4/compound B1=73% by mass/25% by mass/2% by mass) were dissolved in toluene at a concentration of 1.8% by mass. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

(Formation of electron transport layer)
A polymer compound ET2 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.4% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 20 nm was formed on the light-emitting layer by spin coating. An electron transport layer was formed by heating at 130° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After reducing the pressure of the substrate on which the electron transport layer was formed to 1.0 × 10 ^-4 Pa or less in a vapor deposition machine, as a cathode, sodium fluoride was deposited on the light emitting layer to about 4 nm, and then on the sodium fluoride layer. About 80 nm of aluminum was vapor-deposited on the substrate. After vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate to produce a light-emitting device D42.

(Evaluation of Light Emitting Element)
EL light emission was observed by applying a voltage to the light emitting element D42. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D42 at 1 mA/cm ² were measured.

<Examples D43 to D44> Preparation and evaluation of light emitting elements D43 to D44 In (formation of light emitting layer) of Example D42, “Compound H1, metal complex MC4 and compound B1 (compound H1/metal complex MC4/compound B1 = 73 Light-emitting elements D43 to D44 were produced in the same manner as in Example D42, except that the materials and composition ratios (% by mass) shown in Table 10 were used instead of "% by mass/25% by mass/2% by mass."
EL light emission was observed by applying a voltage to the light emitting elements D43 and D44. Driving voltage [V] and CIE chromaticity coordinates of the light-emitting elements D43 to D44 at 1 mA/cm ² were measured.

<Example D45> Preparation and evaluation of light-emitting element D45 Light-emitting element D45 was produced in the same manner as in Example D42, except that (formation of light-emitting layer) of Example D42 was changed to the following (formation of light-emitting layer D-45). was made.
EL light emission was observed by applying a voltage to the light emitting element D45. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D45 at 1 mA/cm ² were measured.

(Formation of light-emitting layer D-45)
Polymer compound HP1, metal complex MC4, and compound B1 (polymer compound HP1/metal complex MC4/compound B1=73% by mass/25% by mass/2% by mass) were dissolved in toluene at a concentration of 1.2% by mass. rice field. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

<Example D46> Production and evaluation of light-emitting element D46 Light-emitting element D46 was prepared in the same manner as in Example D42, except that (formation of light-emitting layer) of Example D42 was changed to the following (formation of light-emitting layer D-46). was made.
EL light emission was observed by applying a voltage to the light emitting element D46. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D46 at 1 mA/cm ² were measured.

(Formation of light-emitting layer D-46)
Polymer compound HP2, metal complex MC4, and compound B1 (polymer compound HP2/metal complex MC4/compound B1=73% by mass/25% by mass/2% by mass) were dissolved in toluene at a concentration of 1.0% by mass. rice field. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

<Example D47> Preparation and evaluation of light-emitting element D47 Light-emitting element D47 was prepared in the same manner as in Example D42, except that (formation of light-emitting layer) of Example D42 was changed to the following (formation of light-emitting layer D-47). was made.
EL light emission was observed by applying a voltage to the light emitting element D47. The driving voltage [V] and CIE chromaticity coordinates of the light-emitting element D47 at 1 mA/cm ² were measured.

(Formation of light-emitting layer D-47)
Polymer compound HP3, metal complex MC4 and compound B1 (polymer compound HP3/metal complex MC4/compound B1=73% by mass/25% by mass/2% by mass) were dissolved in toluene at a concentration of 1.2% by mass. rice field. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

<Comparative Example CD6> Preparation and evaluation of light-emitting element CD6 Light-emitting element CD6 was prepared in the same manner as in Example D42, except that (formation of light-emitting layer) of Example D42 was changed to the following (formation of light-emitting layer CD-6). was made.
EL light emission was observed by applying a voltage to the light emitting element CD6. The driving voltage [V] and CIE chromaticity coordinates of the light emitting device CD6 at 1 mA/cm ² were measured.

(Formation of light-emitting layer CD-6)
Polymer compound HP4, metal complex MC4, and compound B1 (polymer compound HP4/metal complex MC4/compound B1=73% by mass/25% by mass/2% by mass) were dissolved in chlorobenzene at a concentration of 1.6% by mass. rice field. Using the obtained chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by spin coating, and the film was heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. .

Table 10 shows the results of Examples D42 to D47 and Comparative Example CD6. In Table 10, the driving voltage difference [V] indicates the difference between the driving voltage [V] of the light emitting element CD6 and the driving voltage [V] of the light emitting elements D42 to D47.

As is clear from Tables 4 to 6, the light-emitting devices of Examples containing the composition containing the compound (A) having an aromatic heterocyclic ring containing a 5-membered ring were compositions containing no compound (A). It can be seen that the driving voltage is lower than that of the light emitting element of the comparative example.

As is clear from Tables 8 to 10, the light-emitting elements of Examples containing the composition containing the first compound are driven more than the light-emitting elements of Comparative Examples containing compositions not containing the first compound. It can be seen that the voltage is low.

Claims (13)

selected from the group consisting of a metal complex represented by formula (1) and a polymer compound (A) containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (1) and at least one
A low-molecular-weight compound (B) having a condensed heterocyclic skeleton (b) containing a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom, a selenium atom, an ^sp3 carbon atom and a nitrogen atom in the ring and at least one selected from the group consisting of a polymer compound (B) containing a structural unit having a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (B),
A compound represented by formula (H-1) and at least one structural unit selected from the group consisting of structural units represented by formula (X) and structural units represented by formula (Y) at least one selected from the group consisting of polymer compounds;
A composition comprising

[In the formula,
M represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
ⁿ¹ represents an integer of 1 or more, and ⁿ² represents an integer of 0 or more. However, n ¹ +n ² is 3 when M is a rhodium atom or an iridium atom, and n ¹ +n ² is 2 when M is a palladium atom or a platinum atom.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. When multiple E ¹ and E ² are present, they may be the same or different.
Ring L ¹ represents an aromatic heterocyclic ring containing a 5-membered ring, and the ring may have a substituent. 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 atoms to which they are bonded. When multiple rings L ¹ are present, they may be the same or different.
Ring ^L2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. 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 atoms to which they are bonded. When there is more than one ring ^L2 , they may be the same or different.
The substituent that ring L ¹ may have and the substituent that ring L ² may have may be the same or different, and are bonded to each other to form a ring together with the atoms to which they are bonded. may be formed.
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 forming a bidentate ligand together with A ¹ and A ² . When multiple A ¹ -G ¹ -A ² are present, they may be the same or different. ]

[In the formula,
Ar ^H1 and Ar ^H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent. 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 atoms to which they are bonded.
n ^H1 represents an integer of 0 or more.
L ^H1 represents a divalent group, and the divalent group may have a substituent. 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 atoms to which they are bonded. When multiple L ^H1 are present, they may be the same or different, and they may be directly bonded to each other or bonded via a divalent group to form a ring.
Ar ^H1 and Ar ^H2 may be directly bonded or bonded via a divalent group to form a ring. L ^H1 and Ar ^H1 may be directly bonded or bonded via a divalent group to form a ring. L ^H1 and Ar ^H2 may be directly bonded or bonded via a divalent group to form a ring. ]

[In the formula,
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^{1 X1} and Ar 2 ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.
Ar ^X2 and Ar ^X4 each independently represent 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; and these groups may have a substituent. 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 atoms to which they are bonded. When multiple Ar ^X2 are present, they may be the same or different. When multiple Ar ^X4 are present, they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded. When multiple R ^X2 are present, they may be the same or different. When multiple R ^X3 are present, they may be the same or different. ]

[Wherein, Ar ^Y 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, The group may have a substituent. 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 atoms to which they are bonded. ] The ring L ² is an aromatic hydrocarbon ring containing a 5- or 6-membered ring, or an aromatic heterocyclic ring containing a 5- or 6-membered ring, and these rings have a substituent The composition of claim 1, which may be The ring L ² is a monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring, or a monocyclic, bicyclic or tricyclic aromatic heterocyclic ring, and these rings are substituted The composition according to claim 1, which optionally has a group. 4. The ring ^L2 according to claim 3, wherein the ring L2 is a benzene ring, a fluorene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these rings may have a substituent. Composition. The composition according to any one of claims 1 to 4, wherein said ring L ¹ is a diazole ring or triazole ring, and these rings may have a substituent. 6. The composition according to claim 5, wherein the ring ^L1 is an optionally substituted triazole ring. Any one of claims 1 to 4, wherein the condensed heterocyclic skeleton (b) contains a boron atom and at least one selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom in the ring. 13. The composition of claim 1. 8. The composition of claim 7, wherein the fused heterocyclic skeleton (b) contains boron and nitrogen atoms in the ring. Claim 1, wherein the low-molecular-weight compound (B) is a compound represented by formula (1-1), a compound represented by formula (1-2), or a compound represented by formula (1-3). A composition according to any one of claims 1 to 4.

[In the formula,
Ar ¹ , Ar ² and Ar ³ each independently represent an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.
Y ¹ represents an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, an alkylene group or a cycloalkylene group, and these groups may have a substituent. 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 atoms to which they are bonded.
Y ² and Y ³ each independently represent a single bond, an oxygen atom, a sulfur atom, a selenium atom, a group represented by -N(Ry)-, a group represented by -B(Ry)-, an alkylene group, It represents a cycloalkylene group, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded.
Ry represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. 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 atoms to which they are bonded. When two or more Ry are present, they may be the same or different.
Y ¹ and Ar ¹ may be directly bonded or bonded via a divalent group to form a ring. Y ¹ and Ar ² may be directly bonded or bonded via a divalent group to form a ring. Y ² and Ar ¹ may be directly bonded or bonded via a divalent group to form a ring. Y ² and Ar ³ may be directly bonded or bonded via a divalent group to form a ring. Y ³ and Ar ² may be directly bonded or bonded via a divalent group to form a ring. Y ³ and Ar ³ may be directly bonded or bonded via a divalent group to form a ring. ] 10. The composition according to claim 9, wherein said Y ¹ , said Y ² and said Y ³ are an oxygen atom, a sulfur atom or a group represented by -N(Ry)-. The composition according to claim 10, wherein said Y ¹ , said Y ² and said Y ³ are groups represented by -N(Ry)-. Any one of claims 1 to 4, further comprising at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent. A composition according to claim 1. A light-emitting element having an anode, a cathode, and an organic layer provided between the anode and the cathode,
A light-emitting device, wherein the organic layer is a layer containing the composition according to any one of claims 1 to 4.