WO2022181075A1

WO2022181075A1 - Polymer compound and light-emitting element using same

Info

Publication number: WO2022181075A1
Application number: PCT/JP2022/000483
Authority: WO
Inventors: 元章臼井; 智裕道堯; 敦資麻野; 慎也田中
Original assignee: 住友化学株式会社
Priority date: 2021-02-25
Filing date: 2022-01-11
Publication date: 2022-09-01
Also published as: JP2022130289A; TW202239806A

Abstract

Provided is a polymer compound that can be used to produce a light-emitting element that has an excellent luminance lifetime.　A polymer compound that includes a first structural unit that is represented by formula (0) and a second structural unit that is not the first structural unit. (In the formula, a and b each independently represent an integer from 0 to 3, R1 and R2 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, any of which may have a substituent, and R0 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, any of which may have a substituent, at least one R0 being a group represented by formula (D-C).)

Description

Polymer compound and light-emitting device using the same

The present invention relates to a polymer compound and a light emitting device using the same.

A light-emitting element such as an organic electroluminescence element can be suitably used for display and lighting applications. As a material for use in a light-emitting device, for example, Patent Document 1 describes a polymer compound containing a structural unit represented by the following formula.

JP 2011-174061 A

However, the light-emitting device manufactured using the polymer compound described above does not necessarily have a sufficient luminance lifetime.
SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to provide a polymer compound useful for manufacturing a light-emitting device having excellent luminance lifetime.

The present invention provides the following [1] to [15].
[1]
a first structural unit represented by formula (0);
a second structural unit that is a structural unit other than the first structural unit;
Polymer compounds, including

[In the formula,
a and b each independently represents an integer of 0 to 3;
R ¹ and R ² each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom; The group may have a substituent. When multiple R ¹ and R ² are present, they may be the same or different.
R ⁰ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups are substituents may have A plurality of R ⁰ may be the same or different.
However, at least one of R ⁰ represents a group represented by formula (D—C). ]

[In the formula,
^mDA1 represents an integer of 2 or more and 10 or less.
Ar ^DA1 represents an optionally substituted arylene group. A plurality of Ar ^DA1 may be the same or different.
^TDA represents an aryl group optionally having a substituent. ]
[2]
The polymer compound according to [1], wherein the first structural unit is a structural unit represented by formula (0-1).

[wherein, a, b, R ¹ , R ² and R ⁰ have the same meanings as defined above. ]
[3]
The polymer compound according to [1] or [2], wherein the Ar ^DA1 is a phenylene group optionally having a substituent.
[4]
The polymer compound according to any one of [1] to [3], wherein the ^TDA is a phenyl group which may have a substituent.
[5]
The polymer compound according to any one of [1] to [4], wherein the first structural unit is a structural unit represented by formula (1).

[In the formula,
a, b, ^R1 and ^R2 have the same meanings as above.
n represents 1 or 2;
c and d each independently represent an integer of 0 to 4; e represents an integer of 0 to 5; When there are multiple c, d and e, they may be the same or different.
^RA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups are substituents may have
R ³ , R ⁴ and R ⁵ each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom; , these groups may have a substituent. When multiple R ³ , R ⁴ and R ⁵ are present, they may be the same or different. ]
[6]
The polymer compound according to [5], wherein n is 2.
[7]
The polymer compound according to any one of [1] to [6], wherein the first structural unit is a structural unit represented by formula (5).

[In the formula, e and R ⁵ have the same meanings as described above. ]
[8]
The polymer compound according to any one of [1] to [7], wherein the second structural unit comprises a structural unit represented by formula (Y).

[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. However, the structural unit represented by the formula (Y) is different from the structural unit represented by the formula (0). ]
[9]
The structural unit represented by the formula (Y) is a structural unit represented by the formula (Y-1), a structural unit represented by the formula (Y-2), and a structure represented by the formula (Y-3). unit, a structural unit represented by formula (Y-4), a structural unit represented by formula (Y-5), a structural unit represented by formula (Y-6), a structural unit represented by formula (Y-7) at least selected from the group consisting of a structural unit represented by the formula (Y-8), a structural unit represented by the formula (Y-9) and a structural unit represented by the formula (Y-10) The polymer compound according to [8], containing one type of structural unit.

[In the formula, R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent . A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[In the formula,
^RY1 has the same meaning as above.
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 -. ^RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY2 may be the same or different, and the ^RY2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[In the formula, ^{RY1 and XY1} ^have the same meanings as described above. ]

[In the formula,
^RY1 has the same meaning as above.
^RY3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[In the formula,
^RY1 has the same meaning as above.
^RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]
[10]
The polymer compound according to any one of [1] to [9], wherein the second structural unit comprises a structural unit represented by formula (X).

[In the formula,
a ¹ and a ² 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.
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 multiple Ar ^X2 and 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 multiple R ^X2 and R ^X3 are present, they may be the same or different. ]
[11]
The polymer compound according to any one of [1] to [10], wherein the second structural unit includes a structural unit having a crosslinkable group.
[12]
The polymer compound according to [11], wherein the cross-linking group is a cross-linking group selected from X group of cross-linking groups.
(Crosslinking group X 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 ]
[13]
The polymer compound according to [12], wherein the structural unit having the crosslinkable group is a structural unit represented by formula (2) or a structural unit represented by formula (2').

[In the formula,
nA represents an integer of 0 to 5, n represents 1 or 2;
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and these groups have a substituent; good too. R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^A are present, they may be the same or different.
X represents a cross-linking group selected from X group of cross-linking groups. When there are multiple X's, they may be the same or different. ]

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. When multiple mA are present, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent may be
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
each of Ar ⁴ , Ar ⁵ and Ar ⁶ is bonded directly or through an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring; may be
K ^A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and these groups have a substituent; good too. R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple K ^A are present, they may be the same or different.
X' represents a bridging group selected from the bridging group X group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. However, at least one X' is a cross-linking group selected from the X group of cross-linking groups. ]
[14]
selected from the group consisting of the polymer compound according to any one of [1] to [13], 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 and at least one.
[15]
At least one selected from the group consisting of the polymer compound according to any one of [1] to [13] and the crosslinked product of the polymer compound according to any one of [11] to [13]. light-emitting element.

According to the present invention, it is possible to provide a polymer compound useful for manufacturing a light-emitting device with excellent luminance life. Moreover, according to the present invention, a composition and a light-emitting device containing the polymer compound can be provided.

A preferred embodiment of the present invention will be 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 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 contained 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, because if the polymerization active group remains as it is, the light-emitting properties may deteriorate when the polymer compound is used for the production of a light-emitting device. The terminal group of the polymer compound is preferably a group conjugated to the main chain, for example, an aryl group or a monovalent heterocyclic group that binds to the main chain of the polymer compound via a carbon-carbon bond. is mentioned.

The "alkyl group" may be either linear or branched. The number of carbon atoms in the linear alkyl group is generally 1-50, preferably 1-30, more preferably 1-20, not including the number of carbon atoms in the substituents. The number of carbon atoms in the branched alkyl group is generally 3-50, preferably 3-30, more preferably 4-20, 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. octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl and dodecyl groups. In addition, alkyl groups are groups in which some or all of the hydrogen atoms in these groups are substituted with substituents (e.g., cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc.) (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, 6-ethyloxyhexyl group).

The number of carbon atoms in the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, more preferably 4 to 20, not including the number of carbon atoms in 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.

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, not including the carbon atoms of the substituents. The number of carbon atoms in the branched alkenyl group is usually 3-30, preferably 4-20, not including the number of carbon atoms in the substituents.
The alkenyl group may have a substituent. Examples of alkenyl groups include vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, 7-octenyl groups 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 "cycloalkenyl group" is usually 3-30, preferably 4-20, not including the number of carbon atoms in the substituents.
A cycloalkenyl group may have a substituent. Cycloalkenyl groups include, for example, 5-cyclohexenyl groups and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.

An "alkynyl group" may be either linear or branched. The straight-chain alkynyl group usually has 2 to 20 carbon atoms, preferably 3 to 20 carbon atoms, not including substituent carbon atoms. The number of carbon atoms in the branched alkynyl group is usually 4-30, preferably 4-20, not including the carbon atoms of the substituents.
The alkynyl 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.

The number of carbon atoms in the "cycloalkynyl group" is usually 4-30, preferably 4-20, not including the carbon atoms of the substituents.
A cycloalkynyl group may have a substituent. Cycloalkynyl groups include, for example, 5-cyclohexynyl groups and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents.

An "alkoxy group" may be either linear or branched. The straight-chain alkoxy group usually has 1 to 40 carbon atoms, preferably 4 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 4-10, not including the number of carbon atoms in the substituents.
The alkoxy group may have a substituent. Alkoxy groups include, for example, methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, tert-butyloxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2 -Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and some or all of the hydrogen atoms in these groups are substituted groups (e.g., cycloalkyl groups, alkoxy groups, cycloalkoxy group, aryl group, fluorine atom, etc.).

The number of carbon atoms in the "cycloalkoxy group" is usually 3-40, 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 usually 6-60, preferably 6-48, not including the number of carbon atoms in the substituents.
The aryloxy group may have a substituent. Examples of aryloxy groups include phenoxy, 1-naphthyloxy, 2-naphthyloxy, 1-anthracenyloxy, 9-anthracenyloxy, 1-pyrenyloxy groups, and these groups. Examples thereof include groups in which some or all of hydrogen atoms are substituted with substituents (eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, fluorine atoms, etc.).

“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, benzofluorene, pyrene and tetracyclic aromatic hydrocarbons such as fluoranthene; pentacyclic aromatic hydrocarbons such as dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, perylene and benzofluoranthene; hexacyclic aromatic hydrocarbons such as spirobifluorene aromatic hydrocarbons of the formula; and heptacyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene), one hydrogen atom directly bonded to a carbon atom constituting the ring Groups other than the above may be mentioned. Aromatic hydrocarbon groups include groups in which a plurality of these groups are bonded. The aromatic hydrocarbon group may have a substituent.

Aryl groups include, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and some or all of the hydrogen atoms in these groups are substituents ( Examples thereof include groups substituted with alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, fluorine atoms, etc.).

Examples of arylene groups include phenylene, naphthalenediyl, anthracenediyl, phenanthenediyl, dihydrophenanthenediyl, naphthacenediyl, fluorenediyl, pyrenediyl, perylenediyl, chrysenediyl groups, and Groups in which some or all of the hydrogen atoms are substituted with substituents are included. The arylene group includes groups in which multiple of these groups are bonded. Arylene groups are preferably groups represented by formulas (A-1) to (A-20).

[In the formula, R and Ra each independently represent ^a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. Plural R and R ^a may be the same or different, and R ^a may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

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 "aromatic heterocyclic compounds" include oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole Compounds in which the heterocycle itself exhibits aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilole, benzopyran, etc., even if the heterocycle itself does not exhibit aromaticity, the heterocyclic ring is condensed with an aromatic ring. compounds that are
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. Heterocyclic groups include groups in which multiple of these groups are bonded. A heterocyclic group may have a substituent (eg, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).

The monovalent heterocyclic group includes, for example, thienyl, pyrrolyl, furyl, pyridyl, piperidinyl, quinolinyl, isoquinolinyl, pyrimidinyl, triazinyl, and part of the hydrogen atoms in these groups, or Examples include groups that are entirely substituted with substituents (eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups) and the like.

The number of carbon atoms in the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, more preferably 4 to 15, not including the number of carbon atoms in the substituents.
Examples of divalent heterocyclic groups include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, A divalent group obtained by removing two hydrogen atoms among hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting a ring from diazole or triazole. Divalent heterocyclic groups include groups in which multiple of these groups are bonded. The divalent heterocyclic group is preferably a group represented by formulas (AA-1) to (AA-34).

[In the formula, R and ^Ra represent the same meanings as described above. ]

"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 for the amino group are alkyl groups, cycloalkyl groups, aryl groups and monovalent heterocyclic groups, and these groups may 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, a dialkylamino group, a dicycloalkylamino group, a diarylamino group, and those in which some or all of the hydrogen atoms are substituted (e.g., an alkyl group, a cycloalkyl group, an alkoxy group , a cycloalkoxy group, an aryl group, a fluorine atom, etc.).
Examples of substituted amino groups include dimethylamino group, diethylamino group, diphenylamino group, bis(methylphenyl)amino group, bis(3,5-di-tert-butylphenyl)amino group, and hydrogen in these groups. Examples thereof include groups in which some or all of the atoms are substituted with substituents (eg, alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc.).

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 a cross-linking group selected from Group X of cross-linking groups (that is, cross-linking groups represented by formulas (XL-1) to (XL-19)).
(Crosslinking group X 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, cycloalkynyl groups and the like can be mentioned. A substituent may be a bridging group.

<Polymer compound>
The polymer compound of the present embodiment includes a first structural unit represented by formula (0) and a second structural unit other than the first structural unit.

In the polymer compound of the present embodiment, the second structural unit is selected from the group consisting of a structural unit represented by formula (Y), a structural unit represented by formula (X), and a structural unit having a cross-linking group. It preferably contains at least one selected structural unit.

<First structural unit>
[Structural Unit Represented by Formula (0)]
R ⁰ is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group or a cycloalkyl group, since the light-emitting device of the present embodiment has a superior luminance lifetime. or an aryl group, more preferably an aryl group, and these groups may have a substituent.

The substituent that R ⁰ 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 group or a halogen atom. , an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, an alkyl group, a cycloalkyl group or an aryl group is more preferable, and these groups further have a substituent. good too.

a is preferably 0 or 1, more preferably 0, because the light-emitting element of this embodiment has a superior luminance lifetime.

b is preferably 0 or 1, more preferably 0, since the light-emitting element of this embodiment has a superior luminance lifetime.

R ¹ and R ² are preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or a cycloalkyl group, since the light-emitting device of the present embodiment has a superior luminance lifetime. The group may have a substituent.

Examples and preferred ranges of substituents that R ¹ and R ² may have are the same as examples and preferred ranges of substituents that R ⁰ may have.

m ^DA1 is preferably 2 to 5, more preferably 2 to 4, even more preferably 2 to 3, and 2, since the light emitting element of the present embodiment has a more excellent luminance life. is particularly preferred.

The aryl group in ^TDA is preferably a phenyl group, a naphthyl group, anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, a spirobifluorenyl group or a pyrenyl group, and 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.

The substituent that ^TDA 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 group or a halogen atom. , an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, an alkyl group, a cycloalkyl group or an aryl group is more preferable, an alkyl group or a cycloalkyl group is particularly preferable, and these The group may further have a substituent.

Substituents that ^TDA may further have include alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, aryloxy groups, and monovalent heterocyclic rings. A group, a substituted amino group or a halogen atom is preferable, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, an alkyl group or a cycloalkyl group is more preferable, and these groups are further It may have a substituent, but preferably has no substituent.

The arylene group for Ar ^DA1 is preferably a phenylene group, a naphthalenediyl group, anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthacenediyl group, a fluorenediyl group or a pyrenediyl group, and a phenylene group, a naphthalenediyl group or a An orangeyl group is more preferable, and a phenylene group is more preferable, and these groups may have a substituent.

Examples and preferred ranges of substituents that Ar ^DA1 may have are the same as examples and preferred ranges of substituents that T ^DA may have.

Examples and preferred ranges of the substituents that the substituents that Ar ^DA1 may further have are the substituents that the substituents that T ^DA may further have Same as examples and preferred ranges.

The structural unit represented by formula (0) is preferably a structural unit represented by formula (0-1).

The structural unit represented by formula (0) is more preferably a structural unit represented by formula (1).

[Structural Unit Represented by Formula (1)]
n is more preferably 2 because the light-emitting element of this embodiment has a superior luminance lifetime.

c and d are preferably 0 to 2, more preferably 0 or 1, and still more preferably 0, because the light-emitting element of the present embodiment has a superior luminance lifetime.

e is preferably 0 to 3, more preferably 0 to 2, and even more preferably 0 or 1, since the light-emitting element of the present embodiment has a superior luminance life.

^RA is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group or a cycloalkyl group, since the light-emitting device of the present embodiment has a superior luminance lifetime. or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

The substituent that ^RA 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 group or a halogen atom. , an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, an alkyl group, a cycloalkyl group or an aryl group is more preferable, an aryl group is particularly preferable, and these groups are further substituted You may have a group.

Among the substituents that ^RA may have, the aryl group includes a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, a spirobifluorenyl group, or a pyrenyl group. is preferred, a phenyl group, a naphthyl group or a fluorenyl group is more preferred, a phenyl group or a fluorenyl group is even more preferred, and a fluorenyl group is particularly preferred, and these groups may have a substituent.

Examples and preferred ranges of the substituents which the substituents which R ^A may further have are the substituents which the substituents which T ^DA may further have Same as examples and preferred ranges.

R ³ and R ⁴ are preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or a cycloalkyl group, since the light-emitting device of the present embodiment has a superior luminance lifetime. The group may have a substituent.

Examples and preferred ranges of substituents that R ³ and R ⁴ may have are the same as examples and preferred ranges of substituents that Ar ^DA1 may have.

R ⁵ is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, since the light-emitting device of the present embodiment has a superior luminance lifetime, and these groups are substituted You may have a group.

Examples and preferred ranges of substituents that R ⁵ may have are the same as examples and preferred ranges of substituents that ^TDA may have.

The structural unit represented by formula (1) is preferably a structural unit represented by formula (1-1), more preferably a structural unit represented by formula (1-2).

As the structural unit represented by formula (0), a structural unit represented by formula (5) is more preferable.

In the polymer compound of the present embodiment, the content of the first structural unit is preferably It is 0.5 to 90 mol %, more preferably 5 to 80 mol %, still more preferably 10 to 70 mol %.

Specific examples of the structural unit represented by formula (0) include structural units represented by formulas (0-101) to (0-137).

Only one type of the first structural unit may be contained in the polymer compound, or two or more types may be contained.

<Second structural unit>
Examples of the second structural unit include a structural unit represented by formula (Y), a structural unit represented by formula (X), and a structural unit having a cross-linking group.

[Structural Unit Represented by Formula (Y)]
The arylene group represented by Ar ^Y1 is more preferably represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula ( A-13) or a group represented by formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9) or formula (A-19) These groups may have a substituent.

The divalent heterocyclic group represented by Ar ^Y1 is more preferably formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) ) or a group represented by formula (AA-20), more preferably represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) groups, and these groups may have a substituent.

A more preferred range of the arylene group and the divalent heterocyclic group in the divalent group represented by Ar ^Y1 in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, more preferably The range is the same as the more preferred range and the more preferred range of the arylene group and divalent heterocyclic group represented by Ar ^Y1 described above, respectively.

As the divalent group in which at least one ^arylene group represented by ^Ar ^Y1 and at least one divalent heterocyclic group are directly bonded, at least Examples thereof include the same divalent groups in which one arylene group and at least one divalent heterocyclic group are directly bonded.

The substituent that the group represented by Ar ^Y1 may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may further have a substituent.

Examples of structural units represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-10). Is preferably a structural unit represented by formulas (Y-1) to (Y-3), and from the viewpoint of electron transport properties, preferably represented by formulas (Y-4) to (Y-7) From the viewpoint of hole transport properties, structural units represented by formulas (Y-8) to (Y-10) are preferred.

(Constituent unit represented by formula (Y-1))

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

The structural unit represented by formula (Y-1) is preferably a structural unit represented by formula (Y-1').

[In the formula, R ^Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY11 may be the same or different. ]

R ^Y11 is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

(Constituent unit represented by formula (Y-2))

R ^Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. may

In X ^Y1 , the combination of two R ^Y2 in the group represented by —C(R ^Y2 ) ₂ — is preferably both an alkyl group or a cycloalkyl group, both an aryl group, and both a monovalent a cyclic group, or one of which is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group and the other is an aryl group; may have a substituent. Two R ^Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y2 forms a ring, the group represented by -C(R ^Y2 ) ₂ - is preferably a group represented by formulas (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), these groups having a substituent You may have

In X ^Y1 , the combination of two R ^Y2 in the group represented by -C(R ^Y2 )=C(R ^Y2 )- is preferably both alkyl groups or cycloalkyl groups, or one of them is an alkyl group Alternatively, it is a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

In X ^Y1 , four R ^Y2 in the group represented by -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ - are preferably optionally substituted alkyl groups or cycloalkyl groups is. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y2 forms a ring, -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ - The group represented is preferably a group represented by formulas (Y-B1) to (Y-B5), more preferably a group represented by formula (Y-B3), and these groups are It may have a substituent.

[In the formula, ^RY2 has the same meaning as described above. ]

The structural unit represented by formula (Y-2) is preferably a structural unit represented by formula (Y-2').

[In the formula, ^{RY1 and XY1} ^have the same meanings as described above. ]

(Constituent unit represented by formula (Y-3))

[In the formula, ^{RY1 and XY1} ^have the same meanings as described above. ]

The structural unit represented by formula (Y-3) is preferably a structural unit represented by formula (Y-3').

[In the formula, ^RY11 and ^XY1 have the same meanings as described above. ]

(Constituent units represented by formulas (Y-4) to (Y-7))

R ^Y3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. may

The structural unit represented by formula (Y-4) is preferably a structural unit represented by formula (Y-4′), and the structural unit represented by formula (Y-6) is represented by formula (Y -6') is preferred.

[In the formula, R ^Y1 and R ^Y3 have the same meanings as described above. ]

(Constituent units represented by formulas (Y-8) to (Y-10))

[In the formula,
^RY1 has the same meaning as above.
^RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

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

Examples of structural units represented by formula (Y) include structural units composed of arylene groups represented by formulas (Y-101) to (Y-141), formulas (Y-201) to (Y- 209), at least one arylene group and at least one divalent heterocyclic ring represented by formulas (Y-301) to (Y-306) A structural unit composed of a divalent group directly bonded to a group is exemplified.

The content of the structural unit represented by the formula (Y) in which Ar 2 ^Y1 is an arylene group is the structural unit contained in the polymer compound because the luminance life of the light-emitting device of the present embodiment is superior. is preferably 0.5 to 80 mol %, more preferably 30 to 60 mol %, based on the total amount of

Structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or a divalent in which at least one arylene group and at least one divalent heterocyclic group are directly bonded is preferably 0.5 to 40 mol% with respect to the total amount of the structural units contained in the polymer compound, because the light-emitting device of the present embodiment has excellent charge transport properties. Yes, more preferably 3 to 30 mol%.

The structural unit represented by the formula (Y) may be contained in one type or two or more types in the polymer compound.

[Structural Unit Represented by Formula (X)]
^aX1 is preferably 2 or less, and more preferably 1, because the light-emitting element of this embodiment has a superior luminance lifetime.

^aX2 is preferably 2 or less, and more preferably 0, since the light-emitting element of this embodiment has a superior luminance lifetime.

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, and these groups have a substituent; good too.

Arylene groups represented by Ar ^X1 and Ar ^X3 are more preferably groups represented by formula (A-1) or formula (A-9), more preferably represented by formula (A-1) groups, and these groups may have a substituent.

The divalent heterocyclic groups represented by Ar ^X1 and Ar ^X3 are more preferably represented by formula (AA-1), formula (AA-2) or formulas (AA-7) to (AA-26). These groups may have a substituent.

Ar 1 ^X1 and Ar ^{2 X3} are preferably optionally substituted arylene groups.

Arylene groups represented by Ar ^X2 and Ar ^X4 are more preferably represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11) or a group represented by formula (A-19), and these groups may have a substituent.

The more preferable range of the bivalent heterocyclic groups represented by Ar 1 ^X2 and Ar 2 ^X4 is the same as the more preferable range of the bivalent heterocyclic groups represented by Ar 1 ^X1 and Ar 2 ^X3 .

A more preferred range of the arylene group and the divalent heterocyclic group 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 more preferable range is the same as the more preferable range and the more preferable range of the arylene group and the divalent heterocyclic group represented by Ar 1 ^X1 and Ar 2 ^X3 , respectively.

Examples of 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 include groups represented by the following formulae. , these may have a substituent.

[In the formula, R ^XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

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

Ar ^X2 and Ar ^X4 are preferably arylene groups optionally having substituents.

The substituents that the groups represented by Ar ^X1 to Ar ^X4 and R ^X1 to R ^X3 may have are preferably alkyl groups, cycloalkyl groups or aryl groups, and these groups further have substituents. You may have

The structural unit represented by formula (X) is preferably a structural unit represented by formula (X-1) to formula (X-7), more preferably a structural unit represented by formula (X-3) to formula (X -7), more preferably structural units represented by formulas (X-3) to (X-6).

[Wherein, R ^X4 and R ^X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano represents a group, and these groups may have a substituent. Multiple R ^X4 may be the same or different. A plurality of R 1 ^X5 may be the same or different, and adjacent R 1 ^X5 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

Examples of the structural unit represented by formula (X) include structural units represented by formulas (X1-1) to (X1-23), preferably formulas (X1-6) to (X1 -14).

The content of the structural unit represented by the formula (X) is preferably 0.1 to 50 mol% with respect to the total amount of the structural units contained in the polymer compound, since the hole transport property is excellent. It is more preferably 1 to 40 mol %, still more preferably 5 to 30 mol %.

The polymer compound of the present embodiment may contain only one kind of structural unit represented by formula (X), or may contain two or more kinds thereof.

[Structural Unit Having a Crosslinking Group]
In the polymer compound of the present embodiment, the structural unit having a cross-linking group is preferably a structural unit having a cross-linking group selected from Group X of cross-linking groups. ') is more preferred.

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. When multiple mA are present, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent may be
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
each of Ar ⁴ , Ar ⁵ and Ar ⁶ is bonded directly or through an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring; may be
K ^A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and these groups have a substituent; good too. R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple K ^A are present, they may be the same or different.
X' represents a bridging group selected from the bridging group X group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. However, at least one X' is a cross-linking group selected from the X group of cross-linking groups. ]

As the cross-linking group selected from the cross-linking group X, since the polymer compound of the present embodiment has excellent cross-linking properties, formula (XL-1), formula (XL-3), formula (XL-5), formula (XL -7), a cross-linking group represented by formula (XL-16) or formula (XL-17) is preferred, and a cross-linking group represented by formula (XL-1) or formula (XL-17) is preferred.

(Structural Unit Represented by Formula (2))
nA is preferably 0 or 1, more preferably 0, since the light-emitting element of this embodiment has a superior luminance lifetime.

n is preferably 2 because the light-emitting element of this embodiment has a more excellent luminance lifetime.

Ar ³ is preferably an aromatic hydrocarbon group which may have a substituent, since the light-emitting device of this embodiment has a more excellent luminance lifetime.

The number of carbon atoms in the aromatic hydrocarbon group represented by Ar ³ is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18, not including the number of carbon atoms in the substituents. be.
The arylene group portion excluding the n substituents of the aromatic hydrocarbon group represented by Ar ³ is preferably a group represented by formulas (A-1) to (A-20), More preferably, a group represented by formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) and more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), The group may have a substituent.

The number of carbon atoms in the heterocyclic group represented by Ar ³ is usually 2 to 60, preferably 3 to 30, more preferably 4 to 18, not including the number of carbon atoms in substituents.
The divalent heterocyclic group moiety excluding n substituents of the heterocyclic group represented by Ar ³ is preferably a group represented by formulas (AA-1) to (AA-34). be.

The aromatic hydrocarbon group and heterocyclic group represented by Ar ³ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy groups, halogen atoms, monovalent heterocyclic groups and cyano groups.

The alkylene group represented by ^LA generally has 1 to 20 carbon atoms, preferably 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, not including the number of carbon atoms in the substituent. The cycloalkylene group represented by ^LA usually has 3 to 20 carbon atoms not including the number of carbon atoms in the substituent.
The alkylene group and cycloalkylene group may have a substituent, and examples thereof include methylene group, ethylene group, propylene group, butylene group, hexylene group, cyclohexylene group and octylene group.

The alkylene group and cycloalkylene group represented by ^LA may have a substituent. Examples of substituents which the alkylene group and the cycloalkylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom and a cyano group.

The arylene group represented by ^LA may have a substituent. Arylene groups include o-phenylene, m-phenylene and p-phenylene. Examples of substituents that the arylene group may have include alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, aryloxy groups, monovalent heterocyclic groups, halogen atoms, cyano groups and bridges. A bridging group selected from group X may be mentioned.

L ^A is preferably a phenylene group or an alkylene group because it facilitates production of the polymer compound of the present embodiment, and these groups may have a substituent.

As the cross-linking group represented by X, since the polymer compound of the present embodiment has excellent cross-linking properties, the cross-linking group of Formula (XL-1), Formula (XL-3), Formula (XL-5) or Formula (XL-5) is preferable. -7), a cross-linking group represented by formula (XL-16) or formula (XL-17), more preferably a cross-linking group represented by formula (XL-1) or formula (XL-17) .

Since the polymer compound of the present embodiment has excellent stability and crosslinkability, the content of the structural unit represented by formula (2) is preferably 0 with respect to the total amount of the structural units contained in the polymer compound. .5 to 50 mol %, more preferably 3 to 30 mol %, still more preferably 3 to 20 mol %.

The structural unit represented by the formula (2) may be contained in one type or two or more types in the polymer compound.

(Structural Unit Represented by Formula (2′))
mA is preferably 0 or 1, more preferably 0, since the light-emitting element of this embodiment has a superior luminance lifetime.

m is preferably 2 because the light-emitting element of this embodiment has a more excellent luminance lifetime.

c is preferably 0, since the production of the polymer compound of the present embodiment is facilitated and the luminance lifetime of the light emitting device of the present embodiment is more excellent.

Ar ⁵ is preferably an aromatic hydrocarbon group which may have a substituent, since the light-emitting device of this embodiment has a more excellent luminance lifetime.

Definitions and examples of the arylene group moiety excluding m substituents of the aromatic hydrocarbon group represented by Ar ⁵ are the same as definitions and examples of the arylene group represented by Ar ^X2 in formula (X). .

Definitions and examples of the divalent heterocyclic group moiety excluding m substituents of the heterocyclic group represented by Ar ⁵ are defined in the definition of the divalent heterocyclic group represented by Ar ^X2 in the formula (X). and examples are the same.

Definitions and examples of the divalent group excluding m substituents of the group represented by Ar ⁵ in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded are represented by the formula (X) is the same as the definition and examples of the divalent group in which at least one arylene group represented by Ar ^X2 and at least one divalent heterocyclic group are directly bonded.

Ar ⁴ and Ar ⁶ are preferably an arylene group optionally having a substituent, since the light-emitting device of this embodiment has a more excellent luminance lifetime.

The definitions and examples of the arylene groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the arylene groups represented by Ar ^X1 and Ar ^X3 in formula (X).

The definitions and examples of the bivalent heterocyclic groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the bivalent heterocyclic groups represented by Ar ^X1 and Ar ^X3 in formula (X).

The groups represented by Ar ⁴ , Ar ⁵ and Ar ⁶ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, Halogen atoms, monovalent heterocyclic groups and cyano groups are included.

Definitions and examples of the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by K ^A respectively refer to the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by ^LA . It is the same as the definition and examples of ring group.

^KA is preferably a phenylene group or a methylene group, since this facilitates the production of the polymer compound of the present embodiment.

As the cross-linking group represented by X′, since the polymer compound of the present embodiment has excellent cross-linking properties, the cross-linking group represented by the formula (XL-1), the formula (XL-3), the formula (XL-5), the formula ( XL-7), a cross-linking group represented by formula (XL-16) or formula (XL-17), more preferably a cross-linking group represented by formula (XL-1) or formula (XL-17) be.

The content of the structural unit represented by the formula (2′) is such that the polymer compound of the present embodiment has excellent stability and the polymer compound of the present embodiment has excellent crosslinkability, so that it is contained in the polymer compound. It is preferably 0.5 to 50 mol %, more preferably 3 to 30 mol %, still more preferably 3 to 20 mol %, relative to the total amount of the constituent units.

The structural unit represented by formula (2') may be contained in only one type or may be contained in two or more types in the polymer compound.

(Preferred Embodiment of Structural Unit Represented by Formula (2) or (2′)))
Examples of structural units represented by formula (2) include structural units represented by formulas (2-1) to (2-30), and structural units represented by formula (2′) include includes, for example, structural units represented by formulas (2′-1) to (2′-9). Among these, structural units represented by formulas (2-1) to (2-30) are preferable, and more preferably formula (2-1 ) to structural units represented by formula (2-15), formula (2-19), formula (2-20), formula (2-23), formula (2-25) or formula (2-30) and more preferably structural units represented by formulas (2-1) to (2-9) or (2-30).

Examples of the polymer compound of the present embodiment include polymer compounds P-1 to P-12 shown in Table 1. Here, "other structural units" mean structural units other than the structural units represented by formula (0), formula (X), formula (Y), formula (2) and formula (2'). .

[In the table, p, q, r, s, t and u represent the molar ratio of each structural unit. p+q+r+s+t+u=100 and 70≦p+q+r+s+t≦100. ]

Examples and preferred ranges of structural units represented by formula (0), formula (X), formula (Y), formula (2) and formula (2′) in the polymer compounds P-1 to P-12 are As mentioned above.

The terminal group of the polymer compound of the present embodiment is preferable because if the polymerization active group remains as it is, there is a possibility that the light emitting property and the luminance life will be reduced when the polymer compound is used for the production of a light emitting device. is a stable group. The terminal group is preferably a group that is conjugated to the main chain, and includes a group that is bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.

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

<Method for producing polymer compound>
Next, a method for producing the polymer compound of the present embodiment will be described.

The polymer compound of the present embodiment includes, for example, a compound represented by the formula (M-0), a compound represented by the formula (M-Y), a compound represented by the formula (MX), and a compound represented by the formula ( It can be produced by condensation polymerization of at least one compound selected from the group consisting of the compound represented by M-2) and the compound represented by formula (M-2′). In this specification, the compounds used for producing the polymer compound of the present embodiment may be collectively referred to as "raw material monomer".

[In the formula,
a ⁰ , R ⁰ , Ar ^Y1 , a ¹ , a ² , nA, n, Ar ³ , L ^A , X, mA, m, c, Ar ⁴ to Ar ⁶ , K ^A , X′, Ar ^Y1 , a ¹ , a ² , Ar ^X1 to Ar ^X4 and R ^X1 to R ^X3 have the same meanings as above.
Z ^C1 to Z ^C10 each independently represent a group selected from the group consisting of substituent group A and substituent group B. ]

For example, when Z ^C1 , Z ^C2 , Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 are groups selected from substituent group A, Z ^C7 , Z ^C8 , Z ^C9 and Z ^C10 are from substituent group B Select the group of choice.

For example, when Z ^C1 , Z ^C2 , Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 are groups selected from Substituent Group B, Z ^C7 , Z ^C8 , Z ^C9 and Z ^C10 are from Substituent Group A Select the group of choice.

<Substituent Group A>
chlorine atom, bromine atom, iodine atom, —O—S(=O) ₂ R ^C1 (wherein R ^C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups have substituents; may be used.).

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

Examples of the group represented by -B(OR ^C2 ) ₂ include groups represented by the following formulae.

A compound having a group selected from substituent group A and a compound having a group selected from substituent group B are subjected to condensation polymerization by a known coupling reaction to form a group selected from substituent group A and substituent group B. The carbon atoms bonded to the group selected from are bonded to each other. Therefore, if a compound having two groups selected from the substituent group A and a compound having two groups selected from the substituent group B are subjected to a known coupling reaction, condensation polymerization of these compounds can be performed. A polymer can be obtained.

Condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, but if necessary, it may be carried out in the presence of a phase transfer catalyst.

Examples of catalysts include bis(triphenylphosphine)palladium(II) dichloride, bis(tris-o-methoxyphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone ) dipalladium(0), palladium complexes such as palladium acetate, tetrakis(triphenylphosphine)nickel(0), [1,3-bis(diphenylphosphino)propane)nickel(II) dichloride, bis(1,4- transition metal complexes such as nickel complexes such as cyclooctadiene)nickel(0); Complexes having ligands such as 1,3-bis(diphenylphosphino)propane and bipyridyl can be mentioned. A catalyst may be used individually by 1 type, or may use 2 or more types together.

The amount of catalyst used is usually 0.00001 to 3 molar equivalents as the amount of transition metal relative to the total number of moles of raw material monomers.

Examples of bases and phase transfer catalysts include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organic bases such as butylammonium; and phase transfer catalysts such as tetrabutylammonium chloride and tetrabutylammonium bromide. Each of the base and the phase transfer catalyst may be used alone or in combination of two or more.

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

Examples of solvents include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N,N-dimethylacetamide, N,N-dimethylformamide, and water. A solvent may be used individually by 1 type, or may use 2 or more types together.

The amount of solvent used is usually 10 to 100,000 parts by mass with respect to the total of 100 parts by mass of raw material monomers.

The reaction temperature for condensation polymerization is usually -100 to 200°C. The condensation polymerization reaction time is usually 1 hour or more.

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., shall be used singly or in combination. When the purity of the polymer compound is low, it can be purified by conventional methods such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

<Composition>
The composition of the present embodiment comprises at least one material selected from the group consisting of a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, an antioxidant, and a solvent; and a polymer compound of

A composition containing a polymer compound and a solvent of the present embodiment (hereinafter sometimes referred to as "ink") is suitable for producing a light-emitting device using a printing method such as an inkjet printing method or a nozzle printing method. .

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 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 blending amount of the solvent is usually 1,000 to 100,000 parts by mass, preferably 2,000 to 20,000 parts by mass, based on 100 parts by mass of the polymer compound of the present embodiment.

[Hole transport material]
The hole-transporting material is classified into a low-molecular-weight compound and a high-molecular-weight compound, preferably a high-molecular-weight compound, and more preferably a high-molecular-weight compound having a cross-linking group.

Polymer compounds include, for example, polyvinylcarbazole and its derivatives; polyarylene and its derivatives having an aromatic amine structure in the side chain or main chain. A polymer compound may be a compound having an electron-accepting site attached thereto. Examples of electron-accepting moieties include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone and the like, preferably fullerene.

In the composition of the present embodiment, the compounding amount of the hole transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, with respect to 100 parts by mass of the polymer compound of the present embodiment. .

The hole-transporting 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, and derivatives thereof.

Examples of polymer compounds include polyphenylene, polyfluorene, and derivatives thereof. The polymeric compounds may be doped with metals.

In the composition of the present embodiment, the amount of the electron-transporting material is usually 1-400 parts by mass, preferably 5-150 parts by mass, per 100 parts by mass of the polymer compound of the present embodiment.

The electron transport material 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, polyquinoxaline, and derivatives thereof; polymers containing an aromatic amine structure in the main chain or side chain; of conductive polymers.

In the composition of the present embodiment, the compounding amount of the hole-injecting material and the electron-injecting material is usually 1 to 400 parts by mass, preferably 5 parts by mass, relative to 100 parts by mass of the polymer compound of the present embodiment. ~150 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]
When 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 types of ions to be doped are anions for hole-injection materials and cations for electron-injection materials. Examples of anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions. Examples of cations include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

The ions to be doped may be one kind or two or more kinds.

[Light emitting 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 triplet emission complexes with iridium, platinum, or europium as the central metal.

Polymer compounds include, for example, phenylene group, naphthalenediyl group, fluorenediyl group, phenanthrenediyl group, dihydrophenanthrenediyl group, group represented by formula (X), carbazoldiyl group, phenoxazinediyl group, phenothiazinediyl , anthracenediyl group, pyrenediyl group, and the like.

The light-emitting material may contain a low-molecular-weight compound and a high-molecular-weight compound, preferably a triplet light-emitting complex and a high-molecular-weight compound.

Iridium complexes such as metal complexes represented by formulas Ir-1 to Ir-5 are preferable as triplet light-emitting complexes.

[In the formula,
R ^D1 to R ^D8 , R ^D11 to R ^D20 , R ^D21 to R ^D26 and R ^D31 to R ^D37 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryl It represents an oxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When a plurality of R ^D1 to R ^D8 , R ^D11 to R ^D20 , R ^D21 to R ^D26 and R ^D31 to R ^D37 are present, they may be the same or different.
-A ^D1 ---A ^D2 - represents an anionic bidentate ligand, A ^D1 and A ^D2 each independently represents a carbon atom, an oxygen atom or a nitrogen atom that bonds to an iridium atom; may be atoms constituting a ring. When there are a plurality of -A ^D1 ---A ^D2 -, they may be the same or different.
n _D1 represents 1, 2 or 3; n _D2 represents 1 or 2; ]

In the metal complex represented by formula Ir-1, at least one of R ^D1 to R ^D8 is preferably a group represented by formula (DA).

In the metal complex represented by formula Ir-2, at least one of R ^D11 to R ^D20 is preferably a group represented by formula (DA).

In the metal complex represented by formula Ir-3, preferably at least one of R ^D1 to R ^D8 and R ^D11 to R ^D20 is a group represented by formula (DA).

In the metal complex represented by formula Ir-4, preferably at least one of R ²¹ to R ²⁶ is a group represented by formula (DA).

In the metal complex represented by formula Ir-5, at least one of R ^D31 to R ^D37 is preferably a group represented by formula (DA).

[In the formula,
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When there are multiple Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
^TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple ^TDAs may be the same or different. ]

m ^DA1 , m ^DA2 and m ^DA3 are usually integers of 10 or less, preferably 5 or less, more preferably 0 or 1. m ^DA1 , m ^DA2 and m ^DA3 are preferably the same integer.

^GDA is preferably a group represented by formulas (GDA-11) to (GDA-15), and these groups may have a substituent.

[In the formula,
*, ** and *** represent binding to Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , respectively.
^RDA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. When there are multiple ^RDAs , they may be the same or different. ]

^RDA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have substituents. may

Ar ^DA1 , Ar ^DA2 and Ar ^DA3 are preferably groups represented by formulas (ArDA-1) to (ArDA-3).

[In the formula,
R ^DA has the same meaning as above.
^RDB 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. If there are multiple ^RDBs , they may be the same or different. ]

^TDA is preferably a group represented by formulas (TDA-1) to (TDA-3).

[In the formula, R ^DA and R ^DB have the same meanings as described above. ]

The group represented by formula (DA) is preferably a group represented by formulas (DA1) to (DA3).

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

np1 is preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and still more preferably 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably zero.

R ^p1 , R ^p2 and R ^p3 are preferably alkyl groups or cycloalkyl groups.

Examples of the anionic bidentate ligand represented by -A ^D1 ---A ^D2 - include ligands represented by the following formulae.

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

As the metal complex represented by formula Ir-1, metal complexes represented by formulas Ir-11 to Ir-13 are preferable. As the metal complex represented by Formula Ir-2, a metal complex represented by Formula Ir-21 is preferable. As the metal complex represented by Formula Ir-3, metal complexes represented by Formulas Ir-31 to Ir-33 are preferred. As the metal complex represented by Formula Ir-4, metal complexes represented by Formulas Ir-41 to Ir-43 are preferable. As the metal complex represented by Formula Ir-5, metal complexes represented by Formulas Ir-51 to Ir-53 are preferable.

[In the formula,
n _D2 represents 1 or 2;
D represents a group represented by formula (DA). A plurality of D may be the same or different.
^RDC 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. Multiple ^RDCs may be the same or different.
^RDD represents an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Multiple ^RDDs may be the same or different. ]

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

In the composition of the present embodiment, the content of the luminescent material is usually 0.1-400 parts by mass with respect to 100 parts by mass of the polymer compound of the present embodiment.

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the polymer compound of the present embodiment and does not inhibit light emission and charge transport. Examples thereof include phenolic antioxidants and phosphorus antioxidants. .

In the composition of this embodiment, the amount of the antioxidant compounded is usually 0.001 to 10 parts by mass with respect to 100 parts by mass of the polymer compound of this embodiment.

The antioxidants may be used singly or in combination of two or more.

<Membrane>
The film contains the polymer compound of the present embodiment or a crosslinked product of the polymer compound of the present embodiment.

That is, the film also includes an insolubilized film in which the polymer compound of the present embodiment is insolubilized in a solvent by crosslinking. The insolubilized film is a film obtained by cross-linking the polymer compound of the present embodiment with an external stimulus such as heating or light irradiation. Since the insolubilized film is substantially insoluble in a solvent, it can be suitably used for lamination of light-emitting devices.

The heating temperature for cross-linking the film is usually 25 to 300°C, preferably 50 to 250°C, more preferably 150 to 200°C, because the luminous efficiency is improved.

The types of light used for light irradiation for cross-linking the film are, for example, ultraviolet light, near-ultraviolet light, and visible light.

The film is suitable as a light-emitting layer, hole-transporting layer or hole-injecting layer in a light-emitting device.

The film is formed by using ink, for example, spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, screen printing. , flexographic printing, offset printing, inkjet printing, capillary coating, and nozzle coating.

The thickness of the film is usually 1 nm to 10 μm.

<Light emitting element>
The light-emitting device of the present embodiment is a light-emitting device such as organic electroluminescence obtained using the polymer compound of the present embodiment. There is a light emitting device including a crosslinked product in which the polymer compound of the present embodiment is crosslinked intramolecularly, intermolecularly, or both.

The configuration of the light-emitting device of this embodiment includes, for example, a configuration having electrodes consisting of an anode and a cathode, and a layer obtained using the polymer compound of this embodiment provided between the electrodes.

[Layer structure]
The layer obtained using the polymer compound of the present embodiment is usually one or more layers selected from a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer. 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. These layers are formed by dissolving the light-emitting material, the hole-transporting material, the hole-injecting material, the electron-transporting material, and the electron-injecting material in the above-described solvent, preparing an ink, and using the ink in the same manner as in the above-described film formation. method.

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 embodiment preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light emitting layer. From the viewpoint of electron injection 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, the electron-transporting layer, the light-emitting layer, the hole-injecting layer, and the electron-injecting layer include, in addition to the polymer compound of the present embodiment, the above-described hole-transporting material, electron-transporting material, Light-emitting materials, hole-injecting materials, and electron-injecting materials are included.

The material for the hole-transport layer, the material for the electron-transport layer, and the material for the light-emitting layer are used in forming the hole-transport layer, the electron-transport layer, and the layers adjacent to the light-emitting layer, respectively, in the fabrication of the light-emitting device. It is preferred that the material has cross-linking groups to avoid dissolving the material in the solvent when dissolved 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 embodiment, 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 from powder A vapor deposition method, a method of forming a film from a solution or a molten state, and a method of forming a film from a solution or a molten state, for example, can be used when using a polymer compound.

The order, number, and thickness of the layers to be laminated should be adjusted in consideration of the luminous efficiency and device life.

[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 device of this embodiment is useful for, for example, displays and lighting.

Although the preferred embodiments of the present invention have been described above, the present invention is not limited to the above embodiments.

The present invention will be described in more detail below with reference to examples, but the present invention 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 any of the following size exclusion chromatography (SEC) using tetrahydrofuran as a moving bed. obtained by The SEC measurement conditions are as follows.

A polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. The mobile phase was run at a flow rate of 1.0 mL/min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Tosoh, trade name: UV-8320GPC) was used as a detector.

NMR was measured by the following method.
5 to 10 mg of a measurement sample is 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. Alternatively, it was dissolved in methylene dichloride and measured using an NMR device (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).

The value of high performance liquid chromatography (HPLC) area percentage was used as an indicator of the purity of the compound. 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 used was Kaseisorb LC ODS 2000 (manufactured by Tokyo Kasei Kogyo) or an ODS column with equivalent performance. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as the detector.

TLC-MS was measured by the following method.
A measurement sample is dissolved in any solvent of toluene, tetrahydrofuran or 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.

<Synthesis example 1> Synthesis of compound 1D

(Stage 1: Synthesis of compound 1A)
After making the inside of the reaction vessel a nitrogen atmosphere, 3-bromoiodobenzene (300.0 g), 3-biphenylboronic acid (200.0 g), tetrakis(triphenylphosphine) palladium (0) (22.2 g), potassium carbonate (418.8 g), ion-exchanged water (1600 mL), ethanol (800 mL) and toluene (1600 mL) were added and stirred at 75° C. for 9 hours. After the obtained reaction solution was cooled to room temperature, it was filtered through a filter covered with celite, and the aqueous layer was removed from the obtained filtrate. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (n-hexane solvent) and dried at 50° C. under reduced pressure to obtain compound 1A (278.2 g). The HPLC area percentage value of compound 1A was 99.5% or more.

(Stage 2: Synthesis of compound 1C)
After creating a nitrogen atmosphere in the reaction vessel, compound 1A (220.6 g) and tetrahydrofuran (1200 mL) were added, and the mixture was cooled to -70°C. A 1.0 Msec-butyllithium n-hexane/cyclohexane solution (697 mL) was slowly added thereto, and the mixture was stirred at -70°C for 1 hour. Compound 1B (120.0 g) and tetrahydrofuran (360 mL) were slowly added dropwise thereto, followed by stirring at -65°C for 1 hour. After slowly adding methanol (48 mL) thereto, the resulting reaction solution was brought to room temperature, ion-exchanged water (1800 mL) and toluene (1560 mL) were slowly added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, dried with magnesium sulfate, and then filtered. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was washed with n-heptane, recrystallized with toluene and n-heptane, and dried at 50° C. under reduced pressure to obtain compound 1C (244.7 g). The LC area percentage value of compound 1C was 99.5% or more.

(Stage 3: Synthesis of Compound 1D)
After making the inside of reaction container into nitrogen atmosphere, the compound 1C (240.0g) and toluene (7200 mL) were added, and it cooled at 0 degreeC. Sulfuric acid (44.4 g) was slowly added thereto, and the mixture was stirred at 0°C for 1 hour. After that, the temperature was raised to 5° C. and the mixture was further stirred for 4 hours. After slowly adding ion-exchanged water (2400 mL) thereto and cooling the resulting reaction solution to room temperature, the aqueous layer was removed. The resulting organic layer was washed with ion-exchanged water and an aqueous sodium hydrogencarbonate solution, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized with toluene and ethanol and dried under reduced pressure at 50° C. to obtain compound 1D (197.4 g). The HPLC area percentage value of compound 1D was 99.5% or more.

The results of NMR measurement of compound 1D were as follows.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.67-7.63 (m, 6H), 7.59-7.53 (m, 10H), 7.47-7.30 (m, 14H), 7.29-7.18 (m, 2H).

<Synthesis example 2> Synthesis of compound 2D

(Stage 1: synthesis of compound 2B)
After creating a nitrogen atmosphere in the reaction vessel, compound 2A (90.2 g) and tetrahydrofuran (361 mL) were added, and the mixture was cooled to -70°C. A 1.0 M sec-butyllithium n-hexane/cyclohexane solution (224 mL) was slowly added thereto, and the mixture was stirred at -70°C for 1 hour. Compound 1B (36.1 g) and tetrahydrofuran (108 mL) were slowly added dropwise thereto, followed by stirring at -65°C for 1 hour. After slowly adding methanol (14 mL), the resulting reaction solution was brought to room temperature, ion-exchanged water (542 mL) and heptane (469 mL) were slowly added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, dried with magnesium sulfate, and then filtered. The resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mixed solvent of toluene and n-hexane) and dried at 50° C. under reduced pressure to obtain compound 2B (86.7 g). The LC area percentage value of compound 2B was 99.5% or more.

(Stage 2: Synthesis of compound 2C)
After making the inside of reaction container into nitrogen atmosphere, the compound 2B (86.3g) and toluene (863 mL) were added, and it cooled at 0 degreeC. Sulfuric acid (8.7 g) was slowly added thereto, and the mixture was stirred at 0°C for 1 hour. After slowly adding ion-exchanged water (783 mL) and cooling the resulting reaction solution to room temperature, the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mixed solvent of toluene and n-hexane) and dried at 50° C. under reduced pressure to obtain compound 2C (64.1 g). The HPLC area percentage value of compound 2C was greater than 99.5%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.72-7.64 (m, 6H), 7.60-7.49 (m, 8H), 7.48-7.30 (m, 12H), 7.24-7.14 (m, 4H), 2.64 (t, 4H), 1.70-1.60 (m, 4H), 1.40-1.25 (m , 12H), 0.89(t, 6H).

(Stage 3: Synthesis of Compound 2D)
After making the inside of the reaction vessel a nitrogen atmosphere, compound 2C (25.4 g), bis(pinacolato)diboron (16.3 g), dimethoxyethane (254 mL), [1,1′-bis(diphenylphosphino)ferrocene]palladium. (II) Dichloride/dichloromethane adduct (657 mg) and potassium acetate (15.8 g) were added and stirred at 80° C. for 2 hours. After adding celite (28.0 g) to the resulting reaction solution, the mixture was filtered through a filter lined with silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. After washing the resulting crude product with acetonitrile, toluene and activated carbon were added and the mixture was stirred at room temperature for 30 minutes. Then, it was filtered through a filter covered with celite, and the obtained filtrate was concentrated under reduced pressure, recrystallized with toluene and acetonitrile, and dried under reduced pressure at 50°C to obtain compound 2D (23.3 g) as a white solid. rice field. The HPLC area percentage value for compound 2D was greater than 99.5%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 7.88-7.81 (m, 6H), 7.71-7.68 (m, 2H), 7.59-7.50 (m, 6H), 7.45-7.29 (m, 12H), 7.25 (d, 2H), 7.16 (d, 2H), 2.64 (t, 4H), 1.70- 1.56 (m, 4H), 1.40-1.25 (m, 36H), 0.88 (t, 6H).

<Synthesis example 3> Synthesis of compound 3C

(Stage 1: synthesis of compound 3A)
After creating an inert gas atmosphere in the reaction vessel, compound 2A (58.19 g) and dehydrated THF (600 ml) were added, cooled to -70°C, and 86 ml of n-butyllithium (1.64M n-hexane solution) was added. It was added dropwise and kept warm for 2 hours. After adding 2,7-dibromo-9-fluorenone (40.00 g) and keeping the temperature for 2 hours, methanol was added dropwise and the temperature was raised to room temperature. Toluene (450 ml) and ion-exchanged water (450 ml) were added and separated. The organic layer was separated and washed twice with ion-exchanged water (450 ml), magnesium sulfate was added, dehydrated, filtered, and the resulting solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mobile phase: mixed solvent of hexane and toluene) to obtain compound 3A (75.5 g).

(Stage 2: Synthesis of compound 3B)
After the reaction vessel was filled with an inert gas atmosphere, compound 3A (67.90 g) and dehydrated dichloromethane (340 ml) were added and dissolved, and triethylsilane (25.0 g) was added. After cooling to 0° C., boron trifluoride diethyl ether complex (41.71 g) was added dropwise, and the temperature was maintained for 3 hours. Dichloromethane (340 ml) and ion-exchanged water (340 ml) were added, and after liquid separation, the organic layer was separated and washed with 5% by mass aqueous sodium hydrogencarbonate solution (340 ml) and ion-exchanged water (340 ml), 340 ml of heptane was added, and sulfuric acid was added. After dehydration by adding magnesium, the resulting solution was concentrated under reduced pressure to obtain compound 3B (66.10 g).

(Stage 3: Synthesis of compound 3C)
After the reaction vessel was filled with an inert gas atmosphere, compound 3B (21.02 g) and dehydrated THF (84 ml) were added and dissolved.
Separately, a reaction vessel with an inert gas atmosphere was prepared, and sodium hydride (60% by mass, dispersed in liquid paraffin, 1.47 g), dehydrated THF (63 ml), and 1-bromohexane (16.36 g) were added. , the THF solution of compound 3B prepared above was added dropwise to this solution and stirred for 3 hours. Toluene (170 ml) and ion-exchanged water (85 ml) were added dropwise thereto, and after liquid separation, the organic layer was separated and washed twice with ion-exchanged water (100 ml). Magnesium sulfate was added thereto, dehydrated, filtered through a filter covered with celite, and the obtained solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mobile phase: mixed solvent of hexane and toluene) to obtain compound 3C (23.99 g) as a white solid.
The HPLC area percentage value of compound 3C was greater than 99.5%.

<Synthesis example 4> Synthesis of compound 4C

(Stage 1: synthesis of compound 4A)
After the reaction vessel was filled with an inert gas atmosphere, 9-phenyl-9-fluorenol (46.08 g) and dehydrated dichloromethane (370 ml) were added and dissolved, and triethylsilane (56.83 g) was added. After cooling to 0° C., boron trifluoride diethyl ether complex (44.81 g) was added dropwise, and the temperature was maintained for 2 hours. Dichloromethane (230 ml) and 5% by mass aqueous sodium carbonate solution (460 ml) were added thereto, and after liquid separation, the organic layer was separated and washed twice with deionized water (100 ml). Magnesium sulfate was added thereto, and after dehydration, the resulting solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was crystallized using a mixed solvent of toluene and acetonitrile to obtain compound 4A (40.90 g).
TLC-MS (DART) m/z = 243 ([M+H] ⁺ ) (Exact Mass: 242)
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm) = 5.05 (1H, s), 7.07-7.10 (2H, m), 7.19-7.29 (5H, m), 7.31 (2H, d), 7.37 (2H, t), 7.80 (2H, d)

(Stage 2: Synthesis of Compound 4B)
After the reaction vessel was filled with an inert gas atmosphere, compound 4A (29.00 g), 1-bromo-6-chlorohexane (95.5 g), and dehydrated THF (175 ml) were added and dissolved.
Separately, a reaction vessel with an inert gas atmosphere was prepared, sodium hydride (60% by mass, dispersed in liquid paraffin, 5.27 g) and dehydrated THF (29 ml) were added, and compound 4A prepared above was added to this solution. A THF solution was added dropwise, and the mixture was stirred at 20°C for 8 hours and then stirred at 30°C for 5 hours. Toluene (230 ml) and ion-exchanged water (115 ml) were added dropwise thereto, and after liquid separation, the organic layer was separated and washed three times with ion-exchanged water (145 ml). Magnesium sulfate was added thereto, and after dehydration, the resulting solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mobile phase: mixed solvent of hexane and toluene) to obtain compound 4B (41.58 g).
TLC-MS (DART) m/z = 361 ([M+H] ⁺ ) (Exact Mass: 360)
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm) = 0.69-0.78 (2H, m), 1.13-1.28 (4H, m), 1.55-1.63 (2H , m), 2.43-2.48 (2H, m), 3.41 (2H, t), 7.12-7.27 (9H, m), 7.34 (2H, dt), 7. 75 (2H, d)

(Stage 3: Synthesis of compound 4C)
After the reaction vessel was filled with an inert gas atmosphere, compound 4B (41.10 g), sodium iodide (85.42 g) and acetone (410 ml) were added, and the mixture was kept at 60°C for 29 hours. After cooling to 20° C., ion-exchanged water (120 ml) and hexane (410 ml) were added to separate the layers, and the organic layer was separated and washed three times with ion-exchanged water (120 ml). Magnesium sulfate was added thereto, and after dehydration, the resulting solution was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized with heptane to obtain compound 4C (46.11 g).
TLC-MS (DART) m/z = 453 ([M+H] ⁺ ) (Exact Mass: 452)
¹ H-NMR (CDCl ³ , 400 MHz) δ (ppm) = 0.69-0.77 (2H, m), 1.14-1.24 (4H, m), 1.60-1.68 (2H , m), 2.43-2.48 (2H, m), 3.07 (2H, t), 7.14-7.27 (9H, m), 7.34 (2H, dt), 7. 75 (2H, d)

(Stage 4: Synthesis of Compound 4D)
After the reaction vessel was filled with an inert gas atmosphere, compound 3B (21.00 g), compound 4C (16.42 g), and dehydrated THF (125 ml) were added and dissolved.
Separately, a reaction vessel with an inert gas atmosphere was prepared, sodium hydride (60% by mass, dispersed in liquid paraffin, 1.45 g) and dehydrated DMF (53 ml) were added and cooled to 0°C. After the THF solution of compound 3B and compound 4C prepared above was added dropwise to this solution, the temperature was raised to 25° C. and the mixture was stirred for 3.5 hours. 100 ml of toluene and 100 ml of ion-exchanged water were added dropwise thereto, and after liquid separation, the organic layer was separated and washed three times with 100 ml of ion-exchanged water. Magnesium sulfate was added thereto, and after dehydration, the resulting solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by reverse-phase silica gel column chromatography (mobile phase: mixed solvent of acetonitrile and ethyl acetate) to obtain compound 4D (25.56 g) as a white solid. The HPLC area percentage value of compound 4D was greater than 99.5%.
TLC-MS (DART) m/z = 958 ([M] ⁺ ) (Exact Mass: 958)
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm) = 0.53-0.64 (4H, m), 0.89 (3H, t), 0.93-1.04 (4H, m), 1.28-1.41 (6H, m), 1.61-1.70 (2H, m), 2.31-2.37 (4H, m), 2.67 (2H, t), 7. 00 (1H, d), 7.10-7.23 (11H, m), 7.27-7.38 (6H, m), 7.40-7.49 (7H, m), 7.53- 7.57 (3H, m), 7.66 (1H, brs), 7.71 (2H, d)

<Synthesis example 5> Synthesis of compound 5D

(Stage 1: synthesis of compound 5A)
After making the inside of the reaction vessel an inert gas atmosphere, compound 2A (120.01 g) and dehydrated THF (1200 ml) were added and dissolved. 310 ml of hexane solution) was added dropwise, and the mixture was kept warm for 1.5 hours. kept warm. The temperature was raised to 0° C., methanol (120 ml) was added dropwise, and the solvent was concentrated under reduced pressure. Toluene was added thereto, and the solution was separated and washed three times with ion-exchanged water, and then the solvent was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mobile phase: mixed solvent of hexane and toluene) to obtain compound 5A (117.36 g).
TLC-MS (DART) m/z = 440 ([M] ⁺ ) (Exact Mass: 440)

(Stage 2: Synthesis of Compound 5B)
After making the inside of the reaction vessel an inert gas atmosphere, compound 5A (65.94 g), 1-bromo-3-iodobenzene (42.36 g), toluene (500 ml), 20 mass% tetraethylammonium hydroxide aqueous solution (330 g). , and tetrakis(triphenylphosphine)palladium(0) (3.45 g) were added, and the mixture was kept at 70° C. for 4 hours. After cooling to room temperature, the liquids were separated, and the organic phase was separated and washed three times with 600 ml of water. Activated carbon was added thereto, and after stirring for 30 minutes, the mixture was filtered through a filter covered with silica gel. The resulting solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mobile phase: mixed solvent of hexane and toluene) to obtain compound 5B (66.02 g).
TLC-MS (DART) m/z = 469 ([M] ⁺ ) (Exact Mass: 468)

(Stage 3: Synthesis of Compound 5C)
After making the inside of the reaction vessel an inert gas atmosphere, compound 5B (41.03 g) and dehydrated THF (415 ml) were added and dissolved, cooled to -70°C, and sec-butyllithium (1.23M cyclohexane/n- 70 ml of hexane solution) was added dropwise, and the temperature was maintained for 1.5 hours. A solution of compound 1B (14.40 g) dissolved in dehydrated THF (73 ml) was added dropwise, and the mixture was kept warm for 2 hours. After methanol was added dropwise thereto, the temperature was raised to room temperature, and the solvent was concentrated under reduced pressure. Toluene was added, and the solution was separated and washed four times with ion-exchanged water, then magnesium sulfate was added for dehydration, and the solution was filtered. The resulting solution was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mobile phase: mixed solvent of hexane and toluene) to obtain compound 5C (43.09 g).
TLC-MS (DART) m/z = 1116 ([M] ⁺ ) (Exact Mass: 1116)

(Stage 4: Synthesis of compound 5D)
After creating an inert gas atmosphere in the reaction vessel, compound 5C (42.95 g) and toluene (445 ml) were added and dissolved, cooled to 0°C, concentrated sulfuric acid (4.02 g) was added dropwise, and the mixture was stirred for 3 hours. did. There, ion-exchanged water (430 ml) and 5% by mass aqueous sodium hydrogencarbonate solution (430 ml) were separately washed. Activated carbon and magnesium sulfate were added thereto, and after stirring for 1 hour, the mixture was filtered through a filter covered with silica gel. The resulting solution was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized by silica gel column chromatography (mobile phase is a mixed solvent of hexane and toluene) and heptane and ethanol to obtain compound 5D (36.95 g) as a white solid. The HPLC area percentage value of compound 5D was greater than 99.5%.
TLC-MS (DART) m/z = 1099 ([M] ⁺ ) (Exact Mass: 1098)

<Synthesis example 6> Synthesis of compound 6B

(Stage 1: synthesis of compound 6B)
After the reaction vessel was filled with a nitrogen atmosphere, sodium hydride (1.3 g) and N,N-dimethylformamide (49.2 mL) were added and stirred at 25°C. Compound 6A (21.0 g), compound 4A (7.2 g) and tetrahydrofuran (105 mL), which had been mixed and dissolved in advance, were slowly added thereto and stirred at 55° C. for 2 hours. After cooling the resulting reaction solution to room temperature, toluene (168 mL) and ion-exchanged water (84 mL) were added and mixed, and the mixture was filtered through a filter covered with celite, and the aqueous layer was removed from the resulting filtrate. . The obtained organic layer was washed with ion-exchanged water, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized by silica gel column chromatography (mobile phase is a mixed solvent of hexane and toluene) and toluene and methanol, and dried under reduced pressure to obtain compound 6B (20.3 g) as a white solid. . The HPLC area percentage value of compound 6B was greater than 99.5%.
¹ H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 7.73-7.71 (d, 2H), 7.54-7.52 (d, 2H), 7.44-7.42 (m , 2H), 7.37-7.30 (m, 2H), 7.24-7.23 (dd, 2H), 7.21-7.19 (m, 3H), 7.17-7.12 (m, 6H), 6.82 (s, 1H), 6.65-6.65 (d, 2H), 2.47-2.43 (t, 4H), 2.36-2.32 (m , 2H), 2.28-2.24 (m, 2H), 1.52-1.46 (m, 4H), 1.25 (m, 12H), 0.97-0.96 (m, 4H) ), 0.88-0.84 (t, 6H), 0.59-0.52 (d, 4H)

<Synthesis Examples PM1 to PM9: Synthesis and acquisition of compounds PM1 to PM9>
Compounds PM1 and PM5 were synthesized according to the method described in JP-A-2011-174062.
Compound PM2 was synthesized according to the method described in WO 2005/049546.
Compound PM3 was synthesized according to the method described in WO 2002/045184.
Compound PM4 was synthesized according to the method described in JP-A-2008-106241.
Compound PM6 was synthesized according to the method described in JP-A-2012-144722.
Compound PM7 was synthesized according to the method described in WO2002/092723.
Compound PM8 was synthesized according to the method described in JP-A-2004-143419.
Compound PM9 was synthesized according to the method described in JP-A-2010-031259.

<Synthesis Examples PM10 to PM12: Synthesis and acquisition of compounds PM10 to PM12>
Compound PM10 and compound PM12 were synthesized according to the method described in JP-A-2010-189630.
Compound PM11 was synthesized according to the method described in WO 2012/086671.

<Synthesis Example G1> Synthesis of Phosphorescent Compound G1 Phosphorescent compound G1 was synthesized according to the method described in International Publication No. 2009/131255.

<Synthesis Example 2> Synthesis of polymer compound IP1 Polymer compound IP1 was synthesized by the method described in JP-A-2012-144722 using compound PM1, compound PM2, compound PM3, and compound PM4.

According to the theoretical values obtained from the amounts of the raw materials, the polymer compound IP1 has a structural unit derived from the compound PM1, a structural unit derived from the compound PM2, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM4. It is a copolymer composed of derived structural units in a molar ratio of 50:30:12.5:7.5.

<Example 1> Synthesis of polymer compound P1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound PM5 (1.28372 g), compound 1D (0.89649 g), compound PM3 (0.19881 g) , compound PM8 (0.07961 g), compound PM9 (0.20980 g), dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.58 mg) and toluene (30 mL) were added and heated to 80°C.
(Step 2) A 20% by mass tetraethylammonium hydroxide aqueous solution (20 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 3 hours. After the reaction, phenylboronic acid (89.5 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.61 mg) were added thereto and refluxed for 3 hours. After that, the reaction solution was cooled to room temperature, the aqueous layer was removed, and the mixture was washed once with ion-exchanged water, once with a 0.15% by mass aqueous sodium N,N-diethyldithiocarbamate solution, and twice with 10% by mass hydrochloric acid. , and washed twice with a 3% by mass aqueous ammonia solution and twice with deionized water. The obtained solution was dehydrated under reduced pressure to obtain a toluene solution from which water was removed. This toluene solution was purified by passing through an alumina column through which toluene had been passed in advance. When the purified liquid was added dropwise to methanol and stirred, a precipitate was formed. The precipitate was collected by filtration and dried to obtain polymer compound P1 (1.45 g). The Mn of the polymer compound P1 was 9.5×10 ⁴ and the Mw was 2.2×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials, the polymer compound P1 has a structural unit derived from the compound PM5, a structural unit derived from the compound 1D, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM8. It is a copolymer composed of structural units derived from compound PM9 and structural units derived from compound PM9 in a molar ratio of 50:32:10:3:5.

<Comparative Example 1> Synthesis of polymer compound P2 (Step 1) in the synthesis of polymer compound P1 was performed as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound PM5 (1.29934 g) and compound PM7 (0.29934 g) were added. 90788 g), compound PM3 (0.19700 g), compound PM8 (0.07888 g), compound PM9 (0.20792 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (1.54 mg) and toluene (30 mL) were added. , and heated to 80° C.”, 1.48 g of polymer compound P2 was obtained in the same manner as in the synthesis of polymer compound P1. The Mn of the polymer compound P2 was 8.0×10 ⁴ and the Mw was 1.9×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials, the polymer compound P2 has a structural unit derived from the compound PM5, a structural unit derived from the compound PM7, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM8. It is a copolymer composed of structural units derived from compound PM9 and structural units derived from compound PM9 in a molar ratio of 50:32:10:3:5.

<Comparative Example 2> Synthesis of polymer compound P3 Polymer compound P3 was prepared by It was synthesized according to the method described in JP-A-2012-144722.

According to the theoretical values obtained from the amounts of the raw materials, the polymer compound P3 has a structural unit derived from the compound PM5, a structural unit derived from the compound PM6, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM8. It is a copolymer composed of structural units derived from compound PM9 and structural units derived from compound PM9 in a molar ratio of 50:32:10:3:5.

<Example 2> Synthesis of polymer compound P4 (Step 1) in the synthesis of polymer compound P1 was performed by changing the inside of the reaction vessel to an inert gas atmosphere, followed by compound PM10 (1.00964 g) and compound 2C (1.00964 g). 56606 g), compound PM12 (0.26264 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (1.82 mg) and toluene (30 mL) were added and heated to 80° C. After the reaction, phenylboronic acid was added thereto. (0.10 g) and dichlorobis(tris-o-methoxyphenylphosphine) palladium (1.82 mg) were added and refluxed for 3 hours. 1.43 g of molecular compound P4 was obtained. The Mn of the polymer compound P4 was 1.0×10 ⁵ and the Mw was 2.1×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials charged, the polymer compound P4 has a structural unit derived from the compound PM10, a structural unit derived from the compound 2C, and a structural unit derived from the compound PM12 of 50: It is a copolymer composed in a molar ratio of 40:10.

<Example 3> Synthesis of polymer compound P5 (Step 1) in the synthesis of polymer compound P1 was performed as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound PM10 (3.61834 g), compound 3C (4. 38134 g), compound PM12 (0.97496 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (6.72 mg) and toluene (90 mL) were added and heated to 80° C. The reaction solution was added with 20% by mass hydroxylation. An aqueous tetraethylammonium solution (60 mL) was added dropwise and refluxed for 3 hours, after which phenylboronic acid (0.37 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (6.72 mg) were added. The mixture was refluxed for 3 hours." Except that, 4.76 g of polymer compound P5 was obtained in the same manner as in the synthesis of polymer compound P1. The Mn of the polymer compound P5 was 1.3×10 ⁵ and the Mw was 3.1×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials charged, the polymer compound P5 has a structural unit derived from the compound PM10, a structural unit derived from the compound 3C, and a structural unit derived from the compound PM12 of 50: It is a copolymer composed in a molar ratio of 40:10.

<Example 4> Synthesis of polymer compound P6 (Step 1) in the synthesis of polymer compound P1 was performed as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound PM10 (0.98952 g), compound 4D (1. 56892 g), compound PM12 (0.26007 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (1.82 mg) and toluene (45 mL) were added and heated to 80° C. The reaction solution was added with 20% by mass hydroxylation. An aqueous tetraethylammonium solution (30 mL) was added dropwise and refluxed for 3 hours, after which phenylboronic acid (0.10 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.82 mg) were added. 1.30 g of polymer compound P6 was obtained in the same manner as in the synthesis of polymer compound P1, except that the content was refluxed for 3 hours. The Mn of the polymer compound P6 was 1.1×10 ⁵ and the Mw was 2.2×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials charged, the polymer compound P6 has a structural unit derived from the compound PM10, a structural unit derived from the compound 4D, and a structural unit derived from the compound PM12 of 50: It is a copolymer composed in a molar ratio of 40:10.

<Example 5> Synthesis of polymer compound P7 (Step 1) in the synthesis of polymer compound P1 was performed as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound PM10 (0.88797 g), compound 5D (1. 63526 g), compound PM12 (0.23338 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (1.61 mg) and toluene (45 mL) were added and heated to 80° C. The reaction solution was added with 20% by mass hydroxylation. An aqueous tetraethylammonium solution (30 mL) was added dropwise and the mixture was refluxed for 3 hours, after which phenylboronic acid (0.09 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.61 mg) were added. 1.29 g of polymer compound P7 was obtained in the same manner as in the synthesis of polymer compound P1, except that the content was refluxed for 3 hours. The Mn of the polymer compound P7 was 1.0×10 ⁵ and the Mw was 2.0×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials charged, the polymer compound P7 has a structural unit derived from the compound PM10, a structural unit derived from the compound 5D, and a structural unit derived from the compound PM12 of 50: It is a copolymer composed in a molar ratio of 40:10.

<Comparative Example 3> Synthesis of polymer compound P8 (Step 1) in the synthesis of polymer compound P1 was performed by changing the reaction vessel to an inert gas atmosphere, followed by compound PM10 (3.18058 g) and compound PM7 (4.18058 g). 53300 g), compound PM12 (0.90461 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (6.72 mg) and toluene (90 mL) were added and heated to 80° C. The reaction solution was added with 20% by mass hydroxylation. An aqueous tetraethylammonium solution (60 mL) was added dropwise and the mixture was refluxed for 3 hours, after which phenylboronic acid (0.35 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (6.72 mg) were added. The mixture was refluxed for 3 hours." Except that, 4.69 g of polymer compound P8 was obtained in the same manner as in the synthesis of polymer compound P1. The Mn of the polymer compound P8 was 7.7×10 ⁴ and the Mw was 1.9×10 ⁵ .

According to the theoretical values obtained from the amount of the raw material charged, the polymer compound P8 has a structural unit derived from the compound PM10, a structural unit derived from the compound PM7, and a structural unit derived from the compound PM12 of 50: It is a copolymer composed in a molar ratio of 40:10.

<Comparative Example 4> Synthesis of polymer compound P9 (Step 1) in the synthesis of polymer compound P1 was changed to "After the inside of the reaction vessel was made into an inert gas atmosphere, compound PM10 (3.08001 g), compound 6B (4. 66435 g), compound PM12 (0.82990 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (6.72 mg) and toluene (90 mL) were added and heated to 80° C. The reaction solution was added with 20% by mass hydroxide. An aqueous tetraethylammonium solution (60 mL) was added dropwise and the mixture was refluxed for 3 hours, after which phenylboronic acid (0.31 g) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (6.72 mg) were added. The mixture was refluxed for 3 hours." Except that, 5.17 g of polymer compound P9 was obtained in the same manner as in the synthesis of polymer compound P1. The Mn of the polymer compound P9 was 9.3×10 ⁴ and the Mw was 1.9×10 ⁵ .

According to the theoretical values obtained from the amounts of the starting materials, the polymer compound P9 has a structural unit derived from the compound PM10, a structural unit derived from the compound 6B, and a structural unit derived from the compound PM12, which is 50: It is a copolymer composed in a molar ratio of 40:10.

<Comparative Example 5> Synthesis of polymer compound P10 Polymer compound P10 was synthesized using compound PM10, compound PM11 and compound PM12 according to the method described in JP-A-2012-036388. The Mn of the polymer compound P10 was 9.6×10 ⁴ and the Mw was 2.2×10 ⁵ .

In the polymer compound P10, the theoretical value obtained from the amount of the charged raw material has a ratio of structural units derived from the compound PM10, structural units derived from PM11, and structural units derived from the compound PM12 at 50:40. : 10 molar ratio.

<Example 6> Synthesis of polymer compound P11 (Step 1) in the synthesis of polymer compound P1 was performed as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound 2D (1.46367 g) and compound PM2 (0.46367 g) were added. 78716 g), compound PM3 (0.19928 g), compound PM4 (0.11534 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (1.27 mg) and toluene (30 mL) were added and heated to 80°C. 2.00 g of polymer compound P11 was obtained in the same manner as in the synthesis of polymer compound P1, except that The Mn of the polymer compound P11 was 1.0×10 ⁵ and the Mw was 2.2×10 ⁵ .

According to the theoretical values obtained from the amounts of the raw materials, the polymer compound P11 has a structural unit derived from the compound 2D, a structural unit derived from the compound PM2, a structural unit derived from the compound PM3, and a structural unit derived from the compound PM4. It is a copolymer composed of derived structural units in a molar ratio of 50:30:12.5:7.5.

<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, a film of ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, is formed with a thickness of 35 nm by spin coating, and heated on a hot plate at 170° C. for 15 minutes in an air atmosphere. A hole injection layer was thus formed.
(Formation of hole transport layer)
Polymer compound IP1 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method, and was heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere. A pore transport layer was formed.
(Formation of light-emitting layer)
Polymer compound P1 was dissolved in xylene at a concentration of 1.2% by mass. Using the obtained xylene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and light was emitted by heating on a hot plate at 170° C. for 10 minutes in a nitrogen gas atmosphere. formed a layer.
(Formation of cathode)
After reducing the pressure of the substrate on which the light-emitting layer is formed to 1×10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride of about 7 nm is deposited on the light-emitting layer as a cathode, and then on the sodium fluoride layer, About 120 nm of aluminum was evaporated. After vapor deposition, the light-emitting device D1 was produced by sealing with a glass substrate.
(Evaluation of Light Emitting Element)
By applying a voltage to the light emitting element D1, EL light emission having the maximum peak wavelength of the emission spectrum at 460 nm was observed. Constant current driving was performed at an initial luminance of 1000 cd/m ² , and the time until the luminance reached 70% of the initial luminance (hereinafter also referred to as “LT70”) was measured. Table 2 shows the results.

<Comparative Example CD1> Production and Evaluation of Light-Emitting Device CD1 A light-emitting device CD1 was produced in the same manner as in Example D1, except that polymer compound P2 was used instead of polymer compound P1 in Example D1.
By applying a voltage to the light emitting element CD1, EL light emission having the maximum peak wavelength of the emission spectrum at 460 nm was observed. It was driven at a constant current with an initial luminance of 1000 cd/m ² and LT70 was measured. Table 2 shows the results.

<Comparative Example CD2> Production and Evaluation of Light-Emitting Device CD2 A light-emitting device CD1 was produced in the same manner as in Example D1, except that polymer compound P3 was used instead of polymer compound P1 in Example D1.
By applying a voltage to the light emitting element CD2, EL light emission having the maximum peak wavelength of the emission spectrum at 460 nm was observed. It was driven at a constant current with an initial luminance of 1000 cd/m ² and LT70 was measured. Table 2 shows the results.

<Example D2> Production and Evaluation of Light-Emitting Device D2 (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, a film of ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, is formed with a thickness of 35 nm by spin coating, and heated on a hot plate at 250° C. for 15 minutes in an air atmosphere. A hole injection layer was thus formed.
(Formation of hole transport layer)
Polymer compound IP1 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method, and was heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere. A pore transport layer was formed.
(Formation of light-emitting layer)
Polymer compound P4 and phosphorescent compound G1 (polymer compound P4/phosphorescent compound G1=60% by mass/40% by mass) were dissolved in xylene at a concentration of 2.0% by mass. Using the obtained xylene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 170° C. for 10 minutes in a nitrogen gas atmosphere. .
(Formation of cathode)
After reducing the pressure of the substrate on which the light-emitting layer is formed to 1×10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride of about 7 nm is deposited on the light-emitting layer as a cathode, and then on the sodium fluoride layer, About 120 nm of aluminum was evaporated. After vapor deposition, the light-emitting device D2 was produced by sealing with a glass substrate.
(Evaluation of Light Emitting Element)
By applying a voltage to the light emitting element D2, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Example D3> Production and Evaluation of Light-Emitting Device D3 A light-emitting device D3 was produced in the same manner as in Example D2, except that polymer compound P5 was used instead of polymer compound P4 in Example D2.
By applying a voltage to the light emitting element D3, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Example D4> Production and Evaluation of Light-Emitting Device D4 A light-emitting device D4 was produced in the same manner as in Example D2, except that polymer compound P6 was used instead of polymer compound P4 in Example D2.
By applying a voltage to the light emitting element D4, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Example D5> Production and Evaluation of Light-Emitting Device D5 A light-emitting device D5 was produced in the same manner as in Example D2, except that polymer compound P7 was used instead of polymer compound P4 in Example D2.
By applying a voltage to the light emitting element D5, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Comparative Example CD3> Production and Evaluation of Light-Emitting Device CD3 A light-emitting device CD3 was produced in the same manner as in Example D2, except that polymer compound P8 was used instead of polymer compound P4 in Example D2.
By applying a voltage to the light emitting element CD3, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Comparative Example CD4> Production and Evaluation of Light-Emitting Device CD4 A light-emitting device CD4 was produced in the same manner as in Example D2, except that polymer compound P9 was used instead of polymer compound P4 in Example D2.
By applying a voltage to the light emitting element CD4, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Comparative Example CD5> Production and Evaluation of Light-Emitting Device CD5 A light-emitting device CD5 was produced in the same manner as in Example D2, except that polymer compound P10 was used instead of polymer compound P4 in Example D2.
By applying a voltage to the light emitting element CD5, EL light emission having the maximum peak wavelength of the emission spectrum at 520 nm was observed. It was driven at a constant current with an initial luminance of 8000 cd/m ² and LT80 was measured. Table 3 shows the results.

<Example D6> Production and Evaluation of Light Emitting Device D6 Comparative Example CD2 was carried out except that the heating temperature of the hole injection layer in Comparative Example CD2 was set to 250°C and the polymer compound P11 was used instead of the polymer compound IP1. A light-emitting device D6 was fabricated in the same manner as above.
By applying a voltage to the light emitting element D6, EL light emission having the maximum peak wavelength of the emission spectrum at 460 nm was observed. It was driven at a constant current with an initial luminance of 1000 cd/m ² and LT80 was measured. Table 4 shows the results.

<Comparative Example CD6> Evaluation of Light-Emitting Element CD2 The light-emitting element CD2 manufactured in Comparative Example CD2 was driven at a constant current with an initial luminance of 1000 cd/m ² , and LT80 was measured. Table 4 shows the results.

According to the present invention, it is possible to provide a polymer compound useful for manufacturing a light-emitting device with excellent luminance life, a composition containing the polymer compound, and a light-emitting device.

Claims

a first structural unit represented by formula (0);
a second structural unit that is a structural unit other than the first structural unit;
Polymer compounds, including

[In the formula,
a and b each independently represents an integer of 0 to 3;
R 1 and R 2 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom; The group may have a substituent. When multiple R 1 and R 2 are present, they may be the same or different.
R 0 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups are substituents may have A plurality of R 0 may be the same or different.
However, at least one of R 0 represents a group represented by formula (D—C). ]

[In the formula,
mDA1 represents an integer of 2 or more and 10 or less.
Ar DA1 represents an optionally substituted arylene group. A plurality of Ar DA1 may be the same or different.
TDA represents an aryl group optionally having a substituent. ]
2. The polymer compound according to claim 1, wherein the first structural unit is a structural unit represented by formula (0-1).

[wherein, a, b, R 1 , R 2 and R 0 have the same meanings as defined above. ]
3. The polymer compound according to claim 1, wherein said Ar DA1 is a phenylene group which may have a substituent.
The polymer compound according to any one of claims 1 to 3, wherein said TDA is a phenyl group which may have a substituent.
5. The polymer compound according to any one of claims 1 to 4, wherein the first structural unit is a structural unit represented by formula (1).

[In the formula,
a, b, R1 and R2 have the same meanings as above.
n represents 1 or 2;
c and d each independently represent an integer of 0 to 4; e represents an integer of 0 to 5; When there are multiple c, d and e, they may be the same or different.
RA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups are substituents may have
R 3 , R 4 and R 5 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom; , these groups may have a substituent. When multiple R 3 , R 4 and R 5 are present, they may be the same or different. ]
The polymer compound according to claim 5, wherein said n is 2.
The polymer compound according to any one of claims 1 to 6, wherein the first structural unit is a structural unit represented by formula (5).

[In the formula, e and R 5 have the same meanings as described above. ]
The polymer compound according to any one of claims 1 to 7, wherein the second structural unit comprises a structural unit represented by formula (Y).

[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. However, the structural unit represented by the formula (Y) is different from the structural unit represented by the formula (0). ]
The structural unit represented by the formula (Y) is a structural unit represented by the formula (Y-1), a structural unit represented by the formula (Y-2), and a structure represented by the formula (Y-3). unit, a structural unit represented by formula (Y-4), a structural unit represented by formula (Y-5), a structural unit represented by formula (Y-6), a structural unit represented by formula (Y-7) at least selected from the group consisting of a structural unit represented by the formula (Y-8), a structural unit represented by the formula (Y-9) and a structural unit represented by the formula (Y-10) 9. The polymeric compound according to claim 8, comprising one kind of constitutional unit.

[In the formula, R Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent . A plurality of R Y1 may be the same or different, and adjacent R Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[In the formula,
RY1 has the same meaning as above.
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 -. RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of RY2 may be the same or different, and the RY2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[In the formula, RY1 and XY1 have the same meanings as described above. ]

[In the formula,
RY1 has the same meaning as above.
RY3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[In the formula,
RY1 has the same meaning as above.
RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]
The polymer compound according to any one of claims 1 to 9, wherein the second structural unit comprises a structural unit represented by formula (X).

[In the formula,
a 1 and a 2 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.
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 multiple Ar X2 and 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 multiple R X2 and R X3 are present, they may be the same or different. ]
The polymer compound according to any one of claims 1 to 10, wherein the second structural unit comprises a structural unit having a cross-linking group.
12. The polymer compound according to claim 11, wherein the cross-linking group is a cross-linking group selected from X group of cross-linking groups.
(Crosslinking group X 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 ]
13. The polymer compound according to claim 12, wherein the structural unit having the crosslinkable group is a structural unit represented by formula (2) or a structural unit represented by formula (2').

[In the formula,
nA represents an integer of 0 to 5, n represents 1 or 2;
Ar 3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and these groups have a substituent; good too. R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L A are present, they may be the same or different.
X represents a cross-linking group selected from X group of cross-linking groups. When there are multiple X's, they may be the same or different. ]

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. When multiple mA are present, they may be the same or different.
Ar 5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent may be
Ar 4 and Ar 6 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
each of Ar 4 , Ar 5 and Ar 6 is bonded directly or through an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring; may be
K A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and these groups have a substituent; good too. R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple K A are present, they may be the same or different.
X' represents a bridging group selected from the bridging group X group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. However, at least one X' is a cross-linking group selected from the X group of cross-linking groups. ]
Selected from the group consisting of the polymer compound according to any one of claims 1 to 13 and 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 and at least one.
Containing at least one selected from the group consisting of the polymer compound according to any one of claims 1 to 13 and the crosslinked product of the polymer compound according to any one of claims 11 to 13 light-emitting element.