WO2023181952A1

WO2023181952A1 - Compound, polymer compound, composition, and light emitting device

Info

Publication number: WO2023181952A1
Application number: PCT/JP2023/008896
Authority: WO
Inventors: 謙吉岡; 孝和斎藤; 昌光石飛; 晃徳板東; 理彦西田
Original assignee: 住友化学株式会社
Priority date: 2022-03-22
Filing date: 2023-03-08
Publication date: 2023-09-28
Also published as: JP2023140306A

Abstract

This compound is represented by formula (1). [In the formula, Ar1 represents an aromatic hydrocarbon ring or an aromatic heterocycle. Ring Ar2 and ring Ar3 each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle. However, at least one of ring Ar2 and ring Ar3 fuses at at least the position of * with a ring skeleton represented by formula (2).] [In the formula, Ar4 represents an aromatic hydrocarbon ring or an aromatic heterocycle. L1 represents -N(R1L)-, -S-, -O-, or -C(R2L)2-.]

Description

Compounds, polymer compounds, compositions, and light emitting devices

The present invention relates to compounds, polymer compounds, compositions, and light emitting devices.

For example, a compound derived from an arylamine represented by the following formula has been studied as a light-emitting material for use in a light-emitting element (Non-Patent Document 1)

It is desired to develop a light-emitting material with a narrow emission spectrum as a light-emitting material for use in a light-emitting element. However, the spectral width of the emission spectrum of the compound derived from the above-mentioned arylamine is not necessarily sufficiently narrow.

Therefore, the main object of the present invention is to provide a compound that has a narrow emission spectrum and is useful as a light-emitting material for a light-emitting device. Another object of the present invention is to provide a composition containing the compound and a light emitting device containing the compound.

The present invention provides the following [1] to [7].
[1]
A compound represented by formula (1).

[In the formula,
Ar ¹ represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded.
Ring Ar ² and ring Ar ³ each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded. However, at least one of ring Ar ² and ring Ar ³ is condensed with the ring skeleton represented by formula (2) at least at the * position. When a plurality of ring skeletons represented by formula (2) exist, they may be the same or different.
R ¹ represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a hydroxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent. A plurality of R ^1s may be the same or different, and R ^1s may be bonded to each other to form a ring together with the carbon atom to which R ¹ is bonded.
L represents a direct bond, -O-, -S-, -C(R ¹¹ ) ₂ -, -N(R ¹² )-, an arylene group, or a divalent heterocyclic group.
R ¹¹ represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a hydroxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent. A plurality of R ^11s may be the same or different, and R ^11s may be bonded to each other to form a ring together with the carbon atom to which R ¹¹ is bonded.
R ¹² 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. ]

[In the formula,
Ring Ar ⁴ represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded.
L ¹ represents -N(R ^1L )-, -S-, -O- or -C(R ^2L ) ₂ -.
R ^1L 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.
^R2L represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R ^2Ls may be the same or different, and the R ^2Ls may be bonded to each other to form a ring together with the carbon atom to which R ^2L is bonded.
When the ring skeleton represented by formula (2) is fused with ring Ar ² , R ^1L , R ^2L , a substituent that R ^1L may have and a substituent that R ^2L may have may be bonded to ring Ar ² , ring Ar ⁴ , a substituent that ring Ar ² may have, or a substituent that ring Ar ⁴ may have to form a ring.
When the ring skeleton represented by formula (2) is fused with ring Ar ³ , R ^1L , R ^2L , a substituent that R ^1L may have and a substituent that R ^2L may have may be bonded to ring Ar ³ , ring Ar ⁴ , a substituent that ring Ar ³ may have, or a substituent that ring Ar ⁴ may have to form a ring. ]
[2]
The compound according to [1], which is a compound represented by formula (1-A).

[In the formula,
Ring Ar ² , ring Ar ³ and R ¹ have the same meanings as above.
Ring Ar ^1A represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded. ]
[3]
The compound according to [1] or [2], which is a compound represented by formula (1-B).

[In the formula,
R ¹ has the same meaning as above.
X represents a carbon atom or a nitrogen atom, and when X is a carbon atom, X is bonded to -R ^1X or together with adjacent X formula (1-B1):

Either it combines with the ring skeleton represented by formula (2) to form a ring, or it combines with the ring skeleton represented by formula (2) together with adjacent X to form a ring.
R ^1X represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. When a plurality of R ^1Xs exist, they may be the same or different, and the R ^1Xs may be bonded to each other to form a ring together with the carbon atom to which R ^1X is bonded. When X adjacent to X to which R ^1X is bonded is bonded to the ring skeleton represented by formula (2), R ^1X is R 1L , ^R ^2L in the ring skeleton represented by formula (2). , may be combined with a substituent that R ^1L may have or a substituent that R ^2L may have to form a ring.
X in formula (1-B1) has the same meaning as above, and may be bonded to -R ^1X , or may be bonded to the ring skeleton represented by formula (1-B1) together with adjacent X to further form a ring. may be formed, or may be combined with the ring skeleton represented by formula (2) together with adjacent X to further form a ring.
A plurality of X's may be the same or different.
Y represents a carbon atom or a nitrogen atom, and when Y is a carbon atom, Y is bonded to -R ^1Y or together with adjacent Y, formula (1-B2):

Either it combines with the ring skeleton represented by formula (2) to form a ring, or it combines with the ring skeleton represented by formula (2) together with adjacent Y to form a ring.
R ^1Y represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. When a plurality of R ^1Ys exist, they may be the same or different, and the R ^1Ys may be bonded to each other to form a ring together with the carbon atom to which R ^1Y is bonded. When Y adjacent to Y to which R ^1Y is bonded is bonded to the ring skeleton represented by formula (2), R ^1Y is R 1L , ^R ^2L in the ring skeleton represented by formula (2). , may be combined with a substituent that R ^1L may have or a substituent that R ^2L may have to form a ring.
Y in formula (1-B2) has the same meaning as above, and may be bonded to -R ^1Y , or may be bonded to the ring skeleton represented by formula (1-B2) together with adjacent Y to further form a ring. may be formed, or may be bonded to the ring skeleton represented by formula (2) together with adjacent Y to further form a ring.
A plurality of Y's may be the same or different. However, among the combinations of adjacent Y's, at least one pair is bonded to the ring skeleton represented by formula (2) to form a ring. ]
[4]
The compound according to any one of [1] to [3], wherein the ring skeleton represented by formula (2) is a ring skeleton represented by formula (2-A).

[In the formula,
L ^1A represents -N(R ^1AL )-, -S-, -O- or -C(R ^2AL ) ₂ -.
R ^1AL 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 ^2AL represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R ^2ALs may be the same or different, and R ^2ALs may be bonded to each other to form a ring with the carbon atom to which R ^2AL is bonded.
Z represents a carbon atom or a nitrogen atom, and when Z is a carbon atom, Z is bonded to -R ^1Z or together with adjacent Z, formula (2-A1):

Either it combines with the ring skeleton represented by to form a ring.
R ^1Z represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group; It may have. When a plurality of R ^1Ys exist, they may be the same or different, and the R ^1Ys may be bonded to each other to form a ring together with the carbon atom to which R ^1Y is bonded.
Z in formula (2-A1) has the same meaning as above, and may be bonded to -R ^1Z , or may be bonded to the ring skeleton represented by formula (2-A1) together with adjacent Z to further form a ring. may be formed.
A plurality of Z's may be the same or different.
When the ring skeleton represented by formula (2-A) is fused with ring Ar ² , R ^1AL , R ^2AL , a substituent that R ^1AL may have and R ^2AL may have The substituent is bonded to a group on Z located next to two atoms of L ^1A or a group on an atom constituting ring Ar ² located next to two atoms of L ^1A to form a ring. Good too.
When the ring skeleton represented by formula (2-A) is fused with ring Ar ³ , R ^1AL , R ^2AL , a substituent that R ^1AL may have and R ^2AL may have The substituent is bonded to a group on Z located next to two atoms of L ^1A or a group on an atom constituting ring Ar ³ located next to two atoms of L ^1A to form a ring. Good too. ]
[5]
Formulas (3-A), (3-B), (3-C), (3-D), (3-E), (3-F), (3-G), (3-H), ( The compound according to any one of [1] to [4], which is a compound represented by 3-I) or (3-J).

[In the formula,
W represents a carbon atom or a nitrogen atom, and when W is a carbon atom, W is bonded to -R ^1W , or together with adjacent W, formula (3-1):

Either it combines with the ring skeleton represented by to form a ring.
R ^1W represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. When a plurality of R ^1Xs exist, they may be the same or different, and the R ^1Xs may be bonded to each other to form a ring together with the carbon atom to which R ^1X is bonded.
^R3A represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R ^3As may be the same or different, and the R ^3As may be bonded to each other to form a ring together with the carbon atom to which R ^3A is bonded.
W in formula (3-1) has the same meaning as above, and may be bonded to -R ^1W , or may be bonded to the ring skeleton represented by formula (3-1) together with adjacent W to further form a ring. may be formed.
L ^3A represents -N(R ^31L )-, -S-, -O- or -C(R ^32L ) ₂ -.
R ^31L 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.
^R32L represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R ^32Ls may be the same or different, and the R ^32Ls may be bonded to each other to form a ring together with the carbon atom to which R ^32L is bonded.
A substituent that R ^31L , R ^32L , R ^31L may have or a substituent that R ^32L may have is bonded to a group on W ^3A located two atoms adjacent to L ^3A to form a ring. You may do so. ]
[6]
A polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the compound according to any one of [1] to [5].
[7]
The compound according to any one of [1] to [5] or the polymer compound according to [6],
A composition containing at least one member selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a luminescent material, an antioxidant, and a solvent.
[8]
comprising an anode, a cathode, and an organic layer provided between the anode and the cathode,
A light emitting device, wherein the organic layer contains the compound according to any one of [1] to [5] or the polymer compound according to [6].

According to the present invention, it is possible to provide a compound that has a narrow emission spectrum and is useful as a light-emitting material for a light-emitting device. Further, according to the present invention, a composition containing the compound and a light emitting device containing the compound can be provided.

Hereinafter, preferred embodiments of the present invention will be described in detail.

<Explanation of common terms>
Terms commonly used herein have the following meanings unless otherwise specified.

"Room temperature" means 25°C.
Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, i-Pr represents an isopropyl group, and t-Bu represents a tert-butyl group.
The hydrogen atom may be a deuterium atom or a light hydrogen atom.
In the formula representing a metal complex, a solid line representing a bond with the central metal means a covalent bond or a coordinate bond.

"Low molecular compound" means a compound that has no molecular weight distribution and has a molecular weight of 1×10 ⁴ or less.
The term “polymer compound” refers to a polymer having a molecular weight distribution and a number average molecular weight of 1×10 ³ or more (for example, 1×10 ³ to 1×10 ⁸ ) in terms of polystyrene.
"Structural unit" means one or more units present in a polymer compound. Two or more structural units contained in a polymer compound are generally also called "repeat units."
The polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may have other forms.
The terminal group of the polymer compound is preferably a stable group, since if the polymerization active group remains as it is, the luminescence characteristics may deteriorate when the polymer compound is used for producing a light emitting device. The terminal group of the polymer compound is preferably a group that is conjugated to the main chain, such as an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond. can be mentioned.

The "alkyl group" may be either straight chain or branched. The number of carbon atoms in the straight chain alkyl group, not including the number of carbon atoms in the substituents, may be, for example, 1 or more, 2 or more, 3 or more, or 4 or more, and 50 or less, 40 or less, 30 or less, or 20 or less. It may be the following. The number of carbon atoms in the branched alkyl group may be, for example, 3 or more or 4 or more, and 50 or less, 40 or less, 30 or less, or 20 or less, not including the number of carbon atoms of the substituents.
The alkyl group may have a substituent. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group, and heptyl group. octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group and dodecyl group. In addition, an alkyl group is a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent (for example, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.) (for example, 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" may be, for example, 3 or more or 4 or more, and 50 or less, 40 or less, 30 or less, or 20 or less, not including the number of carbon atoms of the substituents.
The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group and a group in which some or all of the hydrogen atoms in the group are substituted with a substituent.

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

The number of carbon atoms in the "cycloalkenyl group" may be, for example, 3 or more or 4 or more, and 30 or less or 20 or less, not including the number of carbon atoms of the substituents.
The cycloalkenyl group may have a substituent. Examples of the cycloalkenyl group include a 5-cyclohexenyl group and a group in which some or all of the hydrogen atoms in these groups are substituted with a substituent.

The "alkynyl group" may be either straight chain or branched. The number of carbon atoms in the straight chain alkynyl group may be, for example, 2 or more or 3 or more, and 30 or less or 20 or less, not including carbon atoms of substituents. The number of carbon atoms in the branched alkynyl group may be, for example, 4 or more, 30 or less, or 20 or less, not including carbon atoms of substituents.
The alkynyl group may have a substituent. Examples of the alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents.

The number of carbon atoms in the "cycloalkynyl group" may be, for example, 4 or more, 30 or less, or 20 or less, not including carbon atoms of substituents.
The cycloalkynyl group may have a substituent. Examples of the cycloalkynyl group include a 5-cyclohexynyl group and groups in which some or all of the hydrogen atoms in these groups are substituted with substituents.

The "alkoxy group" may be either linear or branched. The number of carbon atoms in the straight chain alkoxy group, not including the number of carbon atoms in the substituents, may be, for example, 1 or more, 2 or more, 3 or more, or 4 or more, and 40 or less, 30 or less, 20 or less, or 10 or less. It may be the following. The number of carbon atoms in the branched alkoxy group may be, for example, 3 or more or 4 or more, and 40 or less, 30 or less, 20 or less, or 10 or less, not including the number of carbon atoms of the substituents.
The alkoxy group may have a substituent. Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, - Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and some or all of the hydrogen atoms in these groups are substituents (for example, cycloalkyl group, alkoxy group, Examples include groups substituted with cycloalkoxy groups, aryl groups, fluorine atoms, etc.).

The number of carbon atoms in the "cycloalkoxy group" may be, for example, 3 or more or 4 or more, 40 or less, 30 or less, 20 or less, or 10 or less, not including the number of carbon atoms of the substituents.
The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group and a group in which some or all of the hydrogen atoms in the group are substituted with a substituent.

The number of carbon atoms in the "aryloxy group" may be, for example, 6 or more, 60 or less, or 48 or less, not including the number of carbon atoms in the substituents.
The aryloxy group may have a substituent. Examples of the aryloxy group include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1-pyrenyloxy group, and Examples include groups in which part or all of the hydrogen atoms are substituted with a substituent (eg, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, etc.).

"Aromatic hydrocarbon group" means a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom 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 constituting a ring from an aromatic hydrocarbon is also referred to as an "arylene group."
The number of carbon atoms of the aromatic hydrocarbon group may be, for example, 6 or more, 60 or less, 40 or less, 20 or less, or 10 or less, not including the number of carbon atoms of the substituents.
Examples of the "aromatic hydrocarbon group" include monocyclic aromatic hydrocarbons (for example, benzene), or polycyclic aromatic hydrocarbons (for example, naphthalene, indene, naphthoquinone, indenone). and bicyclic aromatic hydrocarbons such as tetralone; tricyclic aromatic hydrocarbons such as anthracene, phenanthrene, dihydrophenanthrene, fluorene, anthraquinone, phenantoquinone, and fluorenone; benzanthracene, benzophenanthrene, benzofluorene, pyrene and 4-ring aromatic hydrocarbons such as fluoranthene; 5-ring aromatic hydrocarbons such as dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, perylene and benzofluoranthene; 6-rings such as spirobifluorene and heptocyclic aromatic hydrocarbons such as benzospirobifluorene and acenaphthofluoranthene. Groups other than the above may be mentioned. The aromatic hydrocarbon group includes a group in which a plurality of these groups are bonded. The aromatic hydrocarbon group may have a substituent.

"Aromatic hydrocarbon ring" means a ring possessed by an aromatic hydrocarbon. The aromatic hydrocarbon ring may be a monocyclic ring or a condensed polycyclic ring. Examples of the aromatic hydrocarbon ring include a ring possessed by the above-mentioned monocyclic aromatic hydrocarbon, a ring possessed by a polycyclic aromatic hydrocarbon, and the like. The aromatic hydrocarbon ring includes a ring in which a plurality of these rings are bonded or condensed. The aromatic hydrocarbon ring may have a substituent.

Examples of the aryl group include 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 include groups substituted with alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, fluorine atoms, etc.).

Examples of the arylene group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a dihydrophenanthrenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylene diyl group, a chrysenediyl group, and Examples include groups in which some or all of the hydrogen atoms are substituted with substituents. The arylene group includes a group in which a plurality of these groups are bonded. The arylene group is preferably a group represented by formula (A-1) to formula (A-20).

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

The term "heterocyclic group" refers to a group obtained by removing one or more hydrogen atoms directly bonded to an atom (carbon atom or heteroatom) 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 preferable. A group obtained by removing p hydrogen atoms (p represents an integer of 1 or more) directly bonded to the atoms constituting the 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 the atoms constituting the 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, and dibenzophosphole. Compounds in which the heterocycle itself shows aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilole, benzopyran, etc., even if the heterocycle itself does not show aromaticity, an aromatic ring is fused to the heterocycle. Examples include compounds that have been
The number of carbon atoms in the heterocyclic group may be, for example, 1 or more, 2 or more, or 3 or more, and 60 or less, 40 or less, or 20 or less, not including the number of carbon atoms of the substituents. The number of heteroatoms in the heterocyclic group, not including the number of heteroatoms in substituents, is usually 1 to 30, preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3. It is.
Examples of the heterocyclic group include monocyclic heterocyclic compounds (for example, 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, dibenzoborole, dibenzosilole, dibenzophosphole, dibenzoselenophene, carbazole, azacarbazole , diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, acridone, fenazaborin, phenophosphazine, 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, azaindrocarbazole, diazaindrocarbazole, azaindenocarbazole and diazaindenocarbazole; carbazolocarbazole, benzindrocarbazole and benzoindenocarbazole 6-ring heterocyclic compounds such as; and 7-ring heterocyclic compounds such as dibenzoindolocarbazole and dibenzoindenocarbazole. Examples include groups in which one or more groups are removed. The heterocyclic group includes a group in which a plurality of these groups are bonded. The heterocyclic group may have a substituent (for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).

"Aromatic heterocycle" means a ring possessed by an aromatic heterocyclic compound. The aromatic heterocyclic compound may be monocyclic or fused polycyclic. Examples of the aromatic heterocycle include the ring possessed by the above-mentioned "aromatic heterocyclic compound". Further, the aromatic heterocycle includes a ring in which a plurality of these rings are bonded or condensed, and a ring in which an aromatic hydrocarbon ring is bonded or condensed to these rings. The aromatic heterocycle may have a substituent.

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

The number of carbon atoms in the divalent heterocyclic group, not including the number of carbon atoms in the substituents, may be, for example, 2 or more, 3 or more, or 4 or more, and 60 or less, 40 or less, 20 or less, or 15 or less. It's good.
Examples of the divalent heterocyclic group include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, Examples include divalent groups obtained by removing two hydrogen atoms from among the hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring from diazole or triazole. The divalent heterocyclic group includes a group in which a plurality 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 R ^a represent the same meanings as above. ]

"Halogen atom" refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

The "amino group" may have a substituent, and a substituted amino group (ie, a secondary amino group or a tertiary amino group, more preferably a tertiary amino group) is preferable. The substituent that the amino group has is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. When the amino group has a plurality of substituents, they may be the same or different, or may be bonded to each other to form a ring with the nitrogen atom to which they are bonded.
Examples of substituted amino groups include dialkylamino groups, dicycloalkylamino groups, diarylamino groups, and those in which some or all of the hydrogen atoms in these groups are substituents (e.g., alkyl groups, cycloalkyl groups, alkoxy groups). , cycloalkoxy group, aryl group, 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 include groups in which some or all of the atoms are substituted with a substituent (eg, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc.).

A "crosslinking group" is a group that can generate a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared ray irradiation, radical reaction, etc. Examples of the crosslinking group include crosslinking groups selected from crosslinking group A (ie, crosslinking groups represented by formulas (XL-1) to (XL-19)).
(Bridging group A group)

[In the formula, R ^XL represents a methylene group, an oxygen atom, or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL 's exist, they may be the same or different. When a plurality of n ^XLs exist, they may be the same or different. *1 represents the bonding position. These bridging groups may have a substituent, and when a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded. It's okay. ]

Examples of the "substituent" include 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, Examples include alkenyl groups, cycloalkenyl groups, alkynyl groups, and cycloalkynyl groups. The substituent may be a bridging group.

"Dendron" means a group having a regular dendritic branching structure (i.e., dendrimer structure) with an atom or ring as a branching point. Examples of compounds having dendrons (hereinafter referred to as "dendrimers") include WO 2002/067343, JP 2003-231692, WO 2003/079736, and WO 2006/097717. Examples include structures described in the literatures such as .

Examples of dendrons include groups represented by formulas (DA) to (DC).

[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. A plurality of ^TDAs may be the same or different. ]

[In the formula,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 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. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and even if these groups have a substituent, good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
^TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^TDAs may be the same or different. ]

[In the formula,
m ^DA1 represents an integer greater than or equal to 0.
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of Ar ^DA1s exist, they may be the same or different.
^TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually integers of 10 or less, preferably 5 or less, and more preferably 0 or 1. It is preferable that m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are the same integer.

G ^DA is preferably an aromatic hydrocarbon group or a heterocyclic group, more preferably hydrogen directly bonded to a carbon atom or nitrogen atom constituting a ring from a benzene ring, pyridine ring, pyrimidine ring, triazine ring, or carbazole ring. A group consisting of three atoms removed, and these groups may have a substituent.
The substituent that ^GDA may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably an alkyl group, A cycloalkyl group, an alkoxy group, or a cycloalkoxy group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

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

[In the formula,
* represents a bond with Ar ^DA1 in formula (DA), Ar ^DA1 in formula (DB), Ar ^DA2 in formula (DB), or Ar ^DA3 in formula (DB).
** represents a bond with Ar ^DA2 in formula (DA), Ar ^DA2 in formula (DB), Ar ^DA4 in formula (DB), or Ar ^DA6 in formula (DB) .
*** represents a bond with Ar ^DA3 in formula (DA), Ar ^DA3 in formula (DB), Ar ^DA5 in formula (DB), or Ar ^DA7 in formula (DB). represent.
R ^DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. 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 a substituent. It's okay.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably groups represented by formulas (ArDA-1) to (ArDA-6). Note that * represents the bonding position.

[In the formula,
^RDA represents the same meaning as above.
R ^DB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple ^RDBs , they may be the same or different. ]

R ^DB is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and even more preferably an aryl group.

Examples and preferred ranges of substituents that Ar ^DA1 to Ar ^DA7 , R ^DA and R ^DB may have are the same as the examples and preferred ranges of substituents that G ^DA may have.

T ^DA is preferably a group represented by formulas (TDA-1) to (TDA-4). Note that * represents the bonding position.

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

The group represented by formula (DA) is preferably a group represented by formulas (DA1) to (DA5). Note that * represents the bonding position.

[In the formula,
R ^p1 , R ^p2 , R ^p3 and R ^p4 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 , R ^p2 and R ^p4 , they may be the same or different.
np1 represents an integer from 0 to 5, np2 represents an integer from 0 to 3, np3 represents 0 or 1, and np4 represents an integer from 0 to 4. A plurality of np1s may be the same or different. ]

The group represented by formula (D-B) is preferably a group represented by formulas (D-B1) to (D-B3). Note that * represents the bonding position.

[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 from 0 to 5, np2 represents an integer from 0 to 3, and np3 represents 0 or 1. When there are a plurality of np1 and np2, they may be the same or different. ]

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

R ^p1 , R ^p2 and R ^p3 are preferably an alkyl group or a cycloalkyl group.

The group represented by formula (DC) is preferably a group represented by formula (D-C1) to formula (D-C4). Note that * represents the bonding position.

[In the formula,
R ^p4 to R ^p6 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. When there is a plurality of R ^p4 to R ^p6 , they may be the same or different.
np4 represents an integer from 0 to 4, np5 represents an integer from 0 to 5, and np6 represents an integer from 0 to 5. ]

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

R ^p4 to R ^p6 are preferably an alkyl group or a cycloalkyl group, more preferably a methyl group, ethyl group, isopropyl group, tert-butyl group, hexyl group, 2-ethylhexyl group, cyclohexyl group or tert-octyl group. and more preferably a methyl group, ethyl group, isopropyl group, tert-butyl group, hexyl group, 2-ethylhexyl group or tert-octyl group.

<Compound>
The compound of this embodiment is a compound represented by formula (1). The compound of this embodiment may be a low molecular compound.

Ar ¹ is preferably an aromatic hydrocarbon ring, more preferably a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a chrysene ring, or a perylene ring, and even more preferably a benzene ring or a naphthalene ring.

Ring Ar ² and ring Ar ³ are preferably aromatic hydrocarbon rings, more preferably benzene ring, naphthalene ring, anthracene ring, pyrene ring, chrysene ring, or perylene ring, still more preferably benzene ring or naphthalene ring. It is.

R ¹ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a hydroxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and more preferably hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group, a cycloalkyl group, or an aryl group. It is the basis.

The aryl group in R ¹ is preferably a phenyl group, a naphthyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, or a spirobifluorenyl group, even if these groups have a substituent. good.

The monovalent heterocyclic group in R ¹ is a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a phenoxazinyl group. or a phenothiazinyl group, and these groups may have a substituent.

In the substituted amino group for R ¹ , the substituent that the amino group has is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may further have a substituent. Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent of the amino group are the same as the examples and preferred ranges of the aryl group and monovalent heterocyclic group in R ¹ .

L is preferably a direct bond, -O-, -S-, an arylene group or a divalent heterocyclic group, more preferably a direct bond, -O- or -S-, still more preferably a direct bond. be. In addition, L is directly bonded means that Ar ¹ and ring Ar ² are directly bonded.

The examples and preferred ranges of R ¹¹ are the same as the examples and preferred ranges of R ^2L described below. Examples and preferred ranges of R ¹² are the same as those of R ^1L described below.

The substituent that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have is preferably a group represented by the following formula (1-T).

[In the formula, R ^1T represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom; It may have a group. ]

The substituent that R ^1T 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. and more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and even more preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups are It may further have a substituent.

The substituents that R ^1T may further include are preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent group. A heterocyclic group, a substituted amino group, or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and still more preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent.

The aryl group in the substituent of R ^1T or R ^1T is preferably a phenyl group, a naphthyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group, or a spirobifluorenyl group, and these groups are It may have.

The monovalent heterocyclic group in R ^1T or the substituent of R ^1T is a pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, azacarbazolyl group, diazacarba A zolyl group, a phenoxazinyl group or a phenothiazinyl group is preferable, and these groups may have a substituent.

In the substituted amino group in R ^1T or the substituent of R ^1T , the substituent that the amino group has is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. You may do so. Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituent of the amino group are the same as the examples and preferred ranges of the aryl group and monovalent heterocyclic group in R ^1T .

R ^1T is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group, and more preferably an alkyl group, a cycloalkyl group, or one of formulas (DA) to ( A group represented by DC) or a substituted amino group, and these groups may have a substituent.

Ring Ar ⁴ is preferably an aromatic hydrocarbon ring, more preferably a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a chrysene ring, or a perylene ring, and even more preferably a benzene ring or a naphthalene ring.

The preferred range of the substituent that ring Ar ⁴ may have is the same as the preferred range of the substituent that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above.

L ¹ is preferably a group represented by -N(R ^1L )-.

R ^1L is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group.

R ^2L is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group.

The preferable range of the substituents that R ^1L and R ^2L may have is the same as the above-mentioned preferable range of the substituents that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have. be.

When the ring skeleton represented by formula (2) is fused with ring Ar ² , a substituent that R ^1L , R ^2L , R ^1L may have or a substituent that R ^2L may have is preferably bonded to ring Ar ² , ring Ar ⁴ , a substituent that ring Ar ² may have, or a substituent that ring Ar ⁴ may have to form a ring.

When the ring skeleton represented by formula (2) is fused with ring Ar ³ , a substituent that R ^1L , R ^2L , R ^1L may have or a substituent that R ^2L may have is preferably bonded to ring Ar ³ , ring Ar ⁴ , a substituent that ring Ar ³ may have, or a substituent that ring Ar ⁴ may have to form a ring.

The compound represented by formula (1) is preferably a compound represented by formula (1-A).

Ar ^1A is preferably an aromatic hydrocarbon ring, more preferably a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a chrysene ring, or a perylene ring, and even more preferably a benzene ring or a naphthalene ring.

The preferred range of the substituent that Ar ^1A may have is the same as the preferred range of the substituent that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above.

The compound represented by formula (1) is more preferably a compound represented by formula (1-B).

It is preferable that X is a carbon atom.

When X is a carbon atom, X is bonded to -R ^1X , or is bonded to the ring skeleton represented by formula (1-B1) with X of the adjacent carbon atom to form a ring, It is preferable that it is either.

The preferred range of R ^1X is the same as the preferred range of the substituents that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above.

It is preferable that Y is a carbon atom.

When Y is a carbon atom, Y is bonded to -R ^1Y , or is bonded to the ring skeleton represented by formula (1-B2) together with Y of the adjacent carbon atom to form a ring, It is preferable that it is either bonded to the ring skeleton represented by formula (2) together with Y of the adjacent carbon atom to form a ring.

The preferred range of R ^1Y is the same as the preferred range of the substituents that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above.

In the compound represented by formula (1-B), when the ring skeleton represented by formula (2) is bonded to two adjacent Xs, R ^1L , R ^2L , R ^1L in formula (2) The substituent that may have or the substituent that R ^2L may have is a group (R 1X ) on X located next to two atoms of L ¹ or a group (R ^1X ) located next to two atoms of L ¹ It is preferable that the ring is bonded to a group on an atom constituting the ring R ⁴ (for example, R ^1Z on Z in formula (2-A)) to form a ring.

In the compound represented by formula (1-B), when the ring skeleton represented by formula (2) is bonded to two adjacent Y, R ^1L , R ^2L , R ^1L in formula (2) The substituent that may have or the substituent that R ^2L may have is a group (R 1Y ) on Y located next to two atoms of L ¹ or a group (R ^1Y ) located next to two atoms of L ¹ It is preferable that the ring is bonded to a group on an atom constituting the ring R ⁴ (for example, R ^1Z on Z in formula (2-A)) to form a ring.

The ring skeleton represented by formula (2) is preferably a ring skeleton represented by formula (2-A).

L ^1A is preferably -N(R ^1AL )-.

R ^1AL is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group.

R ^2AL is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group.

The preferred range of the substituents that R ^1AL and R ^2AL may have is the same as the preferred range of the substituents that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above. be.

When the ring skeleton represented by formula (2-A) is fused with ring Ar ² , R ^1AL , R ^2AL , a substituent that R ^1AL may have or R ^2AL may have The substituent is a group on an atom constituting ring Ar ² located next to two atoms of L ^1A (for example, R ^1Y on Y in formula (1-B)), or a group located next to two atoms of L ^1A . It is preferable that the group (R ^1Z ) on Z be bonded to form a ring.

When the ring skeleton represented by formula (2-A) is fused with ring Ar ³ , R ^1AL , R ^2AL , a substituent that R ^1AL may have or R ^2AL may have The substituent is a group on an atom constituting ring Ar ³ located next to two atoms of L ^1A (for example, R ^1Y on Y in formula (1-B)), or a group located next to two atoms of L ^1A . It is preferable that the group (R ^1Z ) on Z be bonded to form a ring.

It is preferable that Z is a carbon atom.

When Z is a carbon atom, Z is bonded to -R ^1Z , or is bonded to the ring skeleton represented by formula (2-A1) with Z of the adjacent carbon atom to form a ring, It is preferable that it is either.

The preferred range of R ^1Z is the same as the preferred range of the substituents that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above.

The compound represented by formula (1) has formulas (3-A), (3-B), (3-C), (3-D), (3-E), (3-F), (3 -G), (3-H), (3-I) or (3-J) are more preferred.

It is preferable that W is a carbon atom.

When W is a carbon atom, W is bonded to -R ^1W , or is bonded to the ring skeleton represented by formula (3-1) together with W of an adjacent carbon atom to form a ring, and is preferably bonded to -R ^1W .

The preferred range of R ^1W is the same as the preferred range of the substituents that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have, as described above.

^R3A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a hydroxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and more preferably hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and particularly preferably an alkyl group, a cycloalkyl group, or an aryl group. It is the basis.

The preferable range of the substituent that R ^3A may have is the same as the above-mentioned preferable range of the substituent that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have.

L ^3A is preferably -N(R ^31L )-.

R ^31L is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group.

R ^32L is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group.

The preferable range of the substituent that R ^31L may have is the same as the above-mentioned preferable range of the substituent that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have.

The preferable range of the substituent that R ^32L may have is the same as the above-mentioned preferable range of the substituent that Ar ¹ , ring Ar ² , ring Ar ³ , and R ¹ may have.

The substituents that R ^31L , R ^32L , and R ^31L may have and the substituents that R ^32L may have include a group on W ^3A that is a carbon atom located two atoms adjacent to L ^3A (R ^1W ) is preferably bonded to form a ring.

Examples of the compounds of this embodiment include compounds represented by formulas (1-1) to (1-125).

<High molecular compound>
The polymer compound of this embodiment includes a structural unit (hereinafter also referred to as structural unit (A)) having a group obtained by removing one or more hydrogen atoms from the above compound.

The structural unit (A) is preferably a structural unit having a group obtained by removing 1 to 5 hydrogen atoms from the above compound, and more preferably the above compound, since the polymer compound of this embodiment can be easily synthesized. A structural unit having a group obtained by removing one or more and three or less hydrogen atoms from a compound, and more preferably a structural unit having a group obtained by removing one or two hydrogen atoms from the above compound.

The structural unit (A) is preferably a structural unit represented by the formula (AP-1), the formula (AP-2), or the formula (AP-3), since the polymer compound of the present embodiment can be easily synthesized. More preferably, it is a structural unit represented by formula (AP-1) or formula (AP-2), and still more preferably a structural unit represented by formula (AP-2).

[In the formula,
M ^AP1 represents a group obtained by removing one hydrogen atom from the above compound.
^MAP2 represents a group obtained by removing two hydrogen atoms from the above compound.
M ^AP3 represents a group obtained by removing three hydrogen atoms from the above compound.
L ^AP1 each independently represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^AP1 )-, an oxygen atom, or a sulfur atom; It may have a substituent. When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded.
R ^AP1 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 a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded. When a plurality of L ^AP1s exist, they may be the same or different.
n ^AP1 represents an integer from 0 to 10.
Ar ^AP1 represents a hydrocarbon group or a heterocyclic group, and these groups may have a substituent. When a plurality of substituents exist, they may be the same or different, and may be bonded to each other to form a ring with the atoms to which they are bonded. ]

L ^AP1 is preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, more preferably an alkylene group or an arylene group, even more preferably an arylene group, and these groups may have a substituent.
Examples and preferred ranges of the arylene group and divalent heterocyclic group in L ^AP1 are respectively the same as the examples and preferred ranges of the arylene group and divalent heterocyclic group in Ar ^Y1 described below. The alkylene group in L ^AP1 is preferably a methylene group, an ethylene group or a propylene group, more preferably a methylene group, and these groups may have a substituent.

Examples and preferred ranges of R ^AP1 are the same as examples and preferred ranges of R ^X1 to R ^X3 described below.

n ^AP1 is preferably an integer of 0 to 5, preferably an integer of 0 to 3, more preferably 0 or 1, and even more preferably 0.

Examples of the hydrocarbon group in Ar ^AP1 include an aromatic hydrocarbon group that may have a substituent and an aliphatic hydrocarbon group that may have a substituent. The hydrocarbon group in Ar ^AP1 includes a group in which a plurality of these groups are bonded.
In Ar ^AP1 , the aliphatic hydrocarbon group includes a group obtained by removing one hydrogen atom n ^AP from an alkylene group or a cycloalkylene group, preferably a group obtained by removing one hydrogen atom n ^AP from an alkylene group, These groups may have a substituent. Examples and preferred ranges of this alkylene group include the examples and preferred ranges of the alkylene group in L ^H1 described below.
In Ar ^AP1 , examples of the aromatic hydrocarbon group include a group obtained by removing one hydrogen atom n ^AP from an arylene group, and this group may have a substituent. Examples and preferred ranges of this arylene group include the examples and preferred ranges of the arylene group in Ar ^Y1 described below.
Examples of the heterocyclic group in Ar ^AP1 include a group obtained by removing one hydrogen atom n ^AP from a divalent heterocyclic group, and this group may have a substituent. Examples and preferred ranges of this divalent heterocyclic group include the examples and preferred ranges of the divalent heterocyclic group in Ar ^Y1 described below.

Examples and preferred examples of substituents that L ^AP1 and Ar ^AP1 may have are the same as examples and preferred ranges of substituents that the group represented by Ar ^Y1 described below may have.

Examples of the structural unit represented by formula (A) include structural units represented by formulas (1-201) to (1-215).

The polymer compound of this embodiment may contain only one type of structural unit (A), or may contain two or more types.

The total amount of structural units (A) is preferably 0.1 to 50 mol%, more preferably 0.3 to 20 mol%, and further Preferably it is 0.5 to 10 mol%.

The polymer compound of this embodiment may further contain structural units other than the structural unit (A).

It is preferable that the polymer compound of the present embodiment further includes a structural unit represented by the formula (Y) described below (hereinafter also referred to as structural unit (Y)).

Examples and preferred ranges of the structural unit (Y) contained in the polymer compound of this embodiment are the same as examples and preferred ranges of the structural unit (Y) contained in the polymer host described below.

The content of the structural unit (Y) contained in the polymer compound of this embodiment is determined based on the total amount of structural units contained in the polymer compound, since when Ar ^Y1 is an arylene group, the luminance life of the light emitting element is better. On the other hand, it is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%.

The content of the structural unit (Y) contained in the polymer compound of this embodiment is such that Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group. When it is a directly bonded divalent group, the charge transport property of the light emitting device is excellent, so it is preferably 0.5 to 40 mol%, more preferably 0.5 to 40 mol%, based on the total amount of structural units contained in the polymer compound. is 3 to 30 mol%.

The polymer compound of this embodiment may contain only one type of structural unit (Y), or may contain two or more types.

Since the polymer compound of the present embodiment has excellent hole transport properties, it is preferable that the polymer compound further contains a structural unit represented by formula (X) described below (hereinafter also referred to as structural unit (X)).

Examples and preferred ranges of the structural unit (X) contained in the polymer compound of this embodiment are the same as examples and preferred ranges of the structural unit (X) contained in the polymer host described below.

The polymer compound of this embodiment may contain only one type of structural unit (X), or may contain two or more types.

Examples of the polymer compounds of this embodiment include polymer compounds P-1 to P-3 shown in Table 1. Here, formula (1-P) means a structural unit (structural unit (A)) having a group obtained by removing one or more hydrogen atoms from the compound represented by formula (1), and formula (X) means the structural unit represented by formula (X), formula (Y) means the structural unit represented by formula (Y), and "other" means the structural unit represented by formula (1-P) , means a structural unit other than formula (X) and formula (Y).

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

Examples and preferred ranges of the structural units of formula (1-P), formula (Y), and formula (X) in polymer compounds P-1 to P-3 are as described above.

The terminal group of the polymer compound of this embodiment is preferable because if the polymerization active group remains as it is, the luminescence characteristics and brightness life may deteriorate when the polymer compound is used to fabricate a light emitting device. is a stable group. This terminal group is preferably a group that is conjugated to the main chain, such as an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond. .

The polymer compound of this embodiment may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may be of any other form; A copolymer formed by copolymerizing raw material monomers is preferable.

<Method for producing compound>
Next, a method for producing the compound of this embodiment will be explained.

In the method for producing the compound of the present embodiment, functional group conversion reactions of the following formulas (M-1) to (M-11) may be performed as necessary.

The compound of this embodiment can be produced, for example, by a method including step A of reacting a compound represented by formula (M-1) and a compound represented by formula (M-2). .
(Process A)

[In the formula,
Ar ¹ , Ar ² , Ar ³ and L have the same meanings as above.
R ¹ represents the same meaning as above (however, hydrogen atoms are excluded).
M ^M1 represents a lithium atom or Mg-X ^M2 .
X ^M1 represents a monovalent anion obtained by removing one proton (H ⁺ ) from an acid.
X ^M2 represents an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom, and these groups may have a substituent. ]

The acid in X ^M1 may be, for example, alkylsulfonic acid, cycloalkylsulfonic acid, arylsulfonic acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, etc., and these acids may have substituents. good.

Examples of the alkylsulfonic acid include methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, and the like. Examples of the arylsulfonic acid include p-toluenesulfonic acid and the like.

Preferably, M ^M1 is Mg-X ^M2 .

In X ^M2 , examples of the alkylsulfonyloxy group include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group. Examples of the arylsulfonyloxy group include p-toluenesulfonyloxy group.

Preferably, X ^M2 is a chlorine atom, a bromine atom, or an iodine atom.

Step A is usually performed in a solvent. Examples of solvents include alcohol solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, and 2-ethoxyethanol; ether solvents such as diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, and diglyme. ; Halogen solvents such as methylene chloride and chloroform; Nitrile solvents such as acetonitrile and benzonitrile; Hydrocarbon solvents such as hexane, decalin, toluene, xylene, and mesitylene; N,N-dimethylformamide, N,N-dimethylacetamide amide solvents such as acetone, dimethyl sulfoxide, water, etc.

In Step A, the reaction time is usually 30 minutes to 150 hours, and the reaction temperature is usually between the melting point and the boiling point (above the melting point and below the boiling point) of the solvent present in the reaction system.

In step A, the amount of the compound represented by formula (M-2) is usually 1 to 20 mol per 1 mol of the compound represented by formula (M-1).

The compound represented by formula (M-1) can be produced, for example, by a method including step B of reacting a compound represented by formula (M-3).
(Process B)

[In the formula,
Ar ¹ , Ar ² , Ar ³ , L and X ^M1 have the same meanings as above.
R ¹ represents the same meaning as above (however, hydrogen atoms are excluded). ]

The reaction in step B is preferably carried out in the presence of an acid such as alkylsulfonic acid, cycloalkylsulfonic acid, arylsulfonic acid, hydrochloric acid, hydrobromic acid or hydroiodic acid. When an acid is used, the amount thereof is usually 1 to 20 mol per 1 mol of the compound represented by formula (M-3).

Examples of the alkylsulfonic acid used in Step B include methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, and the like. The arylsulfonic acid used in step B includes p-toluenesulfonic acid and the like.

The reaction in step B is usually carried out in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in step B are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in the reaction of step A.

After the reaction in step B, the compound represented by formula (M-1) may be isolated and the reaction in step A may be performed, or the compound represented by formula (M-1) is not isolated and the reaction in step A is performed. The reaction of Step A may be carried out continuously in the reaction solvent of B.

The compound represented by formula (M-3) is produced, for example, by a method including step C in which a compound represented by formula (M-4) and a compound represented by formula (M-5) are reacted. can do.
(Process C)

[In the formula,
Ar ¹ , Ar ² , Ar ³ and L have the same meanings as above.
R ¹ represents the same meaning as above (however, hydrogen atoms are excluded).
M ^M2 represents a lithium atom or Mg-X ^M2 . ]

Preferably, M ^M2 is Mg-X ^M2 . The examples and preferred ranges of X ^M2 in M ^M2 are the same as the examples and preferred ranges of X ^M2 in M ^M1 .

Step C is usually performed in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in Step C are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in Step A.

The compound of this embodiment can also be produced, for example, by a method including step D of reacting a compound represented by formula (M-6) with a compound represented by formula (M-7).
(Process D)

[In the formula,
Ar ¹ , Ar ² , Ar ³ and L have the same meanings as above.
R ¹ represents the same meaning as above (however, hydrogen atoms are excluded).
X ^M3 represents an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom, and these groups may have a substituent. ]

Examples and preferred ranges for X ^M3 are the same as those for X ^M1 .

The reaction in step D is usually carried out in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in step D are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in the reaction of step A.

The compound represented by formula (M-6) can be produced, for example, by a method including step E of reacting the compound represented by formula (M-4).
(Process E)

[Wherein, Ar ¹ , Ar ² , Ar ³ and L have the same meanings as above. ]

The reaction in step E is usually carried out in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in Step E are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in the reaction of Step A.

The compound of this embodiment can also be produced, for example, by a method including step F in which a compound represented by formula (M-3) and a compound represented by formula (M-8) are reacted.
(Process F)

[In the formula,
Ar ¹ , Ar ² , Ar ³ and L have the same meanings as above.
R ¹ represents the same meaning as above (however, hydrogen atoms are excluded). ]

The reaction in step F is preferably carried out in the presence of an acid such as alkylsulfonic acid, cycloalkylsulfonic acid, arylsulfonic acid, hydrochloric acid, hydrobromic acid or hydroiodic acid. When an acid is used, the amount thereof is usually 1 to 20 mol per 1 mol of the compound represented by formula (M-3).

Examples of the alkylsulfonic acid used in Step F include methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, and the like. The arylsulfonic acid used in step F includes p-toluenesulfonic acid and the like.

The reaction in step F is usually carried out in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in Step F are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in the reaction of Step A.

The compound represented by formula (1) can also be produced, for example, by a method including step G of reacting a compound represented by formula (M-10). Furthermore, the compound represented by formula (M-4) and the compound represented by formula (M-6) are also produced by a method including step G of reacting the compound represented by formula (M-10). be able to.
(Process G)

[In the formula,
Ar ¹ , Ar ² , Ar ³ and L have the same meanings as above.
L ^M1 represents -C(=O)- or -C(R ¹ ) ₂ -.
R ¹ represents the same meaning as above.
Z ^M1 represents a group represented by -B(OR ^ZM1 ) ₂ , an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom, and these groups are substituents. You may do so.
R ^ZM1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an amino group, and these groups may have a substituent. A plurality of R ^ZM1s may be the same or different, and may be bonded to each other to form a ring structure together with the oxygen atom to which each is bonded. ]

When L ^M1 is -C(=O)-, the compound represented by formula (M-9) is a compound represented by formula (M-4). When L ^M1 is -C(R ¹ ) ₂ -, the compound represented by formula (M-9) is a compound represented by formula (1). When L ^M1 is -C(R ¹ ) ₂ - and R ¹ is a hydrogen atom, the compound represented by formula (M-9) is a compound represented by formula (M-6) You can also say that.

In Z ^M1 , examples of the alkylsulfonyloxy group include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group. In Z ^M1 , examples of the arylsulfonyloxy group include p-toluenesulfonyloxy group.

Examples of the group represented by -B(OR ^ZM1 ) ₂ include groups represented by the following formulas (ZM-1) to (ZM-10).

Z ^M1 is preferably a trifluoromethanesulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom because the reaction in step G (coupling reaction) proceeds easily.

The reaction in step G is usually carried out in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in step G are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in the reaction of step A.

The compound represented by formula (1) can also be produced, for example, by a method including step H of reacting a compound represented by formula (M-11). Furthermore, the compound represented by formula (M-4) and the compound represented by formula (M-6) are also produced by a method including step H of reacting the compound represented by formula (M-11). be able to.
(Process H)

[In the formula,
Ar ¹ , Ar ² , Ar ³ , L and L ^M1 have the same meanings as above.
Z ^M2 and Z ^M3 represent a group represented by -B(OR ^ZM2 ) ₂ , an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom, and these groups may have a substituent.
R ^ZM2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an amino group, and these groups may have a substituent. A plurality of R ^ZM2s may be the same or different, and may be bonded to each other to form a ring structure together with the oxygen atom to which each is bonded. ]

In Z ^M2 and Z ^M3 , examples of the alkylsulfonyloxy group include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group. In Z ^M2 and Z ^M3 , examples of the arylsulfonyloxy group include p-toluenesulfonyloxy group.

Examples of the group represented by -B(OR ^ZM2 ) ₂ include groups represented by formulas (ZM-1) to (ZM-10).

The reaction in step H is usually carried out in a solvent. Examples and preferred ranges of the solvent, reaction time, and reaction temperature in Step H are the same as the examples and preferred ranges of the solvent, reaction time, and reaction temperature in the reaction of Step A.

- Common explanation of steps G and H In the coupling reaction (reaction in steps G and H), a catalyst such as a palladium catalyst may be used to promote the reaction. Palladium catalysts include palladium acetate, bis(triphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II). , tris(dibenzylideneacetone) dipalladium(0), and the like.

Palladium catalysts may be used in combination with phosphorus compounds such as triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, and 1,1′-bis(diphenylphosphino)ferrocene. .

When a palladium catalyst is used in the coupling reaction, the amount is usually an effective amount, for example, per 1 mole of the compound represented by formula (M-10) or formula (M-11), and preferably, It is 0.00001 to 10 mol in terms of palladium element.

In the coupling reaction, a base may be used in combination, if necessary.

The compounds, catalysts, and solvents used in each reaction described in <Method for producing compounds> may be used alone or in combination of two or more.

<Production method of polymer compound>
Next, a method for producing a polymer compound according to the present embodiment will be explained.

The polymer compound of the present embodiment is produced, for example, by condensation polymerization of a compound represented by formula (M-12) and another compound (for example, a compound represented by formula (M-13)). can do. In this specification, the compounds used in the production of the polymer compound of this embodiment and forming the constituent units of the polymer compound of this embodiment may be collectively referred to as "raw material monomers."

[In the formula,
U ¹ represents a group having a group obtained by removing one or more hydrogen atoms from the compound of this embodiment (the compound represented by formula (1)).
Ar ^Y1 has the same meaning as Ar ^Y1 described later.
Z ^C1 , Z ^C2 , Z ^C3 and Z ^C4 each independently represent a group selected from the group consisting of substituent A group and substituent B group. ]

For example, when Z ^C1 and Z ^C2 are groups selected from substituent group A, Z ^C3 and Z ^C4 are groups selected from substituent group B.

For example, when Z ^C1 and Z ^C2 are groups selected from substituent group B, Z ^C3 and Z ^C4 are groups selected from substituent group A.

[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 a substituent. ).

[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. A plurality of R ^C2 is A group that may be the same or different, and may be linked to each other to form a ring structure with the oxygen atom to which each is bonded;
- A group represented by BF ₃ Q' (wherein Q' represents Li, Na, K, Rb or Cs);
- A group represented by MgY' (wherein Y' represents a chlorine atom, a bromine atom, or an iodine atom);
- a group represented by ZnY'' (wherein Y'' represents a chlorine atom, a bromine atom or an iodine atom); and
-Sn(R ^C3 ) ₃ (wherein R ^C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups may have a substituent. A plurality of R ^C3 is The groups may be the same or different, and may be linked to each other to form a ring structure together with the tin atoms to which they are bonded.

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

A compound having a group selected from substituent group A and a compound having a group selected from substituent group B are condensed together by a known coupling reaction to form a group selected from substituent group A and a substituent group B. Carbon atoms that are bonded to groups selected from are bonded to each other. Therefore, if a compound having two groups selected from substituent group A and a compound having two groups selected from substituent group B are subjected to a known coupling reaction, the condensation of these compounds will occur through condensation polymerization. Polymers 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 the catalyst include bis(triphenylphosphine)palladium(II) dichloride, bis(tris-o-methoxyphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), and 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); these transition metal complexes can further be used to form triphenylphosphine, tri(o-tolyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, Examples include complexes having ligands such as 1,3-bis(diphenylphosphino)propane and bipyridyl. The catalysts may be used alone or in combination of two or more.

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; tetrabutylammonium fluoride, tetraethylammonium hydroxide, and tetraethylammonium hydroxide. Examples include organic bases such as butylammonium; phase transfer catalysts such as tetrabutylammonium chloride and tetrabutylammonium bromide. The base and the phase transfer catalyst may be used alone or in combination of two or more.

The amounts of the base and phase transfer catalyst used are usually 0.001 to 100 molar equivalents, respectively, based on the total number of moles of the raw material monomers.

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

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

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

Post-treatment of the polymerization reaction can be carried out by known methods, such as removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying. Use these methods alone or in combination. If 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 this embodiment includes at least one member selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a luminescent material, an antioxidant, and a solvent, and the compound of this embodiment. and at least one kind selected from the group consisting of the polymer compounds of the present embodiment (hereinafter collectively referred to as the compounds of the present embodiment).

In the composition of this embodiment, the compounds of this embodiment may be contained alone or in combination of two or more.

[Host material]
The compound of this embodiment can be formed into a composition with a host material having at least one function selected from the group consisting of hole-injecting property, hole-transporting property, electron-injecting property, and electron-transporting property. The external quantum efficiency of the light-emitting device obtained using this compound is particularly excellent. In the composition of this embodiment, one type of host material may be contained alone, or two or more types of host materials may be contained.

In a composition containing the compound of this embodiment and a host material, the content of the compound of this embodiment is usually 0.05 parts by weight when the total of the compound of this embodiment and host material is 100 parts by weight. ~80 parts by weight, preferably 0.1 to 50 parts by weight, more preferably 0.5 to 20 parts by weight.

The lowest excited singlet state (S1) of the host material has an energy level equivalent to S1 of the compound of this embodiment, since the external quantum efficiency of the light emitting device obtained using the composition of this embodiment is excellent. Alternatively, a higher energy level is preferred.

The host material is one that exhibits solubility in a solvent that can dissolve the compound of this embodiment, since a light emitting device obtained using the composition of this embodiment can be produced by a solution coating process. It is preferable.

Host materials are classified into low-molecular compounds and high-molecular compounds, and the composition of this embodiment may contain any of the host materials.

[Low molecule host]
The low-molecular host is preferably a compound represented by the following formula (H-1) because the light-emitting element has better luminous efficiency.

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

The molecular weight of the compound represented by formula (H-1) is preferably 1×10 ² to 5×10 ³ , more preferably 2×10 ² to 3×10 ³ , even more preferably 3×10 3 It is 10 ² to 1.5×10 ³ , particularly preferably 4×10 ² to 1×10 ³ .

The aryl group in Ar ^H1 and Ar ^H2 is preferably directly bonded to an atom constituting a ring from a monocyclic or 2 to 7 ring aromatic hydrocarbon, since the luminance life of the light emitting element of this embodiment is more excellent. A group from which one hydrogen atom is removed, more preferably a group from which one hydrogen atom directly bonded to an atom constituting a ring is removed from a monocyclic or 2- to 5-ring aromatic hydrocarbon. More preferably, it is a group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon, and these groups have a substituent. You may do so.
The aryl groups in Ar ^H1 and Ar ^H2 are preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene, benzofluorene, because the driving voltage of the light emitting device of this embodiment is further lowered. A group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from dibenzanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, or benzofluoranthene, and more preferably benzene, naphthalene, anthracene, or phenanthrene. , dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene, or benzofluorene, with one hydrogen atom directly bonded to a ring-constituting atom removed, more preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene. or a group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from fluorene, particularly preferably from benzene, naphthalene, or anthracene by removing one hydrogen atom directly bonded to an atom constituting a ring. These groups may have a substituent.

The monovalent heterocyclic group in Ar ^H1 and Ar ^H2 is preferably furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, pyridine, or diazabenzene, since the luminance lifetime of the light emitting element of this embodiment is more excellent. , triazine, azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine , phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracene, diazaanthracene, azaphenanthrene, diazaphenanthrene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene , dibenzocarbazole, indolocarbazole, indenocarbazole, azaindrocarbazole, diazaindrocarbazole, azaindenocarbazole or diazaindenocarbazole with one hydrogen atom directly bonded to an atom constituting the ring removed. and more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10- Dihydrophenazine, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindrocarbazole, diazaindrocarbazole, azaindenocarbazole or dia A group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from zaindenocarbazole, and more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, aza A group obtained by removing one hydrogen atom directly bonded to an atom constituting a ring from carbazole, diazacarbazole, phenoxazine, phenothiazine, 9,10-dihydroacridine or 5,10-dihydrophenazine, and particularly preferably pyridine. , diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene or carbazole from which one hydrogen atom directly bonded to the ring atom has been removed, particularly preferably dibenzofuran, dibenzothiophene or carbazole. A group excluding one hydrogen atom directly bonded to an atom constituting a ring, and these groups may have a substituent.

In the substituted amino groups in Ar ^H1 and Ar ^H2 , the substituent that the amino group has is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. Good too. Examples and preferred ranges of the aryl group that is a substituent on the amino group are the same as the examples and preferred ranges of the aryl group in Ar ^H1 and Ar ^H2 . Examples and preferred ranges of the monovalent heterocyclic group that is a substituent on the amino group are the same as the examples and preferred ranges of the monovalent heterocyclic group in Ar ^H1 and Ar ^H2 .

Since the luminance life of the light emitting element of this embodiment is more excellent, it is preferable that at least one of Ar ^H1 and Ar ^H2 is an aryl group or a monovalent heterocyclic group, and both Ar ^H1 and Ar ^H2 are an aryl group or a monovalent heterocyclic group. A group or a monovalent heterocyclic group is more preferable, and these groups may have a substituent.
As the aryl group and monovalent heterocyclic group in Ar ^H1 and Ar ^H2 , monocyclic, bicyclic, or tricyclic aromatic hydrocarbons, or , a monocyclic, bicyclic, or tricyclic heterocyclic compound from which one hydrogen atom directly bonded to the atom constituting the ring is removed, such as benzene, naphthalene, fluorene, pyridine, diazabenzene, and triazine. , azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, or carbazole, with one hydrogen atom directly bonded to a ring-constituting atom removed, such as a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, and a dibenzo group. A thienyl group or a dibenzofuryl group is more preferred, a phenyl group, a naphthyl group or a carbazolyl group is particularly preferred, and these groups may have a substituent.

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

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

The divalent group in L ^H1 is preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R ⁰ ), since the luminance life of the light emitting element of this embodiment is more excellent. A group represented by -, a group represented by -(O=)P(R ⁰ )-, a group represented by -O-, a group represented by -S-, -S(=O) ₂ - A group represented by -C(=O)-, more preferably an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(R ⁰ )- A group represented by -O- or -S-, more preferably an alkylene group, cycloalkylene group, arylene group or divalent heterocyclic group, particularly preferably is an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
At least one of the divalent groups in L ^H1 is preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent heterocyclic group, since the luminance life of the light emitting element of this embodiment is more excellent. Preferably, it is an arylene group or a divalent heterocyclic group, and these groups may have a substituent.

In the divalent group in L ^H1 , the arylene group is preferably an atom constituting a ring from a monocyclic or 2 to 7 ring aromatic hydrocarbon because the luminance life of the light emitting element of this embodiment is more excellent. A group from which two hydrogen atoms directly bonded to are removed, more preferably from a monocyclic or bi- to pentacyclic aromatic hydrocarbon from which two hydrogen atoms directly bonded to the atoms constituting the ring are removed. A group, more preferably a group obtained by removing two hydrogen atoms directly bonded to atoms constituting a ring from a monocyclic, bicyclic, or tricyclic aromatic hydrocarbon, and these groups are substituted with It may have a group.
Among the divalent groups in L ^H1 , the arylene group is preferably benzene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene, benzophenanthrene, because the luminance life of the light emitting element of this embodiment is better. A group obtained by removing two hydrogen atoms directly bonded to atoms constituting a ring from fluorene, dibenzoanthracene, dibenzophenanthrene, dibenzofluorene, indenofluorene, or benzofluoranthene, more preferably benzene, naphthalene, or anthracene. , phenanthrene, dihydrophenanthrene, fluorene, benzanthracene, benzophenanthrene or benzofluorene, from which two hydrogen atoms directly bonded to the atoms constituting the ring are removed, more preferably benzene, naphthalene, anthracene, phenanthrene, A group obtained by removing two hydrogen atoms directly bonded to the atoms constituting the ring from dihydrophenanthrene or fluorene, and particularly preferably two hydrogen atoms bonded directly to the atoms constituting the ring from benzene, naphthalene or anthracene. These groups may have a substituent.

Among the divalent groups in L ^H1 , a divalent heterocyclic group is preferably a monocyclic or 2- to 7-cyclic heterocyclic group, since the luminance life of the light emitting element of this embodiment is better. A group from which two hydrogen atoms are directly bonded to an atom (preferably a carbon atom) constituting the , more preferably a group consisting of an atom constituting a ring from a monocyclic or 2 to 5 ring heterocyclic compound ( Preferably, it is a group from which two hydrogen atoms are directly bonded to a carbon atom), and more preferably a group from which two hydrogen atoms are directly bonded to an atom (preferably a carbon atom) constituting a ring of a monocyclic, bicyclic, or tricyclic heterocyclic compound. A group in which two hydrogen atoms directly bonded to an atom (atom) are removed, and particularly preferably, a group in which two hydrogen atoms bonded directly to an atom (preferably a carbon atom) forming a ring from a tricyclic heterocyclic compound are removed. These groups may have a substituent.
Among the divalent groups in L ^H1 , divalent heterocyclic groups are preferably furan, thiophene, oxadiazole, thiadiazole, pyrrole, diazole, triazole, Pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, benzofuran, benzothiophene, indole, azaindole, diazaindole, benzodiazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole , phenoxazine, phenothiazine, 9,10-dihydroacridine, 5,10-dihydrophenazine, azaanthracene, diazaanthracene, azaphenanthrene, diazaphenanthrene, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, A direct bond to an atom (preferably a carbon atom) constituting a ring from benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindrocarbazole, diazaindrocarbazole, azaindenocarbazole or diazaindenocarbazole A group from which two hydrogen atoms have been removed, more preferably pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, carbazole, azacarbazole, diazacarbazole, phenoxazine, phenothiazine, 9, 10-dihydroacridine, 5,10-dihydrophenazine, benzocarbazole, azabenzocarbazole, diazabenzocarbazole, benzonaphthofuran, benzonaphthothiophene, dibenzocarbazole, indolocarbazole, indenocarbazole, azaindrocarbazole, diazain A group obtained by removing two hydrogen atoms directly bonded to an atom (preferably a carbon atom) constituting a ring from dolocarbazole, azaindenocarbazole or diazaindenocarbazole, more preferably pyridine, diazabenzene, triazine, Atoms constituting a ring (preferably carbon atoms ), and is particularly preferably a group consisting of atoms (preferably carbon atoms) that form a ring of pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, dibenzofuran, dibenzothiophene, or carbazole. ), particularly preferably a group from which two hydrogen atoms directly bonded to dibenzofuran, dibenzothiophene or carbazole are removed from a ring-constituting atom (preferably a carbon atom) and these groups may have a substituent.

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

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

In the divalent group in L ^H1 , R ⁰ is preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, More preferably, it is an aryl group, and these groups may have a substituent.
Examples and preferred ranges of the aryl group and monovalent heterocyclic group in R ⁰ in the divalent group in L ^H1 are the examples and preferred ranges of the aryl group and monovalent heterocyclic group in Ar ^H1 and Ar ^H2 , respectively. is the same as
In the divalent group in L ^H1 , examples and preferred ranges of substituents that R ⁰ may have are the same as examples and preferred ranges of substituents that Ar ^H1 and Ar ^H2 may have. .

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

Ar ^H1 and Ar ^H2 may be bonded directly or via a divalent group to form a ring, but the compound represented by formula (H-1) can be easily synthesized. Therefore, it is preferable not to form a ring.
When Ar ^H1 and Ar ^H2 are bonded via a divalent group to form a ring, the divalent group is preferably an alkylene group, a cycloalkylene group, an arylene group, or a divalent hetero cyclic group, group represented by -N(R ⁰ )-, group represented by -(O=)P(R ⁰ )-, group represented by -O-, group represented by -S- , -S(=O) ₂ - or -C(=O)-, more preferably alkylene group, cycloalkylene group, -N(R ⁰ )-. , a group represented by -O- or a group represented by -S-, more preferably an alkylene group, a group represented by -O- or a group represented by -S- , these groups may have a substituent.
In the case where Ar ^H1 and Ar ^H2 are bonded via a divalent group to form a ring, examples and preferred ranges of the arylene group, divalent heterocyclic group, and alkylene group in the divalent group are as follows: The examples and preferred ranges are the same as the arylene group, divalent heterocyclic group, and alkylene group in L ^H1 , respectively.
In the case where Ar ^H1 and Ar ^H2 are bonded via a divalent group to form a ring, examples and preferred ranges of R ⁰ in the divalent group are R ⁰ in the divalent group of L ^H1 . The examples and preferred ranges are the same.
When Ar ^H1 and Ar ^H2 are bonded via a divalent group to form a ring, examples and preferred ranges of substituents that the divalent group may have include Ar ^H1 and Ar The examples and preferred ranges of substituents that ^H2 may have are the same.

L ^H1 and Ar ^H1 may be bonded directly or via a divalent group to form a ring, but the compound represented by formula (H-1) can be easily synthesized. Therefore, it is preferable not to form a ring. Examples and preferred ranges of the divalent group in the case where L ^H1 and Ar ^H1 are bonded via a divalent ^group to form ^a ring are: The examples and preferred ranges of divalent groups in the case of bonding together to form a ring are the same as the examples and preferred ranges of divalent groups.
L ^H1 and Ar ^H2 may be bonded directly or via a divalent group to form a ring, but the compound represented by formula (H-1) can be easily synthesized. Therefore, it is preferable not to form a ring. Examples and preferred ranges of ^{the divalent group in the case where L H1 and Ar H2} ^are ^bonded via a divalent group to form a ^ring are: The examples and preferred ranges of divalent groups in the case of bonding together to form a ring are the same as the examples and preferred ranges of divalent groups.

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

[Polymer host]
Examples of the polymer host material include a polymer compound that is a hole transport material described below and a polymer compound that is an electron transport material described below.

The number average molecular weight of the polymeric host material in terms of polystyrene is preferably 5×10 ³ to 1×10 ⁶ , more preferably 1×10 ⁴ to 5×10 ⁵ , even more preferably 5×10 ⁴ to It is 2×10 ⁵ . The weight average molecular weight of the polymeric host material in terms of polystyrene is preferably 1×10 ⁴ to 2×10 ⁶ , more preferably 2×10 ⁴ to 1×10 ⁶ , even more preferably 1×10 ⁵ to It is 5×10 ⁵ .

The polymer host is preferably a polymer compound containing a structural unit represented by the following formula (Y).

[In the formula, Ar ^Y1 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. ]

The arylene group represented by Ar ^Y1 is more preferably represented by formula (A-1), formula (A-2), formula (A-6) to (A-10), formula (A-19), or formula ( A-20), more preferably formula (A-1), formula (A-2), 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 one of formulas (AA-1) to (AA-4), formulas (AA-10) to (AA-15), and formula (AA-18). A group represented by ~(AA-21), formula (AA-33) or formula (AA-34), more preferably formula (AA-4), formula (AA-10) or formula (AA- 12), a group represented by formula (AA-14) or formula (AA-33), and these groups may have a substituent.

More preferred ranges of the arylene group and 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, still more preferred The ranges are the same as the more preferred ranges and more preferred ranges of the arylene group and divalent heterocyclic group represented by Ar ^Y1 described above, respectively.

Examples of "a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" include groups represented by the following formula, which have a substituent. You may do so. Note that * represents the bonding position.

[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.

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 the structural unit represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-10), and the composition of the polymer host and the compound of this embodiment From the viewpoint of the brightness life of a light emitting element using 4) to (Y-7), and from the viewpoint of hole transport properties, preferably structural units represented by formulas (Y-8) to (Y-10).

[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 ^Y1s may be the same or different, and adjacent R ^Y1s may be bonded to each other to form a ring with the carbon atoms to which they are bonded. ]

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 R ^Y11 's 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.

[In the formula,
R ^Y1 represents 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 -. R ^Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y2s may be the same or different, and R ^Y2s may be bonded to each other to form a ring with the carbon atoms to which they are bonded. ]

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. You may do so.

In X ^Y1 , the combination of two R ^Y2s in the group represented by -C(R ^Y2 ) ₂ - is preferably such that both are alkyl groups or cycloalkyl groups, both are aryl groups, and both are monovalent hetero cyclic group, or one is an alkyl group or cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or cycloalkyl group and the other is an aryl group, and these groups may have a substituent. Two R ^Y2s may be bonded to each other to form a ring with the atoms to which they are bonded, and when R ^Y2 forms a ring, as a 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), and these groups have a substituent. You can leave it there. Note that * represents the bonding position.

In X ^Y1 , the combination of two R ^Y2s in the group represented by -C(R ^Y2 )=C(R ^Y2 )- is preferably such that both are an alkyl group or a cycloalkyl group, or one is an alkyl group. Alternatively, one is a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

In X ^Y1 , four R ^Y2s in the group represented by -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ - are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y2 may be bonded to each other to form a ring 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 substituted. It may have a group. Note that * represents the bonding position.

[In the formula, R ^Y2 represents the same meaning as above. ]

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

[In the formula, R ^Y1 and X ^Y1 represent the same meanings as above. ]

[In the formula, R ^Y1 and X ^Y1 represent the same meanings as above. ]

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

[In the formula, R ^Y11 and X ^Y1 represent the same meanings as above. ]

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

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. It's okay.

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 preferably a structural unit represented by formula (Y-4'). -6') is preferable.

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

[In the formula,
^RY1 represents the same meaning as above.
R ^Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. ]

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. You can.

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

When Ar ^Y1 in formula (Y) is an arylene group, the content of the structural unit represented by formula (Y) is determined by the brightness life of the light emitting device using the composition of the polymer host and the compound of this embodiment. Therefore, the amount is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of structural units contained in the polymer compound.

When Ar ^Y1 in the formula (Y) is a divalent heterocyclic group or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, the formula (Y ) The content of the structural units represented by ) is determined by the total amount of structural units contained in the polymer compound, since the charge transport property of the light emitting device using the composition of the polymer host and the compound of this embodiment is excellent. On the other hand, it is preferably 0.5 to 30 mol%, more preferably 3 to 20 mol%.

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

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

[In the formula,
^aX1 and ^aX2 each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^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 These groups may have a substituent. When a plurality of Ar ^X2 and Ar ^X4 exist, 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 a plurality of R ^X2 and R ^X3 exist, they may be the same or different. ]

a ^X1 is preferably 2 or less, more preferably 1, since a light emitting device using a composition of a polymer host and the compound of this embodiment has an excellent brightness life.

a ^X2 is preferably 2 or less, more preferably 0, since the luminance life of a light emitting device using a composition of a polymer host and the compound of this embodiment is excellent.

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.

^The arylene group represented by Ar ^X1 and Ar These groups may have a substituent.

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

Ar ^X1 and Ar ^X3 are preferably arylene groups which may have a substituent.

The arylene group represented by Ar ^X2 and ^Ar or a group represented by formula (A-19), and these groups may have a substituent.

The more preferred range of the divalent heterocyclic group represented by Ar ^X2 and Ar ^X4 is the same as the more preferred range of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 .

More preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group represented by Ar ^X2 and Ar ^X4 in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. The more preferable ranges are the same as the more preferable ranges and the more preferable ranges of the arylene group and divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 , respectively.

As the divalent group in which at least one arylene group represented ^by Ar ^X2 and Ar ^X4 and at least one divalent heterocyclic group are directly bonded, at least Examples include those similar to divalent groups in which one type of arylene group and at least one type of divalent heterocyclic group are directly bonded.

Ar ^X2 and Ar ^X4 are preferably arylene groups which may have substituents.

The substituents that ^the groups represented by Ar ^X1 to Ar ^X4 and R ^X1 to R You can leave it there.

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

[In the formula, R ^X4 and ^R represents a group, and these groups may have a substituent. A plurality of R ^X4 's may be the same or different. A plurality of R ^X5s may be the same or different, and adjacent R ^X5s may be bonded to each other to form a ring with the carbon atom to which they are bonded. ]

The content of the structural unit represented by formula (X) is preferably 0.1 to 50 mol% based on the total amount of structural units contained in the polymer host, since it has excellent hole transport properties. More preferably, it is 1 to 40 mol%, and still more preferably 5 to 30 mol%.

Examples of the structural unit represented by formula (X) include structural units represented by formulas (X1-1) to (X1-23), preferably formulas (X1-3) to (X1-10). ).

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

Examples of the polymer host include polymer compounds (P-1) to (P-6) shown in Table 2. Here, "other" structural units mean structural units other than the structural unit represented by formula (Y) and the structural unit represented by formula (X).

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

The polymer host may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may have other forms; A copolymer formed by polymerization is preferable.

<Production method of polymer host>
The polymer host can be produced using known polymerization methods such as those described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009). Examples include a method of polymerizing by a coupling reaction using a transition metal catalyst, such as Stille reaction, Negishi reaction, and Kumada reaction.

In the above polymerization method, the monomers may be charged in one go by charging the entire amount of the monomers into the reaction system, or after charging a portion of the monomers and reacting, the remaining monomers are added in one batch. Examples include a method of continuously or dividedly charging a monomer, a method of continuously or dividingly charging a monomer, and the like.

Examples of transition metal catalysts include palladium catalysts and nickel catalysts.

Post-treatment of the polymerization reaction can be carried out by known methods, such as removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the precipitate, and then drying. Use these methods alone or in combination. When the purity of the polymer host is low, it can be purified by conventional methods such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

[solvent]
A composition containing the compound of this embodiment and a solvent (hereinafter referred to as "ink") is suitable for producing a light emitting element using a printing method such as an inkjet printing method or a nozzle printing method.

The viscosity of the ink can be adjusted depending on the type of printing method, but if it is applied to a printing method such as inkjet printing in which the solution passes through a discharge device, clogging and flight deflection during discharge are less likely to occur. Preferably it is 1 to 20 mPa·s at 25°C.

The solvent contained in the ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples of the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole, and 4-methylanisole; toluene, 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; and 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 , N-dimethylformamide and the like. The solvents may be used alone or in combination of two or more.

In the ink, the amount of the solvent blended is usually 10,000 to 1,000,000 parts by weight, preferably 20,000 to 2,000,000 parts by weight, based on 100 parts by weight of the compound of the present embodiment.

[Hole transport material]
Hole transport materials are classified into low-molecular compounds and high-molecular compounds, preferably high-molecular compounds, and more preferably high-molecular compounds having a crosslinking group.

Examples of the polymer compound include polyvinylcarbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof. The polymer compound may be a compound to which an electron-accepting site is bonded. Examples of the electron-accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, with fullerene being preferred.

In the composition of the present embodiment, the amount of the hole transport material blended is usually 10 to 40,000 parts by weight, preferably 50 to 15,000 parts by weight, based on 100 parts by weight of the compound of the present embodiment.

The hole transport materials may be used alone or in combination of two or more.

[Electron transport material]
Electron transport materials are classified into low molecular compounds and high molecular compounds. The electron transport material may have a crosslinking group.

Examples of low-molecular 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 the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with metal.

In the composition of the present embodiment, the amount of the electron transport material blended is usually 10 to 40,000 parts by weight, preferably 50 to 15,000 parts by weight, based on 100 parts by weight of the compound of the present embodiment.

The electron transport materials may be used alone 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 compounds and high-molecular compounds, respectively. The hole injection material and the electron injection material may have a crosslinking group.

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.

Examples of polymeric compounds include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, polyquinoxaline, and derivatives thereof; conductive polymers containing an aromatic amine structure in the main chain or side chain. Polymers can be mentioned.

In the composition of this embodiment, the amount of the hole injection material and the electron injection material is usually 10 to 40,000 parts by weight, preferably 50 to 15,000 parts by weight, based on 100 parts by weight of the compound of this embodiment. Parts by weight.

The hole injection material and the electron injection material may each be used singly or in combination of two or more.

[Ion dope]
When the hole injection material or electron injection material contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1×10 ⁻⁵ S/cm to 1×10 ³ S/cm. In order to keep the electrical conductivity of the conductive polymer within this range, the conductive polymer can be doped with an appropriate amount of ions.

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

The ions to be doped may be used alone or in combination of two or more.

[Light-emitting material]
Luminescent materials (different from the compounds of this embodiment) are classified into low molecular compounds and high molecular compounds. The luminescent material may have a crosslinking group.

Examples of low-molecular compounds include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triplet luminescent complexes having iridium, platinum, or europium as the central metal.

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

The luminescent material preferably includes a triplet luminescent complex and a polymer compound.

Examples of triplet luminescent complexes include the metal complexes shown below.

In the composition of this embodiment, the content of the luminescent material is usually 1 to 40,000 parts by weight based on 100 parts by weight of the compound of this embodiment.

[Antioxidant]
The antioxidant may be any compound as long as it is soluble in the same solvent as the compound of this embodiment and does not inhibit light emission and charge transport. Examples of the antioxidant include phenolic antioxidants, phosphorus antioxidants, and the like.

In the composition of the present embodiment, the amount of antioxidant is usually 0.001 to 10 parts by weight based on 100 parts by weight of the compound of the present embodiment.

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

<Membrane>
The membrane contains the compound of this embodiment.

The film is suitable as a light emitting layer in a light emitting device.

The film can be formed using ink, such as spin coating, casting, microgravure coating, gravure coating, bar coating, roll coating, wire bar coating, dip coating, spray coating, and screen printing. , a flexographic printing method, an offset printing method, an inkjet printing method, a capillary coating method, and a nozzle coating method.

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

<Light emitting element>
The light emitting element of this embodiment is a light emitting element containing the compound of this embodiment.
The structure of the light emitting element of this embodiment includes, for example, electrodes consisting of an anode and a cathode, and a layer containing the compound of this embodiment provided between the electrodes.

[Layer structure]
The layer containing the compound of this embodiment is usually one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, and is preferably a light emitting layer. These layers each include a luminescent material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material. These layers were prepared in the same way as the film described above, by dissolving a luminescent material, a hole transporting material, a hole injection material, an electron transporting material, and an electron injection material in the above-mentioned solvents and preparing and using the ink. It can be formed using a 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 this 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 properties and electron transport properties, it is preferable to have at least one layer of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.

In addition to the compound of this embodiment, materials for the hole transport layer, electron transport layer, light emitting layer, hole injection layer, and electron injection layer include the hole transport material, electron transport material, light emitting material, and positive hole transport material described above, respectively. Examples include hole injection materials and electron injection materials.

The material for the hole transport layer, the material for the electron transport layer, and the material for the emissive layer are based on the solvent used when forming the hole transport layer, the electron transport layer, and the layer adjacent to the emissive layer, respectively, in the production of the light emitting device. When dissolved, it is preferable that the material has a crosslinking group in order to avoid dissolving the material in the solvent. After each layer is formed using a material having a crosslinking group, the layer can be made insolubilized by crosslinking the crosslinking group.

In the light-emitting device of this embodiment, the method for forming each layer such as the light-emitting layer, hole-transporting layer, electron-transporting layer, hole-injecting layer, and electron-injecting layer includes, for example, when using a low-molecular compound, vacuum formation from powder. Examples include a vapor deposition method, a method of forming a film from a solution or a molten state, and when a polymer compound is used, for example, a method of forming a film from a solution or a molten state.

The order, number, and thickness of the layers to be laminated may be adjusted in consideration of external quantum efficiency and luminance lifetime.

[Substrate/electrode]
The substrate in the light emitting element may be any substrate as long as it is capable of forming an electrode and is not chemically changed during the formation of an organic layer, and is, for example, a substrate made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, it is preferred that the electrode furthest from the substrate be transparent or translucent.

Examples of the material 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; silver-palladium-copper composite (APC); NESA, gold, platinum, silver, copper.

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

[Application]
In order to obtain planar light emission using a light emitting element, planar anodes and cathodes may be arranged so as to overlap. In order to obtain patterned light emission, there is a method of installing a mask with patterned windows on the surface of a planar light emitting element, and a method of forming an extremely thick layer to make the non-emissive area substantially non-emissive. There is a method in which the anode, the cathode, or both electrodes are formed in a pattern. By forming a pattern using any of these methods and arranging some electrodes so that they can be turned on and off independently, a segment type display device that can display numbers, characters, etc. can be obtained. In order to obtain a dot matrix display device, both the anode and the cathode may be formed in a stripe shape and arranged so as to be orthogonal to each other. Partial color display and multicolor display are possible by using a method of painting multiple types of polymer compounds with different emission colors, a method of using a color filter, or a fluorescence conversion filter. The dot matrix display device can be driven passively, or can be driven actively in combination with a TFT or the like. These display devices can be used for displays on computers, televisions, mobile terminals, and the like. A planar light emitting element can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar light source for illumination. If a flexible substrate is used, it can also be used as a curved light source and display device.

Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited to these Examples.

In the examples, the number average molecular weight (Mn) in terms of polystyrene and the weight average molecular weight (Mw) in terms of polystyrene of the polymer compound were determined using one of the following size exclusion chromatography (SEC) methods using tetrahydrofuran as a moving phase. It was determined by In addition, each measurement condition of SEC is as follows.

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

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

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

NMR was measured by the following method.
Add 5 to 10 mg of the measurement sample to about 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N,N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 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 high performance liquid chromatography (HPLC) area percentage value was used as an indicator of the purity of the compound. Unless otherwise specified, this value is a value at UV=254 nm using HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). 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 HPLC depending on the concentration. As the mobile phase for HPLC, the ratio of acetonitrile/tetrahydrofuran was varied from 100/0 to 0/100 (volume ratio), and the mixture was flowed at a flow rate of 1.0 mL/min. The column used was Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as a detector.

<Synthesis of compounds>
Compounds S1 to S14 in the following Examples and Comparative Examples were synthesized as follows.

・Synthesis of compound S1

(Compound 1a)
After creating an argon gas atmosphere in the reaction vessel, 6(5H)-phenanthridinone (10.2 g) and N,N-dimethylformamide (306 mL) were added and stirred, and N-bromosuccinimide (9.3 g) was added. The mixture was heated and stirred in an oil bath at 65° C. for 4 hours. After cooling to room temperature, ion-exchanged water (102 mL) was added and stirred. The resulting suspension was washed on a filter with ion-exchanged water (51 mL) and N,N-dimethylformamide (153 mL), and the filtered substance obtained was washed three times with methanol (153 mL). The obtained cream-colored solid was dried under reduced pressure at 50° C. to obtain Compound 1a (12.0 g, cream-colored solid). The LC area percentage of compound 1a was greater than 96%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.87 (1H, broad-s), 8.46 (1H, d), 8.37 (1H, d), 8.25 (1H, d), 7.84 (1H, t), 7.65 (1H, t), 7.58 (1H, dd), 7.09 (1H, d).
TLC-MS (ESI, positive): [M+H] ⁺ =274.

(Compound 1b)
After creating an argon gas atmosphere in the reaction vessel, compound 1a (10.0 g), 4,4,5,5-tetramethyl-2-[4-(1,1,3,3-tetramethylbutyl)phenyl] -1,3,2-dioxaborolane (12.7 g), 4-methyltetrahydropyran (172 mL), [(di(1-adamantyl)-N-butylphosphine)-2-(2'-amino-1,1' -biphenyl)]palladium(II) methanesulfonate (0.27 g), 40% aqueous tetrabutylammonium hydroxide solution (71 mL), and ion-exchanged water (213 mL) were added, and the mixture was heated and stirred in an oil bath at 100°C for 4 hours. After cooling to room temperature, the obtained suspension was washed with ion-exchanged water (100 mL), methanol (2250 mL) was added to the obtained suspension, stirred for 10 minutes, and the obtained suspension was filtered. The top was washed with methanol (420 mL). Compound 1b (15.4 g, light gray solid) was obtained by drying the obtained light gray solid under reduced pressure at 50°C. The LC area percentage of Compound 1b was greater than 99.8%.
^1H -NMR (400MHz, CD ₂ Cl ₂ ): δ (ppm) = 9.37 (1H, broad-s), 8.48 (1H, d), 8.44 (1H, d), 8.41 (1H, d), 7.83 (1H, td), 7.73 (1H, dd), 7.65-7.57 (3H, m), 7.49 (2H, d), 7.28 ( 1H, d), 1.80 (2H, s), 1.40 (6H, s), 0.75 (9H, s).
TLC-MS (ESI, positive): [M+H] ⁺ =384.

(Compound 1c)
After creating an argon gas atmosphere in the reaction vessel, compound 1b (15.0 g) and N,N-dimethylformamide (450 mL) were added and stirred, and N-bromosuccinimide (18.1 g) was added, and the mixture was heated in an oil bath at 65°C. The mixture was heated and stirred for 11 hours. After cooling to room temperature, ion-exchanged water (140 mL) was added and stirred. The obtained suspension was washed with ion-exchanged water (70 mL) and N,N-dimethylformamide (210 mL) on a filter, and the obtained filter cake was washed twice with N,N-dimethylformamide (42 mL). did. The obtained filtered material was washed with methanol (70 mL). The obtained flesh-colored solid was dried under reduced pressure at 50° C. to obtain Compound 1c (15.4 g, flesh-colored solid). The LC area percentage of Compound 1c was greater than 93%.
^1H -NMR (400MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.92 (1H, broad-s), 8.46 (1H, dd), 8.42-8.35 (2H, m) , 7.96 (1H, d), 7.83 (1H, td), 7.64 (1H, t), 7.58 (2H, d), 7.50 (2H, d), 1.80 ( 2H, s), 1.40 (6H, s), 0.75 (9H, s).
TLC-MS (ESI, positive): [M+H] ⁺ =462.

(Compound 1d)
After creating an argon gas atmosphere in the reaction vessel, compound 1c (13.3 g), bis(pinacolato)diboron (11.0 g), potassium acetate (11.3 g), [1,1'-bis(diphenylphosphino)] Ferrocene]palladium(II) dichloride dichloromethane adduct (0.47 g), 1,2-dimethoxyethane (133 mL), and toluene (399 mL) were added, and the mixture was heated and stirred at 75° C. in an oil bath for 2 hours. After cooling to room temperature, toluene (67 mL) was added and stirred, and the resulting suspension was filtered through a filter lined with Celite, and the filtered material was washed with toluene (60 mL). The obtained filtrate was concentrated under reduced pressure. The obtained crude product was dissolved in toluene (133 mL), activated carbon (5.3 g) and activated clay (8.0 g) were added, stirred for 10 minutes, filtered through a filter lined with Celite, and the filtered material was Washed with toluene (133 mL). The obtained filtrate was concentrated under reduced pressure. The obtained crude product was dissolved in toluene (147 mL), activated carbon (7.3 g) was added, stirred for 10 minutes, filtered through a filter lined with Celite, and the filtered product was washed with toluene (133 mL). The obtained filtrate was concentrated under reduced pressure. The obtained crude product was recrystallized from a mixed solvent of toluene and acetonitrile. Compound 1d (9.2 g, white solid) was obtained by drying the obtained white solid under reduced pressure at 50°C. The LC area percentage of Compound 1d was greater than 97%.
^1H -NMR (400MHz, CD ₂ Cl ₂ ): δ (ppm) = 10.30 (1H, broad-s), 8.55 (1H, s), 8.44 (1H, d), 8.39 (1H, d), 8.16 (1H, s), 7.79 (1H, t), 7.64-7.55 (3H, m), 7.49 (2H, d), 1.80 ( 2H, s), 1.42 (12H, s), 1.20 (6H, s), 0.74 (9H, s).
TLC-MS (ESI, positive): [M+H] ⁺ =510.

(Compound 1e)
After creating an argon gas atmosphere in the reaction vessel, compound 1d (7.0 g), 1,4-dibromo-2,5-diiodobenzene (3.19 g), toluene (105 mL), and tetrakis(triphenylphosphine)palladium were added. (0) (0.76 g), 40% aqueous tetrabutylammonium hydroxide solution (21 mL), and ion-exchanged water (85 mL) were added, and the mixture was heated and stirred in an oil bath at 70° C. for 13 hours. After cooling to room temperature, the resulting suspension was washed three times with ion exchange water (175 mL), and the resulting suspension was washed with ethanol (350 mL) on a filter. Compound 1e (5.8 g, white solid) was obtained by drying the obtained white solid under reduced pressure at 50°C. The LC area percentage of compound 1e was greater than 97%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.60 (2H, s), 8.50 (2H, d), 8.44 (2H, d), 8.26 (2H , s), 7.93-7.82 (4H, m), 7.78 (2H, s), 7.75-7.76 (6H, m), 7.56 (4H, m), 1. 81 (4H, s), 1.41 (12H, s), 0.76 (18H, s).
TLC-MS (ESI, positive): [M+H] ⁺ =997.

(Compound 1f)
After creating an argon gas atmosphere in the reaction vessel, compound 1e (5.7 g), potassium carbonate (3.16 g), N,N-dimethylacetamide (100 mL), copper(I) iodide (0.32 g), 1 , 10-phenanthroline (0.31 g) was added, and the mixture was heated and stirred in an oil bath at 130° C. for 3 hours. After cooling to room temperature, toluene (100 mL) was added, the resulting suspension was washed three times with ion-exchanged water (100 mL), and the resulting suspension was washed with methanol (500 mL) on a filter. The filtered product was washed three times with toluene (30 mL) on the filter. The obtained pale yellow solid was dried under reduced pressure at 50°C to obtain Compound 1f (3.9 g, pale yellow solid). The LC area percentage of compound 1f was greater than 98%.
TLC-MS (ESI, positive): [M+H] ⁺ =837.

(1 g of compound)
After creating an argon gas atmosphere in the reaction vessel, 1-bromo-3,5-dihexylbenzene (2.56 g) and tetrahydrofuran (220 mL) were added, and the mixture was cooled in a bath at -65°C or below, and the s-butyllithium solution ( 1.2 mol/L, cyclohexane/hexane solution) (6.3 mL) was added dropwise, and the mixture was stirred for 2 hours. Compound 1f (2.2 g) was added to the obtained solution, the temperature was raised to room temperature, and the mixture was stirred at room temperature for 2 hours. After cooling on ice, methanol (4 mL) was added, the temperature was raised to room temperature, toluene (50 mL) was added, and the resulting solution was washed three times with ion-exchanged water (20 mL). The obtained organic phase was dried over magnesium sulfate, filtered through a filter lined with Celite, and the filtered product was washed with toluene. The obtained filtrate was concentrated under reduced pressure. The obtained crude product was washed with heptane. The obtained yellow solid was dried under reduced pressure at 50°C to obtain 1 g (3.4 g, yellow solid) of the compound. The LC area percentage of 1 g of the compound was greater than 84%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.21 (2H, s), 8.17 (2H, d), 8.10 (2H, s), 7.89 (2H , d), 7.70 (4H, d), 7.59 (2H, d), 7.53 (4H, d), 7.44 (2H, t), 7.31 (2H, t), 7 .20 (4H, s), 6.91 (2H, s), 3.48 (2H, s), 2.49 (8H, t), 1.85 (4H, s), 1.53-1. 42 (8H, m), 1.44 (12H, s), 1.32-1.20 (8H, m), 1.20-1.15 (16H, m), 0.81 (18H, s) , 0.71 (12H, s).

(Compound 1h)
After creating an argon gas atmosphere in the reaction vessel, 1 g (3.1 g) of the compound and 1,4-dioxane (310 mL) were added, and trifluoromethanesulfonic acid (1.7 g) was added dropwise at room temperature, followed by stirring at room temperature for 2 hours. Stirred. The resulting suspension was washed with 1,4-dioxane on a filter. The obtained orange solid was dried under reduced pressure at 50°C to obtain Compound 1h (3.5 g, orange solid).
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 9.11 (2H, d), 9.05 (2H, s), 8.50 (2H, t), 8.34 (2H, d), 8.19 (2H, s), 8.07 (2H, t), 7.80 (2H, s), 7.79 (4H, d), 7.71 (4H, d), 7. 57 (4H, s), 7.03 (2H, s), 2.95-2.77 (8H, m), 1.91 (4H, s), 1.82-1.68 (8H, m) , 1.51 (12H, s), 1.37 (8H, quin), 1.21-1.08 (16H, m), 0.83 (18H, s), 0.71 (12H, t).

(Compound S1)
After creating an argon gas atmosphere in the reaction vessel, compound 1h (3.0 g) and cyclopentyl methyl ether (300 mL) were added, cooled in a bath at -65°C or lower, and octylmagnesium bromide solution (2 mol/L, diethyl ether solution) was added. ) (4.7 mL) was added dropwise and stirred for 2 hours. Methanol (6 mL) was added, the temperature was raised to room temperature, toluene (30 mL) was added, and the resulting solution was washed three times with ion-exchanged water (30 mL). After drying the obtained organic phase with magnesium sulfate, activated carbon (0.6 g) was added and stirred for 10 minutes, filtered through a filter lined with Celite, and the filtered product was washed with toluene. The obtained filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and heptane). The obtained crude product was recrystallized multiple times from a mixed solvent of toluene, ethyl acetate, and acetonitrile. Compound S1 (1.7 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound S1 was greater than 99.4%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.81-8.13 (4H, m), 7.94-7.88 (2H, m), 7.68-7. 63 (4H, m), 7.50 (4H, d), 7.48-7.39 (2H, m), 7.30 (2H, t), 7.25-7.19 (4H, m) , 7.16 (2H, m), 7.08 (2H, m), 6.95-6.90 (2H, m), 3.30-2.40 (12H, m), 1.82 (4H , s), 1.60-1.40 (20H, m), 1.30-0.30 (84H, m).
LC-MS (APCI, positive): [M+H] ⁺ =1522.

・Synthesis of compound S2

(Compound S2)
After creating an argon gas atmosphere in the reaction vessel, compound 1h (0.13 g) and cyclopentyl methyl ether (13 mL) were added, cooled in a bath at -65°C or lower, and methylmagnesium bromide solution (1 mol/L, tetrahydrofuran solution) was added. (0.4 mL) was added dropwise and stirred for 2 hours. Methanol (0.3 mL) was added, the temperature was raised to room temperature, toluene (3 mL) was added, and the resulting solution was washed three times with ion-exchanged water (2 mL). After drying the obtained organic phase with magnesium sulfate, activated carbon (20 mg) was added and stirred for 10 minutes, filtered through a filter lined with Celite, and the filtered product was washed with toluene. The obtained filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and heptane). The obtained crude product was recrystallized from a mixed solvent of toluene and methanol. Compound S2 (0.09 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound S2 was greater than 99.6%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ) δ (ppm) = 8.10-8.05 (4H, m), 7.86 (2H, d), 7.65 (4H, d), 7. 51 (4H, d), 7.35-7.28 (6H, m), 7.24-7.19 (2H, m), 7.16 (2H, t), 7.06-6.98 ( 4H, m), 2.63-2.50 (8H, m), 2.13-2.05 (6H, m), 1.84 (4H, s), 1.62-1.50 (8H, m), 1.44 (12H, s), 1.30-1.10 (24H, m), 0.80 (18H, s), 0.73-0.65 (12H, m).
LC-MS (APCI, positive): [M+H] ⁺ =1326.

・Synthesis of compound S3

(Compound S3)
After creating an argon gas atmosphere in the reaction vessel, magnesium (0.09 g), tetrahydrofuran (5 mL), and iodine (0.001 g) were added, and the mixture was heated and stirred in an oil bath at 70° C. for 1 hour. 1-bromo-3,5-dihexylbenzene (1.0 g) and tetrahydrofuran (1 mL) were added dropwise, heated and stirred in an oil bath at 70°C for 1 hour, cooled to room temperature, and 3,5-dihexylphenylmagnesium bromide solution ( 0.43 mol/L, tetrahydrofuran solution) was prepared.
In another reaction vessel, after creating an argon gas atmosphere in the reaction vessel, compound 1h (0.13 g) and cyclopentyl methyl ether (13 mL) were added, and the mixture was cooled in a bath at -65°C or lower to prepare 3,5 -Dihexylphenylmagnesium bromide solution (0.43 mol/L, tetrahydrofuran solution) (1.52 mL) was added dropwise, and the mixture was stirred for 2 hours. Methanol (0.3 mL) was added, the temperature was raised to room temperature, toluene (3 mL) was added, and the resulting solution was washed three times with ion-exchanged water (2 mL). After drying the obtained organic phase with magnesium sulfate, activated carbon (20 mg) was added and stirred for 10 minutes, filtered through a filter lined with Celite, and the filtered product was washed with toluene. The obtained filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and heptane). The obtained crude product was recrystallized from a mixed solvent of toluene and acetonitrile. Compound S3 (0.08 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound S3 was greater than 98%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.03 (2H, d), 8.01 (2H, d), 7.72 (2H, d), 7.57 (4H , d), 7.47 (4H, d), 7.37 (2H, td), 7.24 (2H, td), 7.15 (2H, dd), 6.92 (4H, t), 6 .85-6.79 (10H, m), 2.39 (16H, t), 1.81 (4H, s), 1.47-1.31 (28H, m), 1.12-0.91 (48H, m), 0.79 (18H, t), 0.63 (24H, t).
LC-MS (APCI, positive): [M+H] ⁺ =1786.

・Synthesis of compound S4

(Compound 2a)
After creating an argon gas atmosphere in the reaction vessel, compound 1f (0.5 g) and tetrahydrofuran (50 mL) were added, cooled in a bath at -65°C or lower, and dissolved in n-butyllithium solution (1.7 mol/L, hexane solution). ) (1.4 mL) was added dropwise, the temperature was raised to room temperature, and the mixture was stirred at room temperature for 3 hours. After cooling on ice, methanol (1 mL) was added, the temperature was raised to room temperature, toluene (20 mL) was added, and the resulting solution was washed three times with ion-exchanged water (20 mL). The obtained organic phase was dried over magnesium sulfate, filtered through a filter lined with Celite, and the filtered product was washed with toluene. The obtained filtrate was concentrated under reduced pressure. The obtained crude product was washed with heptane. Compound 2a (0.5 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound 2a was greater than 86%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.90-8.63 (2H, m), 8.43-8.30 (2H, m), 8.20-8. 13 (2H, m), 8.81-7.40 (16H, m), 3.60-3.28 (2H, m), 3.20-2.80 (4H, m), 2.35- 2.05 (4H, m), 1.90-1.80 (4H, m), 1.55-0.01 (40H, t).

(Compound 2b)
After creating an argon gas atmosphere in the reaction vessel, compound 2a (0.4 g) and 1,4-dioxane (40 mL) were added, trifluoromethanesulfonic acid (0.3 g) was added dropwise at room temperature, and the mixture was heated at room temperature for 2 hours. Stirred. The resulting suspension was washed with 1,4-dioxane on a filter. Compound 2b (0.47 g, red solid) was obtained by drying the obtained red solid under reduced pressure at 50°C.

(Compound S4)
After creating an argon gas atmosphere in the reaction vessel, compound 2b (0.4 g) and cyclopentyl methyl ether (40 mL) were added, and the mixture was cooled in a bath at -65°C or below, and a butylmagnesium bromide solution (2 mol/L, diethyl ether solution) was added. ) (1.3 mL) was added dropwise and stirred for 2 hours. Methanol (1 mL) was added, the temperature was raised to room temperature, toluene (7 mL) was added, and the resulting solution was washed three times with ion-exchanged water (3 mL). The obtained organic phase was dried over magnesium sulfate, filtered through a filter lined with Celite, and the filtered product was washed with toluene. The obtained filtrate was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and heptane). The obtained crude product was recrystallized several times from a mixed solvent of toluene and heptane. Compound S4 (0.1 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound S4 was greater than 98%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.57 (2H, s), 8.29 (2H, s), 8.10 (2H, d), 8.05 (2H , s), 7.73 (4H, d), 7.53 (6H, d), 7.43-7.35 (4H, m), 3.16 (4H, td), 2.22 (4H, td), 1.82 (4H, s), 1.42 (12H, s), 1.15-0.65 (34H, m), 0.55 (12H, t).
LC-MS (APCI, positive): [M+H] ⁺ =1034.

-Synthesis of Compound S5 Compound S5 was synthesized according to the method described in International Publication No. 2012-086671.

-Synthesis of compound S6 Compound S6 was synthesized according to the method described in International Publication No. 2018-199283.

-Synthesis and acquisition of compounds S7 to S11 Compound S7 was synthesized according to the method described in JP-A-2012-144722.
Compound S8 was synthesized according to the method described in International Publication No. 2011-049241.
Compound S9 was synthesized according to the method described in WO 2002-045184.
Compound S10 was synthesized according to the method described in WO 2008-038747.
A commercially available product was used as compound S11.

・Synthesis of compound S12

(Compound 3a)
After creating an argon gas atmosphere in the reaction vessel, magnesium (7.81 g), tetrahydrofuran (81 mL), and iodine (0.026 g) were added, and the mixture was heated and stirred in an oil bath at 70° C. for 1 hour. 3-Bromo-3'-chloro-1,1'-biphenyl (28.5 g) and tetrahydrofuran (2 mL) were added dropwise, heated and stirred in an oil bath at 70°C for 1 hour, cooled to room temperature, and 3-(3' -Chloro-phenyl)phenylmagnesium bromide solution (1.22 mol/L, tetrahydrofuran solution) was prepared.
In another reaction container, after creating an argon gas atmosphere in the reaction container, compound 2a (8.5 g) and cyclopentyl methyl ether (850 mL) were added, and trifluoromethanesulfonic acid (6.1 g) was added dropwise at room temperature. The mixture was stirred at room temperature for 2 hours to obtain a suspension of compound 2b. The resulting suspension was cooled in a bath at -65°C or lower, and the prepared 3-(3'-chloro-phenyl)phenylmagnesium bromide solution (1.22 mol/L, tetrahydrofuran solution) (83 mL) was added dropwise. Stirred for 2 hours. Methanol (17 mL) was added, and after the temperature was raised to room temperature, ion exchange water (85 mL) was added, and the resulting solution was washed three times with ion exchange water (85 mL). The obtained organic phase was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and hexane). The obtained crude product was recrystallized from a mixed solvent of tetrahydrofuran and methanol. Compound 3a (10.0 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound 3a was greater than 84%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.12-8.06 (4H, m), 7.99-7.91 (4H, m), 7.67-7. 27 (25H, m), 7.25-7.05 (5H, m), 3.41-3.25 (2H, m), 2.75-2.60 (2H, m), 1.83 ( 4H, s), 1.42 (12H, s), 1.15-0.85 (6H, m), 0.80 (18H, s), 0.60-0.43 (8H, m).
LC-MS (APCI, positive): [M+H] ⁺ =1293.

(Compound S12)
After creating an argon atmosphere in the reaction vessel, compound 3a (7.6 g), bispinacolato diboron (4.5 g), tris(dibenzylideneacetone)dipalladium (0.17 g), and 2-dicyclohexylphosphino-2 were added. ',4',6'-triisopropylbiphenyldicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.31 g), potassium acetate (3. 5 g), toluene (304 mL), and ethylene glycol dimethyl ether (228 mL) were added, and the mixture was heated and stirred in an oil bath at 90° C. for 10 hours. Then, toluene (61 mL) and water (23 mL) were added, and the mixture was stirred at room temperature. The liquid was separated and washed three times with ion-exchanged water. The obtained organic phase was concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (mixed solvent of toluene and hexane). The obtained crude product was recrystallized from a mixed solvent of toluene and heptane. Compound S12 (1.4 g, yellow solid) was obtained by drying the obtained yellow solid under reduced pressure at 50°C. The LC area percentage of compound S12 was greater than 98%.
¹ H-NMR (400 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.10 (2H, d), 8.08 (2H, s), 8.83-7.96 (4H, m), 7 .94 (2H, s), 7.76 (2H, d), 7.67-7.59 (8H, m), 7.55 (2H, d), 7.52-7.45 (6H, m ), 7.44-7.36 (4H, m), 7.32 (2H, t), 7.20 (2H, t), 7.10 (2H, t), 3.32 (2H, td) , 2.65 (2H, td), 1.83 (4H, s), 1.45 (12H, s), 1.29 (24H, s), 1.03 (4H, sextet), 0.97- 0.83 (2H, m), 0.80 (18H, s), 0.52-0.35 (8H, m).
TLC-MS (positive): [M+H] ⁺ =1478.

-Synthesis and acquisition of compounds S13 to S14 A commercially available product was used as compound S13.
Compound S14 was synthesized according to the method described in WO 2009-131255.

Synthesis example 1
<Synthesis of polymer compound P1>
The polymer compound P1 was synthesized using the mixture P1-1 (compound S7, compound S8, compound S9, and compound S10) shown in Table 3 according to the method described in JP-A-2012-144722. The Mn of the polymer compound P1 was 8.0×10 ⁴ and the Mw was 2.6×10 ⁵ .

The polymer compound P1 consists of a structural unit derived from compound S7, a structural unit derived from compound S8, a structural unit derived from compound S9, and a structural unit derived from compound S10, based on the theoretical value determined from the amount of raw materials to be charged. It is presumed that the derived structural units are random copolymers (copolymers without terminal blocks and non-terminal blocks) composed of a molar ratio of 50:30:12.5:7.5. Ru.

Synthesis example 2
<Synthesis of polymer compound P2>
Polymer compound P2 was synthesized using mixture P2-1 (compound S7 and compound S11) shown in Table 4 according to the method described in JP-A-2012-144722. The Mn of the polymer compound P2 was 6.9×10 ⁴ and the Mw was 2.1×10 ⁵ .

The polymer compound P2 is a compound composed of a structural unit derived from the compound S7 and a structural unit derived from the compound S11 in a molar ratio of 50:50, based on the theoretical value determined from the amount of the charged raw materials. It is presumed to be a polymer.

Synthesis example 3
<Synthesis of polymer compound P3>
Polymer compound P3 was synthesized by the following method.
(Step 1) After creating an inert gas atmosphere in the reaction vessel, the above compound S13 (0.443 g), the above compound S12 (0.120 g), the above compound S13 (0.516 g), dichlorobis(tris- o-Methoxyphenylphosphine) palladium (1.46 mg) and toluene (31 mL) were added and heated to 80°C.
(Step 2) Thereafter, a 20% by mass aqueous tetraethylammonium hydroxide solution (20.7 g) was added dropwise to the reaction vessel, and the mixture was refluxed for 2 hours.
(Step 3) Then, phenylboronic acid (48.9 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.50 mg) were added to the reaction vessel, and the mixture was stirred at 80° C. for 3 hours.
(Step 4) After cooling the obtained reaction mixture, an aqueous sodium diethyldithiacarbamate solution was added, and the mixture was stirred at 40°C for 1 hour. After cooling the obtained reaction solution and removing the aqueous layer, the obtained organic layer was washed twice with 3% by mass aqueous ammonia and twice with water. When the obtained solution was added dropwise to methanol and stirred, a precipitate was generated. The obtained precipitate was dissolved in toluene (71 mL), alumina (41 g) was added, and after stirring for 3 hours, the obtained suspension was purified by passing it through a silica gel column. When the obtained solution was added dropwise to methanol and stirred, a precipitate was generated. The obtained precipitate was collected by filtration and dried to obtain 0.44 g of polymer compound P3. The Mn of the polymer compound P3 was 5.2×10 ⁴ and the Mw was 1.1×10 ⁵ .

The polymer compound P3 has a structural unit derived from the compound S13, a structural unit derived from the compound S12, and a structural unit derived from the compound S14 from a theoretical value determined from the amount of the raw materials to be charged. It is presumed to be a random copolymer (a copolymer without terminal blocks and non-terminal blocks) composed of a molar ratio of 5:50.

The emission spectrum of the compound was measured using the method described below.
The compounds were dissolved in xylene or chloroform to a concentration of 0.0008% by weight. The obtained solution was placed in a 1 cm square quartz cell, and then nitrogen gas was bubbled to remove oxygen to prepare a measurement sample. The emission spectrum of the obtained measurement sample was measured using a spectrophotometer (manufactured by JASCO Corporation, FP-6500), and from the obtained emission spectrum, the maximum wavelength and area ratio (maximum The value obtained by dividing the area value in the range of -0.12 eV to +0.07 eV from the intensity position by the area value of the entire emission spectrum) was calculated. Note that the excitation wavelength was 300 nm.

The area ratio obtained above indicates the ratio of the emission spectrum included within a predetermined range from the maximum intensity position of the emission spectrum to the entire emission spectrum. That is, a large area ratio indicates that the spectral width of the emission spectrum is narrow.

<Examples C1 to C5 and Comparative Example CC1> Measurement of emission spectra of compounds S1 to S5 and 1 g of xylene solution Emission spectra were measured using compounds S1 to S5 and 1 g of xylene solution. Table 5 shows the maximum wavelength and area ratio of the emission spectrum of each compound.

<Example C6 and Comparative Example CC2> Measurement of emission spectra of chloroform solutions of compounds S1 and S5 Emission spectra were measured using chloroform solutions of compounds S1 and S5. Table 6 shows the maximum wavelength and area ratio of the emission spectrum of each compound.

From the results in Tables 5 and 6, compounds S1 to S4 and 1g have higher area ratios of emission spectra, that is, narrower spectral widths of emission spectra, than compound S5.

<Example D1> Production and evaluation of light emitting element D1 (fabrication of light emitting element D1)
(Formation of anode and hole injection layer)
An anode was formed by applying an ITO film with a thickness of 45 nm to a glass substrate by sputtering. On the anode, a hole injection material ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) was deposited to a thickness of 35 nm by spin coating to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and then further heated at 240° C. for 15 minutes to form a hole injection layer.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by mass. Using the obtained xylene solution, a film with a thickness of 20 nm was formed by spin coating on the hole injection layer, and a positive film was formed by heating it on a hot plate at 180°C for 60 minutes in a nitrogen gas atmosphere. A pore transport layer was formed. This heating brought the polymer compound P1 into a crosslinked state.

(Formation of light emitting layer)
Polymer compound P2 and compound S1 (polymer compound P2/compound S1 = 97% by mass/3% by mass) were dissolved in xylene at a concentration of 1.2% by mass. Using the obtained xylene solution, a film with a thickness of 60 nm was formed by spin coating on the hole transport layer, and a light emitting layer was formed by heating at 150° 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 was formed to 1.0×10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was applied on the light-emitting layer as a cathode, and then on the sodium fluoride layer. Aluminum was deposited to a thickness of about 80 nm. After the vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate, thereby producing a light emitting element D1.

(Evaluation of light emitting element D1)
Light emission was observed by applying a voltage to the light emitting element D1, and the maximum wavelength and area ratio of the emission spectrum at 1000 cd/m ² were 455 nm and 0.642, respectively. These results are shown in Table 7 below.

<Comparative Example CD1> Production and evaluation of light emitting device CD1 A light emitting device was produced in the same manner as Example D1 except that polymer compound P2 and compound S5 were used instead of polymer compound P2 and compound S1 in Example D1. CD1 was produced.
Light emission was observed by applying a voltage to the light emitting element CD1, and the maximum wavelength and area ratio of the emission spectrum at 1000 cd/m ² were 460 nm and 0.578, respectively. These results are shown in Table 7 below.

<Example D2> Production and evaluation of light emitting element D2 (fabrication of light emitting element D2)
(Formation of anode and hole injection layer)
An anode was formed by applying an ITO film with a thickness of 45 nm to a glass substrate by sputtering. On the anode, a hole injection material ND-3202 (manufactured by Nissan Chemical Industries, Ltd.) was deposited to a thickness of 35 nm by spin coating to form a coating film. The substrate on which the coating film was formed was heated on a hot plate at 50° C. for 3 minutes in an air atmosphere, and then further heated at 240° C. for 15 minutes to form a hole injection layer.

(Formation of light emitting layer)
Compound S6 and compound S1 (compound S6/compound S1 = 97% by mass/3% by mass) were dissolved in toluene at a concentration of 1.8% by mass. Using the obtained toluene solution, a film with a thickness of 60 nm was formed by spin coating on the hole transport layer, and a light emitting layer was formed by heating at 130° 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 was formed to 1.0×10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was applied on the light-emitting layer as a cathode, and then on the sodium fluoride layer. Aluminum was deposited to a thickness of about 80 nm. After the vapor deposition, the substrate on which the cathode was formed was sealed with a glass substrate, thereby producing a light emitting element D2.

(Evaluation of light emitting element D2)
Light emission was observed by applying a voltage to the light emitting element D2, and the maximum wavelength and area ratio of the emission spectrum at 1000 cd/m ² were 460 nm and 0.644, respectively. These results are shown in Table 8 below.

<Comparative Example CD2> Production and evaluation of light emitting device CD2 A light emitting device CD2 was produced in the same manner as in Example D2, except that compound S6 and compound S5 were used instead of compound S6 and compound S1 in Example D2. .
Light emission was observed by applying a voltage to the light emitting element CD2, and the maximum wavelength and area ratio of the emission spectrum at 1000 cd/m ² were 470 nm and 0.582, respectively. These results are shown in Table 8 below.

From these results, the light-emitting element containing the compound S1 in the light-emitting layer has a higher area ratio of the emission spectrum, that is, the spectral width of the emission spectrum is narrower, compared to the light-emitting element containing the compound S5 in the light-emitting layer.

<Example D3> Production and evaluation of light emitting element D3 (fabrication of light emitting element D3)
Instead of "polymer compound P2 and compound S1 (polymer compound P2/compound S1 = 97% by mass/3% by mass) were dissolved at a concentration of 1.2% by mass" in (formation of light emitting layer), Light-emitting element D3 was produced in the same manner as Example D1, except that polymer compound P3 was dissolved at a concentration of 1.4% by mass.

(Evaluation of light emitting element D3)
Light emission was observed by applying a voltage to the light emitting element D3, and the maximum wavelength and area ratio of the emission spectrum at 1000 cd/m ² were 460 nm and 0.691, respectively. These results are shown in Table 9 below.

<Example D4> Production and evaluation of light emitting element D4 (fabrication of light emitting element D4)
Instead of "polymer compound P2 and compound S1 (polymer compound P2/compound S1 = 97% by mass/3% by mass) were dissolved at a concentration of 1.2% by mass" in (formation of light emitting layer), The procedure was the same as in Example D1, except that polymer compound P3 and polymer compound P2 (polymer compound P3/polymer compound P2 = 20% by mass/80% by mass) were dissolved at a concentration of 1.4% by mass. Thus, a light emitting device D4 was manufactured.

(Evaluation of light emitting element D4)
Light emission was observed by applying a voltage to the light emitting element D4, and the maximum wavelength and area ratio of the emission spectrum at 1000 cd/m ² were 455 nm and 0.650, respectively. These results are shown in Table 9 below.

<Examples Q1 to Q50 and Comparative Example CQ1>
For compounds S1 to S4 and the following compounds S12 to S55, the area ratios of the emission spectra were calculated by the Franck-Condon analysis described below. The area ratios of the emission spectra of each compound are shown in Tables 10 to 14.

As a computational chemical method, the calculation was performed using density functional theory based on an ab initio method.
Specifically, using the quantum chemical calculation program Gaussian 16, structure optimization and Franck-Condon analysis were performed using 6-31G* as a basis using density functional theory at the B3LYP level. From the emission spectrum obtained by Franck-Condon analysis, the area ratio of the emission spectrum (value obtained by dividing the area value in the range of -0.12 eV to +0.07 eV from the maximum intensity position by the area value of the entire emission spectrum) was calculated. .

As shown in Tables 10 to 14, Compounds S1 to S4 of Examples and Compounds S12 to S55 have higher area ratios of emission spectra, that is, narrower spectral widths of emission spectra, than Compound S56 of Comparative Example. .

Claims

A compound represented by formula (1).

[In the formula,
Ar 1 represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded.
Ring Ar 2 and ring Ar 3 each independently represent an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded. However, at least one of ring Ar 2 and ring Ar 3 is condensed with the ring skeleton represented by formula (2) at least at the * position. When a plurality of ring skeletons represented by formula (2) exist, they may be the same or different.
R 1 represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a hydroxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent. A plurality of R 1s may be the same or different, and R 1s may be bonded to each other to form a ring together with the carbon atom to which R 1 is bonded.
L represents a direct bond, -O-, -S-, -C(R 11 ) 2 -, -N(R 12 )-, an arylene group, or a divalent heterocyclic group.
R 11 represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a hydroxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups may have a substituent. A plurality of R 11s may be the same or different, and R 11s may be bonded to each other to form a ring together with the carbon atom to which R 11 is bonded.
R 12 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. ]

[In the formula,
Ring Ar 4 represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded.
L 1 represents -N(R 1L )-, -S-, -O- or -C(R 2L ) 2 -.
R 1L 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.
R2L represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R 2Ls may be the same or different, and the R 2Ls may be bonded to each other to form a ring together with the carbon atom to which R 2L is bonded.
When the ring skeleton represented by formula (2) is fused with ring Ar 2 , R 1L , R 2L , a substituent that R 1L may have and a substituent that R 2L may have may be bonded to ring Ar 2 , ring Ar 4 , a substituent that ring Ar 2 may have, or a substituent that ring Ar 4 may have to form a ring.
When the ring skeleton represented by formula (2) is fused with ring Ar 3 , R 1L , R 2L , a substituent that R 1L may have and a substituent that R 2L may have may be bonded to ring Ar 3 , ring Ar 4 , a substituent that ring Ar 3 may have, or a substituent that ring Ar 4 may have to form a ring. ]
The compound according to claim 1, which is a compound represented by formula (1-A).

[In the formula,
Ring Ar 2 , ring Ar 3 and R 1 have the same meanings as above.
Ring Ar 1A represents an aromatic hydrocarbon ring or an aromatic heterocycle, and these rings may have a substituent. When a plurality of these substituents exist, they may be bonded to each other to form a ring with the atoms to which they are bonded. ]
The compound according to claim 2, which is a compound represented by formula (1-B).

[In the formula,
R 1 has the same meaning as above.
X represents a carbon atom or a nitrogen atom, and when X is a carbon atom, X is bonded to -R 1X or together with adjacent X formula (1-B1):

Either it combines with the ring skeleton represented by formula (2) to form a ring, or it combines with the ring skeleton represented by formula (2) together with adjacent X to form a ring.
R 1X represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. When a plurality of R 1Xs exist, they may be the same or different, and the R 1Xs may be bonded to each other to form a ring together with the carbon atom to which R 1X is bonded. When X adjacent to X to which R 1X is bonded is bonded to the ring skeleton represented by formula (2), R 1X is R 1L , R 2L in the ring skeleton represented by formula (2). , may be combined with a substituent that R 1L may have or a substituent that R 2L may have to form a ring.
X in formula (1-B1) has the same meaning as above, and may be bonded to -R 1X , or may be bonded to the ring skeleton represented by formula (1-B1) together with adjacent X to further form a ring. may be formed, or may be combined with the ring skeleton represented by formula (2) together with adjacent X to further form a ring.
A plurality of X's may be the same or different.
Y represents a carbon atom or a nitrogen atom, and when Y is a carbon atom, Y is bonded to -R 1Y or together with adjacent Y, formula (1-B2):

Either it combines with the ring skeleton represented by formula (2) to form a ring, or it combines with the ring skeleton represented by formula (2) together with adjacent Y to form a ring.
R 1Y represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. When a plurality of R 1Ys exist, they may be the same or different, and the R 1Ys may be bonded to each other to form a ring together with the carbon atom to which R 1Y is bonded. When Y adjacent to Y to which R 1Y is bonded is bonded to the ring skeleton represented by formula (2), R 1Y is R 1L , R 2L in the ring skeleton represented by formula (2). , may be combined with a substituent that R 1L may have or a substituent that R 2L may have to form a ring.
Y in formula (1-B2) has the same meaning as above, and may be bonded to -R 1Y , or may be bonded to the ring skeleton represented by formula (1-B2) together with adjacent Y to further form a ring. may be formed, or may be bonded to the ring skeleton represented by formula (2) together with adjacent Y to further form a ring.
A plurality of Y's may be the same or different. However, among the combinations of adjacent Y's, at least one pair is bonded to the ring skeleton represented by formula (2) to form a ring. ]
The compound according to any one of claims 1 to 3, wherein the ring skeleton represented by formula (2) is a ring skeleton represented by formula (2-A).

[In the formula,
L 1A represents -N(R 1AL )-, -S-, -O- or -C(R 2AL ) 2 -.
R 1AL 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 2AL represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R 2ALs may be the same or different, and R 2ALs may be bonded to each other to form a ring with the carbon atom to which R 2AL is bonded.
Z represents a carbon atom or a nitrogen atom, and when Z is a carbon atom, Z is bonded to -R 1Z or together with adjacent Z, formula (2-A1):

Either it combines with the ring skeleton represented by to form a ring.
R 1Z represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group; It may have. When a plurality of R 1Ys exist, they may be the same or different, and the R 1Ys may be bonded to each other to form a ring together with the carbon atom to which R 1Y is bonded.
Z in formula (2-A1) has the same meaning as above, and may be bonded to -R 1Z , or may be bonded to the ring skeleton represented by formula (2-A1) together with adjacent Z to further form a ring. may be formed.
A plurality of Z's may be the same or different.
When the ring skeleton represented by formula (2-A) is fused with ring Ar 2 , R 1AL , R 2AL , a substituent that R 1AL may have and R 2AL may have The substituent is bonded to a group on Z located next to two atoms of L 1A or a group on an atom constituting ring Ar 2 located next to two atoms of L 1A to form a ring. Good too.
When the ring skeleton represented by formula (2-A) is fused with ring Ar 3 , R 1AL , R 2AL , a substituent that R 1AL may have and R 2AL may have The substituent is bonded to a group on Z located next to two atoms of L 1A or a group on an atom constituting ring Ar 3 located next to two atoms of L 1A to form a ring. Good too. ]
Formulas (3-A), (3-B), (3-C), (3-D), (3-E), (3-F), (3-G), (3-H), ( The compound according to claim 1, which is a compound represented by 3-I) or (3-J).

[In the formula,
W represents a carbon atom or a nitrogen atom, and when W is a carbon atom, W is bonded to -R 1W or together with the adjacent W formula (3-1):

Either it combines with the ring skeleton represented by to form a ring.
R 1W represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. When a plurality of R 1Xs exist, they may be the same or different, and the R 1Xs may be bonded to each other to form a ring together with the carbon atom to which R 1X is bonded.
R3A represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R 3As may be the same or different, and the R 3As may be bonded to each other to form a ring together with the carbon atom to which R 3A is bonded.
W in formula (3-1) has the same meaning as above, and may be bonded to -R 1W , or may be bonded to the ring skeleton represented by formula (3-1) together with adjacent W to further form a ring. may be formed.
L 3A represents -N(R 31L )-, -S-, -O- or -C(R 32L ) 2 -.
R 31L 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.
R32L represents a hydrogen atom, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, or a substituted amino group, and these groups are substituents. It may have. A plurality of R 32Ls may be the same or different, and the R 32Ls may be bonded to each other to form a ring together with the carbon atom to which R 32L is bonded.
A substituent that R 31L , R 32L , R 31L may have or a substituent that R 32L may have is bonded to a group on W 3A located two atoms adjacent to L 3A to form a ring. You may do so. ]
A polymer compound comprising a structural unit having a group obtained by removing one or more hydrogen atoms from the compound according to claim 1.
The compound according to claim 1 or the polymer compound according to claim 6,
A composition containing at least one member selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a luminescent material, an antioxidant, and a solvent.
comprising an anode, a cathode, and an organic layer provided between the anode and the cathode,
A light emitting device, wherein the organic layer contains the compound according to claim 1 or the polymer compound according to claim 6.