JP7257173B2 - Materials for light-emitting devices and light-emitting devices - Google Patents

Description

TECHNICAL FIELD The present invention relates to a light-emitting device material and a light-emitting device.

Light-emitting elements such as organic electroluminescence elements can be suitably used for displays and lighting applications, and in recent years, research and development of materials for light-emitting elements have been actively carried out. For example, Patent Literature 1 describes the following compound (H0) as a light-emitting element material.

JP 2017-183723 A

However, the light-emitting element described in Patent Document 1 does not necessarily have a sufficient luminance lifetime.
Accordingly, an object of the present invention is to provide a material useful for manufacturing a light-emitting device having excellent luminance life.

The present invention provides the following [1] to [8].

［式（１Ａ）中、ｍは、６以上２０以下の整数を表す。
Ａｒ^１は、単環若しくは縮合環のアリーレン基又は単環若しくは縮合環の２価の複素環基を表し、これらの基は置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
複数存在するＡｒ^１は、同一でも異なっていてもよい。但し、Ａｒ^１の少なくとも一つは、縮合環のアリーレン基又は単環若しくは縮合環の２価の複素環基を表す。］
［２］Ａｒ^１の少なくとも一つが縮合環のアリーレン基（このアリーレン基は置換基を有していてもよい）である、［１］に記載の発光素子用材料。
［３］Ａｒ^１が、単環又は置換基を有していてもよい縮合環のアリーレン基（このアリーレン基は置換基を有していてもよい）である、［１］又は［２］に記載の発光素子用材料。
［４］前記式（１Ａ）で表される化合物が、式（１Ａ－Ａ１）で表される化合物である、［１］～［３］のいずれか一項に記載の発光素子用材料。

［式（１Ａ－Ａ１）中、Ａｒ^２は、縮合環のアリーレン基を表し、前記基は置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
ｎは、５以上１９以下の整数を表す。］
［５］前記縮合環のアリーレン基が、置換基を有していてもよいナフタレンジイル基、置換基を有していてもよいアントラセンジイル基又は置換基を有していてもよいピレンジイル基である、［１］～［４］のいずれか一項に記載の発光素子用材料。
［６］式（ＦＨ－１）で表される化合物及び式(Ｙ)で表される構成単位を含む高分子化合物からなる群より選ばれる少なくとも１種を更に含有する、［１］～［５］のいずれか一項に記載の発光素子用材料。

［式（ＦＨ－１）中、Ａｒ^Ｈ１及びＡｒ^Ｈ２は、それぞれ独立に、アリール基、１価の複素環基又は置換アミノ基を表し、これらの基は置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
ｎ^Ｈ１は、０以上１５以下の整数を表す。
Ｌ^Ｈ１は、アリーレン基、２価の複素環基、又は、－［Ｃ（Ｒ^Ｈ１１）_２］－で表される基を表し、これらの基は置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。Ｌ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。Ｒ^Ｈ１１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。複数存在するＲ^Ｈ１１は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。］

［式（Ｙ）中、Ａｒ^Ｙ１は、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。］
［７］正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料、酸化防止剤及び溶媒からなる群より選ばれる少なくとも１種を更に含有する、［１］～［６］のいずれかに記載の発光素子用材料。
［８］［１］～［７］のいずれかに記載の発光素子用材料を含有する発光素子。 [1] A light-emitting device material containing a compound represented by formula (1A).

[In formula (1A), m represents an integer of 6 or more and 20 or less.
Ar ¹ represents a monocyclic or condensed-ring arylene group or a monocyclic or condensed-ring divalent heterocyclic group, and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
A plurality of Ar ¹ may be the same or different. However, at least one of Ar ¹ represents a condensed-ring arylene group or a monocyclic or condensed-ring divalent heterocyclic group. ]
[2] The light-emitting device material according to [1], wherein at least one of Ar ¹ is a condensed ring arylene group (this arylene group may have a substituent).
[3] in [1] or [2], wherein Ar ¹ is a monocyclic or optionally substituted condensed ring arylene group (the arylene group may have a substituent); The material for a light-emitting device described above.
[4] The light-emitting element material according to any one of [1] to [3], wherein the compound represented by formula (1A) is a compound represented by formula (1A-A1).

[In the formula (1A-A1), Ar ² represents a condensed ring arylene group, and said group may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
n represents an integer of 5 or more and 19 or less. ]
[5] The arylene group of the condensed ring is a naphthalene diyl group optionally having a substituent, an anthracenediyl group optionally having a substituent or a pyrenediyl group optionally having a substituent , the material for a light-emitting device according to any one of [1] to [4].
[6] Further containing at least one selected from the group consisting of a compound represented by formula (FH-1) and a polymer compound containing a structural unit represented by formula (Y) [1] to [5] ] The material for a light-emitting device according to any one of .

[In formula (FH-1), Ar ^{1 H1} and Ar ^{2 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 the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
n ^H1 represents an integer of 0 or more and 15 or less.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by -[C(R ^H11 ) ₂ ]-, and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When multiple ^LH1 are present, they may be the same or different. R ^H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. A plurality of ^RH11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[In the formula (Y), 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. and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
[7] Further containing at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent, [1] to [6] The light emitting device material according to any one of .
[8] A light-emitting device containing the light-emitting device material according to any one of [1] to [7].

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a material useful for manufacturing a light-emitting device having excellent luminance lifetime. Further, according to the present invention, it is possible to provide a light-emitting device containing the above material.

1A and 1B are schematic cross-sectional views of a light-emitting element in one embodiment of the present invention.

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

<Description of common terms>
Terms commonly used in this specification have the following meanings unless otherwise specified.
Me is a methyl group, Et is an ethyl group, Bu is a butyl group, i-Pr is an isopropyl group, and t-Bu is a tert-butyl group.

A hydrogen atom may be a deuterium atom or a protium atom.

In the formulas representing metal complexes, solid lines representing bonds between ligands and metals mean ionic bonds, covalent bonds or coordinate bonds.

A “polymer compound” means a polymer having a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1×10 ³ to 1×10 ⁸ .

The polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, or a graft copolymer, or may be in other forms.

When the terminal group of the polymer compound is a polymerization active group such as the group A group of substituents described below and the group B group of substituents described below, when the polymer compound is used to manufacture a light-emitting device, the light-emitting property or luminance lifetime is reduced. there's a possibility that. Therefore, the terminal group of the polymer compound is preferably a stable group. Stable groups include, for example, aryl groups or monovalent heterocyclic groups that are attached through a carbon-carbon bond to the backbone of the polymeric compound.

A "low-molecular-weight compound" means a compound having no molecular weight distribution and a molecular weight of 1×10 ⁴ or less.

A "structural unit" means an atomic group that exists in two or more units in a polymer compound.

The "alkyl group" may be either linear or branched. The number of carbon atoms in the linear alkyl group is generally 1-50, preferably 3-30, more preferably 4-20, not including the number of carbon atoms in the substituents. The number of carbon atoms in the branched alkyl group is generally 3-50, preferably 3-30, more preferably 4-20, not including the number of carbon atoms in the substituent.

The alkyl group may have a substituent, for example, 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, heptyl group, octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group , and groups in which hydrogen atoms in these groups are substituted with cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc. (e.g., trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group , perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3-(4-methylphenyl)propyl group, 3-(3,5-di-hexylphenyl)propyl group, 6-ethyloxyhexyl group) is mentioned.

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

A cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a methylcyclohexyl group, and an ethylcyclohexyl group.

An "aryl group" means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in the aryl group is generally 6-60, preferably 6-20, more preferably 6-10, not including the number of carbon atoms in the substituents.

The aryl group may have a substituent, for example, a 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 hydrogen atoms in these groups includes groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

An "alkoxy group" may be either linear or branched. The straight-chain alkoxy group usually has 1 to 40 carbon atoms, preferably 4 to 10 carbon atoms, not including the carbon atoms of the substituents. The number of carbon atoms in the branched alkoxy group is usually 3-40, preferably 4-10, not including the number of carbon atoms in the substituents.

The alkoxy group may have a substituent, for example, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, A heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, a lauryloxy group, and hydrogen atoms in these groups are cycloalkyl groups, alkoxy groups, A cycloalkoxy group, an aryl group, a group substituted with a fluorine atom or the like can be mentioned.

The number of carbon atoms in the "cycloalkoxy group" is usually 3-40, preferably 4-10, not including the number of carbon atoms in the substituents.

A cycloalkoxy group may have a substituent, such as a cyclohexyloxy group.

The number of carbon atoms in the "aryloxy group" is usually 6-60, preferably 6-48, not including the number of carbon atoms in the substituents.

The aryloxy group may have a substituent, for example, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Pyrenyloxy groups and groups in which hydrogen atoms in these groups are substituted with alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, fluorine atoms and the like are included.

A "p-valent heterocyclic group" (p represents an integer of 1 or more) refers to, from a heterocyclic compound, p hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring. means the remaining atomic groups excluding the hydrogen atoms of Among p-valent heterocyclic groups, it is an atomic group remaining after removing p hydrogen atoms among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A "p-valent aromatic heterocyclic group" is preferred.

“Aromatic heterocyclic compounds” include heterocyclic compounds such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, and dibenzophosphole. Compounds in which the ring itself exhibits aromaticity, and heterocycles such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilole, benzopyran, etc., in which an aromatic ring is condensed even if the heterocycle itself does not exhibit aromaticity means a compound.

The number of carbon atoms in the monovalent heterocyclic group is usually 2-60, preferably 4-20, not including the number of carbon atoms in the substituents.
The monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these and a group in which a hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.

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

The "amino group" may have a substituent, preferably a substituted amino group. As the substituent of the amino group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferable.

Substituted amino groups include, for example, dialkylamino groups, dicycloalkylamino groups and diarylamino groups.
Examples of amino groups include dimethylamino group, diethylamino group, diphenylamino group, bis(4-methylphenyl)amino group, bis(4-tert-butylphenyl)amino group, bis(3,5-di-tert- butylphenyl)amino group.

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

The number of carbon atoms in the "cycloalkenyl group" is usually 3-30, preferably 4-20, not including the number of carbon atoms in the substituents.

Alkenyl groups and cycloalkenyl groups may have substituents, for example, vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4- Pentenyl group, 1-hexenyl group, 5-hexenyl group, 7-octenyl group, and groups in which these groups have substituents.

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

The number of carbon atoms in the "cycloalkynyl group" is usually 4-30, preferably 4-20, not including the carbon atoms of the substituents.

Alkynyl groups and cycloalkynyl groups may have substituents, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4- A pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and groups in which these groups have substituents are included.

An "arylene group" means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in the arylene group is usually 6-60, preferably 6-30, more preferably 6-18, not including the number of carbon atoms in the substituent.

The arylene group may have a substituent, for example, a phenylene group, a biphenyldiyl group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthacenediyl group, a fluorenediyl group, and a pyrenediyl group. , a perylenediyl group, a chrysenediyl group, and groups in which these groups have substituents, preferably groups represented by formulas (A-1) to (A-20). The arylene group includes groups in which multiple of these groups are bonded.

［式中、Ｒ及びＲ^aは、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表す。複数存在するＲ及びＲ^aは、各々、同一でも異なっていてもよく、Ｒ^a同士は互いに結合して、それぞれが結合する原子と共に環を形成していてもよい。］

[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 together with the atoms to which they are bonded. ]

The number of carbon atoms in the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, more preferably 4 to 15, not including the number of carbon atoms in the substituents.

The divalent heterocyclic group may have a substituent, such as pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, and triazole, preferably a divalent group excluding two hydrogen atoms among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring. is a group represented by formulas (AA-1) to (AA-34). Divalent heterocyclic groups include groups in which multiple of these groups are bonded.

［式中、Ｒ及びＲ^ａは、前記Ｒ及びＲ^ａと同じ意味を表す。］

[In the formula, R and ^Ra have the same meaning as the above R and ^Ra . ]

The “crosslinking group” is a group capable of forming a new bond by subjecting it to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, or the like. It is a group represented by any one of formulas (B-1) to (B-17). These groups may have a substituent.

"Substituent" means a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, an alkenyl group. , represents a cycloalkenyl group, an alkynyl group or a cycloalkynyl group, and these groups may further have a substituent. A substituent may be a bridging group. When a plurality of substituents are present, they may bond with each other to form a ring together with the atoms to which they are bonded, but preferably do not form a ring. In the present specification, when a group is described as optionally having a substituent, it means that the group may have at least one of the above "substituents".

<Compound Represented by Formula (1A)>
The light-emitting element material of the present invention is a light-emitting element material containing the compound represented by the formula (1A). In the light-emitting device material of the present invention, the compound represented by Formula (1A) may contain only one type, or may contain two or more types.

The number of carbon atoms in the monocyclic arylene group for Ar ¹ is preferably 6, not including the number of carbon atoms in the substituent. The monocyclic arylene group for Ar ¹ is preferably a phenylene group and may have a substituent. The monocyclic arylene group for Ar ¹ is more preferably a group represented by formulas (A-1) to (A-3), still more preferably a group represented by formula (A-1) is.

The number of carbon atoms in the condensed ring arylene group for Ar ¹ is usually 7 to 60, not including the number of carbon atoms in the substituents. The condensed ring arylene group in Ar ¹ preferably has 8 to 20 carbon atoms. Examples of the condensed ring arylene group for Ar ¹ include naphthalenediyl, anthracenediyl, phenanthenediyl, dihydrophenanthenediyl, naphthacenediyl, fluorenediyl, spirobifluorenediyl, pyrenediyl, and perylenediyl groups. and chrysenediyl groups. The condensed ring arylene group in Ar ¹ is preferably a naphthalenediyl group, anthracenediyl group or a pyrenediyl group, more preferably a naphthalenediyl group, and particularly preferably represented by formula (A-5). and these groups may have a substituent.

The number of carbon atoms in the monocyclic divalent heterocyclic group for Ar ¹ is preferably 2 to 5, not including the number of carbon atoms in the substituents. A monocyclic divalent heterocyclic group for Ar ¹ is, for example, pyridine, diazabenzene, triazine, furan, thiophene, azole, diazole or triazole, and a hydrogen atom directly bonded to a ring-constituting carbon atom or heteroatom. and divalent groups excluding two hydrogen atoms. These groups may have a substituent.

The number of carbon atoms in the condensed divalent heterocyclic group in Ar ¹ is usually 2 to 60, not including the number of carbon atoms in the substituent. The condensed-ring divalent heterocyclic group for Ar ¹ includes, for example, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine or dihydroacridine, and carbon atoms constituting the ring. Divalent groups excluding two hydrogen atoms among hydrogen atoms directly bonded to atoms or heteroatoms are included. These groups may have a substituent.

The substituent that Ar ¹ may have is preferably a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group. These groups may further have a substituent.

Since the synthesis of the compound represented by the formula (1A) is facilitated, when there are multiple substituents that Ar ¹ may have, they should not be bonded to each other to form a ring together with the atoms to which they are bonded. is preferred.

Ar ¹ is preferably a monocyclic or condensed ring arylene group, and this group may have a substituent, since this facilitates the synthesis of the compound represented by formula (1A).
Since a light-emitting device containing the light-emitting device material of the present invention (hereinafter also referred to as "the light-emitting device of the present invention") has superior luminance life, at least one of Ar ¹ is preferably a condensed ring arylene group. Preferably, 1 to 5 of Ar ¹ are condensed ring arylene groups, more preferably 1 of Ar ¹ is a condensed ring arylene group, and these groups have a substituent. may

m is preferably 7 or more and 15 or less, more preferably 8 or more and 13 or less, still more preferably 10 or more and 12 or less, because it facilitates the synthesis of the compound represented by formula (1A). be.

[Compounds Represented by Formula (1A-A1) and Formula (1A-A2)]
The compound represented by the formula (1A) is preferably the compound represented by the formula (1A-A1) because the light-emitting device of the present invention has a more excellent luminance lifetime.

Examples and preferred ranges of the condensed-ring arylene group for Ar ² are the same as the examples and preferred ranges for the condensed-ring arylene group for Ar ¹ .
n is preferably 6 or more and 14 or less, more preferably 7 or more and 12 or less, still more preferably 9 or more and 11 or less, because it facilitates the synthesis of the compound represented by formula (1A). be.
Examples and preferred ranges of substituents that the phenylene group in formula (1A-A1) may have are the same as examples and preferred ranges of substituents that Ar ¹ may have.

The compound represented by the formula (1A-A1) is preferably the compound represented by the formula (1A-A2), since the light-emitting device of the present invention has a more excellent luminance lifetime.

［式中、Ａｒ^２及びｎは、前記Ａｒ^２及びｎと同じ意味を表す。式中の１，４－フェニレン基は、置換基を有していてもよい。前記置換基が複数存在する場合、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[In the formula, Ar ² and n have the same meaning as Ar ² and n above. The 1,4-phenylene group in the formula may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

Examples and preferred ranges of substituents optionally possessed by the 1,4-phenylene group in formula (1A-A2) are the same as examples and preferred ranges of substituents optionally possessed by Ar ¹ . .

Examples of the compound represented by formula (1A) include compounds represented by formulas (1A-01) to (1A-33).

<Method for Producing Compound Represented by Formula (1A)>
For example, the compound represented by formula (1A) can be obtained by, for example, combining a compound represented by formula (M-1) and a compound represented by formula (M-2) using a known coupling reaction. It can be synthesized by reacting.

Known coupling reactions include, for example, coupling reactions using transition metal catalysts such as Suzuki reaction, Stille reaction, Negishi reaction and Kumada reaction.

［式中、ｍ′及びｎ′は、それぞれ独立に、１以上１９以下の整数を表す。但し、ｍ′とｎ′との合計は、６以上２０以下の整数である。
Ａｒ^ａ及びＡｒ^ｂは、それぞれ独立に、単環若しくは縮合環のアリーレン基、単環若しくは縮合環の２価の複素環基、又はシクロアルカジエンが有する２つのｓｐ^３炭素原子から水素原子を１個ずつ除いた基を表し、これらの基は置換基を有していてもよい。前記置換基が複数存在する場合、それらは互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、Ａｒ^ｂの少なくとも一つは、縮合環のアリーレン基又は単環若しくは縮合環の２価の複素環基を表す。複数のＡｒ^ａ及びＡｒ^ｂは、それぞれ同一でも異なっていてもよい。
Ｚ^１及びＺ^２は、それぞれ独立に、置換基Ａ群及び置換基Ｂ群からなる群から選ばれる基を表す。複数存在するＺ^１は、同一でも異なっていてもよい。複数存在するＺ^２は、同一でも異なっていてもよい。］

[In the formula, m' and n' each independently represent an integer of 1 or more and 19 or less. However, the sum of m' and n' is an integer of 6 or more and 20 or less.
Ar ^a and Ar ^b are each independently a monocyclic or condensed ring arylene group, a monocyclic or condensed ring divalent heterocyclic group, or two sp ³ carbon atoms possessed by cycloalkadiene to which one hydrogen atom is It represents groups that are removed one by one, and these groups may have a substituent. When there are multiple substituents, they may be bonded together to form a ring together with the atoms to which they are bonded. However, at least one of ^Arb represents a condensed-ring arylene group or a monocyclic or condensed-ring divalent heterocyclic group. A plurality of Ar ^a and Ar ^b may be the same or different.
Z ¹ and Z ² each independently represent a group selected from the group consisting of substituent group A and substituent group B; A plurality of Z ¹ may be the same or different. A plurality of Z ² may be the same or different. ]

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

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

For example, when Z ¹ is a group selected from Substituent Group A, Z ² selects a group selected from Substituent Group B. For example, when Z ¹ is a group selected from Substituent Group B, Z ² selects a group selected from Substituent Group A.

A group selected from Substituent Group A is preferably a bromine atom, an iodine atom or a group represented by —OS(=O) ₂ R ^C1 , more preferably a bromine atom.
A group selected from Substituent Group B is preferably a group represented by -B(OR ^C2 ) ₂ .

The group represented by -B(OR ^C2 ) ₂ includes, for example, groups represented by formulas (W-1) to (W-10).

Regarding the more detailed production method of the compound represented by formula (1A), the compound (M -1-3) will be described as an example. The compound represented by formula (M-1-3) can be obtained, for example, by using the compound represented by formula (M-1-1) and the compound represented by formula (M-2) in the following scheme can be synthesized with

［式中、Ａｒ^ｂ、Ｚ^１及びＺ^２は、それぞれ前記Ａｒ^ｂ、Ｚ^１及びＺ^２と同じ意味を表す。Ｒ^Ａは、水酸基、アルコキシ基、シクロアルコキシ基又はアリールオキシ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ａは、同一でも異なっていてもよい。ｎ′′は、１以上１１以下の整数を表す。］

[In the formula, Ar ^b , Z ¹ and Z ² have the same meanings as the above Ar ^b , Z ¹ and Z ² respectively. ^RA represents a hydroxyl group, an alkoxy group, a cycloalkoxy group or an aryloxy group, and these groups may have a substituent. Multiple ^RAs may be the same or different. n'' represents an integer of 1 or more and 11 or less. ]

R ^A is preferably a hydroxyl group or an alkoxy group, more preferably an alkoxy group, since it is easy to synthesize, and these groups may have a substituent.

(Step A)
In step A, the compound represented by formula (M-1-1) is, for example, J. Org. Chem. Chem. Soc. 2011, 133, 15800-15802 (hereinafter also referred to as “Non-Patent Document 2”) and the like.

In step A, the amount of the compound represented by formula (M-2) used is preferably 0.8 to 2.0% relative to the total substance amount of the compound represented by formula (M-1-1). 0 molar equivalents.

Step A preferably employs a coupling reaction using a transition metal catalyst. More specifically, in step A, the compound represented by formula (M-1-2) is combined with the compound represented by formula (M-1-1) in the presence of a transition metal complex, a base and a solvent. It can be synthesized by a coupling reaction with the compound represented by (M-2).

In step A, the transition metal complex is preferably a palladium complex. Palladium complexes include, for example, [tris(dibenzylideneacetone)]dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(triphenylphosphine)palladium, dichlorobis(tris-o-methoxyphenylphosphine)palladium, palladium chloride, acetic acid Palladium, bis(benzonitrile)dichloropalladium, and [tetrakis(triphenylphosphine)]palladium.
The amount of transition metal complex to be used is preferably 0.00001 to 3 molar equivalents relative to the total amount of substances of the compound represented by formula (M-1-1). A transition metal complex may be used individually by 1 type, or may use 2 or more types together.

In step A, the transition metal complex may be used by being mixed with a ligand such as a phosphine ligand. Phosphine ligands include, for example, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, (4-dimethylaminophenyl) Di-tert-butylphosphine, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)-2'-(dimethylamino)biphenyl, dicyclohexyl (2',4',6'-triisopropyl -3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine, 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl, triphenylphosphine, tri-o-tolylphosphine, Tri-tert-butylphosphine, tricyclohexylphosphine, and di-tert-butylphenylphosphine.

In step A, the amount of the ligand used is preferably 0.5 to 20 molar equivalents relative to the amount of the transition metal complex. A ligand may be used individually by 1 type, or may use 2 or more types together.

In step A, examples of the base include sodium carbonate, potassium hydroxide, sodium hydroxide, potassium carbonate, cesium carbonate, potassium phosphate, sodium tert-butoxide, lithium tert-butoxide, potassium tert-butoxide, tetrabutylammonium hydroxy tetraethylammonium hydroxide, and tetramethylammonium hydroxide.

The amount of the base to be used is preferably 0.1 to 30 molar equivalents relative to the total amount of substances of the compound represented by the formula (M-1-1). A base may be used individually by 1 type, or may be used in combination of 2 or more types.

In step A, the solvent includes, for example, alcoholic solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol and 2-ethoxyethanol; diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether and ether solvents such as 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; Amide solvents such as N,N-dimethylacetamide; acetone, dimethylsulfoxide, and water.
The amount of the solvent to be used is preferably 1 to 2000 parts by mass with respect to 1 part by mass of the compound represented by formula (M-1-1). A solvent may be used individually by 1 type, or may use 2 or more types together.

In step A, the reaction temperature is preferably 0°C to 200°C.
In step A, the reaction time is preferably 0.5 to 24 hours.

(Step B)
In step B, the compound represented by formula (M-1-3) can be synthesized by aromatizing the compound represented by formula (M-1-2). More specifically, the compound represented by formula (M-1-3) can be synthesized by converting the cyclohexadienyl skeleton portion in the compound represented by formula (M-1-2) to a benzene ring. .

As a method for aromatizing the compound represented by formula (M-1-2), for example, a method of carrying out a reduction reaction and then carrying out an oxidation reaction can be mentioned. For example, by using a reducing agent, ^RA is first eliminated and the hydrogenation reaction proceeds. After that, by performing an oxidation treatment, the cyclohexadienyl skeleton portion is converted to a benzene ring.
In the step B, as the reduction reaction, for example, by using a reducing agent, ^RA is first eliminated, and the dehydrogenation reaction proceeds. By subsequently performing an oxidation treatment, the cyclohexadienyl ring portion is converted to a benzene ring.

In step B, the reducing agent includes sodium naphthalenide, lithium naphthalenide, and the like.

In step B, the amount of the reducing agent to be used is generally preferably 1 to 500 molar equivalents relative to the total amount of substances of the compound represented by formula (M-1-3).

In step B, the reduction reaction is preferably carried out in a solvent. Examples and preferred ranges of solvents in step B are the same as examples and preferred ranges of solvents in step A. A solvent may be used individually by 1 type, or may use 2 or more types together.

In step B, the amount of the solvent to be used is generally 1 to 1000 parts by mass based on 1 part by mass of the compound represented by the formula (M-1-3).

In step B, the reaction temperature for the reduction reaction is in the range of -100°C to 0°C.
In step B, the reaction time for the reduction reaction is 0.5 to 24 hours.

In step B, the oxidizing agent includes chloranil, o-chloranil, and quinones such as 2,3-dichloro-5,6-dicyano-p-benzoquinone, iodine, and the like.

In step B, the amount of the oxidizing agent to be used is generally preferably 1 to 500 molar equivalents relative to the total amount of the compounds represented by formula (1-1-3).

In step B, the oxidation reaction is preferably carried out in a solvent. Examples and preferred ranges of solvents in step B are the same as examples and preferred ranges of solvents in step A. A solvent may be used individually by 1 type, or may use 2 or more types together.

In step B, the amount of the solvent to be used is generally 1 to 1000 parts by mass based on 1 part by mass of the compound represented by the formula (1-1-3).

In step B, the reaction temperature for the oxidation reaction is in the range of -100°C to 0°C.
In step B, the reaction time of the oxidation reaction is 0.5-24 hours.

The compounds, catalysts and solvents used in the respective reactions described in <Method for Producing Compound Represented by Formula (1A)> may be used singly or in combination of two or more.

<Host material>
Since the light-emitting device of the present invention has a more excellent luminance lifetime, the material for a light-emitting device of the present invention includes the compound represented by formula (1A) and the hole-injecting, hole-transporting, electron-injecting and electron-transporting properties and a host material having at least one function selected from the group consisting of (hereinafter also referred to as "composition 1"). In composition 1, the host material may contain only one type, or may contain two or more types.
In composition 1, the content of the compound represented by formula (1A) is usually 0.01 to 99 parts by mass when the total of the compound represented by formula (1A) and the host material is 100 parts by mass. parts, preferably 0.1 to 50 parts by mass, more preferably 0.5 to 25 parts by mass, still more preferably 1 to 10 parts by mass.

In composition 1, the lowest excited singlet state (S ₁ ) possessed by the host material has an energy equivalent to S ₁ possessed by the compound represented by formula (1A), since the light-emitting device of the present invention has a superior luminance lifetime. levels or higher energy levels.

In composition 1, the host material is soluble in a solvent capable of dissolving the compound represented by formula (1A), since the light-emitting device of the present invention can be produced by a wet method. is preferred.

Host materials are classified into low-molecular-weight compounds and high-molecular-weight compounds. Examples of the host material include a hole-transporting material described later and an electron-transporting material described later.

• Low-molecular-weight host A low-molecular-weight compound (hereinafter referred to as "low-molecular-weight host") preferable as a host material is, for example, a compound represented by the formula (FH-1).

Ar ^H1 and Ar ^H2 are preferably aryl groups, and these groups may have substituents.

The number of carbon atoms in the aryl group in Ar ^{1 H1} and Ar ^{2 H2} is usually 6-60, preferably 6-14, not including the number of carbon atoms in the substituents.

The aryl group for Ar ^H1 and Ar ^H2 includes a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, A group formed by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from an indene ring, a fluoranthene ring or a benzofluoranthene ring. The aryl group in Ar ^{1 H1} and Ar ^{2 H2} is more preferably a phenyl group, a naphthyl group or an anthracenyl group, still more preferably a phenyl group or a naphthyl group. These groups may further have a substituent.

The number of carbon atoms in the monovalent heterocyclic group in Ar ^{1 H1} and Ar ^{2 H2} is usually 2 to 60, not including the number of carbon atoms in the substituent.

Examples of monovalent heterocyclic groups for Ar ^H1 and Ar ^H2 include pyrrole ring, diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, and indole. ring, benzodiazole ring, benzotriazole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring , phenazine ring and 5,10-dihydrophenazine ring, from which one hydrogen atom directly bonded to a carbon atom or heteroatom constituting the ring is removed. These groups may further have a substituent.

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

Preferred substituents that Ar ^H1 and Ar ^H2 may have are an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, and a substituted amino group. group or halogen atom, and these groups may further have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents that Ar ^H1 and Ar ^H2 may have are the aryl group and monovalent heterocyclic group in Ar ^H1 and Ar ^H2 , respectively. It is the same as the examples and preferred ranges of the cyclic group and the substituted amino group.

Preferred substituents that the substituents Ar ^H1 and Ar ^H2 may further have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, It is a cycloalkoxy group, an aryloxy group, a substituted amino group or a halogen atom, and these groups may further have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the substituents which the substituents which Ar ^H1 and Ar ^H2 may further have are respectively Ar ^H1 and The same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in Ar ^H2 .

^nH1 is preferably an integer of 1 or more and 5 or less, and more preferably an integer of 1 or more and 3 or less.

L ^H1 is preferably an arylene group, and this group may have a substituent.

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

The arylene group in L ^H1 is preferably a group represented by formulas (A-1) to (A-14) or formulas (A-17) to (A-20), more preferably the formula (A-1) to a group represented by formula (A-6), formula (A-11) or formula (A-12).

The divalent heterocyclic group in L ^H1 is preferably represented by formulas (AA-1) to (AA-6), formulas (AA-10) to formulas (AA-22), or formulas (AA-24) to formulas It is a group represented by (AA-34).

R ^H11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

Examples and preferred ranges of substituents that R ^{1 H11} may have are the same as examples and preferred ranges of substituents that Ar ^{1 H1} and Ar ^{2 H2} may have.

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

-Polymer host A polymer compound (hereinafter referred to as "polymer host") preferable as a host material is, for example, a polymer compound containing a constitutional unit represented by the above formula (Y).

The arylene group represented by Ar ^Y1 is more preferably represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11), formula ( A-13) or a group represented by formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9), formula (A-11) or It is a group represented by formula (A-19), and these groups may have a substituent.

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

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

Examples of divalent groups in which at least one arylene group and at least one divalent heterocyclic group represented by Ar ^Y1 are directly bonded are represented by Ar ^X2 and Ar ^X4 in formula (X) below. is the same as an example of a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded.

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

Examples of structural units represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-8).

The polymer host preferably contains a structural unit represented by formula (Y-2) and/or a structural unit represented by formula (Y-8), since the light-emitting device of the present invention has a more excellent luminance lifetime. It is a polymer compound.

［式中、Ｒ^Ｙ１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲY1は、同一でも異なっていてもよく、Ｒ^Ｙ１同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[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 RY1's may be the same or different, and ^RY1 's may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

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

［式中、Ｒ^Ｙ１１は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ１１は、同一でも異なっていてもよい。］

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

［式中、Ｒ^Ｙ１は前記Ｒ^Ｙ１と同じ意味を表す。
Ｘ^Ｙ１は、－Ｃ（Ｒ^Ｙ２）_２－、－Ｃ（Ｒ^Ｙ２）＝Ｃ（Ｒ^Ｙ２）－又は－Ｃ（Ｒ^Ｙ２）_２－Ｃ（Ｒ^Ｙ２）_２－で表される基を表す。Ｒ^Ｙ２は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ２は、同一でも異なっていてもよく、Ｒ^Ｙ２同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[In the formula, R ^Y1 has the same meaning as R ^Y1 described above.
X ^Y1 represents a group represented by -C(R ^Y2 ) ₂ -, -C(R ^Y2 )=C(R ^Y2 )- or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -. ^RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY2 may be the same or different, and the ^RY2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

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

In X ^Y1 , the combination of two R ^Y2 in the group represented by —C(R ^Y2 ) ₂ — is preferably both an alkyl group or a cycloalkyl group, both an aryl group, and both a monovalent a cyclic group, or one of which is an alkyl group or cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group. A combination of two R ^Y2 in the group represented by -C(R ^Y2 ) ₂ - is more preferably one of an alkyl group or a cycloalkyl group and the other an aryl group. These groups may have a substituent. Two R ^Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded. When R ^Y2 forms a ring, the group represented by —C(R ^Y2 ) ₂ — is preferably a group represented by formulas (Y-A1) to (Y-A5), more preferably is a group represented by the formula (YA4). These groups may have a substituent.

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

［式中、Ｒ^Ｙ１及びＸ^Ｙ１は前記Ｒ^Ｙ１及びＸ^Ｙ１と同じ意味を表す。］

[In the formula, R ^Y1 and X ^Y1 have the same meaning as the above R ^Y1 and X ^Y1 . ]

［式中、Ｒ^Ｙ１は前記Ｒ^Ｙ１と同じ意味を表す。Ｒ^Ｙ３は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, R ^Y1 has the same meaning as R ^Y1 described above. ^RY3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

［式中、Ｒ^Ｙ１は前記Ｒ^Ｙ１と同じ意味を表す。Ｒ^Ｙ４は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, R ^Y1 has the same meaning as R ^Y1 described above. ^RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

［式中、Ｒ^Ｙ１は前記Ｒ^Ｙ１と同じ意味を表す。］

[In the formula, R ^Y1 has the same meaning as R ^Y1 described above. ]

Examples of structural units represented by formula (Y) include structural units represented by formulas (Y-11) to (Y-56).

In the structural unit represented by formula (Y), when Ar ^{2 Y1} is an arylene group, the luminance life of the light-emitting device of the present invention is superior. It is preferably 10 to 100 mol %, more preferably 50 to 100 mol %, relative to the total amount of the constituent units contained.

Structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or a divalent in which at least one arylene group and at least one divalent heterocyclic group are directly bonded Since the polymer host has an excellent charge transport property, the structural unit which is a group of is preferably 0.5 to 40 mol % with respect to the total amount of the structural units contained in the polymer host.

The structural unit represented by the formula (Y) may be contained in the polymer host alone or in combination of two or more.

Since the polymer host has excellent hole-transporting properties, it preferably further contains a structural unit represented by the following formula (X).

［式（Ｘ）中、ａ^X1およびａ^X2は、それぞれ独立に、０以上の整数を表す。
Ａｒ^X1およびＡｒ^X3は、それぞれ独立に、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^X2およびＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、または、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2およびＡｒ^X4が複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^X1、Ｒ^X2およびＲ^X3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^X2およびＲ^X3が複数存在する場合、それらは同一でも異なっていてもよい。］

[In formula (X), a ^X1 and a ^X2 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; and these groups may have a substituent. When multiple Ar ^X2 and Ar ^X4 are present, they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple R ^X2 and R ^X3 are present, they may be the same or different. ]

a ^X1 and a ^X2 are preferably 0 because the light-emitting device of the present invention has superior luminance lifetime.

R ^X1 , R ^X2 and R ^X3 are preferably aryl groups, and these groups may have substituents.

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

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

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

Examples of the divalent group in which at least one arylene group and at least one divalent heterocyclic group represented by Ar ^X2 and Ar ^X4 are directly bonded include groups represented by the following formulae. , these may have a substituent.

［式中、Ｒ^ＸＸは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

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

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

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

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

The structural unit represented by formula (X) is preferably a structural unit represented by formula (X-1) to formula (X-7), more preferably represented by formula (X-1) It is a building block.

［式中、Ｒ^Ｘ４及びＲ^Ｘ５は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、ハロゲン原子、１価の複素環基又はシアノ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｘ４は、同一でも異なっていてもよい。複数存在するＲ^Ｘ５は、同一でも異なっていてもよく、隣接するＲ^Ｘ５同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

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

Since the structural unit represented by the formula (X) has excellent hole-transporting properties, it is preferably 0.1 to 50 mol%, more preferably It is 1 to 40 mol %, more preferably 5 to 30 mol %.

Examples of structural units represented by formula (X) include structural units represented by formulas (X1-1) to (X1-19).

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

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

［表中、ｐ、ｑ、ｒ、ｓ及びｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝１００であり、かつ、１００≧ｐ＋ｑ＋ｒ＋ｓ≧７０である。］

[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, or a graft copolymer, or may be in some other form. It is preferably a copolymer obtained by copolymerization.

The polystyrene equivalent number average molecular weight of the polymer host is preferably 5×10 ³ to 1×10 ⁶ , more preferably 1×10 ⁴ to 5×10 ⁵ , and more preferably 1.5×10 ^{4 .} ˜2×10 ⁵ .

Polymer hosts can be produced using known polymerization methods described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), Suzuki reaction, Yamamoto reaction, Buchwald reaction. Examples include a method of polymerization by a coupling reaction using a transition metal catalyst, such as reaction, Stille reaction, Negishi reaction, and Kumada reaction.

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

Polymer compounds include, for example, polyvinylcarbazole and derivatives thereof; polyarylenes and derivatives thereof having aromatic amine structures in side chains or main chains. A polymer compound may be a compound having an electron-accepting site attached thereto. Examples of electron-accepting moieties include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone.

In the composition of the present invention, the compounding amount of the hole transport material is usually 1 to 400 parts by mass with respect to 100 parts by mass of the compound represented by formula (1A).

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

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

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

Polymer compounds include, for example, polyphenylene, polyfluorene, and derivatives thereof. The polymeric compounds may be doped with metals.

In the composition of the present invention, the amount of the electron-transporting material is usually 1 to 400 parts by mass per 100 parts by mass of the compound represented by formula (1A).

The electron transport materials may be used singly or in combination of two or more.

[Hole injection material and electron injection material]
Hole-injecting materials and electron-injecting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds, respectively. The hole-injecting material and the electron-injecting material may have cross-linking groups.

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

Polymer compounds include, for example, polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain; and a flexible polymer.

In the composition of the present invention, the amount of each of the hole injection material and the electron injection material is usually 1 to 400 parts by mass per 100 parts by mass of the metal complex of the present invention.

Each of the hole injection material and the electron injection material may be used alone or in combination of two or more.

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

The type of ions to be doped is an anion for a hole-injection material, and a cation for an electron-injection material. Anions include, for example, polystyrene sulfonate, alkylbenzene sulfonate, and camphor sulfonate. Cations include, for example, lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

Ions for doping may be used alone or in combination of two or more.

[Light emitting material]
Light-emitting materials (different from compounds represented by formula (1A)) are classified into low-molecular-weight compounds and high-molecular-weight compounds. The luminescent material may have a cross-linking group.

Low-molecular-weight compounds include, for example, naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triplet emission complexes with iridium, platinum, or europium as the central metal.

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

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

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

In the composition of the present invention, the content of the luminescent material is usually 0.1 to 400 parts by mass with respect to 100 parts by mass of the compound represented by formula (1A).

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the compound represented by formula (1A) of the present invention and does not inhibit light emission and charge transport. Inhibitors are included.

In the composition of the present invention, the amount of the antioxidant compounded is usually 0.001 to 10 parts by mass per 100 parts by mass of the compound represented by formula (1A).

Antioxidants may be used singly or in combination of two or more.

The composition containing the compound represented by the formula (1A) of the present invention and a solvent (hereinafter referred to as "ink") can be used in the production of light-emitting elements using a printing method such as an inkjet printing method or a nozzle printing method. preferred.

The viscosity of the ink may be adjusted according to the type of printing method. It is preferably 1 to 20 mPa·s at 25°C.

The solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of solvents include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole, and 4-methylanisole; Aromatic hydrocarbon solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, and cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane , n-decane, n-dodecane, and bicyclohexyl aliphatic hydrocarbon solvents; acetone, methyl ethyl ketone, cyclohexanone, and acetophenone ketone solvents; ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and ester solvents such as 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; Amide solvents such as methyl-2-pyrrolidone and N,N-dimethylformamide are included. A solvent may be used individually by 1 type, or may use 2 or more types together.

In the ink, the blending amount of the solvent is usually 1,000 to 100,000 parts by mass with respect to 100 parts by mass of the compound represented by formula (1A) of the present invention.

<Light emitting element>
The light-emitting device of the present invention is a light-emitting device containing a light-emitting device material containing a compound represented by formula (1A).
The structure of the light-emitting device of the present invention includes, for example, electrodes composed of an anode and a cathode, and a layer containing the light-emitting device material provided between the electrodes.

[Layer structure]
The layer containing the compound represented by formula (1A) is usually one or more layers selected from a light-emitting layer, a hole-transport layer, a hole-injection layer, an electron-transport layer, and an electron-injection layer, Preferably, it is a light-emitting layer. These layers each contain a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material. These layers are formed by dissolving a light-emitting material, a hole-transporting material, a hole-injecting material, an electron-transporting material, and an electron-injecting material, respectively, in the solvent described above, preparing an ink, and using the ink to prepare the film described above. It can be formed using the same method.

A light-emitting element has a light-emitting layer between an anode and a cathode. From the viewpoint of hole injection and hole transport properties, the light emitting device of the present invention preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light emitting layer. From the viewpoint of injection properties and electron transport properties, it is preferable to have at least one layer of an electron injection layer and an electron transport layer between the cathode and the light emitting layer. For example, as shown in FIG. 1, a light-emitting device 10 includes a hole-injection layer 3, a hole-transport layer 4, a light-emitting layer 5, an electron-transport layer 6, and an electron-injection layer 7 between an anode 1 and a cathode 2. You may have the structure laminated|stacked in this order.

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

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

In the light-emitting device of the present invention, as a method for forming each layer such as the light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, when using a low molecular weight compound, for example, vacuum from powder A vapor deposition method, a method of forming a film from a solution or a molten state, and a method of forming a film from a solution or a molten state, for example, can be used when using a polymer compound.

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

[Substrate/electrode]
The substrate in the light-emitting device may be a substrate on which an electrode can be formed and which does not change chemically when the organic layer is formed, for example, a substrate made of a material such as glass, plastic, or silicon. .

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

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

[Use]
The light-emitting device of the present invention can be used for displays, lighting, and the like.

EXAMPLES The present invention will be described in more detail below with reference to Examples, but the present invention is not limited to these Examples.

In the examples, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were measured using tetrahydrofuran as a mobile phase and by any of the following size exclusion chromatography (SEC). obtained by In addition, each measurement condition of SEC is as follows.

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

LC-MS was measured by the following method.
A sample to be measured was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg/mL, and about 1 μL was injected into an LC-MS (manufactured by Agilent, trade names: 1290 Infinity LC and 6230 TOF LC/MS). Acetonitrile and tetrahydrofuran were used as the mobile phase for LC-MS while varying the ratio, and flowed at a flow rate of 1.0 mL/min. The column used was SUMIPAX ODS Z-CLUE (manufactured by Sumika Chemical Analysis Service, inner diameter: 4.6 mm, length: 250 mm, particle size: 3 µm).

NMR was measured by the following method.
5 to 10 mg of a measurement sample is added to about 0.5 mL of heavy chloroform (CDCl3), heavy tetrahydrofuran, heavy dimethylsulfoxide, heavy acetone, heavy N,N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol or It was dissolved in methylene dichloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300, or manufactured by JEOL RESONANCE, trade name: JNM-ECZ400S/L1).

High performance liquid chromatography (HPLC) area percentage values were used as an index of compound purity. Unless otherwise specified, this value is the value at UV=254 nm in HPLC (trade name: LC-20A, manufactured by Shimadzu Corporation). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform to a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL was injected into the HPLC depending on the concentration. Acetonitrile/tetrahydrofuran was used as the mobile phase for HPLC while changing the ratio from 100/0 to 0/100 (volume ratio), and flowed at a flow rate of 1.0 mL/min. The column used was SUMIPAX ODS Z-CLUE (manufactured by Sumika Chemical Analysis Service, inner diameter: 4.6 mm, length: 250 mm, particle size: 3 μm) or an ODS column with equivalent performance. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as the detector.

(Example 1)
<Synthesis Example 1> Synthesis of compound EM-01

After creating a nitrogen gas atmosphere in the reaction vessel, 4-methoxyphenol (15.5 g) and methanol (311 mL) were added, and the mixture was stirred at room temperature (25° C., hereinafter the same) for 30 minutes. After that, the mixture was cooled to 0°C, iodobenzene diacetate (40.0 g) was added, and the mixture was stirred at 0°C for 3 hours. After that, the temperature of the obtained reaction solution was raised to room temperature, then an aqueous potassium hydroxide solution and dichloromethane were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. Anhydrous magnesium sulfate was added to the resulting organic layer, followed by filtration and concentration to obtain compound EM-01 (19.1 g). The HPLC area percentage value of compound EM-01 was 95.0% or more.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ (ppm) = 3.36 (6H, s), 6.27 (2H, d), 6.82 (2H, d)

<Synthesis Example 2> Synthesis of compound EM-02

After creating a nitrogen gas atmosphere in the reaction vessel, 1,4-dibromobenzene (34.0 g) and tetrahydrofuran (386 mL) were added, and the mixture was cooled to -70°C. After that, n-butyllithium (1.6 M hexane solution) (86 mL) was added dropwise over 30 minutes. After that, compound EM-01 (19.1 g) was added and stirred at -70°C for 2 hours. Thereafter, methanol was added dropwise, and the resulting reaction solution was warmed to room temperature, acetic acid and acetone were added, and the mixture was stirred at room temperature for 1 hour. After that, ion-exchanged water and ethyl acetate were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. After adding anhydrous magnesium sulfate to the obtained organic layer, the mixture was filtered and concentrated to obtain a solid. The resulting solid was washed with hexane to obtain compound EM-02 (23.0 g). The HPLC area percentage value of compound EM-02 was 93.0% or more.

^1H -NMR ( _CD2Cl2 , 400MHz): 2.45 (1H, s), 6.25 (2H _, d), 6.86 (2H, d), 7.36 (2H, d), 7.52 (2H, d)

<Synthesis Example 3> Synthesis of compound EM-03

After creating a nitrogen gas atmosphere in the reaction vessel, 1-bromo-4-chlorobenzene (49.0 g) and tetrahydrofuran (600 mL) were added, and the mixture was cooled to -70°C. After that, n-butyllithium (1.6 M hexane solution) (156 mL) was added dropwise over 1 hour. After that, compound EM-02 (20.0 g) was added and stirred at -70°C for 2 hours. Thereafter, methanol was added dropwise, and the resulting reaction solution was heated to room temperature, ion-exchanged water and ethyl acetate were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. Anhydrous magnesium sulfate was added to the resulting organic layer, followed by filtration and concentration to obtain compound EM-03 (24.0 g).

LC-MS (ESI, positive): m/z=376[M] ⁺

<Synthesis Example 4> Synthesis of compound EM-04

After creating a nitrogen gas atmosphere in the reaction vessel, sodium hydride (60% by mass, dispersed in liquid paraffin) (6.4 g) and tetrahydrofuran (400 mL) were added and cooled to 0°C. After that, a solution of compound EM-03 (20.0 g) dissolved in tetrahydrofuran (100 mL) was added dropwise, and the mixture was stirred at 0° C. for 30 minutes. After that, methyl iodide (37.5 g) was added and stirred at 45°C for 14 hours. Ion-exchanged water and ethyl acetate were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. After adding anhydrous magnesium sulfate to the obtained organic layer, the mixture was filtered and concentrated to obtain a solid. The resulting solid was crystallized using 2-propanol and dried at 50° C. under reduced pressure to obtain compound EM-04 (11.4 g). The HPLC area percentage value of compound EM-04 was 99.0% or more.

^1H -NMR ( _CD2Cl2 , 400MHz): 3.39 (6H, s), 6.08 (4H, s ₎ , 7.24-7.32 (6H, m), 7.44 (2H, d)

<Synthesis Example 5> Synthesis of compound EM-06

Compound EM-05 was synthesized according to the method described in Non-Patent Document 1 and Non-Patent Document 2.

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound EM-05 (8.0 g), bis(pinacolato)diboron (9.9 g), palladium acetate (80 mg), 2-dicyclohexylphosphino-2′,4′, 6′-Triisopropylbiphenyl (339 mg), potassium acetate (6.9 g) and 1,2-dimethoxyethane (120 mL) were added and stirred at 80° C. for 4 hours. Thereafter, the obtained reaction solution was cooled to room temperature and then filtered through a filter covered with celite. After that, toluene and ion-exchanged water were added, and the aqueous layer was separated. The organic layer was washed with ion-exchanged water, anhydrous magnesium sulfate and activated carbon were added to the obtained organic layer, and the mixture was filtered and concentrated to obtain a solid. The resulting solid was crystallized using a mixed solvent of toluene and acetonitrile, and dried at 50° C. under reduced pressure to obtain compound EM-06 (6.9 g). The HPLC area percentage value of compound EM-06 was 99.5% or higher.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ(ppm) = 3.41 (3H, s), 6.08 (2H, s), 7.37 (2H, d), 7.69 (2H, d)

<Synthesis Example 6> Synthesis of compound EM-07

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound EM-04 (8.1 g), compound EM-06 (5.4 g), toluene (270 mL), mesylate [(di(1-adamantyl)-n-butyl Phosphine)-2-(2′-amino-1,1′-biphenyl)]palladium (36 mg) and 20 mass % tetrabutylammonium hydroxide aqueous solution (64 g) were added, and the mixture was stirred at 90° C. for 3 hours. Thereafter, the obtained reaction solution was cooled to room temperature and then filtered through a filter covered with celite. After the resulting filtrate was washed with ion-exchanged water, the resulting organic layer was dried over anhydrous magnesium sulfate and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. The resulting solid was purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate) and dried at 50° C. under reduced pressure to obtain compound EM-07 (6.7 g). The HPLC area percentage value of compound EM-07 was 97.0% or more.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ (ppm) = 3.42 (9H, s), 6.05 (2H, d), 6.13 (4H, d), 7.28 (2H, d), 7.36 (2H, d), 7.43 (2H, d), 7.49 (2H, d), 7.56 (4H, d)

<Synthesis Example 7> Synthesis of compound EM-08

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound EM-07 (6.5 g), bis(pinacolato)diboron (3.8 g), palladium acetate (46 mg), 2-dicyclohexylphosphino-2′,4′, 6′-Triisopropylbiphenyl (197 mg), potassium acetate (2.8 g) and 1,2-dimethoxyethane (195 mL) were added and stirred at 80° C. for 5 hours. Thereafter, the obtained reaction solution was cooled to room temperature and then filtered through a filter covered with celite. After that, toluene and ion-exchanged water were added, and the aqueous layer was separated. The organic layer was washed with ion-exchanged water, anhydrous magnesium sulfate and activated carbon were added to the obtained organic layer, and the mixture was filtered and concentrated to obtain a solid. The resulting solid was crystallized using a mixed solvent of toluene and acetonitrile, and dried at 50° C. under reduced pressure to obtain compound EM-08 (6.5 g). The HPLC area percentage value of compound EM-08 was 99.0% or more.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ (ppm) = 3.45 (9H, s), 6.11-6.15 (6H, m), 7.41-7.49 (6H, m), 7.55 (4H, m), 7.70 (2H,d)

<Synthesis Example 8> Synthesis of compound EM-09

After creating a nitrogen gas atmosphere in the reaction vessel, 1,4-dibromobenzene (29.8 g) and tetrahydrofuran (250 mL) were added, and the mixture was cooled to -70°C. After that, n-butyllithium (1.6 M hexane solution) (77 mL) was added dropwise over 1 hour. After that, 1,4-naphthoquinone (5.0 g) was added and stirred at -70°C for 2 hours. Thereafter, methanol was added dropwise, and the resulting reaction solution was heated to room temperature, ion-exchanged water and ethyl acetate were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. Anhydrous magnesium sulfate was added to the resulting organic layer, followed by filtration and concentration to obtain compound EM-09 (14.9 g).

LC-MS (ESI, positive): m/z=470[M]+

<Synthesis Example 9> Synthesis of compound EM-10

After creating a nitrogen gas atmosphere in the reaction vessel, sodium hydride (60% by mass, dispersed in liquid paraffin) (3.3 g) and tetrahydrofuran (264 mL) were added and cooled to 0°C. After that, a solution of compound EM-09 (13.2 g) dissolved in tetrahydrofuran (66 mL) was added dropwise, and the mixture was stirred at 0° C. for 30 minutes. After that, methyl iodide (19.8 g) was added and stirred at 45°C for 14 hours. Ion-exchanged water and ethyl acetate were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. After adding anhydrous magnesium sulfate to the obtained organic layer, the mixture was filtered and concentrated to obtain a solid. The resulting solid was crystallized using a mixed solvent of toluene and 2-propanol, and dried at 50° C. under reduced pressure to obtain compound EM-10 (8.1 g). The HPLC area percentage value of compound EM-10 was 99.0% or more.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ(ppm) = 3.16 (3H, s), 6.09 (1H, s), 7.16 (2H, d), 7.37 (4H, m)

<Synthesis Example 10> Synthesis of compound EM-11

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound EM-08 (500 mg), compound EM-10 (218 mg), toluene (250 mL), [tris(dibenzylideneacetone)] dipalladium (9.5 mg), 2- Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (14.3 mg) and 2 mass % tetrabutylammonium hydroxide aqueous solution (16.9 g) were added and stirred at 90° C. for 3 hours. Thereafter, the obtained reaction solution was cooled to room temperature and then filtered through a filter covered with celite. After the obtained filtrate was washed with ion-exchanged water, the obtained organic layer was dried with anhydrous magnesium sulfate and activated carbon, and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. The resulting solid was crystallized using a mixed solvent of toluene and 2-propanol, and dried at 50° C. under reduced pressure to obtain compound EM-11 (350 mg). The HPLC area percentage value of compound EM-11 was 96.0% or more.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ(ppm) = 3.17 (3H, s), 3.40 (9H, s), 6.10 (7H, m), 7.35-7.46 (18H, m)
LC-MS (ESI, positive): m/z=1210[M]+

<Synthesis Example 11> Synthesis of compound EM-12

After the inside of the reaction vessel was replaced with a nitrogen gas atmosphere, naphthalene (1.6 g), metallic sodium (346 mg) and tetrahydrofuran (29 mL) were added and stirred at 0°C for 6 hours to prepare a sodium naphthalenide solution.
Subsequently, after the reaction vessel was filled with a nitrogen gas atmosphere, compound EM-11 (198 mg) and tetrahydrofuran (24 mL) were added, and the mixture was cooled to -70°C. After that, the sodium naphthalenide solution prepared earlier was added, and the mixture was stirred at -70°C for 2 hours. Thereafter, iodine was added, and the resulting reaction solution was heated to room temperature, ion-exchanged water and dichloromethane were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. The resulting organic layer was dried with anhydrous magnesium sulfate and activated carbon and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. Further, the resulting solid was washed with methanol to obtain a crude form of compound EM-12.
Subsequently, after the reaction vessel was filled with a nitrogen gas atmosphere, the obtained crude compound EM-12, 2,3-dichloro-5,6-dicyano-p-benzoquinone (107 mg) and chlorobenzene (20 mL) were added. and 70° C. for 5 hours. After that, the resulting reaction solution was cooled to room temperature, ion-exchanged water and dichloromethane were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. The obtained solid was purified by silica gel column chromatography (dichloromethane), further crystallized using a mixed solvent of toluene, 2-propanol and methanol, and dried under reduced pressure at 50° C. to obtain compound EM-12. (36 mg) was obtained. The HPLC area percentage value of compound EM-12 was greater than 97.0%.

LC-MS (ESI, positive): m/z=962[M] ⁺

The maximum peak wavelength of the emission spectrum of compound EM-12 was 468 nm.

(Example 2)
<Synthesis Example 12> Synthesis of compound EM-13

After making the inside of the reaction vessel a nitrogen gas atmosphere, the compound EM-08 (500 mg), 1,4-dibromonaphthalene (123 mg), toluene (250 mL), [tris(dibenzylideneacetone)] dipalladium (9.5 mg). , 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (14.3 mg) and 2% by mass aqueous tetrabutylammonium hydroxide solution (16.9 g) were added and stirred at 90° C. for 3 hours. Thereafter, the obtained reaction solution was cooled to room temperature and then filtered through a filter covered with celite. After the obtained filtrate was washed with ion-exchanged water, the obtained organic layer was dried with anhydrous magnesium sulfate and activated carbon, and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. The resulting solid was crystallized using a mixed solvent of toluene and 2-propanol, and dried at 50° C. under reduced pressure to obtain compound EM-13 (210 mg). The HPLC area percentage value of compound EM-13 was greater than 96.0%.

¹ H-NMR (CD ₂ Cl ₂ , 400 MHz): δ(ppm) = 3.40-3.51 (9H, m), 6.07-6.26 (6H, m), 7.40-7.60 (15H, m)
LC-MS (ESI, positive): m/z=996[M]+

<Synthesis Example 13> Synthesis of compound EM-14

After the inside of the reaction vessel was replaced with a nitrogen gas atmosphere, naphthalene (0.7 g), metallic sodium (149 mg) and tetrahydrofuran (10 mL) were added and stirred at 0°C for 6 hours to prepare a sodium naphthalenide solution.
Subsequently, after the reaction vessel was filled with a nitrogen gas atmosphere, compound EM-13 (70 mg) and tetrahydrofuran (10 mL) were added, and the mixture was cooled to -70°C. After that, the sodium naphthalenide solution prepared earlier was added, and the mixture was stirred at -70°C for 2 hours. Thereafter, iodine was added, and the resulting reaction solution was heated to room temperature, ion-exchanged water and dichloromethane were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. The resulting organic layer was dried with anhydrous magnesium sulfate and activated carbon and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. Further, the obtained solid was washed with methanol to obtain a crude form of compound EM-14.
Subsequently, after the reaction vessel was filled with a nitrogen gas atmosphere, the obtained crude compound EM-14, 2,3-dichloro-5,6-dicyano-p-benzoquinone (46 mg) and chlorobenzene (8 mL) were added. , and 70° C. for 4 hours. After that, the resulting reaction solution was cooled to room temperature, ion-exchanged water and dichloromethane were added, and the mixture was stirred at room temperature. After that, the aqueous layer was separated, and the organic layer was washed with deionized water. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered. A solid was obtained by concentrating the obtained filtrate under reduced pressure. The resulting solid was purified by silica gel column chromatography (dichloromethane), crystallized using a mixed solvent of toluene, 2-propanol and methanol, and dried at 50° C. under reduced pressure to give compound EM-14. (12 mg) was obtained. The HPLC area percentage value of compound EM-14 was greater than 96.0%.

LC-MS (ESI, positive): m/z=810[M]+

The maximum peak wavelength of the emission spectrum of compound EM-14 was 474 nm.

(Luminescent materials other than those of the examples)
<Synthesis Example 14> Synthesis of Compound EM-3 Compound EM-3 was synthesized according to the method described in JP-A-2009-290091 and JP-A-2011-176304.

The maximum peak wavelength of the emission spectrum of compound EM-3 was 460 nm.

(Materials other than light-emitting materials)
<Synthesis Example 15> Synthesis and Acquisition of Compounds HM-1 to HM-3 Compound HM-1 was purchased from AK Scientific.
Compound HM-2 was synthesized according to the method described in WO2011/137922.
Compound HM-3 was synthesized according to the method described in JP-A-2011-100942 and WO2011/137922.

The maximum peak wavelength of the emission spectrum of compound HM-1 was 425 nm.
The maximum peak wavelength of the emission spectrum of compound HM-2 was 430 nm.
The maximum peak wavelength of the emission spectrum of compound HM-3 was 430 nm.

<Synthesis Example 16> Synthesis and Acquisition of Compounds 6 to 8 As compound 6, a commercially available product was used.
Compound 7 was synthesized according to the method described in WO2009/131255.
Compound 8 was synthesized according to the method described in WO2016/031639.

<Synthesis Example 17> Synthesis of polymer compound 1 After making the inside of the reaction vessel an inert gas atmosphere, compound 8 (0.096 g), compound 6 (0.916 g), compound 7 (1.119 g), dichlorobis(phenyl) Phosphine)palladium (1.5 mg) and toluene (47 mL) were added and heated to 105°C.
Thereafter, a 10% by mass tetraethylammonium hydroxide aqueous solution (18 mL) was added dropwise thereto, and refluxed for 4 hours. Thereafter, phenylboronic acid (48.8 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.9 mg) were added thereto and refluxed for 6 hours. After cooling the resulting reaction mixture, it was washed twice with water, twice with a 10% by mass hydrochloric acid aqueous solution, twice with 3% by mass aqueous ammonia, and twice with water. The resulting solution was added dropwise to methanol and stirred to cause precipitation. The resulting precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in that order. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The resulting precipitate was collected by filtration and dried to obtain 1.1 g of polymer compound 1. Polymer compound 1 had Mn of 5.0×10 ⁴ and Mw of 1.1×10 ⁵ .

According to the theoretical value obtained from the amount of the raw material charged, the polymer compound 1 has a structural unit derived from the compound 6, a structural unit derived from the compound 7, and a structural unit derived from the compound 8, which is 45: It is a copolymer composed in a molar ratio of 50:5.

<Example D1> Production and evaluation of light emitting device D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. A film of ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, is formed on the anode to a thickness of 35 nm by spin coating, and heated on a hot plate at 240° C. for 15 minutes in an air atmosphere. A hole injection layer was formed by

(Formation of hole transport layer)
A polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method, and was heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere. A pore transport layer was formed. The polymer compound HTL-1 is the polymer compound of Polymer Example 1 of International Publication No. 2014/102543.

(Formation of light-emitting layer)
Compound HM-1 and compound EM-12 (compound HM-1:compound EM-12=95% by mass:5% by mass) were dissolved in toluene at a concentration of 1.5% by mass. Using the obtained toluene solution, a film having a thickness of 60 nm was formed on the hole transport layer by spin coating, and the film was heated on a hot plate at 130° C. for 10 minutes in a nitrogen gas atmosphere to emit light. formed a layer.

(Formation of cathode)
After reducing the pressure of the substrate on which the light-emitting layer is formed to 1×10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride of about 7 nm is deposited on the light-emitting layer as a cathode, and then on the sodium fluoride layer, About 120 nm of aluminum was evaporated. After vapor deposition, the light-emitting device D1 was produced by sealing with a glass substrate.

(Evaluation of Light Emitting Element)
By applying a voltage to the light-emitting element D1, EL emission having the maximum peak wavelength of the emission spectrum at 465 nm was observed at 100 cd/m ² . The CIE1931 chromaticity coordinates at this time were (0.15, 0.19). After setting the current value so that the initial current density was 20 mA/cm ² , the device was driven at a constant current, and the change in brightness over time was measured using an organic EL brightness evaluation system (PEL-100T, manufactured by EHC). It took 118 hours until the luminance reached 70% of the initial luminance. The initial luminance is the luminance when constant current driving of the light emitting element is started after setting the current value so that the initial current density is 20 mA/cm ² . Further, in this specification, the time from the start of constant current driving of the light emitting element until the luminance reaches 70% of the initial luminance is defined as the luminance lifetime.

<Examples D2 to D3> Production and Evaluation of Light Emitting Elements D2 to D3 In place of “Compound HM-1 and Compound EM-12” in Example D1 (formation of light emitting layer), the materials listed in Table 2 were used. Light-emitting devices D2 and D3 were produced in the same manner as in Example D1, except that they were used.

<Comparative Examples CD1 to CD3> Production and Evaluation of Light Emitting Elements CD1 to CD3 Instead of “Compound HM-1 and Compound EM-12” in Example D1 (formation of light emitting layer), the materials listed in Table 2 were used. Light-emitting elements CD1 to CD3 were produced in the same manner as in Example D1, except that they were used.

<Example D4> Fabrication and Evaluation of Light Emitting Device D4 An anode, a hole injection layer, and a hole transport layer were formed in the same manner as in Example D1.
(Formation of light-emitting layer)
Polymer compound 1 and compound EM-12 (polymer compound 1:compound EM-12=95% by mass:5% by mass) were dissolved in xylene at a concentration of 1.2% by mass. Using the obtained xylene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and light was emitted by heating on a hot plate at 130° C. for 10 minutes in a nitrogen gas atmosphere. formed a layer.

(Formation of cathode)
After reducing the pressure of the substrate on which the light-emitting layer was formed to 1×10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride of about 7 nm was deposited on the light-emitting layer as a cathode, and then on the sodium fluoride layer, About 120 nm of aluminum was evaporated. After vapor deposition, a light-emitting element D4 was produced by sealing with a glass substrate.

(Evaluation of Light Emitting Element)
By applying a voltage to the light emitting element D4, EL emission having the maximum peak wavelength of the emission spectrum at 445 nm was observed at 100 cd/m ² . The CIE1931 chromaticity coordinates at this time were (0.15, 0.09). After setting the current value so that the initial current density was 20 mA/cm ² , the device was driven at a constant current, and the change in brightness over time was measured. It took 7 hours for the brightness to reach 70% of the initial brightness.

<Example D5> Production and Evaluation of Light-Emitting Element D5 Example D4 and Evaluation were the same as in Example D4, except that the materials listed in Table 3 were used instead of "Compound EM-12" in (Formation of light-emitting layer) of Example D4. Similarly, a light-emitting element D5 was produced.

<Comparative Example CD4> Production and Evaluation of Light-Emitting Element CD4 Example D4 and Evaluation were the same as in Example D4, except that the materials listed in Table 3 were used instead of "Compound EM-12" in (Formation of light-emitting layer) of Example D4. Similarly, a light-emitting element CD4 was produced.

DESCRIPTION OF SYMBOLS 1... Anode, 2... Cathode, 3... Hole injection layer, 4... Hole transport layer, 5... Light emitting layer, 6... Electron transport layer, 7... Electron injection layer, 10... Light emitting element.

Claims (4)

a compound represented by the formula (1A-A2) ;
A light-emitting device material containing at least one selected from the group consisting of a compound represented by formula (FH-1) and a polymer compound containing a structural unit represented by formula (Y).

[In the formula (1A-A2), Ar ² represents a condensed ring arylene group, and said group may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. The 1,4-phenylene group in the formula may have a substituent. When the 1,4-phenylene group has a plurality of substituents, they may be bonded together to form a ring together with the atoms to which they are bonded. n represents an integer of 5 or more and 19 or less. ]

[In formula (FH-1), Ar ^{1 H1} and Ar ^{2 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 the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
n ^H1 represents an integer of 0 or more and 15 or less.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by -[C(R ^H11 ) ₂ ]-, and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When ^multiple LH1 are present, they may be the same or different. R ^H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. A plurality of RH11 ^may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[In the formula (Y), 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. and these groups may have a substituent. When a plurality of the substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. ] 2. The light-emitting device material according to claim 1 , wherein the condensed ring arylene group is a naphthalenediyl group, an anthracenediyl group or a pyrenediyl group (these groups may have a substituent). 3. The light-emitting device according to claim 1, further comprising at least one selected from the group consisting of a hole-transporting material, a hole-injecting material, an electron- transporting material, an electron-injecting material, a light-emitting material, an antioxidant and a solvent. material. A light-emitting device comprising the light-emitting device material according to any one of claims 1 to 3 .

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