JP2016111355A - Light-emitting element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a light-emitting element having excellent power efficiency.SOLUTION: The light-emitting element includes an anode, a cathode, a first organic layer disposed between the anode and the cathode, and a second organic layer disposed between the anode and the first organic layer. The first organic layer contains a phosphorescent compound; the second organic layer contains a polymer cured product formed from a polymer composition in which one or more polymer compounds are blended; at least one of the polymer compounds has a crosslinking group; at least one of the polymer compounds contains a phosphorescent structural unit; and an average number of crosslinking groups per 1000 molecular weight is 0.60 or more.SELECTED DRAWING: None

Description

  The present invention relates to a light emitting element.

  Light emitting devices such as organic electroluminescence devices (organic EL devices) can be suitably used for display and lighting applications because of their high external quantum efficiency and low voltage drive characteristics. Yes. This light-emitting element includes organic layers such as a light-emitting layer and a charge transport layer.

  Patent Document 1 is an organic electroluminescent element having a light emitting layer, and the light emitting layer includes two adjacent layers formed by a wet film forming method using a composition containing a light emitting material and a solvent. The organic electroluminescent device is characterized in that the two adjacent layers each contain a different light emitting material and satisfy specific parameters.

  Patent Document 2 describes a light-emitting element having a first organic layer containing a fluorescent compound and a second organic layer containing a phosphorescent compound.

  Patent Documents 3 and 4 include a light-emitting layer formed using a blue phosphorescent compound having a ligand formed from a 6-membered ring and a 5-membered ring, an aromatic amine constituent unit, and a crosslinkable constituent unit. A light-emitting element having a hole transporting layer formed using a polymer compound containing benzene is described.

JP 2011-253722 A International Publication No. 2013/064814 International Publication No. 2014/19186 JP 2013-216789 A

  As a light emitting element, what has the outstanding power efficiency is calculated | required. Therefore, an object of the present invention is to provide a light-emitting element that is excellent in power efficiency.

  One aspect of the present invention relates to the following light-emitting element.

The anode,
A cathode,
A first organic layer provided between the anode and the cathode;
A light emitting device having a second organic layer provided between the anode and the first organic layer,
The first organic layer comprises a phosphorescent compound;
The second organic layer includes a polymer cured product formed from a polymer composition in which one or more polymer compounds are blended,
At least one of the polymer compounds has a crosslinking group,
At least one of the polymer compounds includes a phosphorescent constituent unit;
For each monomer unit constituting the polymer compound, a value x obtained by multiplying the molar ratio C of the monomer unit to the total mole of all monomer units and the molecular weight M of the monomer unit, and When a value y obtained by multiplying the molar ratio C by the number n of the cross-linking groups of the monomer unit is obtained, it is calculated from the sum X _{1 of} x and the sum Y _{1 of} y (Y ₁ × 1000) / X ₁ is a light emitting element having a value of 0.6 or more.

  ADVANTAGE OF THE INVENTION According to this invention, the light emitting element excellent in power efficiency can be provided.

  A preferred embodiment of the present invention will be described below.

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

  Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, i-Pr represents an isopropyl group, and t-Bu represents a tert-butyl group.

  The hydrogen atom may be a deuterium atom or a light hydrogen atom.

  In formulas representing metal complexes (for example, in formulas (1-A) and (1-B) representing phosphorescent compounds), a solid line representing a bond with a central metal means a covalent bond or a coordinate bond. .

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

“Low molecular weight compound” means a compound having no molecular weight distribution and a molecular weight of 1 × 10 ⁴ or less.

  “Structural unit” means one or more units present in a polymer compound.

  The “alkyl group” may be linear or branched. The carbon atom number of a linear alkyl group is 1-50 normally without including the carbon atom number of a substituent, Preferably it is 3-30, More preferably, it is 4-20. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.

  As the alkyl group, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group, heptyl group, octyl group, Examples include 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group, and the like. In addition, the alkyl group may have a substituent. For example, part or all of the hydrogen atoms in the alkyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a group. Examples of the alkyl group having a substituent include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, and 3- (4-methylphenyl). A propyl group, a 3- (3,5-di-hexylphenyl) propyl group, and a 6-ethyloxyhexyl group may be mentioned.

  The number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30 and more preferably 4 to 20 without including the number of carbon atoms of the substituent.

  Examples of the cycloalkyl group include a cyclohexyl group and a cyclopentyl group. The cycloalkyl group may have a substituent. For example, part or all of the hydrogen atoms in the cycloalkyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, and the like. It may be a substituted group. Examples of the cycloalkyl group having a substituent include a cyclohexylmethyl group and a cyclohexylethyl group.

  “Aryl group” means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon. The number of carbon atoms constituting the aromatic ring in the aryl group is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10.

  As the aryl group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, A 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 2-phenylphenyl group, a 3-phenylphenyl group, a 4-phenylphenyl group, and the like can be given. The aryl group may have a substituent. For example, part or all of the hydrogen atoms in the aryl group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a radical.

  The “alkoxy group” may be linear or branched. The carbon atom number of a linear alkoxy group is 1-40 normally without including the carbon atom number of a substituent, Preferably it is 4-10. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.

  Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2 -Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the like. The alkoxy group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkoxy group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be.

  The number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.

  Examples of the cycloalkoxy group include a cyclohexyloxy group and a cyclopentyloxy group. The cycloalkoxy group may have a substituent. For example, some or all of the hydrogen atoms in the cycloalkoxy group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms, etc. The group may be substituted with

  “Aryloxy group” means an atomic group in which one aryl group is bonded to an oxygen atom. The number of carbon atoms constituting the aromatic ring in the aryloxy group is usually 6 to 60, preferably 6 to 20.

  Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, and a 1-pyrenyloxy group. The aryloxy group may have a substituent. For example, part or all of the hydrogen atoms in the aryloxy group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like. It may be a radical.

  “P-valent heterocyclic group” (p represents an integer of 1 or more) is a direct bond from a heterocyclic compound to a carbon atom or heteroatom constituting a heterocyclic ring or a ring condensed with the heterocyclic ring. It means the remaining atomic group from which p hydrogen atoms have been removed. Among the p-valent heterocyclic groups, p hydrogen atoms among the hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the heterocyclic ring or the condensed ring with the heterocyclic ring from the aromatic heterocyclic compound The “p-valent aromatic heterocyclic group” which is the remaining atomic group excluding is preferred.

  `` Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc. A compound in which the ring itself exhibits aromaticity and a heterocyclic ring such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran itself does not exhibit aromaticity, but the aromatic ring is condensed to the heterocyclic ring. Means a compound.

  The number of carbon atoms constituting the heterocyclic ring and the condensed ring with the heterocyclic ring in the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20.

  Examples of the monovalent heterocyclic group include thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group and the like. The monovalent heterocyclic group may have a substituent. For example, part or all of the hydrogen atoms in the monovalent heterocyclic group are an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, and the like. It may be a substituted group.

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

  The “amino group” may have a substituent, and a substituted amino group is preferable. As a substituent which an amino group has, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.

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

  The “alkenyl group” may be linear or branched. The carbon atom number of a linear alkenyl group is 2-30 normally without including the carbon atom number of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.

  The number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.

Examples of the alkenyl group and cycloalkenyl group include a 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, etc. are mentioned.
The alkenyl group may have a substituent, for example, a group in which part or all of the hydrogen atoms in the alkenyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be. In addition, the cycloalkenyl group may have a substituent. For example, a part or all of the hydrogen atoms in the cycloalkenyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms. It may be a group substituted with or the like.

  The “alkynyl group” may be linear or branched. The carbon atom number of an alkynyl group is 2-20 normally without including the carbon atom of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.

  The number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.

  Examples of the alkynyl group and cycloalkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 5 -A hexynyl group, etc. are mentioned. The alkynyl group may have a substituent, for example, a group in which some or all of the hydrogen atoms in the alkynyl group are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be. In addition, the cycloalkynyl group may have a substituent. For example, a part or all of the hydrogen atoms in the cycloalkynyl group are alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, aryl groups, fluorine atoms. It may be a group substituted with or the like.

  “Arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting an aromatic ring from an aromatic hydrocarbon. The number of carbon atoms constituting the aromatic ring in the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18.

  Examples of the arylene group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, and the like. The arylene group may have a substituent. For example, part or all of the hydrogen atoms in the arylene group are substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. It may be a radical.

  The arylene group is preferably represented by formulas (A-1), (A-2), (A-3), (A-4), (A-5), (A-6), (A-7), (A-8), (A-9), (A-10) (A-11), (A-12), (A-13), (A-14), (A-15), (A- 16), (A-17), (A-18), (A-19) or a group represented by (A-20) (hereinafter, in some cases, in the formulas (A-1) to (A-20) It is referred to as a “represented group”. The arylene group includes a group in which a plurality of these groups are bonded.

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 each is bonded.

  The number of carbon atoms constituting the heterocyclic ring and the ring condensed with the heterocyclic ring in the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15 It is.

  Examples of the divalent heterocyclic group include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, Divalent or diazole or diazole is a divalent compound obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting a heterocycle or a ring condensed with a heterocycle. Groups.

  The divalent heterocyclic group is preferably represented by the formula (AA-1), (AA-2), (AA-3), (AA-4), (AA-5), (AA-6), (AA -7), (AA-8), (AA-9), (AA-10), (AA-11), (AA-12), (AA-13), (AA-14), (AA-15) ), (AA-16), (AA-17), (AA-18), (AA-19), (AA-20), (AA-21), (AA-22), (AA-23), (AA-24), (AA-25), (AA-26), (AA-27), (AA-28), (AA-29), (AA-30), (AA-31), (AA -32), (AA-33) or (AA-34) (hereinafter referred to as “groups represented by formulas (AA-1) to (AA-34)” in some cases). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

In the formula, R and R ^a represent the same meaning as described above.

  The “crosslinking group” is a group capable of generating a new bond by being subjected to a heat treatment, an ultraviolet irradiation treatment, a radical reaction, or the like. Preferably, the formula (XL-1) of the crosslinking group A group , (XL-2), (XL-3), (XL-4), (XL-5), (XL-6), (XL-7), (XL-8), (XL-9), ( XL-10), (XL-11), (XL-12), (XL-13), (XL-14), (XL-15), (XL-16) or (XL-17) It is a cross-linking group (hereinafter referred to as “groups represented by formulas (XL-1) to (LX-17)” in some cases).

In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * Represents a bonding position. These crosslinkable groups may have a substituent.

  “Substituent” includes, for example, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group, and an alkenyl. It may be a group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl group. Further, the substituent may be a crosslinking group.

<Light emitting element>
Next, a light emitting device according to an embodiment of the present invention will be described.

The light emitting device according to this embodiment includes an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the first organic layer. Have The first organic layer is a layer formed using a phosphorescent compound, and the second organic layer is formed using a polymer composition in which one or more polymer compounds are blended. Is the layer to be played. At least one of the polymer compounds has a crosslinking group (specifically, at least one of the polymer compounds includes a crosslinkable structural unit having a crosslinking group). In addition, at least one of the polymer compounds includes a phosphorescent structural unit. Further, for each monomer unit constituting the polymer compound, a value x obtained by multiplying the molar ratio C of the monomer unit to the total mole of all monomer units and the molecular weight M of the monomer unit, and When the value y obtained by multiplying the molar ratio C and the number n of crosslinking groups of the monomer unit is obtained, the sum x _{1 of} x and the sum Y _{1 of} y are calculated (Y ₁ × 1000) / the value of X ₁ is equal to or greater than 0.6.

  “Formed using” in relation to the relationship between the first organic layer and the phosphorescent compound means that the first organic layer is formed using the phosphorescent compound. The phosphorescent compound may be contained as it is in the first organic layer, or the phosphorescent compound is contained in the first organic layer in a state of being crosslinked in the molecule, between the molecules, or both. May be. That is, the first organic layer may contain a phosphorescent compound and / or a crosslinked product of the phosphorescent compound.

  “Formed by using” in relation to the relationship between the second organic layer and the polymer composition means that the second organic layer is formed using the polymer composition. The polymer composition may be included in the second organic layer as it is, and the crosslinkable polymer compound (polymer compound having a crosslinking group) contained in the polymer composition is intramolecular, intermolecular, or , And may be contained in the second organic layer in a state of being crosslinked by both of them. That is, the second organic layer may include a polymer compound and / or a crosslinked product of the polymer compound, and a polymer cured product obtained by curing the polymer composition and / or polymer composition. It may be included.

  Examples of the method for forming the first organic layer and the second organic layer include a vacuum deposition method, and a coating method typified by a spin coating method and an ink jet printing method.

  When the first organic layer is formed by a coating method, it is preferable to use an ink for the first organic layer described later. After forming the first organic layer, the phosphorescent compound may be crosslinked by heating or light irradiation. When the phosphorescent compound is contained in the first organic layer in a crosslinked state, the first organic layer is substantially insolubilized in the solvent. Therefore, the first organic layer can be suitably used for stacking light emitting elements.

When the second organic layer is formed by a coating method, it is preferable to use an ink for the second organic layer described later. After forming the second organic layer, the polymer composition can be cured by crosslinking the crosslinkable polymer compound contained in the polymer composition by heating or light irradiation.
When the polymer composition is contained in the second organic layer in a cured state, the second organic layer is substantially insolubilized in the solvent. Therefore, the second organic layer can be suitably used for stacking light emitting elements.

  The light-emitting element according to this embodiment is preferably contained in the second organic layer in a state where the crosslinkable polymer compound contained in the polymer composition is crosslinked. That is, it is preferable that the second organic layer includes a polymer cured product formed from the polymer composition.

  The heating temperature for crosslinking is usually 25 to 300 ° C, preferably 50 to 250 ° C, more preferably 150 to 200 ° C.

  Types of light used for light irradiation for crosslinking are, for example, ultraviolet light, near ultraviolet light, and visible light.

<First organic layer>
The first organic layer is a layer formed using one or more phosphorescent compounds.

[Phosphorescent compound]
The phosphorescent compound is a compound having phosphorescence. As the phosphorescent compound, a compound having a high emission quantum yield at room temperature can be suitably used.

  Examples of the phosphorescent compound include a phosphorescent compound represented by the formula (1).

Where
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹ represents an integer of ¹ to 3, n ² represents an integer of 0 to 2, and n ¹ + n ² represents 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹ + n ² is 3, and when M is a palladium atom or platinum atom, n ¹ + n ² is 2.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. However, at least one of E ¹ and E ² is a carbon atom. When a plurality of E ¹ and E ² are present, they may be the same or different.
Ring R ¹ represents a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings R ¹ are present, they may be the same or different. However, if the ring R ¹ is a 6-membered heteroaromatic ring, E ¹ is a carbon atom.
Ring R ² represents a 5-membered or 6-membered aromatic carbocyclic ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings R ² are present, they may be the same or different. However, when the ring R ² is a 6-membered aromatic heterocyclic ring, E ² is a carbon atom.
The substituent that the ring R ¹ may have and the substituent that the ring R ² may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different.

The phosphorescent compound represented by the formula (1) has M as a central metal, a ligand whose number is defined by the subscript n ¹ , and its number is defined by the subscript n ² . It consists of a ligand.

When M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹ is preferably 2 or 3, and more preferably 3.

When M is a palladium atom or a platinum atom, n ¹ is preferably 1 or 2, and more preferably 2.

E ¹ and E ² are preferably carbon atoms.

Ring R ¹ is a 5-membered aromatic heterocycle having 1 to 3 nitrogen atoms as constituent atoms, or a 6-membered aromatic heterocycle having 1 to 4 nitrogen atoms as constituent atoms And preferably a 5-membered aromatic heterocycle having 2 or more and 3 or less nitrogen atoms as constituent atoms or a 6-membered aromatic heterocycle having 1 or more and 3 or less nitrogen atoms as constituent atoms. The ring is more preferably an imidazole ring, a triazole ring, a pyridine ring or a pyrimidine ring, and these rings may have a substituent.

Ring R ² is preferably a 6-membered aromatic carbocycle, or a 5-membered or 6-membered aromatic heterocycle, and is a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, diazabenzene. It is more preferably a ring, pyrrole ring, furan ring or thiophene ring, more preferably a benzene ring, naphthalene ring, fluorene ring, pyridine ring or diazabenzene ring, and a benzene ring, pyridine ring or pyrimidine ring. Particularly preferred, these rings may have a substituent.

Examples of the substituent that the ring R ¹ and the ring R ² may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, A dendron is preferable, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a halogen atom or a dendron is more preferable, an alkyl group, a cycloalkyl group, an aryl group, a halogen atom or a dendron is further preferable, and these groups May further have a substituent.

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

  In formula, * shows the site | part couple | bonded with M.

  As the phosphorescent compound represented by the formula (1), a phosphorescent compound represented by the formula (1-A) or a phosphorescent compound represented by the formula (1-B) is preferably used. it can.

Where
^M, n ^1, n 2, ^{E 1} and ^A 1 ^-G 1 -A ² is, ^M in each formula (1), the same meaning as n ^1, n 2, ^{E 1} and ^A 1 ^-G 1 -A ² Represent.
^E11A , ^E12A , ^E13A , ^E21A , ^E22A , ^E23A and ^E24A each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^11A , E ^12A , E ^13A , E ^21A , E ^22A , E ^23A and E ^24A are present, they may be the same or different. When E ^11A , E ^12A and E ^13A are nitrogen atoms, R ^11A , R ^12A and R ^13A may be present or absent. When E ^21A , E ^22A , E ^23A and E ^24A are nitrogen atoms, R ^21A , R ^22A , R ^23A and R ^24A are not present.
R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A , they may be the same or different. R ^11A and R ^12A , R ^12A and R ^13A , R ^11A and R ^21A , R ^21A and R ^22A , R ^22A and R ^23A , and R ^23A and R ^24A are bonded to each other together with the atoms to which they are bonded. A ring may be formed.
Ring L ^1A represents a triazole ring or an imidazole ring composed of a nitrogen atom, E ¹ , E ^11A , E ^12A and E ^13A .
Ring L ^2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21A , E ^22A , E ^23A and E ^24A .

Where
^M, n 1, ^{n 2} and ^A 1 ^-G 1 -A ² is, ^M in each formula (1) ^represent the same meaning as n 1, ^{n 2} and ^A 1 ^-G 1 -A ^2.
E11B , ^E12B , ^E13B , ^E14B , ^E21B , ^E22B , ^E23B and ^E24B each independently represent a nitrogen atom or a carbon atom. When there are a plurality of E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B , they may be the same or different. When E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B are nitrogen atoms, R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is not present.
R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a halogen atom or a substituted amino group is represented, and these groups may have a substituent. When there are a plurality of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B , they may be the same or different. R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , R ^11B and R ^21B , R ^21B and R ^22B , R ^22B and R ^23B , and R ^23B and R ^24B are combined, You may form the ring with the atom to which each couple | bonds.
Ring L ^1B represents a pyridine ring or a pyrimidine ring composed of a nitrogen atom, a carbon atom, E ^11B , E ^12B , E ^13B and E ^14B .
Ring L ^2B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21B , E ^22B , E ^23B and E ^24B .

  Hereinafter, the phosphorescent compound represented by the formula (1-A) and the phosphorescent compound represented by the formula (1-B) will be described in detail.

[Phosphorescent Compound Represented by Formula (1-A)]
The phosphorescent compound represented by the formula (1-A) has M as the central metal, a ligand whose number is defined by the subscript n ¹ , and its number is defined by the subscript n ^2. And is composed of a ligand.

Examples and preferred embodiments of M, n ¹ , n ² , E ¹ and A ¹ -G ¹ -A ^{2 in} the phosphorescent compound represented by the formula (1-A) are represented by the formula (1). Examples of M, n ¹ , n ² , E ¹ and A ¹ -G ¹ -A ^{2 in} the phosphorescent compound include the same examples and preferred embodiments.

When the ring L ^1A is an imidazole ring, an imidazole ring in which E ^11A is a nitrogen atom or an imidazole ring in which E ^12A is a nitrogen atom is preferable, and an imidazole ring in which E ^11A is a nitrogen atom is more preferable.

When ring L ^1A is a triazole ring, a triazole ring in which E ^11A and E ^12A are nitrogen atoms, or a triazole ring in which E ^11A and E ^13A are nitrogen atoms is preferable, and E ^11A and E ^12A are nitrogen atoms. A triazole ring is more preferred.

When E ^11A is a nitrogen atom and R ^11A is present, R ^11A is preferably a group represented by an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a substituted amino group. , A hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group.

When E ^11A is a carbon atom, R ^11A is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and is a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group. It is more preferable that it is a hydrogen atom, an alkyl group, or a cycloalkyl group.

When E ^12A is a nitrogen atom and R ^12A is present, R ^12A is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group It is more preferably a group, a cycloalkyl group or an aryl group, and further preferably a hydrogen atom, an alkyl group or a cycloalkyl group.

When E ^12A is a carbon atom, R ^12A is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group It is more preferable that it is a hydrogen atom, an alkyl group, or a cycloalkyl group.

When E ^13A is a nitrogen atom and R ^13A is present, R ^13A is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group It is more preferably a group, a cycloalkyl group or an aryl group, and further preferably a hydrogen atom, an alkyl group or a cycloalkyl group.

When E ^13A is a carbon atom, R ^13A is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group It is more preferable that it is a hydrogen atom, an alkyl group, or a cycloalkyl group.

When ring L ^2A is a pyridine ring, a pyridine ring in which E ^21A is a nitrogen atom, a pyridine ring in which E ^22A is a nitrogen atom, or a pyridine ring in which E ^23A is a nitrogen atom is preferable, and E ^22A is a nitrogen atom. Some pyridine rings are more preferred.

When ring L ^2A is a pyrimidine ring, a pyrimidine ring in which E ^21A and E ^23A are nitrogen atoms, or a pyrimidine ring in which E ^22A and E ^24A are nitrogen atoms is preferable, and E ^22A and E ^24A are nitrogen atoms. A pyrimidine ring is more preferred.

Ring L ^2A is preferably a benzene ring.

R ^21A , R ^22A , R ^23A and R ^24A are each independently preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cyclo An alkyl group or an aryl group is more preferable, and a hydrogen atom, an alkyl group, or an aryl group is still more preferable.

When R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A, and R ^24A are an aryl group, a monovalent heterocyclic group, or a substituted amino group, the power efficiency of the light-emitting element is more excellent. Preferably there is.

  “Dendron” means a group having a regular dendritic branch structure (ie, a dendrimer structure) having an atom or ring as a branch point. Examples of the compound having dendron (hereinafter referred to as “dendrimer”) include, for example, International Publication No. 02/066733, Japanese Patent Application Laid-Open No. 2003-231692, International Publication No. 2003/079736, International Publication No. 2006/097717. And the structure described in the literature.

  As the dendron, a group represented by the formula (DA) or (DB) is preferable.

Where
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
G ^DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different.
Note that * represents a bonding position.

Where
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more.
G ^DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. A plurality of ^GDA may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different.
Note that * represents a bonding position.

  GDA is preferably a group represented by the formula (GDA-11), (GDA-12), (GDA-13), (GDA-14) or (GDA-15) (hereinafter referred to as “formula (GDA- 11) to (GDA-15) "), and these groups may have a substituent.

Where
* Is, ^{Ar DA1} in the formula (D-A), formula (D-B) in ^{Ar DA1,} formula (D-B) ^Ar in ^DA2, or represents a bond between ^{Ar DA3} in the formula (D-B).
** is, ^{Ar DA2} in the formula (D-A), ^{Ar DA2} in the formula (D-B), ^Ar in the formula (D-B) ^DA4, or represents a bond between ^{Ar DA6} in the formula (D-B) .
*** is, ^{Ar DA3} in the formula (D-A), ^{Ar DA3} in the formula (D-B), ^{Ar DA5} in the formula (D-B), or, the bond between ^{Ar DA7} in the formula (D-B) Represent.
R ^DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of ^RDA , they may be the same or different.

R ^DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have a substituent. May be.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably groups represented by the formula (ArDA-1), (ArDA-2) or (ArDA-3) (hereinafter referred to as “ArDA-3”). In some cases, it is referred to as “groups represented by formulas (ArDA-1) to (ArDA-3)”).

Where
R ^DA represents the same meaning as described above.
R ^DB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of ^RDBs , they may be the same or different.

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

T ^DA is preferably represented by the formula (TDA-1), (TDA -2) or (TDA-3) a group represented by (hereinafter also "formula (TDA-1) ~ (TDA -3) The group is called.
).

In the formula, R ^DA and R ^DB represent the same meaning as described above.

  The group represented by the formula (DA) is preferably a group represented by the formula (D-A1), (D-A2) or (D-A3) (hereinafter sometimes referred to as “formula (D-A1)”). To a group represented by (D-A3).

Where
R ^p1 , R ^p2 and R ^p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p1 and R ^p2 , they may be the same or different.
n ^p1 represents an integer of 0 to 5, n ^p2 represents an integer of 0 to ³ , and n ^p3 represents 0 or 1. A plurality of n ^p1 may be the same or different.

  The group represented by the formula (D-B) is preferably a group represented by the formula (D-B1), (D-B2) or (D-B3) (hereinafter sometimes referred to as “formula (D-B1)”. To a group represented by (D-B3).

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

  np1 is preferably 0 or 1, more preferably 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0.

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

In the phosphorescent compound represented by the formula (1-A), the anionic bidentate ligand represented by A ¹ -G ¹ -A ² may be a ligand represented by the following: Good.

Where
* Represents a site that binds to M.
R ^L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a halogen atom, and these groups optionally have a substituent. A plurality of R ^L1 may be the same or different.

  The phosphorescent compound represented by the formula (1-A) includes the phosphorescent compound represented by the formula (1-A1), the phosphorescent compound represented by the formula (1-A2), the formula (1- A phosphorescent compound represented by A3) or a phosphorescent compound represented by formula (1-A4) is preferred.

In the formula, M, n ¹ , n ² , R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A , R ^24A and A ¹ -G ¹ -A ² are M in formula (1-A). , N ¹ , n ² , R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A , R ^24A and A ¹ -G ¹ -A ² .

  Examples of the phosphorescent compound represented by the formula (1-A) include a phosphorescent compound represented by the following formula.

[Phosphorescent Compound Represented by Formula (1-B)]
Phosphorescent compound represented by the formula (1-B) is defined and M is a central metal, and a ligand which is defined the number of index n ^1, the number of index n ² And is composed of a ligand.

Illustrative and preferred embodiments of M, n ¹ , n ² and A ¹ -G ¹ -A ^{2 in} the phosphorescent compound represented by the formula (1-B) include phosphorescence represented by the formula (1-A) Examples of M, n ¹ , n ² and A ¹ -G ¹ -A ^{2 in} the light-emitting compound are the same as the exemplified and preferred embodiments.

At least one selected from the group consisting of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is represented by an aryl group, a monovalent heterocyclic group or a substituted amino group. These groups are preferable, and these groups may have a substituent.

When the ring L ^1B is a pyrimidine ring, a pyrimidine ring in which E ^11B is a nitrogen atom or a pyrimidine ring in which E ^13B is a nitrogen atom is preferable, and a pyrimidine ring in which E ^11B is a nitrogen atom is more preferable.

R ^11B , R ^12B , R ^13B and R ^14B are each independently preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cyclo An alkyl group or an aryl group is more preferable, and a hydrogen atom, an alkyl group, or an aryl group is still more preferable.

When R ^11B , R ^12B , R ^13B and R ^14B are an aryl group, a monovalent heterocyclic group or a substituted amino group, R ^11B or R ^13B is an aryl group, a monovalent heterocyclic group or a substituted amino group. It is more preferable that R ^11B is an aryl group, a monovalent heterocyclic group or a substituted amino group. These groups are preferably dendrons because the power efficiency of the light emitting device is more excellent. Examples and preferred embodiments of the dendron include the same as the examples and preferred embodiments of the dendron in the phosphorescent compound represented by the formula (1-A).

When ring L ^2B is a pyridine ring, a pyridine ring in which E ^21B is a nitrogen atom, a pyridine ring in which E ^22B is a nitrogen atom, or a pyridine ring in which E ^23B is a nitrogen atom is preferable, and E ^22B is a nitrogen atom. A certain pyridine ring is more preferable.

When ring L ^2B is a pyrimidine ring, a pyrimidine ring in which E ^21B and E ^23B are nitrogen atoms or a pyrimidine ring in which E ^22B and E ^24B are nitrogen atoms is preferable, and E ^22B and E ^24B are nitrogen atoms. A pyrimidine ring is more preferred.

Ring L ^2B is preferably a benzene ring.

R ^21B , R ^22B , R ^23B and R ^24B are each independently preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, a hydrogen atom, an alkyl group, a cyclo An alkyl group or an aryl group is more preferable, and a hydrogen atom, an alkyl group, or an aryl group is still more preferable.

When R ^21B , R ^22B , R ^23B , and R ^24B are an aryl group, a monovalent heterocyclic group, or a substituted amino group, the power efficiency of the light-emitting element is more excellent, so that it is preferably a dendron. Examples and preferred embodiments of the dendron include the same as the examples and preferred embodiments of the dendron in the phosphorescent compound represented by the formula (1-A).

In the phosphorescent compound represented by the formula (1-B), the anionic bidentate ligand represented by A ¹ -G ¹ -A ² may be a ligand represented by the following: Good.

Where
* Represents a site that binds to M.
R ^L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or a halogen atom, and these groups optionally have a substituent. Plural RL1s may be the same or different.
R ^L2 represents an alkyl group, a cycloalkyl group, or a halogen atom, and these groups optionally have a substituent.

  The phosphorescent compound represented by the formula (1-B) is a phosphorescent compound represented by the formula (1-B1), a phosphorescent compound represented by the formula (1-B2), or the formula (1- A phosphorescent compound represented by B3) is preferred.

Where
M, n ¹ , n ² , R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B , R ^24B and A ¹ -G ¹ -A ² are respectively in the formula (1-B). It represents ^{M, n 1, n 2,} R 11B, R 12B, R 13B, R 14B, R 21B, R 22B, R 23B, the same meaning as ^{R 24B} and ^a 1 ^-G 1 -A ^2.
n ³ and n ⁴ each independently represent an integer of 1 to 2, and n ³ + n ⁴ is 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ³ + n ⁴ is 3, and when M is a palladium atom or a platinum atom, n ³ + n ⁴ is 2.
R ^15B , R ^16B , R ^17B and R ^18B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, halogen atom Alternatively, it represents a substituted amino group, and these groups optionally have a substituent. When there are a plurality of R ^15B , R ^16B , R ^17B and R ^18B , they may be the same or different. R ^13B and R ^15B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , R ^18B and R ^21B may be bonded to each other to form a ring together with the atoms to which they are bonded. .

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

  The phosphorescent compound used for forming the first organic layer is, for example, JP-T-2004-530254, JP-A-2008-179617, JP-A-2011-105701, JP-T-2007-504272, It can be synthesized according to the methods described in JP2013-147449A and JP2013-147450A.

[Host material]
Since the power efficiency of the light emitting device according to this embodiment is excellent, the first organic layer of the light emitting device according to this embodiment includes at least one phosphorescent compound, hole injecting property, hole transporting property, electron A layer formed using a composition containing a host material having at least one function selected from the group consisting of an injecting property and an electron transporting property is preferable. In the composition, the host material may be contained singly or in combination of two or more.

  That is, the first organic layer may be a layer further containing a host material having at least one function selected from the group consisting of hole injecting property, hole transporting property, electron injecting property, and electron transporting property. The first organic layer has at least one phosphorescent compound and a host material having at least one function selected from the group consisting of a hole injecting property, a hole transporting property, an electron injecting property, and an electron transporting property. It may be a layer composed of a composition containing

  In the composition containing the phosphorescent compound and the host material, the total content of the phosphorescent compound is usually 0.1 to 50 when the total of the phosphorescent compound and the host material is 100 parts by mass. It is a mass part, Preferably it is 1-45 mass part, More preferably, it is 5-40 mass part.

Since the lowest excited triplet state (T ₁ ) of the host material is excellent in power efficiency of the light emitting device according to this embodiment, it is equivalent to T ₁ of the phosphorescent compound used for forming the first organic layer. An energy level or a higher energy level is preferable.

  As the host material, since the light-emitting element according to this embodiment can be manufactured by a solution coating process, it exhibits solubility in a solvent capable of dissolving the phosphorescent compound used for forming the first organic layer. It is preferable.

  Host materials are classified into low molecular compounds and high molecular compounds.

[Low molecular host]
A low molecular compound (hereinafter referred to as “low molecular host”) preferable as a host material will be described below. The low molecular host is a compound having no molecular weight distribution and having a molecular weight of 1 × 10 ⁴ or less among the above host materials.

  The low molecular host is preferably a compound represented by the formula (H-1).

Where
Ar ^H1 and Ar ^H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
n ^H1 and n ^H2 each independently represent 0 or 1. When a plurality of n ^H1 are present, they may be the same or different. When a plurality of n ^H2 are present, they may be the same or different.
n ^H3 represents an integer of 0 or more.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R ^H11 ) ₂ ] n ^H11 —, and these groups ^optionally have a substituent. When a plurality of L ^H1 are present, they may be the same or different.
n ^H11 represents an integer of 1 to 10. 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. A plurality of R ^H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
L ^H2 represents a group represented by -N (-L ^H21 -R ^H21 )-. When a plurality of L ^H2 are present, they may be the same or different.
L ^H21 represents a single bond, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. R ^H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.

Ar ^H1 and Ar ^H2 are phenyl group, fluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, thienyl group, benzothienyl group, dibenzothienyl group, furyl group, benzofuryl Group, dibenzofuryl group, pyrrolyl group, indolyl group, azaindolyl group, carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group, phenyl group, spirobifluorenyl group, A pyridyl group, pyrimidinyl group, triazinyl group, dibenzothienyl group, dibenzofuryl group, carbazolyl group or azacarbazolyl group is more preferable, and a phenyl group, pyridyl group, carbazolyl group or azacarbazolyl group is further preferable. It is particularly preferably a group represented by the above formula (TDA-1) or (TDA-3), particularly preferably a group represented by the above formula (TDA-3). It may have a substituent.

As the substituent that Ar ^H1 and Ar ^H2 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable, and an alkyl group, a cyclo An alkoxy group, an alkoxy group or a cycloalkoxy group is more preferable, an alkyl group or a cycloalkoxy group is more preferable, and these groups may further have a substituent.

n ^H1 is preferably 1. n ^H2 is preferably 0.

n ^H3 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 1 to 3, and particularly preferably 1.

^nH11 is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 1.

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

L ^H1 is preferably an arylene group or a divalent heterocyclic group.

L ^H1 is represented by formulas (A-1) to (A-3), (A-8) to (A-10), (AA-1) to (AA-6), (AA-10) to (AA-). 21) or a group represented by (AA-24) to (AA-34), preferably represented by formulas (A-1), (A-2), (A-8), (A-9), It is more preferably a group represented by (AA-1) to (AA-4), (AA-10) to (AA-15) or (AA-29) to (AA-34). -1), (A-2), (A-8), (A-9), (AA-2), (AA-4), groups represented by (AA-10) to (AA-15) It is more preferable that Formula (A-1), (A-2), (A-8), (AA-2), (AA-4), (AA-10), (AA-12) or A group represented by (AA-14) is particularly preferred, A group represented by formula (A-1), (A-2), (AA-2), (AA-4) or (AA-14) is particularly preferable.

As the substituent that L ^H1 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable, and an alkyl group, an alkoxy group, an aryl group is preferable. A group or a monovalent heterocyclic group is more preferable, an alkyl group, an aryl group or a monovalent heterocyclic group is further preferable, and these groups may further have a substituent.

L ^H21 is preferably a single bond or an arylene group, more preferably a single bond, and this arylene group may have a substituent.

The definition and examples of the arylene group or divalent heterocyclic group represented by L ^H21 are the same as the definitions and examples of the arylene group or divalent heterocyclic group represented by L ^H1 .

R ^H21 is preferably an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.

The definitions and examples of the aryl group and monovalent heterocyclic group represented by R ^H21 are the same as the definitions and examples of the aryl group and monovalent heterocyclic group represented by Ar ^H1 and Ar ^H2 .

Definitions and examples of the substituent that R ^H21 may have are the same as the definitions and examples of the substituent that Ar ^H1 and Ar ^H2 may have.

  The compound represented by the formula (H-1) is preferably a compound represented by the formula (H-2).

In the formula, Ar ^H1 , Ar ^H2 , n ^H3 and L ^H1 represent the same meaning as described above.

  Examples of the compound represented by the formula (H-1) include the following formulas (H-101), (H-102), (H-103), (H-104), (H-105), (H -106), (H-107), (H-108), (H-109), (H-110), (H-111), (H-112), (H-113), (H-114) ), (H-115), (H-116), (H-117) or (H-118) (hereinafter referred to as “formulas (H-101) to (118)"). Compound ").

[Polymer host]
A polymer compound preferable as a host material (hereinafter referred to as “polymer host”) will be described below. The polymer host is a polymer having a molecular weight distribution among the host materials and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ to 1 × 10 ⁸ .

  Examples of the polymer host include a polymer compound that is a hole transport material described later and a polymer compound that is an electron transport material described later.

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

In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. The group may have a substituent.

The arylene group represented by Ar ^Y1 is more preferably a formula (A-1), (A-2), (A-6) to (A-10), (A-19) or (A-20). A group represented by formula (A-1), (A-2), (A-7), (A-9) or (A-19), These groups may have a substituent.

More preferably, the divalent heterocyclic group represented by Ar ^Y1 is represented by the formulas (AA-1) to (AA-4), (AA-10) to (AA-15), (AA-18) to ( AA-21), a group represented by (AA-33) or (AA-34), and more preferably a group represented by formulas (AA-4), (AA-10), (AA-12), (AA- 14) or a group represented by (AA-33), and these groups may have a substituent.

More preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded, and further preferable. The ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar ^Y1 described above.

  Examples of the “divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded” include groups represented by the following formulas, which have a substituent. You may do it.

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 optionally have a substituent.

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

  Examples of the structural unit represented by the formula (Y) include formulas (Y-1), (Y-2), (Y-3), (Y-4), (Y-5), and (Y-6). ), (Y-7), (Y-8), (Y-9), or (Y-10) (hereinafter, represented by the formulas (Y-1) to (Y-10). From the viewpoint of the luminance life of the light emitting device according to this embodiment, preferably, the structural units are represented by formulas (Y-1) to (Y-3). From the viewpoint of the electron transport property of the light emitting device according to the present embodiment, it is preferably a structural unit represented by formulas (Y-4) to (Y-7), and hole transport of the light emitting device according to the present embodiment. From the viewpoint of property, it is preferably a structural unit represented by formulas (Y-8) to (Y-10).

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

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

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

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

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

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

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

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ₂ — is preferably such that both are alkyl groups or cycloalkyl groups, both are aryl groups, and both are monovalent complex A cyclic group, or one is an alkyl group or a cycloalkyl group and the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group and the other is an aryl group. May have a substituent. Two R ^{Y2 s} may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y2 forms a ring, the group represented by —C (R ^Y2 ) ₂ — Is preferably a group represented by the formula (Y-A1), (Y-A2), (Y-A3), (Y-A4) or (Y-A5), more preferably the formula (Y-A4). ), And these groups may have a substituent.

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ═C (R ^Y2 ) — is preferably both an alkyl group or a cycloalkyl group, or one of which is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group, and these groups optionally have a substituent.

In ^XY1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded. When R ^Y2 forms a ring, —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — The group represented is preferably a group represented by the formula (Y-B1), (Y-B2), (Y-B3), (Y-B4) or (Y-B5), more preferably the formula It is a group represented by (Y-B3), and these groups may have a substituent.

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

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

In the formula, R ^Y11 and X ^Y1 represent the same meaning as described above.

In the formula, R ^Y1 and X ^Y1 represent the same meaning as described above.

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

In the formula, R ^Y11 and X ^Y1 represent the same meaning as described above.

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

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

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

In the formula, R ^Y11 and R ^Y3 represent the same meaning as described above.

In the formula, R ^Y1 represents the same meaning as described above. R ^Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.

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

As the structural unit represented by the formula (Y), for example, the formula (Y-101), (Y-102), (Y-103), (Y-104), (Y-105), (Y-106) ), (Y-107), (Y-108), (Y-109), (Y-110), (Y-111), (Y-112), (Y-113), (Y-114), An arylene group represented by (Y-115), (Y-116), (Y-117), (Y-118), (Y-119), (Y-120) or (Y-121) (hereinafter, In some cases, a structural unit consisting of “arylene groups represented by formulas (Y-101) to (Y-121)”), formulas (Y-201), (Y-202), (Y-203), ( Y-204), (Y-205) or (Y-206) represented by a divalent heterocyclic group (hereinafter referred to as “formula (Y-201) (Y-206) 2-valent called heterocyclic group "represented by.
), A formula (Y-301), (Y-302), (Y-303) or (Y-304) (hereinafter sometimes referred to as “formulas (Y-301) to (Y-304)”) And a structural unit composed of a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other.

When the constituent unit represented by the formula (Y) and Ar ^Y1 is an arylene group is contained in a predetermined amount, the luminance life of the light emitting element tends to be more excellent. For this reason, the polymer compound is 0.5 mol% or more and 80 mol% or less (preferably 30 mol% or more and 60 mol% or less) of the monomer constituting the structural unit with respect to the total amount of monomers forming the polymer compound. ) Is preferably polymerized at a ratio of

A structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group directly bonded to each other. When the constituent unit which is the group is contained in a predetermined amount, the charge transport property of the light emitting element tends to be more excellent. For this reason, the polymer compound is 0.5 mol% or more and 30 mol% or less (preferably 3 mol% or more and 20 mol% or less) of the polymer constituting the structural unit with respect to the total amount of monomers forming the polymer compound. ) Is preferably polymerized at a ratio of

  One type of structural unit represented by the formula (Y) may be contained in the polymer host, or two or more types may be contained.

  Since the polymer host is excellent in hole transportability, it is preferable that the polymer host further includes a structural unit represented by the following formula (X).

Where
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 optionally 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 to each other. And these groups may have a substituent. When a plurality of 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 a plurality of R ^X2 and R ^X3 are present, they may be the same or different.

a ^X1 is preferably 2 or less, more preferably 1, because the luminance lifetime of the light emitting device according to the present embodiment is more excellent.

a ^X2 is preferably 2 or less, more preferably 0, because the luminance lifetime of the light emitting device according to this embodiment is more excellent.

R ^X1 , R ^X2 and R ^X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. Also good.

The arylene group represented by Ar ^X1 and Ar ^X3 is more preferably a group represented by the formula (A-1) or (A-9), and still more preferably a group represented by the formula (A-1). And these groups may have a substituent.

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

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

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

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

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

As the divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one divalent heterocyclic group are directly bonded, at least represented by Ar ^Y1 in the formula (Y) Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.

Ar ^X2 and Ar ^X4 are preferably an arylene group which may have a substituent.

The substituents that the groups represented by Ar ^{X1 to} Ar ^X4 and R ^{X1 to} R ^X3 may have are preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups further have a substituent. You may do it.

  The structural unit represented by the formula (X) is preferably the formula (X-1), (X-2), (X-3), (X-4), (X-5), (X-6). Or a structural unit represented by (X-7) (hereinafter sometimes referred to as “structural units represented by formulas (X-1) to (X-7)”), and more preferably represented by formula (X—). 1) to structural units represented by (X-6), more preferably structural units represented by formulas (X-3) to (X-6).

In the formula, 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 group. These groups may have a substituent. A plurality of R ^X4 may be the same or different. A plurality of R ^X5 may be the same or different, and adjacent R ^X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

  The structural unit represented by the formula (X) is preferably contained in a predetermined amount of the polymer host because of its excellent hole transportability. That is, the polymer host is 0.1 mol% or more and 50 mol% or less (more preferably 1 mol) of the monomer that forms the structural unit represented by the formula (X) with respect to the total amount of monomers forming the polymer host. The polymer is preferably polymerized at a ratio of from mol% to 40 mol%, more preferably from 5 mol% to 30 mol%.

  Examples of the structural unit represented by formula (X) include formulas (X1-1), (X1-2), (X1-3), (X1-4), (X1-5), and (X1-6). ), (X1-7), (X1-8), (X1-9), (X1-10) or (X1-11) (hereinafter referred to as “formula (X1-1) ˜ And a structural unit represented by the formulas (X1-3) to (X1-10).

  In the polymer host, only one type of structural unit represented by the formula (X) may be included, or two or more types of structural units may be included.

  Examples of the polymer host include polymer compounds (P-1), (P-2), (P-3), (P-4), (P-5) and (P-6) in Table 1. Can be mentioned.

  In Table 1, p, q, r, s, and t show the molar ratio of each structural unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70. “Other” means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).

  The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A copolymer obtained by polymerization is preferred.

[Method for producing polymer host]
The polymer host can be produced by using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), etc., and the Suzuki reaction, the Yamamoto reaction, the Buchwald, and the like. Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, a Stille reaction, a Negishi reaction and a Kumada reaction.

  In the above polymerization method, as a method of charging the monomer, a method in which the entire amount of the monomer is charged all at once into the reaction system, after a part of the monomer is charged and reacted, the remaining monomers are batched, Examples thereof include a method of charging continuously or divided, a method of charging monomer continuously or divided, and the like.

  Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst.

  Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination. When the purity of the polymer host is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, or the like.

[Composition of the first organic layer]
The first organic layer is composed of at least one phosphorescent compound and the aforementioned host material, hole transport material, hole injection material, electron transport material, electron injection material, light emitting material, antioxidant and solvent. It may be a layer formed using a composition containing at least one material selected from the group (hereinafter also referred to as “composition of the first organic layer”). Further, the first organic layer may be a layer containing the composition of the first organic layer.

[Hole transport material]
The hole transport material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound. The hole transport material may have a crosslinking group.

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

  In the composition of the first organic layer, the compounding amount of the hole transport material is usually 1 to 400 parts by mass when the phosphorescent compound used for forming the first organic layer is 100 parts by mass. The amount is preferably 5 to 150 parts by mass.

  A hole transport material may be used individually by 1 type, or may use 2 or more types together.

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

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

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

  In the composition of the first organic layer, the compounding amount of the electron transport material is usually 1 to 400 parts by mass when the phosphorescent compound used for forming the first organic layer is 100 parts by mass, Preferably it is 5-150 mass parts.

  An electron transport material may be used individually by 1 type, or may use 2 or more types together.

[Hole injection material and electron injection material]
The hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively. The hole injection material and the electron injection material may have a crosslinking group.

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

  Examples of the polymer compound include 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. A functional polymer.

  In the composition of the first organic layer, the compounding amounts of the hole injecting material and the electron injecting material are usually 1 when the phosphorescent compound used for forming the first organic layer is 100 parts by mass, respectively. It is -400 mass parts, Preferably it is 5-150 mass parts.

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

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

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

  Doping ions may be used alone or in combination of two or more.

[Luminescent material]
Luminescent materials (different from the phosphorescent compound used for forming the first organic layer) are classified into low molecular compounds and high molecular compounds. The light emitting material may have a crosslinking group.

  Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, and perylene and derivatives thereof.

  Examples of the polymer compound include phenylene group, naphthalenediyl group, anthracenediyl group, fluorenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, group represented by formula (X), carbazole diyl group, phenoxazine diyl. Group, a phenothiazinediyl group, a pyrenediyl group, and the like.

  In the composition of the first organic layer, the blending amount of the light emitting material is usually 1 to 400 parts by mass, preferably 100 parts by mass, preferably 100 parts by mass of the phosphorescent compound used for forming the first organic layer. Is 5 to 150 parts by mass.

  A luminescent material may be used individually by 1 type, or may use 2 or more types together.

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the phosphorescent compound and does not inhibit light emission and charge transport, and examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

  In the composition of the first organic layer, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the phosphorescent compound used for forming the first organic layer is 100 parts by mass. is there.

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

[Ink for first organic layer]
The composition of the first organic layer containing the solvent (hereinafter also referred to as “ink for the first organic layer”) is formed by spin coating, casting, micro gravure coating, gravure coating, bar coating. Suitable for coating methods such as roll coating, wire bar coating, dip coating, spray coating, screen printing, flexographic printing, offset printing, ink jet printing, capillary coating, nozzle coating, etc. can do.

  The viscosity of the ink for the first organic layer may be adjusted according to the type of coating method. However, when a solution such as an ink jet printing method is applied to a printing method via a discharge device, clogging during ejection Since flight bending is difficult to occur, it is preferably 1 to 20 mPa · s at 25 ° C.

  The solvent contained in the ink for the first organic layer is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples of the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as THF (tetrahydrofuran), dioxane, anisole, and 4-methylanisole. Aromatic hydrocarbon solvents such as toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane Aliphatic hydrocarbon solvents such as acetone, methyl ethyl ketone, cyclohexanone, acetophenone; ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, acetic acid Ester solvents such as phenyl; polyhydric alcohol solvents such as ethylene glycol, glycerin and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2 Examples include amide solvents such as -pyrrolidone and N, N-dimethylformamide. A solvent may be used individually by 1 type, or may use 2 or more types together.

  In the ink for the first organic layer, the blending amount of the solvent is usually 1000 to 100000 parts by mass, preferably 100 to 100 parts by mass, preferably 100 parts by mass of the phosphorescent compound used for forming the first organic layer. It is 2000-20000 mass parts.

<Second organic layer>
The second organic layer is a layer formed using a polymer composition in which one or more polymer compounds are blended. At least one of the polymer compounds is a polymer compound having a crosslinking group (specifically, at least one of the polymer compounds is a polymer compound containing a structural unit having a crosslinking group) (hereinafter referred to as “crosslinking”). Also referred to as a functional polymer compound). Further, at least one of the above polymer compounds is a polymer compound containing a phosphorescent structural unit (hereinafter also referred to as “phosphorescent polymer compound”). The second organic layer preferably contains a polymer cured product formed from the polymer composition.

  In the present embodiment, one kind of polymer compound may have both a phosphorescent constituent unit and a crosslinking group (specifically, one kind of polymer compound includes a phosphorescent constituent unit, and And may contain both structural units having a crosslinking group). That is, the polymer compound is a polymer compound having a phosphorescent constituent unit and a crosslinking group (specifically, a polymer compound containing a phosphorescent constituent unit and a constituent unit having a crosslinking group) (hereinafter, (Also referred to as “crosslinkable phosphorescent polymer compound”).

  In the present embodiment, different polymer compounds may each have a phosphorescent constituent unit and a crosslinking group (specifically, different polymer compounds each have a phosphorescent constituent unit, and And may contain a structural unit having a crosslinking group). That is, the polymer compound may include at least two kinds of a phosphorescent polymer compound and a crosslinkable polymer compound.

In a preferred embodiment, the polymer compound (one or more polymer compounds including a crosslinkable polymer compound) is a total of all monomer units for each monomer unit constituting the polymer compound. A value x obtained by multiplying the molar ratio C of the monomer unit to the mole by the molecular weight M of the monomer unit, and a value obtained by multiplying the molar ratio C and the number n of crosslinking groups of the monomer unit. When y is obtained, the value of (Y ₁ × 1000) / X ₁ calculated from the sum X _{1 of} x and the sum Y _{1 of} y is 0.6 or more.

When the second organic layer is a layer formed using a kind of polymer compound (crosslinkable phosphorescent polymer compound), for each monomer unit constituting the kind of polymer compound, A value x obtained by multiplying the molar ratio C of the monomer unit to the total mole of all monomer units constituting the polymer compound and the molecular weight M of the monomer unit, and the molar ratio C and the monomer When the value y obtained by multiplying the number n of bridging groups of the unit is obtained, the value of (Y ₁ × 1000) / X ₁ calculated from the sum X _{1 of} x and the sum Y _{1 of} y is 0.6. That's it.

Using the polymer composition in which the second organic layer is blended with two or more polymer compounds (two or more polymer compounds including a crosslinkable polymer compound and a phosphorescent polymer compound). In the case of a layer to be formed, the weighted average of the values of (Y ₁ × 1000) / X ₁ obtained for each polymer compound (average value from the blending ratio of two or more polymer compounds) is 0. 6 or more.

  A polymer composition in which the second organic layer contains a crosslinkable polymer compound having a crosslinkable group and a polymer compound having no crosslinkable group (specifically, a phosphorescent polymer compound). In the case of the layer formed by using, the polymer compound having no crosslinking group is selected from the group consisting of the structural unit represented by the formula (Y) and the structural unit represented by the formula (X), for example. And a polymer compound containing at least one structural unit.

[Crosslinkable polymer compound]
The crosslinkable polymer compound is preferably a polymer compound having at least one crosslinking group selected from the crosslinking group A group because the power efficiency of the light emitting device according to this embodiment is excellent.

  As the bridging group selected from the bridging group A group, since the power efficiency of the light emitting device according to this embodiment is more excellent, preferably the formulas (XL-1), (XL-3), (XL-9), ( XL-16) or a crosslinkable group represented by (XL-17), more preferably a crosslinkable group represented by the formula (XL-1), (XL-16) or (XL-17), More preferably, it is a crosslinking group represented by the formula (XL-1) or (XL-17).

The crosslinkable polymer compound is also referred to as a structural unit having a crosslinking group (hereinafter also referred to as “crosslinked structural unit”).
). The crosslinked structural unit is preferably a structural unit represented by the following formula (2) or (3), but may be a structural unit represented by the following formula.

  The crosslinkable polymer compound preferably has a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group, and the cross-linking structural unit is a structural unit represented by the formula (2) or the formula (3 It is preferable that it is a structural unit represented by.

Where
nA represents an integer of 0 to 5, and n represents 1 or 2.
Ar ¹ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of ^LA are present, they may be the same or different.
X represents a crosslinking group selected from the crosslinking group A group. When two or more X exists, they may be the same or different.

  nA is preferably 0 or 1, more preferably 0, because the power efficiency of the light emitting device according to this embodiment is excellent.

  n is preferably 2 because the power efficiency of the light emitting device according to this embodiment is excellent.

Ar ¹ is preferably an aromatic hydrocarbon group which may have a substituent since the power efficiency of the light emitting device according to this embodiment is excellent.

In the aromatic hydrocarbon group represented by Ar ¹ , the number of carbon atoms constituting the aromatic ring is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18.

The arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar ¹ is preferably a group represented by formulas (A-1) to (A-20), more preferably. A group represented by formula (A-1), (A-2), (A-6) to (A-10), (A-19) or (A-20), and more preferably A-1), a group represented by (A-2), (A-7), (A-9) or (A-19). These groups may have a substituent.

In the heterocyclic group represented by Ar ¹ , the number of carbon atoms constituting the heterocyclic ring and the condensed ring with the heterocyclic ring is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15.

The divalent heterocyclic group portion excluding n substituents of the heterocyclic group represented by Ar ¹ is preferably a group represented by the formulas (AA-1) to (AA-34).

The aromatic hydrocarbon group and heterocyclic group represented by Ar ¹ may have a substituent. Examples of the substituent that the aromatic hydrocarbon group and the heterocyclic group may have include, for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, and a monovalent A heterocyclic group and a cyano group are mentioned.

L ^A number of carbon atoms of the alkylene group represented by the not including the carbon atom number of substituent is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3. The number of carbon atoms a cycloalkylene group represented by L ^A is not including the carbon atom number of substituent is usually 3 to 10.

The alkylene group represented by L ^A, for example, methylene group, ethylene group, propylene group, butylene group, hexylene group, and octylene group. Alkylene group represented by L ^A may have a substituent, and examples of the substituent, for example, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom and a cyano group.

The cycloalkylene group represented by L ^A, for example, cyclohexylene, and cyclopentylene. Cycloalkylene group represented by L ^A may have a substituent, and examples of the substituent, for example, include an alkyl group, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom and a cyano group It is done.

The aryl group represented by L ^A may have a substituent. Examples of the aryl group include o-phenylene, m-phenylene, and p-phenylene. Examples of the substituent that the aryl group may have include, for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, and a bridge. Examples thereof include a crosslinking group selected from the group A.

L ^A is preferably a phenylene group or a methylene group because the synthesis of the crosslinking group-containing polymer compound is facilitated, and these groups may have a substituent.

  The preferred range, more preferred range and even more preferred range of the crosslinking group represented by X are the same as the preferred range, more preferred range and further preferred range of the crosslinking group selected from the aforementioned crosslinking group A group.

  As for the structural unit represented by Formula (2), only 1 type may be contained in the crosslinking group containing high molecular compound, and 2 or more types may be contained.

Where
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When a plurality of mA are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar ² and Ar ⁴ each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ² , Ar ³ and Ar ⁴ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom, to form a ring. It may be.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR '' - represents a group represented by an oxygen atom or a sulfur atom in these groups have a substituent May be. R ″ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of K ^A are present, they may be the same or different.
X ′ represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of X ′ are present, they may be the same or different. However, at least one X ′ is a bridging group.

  mA is preferably 0 or 1, more preferably 0, because the power efficiency of the light emitting device according to this embodiment is excellent.

  m is preferably 2 because the power efficiency of the light emitting device according to this embodiment is excellent.

  c is preferably 0 because it facilitates the synthesis of the crosslinkable group-containing polymer compound and the power efficiency of the light emitting device according to this embodiment is excellent.

Ar ³ is preferably an aromatic hydrocarbon group which may have a substituent since the power efficiency of the light emitting device according to this embodiment is excellent.

The definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar ³ are the same as the definition and example of the arylene group represented by Ar ^X2 in the above formula (X). It is.

The definition and example of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar ³ are the divalent heterocyclic group represented by Ar ^X2 in the above formula (X). Same as definition and example of part.

The definition and examples of the divalent group excluding m substituents of the group in which at least one aromatic hydrocarbon ring represented by Ar ³ and at least one heterocycle are directly bonded are defined by the above formula ( The definition and examples of the divalent group in which at least one kind of arylene group represented by Ar ^X2 and at least one kind of divalent heterocyclic group in X) are directly bonded are the same.

Ar ² and Ar ⁴ are preferably an arylene group which may have a substituent since the luminance lifetime of the light emitting device according to this embodiment is more excellent.

The definitions and examples of the arylene group represented by Ar ² and Ar ⁴ are the same as the definitions and examples of the arylene group represented by Ar ^X1 and Ar ^X3 in the above formula (X).

The definitions and examples of the divalent heterocyclic group represented by Ar ² and Ar ⁴ are the same as the definitions and examples of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 in the aforementioned formula (X). is there.

The groups represented by Ar ² , Ar ³ and Ar ⁴ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, Examples thereof include a halogen atom, a monovalent heterocyclic group, and a cyano group.

Alkylene group represented by K ^A, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by L ^A, a cycloalkylene group, an arylene group, a divalent heterocyclic The definition and examples of the ring group are the same.

K ^A, since the synthesis of the crosslinking group-containing polymer compound is facilitated, preferably, a phenylene group or methylene group, and these groups may have a substituent.

  The preferred range, more preferred range and further preferred range of the crosslinking group represented by X ′ are the same as the preferred range, more preferred range and further preferred range of the crosslinking group selected from the aforementioned crosslinking group A group.

  As for the structural unit represented by Formula (3), only 1 type may be contained in the crosslinkable polymer compound, and 2 or more types may be contained.

  Examples of the structural unit represented by the formula (2) include the formulas (2-1), (2-2), (2-3), (2-4), (2-5), and (2-6). ), (2-7), (2-8), (2-9), (2-10), (2-11), (2-12), (2-13), (2-14), (2-15), (2-16), (2-17), (2-18), (2-19), (2-20), (2-21), (2-22), (2 -23), (2-24), (2-25), (2-26), (2-27), (2-28), (2-29), (2-30) or (2-31) ) (Hereinafter, referred to as “structural units represented by formulas (2-1) to (2-31)” in some cases). Examples of the structural unit represented by formula (3) include formulas (3-1), (3-2), (3-3), (3-4), (3-5), and (3-6). ), (3-7), (3-8) or (3-9) represented by a structural unit (hereinafter referred to as “structural units represented by formulas (3-1) to (3-9)” in some cases) Said).

  Among these, since the crosslinkability of the crosslinkable polymer compound is excellent, it is preferably a structural unit represented by the formulas (2-1) to (2-31), more preferably the formula (2-1). ~ (2-15), (2-19), (2-20), (2-23), (2-25), (2-27), (2-30) or (2-31) And more preferably represented by formulas (2-1) to (2-13), (2-20), (2-27), (2-30) or (2-31). And are particularly preferably represented by the formulas (2-1) to (2-9), (2-20), (2-27), (2-30) or (2-31). It is a structural unit.

  Since the crosslinkable polymer compound is excellent in hole transportability, it is preferable that the crosslinkable polymer compound further includes a structural unit represented by the formula (X).

  The definition and example of the structural unit represented by the formula (X) that the crosslinkable polymer compound may contain are the definition of the structural unit represented by the formula (X) that the above-described polymer host may contain. And the same as the example.

  Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably contained in a predetermined amount in the crosslinkable polymer compound. That is, the crosslinkable polymer compound contains 0.1 mol% or more and 70 mol% or less of the monomer that forms the structural unit represented by the formula (X) with respect to the total amount of monomers that form the crosslinkable polymer compound ( More preferably, it is polymerized at a ratio of 1 mol% to 60 mol%, more preferably 5 mol% to 50 mol%, and particularly preferably 5 mol% to less than 50 mol%.

  One type of structural unit represented by the formula (X) may be included in the crosslinkable polymer compound, or two or more types may be included.

  The crosslinkable polymer compound may further contain a structural unit represented by the formula (Y).

  The definition and examples of the structural unit represented by the formula (Y) that the crosslinkable polymer compound may contain are the definitions of the structural unit represented by the formula (Y) that the above-described polymer host may contain. And the same as the example.

  The structural unit represented by the formula (Y) is 0 mol% or more and 50 mol% or less of the monomer that forms the structural unit represented by the formula (Y) with respect to the total amount of monomers that form the crosslinkable polymer compound. It is preferable that the polymerization is performed at a ratio of (more preferably 0 mol% to 40 mol%, still more preferably 0 mol% to 30 mol%).

  One type of structural unit represented by the formula (Y) may be included in the crosslinkable polymer compound, or two or more types may be included.

  The crosslinkable polymer compound may further contain a structural unit represented by the formula (Y12).

Where
Ar ^Y12 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. A plurality of Ar ^Y12 may be the same or different.
q represents the integer of 1-5.
X ^Y12 represents an alkylene group, a cycloalkylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of ^XY12 are present, they may be the same or different.

The definition, examples, and preferred ranges of Ar ^Y12 in formula (Y12) are the same as Ar ^Y1 .

  Q in the formula (Y12) represents an integer of 1 to 5, preferably an integer of 1 to 3, more preferably an integer of 1 to 2, and further preferably 1.

X ^Y12 in formula (Y12) represents an alkylene group, a cycloalkylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. X ^Y12 is preferably an alkylene group or a cycloalkylene group. When a plurality of ^XY12 are present, they may be the same or different.

  The number of carbon atoms of the alkylene group does not include the number of carbon atoms of the substituent, and is usually 1 to 10, preferably 1 to 5, and more preferably 1 to 3. The number of carbon atoms of the cycloalkylene group is usually 3 to 10 without including the number of carbon atoms of the substituent.

  Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, and an octylene group. The alkylene group may have a substituent, and examples of the substituent include a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, and a cyano group.

  Examples of the cycloalkylene group include a cyclohexylene group and cyclopentylene. The cycloalkylene group may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, and a cyano group.

  The following are mentioned as an example of the structural unit represented by a formula (Y12).

  The structural unit represented by the formula (Y12) is 0 mol% or more and 50 mol% or less of the monomer that forms the structural unit represented by the formula (Y12) with respect to the total amount of monomers that form the crosslinkable polymer compound. It is preferable that the polymerization is performed at a ratio of (more preferably 0 mol% to 40 mol%, still more preferably 0 mol% to 30 mol%).

  One type of structural unit represented by the formula (Y12) may be included in the crosslinkable polymer compound, or two or more types may be included.

  The crosslinkable polymer compound is further at least selected from the group consisting of a structural unit represented by the formula (X), a structural unit represented by the formula (Y), and a structural unit represented by the formula (Y12). It may include a kind of structural unit.

  The crosslinkable polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. The copolymer is preferably a copolymer obtained by copolymerization of

[Phosphorescent polymer compound]
The phosphorescent polymer compound is a polymer compound containing a phosphorescent constituent unit. The phosphorescent structural unit means a structural unit containing a group obtained by removing a hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a compound from the phosphorescent compound. Examples of the phosphorescent compound include the phosphorescent compound used for forming the first organic layer described above.

  The phosphorescent polymer compound preferably contains at least one phosphorescent constituent unit selected from constituent units represented by the formula (1G), (2G), (3G) or (4G).

Where
M ^1G represents a group formed by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound.
L ¹ is an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, —C (R ^B ) = C (R ^B ) — Represents a group represented by the formula: -C≡C-, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. R ^B 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 ^RBs 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. When a plurality of L ¹ are present, they may be the same or different.
n ^a1 represents an integer of 0 or more.

R ^A is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups optionally have a substituent.

R ^B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, Alternatively, an alkyl group is more preferable, and a hydrogen atom is particularly preferable, and these groups may have a substituent.

L ¹ is preferably a group represented by —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, and is a group represented by —C (R ^B ) ₂ — or an arylene group. More preferably, it is more preferably an arylene group, and these groups may have a substituent.
Among these, a group represented by the formula (A-1) or (A-2) is preferable.

Suitable substituents that R ^A , R ^B and L ¹ may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, A halogen atom etc. are mentioned, These groups may have a substituent further.

^na1 is an integer of 0-10 normally, Preferably it is an integer of 0-5, More preferably, it is an integer of 0-2, More preferably, it is 0 or 1, Especially preferably, it is 0.

  When the phosphorescent polymer compound includes a structural unit represented by the formula (1G), the structural unit represented by the formula (1G) is a terminal structural unit.

  The “terminal structural unit” means a terminal structural unit of the polymer compound, and the terminal structural unit is preferably a structural unit derived from a terminal blocking agent in the production of the polymer compound. .

M ^1G is preferably a group represented by the formula (GM-1).

Where
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹¹ represents an integer of 1-2. n ¹² represents an integer of 0-1. However, n ¹¹ + n ¹² is 1 or 2. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹¹ + n ¹² is 2, and when M is a palladium atom or platinum atom, n ¹¹ + n ¹² is 1.
E ⁴ represents a carbon atom or a nitrogen atom. A plurality of E ⁴ may be the same or different.
Ring R ^1G and ring R ^1G1 represent a 6-membered aromatic heterocyclic ring, and the ring may have a substituent. When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When there are a plurality of rings R ^1G , they may be the same or different.
Ring R ^2G and Ring R ^2G1 represent a 5-membered or 6-membered aromatic carbocyclic ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and these rings have a substituent. Also good. When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings R ^2G are present, they may be the same or different. However, when the ring R ^2G is a 6-membered aromatic heterocyclic ring, E ⁴ is a carbon atom.
However, one of the ring R ^1G1 and the ring R ^2G1 has one bond.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different.

When M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹² is 0 or 1, and more preferably 0.

In the case where M is a palladium atom or a platinum atom, n ¹² is 0.

Ring R ^1G is preferably a 6-membered aromatic heterocycle having 1 or more and 4 or less nitrogen atoms as constituent atoms, and preferably a 6-membered ring having 1 or more and 2 or less nitrogen atoms as constituent atoms Is more preferably a pyridine ring, a diazabenzene ring, a quinoline ring or an isoquinoline ring, particularly preferably a pyridine ring, a quinoline ring or an isoquinoline ring, and these rings are substituted. It may have a group.

Ring R ^2G is preferably a 6-membered aromatic carbocyclic ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and is a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, diazabenzene. A ring, a pyrrole ring, a furan ring or a thiophene ring is more preferable, a benzene ring, a naphthalene ring or a fluorene ring is more preferable, and a benzene ring is particularly preferable. These rings have a substituent. It may be.

^Examples of the substituent that the ring R ^1G and the ring R ^2G may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, and a dendron. Preferably, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a dendron is more preferable, an alkyl group, a cycloalkyl group, an aryl group or a dendron is more preferable, an alkyl group, an aryl group or a dendron is particularly preferable, These groups may further have a substituent. When a plurality of substituents are present in the ring R ^1G and the ring R ^2G , they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.

More preferably, at least one ring selected from the group consisting of ring R ^1G and ring R ^2G is a phosphorescent compound having a dendron.

Of the rings R ^1G and R ^2G , the number of dendrons in at least one ring is preferably 1 to 3, more preferably 1 or 2, and still more preferably 1.

Of the ring R ^1G and the ring R ^2G, the dendron of at least one ring is a group represented by the formula (DA) or (DB), and m ^DA1 is an integer of 1 or more. In this case, Ar ^DA1 bonded to ring R ^1G and / or ring R ^2G is preferably a group represented by the formula (ArDA-1).

When ring R ^1G and ring R ^2G have a dendron possessed by at least one ring is a group represented by the formula (DA) or (DB) and m ^DA1 is 0, the ring ^{G DA} which bind to R ^1G and / or ring ^{R 2G} is, the formula (GDA-11), (GDA -12), is preferably a group represented by (GDA-14) or (GDA-15), A group represented by the formula (GDA-11) or (GDA-15) is more preferable.

Among the rings R ^1G and R ^2G, the dendron possessed by at least one ring is a group represented by the formula (D-A1), (D-A3), (D-B1) or (D-B3). It is preferable that it is a group represented by the formula (D-A1) or (D-A3).

In the formula (GM-1), at least one of the ligands (the ligand represented by ring R ^{1G -ring} R ^2G ) whose number is defined by the subscript n ¹¹ is represented by the formula (GM-L1 ), (GM-L2), (GM-L3) or a ligand represented by (GM-L4), preferably a coordination represented by the formula (GM-L1) or (GM-L2) More preferably a child.

Where
R ^{G1 to} R ^G8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and these groups are It may have a substituent. R ^G1 and ^{R G2, R G2} and ^{R G3, R G3} and ^{R G4, R G4} and ^{R G5, R G5} and ^{R G6, R G6} and ^{R G7, and, R G7} and ^{R G8} are each bound, You may form the ring with the atom which each couple | bonds.

R ^G1 , R ^G4 , R ^G5 and R ^G8 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group or a cycloalkoxy group, and a hydrogen atom, an alkyl group Alternatively, an aryl group is more preferable, a hydrogen atom or an alkyl group is more preferable, and a hydrogen atom is particularly preferable, and these groups may have a substituent.

R ^G2 , R ^G3 , R ^G6 and R ^G7 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or a dendron, More preferably, it is an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron, more preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron, and a hydrogen atom or a dendron. It is particularly preferred that these groups may have a substituent.

It is preferable that at least one of R ^{G1 to} R ^G8 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and R ^G2 , R ^G3 , More preferably, at least one of R ^G6 and R ^G7 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group or a dendron, and these groups are substituted It may have a group.

When the ligand represented by the formula (GM-L1) has a dendron, at least one of R ^G2 , R ^G3 , R ^G6 and R ^G7 is preferably a dendron, and at least one of R ^G2 and R ^G6 is More preferably, it is a dendron.

When the ligand represented by the formula (GM-L1) has an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or an aryloxy group, R ^G2 , R ^G3 , R ^G6 and R ^G7 are preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group, and at least one of R ^G2 and R ^G6 More preferably, one is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or an aryloxy group, and these groups may have a substituent.

In Formula (GM-1), when a plurality of ligands represented by Formula (GM-L1) are present, the plurality of R ^{G1 to} R ^G8 may be the same or different.

Where
R ^{G9 to} R ^G18 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and these groups are It may have a substituent. R ^G9 and ^{R G10, R G10} and ^{R G11, R G11} and ^{R G12, R G12} and ^{R G13, R G13} and ^{R G14, R G14} and ^{R G15, R G15} and ^{R G16, R G16} and ^{R G17} and, R ^G17 and R ^G18 may be bonded to each other to form a ring together with the atoms to which they are bonded.

R ^G9 , R ^{G11 to} R ^G15, and R ^G18 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, or a cycloalkoxy group, and a hydrogen atom, an alkyl group Alternatively, an aryl group is more preferable, a hydrogen atom or an alkyl group is more preferable, and a hydrogen atom is particularly preferable, and these groups may have a substituent.

R ^G10 , R ^G16 and R ^G17 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or a dendron, a hydrogen atom, an alkyl group, It is more preferably an aryl group, a monovalent heterocyclic group or a dendron, more preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron, and a hydrogen atom or a dendron. Particularly preferred, these groups may have a substituent.

It is preferable that at least one of R ^{G9 to} R ^G18 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and R ^G10 , R ^G16 and More preferably, at least one of R ^G17 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and these groups have a substituent. You may do it.

When the ligand represented by the formula (GM-L2) has a dendron, at least one of R ^G10 , R ^G16 and R ^G17 is preferably a dendron, and at least one of R ^G16 and R ^G17 is a dendron. More preferably, R ^G16 is a dendron.

When the ligand represented by the formula (GM-L2) has an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or an aryloxy group, R ^G10 , R ^G16 And R ^G17 is preferably an alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group or aryloxy group, and at least one of R ^G16 and R ^G17 is alkyl. It is more preferably a group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group.

In Formula (GM-1), when a plurality of ligands represented by Formula (GM-L2) are present, the plurality of R ^{G9 to} R ^G18 may be the same or different.

Where
R ^{G19 to} R ^G28 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron. It may have a substituent. R ^G19 and ^{R G20, R G20} and ^{R G21, R G21} and ^{R G22, R G22} and ^{R G23, R G23} and ^{R G24, R G24} and ^{R G25, R G25} and ^{R G26, R G26} and ^{R G27} and, R ^G27 and R ^G28 may be bonded to each other to form a ring together with the atoms to which they are bonded.

R ^{G19 to} R ^G25 and R ^G28 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group or a cycloalkoxy group, and a hydrogen atom, an alkyl group or an aryl group Is more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

R ^G26 and R ^G27 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or a dendron, and a hydrogen atom, an alkyl group, an aryl group, It is more preferably a monovalent heterocyclic group or a dendron, further preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron, particularly preferably a hydrogen atom or a dendron, These groups may have a substituent.

It is preferable that at least one of R ^{G19 to} R ^G28 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and R ^G26 and R ^G27 More preferably, at least one is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and these groups have a substituent. Also good.

When the ligand represented by the formula (GM-L3) has a dendron, at least one of R ^G26 and R ^G27 is preferably a dendron, and R ^G26 is more preferably a dendron.

When the ligand represented by the formula (GM-L3) has an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or an aryloxy group, R ^G26 and R ^G27 Is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group, and these groups optionally have a substituent. .

In the formula (GM-1), when a plurality of ligands represented by the formula (GM-L3) are present, the plurality of R ^{G19 to} R ^G28 may be the same or different.

Where
R ^{G29 to} R ^G38 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and these groups are It may have a substituent. R ^G29 and ^{R G30, R G30} and ^{R G31, R G31} and ^{R G32, R G32} and ^{R G33, R G33} and ^{R G34, R G34} and ^{R G35, R G35} and ^{R G36, R G36} and ^{R G37} and, R ^G37 and R ^G38 may be bonded to each other to form a ring together with the atoms to which they are bonded.

R ^{G29 to} R ^G32 , R ^G34 , R ^G35 and R ^G38 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group or a cycloalkoxy group, and a hydrogen atom More preferably, it is an alkyl group or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

R ^G33 , R ^G36 and R ^G37 are each preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or a dendron, and a hydrogen atom, an alkyl group, It is more preferably an aryl group, a monovalent heterocyclic group or a dendron, more preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron, and a hydrogen atom or a dendron. Particularly preferred, these groups may have a substituent.

It is preferable that at least one of R ^{G29 to} R ^G38 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and R ^G33 , R ^G36 and More preferably, at least one of R ^G37 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a dendron, and these groups have a substituent. You may do it.

When the ligand represented by the formula (GM-L4) has a dendron, at least one of R ^G36 and R ^G37 is preferably a dendron, and R ^G36 is more preferably a dendron.

When the ligand represented by the formula (GM-L4) has an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or an aryloxy group, R ^G33 , R ^G36 And R ^G37 is preferably an alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group or aryloxy group, and at least one of R ^G36 and R ^G37 is alkyl. More preferably a group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group, and R ^G36 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent complex More preferably, it is a cyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group.

In Formula (GM-1), when a plurality of ligands represented by Formula (GM-L4) are present, the plurality of R ^{G29 to} R ^G38 may be the same as or different from each other.

When ring R ^1G1 has no bond, the definition of ring R ^{1G1 is} the same as the definition of ring R ^1G described above.

When ring R ^1G1 has a bond, the definition of the ring portion excluding the bond of ring R ^1G1 is the same as the definition of ring R ^1G described above.

When ring R ^2G1 does not have a bond, the definition of ring R ^{2G1 is} the same as the definition of ring R ^2G described above.

When the ring R ^2G1 has a bond, the definition of the ring portion excluding the bond of the ring R ^2G1 is the same as the definition of the ring R ^2G described above.

In formula (GM-1), the ligand represented by ring R ^{1G1 -ring} R ^2G1 is preferably a ligand represented by formula (GM-L1) to formula (GM-L4), A ligand represented by the formula (GM-L1) or (GM-L2) is more preferable.

When the ligand represented by the ring R ^{1G1 -ring} R ^2G1 is the formula (GM-L1), one of R ^{G1 to} R ^G8 represents a bond, and R ^G2 , R ^G3 , R ^G6 or R ^G7 is preferably a bond, R ^G2 , R ^G6 or R ^G7 is more preferably a bond, R ^G2 or R ^G6 is more preferably a bond, and R ^G6 is a bond. It is particularly preferred.

When the ligand represented by ring R ^{1G1 -ring} R ^2G1 is the formula (GM-L2), one of R ^{G9 to} R ^G18 represents a bond, and R ^G10 , R ^G16, or R ^G17 is bonded. A hand is preferable, and R ^G16 is more preferably a bond.

When the ligand represented by the ring R ^{1G1 -ring} R ^2G1 is the formula (GM-L3), one of R ^{G19 to} R ^B28 represents a bond, and R ^G26 or R ^G27 is a bond. It is preferable that R ^G26 is a bond.

When the ligand represented by ring R ^{1G1 -ring} R ^2G1 is the formula (GM-L4), one of R ^{G29 to} R ^B38 represents a bond, and R ^G36 or R ^G37 is a bond. It is preferable that ^RG36 is a bond.

Examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² include the same examples and preferred embodiments of the phosphorescent compound represented by the formula (1-A).

Where
M ^1G represents the same meaning as M ^1G in formula (1G).
L ² and L ³ are each independently an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, or —C (R ^B ). A group represented by ═C (R ^B ) —, a group represented by —C≡C—, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A and R ^B represent the same meaning as described above. When a plurality of L ² and L ³ are present, they may be the same or different.
n ^b1 and n ^c1 each independently represent an integer of 0 or more. A plurality of n ^b1 may be the same or different.
Ar ^1M represents a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group, and these groups optionally have a substituent.

L ² is preferably a group represented by —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, more preferably an arylene group or a divalent heterocyclic group. More preferably, they are groups, and these groups may have a substituent. Among these, a group represented by the formula (A-1) or (A-2) is preferable.

L ³ is preferably a group represented by —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, and is a group represented by —C (R ^B ) ₂ — or an arylene group. More preferably, it is more preferably an arylene group, and these groups may have a substituent.
Among these, a group represented by the formula (A-1) or (A-2) is preferable.

n ^b1 and n ^c1 are usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably 0. It is.

Ar ^1M is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a triazine ring, a carbazole ring, a phenoxazine ring, or a phenothiazine ring. The group is preferably a group in which three hydrogen atoms directly bonded are removed, and three hydrogen atoms directly bonded to carbon atoms constituting the ring are excluded from a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring or dihydrophenanthrene ring. More preferably a group obtained by removing three hydrogen atoms directly bonded to the carbon atoms constituting the ring from the benzene ring or fluorene ring, and the carbon constituting the ring from the benzene ring. Particularly a group excluding three hydrogen atoms directly bonded to the atom Preferably, these groups may have a substituent.

The substituent that L ² , L ^3, and Ar ^1M may have is the same as the substituent that the above-described ring R ^1G and ring R ^2G may have.

Where
L ² and n ^b1 represent the same meaning as L ² and n ^b1 in formula (2G), respectively.
M ^2G represents a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound.

M ^2G is preferably a group represented by the formula (GM-2) or (GM-3), and more preferably a group represented by the formula (GM-2).

Where
M, ^{E 4,} ring ^{R 1G,} ring ^{R 2G, A 1 -G 1 -A} 2, ring ^{R 1G1,} ring ^{R 2G1, n 11,} and ^{n 12} is, M in each formula (GM-1), ^{E 4} represents the ring ^{R 1G,} ring ^{R 2G, a 1 -G 1 -A} 2, ring ^{R 1G1,} the same meaning as ring ^{R 2G1, n 11} and ^{n 12.}
n ¹³ and ^{n 14} each independently represents an integer of 0-1. However, n ¹³ + n ¹⁴ is 0 or 1. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹³ + n ¹⁴ is 1, and when M is a palladium atom or a platinum atom, n ¹³ + n ¹⁴ is 0.
Ring R ^1G2 represents a 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
Ring R ^2G2 represents a 5-membered or 6-membered aromatic carbocyclic ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and these rings optionally have a substituent. When a plurality of the substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
However, one of the ring R ^1G2 and the ring R ^2G2 has two bonds, or the ring R ^1G2 and the ring R ^2G2 each have one bond.

When M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹⁴ is preferably 0.

When ring R ^1G2 has no bond, the definition of ring R ^{1G2 is} the same as the definition of ring R ^1G described above.

When the ring R ^1G2 has a bond, the definition of the ring portion excluding the bond of the ring R ^1G2 is the same as the definition of the ring R ^1G described above.

When ring R ^2G2 does not have a bond, the definition of ring R ^{2G2 is} the same as the definition of ring R ^2G described above.

When ring R ^2G2 has a bond, the definition of the ring portion excluding the bond of ring R ^2G2 is the same as the definition of ring R ^2G described above.

The substituent that the ring R ^1G2 and the ring R ^2G2 may have is the same as the substituent that the ring R ^1G and the ring R ^2G may have.

^{Each of the} ring R ^1G2 and the ring R ^2G2 preferably has one bond.

The ligand represented by ring R ^{1G2 -ring} R ^2G2 is preferably a ligand represented by formulas (GM-L1) to (GM-L4), and is represented by formula (GM-L1) or (GM -L2) is more preferred.

When the ligand represented by ring R ^{1G2 -ring} R ^2G2 is the formula (GM-L1), two of R ^{G1 to} R ^G8 represent a bond, and R ^G2 , R ^G3 , R ^G6, and R Of ^G7 , two are preferably bonds, and R ^G2 and R ^G6 , R ^G2 and R ^G7 , R ^G3 and R ^G6 , or R ^G3 and R ^G7 are more preferably bonds.

When the ligand represented by ring R ^{1G2 -ring} R ^2G2 is the formula (GM-L2), two of R ^{G9 to} R ^G18 represent a bond, and among R ^G10 , R ^G16 and R ^G17 Two are preferably bonds, and R ^G10 and R ^G16 , or R ^G10 and R ^G17 are more preferably bonds.

When the ligand represented by ring R ^{1G2 -ring} R ^2G2 is the formula (GM-L3), two of R ^{G19 to} R ^G28 represent a bond, and R ^{G20 to} R ^G23 , R ^G26, and R Two of ^G27 are preferably bonds, and R ^G26 and one selected from the group consisting of R ^G20 , R ^G21 , R ^G22 and R ^G23 are bonds, or R ^G27 , and More preferably, one selected from the group consisting of R ^G20 , R ^G21 , R ^G22 and R ^G23 is a bond.

When the ligand represented by ring R ^{1G2 -ring} R ^2G2 is the formula (GM-L4), two of R ^{G29 to} R ^G38 represent a bond, and among R ^G36 , R ^G37 and R ^G33 Two are preferably bonds, and R ^G36 and R ^G33 , or R ^G37 and R ^G33 are more preferably bonds.

In formula (3G), the preferred range of ^{L 2,} and ^{n b1,} which is the same as ^{L 2,} and ^{n b1} in formula (2G). Examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² are the same as those exemplified and preferred in the phosphorescent compound represented by the formula (1-A). It is done.

Where
L ² and n ^b1 represent the same meaning as L ² and n ^b1 in formula (2G), respectively.
M ^3G represents a group obtained by removing three hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the compound from the phosphorescent compound.

M ^3G is preferably a group represented by the formula (GM-4).

Where
M, ^{E 4,} ring ^{R 1G1,} ring ^{R 2G1,} ring ^{R 1G2} and ring ^{R 2G2} is, M in each formula ^{(GM-2), E 4} , ring ^{R 1G1,} ring ^{R 2G1,} ring ^{R 1G2} and ring ^{R 2G2} Means the same.
n ¹⁵ represents 0 or 1. n ¹⁶ represents 1 or 3. However, when M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹⁵ is 0 and n ¹⁶ is 3.
When M is a palladium atom or a platinum atom, n ¹⁵ is 1 and n ¹⁶ is 1.

In formula (4G), the preferred range of ^{L 2,} and ^{n b1,} which is the same as ^{L 2,} and ^{n b1} in formula (2G).

Examples of the structural unit represented by the formula (1G) include formulas (1G-1), (1G-2), (1G-3), (1G-4), (1G-5), and (1G-6). ), (1G-7), (1G-8), (1G-9), (1G-10), (1G-11), or (1G-12) (1) It is referred to as “the structural unit represented by (1G-1) to (1G-12)”.
).

  In the formula, De is represented by a hydrogen atom, a methyl group, an ethyl group, a propyl group, an n-butyl group, a tert-butyl group, a group represented by the formula (DA), or a formula (DB). Represents a group.

  Examples of the structural unit represented by the formula (2G) include formulas (2G-1), (2G-2), (2G-3), (2G-4), (2G-5), and (2G-6). ), (2G-7), (2G-8), (2G-9), (2G-10), (2G-11) or (2G-12) (The structural unit represented by (2G-1) to (2G-12) ”).

  In the formula, De is represented by a hydrogen atom, a methyl group, an ethyl group, a propyl group, an n-butyl group, a tert-butyl group, a group represented by the formula (DA), or a formula (DB). Represents a group.

  Examples of the structural unit represented by the formula (3G) include formulas (3G-1), (3G-2), (3G-3), (3G-4), (3G-5), and (3G-6). ), (3G-7), (3G-8), (3G-9), (3G-10), (3G-11), (3G-12), (3G-13), (3G-14), A structural unit represented by (3G-15), (3G-16), (3G-17), (3G-18), (3G-19) or (3G-20) (hereinafter, “formula (3G -1) to (3G-20) ”.

  In the formula, De is represented by a hydrogen atom, a methyl group, an ethyl group, a propyl group, an n-butyl group, a tert-butyl group, a group represented by the formula (DA), or a formula (DB). Represents a group.

  As the structural unit represented by formula (4G), formula (4G-1), (4G-2), (4G-3), (4G-4), (4G-5), (4G-6) or And a structural unit represented by (4G-7) (hereinafter referred to as “structural units represented by formulas (4G-1) to (4G-7)” in some cases).

  In the formula, De is represented by a hydrogen atom, a methyl group, an ethyl group, a propyl group, an n-butyl group, a tert-butyl group, a group represented by the formula (DA), or a formula (DB). Represents a group.

  In the phosphorescent polymer compound, the phosphorescent constituent unit is preferably bonded to a benzene ring having no substituent at the ortho position. According to such a phosphorescent polymer compound, a light emitting device with further improved power efficiency can be obtained.

  Since the phosphorescent polymer compound provides a light emitting device with further improved power efficiency, the monomer or terminal blocker that forms the phosphorescent constituent unit with respect to the total amount of monomers that form the phosphorescent polymer compound In an amount of 0.01 mol% to 30 mol% (more preferably 0.05 mol% to 20 mol%, and still more preferably 0.1 mol% to 10 mol%). Is preferred.

  As the phosphorescent polymer compound (which may be a crosslinkable phosphorescent polymer compound), a polymer compound that emits phosphorescence in the visible region (400 to 700 nm) is preferable because the power efficiency of the light emitting device is further improved. . The emission peak wavelength of the phosphorescent polymer compound is more preferably 490 to 700 nm, still more preferably 550 to 700 nm, and particularly preferably 570 to 700 nm.

  The phosphorescent polymer compound (which may be a crosslinkable phosphorescent polymer compound) preferably exhibits a desired emission color in the light emitting element. The emission peak wavelength of the phosphorescent polymer compound is determined, for example, by measuring the emission peak wavelength when a voltage is applied to a light-emitting element for evaluation in which the phosphorescent polymer compound is formed between a cathode and an anode. Can be confirmed. The cathode and anode materials used for the evaluation element, the film thickness of the phosphorescent polymer compound, and the voltage to be applied may be appropriately determined according to the light-emitting element intended for the product. In the evaluation element, the phosphorescent polymer compound may be cross-linked or not cross-linked, but is cross-linked under a cross-linking reaction condition that is applied when a light-emitting element intended as a product is manufactured. It is preferable.

  The phosphorescent polymer compound has an emission peak on the long wavelength side of 1 to 200 nm with respect to the phosphorescent compound having an emission peak on the longest wavelength side among the phosphorescent compounds used for forming the first organic layer. It preferably has a wavelength, more preferably has an emission peak wavelength on the long wavelength side of 10 to 180 nm, and further preferably has an emission peak wavelength on the long wavelength side of 50 to 160 nm.

  The phosphorescent polymer compound may contain only one type of phosphorescent constituent unit or may contain two or more types.

  The phosphorescent polymer compound may further contain a structural unit represented by the formula (X). The phosphorescent polymer compound may further include a structural unit represented by the formula (Y) and / or a structural unit represented by the formula (Y12).

  Examples, preferred embodiments and contents of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y12) in the phosphorescent polymer compound are as follows. The same.

  The phosphorescent polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other embodiments, but a plurality of types of raw materials A copolymer obtained by copolymerizing monomers is preferred.

  In one embodiment, the phosphorescent polymer compound may contain at least a first block having a phosphorescent constituent unit and a second block having no phosphorescent constituent unit. For example, the first block may be a block in which a phosphorescent structural unit and one or more of other structural units are copolymerized. Further, the second block may be a block in which other structural units other than the phosphorescent structural unit are polymerized, and may be a block in which two or more of the other structural units are copolymerized. In this aspect, by dividing the positions of the structural units into the first block and the second block, structural units that are not preferably adjacent to each other can be contained in the same polymer compound.

  The second block may have, for example, a structural unit in which a bond from a benzene ring having a substituent at the ortho position to another structural unit extends. When the phosphorescent polymer compound is a block copolymer having such a structural unit, such a structural unit is preferably contained in a block different from the phosphorescent structural unit.

[Crosslinkable phosphorescent polymer compound]
The crosslinkable polymer compound may further include the phosphorescent structural unit, and the phosphorescent polymer compound may further include a crosslinked structural unit having the crosslinkable group. That is, the polymer compound may be a polymer compound having a phosphorescent structural unit and a crosslinking group.

  Examples, preferred embodiments, and contents of the phosphorescent constituent unit in the crosslinkable phosphorescent polymer compound include the same phosphorescent constituent units in the phosphorescent polymer compound. Moreover, as an illustration, a preferable aspect, and content of the crosslinking group and crosslinked structural unit in a crosslinkable phosphorescent polymer compound, the same thing as the crosslinking group and crosslinked structural unit in the said crosslinkable polymer compound is mentioned. Further, examples of suitable properties of the crosslinkable phosphorescent polymer compound include the same properties as those of the crosslinkable polymer compound and the phosphorescent polymer compound.

  Examples of the crosslinkable phosphorescent polymer compound include the polymer compounds (P-11), (P-12), (P-13), (P-14), (P-15), ( P-16), (P-17), (P-18), (P-19), (P-20), (P-21), (P-22) and (P-23).

  In Table 2, p ′, q ′, r ′, s ′, t ′, u ′, and v ′ represent the molar ratio of each structural unit. p ′ + q ′ + r ′ + s ′ + t ′ + u ′ + v ′ = 100, 70 ≦ p ′ + q ′ + r ′ + s ′ + t ′ ≦ 100, and 0 ≦ q ′ + s ′ ≦ 50. “Others” means a structural unit represented by the formula (2), a structural unit represented by the formula (3), a structural unit represented by the formulas (1G) to (4G), and the formula (X-1) to It means a structural unit other than the structural unit represented by (X-7) or the structural unit represented by formula (Y12).

  The crosslinkable phosphorescent polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A copolymer obtained by copolymerizing the raw material monomers is preferable.

  In one embodiment, the crosslinkable phosphorescent polymer compound may contain at least a first block having a phosphorescent constituent unit and a second block having no phosphorescent constituent unit. For example, the first block may be a block in which a phosphorescent structural unit and one or more of other structural units are copolymerized. Further, the second block may be a block in which other structural units other than the phosphorescent structural unit are polymerized, and may be a block in which two or more of the other structural units are copolymerized. In this aspect, by dividing the positions of the structural units into the first block and the second block, structural units that are not preferably adjacent to each other can be contained in the same polymer compound. In this embodiment, the cross-linking structural unit having a crosslinkable group may be contained in the first block, may be contained in the second block, and is contained in both the first block and the second block. It may be.

  The second block may have, for example, a structural unit in which a bond from a benzene ring having a substituent at the ortho position to another structural unit extends. When the crosslinkable phosphorescent polymer compound is a block copolymer having such a structural unit, such a structural unit is preferably contained in a block different from the phosphorescent structural unit.

[Method for producing polymer compound]
The polymer compound used for forming the second organic layer can be produced by a method similar to the method for producing the polymer host described above.

[Average number of cross-linking groups]
The second organic layer is formed using a polymer composition in which one or more polymer compounds including a crosslinkable polymer compound having a crosslinking group are blended. In the present embodiment, an index indicating the average number of crosslinking groups in the polymer compound used for forming the second organic layer can be obtained by the following method.

First, for each monomer unit constituting the polymer compound, a value x obtained by multiplying the molar ratio C of the monomer unit to the total mole of all monomer units and the molecular weight M of the monomer unit, and Then, a value y obtained by multiplying the molar ratio C by the number n of crosslinking groups of the monomer unit is obtained. Next, the total sum of x determined for each monomer unit is X ₁ , and the total sum of y determined for each monomer unit is Y ₁ .

At this time, the value of (Y ₁ × 1000) / X ₁ is substantially equal to the average number of crosslinking groups per 1000 molecular weight of the polymer compound, and is effective as an index indicating the average number of crosslinking groups in the polymer compound. Can be used. Hereinafter, the value of (Y ₁ × 1000) / X ₁ is sometimes referred to as “average number of cross-linking groups per 1000 molecular weight”.

  A specific method for calculating the average number of cross-linking groups will be described in detail for the polymer compound P1 used in Example 1 below.

  The polymer compound P1 has monomer units formed from the compounds MM1, MM2, MM3, and MM4, which are monomers. The ratio of all monomers to the total mole is 0.40 for compound MM1, 0.10 for compound MM2, 0.47 for compound MM3, and 0.03 for compound MM4. The molecular weight of the monomer unit formed from the compound MM1 is 776.45, the molecular weight of the monomer unit formed from the compound MM2 is 240.20, and the molecular weight of the monomer unit formed from the compound MM3 is 750. .51, the molecular weight of the monomer unit formed from compound MM4 is 1682.77. In addition, the number of crosslinking groups included in the compound MM1 is 2, the number of crosslinking groups included in the compound MM2 is 2, the number of crosslinking groups included in the compound MM3 is 0, and the number of crosslinking groups included in the compound MM4 is 0.

Thus, _{X 1} is determined as follows.
(0.40 × 776.45) + (0.10 × 240.20) + (0.47 × 750.51) + (0.03 × 168.77) = 737.82

Moreover, _{Y 1} is determined as follows.
(0.40 × 2) + (0.10 × 2) + (0.47 × 0) + (0.03 × 0) = 1.00

Therefore, the average number of cross-linking groups per 1000 molecular weight is determined as follows.
(1.00 × 1000) /737.82=1.36

When the polymer composition contains two or more polymer compounds as the polymer compound, the value of (Y ₁ × 1000) / X ₁ is obtained based on the monomer unit constituting each polymer compound. . Moreover, the value of (Y ₁ × 1000) / X ₁ is obtained for each polymer compound, and the value of (Y ₁ × 1000) / X ₁ of the entire polymer compound is obtained from the blending ratio of each polymer compound. Can do.

  A specific calculation method will be described for the case where the polymer compound P1 and the polymer compound P2 of Example 2 below are blended at a ratio of 90:10.

  The average number of crosslinking groups per 1000 molecular weight in the polymer compound P1 is 1.36.

  The polymer compound P2 has monomer units formed from the compounds MM1, MM2, MM5, MM3, and MM4, which are monomers. The ratio of all monomers to the total mole is 0.05 for compound MM1, 0.05 for compound MM2, 0.40 for compound MM5, 0.47 for compound MM3, and 0.03 for compound MM4. The molecular weight of the monomer unit formed from the compound MM1 is 776.45, the molecular weight of the monomer unit formed from the compound MM2 is 240.20, and the molecular weight of the monomer unit formed from the compound MM5 is 244. .23, the molecular weight of the monomer unit formed from the compound MM3 is 750.51, and the molecular weight of the monomer unit formed from the compound MM4 is 1682.77. In addition, the number of crosslinking groups that the compound MM1 has is 2, the number of crosslinking groups that the compound MM2 has 2, the number of crosslinking groups that the compound MM5 has 0, the number of crosslinking groups that the compound MM3 has 0, and the compound MM4 has The number of cross-linking groups is zero.

Thus, _{X 1} is determined as follows.
(0.05 × 776.45) + (0.05 × 240.20) + (0.40 × 244.23) + (0.47 × 750.51) + (0.03 × 168.77) = 551.75

Moreover, _{Y 1} is determined as follows.
(0.05 × 2) + (0.05 × 2) + (0.40 × 0) + (0.47 × 0) + (0.03 × 0) = 0.20

Therefore, the average number of cross-linking groups per 1000 molecular weight is determined as follows.
(0.20 × 1000) /5511.75=0.36

The value of (Y ₁ × 1000) / X ₁ of the entire polymer compound when polymer compound P1 and polymer compound P2 are blended at a ratio of 90:10 is obtained as follows.
(1.36 × 0.9) + (0.36 × 0.1) = 1.26

  In this embodiment, the average number of cross-linking groups per 1000 molecular weight is preferably 0.7 or more, more preferably 0.8 or more, still more preferably 1.0 or more, and 1.1 or more. More preferably, it is more preferably 1.2 or more. By increasing the average number of cross-linking groups, a dense film is formed by the cross-linkable polymer compound, and the charge transport property of the second organic layer and / or charge injection from the second organic layer to the first organic layer. Will be improved.

  In the present embodiment, the average number of crosslinking groups per 1000 molecular weight may be 10 or less, for example, or 3 or less. By setting the average number of cross-linking groups within this range, an effect that the luminance life of the light emitting device according to the present embodiment is excellent is achieved.

[Composition of second organic layer]
The second organic layer is at least one material selected from the group consisting of the polymer compound, 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. May be a layer formed using a composition containing the following (hereinafter also referred to as “composition of the second organic layer”).

  For example, the second organic layer may be a layer containing a cured product obtained by curing the composition of the second organic layer. The composition of the second organic layer can be cured, for example, by crosslinking a crosslinking group in the polymer compound.

  Examples and preferred ranges of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material contained in the composition of the second organic layer are contained in the composition of the first organic layer. Examples of the hole transporting material, electron transporting material, hole injecting material, electron injecting material, and light emitting material are the same as the examples and preferred ranges.

  In the composition of the second organic layer, the amount of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material is usually set to 100 parts by mass of the polymer compound. 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

  Examples and preferred ranges of the antioxidant contained in the composition of the second organic layer are the same as examples and preferred ranges of the antioxidant contained in the composition of the first organic layer.

  In the composition of the second organic layer, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the crosslinkable polymer compound is 100 parts by mass.

[Ink for second organic layer]
The composition of the second organic layer containing a solvent (hereinafter, also referred to as “second organic layer ink”).
) Can be suitably used for coating methods such as spin coating and ink jet printing, as with the ink for the first organic layer.

  The preferable range of the viscosity of the ink for the second organic layer is the same as the preferable range of the viscosity of the ink for the first organic layer.

  The solvent contained in the ink for the second organic layer is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples and preferred ranges of the solvent are the same as examples and preferred ranges of the solvent contained in the first organic layer ink.

  In the ink for the second organic layer, the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass when the polymer compound is 100 parts by mass.

<Layer structure of light emitting element>
The light emitting device according to this embodiment includes an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the first organic layer. Have The light emitting device according to this embodiment may have a layer other than the anode, the cathode, the first organic layer, and the second organic layer.

  In the light emitting device according to this embodiment, the first organic layer is usually a light emitting layer.

  In the light emitting device according to this embodiment, the first organic layer and the second organic layer are preferably adjacent to each other because the power efficiency of the light emitting device according to this embodiment is further improved.

  The light emitting device according to this embodiment is selected from the group consisting of a hole transport layer and a hole injection layer between the anode and the second organic layer because the power efficiency of the light emitting device according to this embodiment is more excellent. It is preferable to further have at least one layer. The light emitting device according to this embodiment is selected from the group consisting of an electron transport layer and an electron injection layer between the cathode and the first organic layer because the power efficiency of the light emitting device according to this embodiment is excellent. It is preferable to further have at least one layer.

  As a specific layer structure of the light emitting element according to the present embodiment, for example, the following (D1), (D2), (D3), (D4), (D5), (D6), (D7), (D8) ), (D9), (D10), (D11), (D12), (D13), (D14), (D15) or (D16) (hereinafter referred to as “(D1) to (D D16) ”). The light emitting device according to this embodiment usually has a substrate, but may be laminated from the anode on the substrate, or may be laminated from the cathode on the substrate.

(D1) Anode / second organic layer / first organic layer / cathode (D2) anode / second organic layer / first organic layer / electron transport layer / cathode (D3) anode / second organic layer / First organic layer / electron injection layer / cathode (D4) anode / second organic layer / first organic layer / electron transport layer / electron injection layer / cathode (D5) anode / hole injection layer / second Organic layer / first organic layer / cathode (D6) anode / hole injection layer / second organic layer / first organic layer / electron transport layer / cathode (D7) anode / hole injection layer / second Organic layer / first organic layer / electron injection layer / cathode (D8) anode / hole injection layer / second organic layer / first organic layer / electron transport layer / electron injection layer / cathode (D9) anode / Hole transport layer / second organic layer / first organic layer / cathode (D10) anode / hole transport layer / second organic layer / first organic layer / electron transport layer / cathode (D11) anode / Hole transport / Second organic layer / first organic layer / electron injection layer / cathode (D12) anode / hole transport layer / second organic layer / first organic layer / electron transport layer / electron injection layer / cathode ( D13) Anode / hole injection layer / hole transport layer / second organic layer / first organic layer / cathode (D14) anode / hole injection layer / hole transport layer / second organic layer / first Organic layer / electron transport layer / cathode (D15) anode / hole injection layer / hole transport layer / second organic layer / first organic layer / electron injection layer / cathode (D16) anode / hole injection layer / Hole transport layer / second organic layer / first organic layer / electron transport layer / electron injection layer / cathode

  In the above (D1) to (D16), “/” means that the layers before and after that are adjacently stacked. Specifically, “second organic layer / first organic layer” means that the second organic layer and the first organic layer are stacked adjacent to each other.

  In the light emitting device according to the present embodiment, two or more hole injection layers, hole transport layers, electron transport layers, and electron injection layers may be provided as necessary.

  The thickness of the anode, cathode, first organic layer, second organic layer, hole injection layer, hole transport layer, electron injection layer and electron transport layer is usually 1 nm to 1 μm, preferably 2 nm to It is 500 nm, More preferably, it is 5 nm-150 nm.

  In the light emitting element according to this embodiment, the order, the number, and the thickness of the stacked layers may be adjusted in consideration of the power efficiency and the element life of the light emitting element.

[Hole transport layer]
The hole transport layer is usually a layer formed using a hole transport material. As a hole transport material used for formation of a hole transport layer, the hole transport material which the composition of the above-mentioned 1st organic layer may contain is mentioned, for example. A hole transport material may be used individually by 1 type, or may use 2 or more types together.

[Electron transport layer]
The electron transport layer is usually a layer formed using an electron transport material. As an electron transport material used for forming an electron transport layer, for example, an electron transport material that may be contained in the composition of the first organic layer described above, a structural unit represented by the formula (ET-1), and a formula A polymer compound containing at least one structural unit selected from the group consisting of structural units represented by (ET-2), and a structural unit represented by formula (ET-1) and a formula (ET-2) The polymer compound containing at least one structural unit selected from the group consisting of structural units represented by An electron transport material may be used individually by 1 type, or may use 2 or more types together.

Where
nE1 represents an integer of 1 or more.
Ar ^E1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R ^E1 .
R ^E1 represents a group represented by the formula (ES-1). When a plurality of R ^E1 are present, they may be the same or different.

-(R ^E3 ) _cE1- (Q ^E1 ) _nE4 -Y ^E1 (M ^E2 ) _aE1 (Z ^E1 ) _bE1 (ES-1)
[Where:
cE1 represents 0 or 1, nE4 represents an integer of 0 or more, aE1 represents an integer of 1 or more, and bE1 represents an integer of 0 or more.
R ^E3 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Q ^E1 represents an alkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of Q ^E1 are present, they may be the same or different.
Y ^E1 represents —CO ₂ ^— , —SO ₃ ^— , —SO ₂ ^— or —PO ₃ ^2— .
M ^E2 represents a metal cation or an ammonium cation, and this ammonium cation may have a substituent. When a plurality of M ^E2 are present, they may be the same or different.
Z ^E1 represents F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , OH ⁻ , R ^E4 SO ₃ ⁻ , R ^E4 COO ⁻ , ClO ⁻ , ClO ₂ ⁻ , ClO ₃ ⁻ , ClO ₄ ⁻ , SCN ⁻ , CN ^−. , NO ₃ ⁻ , SO ₄ ²⁻ , HSO ₄ ⁻ , PO ₄ ³⁻ , HPO ₄ ²⁻ , H ₂ PO ₄ ⁻ , BF ₄ ⁻ or PF ₆ ⁻ . R ^E4 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups optionally have a substituent. When a plurality of Z ^E1 are present, they may be the same or different.
aE1 and bE1 are selected such that the charge of the group represented by the formula (ES-1) is zero. ]

  nE1 is preferably an integer of 1 to 4, more preferably 1 or 2.

Examples of the aromatic hydrocarbon group or heterocyclic group represented by Ar ^E1 include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 2,6-naphthalenediyl group, 1,4 Hydrogen bonded directly to the atoms constituting the ring from a naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthenediyl group or a 2,7-carbazolediyl group The remaining atomic group excluding one atom nE1 is preferable, and may have a substituent other than R ^E1 .

Examples of the substituent other than R ^E1 that Ar ^E1 may have include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, and an aryloxy group. Group, an amino group, a substituted amino group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, a carboxyl group, and a group represented by the formula (ES-3).

—O (C _{n ′} H _{2n ′} O) _nx C _{m ′} H _{2m ′ + 1} (ES-3)
[Wherein, n ′, m ′ and nx represent an integer of 1 or more. ]

  cE1 is preferably 0 or 1, and nE4 is preferably an integer of 0 to 6.

R ^E3 is preferably an arylene group.

^Examples of the substituent that R ^E3 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3). R ^E3 preferably has a group represented by the formula (ES-3) as a substituent because the power efficiency of the light emitting device according to this embodiment is more excellent.

Q ^E1 is preferably an alkylene group, an arylene group or an oxygen atom.

Y ^E1 is preferably —CO ₂ ^— or —SO ₃ ^— .

M ^E2 includes Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , N (CH ₃ ) ₄ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ or N (C ₂ H ₅ ) ₄ ⁺ Is preferred.

Z ^E1 is preferably F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , OH ⁻ , R ^E4 SO ₃ ^— or R ^E4 COO ⁻ .

  Examples of the group represented by the formula (ES-1) include a group represented by the following formula.

In the formula, M ⁺ represents Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , N (CH ₃ ) ₄ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ or N (C ₂ H _{5 4} represents ⁺ .

Where
nE2 represents an integer of 1 or more.
Ar ^E2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R ^E2 .
R ^E2 represents a group represented by the formula (ES-2). When a plurality of R ^E2 are present, they may be the same or different.

^{_{- (R E6) cE2 - (}} Q E2) nE6 -Y E2 (M E3) bE2 (Z E2) aE2 (ES-2)
[Where:
cE2 represents 0 or 1, nE6 represents an integer of 0 or more, bE2 represents an integer of 1 or more, and aE2 represents an integer of 0 or more.
R ^E6 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Q ^E2 represents an alkylene group, an arylene group, an oxygen atom or a sulfur atom, and these groups optionally have a substituent. When a plurality of Q ^E2 are present, they may be the same or different.
Y ^E2 represents a carbocation, an ammonium cation, a phosphonyl cation or a sulfonyl cation.
M ^E3 is F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , OH ⁻ , R ^E7 SO ₃ ⁻ , R ^E7 COO ⁻ , ClO ⁻ , ClO ₂ ⁻ , ClO ₃ ⁻ , ClO ₄ ⁻ , SCN ⁻ , CN ^−. , NO ₃ ⁻ , SO ₄ ²⁻ , HSO ₄ ⁻ , PO ₄ ³⁻ , HPO ₄ ²⁻ , H ₂ PO ₄ ⁻ , tetraphenylborate, BF ₄ ⁻ or PF ₆ ⁻ . R ^E7 represents an alkyl group, a perfluoroalkyl group, or an aryl group, and these groups optionally have a substituent. When a plurality of M ^E3 are present, they may be the same or different.
Z ^E2 represents a metal ion or an ammonium ion, and this ammonium ion may have a substituent. When a plurality of Z ^E2 are present, they may be the same or different.
aE2 and bE2 are selected so that the charge of the group represented by the formula (ES-2) becomes zero. ]

  nE2 is preferably an integer of 1 to 4, more preferably 1 or 2.

Examples of the aromatic hydrocarbon group or heterocyclic group represented by Ar ^E2 include 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 2,6-naphthalenediyl group, 1,4 Hydrogen bonded directly to the atoms constituting the ring from a naphthalenediyl group, a 2,7-fluorenediyl group, a 3,6-fluorenediyl group, a 2,7-phenanthenediyl group or a 2,7-carbazolediyl group The remaining atomic group excluding 2 atoms nE is preferable, and may have a substituent other than R ^E2 .

The substituent group other than Ar ^E2 is may have ^{R E2,} is the same as the substituent other than optionally ^{Ar E1} is have ^{R E1.}

  cE2 is preferably 0 or 1, and nE6 is preferably an integer of 0 to 6.

R ^E6 is preferably an arylene group.

^Examples of the substituent that R ^E6 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3). R ^E6 preferably has a group represented by the formula (ES-3) as a substituent because the power efficiency of the light emitting device according to this embodiment is more excellent.

Q ^E2 is preferably an alkylene group, an arylene group or an oxygen atom.

Y ^E2 is preferably a carbocation or an ammonium cation.

As M ^E3 , F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , tetraphenylborate, CF ₃ SO ₃ ^— or CH ₃ COO ⁻ is preferable.

As Z ^E2 , Li ⁺ , Na ⁺ , K ⁺ , Cs ⁺ , N (CH ₃ ) ₄ ⁺ , NH (CH ₃ ) ₃ ⁺ , NH ₂ (CH ₃ ) ₂ ⁺ or N (C ₂ H ₅ ) ₄ ⁺ Is preferred.

  Examples of the group represented by the formula (ES-2) include a group represented by the following formula.

Wherein, X ^{- is, F -, Cl -, Br} -, I -, tetraphenylborate, _{CF 3} SO 3 ^-, or _CH 3 COO ^- represents a.

  Examples of the structural unit represented by the formula (ET-1) or (ET-2) include those represented by the following formula (ET-31), (ET-32), (ET-33), or (ET-34). Structural units.

  For forming a hole injection layer, a material used for forming a hole transport layer, a material used for forming a second organic layer, a material used for forming a first organic layer, and a material for forming an electron transport layer. The materials used and the materials used to form the electron injection layer, which will be described later, are a hole injection layer, a hole transport layer, a second organic layer, a first organic layer, an electron transport layer, and an electron, respectively, in the manufacture of the light-emitting element. When dissolved in the solvent used when forming the layer adjacent to the injection layer, it is preferred to avoid dissolution of the material in the solvent. As a method for avoiding dissolution of the material, i) a method using a material having a crosslinking group, or ii) a method of providing a difference in solubility between adjacent layers is preferable. In the method i), after forming a layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

  For example, when an electron transport layer is stacked on the first organic layer using a difference in solubility, the electron transport layer is stacked by using a solution having low solubility with respect to the first organic layer. be able to.

  Solvents used for laminating the electron transport layer on the first organic layer using the difference in solubility include water, alcohols, ethers, esters, nitrile compounds, nitro compounds, fluorine Preferred are fluorinated alcohols, thiols, sulfides, sulfoxides, thioketones, amides, carboxylic acids and the like. Specific examples of the solvent include methanol, ethanol, 2-propanol, 1-butanol, tert-butyl alcohol, acetonitrile, 1,2-ethanediol, N, N-dimethylformamide, dimethyl sulfoxide, acetic acid, nitromethane, propylene carbonate , Pyridine, carbon disulfide, and a mixed solvent of these solvents. When using a mixed solvent, it is selected from water, alcohols, ethers, esters, nitrile compounds, nitro compounds, fluorinated alcohols, thiols, sulfides, sulfoxides, thioketones, amides, carboxylic acids, etc. It may be a mixed solvent of one or more kinds of solvents and one or more kinds of solvents selected from chlorine-based solvents, aromatic hydrocarbon-based solvents, aliphatic hydrocarbon-based solvents, and ketone-based solvents.

[Hole injection layer and electron injection layer]
The hole injection layer is usually a layer formed using a hole injection material. As a hole injection material used for formation of a hole injection layer, the hole injection material which the composition of the above-mentioned 1st organic layer may contain is mentioned, for example. A hole injection material may be used individually by 1 type, or may use 2 or more types together.

  The electron injection layer is usually a layer formed using an electron injection material. As an electron injection material used for formation of an electron injection layer, the electron injection material which the composition of the above-mentioned 1st organic layer may contain is mentioned, for example. An electron injection material may be used individually by 1 type, or may use 2 or more types together.

[Substrate / Electrode]
The substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed. For example, the substrate is made of a material such as glass, plastic, or silicon. When an opaque substrate is used, it is preferable that the electrode farthest from the substrate is transparent or translucent.

  Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc. A composite of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.

  Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.

  Each of the anode and the cathode may have a laminated structure of two or more layers.

  In the light emitting device according to this embodiment, at least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.

  Examples of the method for forming the anode and the cathode include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and a laminating method.

[Method for Manufacturing Light-Emitting Element]
In the light emitting device according to the present embodiment, as a method for forming each layer such as the first organic layer, the second organic layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer, a low molecular compound In the case of using, for example, a vacuum deposition method from a powder, a method by film formation from a solution or a molten state, and when using a polymer compound, for example, a method by film formation from a solution or a molten state can be mentioned.

  The first organic layer uses the ink for the first organic layer, the second organic layer uses the ink for the second organic layer, the hole transport layer, the electron transport layer, the hole injection layer, and The electron injection layer is formed by a coating method typified by a spin coat method and an ink jet printing method using inks containing the above-described hole transport material, electron transport material, hole injection material, and electron injection material, respectively. Can do.

[Uses of light-emitting elements]
In order to obtain planar light emission using the light emitting element, the planar anode and the cathode may be arranged so as to overlap each other. In order to obtain pattern-like light emission, a method in which a mask having a pattern-like window is provided on the surface of a planar light-emitting element, a layer that is desired to be a non-light-emitting portion is formed extremely thick and substantially non-light-emitting. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern. By forming a pattern by any one of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display device capable of displaying numbers, characters, and the like can be obtained. In order to obtain a dot matrix display device, both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter. The dot matrix display device can be driven passively or can be driven actively in combination with TFTs. These display devices can be used for displays of computers, televisions, portable terminals and the like.
The planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source and display device.

  The preferred embodiment of the present invention has been described above, but the present invention is not limited to the above embodiment.

  For example, one aspect of the present invention relates to a polymer compound having the above-described crosslinking group and phosphorescent structural unit. Another aspect of the present invention may be a planar light source having the above-described light-emitting element, or a display device having the above-described light-emitting element.

  The preferred embodiment of the present invention has been described above, but the present invention is not limited to the above embodiment.

  EXAMPLES Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to an Example.

In the examples, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound are size exclusion chromatography (SEC) (trade name: LC-10Avp, manufactured by Shimadzu Corporation). Determined by The SEC measurement conditions are as follows.
[Measurement condition]
The polymer compound to be measured was dissolved in THF (tetrahydrofuran) at a concentration of 0.05% by mass, and 10 μL was injected into SEC. THF was used as the mobile phase of SEC, and flowed at a flow rate of 2.0 mL / min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.

Liquid chromatograph mass spectrometry (LC-MS) was performed by the following method.
The measurement sample was dissolved in chloroform or THF to a concentration of 2 mg / mL, and 1 μL was injected into LC-MS (manufactured by Agilent Technologies, trade name: 1100LCMSD). The LC-MS mobile phase was used while changing the ratio of acetonitrile and THF, and was allowed to flow at a flow rate of 0.2 mL / min. As the column, L-column 2 ODS (3 μm) (manufactured by Chemicals Evaluation and Research Institute, inner diameter: 2.1 mm, length: 100 mm, particle size: 3 μm) was used.

¹ H-NMR and ¹³ C-NMR were measured by the following methods.
5-10 mg of a measurement sample was dissolved in 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran (THF-d ₈ ), deuterated dimethyl sulfoxide (DMSO-d ₆ ) or methylene dichloride (CD ₂ Cl ₂ ), Measurement was performed using an NMR apparatus (manufactured by Varian, Inc., trade name: INOVA 300 or trade name: MERCURY 400VX).

  A high performance liquid chromatography (HPLC) area percentage value was used as an indicator of the purity of the compound. Unless otherwise specified, this value is a value at 254 nm by HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in THF or chloroform so as to have a concentration of 0.01 to 0.2% by weight, and 1 to 10 μL was injected into HPLC depending on the concentration. Acetonitrile and THF were used for the mobile phase of HPLC, and were flowed by a gradient analysis of acetonitrile / THF = 100/0 to 0/100 (volume ratio) at a flow rate of 1 mL / min. As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance was used. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as the detector.

(1) Phosphorescent compound <1-1> Phosphorescent compound 1
The phosphorescent compound 1 was synthesized according to the method described in International Publication No. 2006/121811.

<1-2> Phosphorescent compound 2
The following compounds were purchased from Luminescence Technology Corp as phosphorescent compound 2.

<1-3> Phosphorescent compound 3
The phosphorescent compound 3 was synthesized according to the method described in JP-A-2006-188673.

<1-4> Phosphorescent compound 4
The phosphorescent compound 4 was synthesized according to the method described in JP2013-147551A.

<1-5> Phosphorescent compound 5
The phosphorescent compound 5 was synthesized according to the method described in JP2013-147551A.

<Evaluation of maximum peak wavelength of emission spectrum of phosphorescent compounds 1 to 5>
The maximum peak wavelength of the emission spectra of the phosphorescent compounds 1 to 5 was measured at room temperature with a spectrophotometer (manufactured by JASCO Corporation, FP6500). A xylene solution prepared by dissolving phosphorescent compounds 1 to 5 in xylene at a concentration of about 0.8 × 10 ⁻⁴ wt% was used as a sample. As excitation light, UV light having a wavelength of 325 nm was used. The evaluation results are shown in Table 3.

(2) Synthesis of polymer compound <2-1> compound Ma3

After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Ma2 (64.6 g) and tetrahydrofuran (615 ml) were added and cooled to -70 ° C. An n-butyllithium hexane solution (1.6M, 218 ml) was added dropwise thereto over 1 hour, and the mixture was stirred at -70 ° C for 2 hours. Compound Ma1 (42.1 g) was added thereto in several portions, and the mixture was stirred at -70 ° C for 2 hours. Methanol (40 ml) was added dropwise thereto over 1 hour, and the temperature was raised to room temperature. Then, it concentrated under reduced pressure, the solvent was distilled off, and toluene and water were added.
Thereafter, the aqueous layer was separated, and the obtained organic layer was further washed with water. The obtained organic layer was concentrated under reduced pressure, and the obtained residue was purified using a silica gel column (developing solvent: a mixed solvent of hexane and ethyl acetate) to obtain 71 g of compound Ma3 as a colorless oil. The compound Ma3 obtained had an HPLC area percentage value (UV254 nm) of 97.5%. By repeating this operation, the required amount of Compound Ma3 was obtained.

The ¹ H-NMR measurement result of the obtained compound Ma3 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 2.43 (1H, s), 3.07-3.13 (4H, m), 6.95 (1H, d), 7.07 ( 1H, S), 7.18-7.28 (3H, m), 7.28-7.40 (4H, m), 7.66 (2H, s).

<2-2> Synthesis of Compound Ma4

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Ma3 (72.3 g), toluene (723 ml) and triethylsilane (118.0 g) were added, and the temperature was raised to 70 ° C. Thereto, methanesulfonic acid (97.7 g) was added dropwise over 1.5 hours, followed by stirring at 70 ° C. for 0.5 hours. Then, after cooling to room temperature and adding toluene (1 L) and water (1 L), the water layer was isolate | separated. The obtained organic layer was washed with water, 5 wt% aqueous sodium hydrogen carbonate and water in this order. The obtained organic layer was concentrated under reduced pressure, and the obtained crude product was recrystallized with a mixed solution of toluene and ethanol to obtain 51.8 g of Compound Ma4 as a white solid. The HPLC area percentage value (UV254 nm) of the obtained compound Ma4 was 99.5% or more. By repeating this operation, the required amount of Compound Ma4 was obtained.

The ¹ H-NMR measurement result of the obtained compound Ma4 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 3.03-3.14 (4H, m), 4.99 (1H, s), 6.68 (1H, s), 6.92- 7.01 (2H, m), 7.20-7.28 (2H, m), 7.29-7.38 (4H, m), 7.78 (2H, d).

<2-3> Synthesis of compound Mb3

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Mb1 (185.0 g), Compound Mb2 (121.1 g), CuI (3.2 g), dichloromethane (185 ml) and triethylamine (2.59 L) ) Was added and the temperature was raised to reflux temperature. Then, it stirred at reflux temperature for 0.5 hour and cooled to room temperature. Dichloromethane (1.85 L) was added thereto, followed by filtration with a filter packed with celite. A 10 wt% aqueous sodium hydrogen carbonate solution was added to the obtained filtrate, and then the aqueous layer was separated. The obtained organic layer was washed twice with water, washed with saturated NaCl solution, and then magnesium sulfate was added. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The resulting residue was purified using a silica gel column (developing solvent: a mixed solvent of chloroform and ethyl acetate) to obtain a crude product. The obtained crude product was dissolved in ethanol (1.4 L), and then activated carbon (5 g) was added and filtered. The obtained filtrate was concentrated under reduced pressure, and the obtained residue was recrystallized from hexane to obtain 99.0 g of Compound Mb3 as a white solid. The obtained compound Mb3 had an HPLC area percentage value (UV254 nm) of 99.5% or more. By repeating this operation, the required amount of Compound Mb3 was obtained.

The ¹ H-NMR measurement result of the obtained compound Mb3 is shown below.
¹ H-NMR (DMSO-d ₆ , 300 MHz) δ (ppm): 1.52-1.55 (8H, m), 2.42 (4H, t), 3.38-3.44 (4H, m ), 4.39-4.43 (2H, m), 7.31 (4H, s).

<2-4> Synthesis of compound Mb4

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Mb3 (110.0 g), ethanol (1.65 L) and palladium / carbon (Pd weight 10%) (11.0 g) were added, and 30 The temperature was raised to ° C. Thereafter, the gas in the flask was replaced with hydrogen gas. Then, it stirred at 30 degreeC for 3 hours, supplying hydrogen gas in a flask. Thereafter, the gas in the flask was replaced with nitrogen gas. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The resulting residue was purified using a silica gel column (developing solvent: a mixed solvent of chloroform and ethyl acetate) to obtain a crude product. The obtained crude product was recrystallized with hexane to obtain 93.4 g of Compound Mb4 as a white solid. The obtained compound Mb4 had an HPLC area percentage value (UV254 nm) of 98.3%.

The ¹ H-NMR and ¹³ C-NMR measurement results of the obtained compound Mb4 are shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 1.30-1.40 (8H, m), 1.55-1.65 (8H, m), 2.58 (4H, t), 3.64 (4H, t), 7.09 (4H, s).
¹³ C-NMR (CDCl ₃ , 75 MHz) δ (ppm): 25.53, 28.99, 31.39, 32.62, 35.37, 62.90, 128.18, 139.85.

<2-5> Synthesis of Compound Mb5

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Mb4 (61.0 g), pyridine (0.9 g) and toluene (732 ml) were added, and the temperature was raised to 60 ° C. The thionyl chloride (91.4g) was dripped there over 1.5 hours, Then, it stirred at 60 degreeC for 5 hours. The resulting mixture was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified using a silica gel column (developing solvent: a mixed solvent of hexane and ethyl acetate) to obtain 64.3 g of Compound Mb5 as a colorless oil. The compound Mb5 obtained had an HPLC area percentage value (UV254 nm) of 97.2%.

The ¹ H-NMR measurement result of the obtained compound Mb5 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 1.35 to 1.40 (4H, m), 1.41-1.50 (4H, m), 1.60 to 1.68 (4H) M), 1.75-1.82 (4H, m), 2.60 (4H, t), 3.55 (4H, t), 7.11 (4H, s).

<2-6> Synthesis of Compound Mb6

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Mb5 (42.0 g), iron powder (1.7 g), iodine (0.3 g) and dichloromethane (800 ml) were added. Thereafter, the entire flask was shielded from light and cooled to 0 to 5 ° C. A mixture of bromine (44.7 g) and dichloromethane (200 ml) was added dropwise thereto over 1 hour, and the mixture was stirred overnight at 0 to 5 ° C. The obtained mixture was added to water (1.2 L) cooled to 0 to 5 ° C., and then the organic layer was separated. The obtained organic layer was washed with a 10% by weight aqueous sodium thiosulfate solution, and further washed with a saturated aqueous sodium chloride solution and water in this order. Sodium sulfate was added to the obtained organic layer, followed by filtration, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was purified using a silica gel column (developing solvent hexane) to obtain a crude product. The obtained crude product was recrystallized from hexane to obtain 47.0 g of Compound Mb6 as a white solid. The compound Mb6 obtained had an HPLC area percentage value (UV254 nm) of 98.3%.

The ¹ H-NMR measurement result of the obtained compound Mb6 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 1.38-1.45 (4H, m), 1.47-1.55 (4H, m), 1.57-1.67 (4H M), 1.77-1.84 (4H, m), 2.66 (4H, t), 3.55 (4H, t), 7.36 (2H, s).

<2-7> Synthesis of Compound Mb7

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, sodium iodide (152.1 g) and acetone (600 ml) were added, and the mixture was stirred at room temperature for 0.5 hour. Mb6 (40.0 g) was added thereto, and then the temperature was raised to the reflux temperature and stirred at the reflux temperature for 24 hours. Then, it cooled to room temperature and the obtained liquid mixture was added to water (1.2L). The precipitated solid was filtered off and washed with water to obtain a crude product. The obtained crude product was recrystallized with a mixed solution of toluene and methanol to obtain 46.0 g of Compound Mb7 as a white solid. The obtained compound Mb7 had an HPLC area percentage value (UV254 nm) of 99.4%. By repeating this operation, the required amount of Compound Mb7 was obtained.

The ¹ H-NMR measurement result of the obtained compound Mb7 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 1.35 to 1.50 (8H, m), 1.57 to 1.65 (4H, m), 1.80 to 1.89 (4H) M), 2.65 (4H, t), 3.20 (4H, t), 7.36 (2H, s).

<2-8> Synthesis of Compound Mb8

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, sodium hydride (60 wt%, dispersed in liquid paraffin) (9.4 g), tetrahydrofuran (110 ml) and compound Mb7 (63.2 g) were added. It was. To this, compound Ma4 (55.0 g) was added in several portions, followed by stirring for 12 hours. Thereto, toluene (440 ml) and water (220 ml) were added, and then the aqueous layer was separated. The obtained organic layer was washed with water, and magnesium sulfate was added. The obtained mixed solution was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified using a silica gel column (developing solvent: a mixed solvent of hexane and toluene). Then, 84.1g of compounds Mb8 were obtained as white solid by recrystallizing with heptane. The obtained compound Mb8 had an HPLC area percentage value (UV254 nm) of 99.5% or more.

The ¹ H-NMR measurement result of the obtained compound Mb8 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 0.70 to 0.76 (4H, m), 1.10 to 1.21 (8H, m), 1.32 to 1.44 (4H) M), 2.39-2.58 (8H, m), 3.00-3.12 (8H, m), 6.82-6.94 (4H, m), 7.00-7.05 (2H, m), 7.17-7.28 (10H, m), 7.30-7.38 (4H, m), 7.71-7.77 (4H, m).

<2-9> Synthesis of Compound MM1

After replacing the gas in the flask equipped with a stirrer with nitrogen gas, compound Mb8 (84.0 g), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (PdCl ₂₎ (Dppf) · CH ₂ Cl ₂ , 2.2 g), bispinacolato diboron (68.3 g), potassium acetate (52.8 g) and cyclopentyl methyl ether (840 ml) were added, and the temperature was raised to reflux temperature. Stir at reflux for 5 hours. Then, after cooling to room temperature and adding toluene (500 ml) and water (300 ml), the aqueous layer was separated. After the obtained organic layer was washed with water, activated carbon (18.5 g) was added. The obtained mixed solution was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product.
The obtained crude product was purified using a silica gel column (developing solvent: a mixed solvent of hexane and toluene). Then, 45.8g of compound MM1 was obtained as white solid by repeating operation which recrystallizes with the liquid mixture of toluene and acetonitrile. The obtained compound MM1 had an HPLC area percentage value (UV254 nm) of 99.4%.

The ¹ H-NMR measurement result of the obtained compound MM1 is shown below.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 0.70-0.76 (4H, m), 1.24-1.40 (36H, m), 2.39-2.48 (4H M), 2.66-2.75 (4H, m), 3.00-3.10 (8H, m), 6.76-6.90 (4H, m), 7.00-7.05. (2H, m), 7.19-7.30 (8H, m), 7.30-7.36 (4H, m), 7.43 (2H, s), 7.72 (4H, d).

<2-10> Synthesis of polymer compound P1 Polymer compound P1 was synthesized by the following steps 1 to 4.

(Step 1) After setting the inside of the reaction vessel to an inert gas atmosphere, Compound MM1 (0.81933 g), Compound MM2 (0.09907 g) described in International Publication No. 2013/146806, International Publication No. 2005/049546 Compound MM3 described (0.86215 g), compound MM4 (0.11290 g) described in WO2009 / 157424, dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.76 mg) and toluene (34 mL). In addition, it was heated to 105 ° C.

(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (6.7 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 6 hours.

(Step 3) After the reaction, phenylboronic acid (48.8 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.88 mg) were added thereto and refluxed for 14.5 hours.

(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the resulting reaction solution was washed twice with water, twice with a 3% by weight acetic acid aqueous solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred. The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.22 g of polymer compound P1.

The polymer compound P1 had a polystyrene-equivalent number average molecular weight of 3.0 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.7 × 10 ⁵ .

  The theoretical value obtained from the amount of the raw material used for the polymer compound P1 is that the structural unit formed from the compound MM1, the structural unit formed from the compound MM2, the structural unit formed from the compound MM3, and the compound MM4 It is a copolymer containing the structural unit to be formed at a molar ratio of 40: 10: 47: 3. With respect to the polymer compound P1, the average number of crosslinking groups per molecular weight of 1000 calculated by the above method was 1.36.

<2-11> Synthesis of polymer compound P2 Polymer compound P2 was synthesized by the following method.

  0.98 g of polymer compound P2 was obtained by the same method as the synthesis of polymer compound P1, except that (Step 1) in the synthesis of polymer compound P1 was changed to the following (Step 1-2). It was.

(Step 1-2) After the inside of the reaction vessel is filled with an inert gas atmosphere, Compound MM1 (0.10369 g), Compound MM2 (0.04951 g), Compound MM5 described in JP 2010-189630 A (0.39465 g) ), Compound MM3 (0.86213 g), compound MM4 (0.11563 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.76 mg) and toluene (30 mL) were added and heated to 105 ° C.

The polymer compound P2 had a polystyrene-equivalent number average molecular weight of 4.8 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.0 × 10 ⁵ .

  The theoretical value obtained from the amount of charged raw materials for polymer compound P2 is that the structural unit formed from compound MM1, the structural unit formed from compound MM2, the structural unit formed from compound MM5, and the compound MM3 It is a copolymer containing the structural unit formed and the structural unit formed from the compound MM4 in a molar ratio of 5: 5: 40: 47: 3. For the polymer compound P2, the average number of crosslinking groups per 1000 molecular weights calculated by the above method was 0.36.

<2-12> Synthesis of Compound Mc1

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, sodium hydride (60% by weight, dispersed in liquid paraffin) (10.9 g), tetrahydrofuran (268 ml) and 1-bromo-6-chlorohexane (198.3 g) was added. Thereafter, the entire flask was shielded from light and cooled to 0 to 5 ° C. Thereto was added a mixture of compound Ma4 (67.0 g) and tetrahydrofuran (330 ml) over 2.5 hours, and then the mixture was heated to 50 ° C. and stirred at 50 ° C. for 6 hours. Thereto were added heptane (536 ml) and water (268 ml), and the aqueous layer was separated. The obtained organic layer was washed with water, and magnesium sulfate was added. The obtained mixed solution was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized from isopropanol, and the obtained crystal was dissolved in a mixed solution of toluene and heptane, and activated carbon (9.6 g) was added. The obtained mixed solution was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was recrystallized with a mixed solution of toluene and heptane to obtain 81.0 g of Compound Mc1 as a white solid. The obtained compound Mc1 had an HPLC area percentage value (UV254 nm) of 99.5%. By repeating this operation, the required amount of compound Mc1 was obtained.

The ¹ H-NMR measurement result of the obtained compound Mc1 is shown below.
¹ H-NMR (CD ₂ Cl ₂ , 300 MHz) δ (ppm): 0.71-0.83 (2H, m), 1.27 (4H, t), 1.58-1.68 (2H, m ), 2.49-2.54 (2H, m), 3.08-3.19 (4H, m), 3.49 (2H, t), 6.89 (1H, s), 6.94 ( 1H, d), 7.07 (1H, d), 7.25-7.44 (6H, m), 7.83 (2H, d).

<2-13> Synthesis of Compound Mc2

  After replacing the gas in the flask equipped with a stirrer with nitrogen gas, Compound Mc1 (124.4 g), sodium iodide (385.5 g) and acetone (786 ml) were added, and the temperature was raised to the reflux temperature. Stir at reflux for 34 hours. Then, it cooled to room temperature and added the heptane, toluene, and water to the obtained liquid mixture, and isolate | separated the water layer. The obtained organic layer was washed with water, and magnesium sulfate was added. The obtained mixed solution was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized with a mixed solution of heptane and isopropanol to obtain 143 g of compound Mc2 as a white solid. The obtained compound Mc2 had an HPLC area percentage value (UV254 nm) of 99.4%.

The ¹ H-NMR measurement result of the obtained compound Mc2 is shown below.
¹ H-NMR (CD ₂ Cl ₂ , 300 MHz) δ (ppm): 0.71-0.83 (2H, m), 1.20-1.36 (4H, m), 1.60-1.70 (2H, m), 2.48-2.54 (2H, m), 3.13-3.18 (6H, m), 6.89 (1H, s), 6.94 (1H, d), 7.07 (1H, d), 7.25-7.44 (6H, m), 7.83 (2H, d).

<2-14> Synthesis of Compound Mc4

After replacing the gas in the flask equipped with a stirrer with nitrogen gas, sodium hydride (60% by weight, dispersed in liquid paraffin) (1.0 g), tetrahydrofuran (42.5 ml), N, N-dimethylformamide ( 42.5 ml) and Mc2 (10.8 g) were added.
Thereafter, the entire flask was shielded from light and cooled to 0 to 5 ° C. Thereto was added a mixture of compound Mc3 (10.6 g) and tetrahydrofuran (42.5 ml) synthesized according to the synthesis method described in JP-T-2014-506609 over 1 hour, and then at 0 to 5 ° C. for 4 hours. Stir.
The resulting reaction mixture was warmed to room temperature, toluene (106 ml) and water (106 ml) were added, and the aqueous layer was separated. The obtained organic layer was washed with water, and then sodium sulfate was added. The obtained mixed liquid was filtered with a filter packed with silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was recrystallized with a mixed solution of ethyl acetate and acetonitrile to obtain 14.3 g of compound Mc4 as a white solid. The obtained compound Mc4 had an HPLC area percentage value (UV254 nm) of 99.5% or more.

The LC-MS measurement result of the obtained compound Mc4 is shown below.
LC-MS (positive) m / z: 955 ([M + K] ⁺ )

The ¹ H-NMR measurement result of the obtained compound Mc4 is shown below.
¹ H-NMR (CD ₂ Cl ₂ , 300 MHz) δ (ppm): 0.56-0.65 (4H, m), 0.90-1.32 (22H, m), 1.54-1.58 (4H, m), 2.34-2.42 (4H, m), 2.52 (4H, t), 3.12 (4H, d), 6.74 (2H, s), 6.85 ( 1H, s), 6.92 (2H, d), 7.00-7.05 (1H, m), 7.19 (2H, d), 7.26-7.41 (6H, m), 7 .53 (2H, d), 7.65 (2H, d), 7.80 (2H, d).

<2-15> Synthesis of Compound MM6

After replacing the gas in the flask equipped with a stirrer with nitrogen gas, compound Mc4 (14.3 g), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (PdCl 2 ( dppf) · CH ₂ Cl ₂ , 0.51 g), bispinacolatodiboron (9.5 g), potassium acetate (9.3 g) and 1,2-dimethoxyethane (143 ml) were added, and the temperature was raised to reflux temperature. Thereafter, the mixture was stirred at reflux temperature for 12 hours. The obtained reaction mixture was cooled to room temperature, toluene (143 ml) was added, and the mixture was filtered through a filter packed with celite. The obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was dissolved in a mixed solution of toluene (173 ml) and heptane (173 ml), activated carbon (4.6 g) was added, and the mixture was filtered through a filter packed with silica gel and celite. The obtained filtrate was concentrated under reduced pressure, and the operation of recrystallizing the obtained residue with a mixed solution of ethyl acetate and acetonitrile was repeated to obtain 11.2 g of compound MM6 as a white solid. The obtained compound MM6 had an HPLC area percentage value (UV254 nm) of 99.5%.

The LC-MS measurement result of the obtained compound MM6 is shown below.
LC-MS (positive) m / z: 1031 ([M + NH ₄ ] ⁺ )

The ¹ H-NMR measurement result of the obtained compound MM6 is shown below.
¹ H-NMR (CD ₂ Cl ₂ , 300 MHz) δ (ppm): 0.50-0.68 (4H, m), 0.90-1.00 (10H, m), 1.31-1.58 (40H, m), 2.34-2.53 (8H, m), 3.12 (4H, s), 6.76 (2H, s), 6.83 (1H, s), 6.90 ( 2H, d), 6.98-7.04 (1H, m), 7.17 (2H, d), 7.27 (2H, t), 7.37 (2H, t), 7.55 (2H , S), 7.77-7.83 (6H, m).

<2-16> Synthesis of polymer compound P3 Polymer compound P3 was synthesized by the following method.

  1.19 g of polymer compound P3 was obtained by the same method as the synthesis of polymer compound P1, except that (Step 1) in the synthesis of polymer compound P1 was changed to the following (Step 1-3). It was.

(Step 1-3) After the inside of the reaction vessel is filled with an inert gas atmosphere, Compound MM6 (0.80419 g), Compound MM7 (0.11088 g) described in International Publication No. 2013/200988, Compound MM3 (0.86213 g) ), Compound MM4 (0.11288 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.88 mg) and toluene (34 mL) were added and heated to 105 ° C.

The polymer compound P3 had a polystyrene-equivalent number average molecular weight of 3.0 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.0 × 10 ⁵ .

  The theoretical value obtained from the amount of charged raw material for polymer compound P3 is that the structural unit formed from compound MM6, the structural unit formed from compound MM7, the structural unit formed from compound MM3, and the compound MM4 It is a copolymer containing the structural unit to be formed at a molar ratio of 40: 10: 47: 3. For the polymer compound P3, the average number of crosslinking groups per 1000 molecular weights calculated by the above method was 0.82.

<2-17> Synthesis of polymer compound P4 Polymer compound P4 was synthesized by the following method.

  In the synthesis of the polymer compound P1, (Step 1) is changed to the following (Step 1-4), (Step 2) is changed to the following (Step 2-4), and (Step 3) is changed to the following (Step 3- Except for changing to 4), 2.01 g of the polymer compound P4 was obtained by the same method as the synthesis of the polymer compound P1.

(Step 1-4) After setting the inside of the reaction vessel to an inert gas atmosphere, Compound MM12 (0.27281 g), Compound MM3 (0.37418 g), Compound MM4 (0.16929 g) described in JP2011-174062 A ), Dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.44 mg) and toluene (31 mL) were added and heated to 105 ° C.

(Step 2-4) A 20 wt% tetraethylammonium hydroxide aqueous solution (10.0 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 3.5 hours, and then compound MM1 (0.92538 g), compound MM7 (0.16637 g). ), Compound MM3 (0.91904 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.88 mg) and toluene (13 mL) were added, and the mixture was further refluxed for 6 hours.

(Step 3-4) After the reaction, phenylboronic acid (73.2 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.32 mg) were added thereto and refluxed for 14.5 hours.

The polymer compound P4 had a polystyrene-equivalent number average molecular weight of 3.3 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 1.7 × 10 ⁵ .

  The theoretical value obtained from the amount of the raw material used for polymer compound P4 is that the structural unit formed from compound MM12, the structural unit formed from compound MM1, the structural unit formed from compound MM7, and the compound MM3 It is a copolymer containing the structural unit to be formed and the structural unit formed from the compound MM4 in a molar ratio of 10: 30: 10: 47: 3. For the polymer compound P4, the average number of crosslinking groups per 1,000 molecular weights calculated by the above method was 1.09.

<2-18> Synthesis of polymer compound P5 Polymer compound P5 was synthesized by the following method.

  In the synthesis of the polymer compound P1, (Step 1) is changed to the following (Step 1-5), (Step 2) is changed to the following (Step 2-5), and (Step 3) is changed to the following (Step 3). Except that it was changed to 5), 1.26 g of the polymer compound P5 was obtained by the same method as the synthesis of the polymer compound P1.

(Step 1-5) After making the inside of the reaction vessel an inert gas atmosphere, Compound MM1 (1.23596 g), Compound MM2 (0.14849 g), Compound MM13 described in JP-A-2007-511636 (0.60981 g) ), Compound MM4 (0.16851 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (2.64 mg) and toluene (31 mL) were added and heated to 105 ° C.

(Step 2-5) A 16 wt% tetraethylammonium hydroxide aqueous solution (20.7 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 6 hours.

(Step 3-5) After the reaction, phenylboronic acid (73.2 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.32 mg) were added thereto and refluxed for 14.5 hours.

The polymer compound P5 had a polystyrene-equivalent number average molecular weight of 3.7 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 1.7 × 10 ⁵ .

  The theoretical value obtained from the amount of raw materials used for polymer compound P5 is that the structural unit formed from compound MM1, the structural unit formed from compound MM2, the structural unit formed from compound MM13, and the compound MM4 It is a copolymer containing the structural unit to be formed at a molar ratio of 40: 10: 47: 3. For the polymer compound P5, the average number of crosslinking groups per molecular weight of 1000 calculated by the above method was 2.87.

<Evaluation of phosphorescence emission spectra of polymer compounds P1 to P5>
<Evaluation Example E1> Production and Evaluation of Light-Emitting Element E1 An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, AQ-1200 (manufactured by Spectronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed into a film having a thickness of 35 nm by a spin coating method. The hole injection layer was formed by heating for 15 minutes.

  Polymer compound P1 was dissolved in xylene at a concentration of 1.8% by weight. Using the obtained xylene solution, a film having a thickness of 70 nm is formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a light emitting layer Formed.

On the light emitting layer, about 7 nm of sodium fluoride and then about 120 nm of aluminum were vapor-deposited as a cathode, and the light emitting element E1 was produced. In addition, after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, metal deposition was started.

  When a voltage of 12 V was applied to the light emitting element E1, EL light emission (emission peak wavelength: 600 nm) derived from the structural unit obtained from the compound MM4 was obtained.

<Evaluation Example E2> Production and Evaluation of Light-Emitting Element E2 A light-emitting element E2 was produced in the same manner as in Evaluation Example E1, except that the polymer compound P2 was used instead of the polymer compound P1.

  When a voltage of 12 V was applied to the light emitting element E2, EL light emission (emission peak wavelength: 600 nm) derived from the structural unit obtained from the compound MM4 was obtained.

<Evaluation Example E3> Production and Evaluation of Light-Emitting Element E3 A light-emitting element E3 was produced in the same manner as in Evaluation Example E1, except that the polymer compound P3 was used instead of the polymer compound P1.

  When a voltage of 12 V was applied to the light-emitting element E3, EL light emission (emission peak wavelength: 605 nm) derived from the structural unit obtained from the compound MM4 was obtained.

<Evaluation Example E4> Production and Evaluation of Light-Emitting Element E4 A light-emitting element E4 was produced in the same manner as in Evaluation Example E1, except that the polymer compound P4 was used instead of the polymer compound P1.

  When a voltage of 12 V was applied to the light-emitting element E4, EL light emission (emission peak wavelength: 605 nm) derived from the structural unit obtained from the compound MM4 was obtained.

<Evaluation Example E5> Production and Evaluation of Light-Emitting Element E5 A light-emitting element E5 was produced in the same manner as in Evaluation Example E1, except that the polymer compound P5 was used instead of the polymer compound P1.

  When a voltage of 12 V was applied to the light-emitting element E5, EL light emission (emission peak wavelength: 605 nm) derived from the structural unit obtained from the compound MM4 was obtained.

(3) Other polymer compounds

<3-1> Synthesis of Polymer Compound E1 Polymer compound E1 was synthesized by the following method.

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound MM5 (2.2 g), Compound MM8 (1.3 g) described in International Publication No. 2013/191888, dichlorobis (tris-o-methoxyphenyl) Phosphine) palladium (2.3 mg) and toluene (55 mL) were added and heated to 105 ° C.
(Step 2) Thereafter, a 20 wt% tetraethylammonium hydroxide aqueous solution (9.1 g) was dropped therein and refluxed for 4 hours.
(Step 3) Then, 2-isopropylphenylboronic acid (0.47 g) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (2.2 mg) were added thereto and refluxed for 16 hours.
(Step 4) Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, and the mixture was stirred at 85 ° C. for 5 hours. The obtained reaction solution was cooled, washed with hydrochloric acid, aqueous ammonia and ion-exchanged water, and the resulting organic layer was added dropwise to methanol, resulting in precipitation. The solid obtained by filtering the precipitate and drying was dissolved in toluene, and purified by passing through an alumina column and a silica gel column through which toluene was passed in advance in order. When the obtained purified solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain polymer compound E1 (2.3 g).

The polymer compound E1 had a polystyrene-equivalent number average molecular weight of 7.4 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.3 × 10 ⁵ .

  The polymer compound E1 is a copolymer containing a structural unit formed from the compound MM5 and a structural unit formed from the compound MM8 in a molar ratio of 50:50 according to the theoretical value obtained from the amount of the raw materials charged. is there.

<3-2> Synthesis of polymer compound E2 Polymer compound E2 was synthesized by the following method.

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, compound MM9 (9.23 g), compound MM5 (4.58 g), dichlorobis (tris-) synthesized according to the method described in JP 2012-33845 A o-Methoxyphenylphosphine) palladium (8.6 mg) and toluene (175 mL) were added and heated to 105 ° C.
(Step 2) Then, a 12 wt% aqueous sodium carbonate solution (40.3 mL) was added dropwise thereto and refluxed for 29 hours.
(Step 3) Thereafter, phenylboronic acid (0.47 g) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (8.7 mg) were added thereto and refluxed for 14 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. When the obtained reaction solution was cooled and dropped into methanol, precipitation occurred. The precipitate was collected by filtration, washed with methanol and water, and then dried, and the solid obtained was dissolved in chloroform and purified by passing through an alumina column and a silica gel column through which chloroform was passed in advance in this order. When the obtained purified solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain 7.15 g of polymer compound E2.

The polymer compound E2 had a polystyrene-equivalent number average molecular weight of 3.2 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 6.0 × 10 ⁴ .

  The polymer compound E2 is a copolymer that includes a structural unit formed from the compound MM9 and a structural unit formed from the compound MM5 in a molar ratio of 50:50 according to the theoretical value obtained from the amount of the raw materials charged. is there.

<3-3> Synthesis of Polymer Compound E3 (Step 1) Polymer compound E2 (3.1 g) was added to the reaction vessel, and then the atmosphere in the reaction vessel was changed to an argon gas atmosphere. Then, tetrahydrofuran (130 mL) and methanol (66 mL), cesium hydroxide monohydrate (2.1 g) and water (12.5 mL) were added thereto, and the mixture was stirred at 60 ° C. for 3 hours.
(Step 2) Thereafter, methanol (220 mL) was added thereto and stirred for 2 hours. The obtained reaction mixture was concentrated and then added dropwise to isopropyl alcohol, followed by stirring. As a result, precipitation occurred. The precipitate was collected by filtration and dried to obtain polymer compound E3 (3.5 g).

  The polymer compound E3 is a copolymer composed of the following structural units in theory.

<3-4> Synthesis of polymer compound E4 Polymer compound E4 was synthesized by the following method.

  The polymer compound E4 was synthesized according to the method described in JP2012-36388A using the compound MM5, the compound MM10 described in International Publication No. 2012/86671, and the compound MM11 described in JP2010-189630A. did.

The polymer compound E4 had a polystyrene-equivalent number average molecular weight of 8.2 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.1 × 10 ⁵ .

  The theoretical value obtained from the amount of the raw material used for the polymer compound E4 was 50: a structural unit formed from the compound MM5, a structural unit formed from the compound MM10, and a structural unit formed from the compound MM11. It is a copolymer containing a molar ratio of 40:10.

[Example 1] Production and evaluation of light-emitting element 1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is formed on the hole injection layer by spin coating, and heated at 180 ° C. for 10 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Toluene was added 2,8-di (9H-carbazol-9-yl) dibenzo [b, d] thiophene (DCzDBT) (manufactured by Luminescence Technology Corp) and phosphorescent compound 1 (DCzDBT / phosphorescent compound 1 = 75). % By weight / 25% by weight) was dissolved at a concentration of 2.0% by weight. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound E3 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was formed on the light emitting layer as the cathode, and then on the sodium fluoride layer. Aluminum was evaporated to about 80 nm. After vapor deposition, the light emitting element 1 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 1. When the drive voltage was 6.2 [V], it showed 250 cd / m ² , the power efficiency was 13.4 lm / W, and the chromaticity coordinates (x, y) were (0.51, 0.40).

[Example 2] Production and evaluation of light-emitting element 2 (production of light-emitting element)
A light emitting device 2 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 90: 10 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 2. When the drive voltage was 6.6 [V], it showed 250 cd / m ² , the power efficiency was 12.0 lm / W, and the chromaticity coordinates (x, y) were (0.52, 0.40).

[Example 3] Production and evaluation of light-emitting element 3 (production of light-emitting element)
A light emitting device 3 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 80: 20 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
When a voltage was applied to the light emitting element 3, EL light emission was observed. When the driving voltage was 6.8 [V], it showed 250 cd / m ² , the power efficiency was 10.9 lm / W, and the chromaticity coordinates (x, y) were (0.53, 0.40).

[Example 4] Production and evaluation of light-emitting element 4 (production of light-emitting element)
A light emitting device 4 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 70: 30 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 4. When the drive voltage was 6.8 [V], it showed 250 cd / m ² , the power efficiency was 10.6 lm / W, and the chromaticity coordinates (x, y) were (0.54, 0.40).

[Example 5] Production and evaluation of light-emitting element 5 (production of light-emitting element)
A light emitting device 5 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 60: 40 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 5. When the drive voltage was 6.5 [V], it showed 250 cd / m ² , the power efficiency was 10.5 lm / W, and the chromaticity coordinates (x, y) were (0.54, 0.40).

[Example 6] Production and evaluation of light-emitting element 6 (production of light-emitting element)
A light emitting device 6 was produced in the same manner as in Example 1 except that the composition of polymer compound P1: polymer compound P2 = 50: 50 was used instead of polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 6. When the drive voltage was 6.6 [V], it showed 250 cd / m ² , the power efficiency was 10.3 lm / W, and the chromaticity coordinates (x, y) were (0.54, 0.40).

[Example 7] Production and evaluation of light-emitting element 7 (production of light-emitting element)
A light emitting device 7 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 40: 60 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 7. When the drive voltage was 7.2 [V], it showed 250 cd / m ² , the power efficiency was 10.3 lm / W, and the chromaticity coordinates (x, y) were (0.52, 0.41).

[Example 8] Production and evaluation of light-emitting element 8 (production of light-emitting element)
A light emitting device 8 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 30: 70 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 8. When the drive voltage was 7.1 [V], it showed 250 cd / m ² , the power efficiency was 10.5 lm / W, and the chromaticity coordinates (x, y) were (0.53, 0.40).

[Comparative Example 1] Production and evaluation of light-emitting element C1 (production of light-emitting element)
A light emitting device C1 was produced in the same manner as in Example 1 except that the composition of the polymer compound P1: polymer compound P2 = 10: 90 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C1. When the drive voltage was 7.1 [V], it showed 250 cd / m ² , the power efficiency was 9.5 lm / W, and the chromaticity coordinates (x, y) were (0.53, 0.40).

[Comparative Example 2] Production and evaluation of light-emitting element C2 (production of light-emitting element)
A light emitting device C2 was produced in the same manner as in Example 1 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C2. When the drive voltage was 6.4 [V], it showed 250 cd / m ² , the power efficiency was 9.4 lm / W, and the chromaticity coordinates (x, y) were (0.55, 0.40).

  Table 4 shows the results of Examples 1 to 7 and Comparative Examples 1 and 2.

[Example 9] Production and evaluation of light-emitting element 9 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is formed on the hole injection layer by spin coating, and heated at 180 ° C. for 10 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Polymer compound E1 and phosphorescent compound 2 (polymer compound E1 / phosphorescent compound 2 = 75 wt% / 25 wt%) were dissolved in xylene at a concentration of 1.5 wt%. Using the obtained xylene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound E3 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was formed on the light emitting layer as the cathode, and then on the sodium fluoride layer. Aluminum was evaporated to about 80 nm. The light emitting element 9 was produced by sealing using a glass substrate after vapor deposition.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 9. When the driving voltage was 7.40 [V], it showed 250 cd / m ² , the power efficiency was 13.2 lm / W, and the chromaticity coordinates (x, y) were (0.35, 0.39).

[Comparative Example 3] Production and evaluation of light-emitting element C3 (production of light-emitting element)
A light emitting device C3 was produced in the same manner as in Example 9 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C3. When the drive voltage was 8.33 [V], it showed 250 cd / m ² , the power efficiency was 9.4 lm / W, and the chromaticity coordinates (x, y) were (0.38, 0.38).

  The results of Example 9 and Comparative Example 3 are shown in Table 5.

[Example 10] Production and evaluation of light-emitting element 10 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Toluene, 2,8-di (9H-carbazol-9-yl) dibenzo [b, d] thiophene (DCzDBT) (manufactured by Luminescence Technology Corp), phosphorescent compound 2 and phosphorescent compound 3 (DCzDBT / phosphorescent) Luminescent Compound 2 / Phosphorescent Compound 3 = 74 wt% / 25 wt% / 1 wt%) was dissolved at a concentration of 2.0 wt%. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound E3 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was formed on the light emitting layer as the cathode, and then on the sodium fluoride layer. Aluminum was evaporated to about 80 nm. The light emitting element 10 was produced by sealing using a glass substrate after vapor deposition.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 10. When the drive voltage was 6.1 [V], it was 1000 cd / m ² , the power efficiency was 19.1 lm / W, and the chromaticity coordinates (x, y) were (0.43, 0.47).

[Example 11] Production and evaluation of light-emitting element 11 (production of light-emitting element)
A light emitting device 11 was produced in the same manner as in Example 10 except that the polymer compound P3 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 11. When the drive voltage was 5.2 [V], it was 1000 cd / m ² , the power efficiency was 21.6 lm / W, and the chromaticity coordinates (x, y) were (0.44, 0.45).

[Example 12] Production and evaluation of light-emitting element 12 (production of light-emitting element)
A light emitting device 12 was produced in the same manner as in Example 10 except that the polymer compound P4 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 12. When the drive voltage was 5.4 [V], it was 1000 cd / m ² , the power efficiency was 18.5 lm / W, and the chromaticity coordinates (x, y) were (0.48, 0.44).

[Comparative Example 4] Production and evaluation of light-emitting element C4 (production of light-emitting element)
A light emitting device C4 was produced in the same manner as in Example 10 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C4. When the drive voltage was 6.9 [V], it was 1000 cd / m ² , the power efficiency was 15.3 lm / W, and the chromaticity coordinates (x, y) were (0.48, 0.44).

  Table 6 shows the results of Examples 10 to 12 and Comparative Example 4.

[Example 13] Production and evaluation of light-emitting element 13 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 65 nm by a spin coating method, and was 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Polymer compound E4 and phosphorescent compound 3 (polymer compound E4 / phosphorescent compound 3 = 60 wt% / 40 wt%) were dissolved in xylene at a concentration of 1.8 wt%. Using the obtained xylene solution, a film having a thickness of 80 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 150 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of cathode)
After reducing the pressure of the substrate on which the light emitting layer is formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride is about 4 nm on the light emitting layer as a cathode, and then on the sodium fluoride layer. Aluminum was deposited at about 80 nm. After vapor deposition, the light emitting element 13 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 13. When the drive voltage was 5.25 [V], it was 1000 cd / m ² , the power efficiency was 36.4 lm / W, and the chromaticity coordinates (x, y) were (0.40, 0.56).

[Comparative Example 5] Production and evaluation of light-emitting element C5 (production of light-emitting element)
A light emitting device C5 was produced in the same manner as in Example 13 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C5. When the drive voltage was 5.13 [V], it was 1000 cd / m ² , the power efficiency was 33.4 lm / W, and the chromaticity coordinates (x, y) were (0.42, 0.55).

  Table 7 shows the results of Example 13 and Comparative Example 5.

[Example 14] Production and evaluation of light-emitting element 14 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Toluene, 2,8-di (9H-carbazol-9-yl) dibenzo [b, d] thiophene (DCzDBT) (manufactured by Luminescence Technology Corp), phosphorescent compound 4 and phosphorescent compound 3 (DCzDBT / phosphorescent) (Luminescent Compound 4 / Phosphorescent Compound 3 = 74 wt% / 25 wt% / 1 wt%) was dissolved at a concentration of 2.0 wt%. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound E3 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was formed on the light emitting layer as the cathode, and then on the sodium fluoride layer. Aluminum was evaporated to about 80 nm. After vapor deposition, the light emitting element 14 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 14. When the drive voltage was 3.9 [V], it was 1000 cd / m ² , the power efficiency was 29.0 lm / W, and the chromaticity coordinates (x, y) were (0.55, 0.41).

[Comparative Example 6] Production and evaluation of light-emitting element C6 (production of light-emitting element)
A light emitting device C6 was produced in the same manner as in Example 14 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C6. When the drive voltage was 4.4 [V], it showed 1000 cd / m ² , the power efficiency was 22.9 lm / W, and the chromaticity coordinates (x, y) were (0.54, 0.42).

  The results of Example 14 and Comparative Example 6 are shown in Table 8.

[Example 15] Production and evaluation of light-emitting element 15 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Toluene, 2,8-di (9H-carbazol-9-yl) dibenzo [b, d] thiophene (DCzDBT) (manufactured by Luminescence Technology Corp), phosphorescent compound 4 (DCzDBT / phosphorescent compound 4 = 75) % By weight / 25% by weight) was dissolved at a concentration of 2.0% by weight. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound E3 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was formed on the light emitting layer as the cathode, and then on the sodium fluoride layer. Aluminum was evaporated to about 80 nm. After vapor deposition, the light emitting element 15 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 15. When the drive voltage was 3.9 [V], it was 1000 cd / m ² , the power efficiency was 26.3 lm / W, and the chromaticity coordinates (x, y) were (0.56, 0.39).

[Example 16] Production and evaluation of light-emitting element 16 (production of light-emitting element)
A light emitting device 16 was produced in the same manner as in Example 15 except that the polymer compound P5 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 16. When the drive voltage was 4.4 [V], it showed 1000 cd / m ² , the power efficiency was 24.0 lm / W, and the chromaticity coordinates (x, y) were (0.46, 0.35).

[Comparative Example 7] Production and evaluation of light-emitting element C7 (production of light-emitting element)
A light emitting device C7 was produced in the same manner as in Example 15 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C7. When the drive voltage was 4.3 [V], it was 1000 cd / m ² , the power efficiency was 13.7 lm / W, and the chromaticity coordinates (x, y) were (0.57, 0.39).

  Table 9 shows the results of Examples 15 to 16 and Comparative Example 7.

[Example 17] Production and evaluation of light-emitting element 17 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
Polymer compound P1 was dissolved in xylene at a concentration of 0.7% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Toluene, 2,8-di (9H-carbazol-9-yl) dibenzo [b, d] thiophene (DCzDBT) (manufactured by Luminescence Technology Corp), phosphorescent compound 5 (DCzDBT / phosphorescent compound 5 = 75) % By weight / 25% by weight) was dissolved at a concentration of 2.0% by weight. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound E3 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, about 4 nm of sodium fluoride was formed on the light emitting layer as the cathode, and then on the sodium fluoride layer. Aluminum was evaporated to about 80 nm. After vapor deposition, the light emitting element 17 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 17. When the drive voltage was 3.2 [V], it was 1000 cd / m ² , the power efficiency was 38.9 lm / W, and the chromaticity coordinates (x, y) were (0.55, 0.40).

[Example 18] Production and evaluation of light-emitting element 18 (production of light-emitting element)
A light emitting device 18 was produced in the same manner as in Example 17 except that the polymer compound P5 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 18. When the drive voltage was 4.1 [V], it was 1000 cd / m ² , the power efficiency was 28.3 lm / W, and the chromaticity coordinates (x, y) were (0.44, 0.38).

[Comparative Example 8] Production and evaluation of light-emitting element C8 (production of light-emitting element)
A light emitting device C8 was produced in the same manner as in Example 17 except that the polymer compound P2 was used instead of the polymer compound P1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element C8. When the drive voltage was 3.7 [V], it was 1000 cd / m ² , the power efficiency was 16.9 lm / W, and the chromaticity coordinates (x, y) were (0.55, 0.40).

  Table 10 shows the results of Examples 17 to 18 and Comparative Example 8.

  ADVANTAGE OF THE INVENTION According to this invention, the light emitting element excellent in power efficiency is provided. The light emitting device according to the present invention can be suitably used for a planar light source, a display device, and the like, and is excellent in industrial applicability.

Claims (9)

The anode,
A cathode,
A first organic layer provided between the anode and the cathode;
A light emitting device having a second organic layer provided between the anode and the first organic layer,
The first organic layer comprises a phosphorescent compound;
The second organic layer includes a polymer cured product formed from a polymer composition in which one or more polymer compounds are blended,
At least one of the polymer compounds has a crosslinking group,
At least one of the polymer compounds includes a phosphorescent constituent unit;
For each monomer unit constituting the polymer compound, a value x obtained by multiplying the molar ratio C of the monomer unit to the total mole of all monomer units and the molecular weight M of the monomer unit, and When a value y obtained by multiplying the molar ratio C by the number n of the cross-linking groups of the monomer unit is obtained, it is calculated from the sum X _{1 of} x and the sum Y _{1 of} y (Y ₁ × 1000) / X ₁ is a light emitting element having a value of 0.6 or more. The light-emitting element according to claim ₁ , wherein the value of (Y ₁ × 1000) / X ₁ is 1.2 or more. The light emitting element of Claim 1 or 2 in which at least 1 sort (s) of the said high molecular compound contains the structural unit represented by Formula (2).

[Where:
nA represents an integer of 0 to 5, and n represents 1 or 2.
Ar ¹ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of ^LA are present, they may be the same or different.
X represents a crosslinking group. When two or more X exists, they may be the same or different. ] The light emitting element of Claim 1 or 2 in which at least 1 sort (s) of the said high molecular compound contains the structural unit represented by Formula (3).

[Where:
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When a plurality of mA are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar ² and Ar ⁴ each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ² , Ar ³ and Ar ⁴ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom, to form a ring. It may be.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR '' - represents a group represented by an oxygen atom or a sulfur atom in these groups have a substituent May be. R ″ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of K ^A are present, they may be the same or different.
X ′ represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of X ′ are present, they may be the same or different. However, at least one X ′ is a bridging group. ] The light emitting device according to claim 1, wherein at least one of the polymer compounds has at least one crosslinking group selected from the crosslinking group A group.

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * Represents a bonding position. These crosslinkable groups may have a substituent. ] At least one of the polymer compounds is represented by a structural unit represented by the formula (1G), a structural unit represented by the formula (2G), a structural unit represented by the formula (3G), and a formula (4G). The light emitting element according to claim 1, comprising at least one structural unit selected from the group consisting of:

[Where:
M ^1G represents a group formed by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound.
L ¹ is an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, —C (R ^B ) = C (R ^B ) — Represents a group represented by the formula: -C≡C-, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. R ^B 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 ^RBs 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. When a plurality of L ¹ are present, they may be the same or different.
n ^a1 represents an integer of 0 or more. ]

[Where:
M ^1G represents a group formed by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound.
L ² and L ³ are each independently an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, or —C (R ^B ). A group represented by ═C (R ^B ) —, a group represented by —C≡C—, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. R ^B 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 ^RBs 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. When a plurality of L ² and L ³ are present, they may be the same or different.
n ^b1 and n ^c1 each independently represent an integer of 0 or more. A plurality of n ^b1 may be the same or different.
Ar ^1M represents a trivalent aromatic hydrocarbon group or a trivalent heterocyclic group, and these groups optionally have a substituent. ]

[Where:
M ^2G represents a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound.
L ² is an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, —C (R ^B ) = C (R ^B ) — Represents a group represented by the formula: -C≡C-, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. R ^B 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 ^RBs 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. When a plurality of L ² are present, they may be the same or different.
n ^b1 each independently represents an integer of 0 or more. A plurality of n ^b1 may be the same or different. ]

[Where:
M ^3G represents a group obtained by removing three hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the compound from the phosphorescent compound.
L ² is an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, —C (R ^B ) = C (R ^B ) — Represents a group represented by the formula: -C≡C-, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. R ^B 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 ^RBs 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. When a plurality of L ² are present, they may be the same or different.
n ^b1 each independently represents an integer of 0 or more. A plurality of n ^b1 may be the same or different. ]   The light-emitting element according to claim 1, wherein in the polymer compound including the phosphorescent structural unit, the phosphorescent structural unit is bonded to a benzene ring having no substituent at the ortho position. . The phosphorescent compound contained in the first organic layer is selected from the group consisting of a phosphorescent compound represented by formula (1-A) and a phosphorescent compound represented by formula (1-B) The light emitting device according to claim 1, wherein the light emitting device is at least one phosphorescent compound.

[Where:
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹ represents an integer of ¹ to 3, n ² represents an integer of 0 to 2, and n ¹ + n ² represents 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹ + n ² is 3, and when M is a palladium atom or platinum atom, n ¹ + n ² is 2.
E ¹ represents a carbon atom or a nitrogen atom. When a plurality of E ¹ are present, they may be the same or different.
^E11A , ^E12A , ^E13A , ^E21A , ^E22A , ^E23A and ^E24A each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^11A , E ^12A , E ^13A , E ^21A , E ^22A , E ^23A and E ^24A are present, they may be the same or different. When E ^11A , E ^12A and E ^13A are nitrogen atoms, R ^11A , R ^12A and R ^13A may be present or absent. When E ^21A , E ^22A , E ^23A and E ^24A are nitrogen atoms, R ^21A , R ^22A , R ^23A and R ^24A are not present.
R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A , they may be the same or different. R ^11A and R ^12A , R ^12A and R ^13A , R ^11A and R ^21A , R ^21A and R ^22A , R ^22A and R ^23A , and R ^23A and R ^24A are bonded to each other together with the atoms to which they are bonded. A ring may be formed.
Ring L ^1A represents a triazole ring or an imidazole ring composed of a nitrogen atom, E ¹ , E ^11A , E ^12A and E ^13A .
Ring L ^2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21A , E ^22A , E ^23A and E ^24A .
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ]

[Where:
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹ represents an integer of ¹ to 3, n ² represents an integer of 0 to 2, and n ¹ + n ² represents 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹ + n ² is 3, and when M is a palladium atom or platinum atom, n ¹ + n ² is 2.
^E11B , ^E12B , ^E13B , ^E14B , ^E21B , ^E22B , ^E23B and ^E24B each independently represent a nitrogen atom or a carbon atom. When there are a plurality of E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B , they may be the same or different. When E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B are nitrogen atoms, R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is not present.
R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a halogen atom or a substituted amino group is represented, and these groups may have a substituent. When there are a plurality of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B , they may be the same or different. R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , R ^11B and R ^21B , R ^21B and R ^22B , R ^22B and R ^23B , and R ^23B and R ^24B are combined, You may form the ring with the atom to which each couple | bonds.
Ring L ^1B represents a pyridine ring or a pyrimidine ring composed of a nitrogen atom, a carbon atom, E ^11B , E ^12B , E ^13B and E ^14B .
Ring L ^2B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21B , E ^22B , E ^23B and E ^24B .
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ] A polymer compound having a phosphorescent structural unit and a crosslinking group,
For each monomer unit constituting the polymer compound, a value x obtained by multiplying the molar ratio C of the monomer unit to the total mole of all monomer units and the molecular weight M of the monomer unit, and When a value y obtained by multiplying the molar ratio C by the number n of the cross-linking groups of the monomer unit is obtained, it is calculated from the sum X _{1 of} x and the sum Y _{1 of} y (Y ₁ × 1000) / X ₁ is a polymer compound having a value of 0.6 or more.