JP2015174931A - Polymeric compound and light-emitting element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymeric compound that is useful for the production of a light-emitting element excellent in a luminance life.SOLUTION: The polymeric compound comprises: a phosphorescent structural unit (B) having a structure of a phosphorescent compound (B) showing a maximum peak wavelength of 400 nm or more and less than 480 nm in an emission spectrum; and a phosphorescent structural unit (G) having a structure of a phosphorescent compound (G) showing a maximum peak wavelength of 480 nm or more and less than 680 nm in an emission spectrum. At least one structural unit selected from the group consisting of the phosphorescent structural unit (B) and the phosphorescent structural unit (G) is a phosphorescent structural unit having a dendron.

Description

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

  A light emitting element such as an organic electroluminescence element (organic EL element) can be suitably used for applications such as a display due to characteristics such as high luminous efficiency and low voltage driving, and has attracted attention in recent years. As materials used for the light-emitting layer of the light-emitting element, for example, phosphorescent compounds (B1), phosphorescent compounds (G1), and phosphorescent compounds (G2) represented below are described. There has been proposed a polymer compound containing two or more phosphorescent structural units having a structure of a conductive compound (Patent Document 1). Note that the phosphorescent compound (B1), the phosphorescent compound (G1), and the phosphorescent compound (G2) are phosphorescent compounds having no dendron.

JP 2003-342325 A

  However, the luminance life of a light emitting device manufactured using the above polymer compound is not always sufficient.

  Then, an object of this invention is to provide a high molecular compound useful for manufacture of the light emitting element which is excellent in a luminance lifetime. Another object of the present invention is to provide a light-emitting device obtained using the polymer compound.

  In the present invention, first, a phosphorescent constituent unit (B) having a structure of a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm, and a maximum peak wavelength of an emission spectrum of 480 nm. A phosphorescent structural unit (G) having a phosphorescent compound (G) structure of less than 680 nm, wherein the phosphorescent structural unit (B) and / or the phosphorescent structural unit (G) is a dendron. Provided is a polymer compound which is a phosphorescent constituent unit having

  Secondly, the present invention provides at least one selected from the group consisting of the above-described 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. And a composition containing the following materials.

  Thirdly, the present invention provides a light emitting device using the above polymer compound.

  ADVANTAGE OF THE INVENTION According to this invention, the high molecular compound useful for manufacture of the light emitting element which is excellent in a luminance lifetime can be provided. Moreover, according to this invention, the light emitting element obtained using this high molecular compound can be provided.

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

<Explanation of common terms>
Hereinafter, terms commonly used in the present 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.

  In the present specification, the hydrogen atom may be a deuterium atom or a light hydrogen atom.

  In this specification, a solid line representing a bond with a central metal in a structural formula representing a phosphorescent compound 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 . The structural unit contained in the polymer compound is 100 mol% in total.

  The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or other embodiments.

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

“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.
The alkyl group may have a substituent, 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, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group, and these Examples include groups in which the hydrogen atom in the group is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc., for example, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorobutyl group, Fluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3,5-di-hexyl group Ruphenyl) propyl group and 6-ethyloxyhexyl group.
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.
The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, 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 a ring from an aromatic hydrocarbon. The carbon atom number of an aryl group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-20, More preferably, it is 6-10.
The aryl group may have a substituent, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups Are groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

The “alkoxy group” may be linear or branched. The number of carbon atoms of a linear alkoxy group is 1-40 normally without including the carbon 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.
The alkoxy group may have a substituent, for example, 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 hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, And a group substituted with a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
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.
The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

The number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 7 to 48, not including the number of carbon atoms of the substituent.
The aryloxy group may have a substituent, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.

“P-valent heterocyclic group” (p represents an integer of 1 or more) is a p-group of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, this is an atomic group obtained by removing p hydrogen atoms from an aromatic heterocyclic compound directly bonded to carbon atoms or heteroatoms constituting the ring. A “p-valent aromatic heterocyclic group” is preferable.
`` 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 of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidyl group, quinolyl group, isoquinolyl group, pyrimidinyl group, triazinyl group, and these And a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.

  “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 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.
The alkenyl group and the cycloalkenyl group may have a substituent, such as a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4- Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and a group in which these groups have a substituent.

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 6-30, preferably 6-20, not including the carbon atoms of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4- Examples include a pentynyl group, a 1-hexenyl group, a 5-hexynyl group, and a group in which these groups have a substituent.

The “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The carbon atom number of an arylene group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-30, More preferably, it is 6-18.
The arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formula (A-1) to formula (A-20) are preferable. The arylene group includes a group in which a plurality of these groups are bonded.

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

[Wherein, R and R ^a each independently represents 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 carbon atom to which each is bonded. ]

The number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20 and more preferably 4 to 15 without including the number of carbon atoms of the substituent.
The divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine, Divalent acridine, furan, thiophene, azole, diazole, and triazole include divalent groups obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring, and preferably Is a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

［式中、ＲおよびＲ^aは、前記と同じ意味を表す。］

[Wherein, 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 heat treatment, ultraviolet irradiation treatment, radical reaction, etc., and preferably has the formula (B-1), (B-2 ), (B-3), (B-4), (B-5), (B-6), (B-7), (B-8), (B-9), (B-10), A group represented by (B-11), (B-12), (B-13), (B-14), (B-15), (B-16) or (B-17).

［式中、これらの基は置換基を有していてもよい。］

[In the formula, these groups may have a substituent. ]

  “Substituent” means a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, amino group, substituted amino group, alkenyl group. Represents a cycloalkenyl group, an alkynyl group or a cycloalkynyl group. The substituent may be a bridging group or a dendron.

<Dendron>
“Dendron” is a group having a regular dendritic branch structure (dendrimer structure) having an atom or a ring as a branch point. Examples of the compound having a dendron as a partial structure (sometimes referred to as a dendrimer) include structures described in documents such as WO02 / 066733, JP-A-2003-231692, WO2003 / 079736, and WO2006 / 097717. .

  The dendron is preferably a group represented by the formula (D-A) or (D-B), and more preferably a group represented by the formula (D-A).

［式中、
ｍ^DA1、ｍ^DA2およびｍ^DA3は、それぞれ独立に、０以上の整数を表す。
Ｇ^DAは、窒素原子、芳香族炭化水素基または複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^DA1、Ａｒ^DA2およびＡｒ^DA3は、それぞれ独立に、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^DA1、Ａｒ^DA2およびＡｒ^DA3が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^DAは、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^DAは、同一でも異なっていてもよい。］

[Where:
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups 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.
^TDA 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. ]

［式中、
ｍ^DA1、ｍ^DA2、ｍ^DA3、ｍ^DA4、ｍ^DA5、ｍ^DA6およびｍ^DA7は、それぞれ独立に、０以上の整数を表す。
Ｇ^DAは、窒素原子、芳香族炭化水素基または複素環基を表し、これらの基は置換基を有していてもよい。複数あるＧ^DAは、同一でも異なっていてもよい。
Ａｒ^DA1、Ａｒ^DA2、Ａｒ^DA3、Ａｒ^DA4、Ａｒ^DA5、Ａｒ^DA6およびＡｒ^DA7は、それぞれ独立に、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^DA1、Ａｒ^DA2、Ａｒ^DA3、Ａｒ^DA4、Ａｒ^DA5、Ａｒ^DA6およびＡｒ^DA7が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^DAは、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^DAは、同一でも異なっていてもよい。］

[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.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and 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.
^TDA 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. ]

m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably 0 or 1, More preferably, it is 0.

m ^DA2 and m ^DA3 are preferably the same integer.

m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are preferably the same integer.

m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are more preferably the same integer, and m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are More preferably, they are the same integer.

^GDA is preferably a group formed by removing three hydrogen atoms directly bonded to a carbon atom or a nitrogen atom constituting a ring from a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring or a carbazole ring. This group may have a substituent.

As the substituent that ^GDA may have, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable.

G ^DA, the table more preferably formula (GDA-11) ~ a group represented by (GDA-16), more preferably formula (GDA-11), (GDA -14) or (GDA-15) Group.

［式中、
＊は、式(D-A)におけるＡｒ^DA1、式(D-B)におけるＡｒ^DA1、式(D-B)におけるＡｒ^DA2、または、式(D-B)におけるＡｒ^DA3との結合を表す。
＊＊は、式(D-A)におけるＡｒ^DA2、式(D-B)におけるＡｒ^DA2、式(D-B)におけるＡｒ^DA4、または、式(D-B)におけるＡｒ^DA6との結合を表す。
＊＊＊は、式(D-A)におけるＡｒ^DA3、式(D-B)におけるＡｒ^DA3、式(D-B)におけるＡｒ^DA5、または、式(D-B)におけるＡｒ^DA7との結合を表す。
Ｒ^DAは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^DAが複数ある場合、それらは同一でも異なっていてもよい。］

[Where:
* Is, Ar ^DA1 in the formula (DA), Ar ^DA1 in the formula (DB), Ar in formula (DB) ^DA2, or represents a bond between Ar ^DA3 in the formula (DB).
** is, Ar ^DA2 in the formula (DA), Ar ^DA2 in the formula (DB), or Ar ^DA4, in the formula (DB), represents a bond between Ar ^DA6 in the formula (DB).
*** is, Ar ^DA3 in the formula (DA), Ar ^DA3 in the formula (DB), or Ar ^DA5, in the formula (DB), represents a bond between Ar ^DA7 in formula (DB).
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 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 phenylene group, ^fluorenediyl group, carbazolediyl group, dibenzofuranyl group, pyridinediyl group, pyrimidinediyl group or triazinediyl A group, more preferably a phenylene group, a fluorenediyl group or a carbazolediyl group, and these groups optionally have a substituent.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 may preferably have an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. , An alkoxy group or a cycloalkoxy group, more preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are more preferably groups represented by the formulas (ArDA-1) to (ArDA-3).

［式中、
Ｒ^DAは前記と同じ意味を表す。
Ｒ^DBは、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^DBが複数ある場合、それらは同一でも異なっていてもよい。］

[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 may 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.

Ar ^DA2 and Ar ^DA3 are preferably the same.

Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably the same.

Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are more preferably the same, and Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are the same More preferably.

T ^DA is preferably a group represented by the formula (TDA-1) ~ (TDA -3), more preferably a group represented by the formula (TDA-1) or (TDA-3), further A group represented by the formula (TDA-1) is preferable.

［式中、Ｒ^DAおよびＲ^DBは前記と同じ意味を表す。］

[Wherein, R ^DA and R ^DB represent the same meaning as described above. ]

The plurality of ^TDA are preferably the same.

  The group represented by the formula (D-A) is preferably a group represented by the formulas (D-A1) to (D-A4).

［式中、
Ｒ^ＤＡは前記と同じ意味を表す。
Ｒ^p1、Ｒ^p2およびＲ^p3は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基またはハロゲン原子を表す。Ｒ^p1およびＲ^p2が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
ｎｐ１は、０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０または１を表す。複数あるｎｐ１は、同一でも異なっていてもよい。］

[Where:
R ^DA represents the same meaning as described above.
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. A plurality of np1 may be the same or different. ]

  The group represented by the formula (D-B) is preferably a group represented by the formulas (D-B1) to (D-B3).

［式中、
Ｒ^p1、Ｒ^p2およびＲ^p3は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基またはハロゲン原子を表す。Ｒ^p1およびＲ^p2が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
ｎｐ１は０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０または１を表す。ｎｐ１およびｎｐ２が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。］

[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.

  Examples of the dendron include groups represented by formulas (D-A-1) to (D-A-18) and (D-B-1) to (D-B-8).

［式中、＊、＊＊および＊＊＊は、前記と同じ意味を表す。］

[Wherein, *, ** and *** represent the same meaning as described above. ]

R ^p represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, and these groups may have a substituent, such as a methyl group, a tert-butyl group, an n-hexyl group, A 2-ethylhexyl group, a group represented by the formula (Rp-1) or a 2-ethylhexyloxy group is preferred, and a tert-butyl group or a group represented by the formula (Rp-1) is more preferred.

<Phosphorescent compound>
“Phosphorescent compound” means a compound that exhibits phosphorescence, and is preferably a metal complex that emits light from a triplet excited state. This metal complex that emits light from a triplet excited state has a central metal atom and a ligand.

  As the central metal atom, a metal atom having an atomic number of 40 or more and having a spin-orbit interaction in the complex and capable of causing an intersystem crossing between a singlet state and a triplet state is exemplified. Examples of the metal atom include a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, and a platinum atom.

  The ligand is a neutral or anionic monodentate ligand that forms at least one bond selected from the group consisting of a coordination bond and a covalent bond with the central metal atom, or neutral. Or an anionic polydentate ligand is illustrated. Examples of the bond between the central metal atom and the ligand include a metal-nitrogen bond, a metal-carbon bond, a metal-oxygen bond, a metal-phosphorus bond, a metal-sulfur bond, and a metal-halogen bond. The multidentate ligand usually means a bidentate to hexadentate ligand.

Phosphorescent compounds are available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source.
In addition to the methods described above, “Journal of American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of American Chemical Society, Vol. 106, 6647-6653 (1984)”. It can also be produced by known methods described in literatures such as 2011/024761, International Publication No. 2002/44189, and Japanese Patent Application Laid-Open No. 2006-188673.

The maximum peak wavelength of the emission spectrum of the phosphorescent compound is obtained by dissolving the phosphorescent compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, etc. to prepare a dilute solution (1 × 10 ⁻⁶ to 1 × 10 ^{− 3} about wt%), it can be evaluated by measuring at room temperature the PL spectra of rare-thin solution. Xylene is preferred as the organic solvent for dissolving the phosphorescent compound.

<Phosphorescent Structural Unit (B)>
The phosphorescent structural unit (B) contained in the polymer compound of the present invention means a structural unit having the structure of the phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm.

  The phosphorescent compound (B) is not particularly limited as long as the maximum peak wavelength of the emission spectrum is 400 nm or more and less than 480 nm. However, the phosphorescent compound (B) is a phosphorescent compound represented by the formula (BM). preferable.

［式中、
Ｍは、ルテニウム原子、ロジウム原子、パラジウム原子、イリジウム原子または白金原子を表す。
ｎ^１Ｂは１以上の整数を表す。ｎ^２Ｂは０以上の整数を表す。但し、ｎ^１Ｂ＋ｎ^２Ｂは２または３である。Ｍがルテニウム原子、ロジウム原子またはイリジウム原子の場合、ｎ^１Ｂ＋ｎ^２Ｂは３であり、Ｍがパラジウム原子または白金原子の場合、ｎ^１Ｂ＋ｎ^２Ｂは２である。
Ｅ^１およびＥ^２は、それぞれ独立に、炭素原子または窒素原子を表す。Ｅ^１およびＥ^２が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。但し、Ｅ^１およびＥ^２の少なくとも一方は炭素原子である。
環Ｒ^１Ｂは、５員環または６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｒ^１Ｂが複数存在する場合、それらは同一でも異なっていてもよい。但し、環Ｒ^１Ｂが６員環の芳香族複素環である場合、Ｅ^１は炭素原子である。
環Ｒ^２Ｂは、５員環もしくは６員環の芳香族炭化水素環、または、５員環もしくは６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｒ^２Ｂが複数存在する場合、それらは同一でも異なっていてもよい。但し、環Ｒ^２Ｂが６員環の芳香族複素環である場合、Ｅ^２は炭素原子である。
但し、環Ｒ^１Ｂが６員環の芳香族複素環である場合、環Ｒ^２Ｂは電子求引基を有する。
Ａ^１−Ｇ^１−Ａ^２は、アニオン性の２座配位子を表し、Ｇ^１は、Ａ^１およびＡ^２とともに２座配位子を構成する原子団を表す。Ａ^１およびＡ^２は、それぞれ独立に、炭素原子、酸素原子または窒素原子を表し、これらの原子は環を構成する原子であってもよい。Ａ^１−Ｇ^１−Ａ^２が複数存在する場合、それらは同一でも異なっていてもよい。］

[Where:
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ^1B represents an integer of 1 or more. n ^2B represents an integer of 0 or more. However, n ^1B + n ^2B is 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ^1B + n ^2B is 3, and when M is a palladium atom or platinum atom, n ^1B + n ^2B is 2.
E ¹ and E ² each independently represents a carbon atom or a nitrogen atom. When a plurality of E ¹ and E ² are present, they may be the same or different. However, at least one of E ¹ and E ² is a carbon atom.
Ring R ^1B represents a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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 ^1B are present, they may be the same or different. However, when ring R ^1B is a 6-membered aromatic heterocycle, E ¹ is a carbon atom.
Ring R ^2B represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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 ^2B are present, they may be the same or different. However, when the ring R ^2B is a 6-membered aromatic heterocyclic ring, E ² is a carbon atom.
However, when the ring R ^1B is a 6-membered aromatic heterocyclic ring, the ring R ^2B has an electron withdrawing group.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand, and G ¹ represents an atomic group constituting a bidentate ligand together with A ¹ and A ² . 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. When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ]

  M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom.

When M is a ruthenium atom, a rhodium atom, or an iridium atom, n ^2B is preferably 0 or 1, and more preferably 0.

In the case where M is a palladium atom or a platinum atom, n ^2B is preferably 0.

E ¹ and E ² are preferably carbon atoms.

Ring R ^1B is preferably a 5-membered or 6-membered aromatic heterocycle having 1 to 4 nitrogen atoms as constituent atoms, and preferably has 2 to 3 nitrogen atoms as constituent atoms. It is more preferably a 5-membered aromatic heterocyclic ring or a 6-membered aromatic heterocyclic ring having 1 or more and 2 or less nitrogen atoms as constituent atoms, and a pyridine ring, pyrimidine ring, imidazole ring, pyrazole ring Or it is more preferable that it is a triazole ring, and it is especially preferable that it is an imidazole ring or a triazole ring, and these rings may have a substituent.

Ring R ^2B is preferably a 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, such as a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, It is more preferably a diazabenzene ring, pyrrole ring, furan ring or thiophene ring, more preferably a benzene ring, naphthalene ring, fluorene ring, pyridine ring or pyrimidine ring, and a benzene ring, pyridine ring or pyrimidine ring. Is particularly preferable, and a benzene ring is particularly preferable, and these rings may have a substituent.

When the ring R ^1B is a 6-membered aromatic heterocyclic ring, the number of electron withdrawing groups that the ring R ^2B has is usually 1 or more and 10 or less, and the phosphorescent property represented by the formula (BM) Since the synthesis of the compound is easy, it is preferably 2 or more and 5 or less, more preferably 2 or 3.

Examples of the “electron withdrawing group” include a group represented by —C (═X ¹¹ ) —R ¹¹ , a halogen atom, an alkyl group having a halogen atom as a substituent, and a cycloalkyl group having a halogen atom as a substituent. , A cyano group and a nitro group, preferably a fluorine atom, an alkyl group having a fluorine atom as a substituent, a cycloalkyl group having a fluorine atom as a substituent, or a cyano group, more preferably a fluorine atom, fluorine An alkyl group having an atom as a substituent or a cycloalkyl group having a fluorine atom as a substituent.

R ¹¹ represents 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 substituted amino group, and these groups have a substituent. It may be.

X ¹¹ represents a group represented by ═N—R ¹² , an oxygen atom or a sulfur atom, and is preferably an oxygen atom.

R ¹² represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. The group may have a substituent.

Definitions and examples of the substituents that R ¹¹ and R ¹² may have are the same as the definitions and examples of the substituents that the ring R ^1B and ring R ^2B described later may have.

The “alkyl group having a halogen atom as a substituent” means a group in which at least one hydrogen atom is substituted with a halogen atom among hydrogen atoms of the alkyl group. Further, the “cycloalkyl group having a halogen atom as a substituent” means a group in which at least one hydrogen atom is substituted with a halogen atom among hydrogen atoms of the cycloalkyl group. The halogen atom is preferably a fluorine atom.
Examples of the alkyl group having a fluorine atom include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, and a perfluorooctyl group, and a trifluoromethyl group is preferable.

The substituent that the ring R ^1B and the ring R ^2B may have is preferably 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. 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 further preferable, and an alkyl group, an aryl group or a dendron is particularly preferable. These groups may further have a substituent. When there are a plurality of substituents that the ring R ^1B and the ring R ^2B may have, 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.

Examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² include the ligands represented by the following.

［式中、＊は、Ｍと結合する部位を示す。］

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

When the phosphorescent compound (B) is a phosphorescent compound (DB) having a dendron, the phosphorescent compound (DB) is one or more phosphorescent compounds represented by the formula (BM). It is preferable that the phosphorescent compound has a dendron, and in Formula (BM), at least one ring selected from the group consisting of ring R ^1B and ring R ^2B is more preferably a phosphorescent compound having a dendron. preferable.

"At least one ring has a dendron" means that, among a plurality of rings, at least one of the hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the ring is substituted with a dendron. Means that. For example, in Formula (BM), when there are a plurality of rings R ^1B and rings R ^2B (that is, n ^1B is 2 or 3), among a plurality of rings R ^1B and a plurality of rings R ^2B , It is sufficient that at least one ring has a dendron.

Of the rings R ^1B and R ^2B , the number of dendrons in at least one ring is usually 1 or more and 5 or less, and it is easy to synthesize a phosphorescent compound. Or less, more preferably 1 or 2, and even more preferably 1.

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

When the dendron of at least one of the ring R ^1B and the ring R ^2B is a group represented by the formula (DA) or (DB) and m ^DA1 is 0, the ring R ^1B and / or or ^{G DA} of bonding to the ring ^{R 2B} is, it is preferably a group represented by the formula (GDA-11) or formula (GDA-12), a group represented by the formula (GDA-11) More preferred.

Of the rings R ^1B and R ^2B, the dendron possessed by at least one ring is preferably a group represented by the formula (D-A1), (D-A4) or (D-B1) A group represented by (D-A1) is more preferable.

  When M is a ruthenium atom, a rhodium atom or an iridium atom, the number of dendrons contained in the phosphorescent compound represented by the formula (BM) is usually 1 or more and 15 or less, and is represented by the formula (BM). Since it is easy to synthesize a phosphorescent compound, the number is preferably 1 or more and 9 or less, more preferably 2 or more and 6 or less.

  When M is a palladium atom or a platinum atom, the number of dendrons contained in the phosphorescent compound represented by the formula (BM) is usually from 1 to 9, and the phosphorescent property represented by the formula (BM). Since synthesis of the compound is easy, it is preferably 1 or more and 6 or less, more preferably 2 or more and 4 or less.

In the formula (BM), at least one of the ligands (ligands represented by ring R ^1B -ring R ^2B ) whose number is defined by the subscript n ^1B is represented by the formula (BM-L1) to A ligand represented by (BM-L3) is preferred, a ligand represented by formula (BM-L2) or (BM-L3) is more preferred, and a formula (BM-L2). It is more preferable that it is a ligand represented by.

［式中、
＊は前記と同じ意味を表す。
Ｘ^Ｂ１は、＝Ｃ（Ｒ^Ｂ４）−または＝Ｎ−を表す。
Ｒ^Ｂ１〜Ｒ^Ｂ８は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、デンドロンまたは電子求引基を表し、これらの基は置換基を有していてもよい。
但し、Ｒ^Ｂ５〜Ｒ^Ｂ８の少なくとも１つは電子求引基である。
Ｒ^Ｂ１とＲ^Ｂ２、Ｒ^Ｂ２とＲ^Ｂ３、Ｒ^Ｂ３とＲ^Ｂ４、Ｒ^Ｂ４とＲ^Ｂ５、Ｒ^Ｂ５とＲ^Ｂ６、Ｒ^Ｂ６とＲ^Ｂ７、および、Ｒ^Ｂ７とＲ^Ｂ８は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
X ^B1 represents ═C (R ^B4 ) — or ^═N— .
R ^{B1 to} R ^B8 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, a dendron, or an electron withdrawing group. These groups may have a substituent.
However, at least one of R ^{B5 to} R ^B8 is an electron withdrawing group.
R ^B1 and R ^B2 , R ^B2 and R ^B3 , R ^B3 and R ^B4 , R ^B4 and R ^B5 , R ^B5 and R ^B6 , R ^B6 and R ^B7 , and R ^B7 and R ^B8 are bonded to each other, You may form the ring with the atom to which each couple | bonds. ]

X ^B1 is preferably ═C (R ^B4 ) —.

R ^B1 , R ^B4 and R ^B8 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 More preferably, it is more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

R ^B2 , R ^B3 and R ^B6 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, an alkoxy group, or a dendron is more preferable, and a hydrogen atom, an alkyl group, an aryl group, or a dendron is further preferable, and these groups may have a substituent.

R ^B5 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, a dendron, or an electron withdrawing group, and a hydrogen atom, an alkyl group, an aryl group More preferably a hydrogen atom, an alkyl group or an electron withdrawing group, and particularly preferably a hydrogen atom or an electron withdrawing group. May have a substituent.

R ^B7 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, a dendron or an electron withdrawing group, and a hydrogen atom, an alkyl group, an aryl group More preferably a hydrogen atom, an alkyl group, an aryl group, a dendron or an electron withdrawing group, and a hydrogen atom, a dendron or an electron withdrawing group. It is particularly preferred that these groups may have a substituent.

Since the phosphorescent compound represented by the formula (BM) has excellent solubility in an organic solvent, at least one of R ^{B1 to} R ^B8 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 at least one of R ^B2 , R ^B3 , R ^B6 and R ^B7 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group More preferably a cycloalkoxy group, an aryloxy group or a dendron, and these groups optionally have a substituent.

When the ligand represented by the formula (BM-L1) has a dendron, it is preferable that at least one of R ^B2 , R ^B3 , R ^B6, and R ^B7 is a dendron, and at least one of R ^B6 and R ^B7 is A dendron is more preferable, and R ^B6 is further preferably a dendron.

When the ligand represented by the formula (BM-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 ^B2 , R ^B3 , R ^B5 and R ^B6 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 ^B2 and R ^B6 It is more preferable that 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.

Preferably, at least one of R ^B5 and ^{R B7} is a electron withdrawing ^group, more preferably ^{R B5} and ^{R B7} is an electron withdrawing group.

In the formula (BM), when a plurality of ligands represented by the formula (BM-L1) are present, the plurality of R ^{B1 to} R ^B8 may be the same or different.

［式中、
＊は前記と同じ意味を表す。
Ｘ^Ｂ２は、＝Ｃ（Ｒ^Ｂ１０）−または＝Ｎ−を表す。
Ｒ^Ｂ９〜Ｒ^Ｂ１５は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、デンドロンまたは電子求引基を表し、これらの基は置換基を有していてもよい。
Ｒ^Ｂ９とＲ^Ｂ１０、Ｒ^Ｂ１０とＲ^Ｂ１１、Ｒ^Ｂ９とＲ^Ｂ１２、Ｒ^Ｂ１２とＲ^Ｂ１３、Ｒ^Ｂ１３とＲ^Ｂ１４、および、Ｒ^Ｂ１４とＲ^Ｂ１５は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
X ^B2 represents ═C (R ^B10 ) — or ^═N— .
R ^{B9 to} R ^B15 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, a dendron, or an electron withdrawing group. These groups may have a substituent.
R ^B9 and R ^B10 , R ^B10 and R ^B11 , R ^B9 and R ^B12 , R ^B12 and R ^B13 , R ^B13 and R ^B14 , and R ^B14 and R ^B15 are bonded to each other and together with the atoms to which they are bonded A ring may be formed. ]

X ^B2 is preferably ═N—.

R ^B9 is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a dendron, since the luminance lifetime of the light-emitting element obtained using the polymer compound of the present invention is more excellent. A group, an aryl group, or a dendron is more preferable, an alkyl group or an aryl group is further preferable, and an alkyl group is particularly preferable. These groups may have a substituent.

R ^B10 and R ^B11 are 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 preferably a hydrogen atom, an alkyl group or an aryl group. Are more preferable, and a hydrogen atom or an alkyl group is more preferable, and these groups may have a substituent.

R ^B12 and R ^B15 are 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 preferably a hydrogen atom, an alkyl group or an aryl group. Are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

R ^B13 and R ^B14 are 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 an alkoxy group or a dendron, and further preferably a hydrogen atom, an alkyl group, an aryl group or a dendron, and these groups may have a substituent.

Since the phosphorescent compound represented by the formula (BM) has excellent solubility in an organic solvent, at least one of R ^{B9 to} R ^B15 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 at least one of R ^B9 , R ^B11 , R ^B13 and R ^B14 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group More preferably a cycloalkoxy group, an aryloxy group or a dendron, and these groups optionally have a substituent.

When the ligand represented by the formula (BM-L2) has a dendron, it is preferable that at least one of R ^B9 , R ^B13 and R ^B14 is a dendron, and at least one of R ^B9 and R ^B13 is a dendron. It is more preferable that R ^B13 is a dendron.

When the ligand represented by the formula (BM-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 ^B9 , R ^B11 , R ^B13 and R ^B14 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 R ^B9 , R ^B11 and R ^More preferably, at least one of ^B13 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 at least one of R ^B9 and R ^B11 is an alkyl group , Cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloal More preferably alkoxy is a group or an aryloxy group, these groups may have a substituent.

In the formula (BM), when a plurality of ligands represented by the formula (BM-L2) are present, the plurality of R ^{B9 to} R ^B15 may be the same or different.

［式中、
＊は前記と同じ意味を表す。
Ｘ^Ｂ３は、＝Ｃ（Ｒ^Ｂ１６）−または＝Ｎ−を表す。
Ｒ^Ｂ１６〜Ｒ^Ｂ２２は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、デンドロンまたは電子求引基を表し、これらの基は置換基を有していてもよい。
Ｒ^Ｂ１６とＲ^Ｂ１７、Ｒ^Ｂ１７とＲ^Ｂ１８、Ｒ^Ｂ１６とＲ^Ｂ１９、Ｒ^Ｂ１９とＲ^Ｂ２０、Ｒ^Ｂ２０とＲ^Ｂ２１、および、Ｒ^Ｂ２１とＲ^Ｂ２２は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
X ^B3 represents = C (R ^B16 ) ^-or = N-.
R ^{B16 to} R ^B22 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, a dendron, or an electron withdrawing group. These groups may have a substituent.
R ^B16 and R ^B17 , R ^B17 and R ^B18 , R ^B16 and R ^B19 , R ^B19 and R ^B20 , R ^B20 and R ^B21 , and R ^B21 and R ^B22 are bonded to each other together with the atoms to which they are bonded. A ring may be formed. ]

X ^B3 is preferably ═N—.

R ^B17 is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a dendron because the luminance life of a light-emitting element obtained using the polymer compound of the present invention is more excellent. A group, an aryl group, or a dendron is more preferable, an alkyl group or an aryl group is further preferable, and an alkyl group is particularly preferable. These groups may have a substituent.

R ^B16 and R ^B18 are 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 preferably a hydrogen atom, an alkyl group or an aryl group. Are more preferable, and a hydrogen atom or an alkyl group is more preferable, and these groups may have a substituent.

R ^B19 and R ^B22 are 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 preferably a hydrogen atom, an alkyl group or an aryl group. Are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

R ^B20 and R ^B21 are 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 an alkoxy group or a dendron, and further preferably a hydrogen atom, an alkyl group, an aryl group or a dendron, and these groups may have a substituent.

Since the phosphorescent compound represented by the formula (BM) has excellent solubility in an organic solvent, at least one of R ^{B16 to} R ^B22 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 at least one of R ^B17 , R ^B18 , R ^B20 and R ^B21 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group More preferably a cycloalkoxy group, an aryloxy group or a dendron, and these groups optionally have a substituent.

When the ligand represented by the formula (BM-L3) has a dendron, it is preferable that at least one of R ^B17 , R ^B20 and R ^B21 is a dendron, and at least one of R ^B17 and R ^B20 is a dendron. It is more preferable that R ^B20 is a dendron.

When the ligand represented by the formula (BM-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 ^B17 , R ^B18 , R ^B20 and R ^B21 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 R ^B17 , R ^B18 and R ^More preferably, at least one of ^B20 is an alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group or aryloxy group, and at least one of R ^B17 and R ^B18 is an alkyl group Cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, More preferably an alkoxy group or an aryloxy group, R ^B17 is an alkyl group, a cycloalkyl group, an aryl group, particularly preferably a monovalent heterocyclic group, an alkoxy group, cycloalkoxy group, or an aryloxy group, These groups may have a substituent.

In Formula (BM), when there are a plurality of ligands represented by Formula (BM-L3), the plurality of R ^{B16 to} R ^B22 may be the same or different.

  The phosphorescent structural unit (B) is a structural unit having the structure of the phosphorescent compound (B) having a maximum peak wavelength of the emission spectrum of 400 nm or more and less than 480 nm (that is, carbon constituting the phosphorescent compound (B)). A structural unit having a group excluding one or more hydrogen atoms directly bonded to an atom or a heteroatom), preferably a carbon atom or a heteroatom constituting the compound from the phosphorescent compound (B) A structural unit having a group formed by removing 1 or more and 3 or less hydrogen atoms directly bonded to, more preferably a structure represented by the formula (1B), (2B), (3B) or (4B) A unit, more preferably a structural unit represented by the formula (2B) or (3B), particularly preferably a structural unit represented by the formula (2B).

  <Structural Unit Represented by Formula (1B)>

［式中、
Ｍ^１Ｂは、発光スペクトルの最大ピーク波長が４００ｎｍ以上４８０ｎｍ未満である燐光発光性化合物（Ｂ）から、該化合物を構成する炭素原子またはヘテロ原子に直接結合する１個の水素原子を取り除いてなる基を表す。
Ｌ^１は、酸素原子、硫黄原子、−Ｎ（Ｒ^Ａ）−、−Ｃ（Ｒ^Ｂ）_２−、−Ｃ（Ｒ^Ｂ）＝Ｃ（Ｒ^Ｂ）−、−Ｃ≡Ｃ−、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Ａは、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Ｂは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｂは、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。Ｌ^１が複数存在する場合、それらは同一でも異なっていてもよい。
ｎ^ａ１は０以上の整数を表す。］

[Where:
M ^1B is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. Represents.
L ¹ represents an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C≡C—, an arylene group or It represents a divalent heterocyclic group, and these groups may 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, and a hydrogen atom or an alkyl group. Is more preferable, and a hydrogen atom is particularly preferable, and these groups may have a substituent.

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

Definitions and examples of the substituent that R ^A , R ^B, and L ¹ may have are the same as the definitions and examples of the substituent that the ring R ^1B and R ^2B may have.

n ^a1 is 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. .

  When the polymer compound of the present invention includes a structural unit represented by the formula (1B), the structural unit represented by the formula (1B) 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 ^1B is preferably 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 represented by the formula (BM). A group represented by BM-1) is more preferable.

［式中、
Ｍ、Ｅ^１、Ｅ^２、環Ｒ^１Ｂ、環Ｒ^２ＢおよびＡ^１−Ｇ^１−Ａ^２は、前記と同じ意味を表す。
環Ｒ^１Ｂ１は、５員環または６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、環Ｒ^１Ｂ１が６員環の芳香族複素環である場合、Ｅ^１は炭素原子である。
環Ｒ^２Ｂ１は、５員環もしくは６員環の芳香族炭化水素環、または、５員環もしくは６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、環Ｒ^２Ｂ１が６員環の芳香族複素環である場合、Ｅ^２は炭素原子である。
但し、環Ｒ^１Ｂ１が６員環の芳香族複素環である場合、環Ｒ^２Ｂ１は電子求引基を有する。
また、環Ｒ^１Ｂ１および環Ｒ^２Ｂ１の一方は、１つの結合手を有する。
ｎ^１およびｎ^２は、それぞれ独立に、０以上の整数を表す。但し、ｎ^１＋ｎ^２は１または２である。Ｍがルテニウム原子、ロジウム原子またはイリジウム原子の場合、ｎ^１＋ｎ^２は２であり、Ｍがパラジウム原子または白金原子の場合、ｎ^１＋ｎ^２は１である。］

[Where:
M, E ¹ , E ² , ring R ^1B , ring R ^2B and A ¹ -G ¹ -A ² represent the same meaning as described above.
Ring R ^1B1 represents a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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, when ring R ^1B1 is a 6-membered aromatic heterocyclic ring, E ¹ is a carbon atom.
Ring R ^2B1 represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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, when the ring R ^2B1 is a 6-membered aromatic heterocyclic ring, E ² is a carbon atom.
However, when the ring R ^1B1 is a 6-membered aromatic heterocyclic ring, the ring R ^2B1 has an electron withdrawing group.
One of the ring R ^1B1 and the ring R ^2B1 has one bond.
n ¹ and n ² each independently represents an integer of 0 or more. However, n ¹ + n ² is 1 or 2. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹ + n ² is 2, and when M is a palladium atom or a platinum atom, n ¹ + n ² is 1. ]

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

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

When ring R ^1B1 has no bond, the definition and examples of ring R ^1B1 are the same as the definition and examples of ring R ^1B described above.

When ring R ^1B1 has a bond, the definition and examples of the ring portion excluding the bond of ring R ^1B1 are the same as the definition and example of ring R ^1B described above.

When ring R ^2B1 does not have a bond, the definition and example of ring R ^2B1 are the same as the definition and example of ring R ^2B described above.

When ring R ^2B1 has a bond, the definition and examples of the ring portion excluding the bond of ring R ^2B1 are the same as the definition and example of ring R ^2B described above.

When the ligand represented by ring R ^{1B1 -ring} R ^2B1 is formula (BM-L1), R ^B2 , R ^B3 , R ^B6 or R ^B7 is preferably a bond, and R ^B2 , R ^B3 Alternatively, R ^B6 is more preferably a bond, R ^B2 or R ^B6 is more preferably a bond, and R ^B6 is particularly preferably a bond.

When the ligand represented by ring R ^{1B1 -ring} R ^2B1 is the formula (BM-L2), R ^B9 , R ^B13 or R ^B14 is preferably a bond, and R ^B9 or R ^B13 is a bond. It is more preferable that R ^B13 is a bond.

When the ligand represented by ring R ^{1B1 -ring} R ^2B1 is the formula (BM-L3), R ^B17 , R ^B20 or R ^B21 is preferably a bond, and R ^B17 or R ^B20 is a bond. It is more preferable that ^RB20 is a bond.

  <Structural Unit Represented by Formula (2B)>

［式中、
Ｍ^１Ｂは前記と同じ意味を表す。
Ｌ^２およびＬ^３は、それぞれ独立に、酸素原子、硫黄原子、−Ｎ（Ｒ^Ａ）−、−Ｃ（Ｒ^Ｂ）_２−、−Ｃ（Ｒ^Ｂ）＝Ｃ（Ｒ^Ｂ）−、−Ｃ≡Ｃ−、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^ＡおよびＲ^Ｂは、前記と同じ意味を表す。Ｌ^２およびＬ^３が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
ｎ^ｂ１およびｎ^ｃ１は、それぞれ独立に、０以上の整数を表す。複数存在するｎ^ｂ１は、同一でも異なっていてもよい。
Ａｒ^１Ｍは、芳香族炭化水素基または複素環基を表し、これらの基は置換基を有していてもよい。］

[Where:
M ^1B represents the same meaning as described above.
L ² and L ³ each independently represent an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C Represents ≡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 an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. ]

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

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

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, particularly preferably. 0.

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 the 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. A group excluding three hydrogen atoms directly bonded to the atom Are particularly preferred, and these groups may have a substituent.

Definitions and examples of the substituent that L ² , L ^3, and Ar ^1M may have are the same as the definitions and examples of the substituent that the above-described ring R ^1B and ring R ^2B may have.

  <Structural Unit Represented by Formula (3B)>

［式中、
Ｌ^２およびｎ^ｂ１は、前記と同じ意味を表す。
Ｍ^２Ｂは、発光スペクトルの最大ピーク波長が４００ｎｍ以上４８０ｎｍ未満である燐光発光性化合物（Ｂ）から、該化合物を構成する炭素原子またはヘテロ原子に直接結合する２個の水素原子を取り除いてなる基を表す。］

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^2B is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. Represents. ]

M ^2B is preferably a group formed by removing two hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the compound from the phosphorescent compound represented by the formula (BM). A group represented by BM-2) or (BM-3) is more preferred, and a group represented by formula (BM-2) is even more preferred.

［式中、
Ｍ、Ｅ^１、Ｅ^２、環Ｒ^１Ｂ、環Ｒ^２Ｂ、環Ｒ^１Ｂ１、環Ｒ^２Ｂ１およびＡ^１−Ｇ^１−Ａ^２は前記と同じ意味を表す。複数存在する環Ｒ^１Ｂ１は、同一でも異なっていてもよい。複数存在する環Ｒ^２Ｂ１は、同一でも異なっていてもよい。
ｎ^３およびｎ^４は、それぞれ独立に、０以上の整数を表す。但し、ｎ^３＋ｎ^４は０または１である。Ｍがルテニウム原子、ロジウム原子またはイリジウム原子の場合、ｎ^３＋ｎ^４は１であり、Ｍがパラジウム原子または白金原子の場合、ｎ^３＋ｎ^４は０である。］

[Where:
M, E ¹ , E ² , ring R ^1B , ring R ^2B , ring R ^1B1 , ring R ^2B1 and A ¹ -G ¹ -A ² represent the same meaning as described above. A plurality of rings R ^1B1 may be the same or different. A plurality of rings R ^2B1 may be the same or different.
n ³ and n ⁴ each independently represents an integer of 0 or more. However, n ³ + n ⁴ is 0 or 1. When M is a ruthenium atom, rhodium atom or iridium atom, n ³ + n ⁴ is 1, and when M is a palladium atom or platinum atom, n ³ + n ⁴ is 0. ]

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

［式中、
Ｍ、Ｅ^１、Ｅ^２、環Ｒ^１Ｂ、環Ｒ^２Ｂ、Ａ^１−Ｇ^１−Ａ^２、ｎ^１およびｎ^２は、前記と同じ意味を表す。
環Ｒ^１Ｂ２は、５員環または６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、環Ｒ^１Ｂ２が６員環の芳香族複素環である場合、Ｅ^１は炭素原子である。
環Ｒ^２Ｂ２は、５員環もしくは６員環の芳香族炭化水素環、または、５員環もしくは６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、環Ｒ^２Ｂ２が６員環の芳香族複素環である場合、Ｅ^２は炭素原子である。
但し、環Ｒ^１Ｂ２が６員環の芳香族複素環である場合、環Ｒ^２Ｂ２は電子求引基を有する。
また、環Ｒ^１Ｂ２および環Ｒ^２Ｂ２の一方は２つの結合手を有するか、または、環Ｒ^１Ｂ２および環Ｒ^２Ｂ２は、結合手を１つずつ有する。］

[Where:
M, E ¹ , E ² , ring R ^1B , ring R ^2B , A ¹ -G ¹ -A ² , n ¹ and n ² represent the same meaning as described above.
Ring R ^1B2 represents a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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, when ring R ^1B2 is a 6-membered aromatic heterocyclic ring, E ¹ is a carbon atom.
Ring R ^2B2 represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and these rings optionally have a substituent. When a plurality of such 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, when the ring R ^2B2 is a 6-membered aromatic heterocyclic ring, E ² is a carbon atom.
However, when the ring R ^1B2 is a 6-membered aromatic heterocyclic ring, the ring R ^2B2 has an electron withdrawing group.
One of the ring R ^1B2 and the ring R ^2B2 has two bonds, or the ring R ^1B2 and the ring R ^2B2 have one bond each. ]

When ring R ^1B2 has no bond, the definition and examples of ring R ^1B2 are the same as the definition and examples of ring R ^1B described above.

When ring R ^1B2 has a bond, the definition and examples of the ring portion excluding the bond of ring R ^1B2 are the same as the definition and example of ring R ^1B described above.

When ring R ^2B2 has no bond, the definition and examples of ring R ^2B2 are the same as the definition and examples of ring R ^2B described above.

When ring R ^2B2 has a bond, the definition and examples of the ring portion excluding the bond of ring R ^2B2 are the same as the definition and example of ring R ^2B described above.

Ring R ^1B2 and ring R ^2B2 preferably have one bond each.

When the ligand represented by the ring R ^{1B2 -ring} R ^2B2 is the formula (BM-L1), it is preferable that two of R ^B2 , R ^B3 , R ^B6 and R ^B7 are a bond, ^More preferably, ^B2 and R ^B6 , R ^B2 and R ^B7 , R ^B3 and R ^B6 , or R ^B3 and R ^B7 are a bond.

When the ligand represented by ring R ^{1B2 -ring} R ^2B2 is the formula (BM-L2), it is preferable that two of R ^B9 , R ^B13 and R ^B14 are a bond, and R ^B9 and R More preferably, ^B13 , or R ^B9 and R ^B14 are a bond.

When the ligand represented by ring R ^{1B2 -ring} R ^2B2 is the formula (BM-L3), two of R ^B17 , R ^B20 and R ^B21 are preferably a bond, and R ^B17 and R ^B More preferably, ^B20 , or R ^B17 and R ^B21 are a bond.

  <Structural Unit Represented by Formula (4B)>

［式中、
Ｌ^２およびｎ^ｂ１は、前記と同じ意味を表す。
Ｍ^３Ｂは、発光スペクトルの最大ピーク波長が４００ｎｍ以上４８０ｎｍ未満である燐光発光性化合物（Ｂ）から、該化合物を構成する炭素原子またはヘテロ原子に直接結合する３個の水素原子を取り除いてなる基を表す。］

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^3B is a group obtained by removing three hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. Represents. ]

M ^3B is preferably a group obtained by removing three hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the compound from the phosphorescent compound represented by the formula (BM). A group represented by BM-4) is preferred.

［式中、
Ｍ、Ｅ^１、Ｅ^２、環Ｒ^１Ｂ、環Ｒ^２Ｂ、環Ｒ^１Ｂ１、環Ｒ^２Ｂ１、環Ｒ^１Ｂ２および環Ｒ^２Ｂ２は前記と同じ意味を表す。
ｎ^５は０または１を表す。ｎ^６は１または３を表す。但し、Ｍがルテニウム原子、ロジウム原子またはイリジウム原子の場合、ｎ^５は０であり、且つ、ｎ^６は３である。Ｍがパラジウム原子または白金原子の場合、ｎ^５は１であり、且つ、ｎ^６は１である。］

[Where:
M, E ¹ , E ² , ring R ^1B , ring R ^2B , ring R ^1B1 , ring R ^2B1 , ring R ^1B2 and ring R ^2B2 represent the same meaning as described above.
n ⁵ represents 0 or 1. n ⁶ represents 1 or 3. However, when M is a ruthenium atom, a rhodium atom, or an iridium atom, n ⁵ is 0 and n ⁶ is 3. When M is a palladium atom or a platinum atom, n ⁵ is 1 and n ⁶ is 1. ]

  Examples of the phosphorescent structural unit (B) include structural units represented by formulas (B-1) to (B-17).

［式中、Ｄｅはデンドロンを表す。Ｄｅが複数存在する場合、それらは同一でも異なっていてもよい。］

[In the formula, De represents dendron. When a plurality of De are present, they may be the same or different. ]

<Phosphorescent Structural Unit (G)>
The phosphorescent structural unit (G) contained in the polymer compound of the present invention means a structural unit having a structure of the phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm.

  The phosphorescent compound (G) is not particularly limited as long as it has a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. However, the phosphorescent compound (G) is a phosphorescent compound represented by the formula (GM). preferable.

［式中、
ＭおよびＡ^１−Ｇ^１−Ａ^２は前記と同じ意味を表す。
ｎ^１Ｇは１以上の整数を表す。ｎ^２Ｇは０以上の整数を表す。但し、ｎ^１Ｇ＋ｎ^２Ｇは２または３である。Ｍがルテニウム原子、ロジウム原子またはイリジウム原子の場合、ｎ^１Ｇ＋ｎ^２Ｇは３であり、Ｍがパラジウム原子または白金原子の場合、ｎ^１Ｇ＋ｎ^２Ｇは２である。
Ｅ^４は、炭素原子または窒素原子を表す。Ｅ^４が複数存在する場合、それらは同一でも異なっていてもよい。
環Ｒ^１Ｇは、６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｒ^１Ｇが複数存在する場合、それらは同一でも異なっていてもよい。
環Ｒ^２Ｇは、５員環もしくは６員環の芳香族炭化水素環、または、５員環もしくは６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｒ^２Ｇが複数存在する場合、それらは同一でも異なっていてもよい。但し、環Ｒ^２Ｇが６員環の芳香族複素環である場合、Ｅ^４は炭素原子である。］

[Where:
M and A ¹ -G ¹ -A ² represent the same meaning as described above.
n ^1G represents an integer of 1 or more. n ^2G represents an integer of 0 or more. However, n ^1G + n ^2G is 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ^1G + n ^2G is 3, and when M is a palladium atom or platinum atom, n ^1G + n ^2G is 2.
E ⁴ represents a carbon atom or a nitrogen atom. When a plurality of E ⁴ are present, they may be the same or different.
Ring R ^1G represents a 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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 represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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. ]

When M is a ruthenium atom, rhodium atom or iridium atom, n ^2G is preferably 0 or 1, more preferably 0.

In the case where M is a palladium atom or a platinum atom, n ^2G is preferably 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 More preferred is a pyridine ring, a diazabenzene ring, a quinoline ring or an isoquinoline ring, and particularly preferred is a pyridine ring, a quinoline ring or an isoquinoline ring, and these rings have a substituent. You may do it.

Ring R ^2G is preferably a 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, such as a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, A diazabenzene 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, and these rings have a substituent. You may do it.

Definitions and examples of the substituent that the ring R ^1G and the ring R ^2G may have are the same as the definitions and examples of the substituent that the ring R ^1B and the ring R ^2B may have.

When the phosphorescent compound (G) is a phosphorescent compound (DG) having a dendron, the phosphorescent compound (DG) is one or more phosphorescent compounds represented by the formula (GM). It is preferable that the compound is a phosphorescent compound having a dendron, and in the formula (GM), at least one ring selected from the group consisting of ring R ^1G and ring R ^2G is a phosphorescent compound having a dendron. preferable.

Of the ring R ^1G and the ring R ^2G , the preferred range of the number of dendrons possessed by at least one ring is the same as the preferred range of the number of the dendrons possessed by at least one of the rings R ^1B and R ^2B. It is.

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

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

Among the rings R ^1B and R ^2B, 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), at least one of the ligands (ligands represented by ring R ^{1G -ring} R ^2G ) whose number is defined by the subscript n ^1G is represented by the formula (GM-L1) to A ligand represented by (GM-L4) is preferred, and a ligand represented by the formula (GM-L1) or (GM-L2) is more preferred.

［式中、
＊は前記と同じ意味を表す。
Ｒ^Ｇ１〜Ｒ^Ｇ８は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基またはデンドロンを表し、これらの基は置換基を有していてもよい。
Ｒ^Ｇ１とＲ^Ｇ２、Ｒ^Ｇ２とＲ^Ｇ３、Ｒ^Ｇ３とＲ^Ｇ４、Ｒ^Ｇ４とＲ^Ｇ５、Ｒ^Ｇ５とＲ^Ｇ６、Ｒ^Ｇ６とＲ^Ｇ７、および、Ｒ^Ｇ７とＲ^Ｇ８は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
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 to 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 further preferable, and a hydrogen atom is particularly preferable. 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, It is more preferably 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.

Since the phosphorescent compound represented by the formula (GM) has excellent solubility in an organic solvent, 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 at least one of R ^G2 , R ^G3 , R ^G6 and R ^G7 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group More preferably a cycloalkoxy group, an aryloxy group or a dendron, and these groups optionally have a substituent.

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 ^G5 and R ^G6 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 It is more preferable that 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), 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 from each other.

［式中、
＊は前記と同じ意味を表す。
Ｒ^Ｇ９〜Ｒ^Ｇ１８は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基またはデンドロンを表し、これらの基は置換基を有していてもよい。
Ｒ^Ｇ９とＲ^Ｇ１０、Ｒ^Ｇ１０とＲ^Ｇ１１、Ｒ^Ｇ１１とＲ^Ｇ１２、Ｒ^Ｇ１２とＲ^Ｇ１３、Ｒ^Ｇ１３とＲ^Ｇ１４、Ｒ^Ｇ１４とＲ^Ｇ１５、Ｒ^Ｇ１５とＲ^Ｇ１６、Ｒ^Ｇ１６とＲ^Ｇ１７、および、Ｒ^Ｇ１７とＲ^Ｇ１８は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
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 further preferable, and a hydrogen atom is particularly preferable. 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, and a hydrogen atom, an alkyl group, An aryl group, a monovalent heterocyclic group or a dendron is more preferable, a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a dendron is further preferable, and a hydrogen atom or a dendron is preferable. Particularly preferred, these groups may have a substituent.

Since the phosphorescent compound represented by the formula (GM) has excellent solubility in an organic solvent, 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 at least one of R ^G10 , R ^G16 and R ^G17 is an alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy More preferably, they are a group, an aryloxy group or a dendron, and these groups may have a substituent.

When the ligand represented by the formula (GM-L2) has a dendron, it is preferable that at least one of R ^G10 , R ^G16 and R ^G17 is a dendron, and at least one of R ^G16 and R ^G17 is a dendron. More preferably, R ^G16 is further 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, 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 ^G16 and R ^G17 is an alkyl group 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), when a plurality of ligands represented by Formula (GM-L2) are present, the plurality of R ^{G9 to} R ^G18 may be the same as or different from each other.

［式中、
＊は前記と同じ意味を表す。
Ｒ^Ｇ１９〜Ｒ^Ｇ２８は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基またはデンドロンを表し、これらの基は置換基を有していてもよい。
Ｒ^Ｇ１９とＲ^Ｇ２０、Ｒ^Ｇ２０とＲ^Ｇ２１、Ｒ^Ｇ２１とＲ^Ｇ２２、Ｒ^Ｇ２２とＲ^Ｇ２３、Ｒ^Ｇ２３とＲ^Ｇ２４、Ｒ^Ｇ２４とＲ^Ｇ２５、Ｒ^Ｇ２５とＲ^Ｇ２６、Ｒ^Ｇ２６とＲ^Ｇ２７、および、Ｒ^Ｇ２７とＲ^Ｇ２８は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
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, and these groups are 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 More preferably, it 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.

Since the phosphorescent compound represented by the formula (GM) has excellent solubility in an organic solvent, 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, wherein at least one of R ^G26 and R ^G27 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryl It is more preferable that they are an oxy group or a dendron, and these groups may have a substituent.

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

［式中、
＊は前記と同じ意味を表す。
Ｒ^Ｇ２９〜Ｒ^Ｇ３８は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基またはデンドロンを表し、これらの基は置換基を有していてもよい。
Ｒ^Ｇ２９とＲ^Ｇ３０、Ｒ^Ｇ３０とＲ^Ｇ３１、Ｒ^Ｇ３１とＲ^Ｇ３２、Ｒ^Ｇ３２とＲ^Ｇ３３、Ｒ^Ｇ３３とＲ^Ｇ３４、Ｒ^Ｇ３４とＲ^Ｇ３５、Ｒ^Ｇ３５とＲ^Ｇ３６、Ｒ^Ｇ３６とＲ^Ｇ３７、および、Ｒ^Ｇ３７とＲ^Ｇ３８は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Where:
* Represents the same meaning as described above.
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 ^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, an alkyl group or an aryl group More preferably, it is more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

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, 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.

Since the phosphorescent compound represented by the formula (GM) has excellent solubility in an organic solvent, at least one of R ^{G29 to} R ^G38 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or an alkoxy group. , A cycloalkoxy group, an aryloxy group or a dendron, and at least one of R ^G33 , R ^G36 and R ^G37 is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy More preferably, they are a group, an aryloxy group or a dendron, and these groups may have a substituent.

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 at least one of R ^G37 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 at least one of R ^G36 and R ^G37 is an alkyl group 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 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent complex. More preferably a cyclic group, an alkoxy group, a cycloalkoxy group or an aryloxy group. Good.

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

  The phosphorescent structural unit (G) is a structural unit having a structure of a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm (that is, carbon constituting the phosphorescent compound (G)). A structural unit having a group excluding one or more hydrogen atoms directly bonded to an atom or a hetero atom), preferably from a phosphorescent compound (G), a carbon atom or a hetero atom constituting the compound A structural unit having a group formed by removing 1 or more and 3 or less hydrogen atoms directly bonded to the structure, more preferably a structure represented by the formula (1G), (2G), (3G) or (4G) A unit, more preferably a structural unit represented by formula (1G), (2G) or (3G), particularly preferably a structural unit represented by formula (2G) or (3G). That.

  <Structural Unit Represented by Formula (1G)>

［式中、
Ｌ^１およびｎ^ａ１は、前記と同じ意味を表す。
Ｍ^１Ｇは、発光スペクトルの最大ピーク波長が４８０ｎｍ以上６８０ｎｍ未満である燐光発光性化合物（Ｇ）から、該化合物を構成する炭素原子またはヘテロ原子に直接結合する１個の水素原子を取り除いてなる基を表す。］

[Where:
L ¹ and ^na1 represent the same meaning as described above.
M ^1G is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. Represents. ]

  When the polymer compound of the present invention 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” has the same meaning as described above.

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

［式中、Ｍ、Ｅ^４、環Ｒ^１Ｇ、環Ｒ^２Ｇ、Ａ^１−Ｇ^１−Ａ^２、ｎ^１およびｎ^２は、前記と同じ意味を表す。
環Ｒ^１Ｇ１は、６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
環Ｒ^２Ｇ１は、５員環もしくは６員環の芳香族炭化水素環、または、５員環もしくは６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、環Ｒ^２Ｇ１が６員環の芳香族複素環である場合、Ｅ^４は炭素原子である。
また、環Ｒ^１Ｇ１および環Ｒ^２Ｇ１の一方は、１つの結合手を有する。］

[Wherein, M, E ⁴ , ring R ^1G , ring R ^2G , A ¹ -G ¹ -A ² , n ¹ and n ² represent the same meaning as described above.
Ring R ^1G1 represents a 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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 ^2G1 represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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, when the ring R ^2G1 is a 6-membered aromatic heterocyclic ring, E ⁴ is a carbon atom.
Further, one of the ring R ^1G1 and the ring R ^2G1 has one bond. ]

When ring R ^1G1 has no bond, the definition and examples of ring R ^1G1 are the same as the definition and examples of ring R ^1G described above.

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

When ring R ^2G1 does not have a bond, the definition and example of ring R ^2G1 are the same as the definition and example of ring R ^2G described above.

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

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

When the ligand represented by ring R ^{1G1 -ring} R ^2G1 is the formula (GM-L2), R ^G10 , R ^G16 or R ^G17 is preferably a bond, and ^RG16 is a bond. Is more preferable.

When the ligand represented by ring R ^{1G1 -ring} R ^2G1 is the formula (GM-L3), R ^G26 or R ^G27 is preferably a bond, and R ^G26 is more preferably a bond. .

Ring ^{R 1G1} - if ligand for ring ^{R 2G1} is an expression ^(GM-L4), it is preferable that ^{R G36} or ^{R G37} is a ^bond, and more preferably ^{R G36} is a bond .

  <Structural Unit Represented by Formula (2G)>

［式中、Ｍ^１Ｇ、Ｌ^２、Ｌ^３、ｎ^ｂ１、ｎ^ｃ１およびＡｒ^１Ｍは、前記と同じ意味を表す。］

[Wherein, M ^1G , L ² , L ³ , n ^b1 , n ^c1 and Ar ^1M represent the same meaning as described above. ]

  <Structural Unit Represented by Formula (3G)>

［式中、
Ｌ^２およびｎ^ｂ１は、前記と同じ意味を表す。
Ｍ^２Ｇは、発光スペクトルの最大ピーク波長が４８０ｎｍ以上６８０ｎｍ未満である燐光発光性化合物（Ｇ）から、該化合物を構成する炭素原子またはヘテロ原子に直接結合する２個の水素原子を取り除いてなる基を表す。］

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^2G is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. Represents. ]

M ^2G is preferably a group formed by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound represented by the formula (GM). A group represented by GM-2) or (GM-3) is more preferred, and a group represented by formula (GM-2) is even more preferred.

［式中、Ｍ、Ｅ^４、環Ｒ^１Ｇ、環Ｒ^２Ｇ、環Ｒ^１Ｇ１、環Ｒ^２Ｇ１、Ａ^１−Ｇ^１−Ａ^２、ｎ^３およびｎ^４は前記と同じ意味を表す。複数存在する環Ｒ^１Ｇ１は、同一でも異なっていてもよい。複数存在する環Ｒ^２Ｇ１は、同一でも異なっていてもよい。］

Wherein, M, ^{E 4,} ring ^{R 1G,} ring ^{R 2G,} ring ^{R 1G1,} ring ^{R 2G1, A 1 -G 1 -A} 2, n 3 and ^{n 4} are as defined above. Plural rings R ^1G1 may be the same or different. A plurality of rings R ^2G1 may be the same or different. ]

［式中、
Ｍ、Ｅ^４、環Ｒ^１Ｇ、環Ｒ^２Ｇ、Ａ^１−Ｇ^１−Ａ^２、ｎ^１およびｎ^２は、前記と同じ意味を表す。
環Ｒ^１Ｇ２は、６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
環Ｒ^２Ｇ２は、５員環もしくは６員環の芳香族炭化水素環、または、５員環もしくは６員環の芳香族複素環を表し、これらの環は置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。但し、環Ｒ^２Ｇ２が６員環の芳香族複素環である場合、Ｅ^４は炭素原子である。
また、環Ｒ^１Ｇ２および環Ｒ^２Ｇ２の一方は２つの結合手を有するか、または、環Ｒ^１Ｇ２および環Ｒ^２Ｇ２は、結合手を１つずつ有する。］

[Where:
M, E ⁴ , ring R ^1G , ring R ^2G , A ¹ -G ¹ -A ² , n ¹ and n ² represent the same meaning as described above.
Ring R ^1G2 represents a 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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 hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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, when the ring R ^2G2 is a 6-membered aromatic heterocyclic ring, E ⁴ is a carbon atom.
One of the ring R ^1G2 and the ring R ^2G2 has two bonds, or the ring R ^1G2 and the ring R ^2G2 have one bond each. ]

When ring R ^1G2 has no bond, the definition and examples of ring R ^1G2 are the same as the definition and examples of ring R ^1G described above.

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

When ring R ^2G2 has no bond, the definition and examples of ring R ^2G2 are the same as the definition and examples of ring R ^2G described above.

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

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

When the ligand represented by ring R ^{1G2 -ring} R ^2G2 is the formula (GM-L1), it is preferable that two of R ^G2 , R ^G3 , R ^G6 and R ^G7 are a bond, ^More preferably, ^G2 and R ^G6 , R ^G2 and R ^G7 , R ^G3 and R ^G6 , or R ^G3 and R ^G7 are a bond.

Ring ^{R 1G2} - if ligand for ring ^{R 2G2} is an expression ^{(GM-L2), R G10} , of ^{R G16} and ^{R G17,} preferably Two a ^{bond, R G10} and R More preferably, ^G16 or R ^G10 and R ^G17 are a bond.

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

Ring ^{R 1G2} - if ligand for ring ^{R 2G2} is an expression ^(GM-L4), among R ^{G36, R G37} and ^{R G33,} preferably Two a ^{bond, R G36} and R More preferably, ^G33 , or R ^G37 and R ^G33 are a bond.

  <Structural Unit Represented by Formula (4G)>

［式中、
Ｌ^２およびｎ^ｂ１は、前記と同じ意味を表す。
Ｍ^３Ｇは、発光スペクトルの最大ピーク波長が４８０ｎｍ以上６８０ｎｍ未満である燐光発光性化合物（Ｇ）から、該化合物を構成する炭素原子またはヘテロ原子に直接結合する３個の水素原子を取り除いてなる基を表す。］

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^3G is a group obtained by removing three hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. Represents. ]

M ^3G is preferably a group obtained by removing three hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from the phosphorescent compound represented by the formula (GM). A group represented by GM-4) is preferred.

［式中、Ｍ、Ｅ^４、環Ｒ^１Ｇ１、環Ｒ^２Ｇ１、環Ｒ^１Ｇ２、環Ｒ^２Ｇ２、Ａ^１−Ｇ^１−Ａ^２、ｎ^５およびｎ^６は前記と同じ意味を表す。］

[ ^Wherein , M, E ⁴ , ring R ^1G1 , ring R ^2G1 , ring R ^1G2 , ring R ^2G2 , A ¹ -G ¹ -A ² , n ⁵ and n ⁶ represent the same meaning as described above. ]

  Examples of the phosphorescent structural unit (G) include formulas (1G-1) to (1G-13), formulas (2G-1) to (2G-16), and formulas (3G-1) to (3G-). 23) and structural units represented by formulas (4G-1) to (4G-6).

［式中、ＤｅおよびＲ^ｐは、前記と同じ意味を表す。］

[Wherein, De and R ^p represent the same meaning as described above. ]

<Structural Unit Represented by Formula (Y)>
The polymer compound of the present invention preferably further contains a structural unit represented by the formula (Y).

［式中、Ａｒ^Y1は、アリーレン基、２価の複素環基、または、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。］

[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, and these This group may have a substituent. ]

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

The divalent heterocyclic group represented by Ar ^Y1 is more preferably a formula (AA-1) to a formula (AA-4), a formula (AA-10) to a formula (AA-15), a formula (AA- 18) to a group represented by formula (AA-21), formula (AA-33) or formula (AA-34), more preferably formula (AA-4), formula (AA-10), formula (AA) AA-12), a group represented by formula (AA-14) or formula (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 above-mentioned arylene group and divalent heterocyclic group represented by Ar ^Y1 .

  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.

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

[Wherein R ^XX 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 ^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 structural units represented by the formulas (Y-1) to (Y-10), and brightness of a light-emitting element using the polymer compound of the present invention. From the viewpoint of lifetime, it is preferably a structural unit represented by the formula (Y-1), (Y-2) or (Y-3), and from the viewpoint of electron transport properties, preferably the formula (Y-4 ) To (Y-7), and from the viewpoint of hole transport properties, the structural units are preferably represented by formulas (Y-8) to (Y-10).

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

[Wherein 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 optionally 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 ′).

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

[Wherein, 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 optionally 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.

［式中、Ｒ^Y1は前記と同じ意味を表す。Ｘ^Y1は、−Ｃ(Ｒ^Y2)₂−、−Ｃ(Ｒ^Y2)＝Ｃ(Ｒ^Y2)−またはＣ(Ｒ^Y2)₂−Ｃ(Ｒ^Y2)₂−で表される基を表す。Ｒ^Y2は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y2は、同一でも異なっていてもよく、Ｒ^Y2同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[Wherein, 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. May be.

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ₂ — is preferably an alkyl group or a cycloalkyl group, 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 formulas (Y-A1) to (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. It may be.

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 may have a substituent.

In X ^Y1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably 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 formulas (Y-B1) to (Y-B5), more preferably a group represented by formula (Y-B3), and these groups are substituted. It may have a group.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

[Wherein, 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 ′).

［式中、Ｒ^Y1およびＸ^Y1は前記と同じ意味を表す。］

[Wherein, R ^Y1 and X ^Y1 represent the same meaning as described above. ]

［式中、Ｒ^Y1およびＸ^Y1は前記と同じ意味を表す。］

[Wherein, 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 ′).

［式中、Ｒ^Y11およびＸ^Y1は前記と同じ意味を表す。］

[Wherein, R ^Y11 and X ^Y1 represent the same meaning as described above. ]

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

[Wherein, 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 -6 ′) is preferred.

［式中、Ｒ^Y1およびＲ^Y3は前記と同じ意味を表す。］

[Wherein, R ^Y1 and R ^Y3 represent the same meaning as described above. ]

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

[Wherein, 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.

  Examples of the structural unit represented by the formula (Y) include structural units composed of an arylene group represented by the formulas (Y-101) to (Y-121), and the formulas (Y-201) to (Y-206). A structural unit consisting of a divalent heterocyclic group represented by the formula: at least one arylene group represented by formulas (Y-301) to (Y-304) and at least one divalent heterocyclic group. Examples thereof include a structural unit composed of a divalent group directly bonded.

<Structural Unit Represented by Formula (X)>
The polymer compound of the present invention may further contain a structural unit represented by the following formula (X).

［式中、ａ^X1およびａ^X2は、それぞれ独立に、０以上の整数を表す。Ａｒ^X1およびＡｒ^X3は、それぞれ独立に、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2およびＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、または、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ｒ^X1、Ｒ^X2およびＲ^X3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[ ^Wherein , 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. 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 optionally have a substituent. ]

a ^X1 is preferably 2 or less, more preferably 1, because the luminance life of the light-emitting device using the polymer compound of the present invention is excellent.

a ^X2 is preferably 2 or less, more preferably 0, because the luminance lifetime of the light-emitting device using the polymer compound of the present invention is excellent.

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

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

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

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

As the arylene group represented by Ar ^X2 and Ar ^X4 , more preferably, the formula (A-1), the formula (A-6), the formula (A-7), the formula (A-9) to the formula (A-11) ) Or a group represented by formula (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 and the at least one divalent heterocyclic group are directly bonded to each other 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 a structural unit represented by the formulas (X-1) to (X-7), more preferably the formula (X-1) to (X-6). ), More preferably structural units represented by formulas (X-3) to (X-6).

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

[Wherein, R ^X4 and R ^X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group or cyano. Represents a group, and 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. ]

  Examples of the structural unit represented by the formula (X) include structural units represented by the formulas (X1-1) to (X1-11), and preferably the formulas (X1-3) to (X1-10). ).

<Polymer compound>
The polymer compound of the present invention includes a phosphorescent constituent unit (B) and a phosphorescent constituent unit (G), and the phosphorescent constituent unit (B) and / or the phosphorescent constituent unit (G) And have a dendron.

  In the polymer compound of the present invention, the phosphorescent structural unit (B) may be contained singly or in combination of two or more.

  The phosphorescent structural unit (B) preferably has a dendron. When the polymer compound of the present invention contains two or more types of phosphorescent structural units (B), two or more types of phosphorescence can be obtained even if one type of phosphorescent structural unit (B) has a dendron. The luminescent structural unit (B) may have a dendron.

  The content of the phosphorescent structural unit (B) is preferably relative to the total amount of the structural units contained in the polymer compound since the luminance life of the light-emitting device obtained using the polymer compound of the present invention is more excellent. Is from 0.01 to 99 mol%, more preferably from 0.1 to 70 mol%, still more preferably from 1 to 50 mol%, particularly preferably from 5 to 30 mol%.

  In the polymer compound of the present invention, the phosphorescent structural unit (G) may be contained singly or in combination of two or more.

  The phosphorescent structural unit (G) preferably has a dendron. In the case where the polymer compound of the present invention contains two or more types of phosphorescent structural units (G), two or more types of phosphorescence may be used even if one type of phosphorescent structural unit (G) has a dendron. The luminescent structural unit (G) may have a dendron.

  The content of the phosphorescent structural unit (G) is preferably relative to the total amount of the structural units contained in the polymer compound because the luminance life of the light-emitting device obtained using the polymer compound of the present invention is more excellent. Is 0.0001 to 99 mol%, more preferably 0.001 to 50 mol%, still more preferably 0.01 to 20 mol%, particularly preferably 0.05 to 5 mol%.

  In the polymer compound of the present invention, the total content of the phosphorescent structural unit (B) and the phosphorescent structural unit (G) is more excellent in the luminance life of the light-emitting device obtained using the polymer compound of the present invention. Therefore, it is preferably 0.01 to 100 mol%, more preferably 0.1 to 70 mol%, still more preferably 1 to 50 mol%, based on the total amount of the structural units contained in the polymer compound. And particularly preferably 5 to 30 mol%.

  The polymer compound of the present invention can adjust the emission color by adjusting the ratio between the content of the phosphorescent structural unit (B) and the content of the phosphorescent structural unit (G). It is also possible to adjust the emission color to white.

  The light emission color of the light emitting element can be confirmed by measuring the light emission chromaticity of the light emitting element and obtaining chromaticity coordinates (CIE chromaticity coordinates). The white emission color is, for example, in which the chromaticity coordinate X is in the range of 0.25 to 0.55, and the chromaticity coordinate Y is in the range of 0.25 to 0.55. It is preferable that the degree coordinate X is in the range of 0.28 to 0.45, and the chromaticity coordinate Y is in the range of 0.28 to 0.45.

  From the viewpoint of adjusting the luminescent color of the light-emitting element obtained using the polymer compound of the present invention (particularly adjusting the luminescent color to white), the content of the phosphorescent constituent unit (G) is determined by the phosphorescent constituent. Preferably it is 0.001-50 mol% with respect to content of a unit (B), More preferably, it is 0.01-30 mol%, More preferably, it is 0.05-10 mol%, Especially Preferably it is 0.1-5 mol%.

  When the polymer compound of the present invention contains two or more phosphorescent structural units (G), the emission color of the light-emitting element obtained using the polymer compound of the present invention is adjusted (particularly, the emission color is adjusted to white). The maximum peak wavelength of the emission spectrum of at least two phosphorescent structural units (G) is preferably different, and the difference is preferably 10 nm or more, more preferably 30 nm or more, and still more preferably 50 nm. As described above, it is particularly preferably 80 nm or more.

  When the polymer compound of the present invention contains two or more phosphorescent compounds (G) and the maximum peak wavelengths of the emission spectra of at least two phosphorescent compounds (G) are different, The content of the phosphorescent compound (G) having the maximum peak wavelength of the emission spectrum on the long wavelength side is usually relative to the content of the phosphorescent compound (G) having the maximum peak wavelength of the emission spectrum on the short wavelength side. 0.1 to 10000 mol%, since the color reproducibility of the light emitting device obtained using the polymer compound of the present invention is excellent, preferably 1 to 5000 mol%, more preferably 10 to 1000 mol%. More preferably, it is 20-500 mol%, Most preferably, it is 50-200 mol%.

  As described above, the polymer compound of the present invention may further contain a structural unit represented by the formula (Y) and / or a structural unit represented by the formula (X). Since the luminance lifetime of the light-emitting element obtained using is more excellent, it is preferable that the structural unit represented by the formula (Y) is included.

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, is superior in the luminance life of a light-emitting element obtained using the polymer compound of the present invention. Preferably it is 0.5-95 mol% with respect to the total amount of the structural unit contained, More preferably, it is 20-90 mol%, More preferably, it is 40-80 mol%.

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. Is preferably 0.1 to the total amount of the structural units contained in the polymer compound, since the charge transport property of the light-emitting device obtained using the polymer compound of the present invention is excellent. It is 50 mol%, More preferably, it is 1-40 mol%, More preferably, it is 10-30 mol%.

  The structural unit represented by the formula (Y) may be included in the polymer compound of the present invention alone or in a combination of two or more.

  The structural unit represented by the formula (X) is preferably 0.1 to 50 with respect to the total amount of the structural units contained in the polymer compound of the present invention because the hole transport property of the polymer compound of the present invention is excellent. It is mol%, More preferably, it is 1-40 mol%, More preferably, it is 5-30 mol%.

  The structural unit represented by the formula (X) may be included in the polymer compound of the present invention alone or in combination of two or more.

  Examples of the polymer compound of the present invention include polymer compounds P-1 to P-4 shown in Table 3 below. Here, the “other” structural unit refers to the phosphorescent structural unit (B), the phosphorescent structural unit (G), the structural unit represented by the formula (Y), and the structural unit represented by the formula (X). Means a structural unit other than a unit.

［表中、ｐ、ｑ、ｒ、ｓおよびｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝１００であり、かつ、１００≧ｐ＋ｑ＋ｒ＋ｓ≧７０である。その他の構成単位とは、燐光発光性構成単位（Ｂ）、燐光発光性構成単位（Ｇ）および式（Ｙ）で表される構成単位、式（Ｘ）で表される構成単位以外の構成単位を意味する。］

[In the table, p, q, r, s and t represent the molar ratio of each constituent unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70. The other structural unit is a structural unit other than the structural unit represented by the phosphorescent structural unit (B), the phosphorescent structural unit (G), the structural unit represented by the formula (Y), or the formula (X). Means. ]

  The polymer compound of the present invention may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be other embodiments. A copolymer obtained by copolymerizing plural kinds of raw material monomers is preferable.

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

The polymer compound of the present invention is, for example,
A compound represented by the formula (M-Y1);
At least one compound selected from the group consisting of a compound represented by the formula (M-Y2) and a compound represented by the formula (MX);
A group consisting of a compound represented by formula (M-1B), a compound represented by formula (M-2B), a compound represented by formula (M-3B) and a compound represented by formula (M-4B) At least one compound selected from:
A group consisting of a compound represented by formula (M-1G), a compound represented by formula (M-2G), a compound represented by formula (M-3G) and a compound represented by formula (M-4G) It can manufacture by carrying out the condensation polymerization with the at least 1 sort (s) of compound chosen from these.
In addition, when using the compound represented by a formula (M-1B) and the compound represented by a formula (M-1G), these compounds are used as terminal blocker.

  In the present specification, the compounds used for the production of the polymer compound of the present invention are sometimes collectively referred to as “raw material monomers”.

［式中、
Ａｒ^Y1、Ａｒ^X1〜Ａｒ^X4、Ｒ^X1、Ｒ^X2、Ｒ^X3、ａ^X1、ａ^X2、Ｌ^１〜Ｌ^３、Ｍ^１Ｂ〜Ｍ^３Ｂ、Ｍ^１Ｇ〜Ｍ^３Ｇ、ｎ^ａ１、ｎ^ｂ１およびｎ^ｃ１は、前記と同じ意味を表す。
Ｚ^Ｃ１〜Ｚ^Ｃ２２は、それぞれ独立に、置換基Ａ群および置換基Ｂ群からなる群から選ばれる基を示す。］

[Where:
Ar ^Y1 , Ar ^{X1 to} Ar ^X4 , R ^X1 , R ^X2 , R ^X3 , a ^X1 , a ^X2 , L ^{1 to} L ³ , M ^{1B to} M ^3B , M ^{1G to} M ^3G , n ^a1 , ^nb1 and ^nc1 Represents the same meaning as described above.
Z ^{C1 to} Z ^C22 each independently represent a group selected from the group consisting of the substituent group A and the substituent group B. ]

For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group A, Z ^{C3 to} Z ^C22 select groups selected from the substituent group B.
For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group B, Z ^{C3 to} Z ^C22 select groups selected from the substituent group A.

<Substituent group A>
A group represented by a chlorine atom, a bromine atom, an iodine atom, or —O—S (═O) ₂ R ^C1 .
(Wherein R ^C1 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.)
<Substituent group B>
-B in (OR ^C2) ₂ (wherein, R ^C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. There exist a plurality of R ^C2 is Groups which may be the same or different and may be linked to each other to form a ring structure together with the oxygen atoms to which they are bonded.
A group represented by —BF ₃ Q ′ (wherein Q ′ represents Li, Na, K, Rb or Cs);
-A group represented by MgY '(wherein Y' represents a chlorine atom, a bromine atom or an iodine atom);
A group represented by -ZnY '' (wherein Y '' represents a chlorine atom, a bromine atom or an iodine atom); and
-Sn (R ^C3) ₃ (wherein, R ^C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. More existing R ^C3 is The groups may be the same or different and may be linked to each other to form a ring structure together with the tin atoms to which they are bonded.

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

  The compound having a group selected from the substituent group A and the compound having a group selected from the substituent group B are subjected to condensation polymerization by a known coupling reaction, and the group selected from the substituent group A and the substituent group B Carbon atoms bonded to a group selected from are bonded to each other. Therefore, if a compound having one or more groups selected from Substituent Group A and a compound having one or more groups selected from Substituent Group B are subjected to a known coupling reaction, these compounds are obtained by condensation polymerization. The condensation polymer can be obtained.

  The condensation polymerization is usually performed in the presence of a catalyst, a base and a solvent, and may be performed in the presence of a phase transfer catalyst, if necessary.

  Examples of the catalyst include dichlorobis (triphenylphosphine) palladium, dichlorobis (tris-o-methoxyphenylphosphine) palladium, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium acetate and the like. Transition of nickel complexes such as palladium complexes of nickel, nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel Metal complexes; these transition metal complexes include complexes having a ligand such as triphenylphosphine, tri-o-tolylphosphine, tri (tert-butylphosphine), tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl, etc. It is done. A catalyst may be used individually by 1 type, or may use 2 or more types together.

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

  Examples of the base include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organic bases such as tetrabutylammonium fluoride and tetrabutylammonium hydroxide. . A base may be used individually by 1 type, or may use 2 or more types together.

  Examples of the phase transfer catalyst include tetrabutylammonium chloride and tetrabutylammonium bromide. A phase transfer catalyst may be used individually by 1 type, or may use 2 or more types together.

  The usage-amount of a base is 0.001-100 molar equivalent normally with respect to the total mole number of a raw material monomer.

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

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

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

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

  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>
The composition of the present invention is selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (different from the polymer compound of the present invention), an antioxidant and a solvent. At least one kind of material and the polymer compound of the present invention.

  In the composition of the present invention, the polymer compound of the present invention may be contained singly or in combination of two or more.

  The composition containing the polymer compound of the present invention and a solvent (hereinafter sometimes referred to as “ink”) is suitable for manufacturing a light-emitting element using a printing method such as an inkjet printing method or a nozzle printing method.

  The viscosity of the ink may be adjusted according to the type of printing method, but when applying a printing method such as an inkjet printing method to a printing method that passes through a discharge device, in order to prevent clogging and flight bending at the time of discharge. It is preferably 1 to 20 mPa · s at 25 ° C.

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

  In the ink, the amount of the solvent is usually 1000 to 100000 parts by weight, preferably 2000 to 20000 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

[Hole transport material]
The hole transport material is classified into a low molecular compound and a high molecular compound, and a high molecular compound is preferable, and a high molecular compound having a crosslinking group is more preferable.

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

  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 low molecular weight compounds include metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone. As well as 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 present invention, the compounding amount of the electron transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

  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 each classified into a low molecular compound and a high molecular compound. 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; a group represented by the formula (X) is included in the main chain or side chain Examples thereof include conductive polymers such as polymers.

  In the composition of the present invention, the compounding amounts of the hole injection material and the electron injection material are each usually 1 to 400 parts by weight, preferably 5 to 150 parts, per 100 parts by weight of the polymer compound of the present invention. Parts by weight.

  Each of the hole injection material and the electron 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 electrical 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.

  Only one kind or two or more kinds of ions may be doped.

[Light emitting material]
Luminescent materials (different from the polymer compound of the present invention) are classified into low-molecular compounds and polymer 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, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.

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

  The light emitting material may include a low molecular compound and a high molecular compound, and preferably includes a triplet light emitting complex and a high molecular compound.

  Examples of the triplet light-emitting complex include a phosphorescent compound represented by the formula (BM), a phosphorescent compound represented by the formula (GM), and metal complexes shown below.

  In the composition of the present invention, the content of the light emitting material is usually 0.1 to 400 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

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

  In the composition of the present invention, the blending amount of the antioxidant is usually 0.001 to 10 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

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

<Membrane>
The membrane contains the polymer compound of the present invention.

  The membrane includes an insolubilized membrane obtained by insolubilizing the polymer compound of the present invention in a solvent by crosslinking. The insolubilized film is a film obtained by crosslinking the polymer compound of the present invention by an external stimulus such as heating or light irradiation. Since the insolubilized film is substantially insoluble in a solvent, the insolubilized film can be suitably used for stacking light emitting elements.

  The heating temperature for cross-linking the film is usually 25 to 300 ° C., and the luminance life of the light emitting device including the film of the present invention is improved. Therefore, the heating temperature is preferably 50 to 250 ° C., more preferably 150 ~ 200 ° C.

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

  The film is suitable as a light emitting layer, a hole transport layer, or a hole injection layer in a light emitting device.

  The film is made of ink, for example, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method. , Flexographic printing, offset printing, ink jet printing, capillary coating, and nozzle coating.

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

<Light emitting element>
The light-emitting device of the present invention is a light-emitting device obtained by using the polymer compound of the present invention, and the polymer compound of the present invention may be cross-linked between molecules or between molecules. The molecular compound may be crosslinked in the molecule and between the molecules.
As a structure of the light emitting element of this invention, it has an electrode which consists of an anode and a cathode, and a layer obtained using the polymer compound of this invention provided between this electrode, for example.

[Layer structure]
The layer obtained by using the polymer compound of the present invention is usually one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, preferably a light emitting layer. It is. Each of these layers includes a light emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material. Each of these layers is the same as the above-described film production, in which a light-emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material are dissolved in the above-described solvent and ink is prepared and used. It can be formed using a method.

  The light emitting element has a light emitting layer between an anode and a cathode. The light-emitting element of the present invention preferably has at least one of a hole injection layer and a hole transport layer between the anode and the light-emitting layer from the viewpoint of hole injection and hole transport. From the viewpoint of injection property and electron transport property, it is preferable to have at least one of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.

  As materials for the hole transport layer, electron transport layer, light emitting layer, hole injection layer and electron injection layer, in addition to the polymer compound of the present invention, the above-described hole transport material, electron transport material, light emitting material, respectively. Examples include hole injection materials and electron injection materials.

  The material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer are used as solvents used in forming the layer adjacent to the hole transport layer, the electron transport layer, and the light emitting layer, respectively, in the production of the light emitting element. When dissolved, the material preferably has a cross-linking group in order to avoid dissolution of the material in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

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

  The order, number, and thickness of the layers to be stacked may be adjusted in consideration of the external quantum yield and device lifetime.

[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. In the case of an opaque substrate, the electrode farthest from the substrate is preferably 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 conductive compound 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 one or more species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, tin; and graphite and graphite intercalation compounds. Examples of 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.

[Usage]
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 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 active in combination with a TFT or the like. 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 also be used as a curved light source and display device.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further in detail, this invention is not limited to these Examples.

  In this example, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by size exclusion chromatography (SEC) (trade name: LC-10Avp, manufactured by Shimadzu Corporation). ). The SEC measurement conditions are as follows.

[Measurement condition]
The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 μL was injected into SEC. Tetrahydrofuran 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.

The measurement of LC-MS was performed by the following method.
The measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (manufactured by Agilent Technologies, trade name: 1100LCMSD). The mobile phase of LC-MS was used while changing the ratio of acetonitrile and tetrahydrofuran, 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.

NMR measurement was performed by the following method.
5 to 10 mg of a measurement sample was dissolved in about 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran (THF-d8) or methylene dichloride (CD ₂ Cl ₂ ), and an NMR apparatus (Varian, Inc.) was used. Manufactured and trade name MERCURY 300).

  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 in high performance liquid chromatography (HPLC, manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform to a concentration of 0.01 to 0.2% by weight, and 1 to 10 μL was injected into HPLC depending on the concentration. Acetonitrile and tetrahydrofuran were used for the mobile phase of HPLC, and it was flowed by a gradient analysis of acetonitrile / tetrahydrofuran = 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.

In this example, the maximum peak wavelength of the emission spectrum of the phosphorescent compound was measured at room temperature with a spectrophotometer (manufactured by JASCO Corporation, FP-6500). A xylene solution prepared by dissolving a phosphorescent compound 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 maximum peak wavelengths of the emission spectra of the compounds BM1, BM2, B1, GM1, GM2, G1, RM1, RM2, R1 and R2 are 472 nm, 450 nm, 450 nm, 511 nm, 534 nm, 508 nm, 601 nm, 616 nm, 617 nm and 619 nm, respectively. Met.

<Synthesis Example 1> Synthesis of Compound BM1

<Stage1>
After the inside of the reaction vessel was filled with a nitrogen gas atmosphere, iridium chloride hydrate (67.0 g), “Chemistry Material (Chem. Mater.), Vol. 18, 5119-5129 (2006)” was used. The synthesized compound L1 (128 g), 2-ethoxyethanol (570 mL) and water (190 mL) were added, and the mixture was stirred at 100 ° C. for 18 hours.
Thereafter, the reaction mixture was cooled to 15 ° C., water was added, and the precipitated solid was collected by filtration. The obtained solid was washed successively with water and hexane and then dried under reduced pressure to obtain Compound BM1a (142 g, yield 95%, yellow powder).

<Stage2>
After making the inside of reaction container nitrogen atmosphere, compound BM1a (142g), compound L1 (252), silver trifluoromethanesulfonate (46.3g), and diglyme (360mL) were added, and it stirred at 150 degreeC for 21 hours.
Thereafter, the reaction mixture was cooled to room temperature, filtered, and the obtained filtrate was concentrated under reduced pressure. Thereafter, water was added thereto, and the precipitated solid was collected by filtration. The obtained solid was washed successively with water and methanol and then dried under reduced pressure to obtain a crude product of compound BM1b.
The obtained crude product was sequentially purified by silica gel column chromatography (dichloromethane / ethyl acetate) and recrystallization (dichloromethane / methanol), and then dried under reduced pressure to obtain compound BM1b (158 g, yield 85%, yellow powder). Obtained. The HPLC area percentage value of Compound BM1b was 99.1%.

<Stage3>
After the inside of the reaction vessel was filled with a nitrogen gas atmosphere, compound BM1b (113 g), compound L2 (103 g), toluene (1100 mL), aqueous sodium carbonate (2 mol / L, 264 mL) and tetrakis (triphenylphosphine) palladium (0) ( 6.36 g) was added and the mixture was stirred at 70 ° C. for 7 hours.
Thereafter, the reaction mixture was cooled to room temperature, the aqueous layer was removed, and the obtained organic layer was washed with brine. The obtained organic layer was concentrated under reduced pressure to obtain a crude product of compound BM1c.
The obtained crude product was purified in turn by silica gel column chromatography (hexane / dichloromethane) and recrystallization (dichloromethane / methanol) and then dried under reduced pressure to give compound BM1c (61.8 g, yield 36%, yellow powder). Got. The HPLC area percentage value of compound BM1c was 86.5%.

¹ H-NMR (CDCl ₃ -d, 300 MHz): δ (ppm) = 7.81-7.72 (m, 8H), 7.62 (dd, 9H), 7.49 (dd, 8H), 7 .18 (d, 2H), 6.92 (d, 1H), 6.79 (t, 2H), 6.63 (d, 1H), 4.26 (s, 6H), 4.21 (s, 3H), 2.6-2.17 (m, 3H), 1.97-1.87 (m, 3H), 1.44-1.17 (m, 42H), 0.72 (t, 9H) .

<Stage4>
After making the inside of the reaction vessel a nitrogen gas atmosphere, compound BM1c (61.8 g), bis (pinacolato) diboron (30.2 g), potassium acetate (11.7 g), 1,4-dioxane (dehydrated product, 398 mL) and Add [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) dichloromethane complex (Pd (dppf) Cl ₂ .CH ₂ Cl ₂ , 0.65 g) and stir at 100 ° C. for 5.5 hours. did.
Thereafter, the reaction mixture was cooled to room temperature, filtered, and the obtained filtrate was concentrated to obtain a crude product of compound BM1d.
The obtained crude product was purified by silica gel column chromatography (hexane / ethyl acetate) and then dried under reduced pressure to obtain Compound BM1d (47.9 g, yield 75%, yellow powder).

¹ H-NMR (CDCl ₃ -d, 300 MHz): δ (ppm) = 7.94 (s, 1H), 7.80-7.72 (m, 9H), 7.62 (d, 8H), 7 .49 (d, 8H), 7.15 (t, 2H), 6.90-6.76 (m, 3H), 4.28 (s, 3H), 4.25 (s, 3H), 4. 23 (s, 3H), 2.29-2.15 (m, 3H), 1.98-1.86 (m, 3H), 1.41-1.17 (m, 54H), 0.72 ( t, 9H).

<Stage5>
After making the inside of the reaction vessel a nitrogen gas atmosphere, compound BM1d (45.7 g), 1,3,5-tribromobenzene (45.0 g), toluene (571 mL), aqueous sodium carbonate solution (1 mol / L, 86 mL), Methyl trioctyl ammonium chloride (manufactured by Sigma-Aldrich, trade name Aliquat 336 (registered trademark)) (0.35 g) and tetrakis (triphenylphosphine) palladium (0) (1.65 g) were added, and the mixture was stirred at 110 ° C. for 3 hours. .
Thereafter, the reaction mixture was cooled, the aqueous layer was removed, and the resulting organic layer was washed with brine. The obtained organic layer was concentrated under reduced pressure to obtain a crude product of compound BM1.
The obtained crude product was purified in turn by silica gel column chromatography (hexane / ethyl acetate), recrystallization (toluene / methanol), and recrystallization (ethyl acetate / methanol), and then dried under reduced pressure to give compound BM1 (31.31). 6 g, yield 65%, yellow powder). The HPLC area percentage value of Compound BM1 was 99.5% or more.

¹ H-NMR (CDCl ₃ -d, 300 MHz): δ (ppm) = 7.82 (s, 2H), 7.74 (d, 6H), 7.64-7.56 (m, 12H), 7 .49 (d, 8H), 7.21-7.17 (m, 2H), 7.00 (d, 1H), 6.87 (d, 2H), 6.77 (d, 1H), 4. 30 (s, 3H), 4.26 (s, 6H), 2.30-2.20 (m, 3H), 2.05-1.88 (m, 3H), 1.40-1.16 ( m, 42H), 0.70 (t, 9H).
LC-MS (UV254 nm-APCI positive): m / z = 1705.6 [M + H] ⁺

<Synthesis Example 2> Synthesis of Compound BM2

  After making the inside of the reaction vessel a nitrogen gas atmosphere, compound BM2a (45.7 g) and N, N-dimethylformamide (90 ml) synthesized according to the method described in JP2013-147450A were added and cooled in an ice bath. did. Thereto, N-bromosuccinimide (1.58 g) dissolved in N, N-dimethylformamide (90 ml) was added dropwise over 4.5 hours, followed by stirring at 0 ° C. for 30 minutes. Thereto was added a 0.1 wt% aqueous sodium sulfite solution (180 g), and the mixture was stirred at room temperature for 15 minutes, and then ethyl acetate and toluene were added, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water and then concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (toluene / ethyl acetate), recrystallized using a mixed solvent of ethyl acetate and methanol, and further recrystallized using a mixed solvent of ethyl acetate and hexane. Thereafter, the resultant was dried under reduced pressure to obtain Compound BM2 (2.80 g, yield 65%, yellow solid). The HPLC area percentage value of Compound BM2 was 99.5% or more.

¹ H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.67 (d, 2H), 7.59 (d, 1H), 7.00-6.81 (m, 4H), 6 .61 (d, 1H), 6.60 (t, 2H), 4.23 (s, 9H), 2.27-2.16 (m, 3H), 1.94-1.82 (m, 3H) ), 1.41-1.25 (m, 6H), 0.74 (t, 9H).

<Synthesis Example 3> Synthesis of Compounds B1, G1, R1, and R2 Compound B1 was synthesized according to the method described in JP2013-147450A.
Compound G1 was synthesized according to the method described in JP2013-237789A.
Compound R1 was synthesized according to the method described in WO2002 / 44189.
Compound R2 was synthesized according to the method described in JP-A-2006-188673.

<Synthesis Example 4> Synthesis of polymer compound HTL-1 Polymer compound HTL-1 is compound M7 synthesized according to the method described in JP 2011-174062 A, according to the method described in International Publication No. 2002/045184. Using synthesized compound M8, compound M9 synthesized according to the method described in WO 2005/049546, and compound M10 synthesized according to the method described in JP 2008-106241 A, JP 2011-174062 A Synthesized according to the method described in the publication.

The number average molecular weight and weight average molecular weight in terms of polystyrene of the polymer compound HTL-1 were Mn = 7.8 × 10 ⁴ and Mw = 2.6 × 10 ⁵ , respectively.

  The high molecular compound HTL-1 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M7, a structural unit derived from the compound M8, a structural unit derived from the compound M9, and a compound. The structural unit derived from M10 is a copolymer composed of a molar ratio of 50: 12.5: 30: 7.5.

<Synthesis Example 5> Synthesis of Polymer Compound HP-1 Polymer compound HP-1 is compound M1, synthesized according to the method described in JP 2010-189630 A, and according to the method described in International Publication No. 2013/199088. The compound M2 synthesized and the compound M3 synthesized according to the method described in International Publication No. 2013/201188 were synthesized according to the method described in International Publication No. 2013/200988.

The number average molecular weight and weight average molecular weight in terms of polystyrene of the polymer compound HP-1 were Mn = 8.8 × 10 ⁴ and Mw = 2.3 × 10 ⁵ , respectively.

  The theoretical value obtained from the amount of the raw material used for polymer compound HP-1 is that the structural unit derived from compound M1, the structural unit derived from compound M2, and the structural unit derived from compound M3 are: It is a copolymer formed with a molar ratio of 50:26:24.

<Synthesis Example 6> Synthesis of polymer compound HP-2 (Step 1) in the synthesis of polymer compound P-1 to be described later is described as “After the inside of the reaction vessel is set to an inert gas atmosphere, compound M1 (0.745 g) Compound M3 (1.26 g) and toluene (35 ml) were added, and the mixture was heated to 80 ° C. According to the method described in the synthesis of polymer compound P-1 described later, polymer compound HP was used. -2 was obtained 1.2g. The high molecular compound HP-2 had Mn of 1.1 × 10 ⁵ and Mw of 3.4 × 10 ⁵ .

  The theoretical value obtained from the amount of charged raw materials for the polymer compound HP-2 is that the structural unit derived from the compound M1 and the structural unit derived from the compound M3 are configured in a molar ratio of 50:50. It is a copolymer.

<Example P1> Synthesis of polymer compound P-1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, synthesis was performed according to the method described in Compound M1 (0.747 g), International Publication No. 2013/199088. Compound M2 (0.384 g), Compound M3 (0.520 g), Compound BM1 (0.739 g), Compound GM1 (0.00481 g) synthesized according to the method described in International Publication No. 2013/021180, Compound RM1 (0.00594 g) and toluene (45 ml) synthesized according to the method described in Kaikai 2011-105701 were added and heated to 80 ° C. Thereafter, bis [tris (2-methoxyphenyl) phosphine] palladium dichloride (2.65 mg) and a 20 wt% aqueous tetraethylammonium hydroxide solution (9.3 g) were added thereto, and the temperature of the oil bath was adjusted to 100 ° C. Stir for hours.

  (Step 2) Phenylboronic acid (0.0369 g), bis [tris (2-methoxyphenyl) phosphine] palladium dichloride (1.29 mg) and a 20 wt% tetraethylammonium hydroxide aqueous solution (9. 3 g) was added, and the temperature of the oil bath was set to 100 ° C. and stirred for 16 hours.

(Step 3) A sodium diethyldithiacarbamate aqueous solution was added to the reaction solution, followed by stirring for 2 hours while heating to 85 ° C. The reaction solution was cooled to room temperature, the aqueous layer was removed, and then washed twice with 3.6 wt% hydrochloric acid, twice with 2.5 wt% aqueous ammonia, and four times with ion-exchanged water. When the obtained solution was added dropwise to methanol, precipitation occurred. The precipitate was collected by filtration and dried to obtain a solid. This solid was dissolved in toluene and purified by passing through an alumina column and a silica gel column which had been passed through toluene in advance. When the purified liquid was added dropwise to methanol and stirred, a precipitate was formed. The precipitate was collected by filtration and dried to obtain polymer compound P-1 (1.5 g). Mn of the polymer compound P-1 was 1.3 × 10 ⁵ , and Mw was 3.8 × 10 ⁵ .

  The polymer compound P-1 has the theoretical values determined from the amounts of raw materials charged, the structural unit derived from the compound M1, the structural unit derived from the compound M2, the structural unit derived from the compound M3, and the compound. The structural unit derived from BM1, the structural unit derived from compound GM1, and the structural unit derived from compound RM1 are 50: 15: 20.5: 14.3: 0.1: 0.1. It is a copolymer formed by a molar ratio.

<Example P2> Synthesis of polymer compound P-2

(Step 1) in the synthesis of the polymer compound P-1 was made as follows: “After the inside of the reaction vessel was set to an inert gas atmosphere, Compound M1 (0.863 g), Compound M3 (1.29 g), Compound BM1 (0.466 g ), Compound GM1 (0.00575 g) and toluene (45 ml) were added and heated to 80 ° C. ”, except that the polymer compound P- was prepared according to the method described in the synthesis of polymer compound P-1. 1.6 g of 2 was obtained. Mn of the polymer compound P-2 was 9.1 × 10 ⁴ , and Mw was 2.1 × 10 ⁵ .

  The polymer compound P-2 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M1, a structural unit derived from the compound M3, a structural unit derived from the compound BM1, and a compound. The structural unit derived from GM1 is a copolymer composed of a molar ratio of 50: 42.4: 7.5: 0.1.

<Comparative Example CP1> Synthesis of Polymer Compound CP-1

(Step 1) in the synthesis of the polymer compound P-1 is as follows: “After making the inside of the reaction vessel an inert gas atmosphere, the compound M1 (0.562 g), the compound M2 (0.320 g), the compound M3 (0.433 g) ), Compound BM2 (0.340 g), Compound GM2 (0.00245 g) synthesized according to the method described in JP-A-2005-251609, Compound RM2 synthesized according to the method described in International Publication No. 2006/003000 (0.00260 g) and toluene (45 ml) were added, and the mixture was heated to 80 ° C. ”, except that the polymer compound CP-1 was added in an amount of 0.00 according to the method described in the synthesis of the polymer compound P-1. 78 g was obtained. The Mn of the polymer compound CP-1 was 1.8 × 10 ⁴ and the Mw was 4.0 × 10 ⁴ .

  The polymer compound CP-1 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M1, a structural unit derived from the compound M2, a structural unit derived from the compound M3, and a compound. The structural unit derived from BM2, the structural unit derived from compound GM2, and the structural unit derived from compound RM2 are 50: 15: 20.5: 14.3: 0.1: 0.1. It is a copolymer formed by a molar ratio.

<Example D1> Fabrication and evaluation of light-emitting element D1 (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)
The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% 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)
The polymer compound P-1 was dissolved in xylene at a concentration of 1.5% by weight. 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 cathode)
The substrate on which the light emitting layer is formed is depressurized to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the light emitting layer, and then on the sodium fluoride layer. Aluminum was deposited at about 80 nm. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.

EL light emission was observed by applying a voltage to the light emitting element D1. The chromaticity CIE (X, Y) at 1000 cd / m ² of the light-emitting element D1 was (0.38, 0.36).

The luminance half life of driving the light emitting element D1 with a constant current after setting the current value so that the initial luminance was 1000 cd / m ² was 15.1 hours.

<Example D2> Fabrication and Evaluation of Light-Emitting Element D2 Instead of "High molecular compound P-1 was dissolved in xylene at a concentration of 1.5% by weight" in Example D1, instead of "High in xylene, The molecular compound P-2 and the compound R2 (polymer compound P-2 / compound R2 = 99.65 wt% / 0.35 wt%) were dissolved at a concentration of 1.7 wt%. A light emitting device D2 was fabricated in the same manner as Example D1.

EL light emission was observed by applying a voltage to the light emitting element D2. The chromaticity CIE (X, Y) at 1000 cd / m ² of the light-emitting element D2 was (0.29, 0.36).

The luminance half life of driving the light emitting element D2 with a constant current after setting the current value so that the initial luminance was 1000 cd / m ² was 14.0 hours.

<Comparative Example CD1> Production and Evaluation of Light-Emitting Element CD1 In place of “High molecular compound P-1 was dissolved in xylene at a concentration of 1.5% by weight” in Example D1, “High in xylene. A light emitting device CD1 was produced in the same manner as in Example D1, except that the molecular compound CP-1 was dissolved at a concentration of 2.5% by weight.

EL light emission was observed by applying a voltage to the light emitting device CD1. The chromaticity CIE (X, Y) at 1000 cd / m ² of the light emitting device CD1 was (0.36, 0.33).

The luminance half life of driving the light emitting element CD1 with a constant current after setting the current value so that the initial luminance was 1000 cd / m ² was 0.03 hours.

<Comparative Example CD2> Production and Evaluation of Light-Emitting Element CD2 Instead of “High molecular compound P-1 was dissolved in xylene at a concentration of 1.5 wt%” in Example D1, “High in xylene, Molecular compound HP-1, compound B1, compound G1 and compound R1 (polymer compound HP-1 / compound B1 / compound G1 / compound R1 = 59 wt% / 40 wt% / 0.6 wt% / 0.4 wt% ) Was dissolved at a concentration of 1.8 wt%, and a light emitting device CD2 was produced in the same manner as in Example D1.

EL light emission was observed by applying a voltage to the light emitting device CD2. The chromaticity CIE (X, Y) at 1000 cd / m ² of the light emitting device CD2 was (0.50, 0.40).

The luminance half life of driving the light emitting element CD2 with a constant current after setting the current value so that the initial luminance was 1000 cd / m ² was 4.1 hours.

<Comparative Example CD3> Production and Evaluation of Light-Emitting Element CD3 In place of “High molecular compound P-1 was dissolved in xylene at a concentration of 1.5% by weight” in Example D1, “High in xylene. Molecular compound HP-2, compound B1, compound G1 and compound R2 (polymer compound HP-2 / compound B1 / compound G1 / compound R2 = 59 wt% / 40 wt% / 0.6 wt% / 0.4 wt% ) Was dissolved at a concentration of 1.8 wt%, and a light emitting device CD3 was fabricated in the same manner as in Example D1.

EL light emission was observed by applying a voltage to the light emitting device CD3. The chromaticity CIE (X, Y) at 1000 cd / m ² of the light emitting device CD3 was (0.47, 0.42).

The luminance half life of driving the light emitting element CD2 with a constant current after setting the current value so that the initial luminance was 1000 cd / m ² was 2.7 hours.

Claims (15)

A phosphorescent constituent unit (B) having the structure of the phosphorescent compound (B) having a maximum peak wavelength of the emission spectrum of 400 nm or more and less than 480 nm, and a phosphorescence emitting property having a maximum peak wavelength of the emission spectrum of 480 nm or more and less than 680 nm. A phosphorescent structural unit (G) having the structure of compound (G),
A polymer compound, wherein at least one structural unit selected from the group consisting of a phosphorescent structural unit (B) and a phosphorescent structural unit (G) is a phosphorescent structural unit having a dendron. The polymer compound according to claim 1, wherein the phosphorescent structural unit (B) is a structural unit represented by the formula (1B), (2B), (3B), or (4B).

[Where:
M ^1B is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. Represents.
L ¹ represents an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C≡C—, an arylene group or It represents a divalent heterocyclic group, and these groups may 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 ^1B represents the same meaning as described above.
L ² and L ³ each independently represent an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C Represents ≡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 an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. ]

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^2B is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. Represents. ]

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^3B is a group obtained by removing three hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (B) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. Represents. ]   The polymer compound according to claim 2, wherein the phosphorescent structural unit (B) is a structural unit represented by the formula (2B) or (3B). The polymer compound according to any one of claims 1 to 3, wherein the phosphorescent compound (B) is a phosphorescent compound represented by the formula (BM).

[Where:
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ^1B represents an integer of 1 or more. n ^2B represents an integer of 0 or more. However, n ^1B + n ^2B is 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ^1B + n ^2B is 3, and when M is a palladium atom or platinum atom, n ^1B + n ^2B is 2.
E ¹ and E ² each independently represents a carbon atom or a nitrogen atom. When a plurality of E ¹ and E ² are present, they may be the same or different. However, at least one of E ¹ and E ² is a carbon atom.
Ring R ^1B represents a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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 ^1B are present, they may be the same or different. However, when ring R ^1B is a 6-membered aromatic heterocycle, E ¹ is a carbon atom.
Ring R ^2B represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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 ^2B are present, they may be the same or different. However, when the ring R ^2B is a 6-membered aromatic heterocyclic ring, E ² is a carbon atom.
However, when the ring R ^1B is a 6-membered aromatic heterocyclic ring, the ring R ^2B has an electron withdrawing group.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand, and G ¹ represents an atomic group constituting a bidentate ligand together with A ¹ and A ² . 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. When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ] The polymer compound according to claim 4, wherein the ring R ^1B is a pyridine ring, a pyrimidine ring, an imidazole ring, a pyrazole ring or a triazole ring. The polymer compound according to claim 4 or 5, wherein the ring R ^2B is a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, diazabenzene ring, pyrrole ring, furan ring or thiophene ring. The phosphorescent structural unit (G) is a structural unit represented by the formula (1G), (2G), (3G) or (4G), according to any one of claims 1 to 6. Molecular compound.

[Where:
M ^1G is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. Represents.
L ¹ represents an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C≡C—, an arylene group or It represents a divalent heterocyclic group, and these groups may 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 the same meaning as described above.
L ² and L ³ each independently represent an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C Represents ≡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 an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. ]

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^2G is a group obtained by removing two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. Represents. ]

[Where:
L ² and n ^b1 represent the same meaning as described above.
M ^3G is a group obtained by removing three hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the compound from a phosphorescent compound (G) having a maximum peak wavelength of an emission spectrum of 480 nm or more and less than 680 nm. Represents. ]   The polymer compound according to claim 7, wherein the phosphorescent structural unit (G) is a structural unit represented by the formula (2G) or (3G). The polymer compound according to any one of claims 1 to 8, wherein the phosphorescent compound (G) is a phosphorescent compound represented by the formula (GM).

[Where:
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ^1G represents an integer of 1 or more. n ^2G represents an integer of 0 or more. However, n ^1G + n ^2G is 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ^1G + n ^2G is 3, and when M is a palladium atom or platinum atom, n ^1G + n ^2G is 2.
E ⁴ represents a carbon atom or a nitrogen atom. When a plurality of E ⁴ are present, they may be the same or different.
Ring R ^1G represents a 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such 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 represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and these rings optionally have a substituent. When a plurality of such 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.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand, and G ¹ represents an atomic group constituting a bidentate ligand together with A ¹ and A ² . 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. When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ] The polymer compound according to claim 9, wherein the ring R ^1G is a pyridine ring, a diazabenzene ring, a quinoline ring or an isoquinoline ring. The polymer compound according to claim 1, wherein the dendron is a group represented by the formula (DA) or (DB).

[Where:
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups 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.
^TDA 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. ]

[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.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and 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.
^TDA 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. ] The group represented by the formula (DA) is a group represented by the formula (D-A1), (D-A2), (D-A3) or (D-A4). The polymer compound described.

[Where:
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 optionally have a substituent. A plurality of ^RDAs may be the same or different.
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. A plurality of np1 may be the same or different. ] The high molecular compound as described in any one of Claims 1-12 which further contains the structural unit represented by a 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, and these This group may have a substituent. ] The polymer compound according to any one of claims 1 to 13,
A composition containing at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent.   The light emitting element using the high molecular compound as described in any one of Claims 1-13.