JP2018078286A - Composition and light-emitting element arranged by use thereof - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition useful in manufacturing a light-emitting element superior in external quantum efficiency.SOLUTION: A composition comprises: a polymer compound including a constituting unit represented by the formula (Z); a compound represented by the formula (1); and a phosphorescent compound.SELECTED DRAWING: None

Description

  The present invention relates to a composition and a light emitting device using the composition.

  Light-emitting elements such as organic electroluminescence elements can be suitably used for display and lighting applications. As a light-emitting material used for a light-emitting layer of a light-emitting element, for example, a composition composed of a polymer compound containing a structural unit represented by the following formula and a phosphorescent compound is known.

JP 2012-036388 A

  However, a light emitting device manufactured using this composition does not necessarily have sufficient external quantum efficiency. Then, an object of this invention is to provide a composition useful for manufacture of the light emitting element which is excellent in external quantum efficiency.

The present invention provides the following [1] to [8].
[1]
The composition containing the high molecular compound containing the structural unit represented by Formula (Z), the compound represented by Formula (1), and a phosphorescence-emitting compound.

［式中、
Ａｒ^Zは、環内に−Ｎ＝で表される基を有する２価の複素環基を表し、この基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。
Ａｒ^Z1及びＡｒ^Z2は、それぞれ独立に、アリーレン基又は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^Z1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。Ａｒ^Z2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^Z1及びｎ^Z2は、それぞれ独立に、０以上５以下の整数を表す。］

[Where:
Ar ^Z represents a divalent heterocyclic group having a group represented by —N═ in the ring, and this group may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
Ar ^Z1 and Ar ^Z2 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar ^Z1 are present, they may be the same or different. When a plurality of Ar ^Z2 are present, they may be the same or different.
n ^Z1 and n ^Z2 each independently represent an integer of 0 or more and 5 or less. ]

［式中、
Ａｒ¹は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。該置換基が複数存在する場合、それらは互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
ｎ¹は、１以上５以下の整数を表す。
ｎ²は、０以上５以下の整数を表す。ｎ²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。
Ａｒ²は、アリーレン基又は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。Ａｒ²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。
Ｒ¹及びＲ²は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ¹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。Ｒ²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。
Ａｒ²、Ｒ¹及びＲ²はそれぞれ、該基が結合している窒素原子に結合している該基以外の基と、直接結合して、又は、２価の基を介して結合して、環を形成していてもよい。］
［２］
前記燐光発光性化合物が、式（Ｍ）で表される金属錯体である、［１］に記載の組成物。

[Where:
Ar ¹ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
n ¹ represents an integer of 1 to 5.
n ² represents an integer of 0 or more and 5 or less. When a plurality of n ² are present, they may be the same or different.
Ar ² represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar ² are present, they may be the same or different.
R ¹ and R ² each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of R ¹ are present, they may be the same or different. When a plurality of R ² are present, they may be the same or different.
Ar ² , R ¹ and R ² are each bonded directly to a group other than the group bonded to the nitrogen atom to which the group is bonded, or bonded via a divalent group; A ring may be formed. ]
[2]
The composition according to [1], wherein the phosphorescent compound is a metal complex represented by the formula (M).

［式中、
Ｍ¹は、イリジウム原子又は白金原子を表す。
ｎ^M1は１以上の整数を表し、ｎ^M2は０以上の整数を表す。但し、Ｍ¹がイリジウム原子の場合、ｎ^M1＋ｎ^M2は３であり、Ｍ¹が白金原子の場合、ｎ^M1＋ｎ^M2は２である。
Ｅ¹及びＥ²は、それぞれ独立に、炭素原子又は窒素原子を表す。但し、Ｅ¹及びＥ²の少なくとも一方は炭素原子である。
環Ｒ^M1は、芳香族複素環を表し、こ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^M1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^M2は、芳香族炭化水素環又は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^M2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^M1が有していてもよい置換基と環Ｒ^M2が有していてもよい置換基とは、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
−Ａ^D1---Ａ^D2−は、アニオン性の２座配位子を表す。Ａ^D1及びＡ^D2は、それぞれ独立に、Ｍ¹と結合する炭素原子、酸素原子又は窒素原子を表し、これらの原子は環を構成する原子であってもよい。−Ａ^D1---Ａ^D2−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。］
［３］
式（Ｍ）で表される金属錯体が、式Ir-1、式Ir-2、式Ir-3、式Ir-4、又は、式Ir-5で表される金属錯体である、［２］に記載の組成物。

[Where:
M ¹ represents an iridium atom or a platinum atom.
n ^M1 represents an integer of 1 or more, and n ^M2 represents an integer of 0 or more. However, when M ¹ is an iridium atom, n ^M1 + n ^M2 is 3, and when M ¹ is a platinum atom, n ^M1 + n ^M2 is 2.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. However, at least one of E ¹ and E ² is a carbon atom.
Ring R ^M1 represents an aromatic heterocyclic ring, and this ring may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When there are a plurality of rings R ^M1 , they may be the same or different.
Ring R ^M2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings R ^M2 are present, they may be the same or different.
The substituent that the ring R ^M1 may have and the substituent that the ring R ^M2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
-A ^D1 --- A ^D2 -represents an anionic bidentate ligand. A ^D1 and A ^D2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom bonded to M ^1, and these atoms may be atoms constituting a ring. When a plurality of -A ^D1 --- A ^D2 -are present, they may be the same or different. ]
[3]
The metal complex represented by Formula (M) is a metal complex represented by Formula Ir-1, Formula Ir-2, Formula Ir-3, Formula Ir-4, or Formula Ir-5, [2] A composition according to 1.

［式中、
Ｒ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7、Ｒ^D8、Ｒ^D11、Ｒ^D12、Ｒ^D13、Ｒ^D14、Ｒ^D15、Ｒ^D16、Ｒ^D17、Ｒ^D18、Ｒ^D19、Ｒ^D20、Ｒ^D21、Ｒ^D22、Ｒ^D23、Ｒ^D24、Ｒ^D25、Ｒ^D26、Ｒ^D31、Ｒ^D32、Ｒ^D33、Ｒ^D34、Ｒ^D35、Ｒ^D36及びＲ^D37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、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。Ｒ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7、Ｒ^D8、Ｒ^D11、Ｒ^D12、Ｒ^D13、Ｒ^D14、Ｒ^D15、Ｒ^D16、Ｒ^D17、Ｒ^D18、Ｒ^D19、Ｒ^D20、Ｒ^D21、Ｒ^D22、Ｒ^D23、Ｒ^D24、Ｒ^D25、Ｒ^D26、Ｒ^D31、Ｒ^D32、Ｒ^D33、Ｒ^D34、Ｒ^D35、Ｒ^D36及びＲ^D37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。
Ｒ^D1とＲ^D2、Ｒ^D2とＲ^D3、Ｒ^D3とＲ^D4、Ｒ^D4とＲ^D5、Ｒ^D5とＲ^D6、Ｒ^D6とＲ^D7、Ｒ^D7とＲ^D8、Ｒ^D11とＲ^D12、Ｒ^D12とＲ^D13、Ｒ^D13とＲ^D14、Ｒ^D14とＲ^D15、Ｒ^D15とＲ^D16、Ｒ^D16とＲ^D17、Ｒ^D17とＲ^D18、Ｒ^D18とＲ^D19、Ｒ^D19とＲ^D20、Ｒ^D22とＲ^D23、Ｒ^D23とＲ^D24、Ｒ^D24とＲ^D25、Ｒ^D25とＲ^D26、Ｒ^D31とＲ^D32、Ｒ^D32とＲ^D33、Ｒ^D33とＲ^D34、Ｒ^D34とＲ^D35、Ｒ^D35とＲ^D36、及び、Ｒ^D36とＲ^D37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。
−Ａ^D1---Ａ^D2−は、前記と同じ意味を表す。
ｎ_D1は、１、２又は３を表し、ｎ_D2は、１又は２を表す。］
［４］
前記Ａｒ¹が、置換基を有していてもよい縮合環の芳香族炭化水素基、又は、置換基を有していてもよい縮合環の複素環基である、［１］〜［３］のいずれかに記載の組成物。
［５］
前記Ａｒ^Zが、ジアゾール環、トリアゾール環、オキサジアゾール環、チアジアゾール環、チアゾール環、オキサゾール環、イソチアゾール環、イソオキサゾール環、ベンゾジアゾール環、ベンゾトリアゾール環、ベンゾオキサジアゾール環、ベンゾチアジアゾール環、ベンゾチアゾール環、ベンゾオキサゾール環、アザカルバゾール環、ジアザカルバゾール環、ピリジン環、ジアザベンゼン環、トリアジン環、アザナフタレン環、ジアザナフタレン環、トリアザナフタレン環、テトラアザナフタレン環、アザアントラセン環、ジアザアントラセン環、トリアザアントラセン環、テトラアザアントラセン環、アザフェナントレン環、ジアザフェナントレン環、トリアザフェナントレン環又はテトラアザフェナントレン環から、環を構成する炭素原子に直接結合する水素原子２個を除いた基（該基は置換基を有していてもよい）である、［１］〜［４］のいずれかに記載の組成物。
［６］
正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料及び酸化防止剤からなる群より選ばれる少なくとも１種を更に含有する、［１］〜［５］のいずれかに記載の組成物。
［７］
溶媒を更に含有する、［１］〜［６］のいずれかに記載の組成物。
［８］
［１］〜［６］のいずれかに記載の組成物を含有する発光素子。

[Where:
R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 are each independently a hydrogen atom Represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups may have a substituent. Good. R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 Each may be the same or different.
R ^D1 and R ^D2 , R ^D2 and R ^D3 , R ^D3 and R ^D4 , R ^D4 and R ^D5 , R ^D5 and R ^D6 , R ^D6 and R ^D7 , R ^D7 and R ^D8 , R ^D11 and R ^D12 , R ^D12 And R ^D13 , R ^D13 and R ^D14 , R ^D14 and R ^D15 , R ^D15 and R ^D16 , R ^D16 and R ^D17 , R ^D17 and R ^D18 , R ^D18 and R ^D19 , R ^D19 and R ^D20 , R ^D22 and R ^D23 , R ^D23 and R ^D24 , R ^D24 and R ^D25 , R ^D25 and R ^D26 , R ^D31 and R ^D32 , R ^D32 and R ^D33 , R ^D33 and R ^D34 , R ^D34 and R ^D35 , R ^D35 and R ^D36 , R ^D36 and R ^D37 may be bonded to each other to form a ring together with the atoms to which they are bonded.
-A ^D1 --- A ^D2- represents the same meaning as described above.
n _D1 represents 1, 2 or 3, and n _D2 represents 1 or 2. ]
[4]
[1] to [3], wherein Ar ¹ is a condensed ring aromatic hydrocarbon group which may have a substituent, or a condensed ring heterocyclic group which may have a substituent. The composition in any one of.
[5]
Ar ^Z is a diazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiazole ring, oxazole ring, isothiazole ring, isoxazole ring, benzodiazole ring, benzotriazole ring, benzooxadiazole ring, benzothiadiazole Ring, benzothiazole ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring , Diazaanthracene ring, triazaanthracene ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring or tetraazaphenanthrene ring A direct bond to a hydrogen atom two group remaining after removing the atom (said group may be substituted), A composition according to any one of [1] to [4].
[6]
Any one of [1] to [5], further containing at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. Composition.
[7]
The composition according to any one of [1] to [6], further containing a solvent.
[8]
The light emitting element containing the composition in any one of [1]-[6].

  ADVANTAGE OF THE INVENTION According to this invention, the composition useful for manufacture of the light emitting element which is excellent in external quantum efficiency can be provided. Moreover, according to this invention, the light emitting element containing this composition can be provided.

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

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

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

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

  In the formula representing the metal complex, the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.

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

  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 or the luminance life may be lowered when the polymer compound is used for the production of a light emitting device. It is. The terminal group of the polymer compound is preferably a group that is conjugated to the main chain, such as an aryl group or a monovalent heterocyclic group that is bonded to the main chain of the polymer compound via a carbon-carbon bond. And a group bonded to each other.

“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, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl And a group in which a hydrogen atom in these groups 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 peroxy group, and the like. Fluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- Examples include (3,5-di-hexylphenyl) 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 6 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.

The “p-valent heterocyclic group” (p represents an integer of 1 or more) is p 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, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is 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 compound in which an aromatic ring is condensed to a heterocyclic ring, even if the heterocyclic ring itself does not exhibit aromaticity, such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran Means.

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, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl 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, bis (3,5-di-tert- Butylphenyl) amino group.

The “alkenyl group” may be linear or branched. The number of carbon atoms 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, and 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, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups 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 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, 4- Examples include a pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which these groups have a substituent.

The “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30 and more preferably 6 to 18 without including the number of carbon atoms of the substituent.
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及びＲ^aは、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表す。複数存在するＲ及びＲ^aは、各々、同一でも異なっていてもよく、Ｒ^a同士は互いに結合して、それぞれが結合する原子と共に環を形成していてもよい。］

[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 atoms to which they are bonded. ]

The carbon atom number of a bivalent heterocyclic group is 2-60 normally without including the carbon atom number of a substituent, Preferably, it is 3-20, More preferably, it is 4-15.
The divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, 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及び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 heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. B-1) is a group represented by any one of formulas (B-17). 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 crosslinking group.

<Polymer Compound Containing Structural Unit Represented by Formula (Z)>
[Structural Unit Represented by Formula (Z)]
In the divalent heterocyclic group having a group represented by —N═ in the ring, the number of groups represented by —N═ is usually 1 to 10, preferably 1 to 5, More preferably, it is 1-3, More preferably, it is 3.

  In the divalent heterocyclic group having a group represented by —N═ in the ring, the number of carbon atoms constituting the ring is usually 1 to 60, preferably 2 to 30, more preferably. It is 3-15, More preferably, it is 3-5.

  Examples of the divalent heterocyclic group having a group represented by —N═ in the ring include a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiazole ring, an oxazole ring, an isothiazole ring, an isoxazole ring, Benzooxadiazole ring, benzothiadiazole ring, benzothiazole ring, benzoxazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring, A diazaanthracene ring, a triazaanthracene ring, a tetraazaanthracene ring, an azaphenanthrene ring, a diazaphenanthrene ring, a triazaphenanthrene ring, a tetraazaphenanthrene ring, and a ring obtained by condensing an aromatic ring to these heterocycles. Composing carbon A group in which two hydrogen atoms directly bonded to a child or a hetero atom are excluded, and the external quantum efficiency of the light-emitting device containing the composition of the present invention (that is, the light-emitting device of the present invention) is more preferable. , Diazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiazole ring, oxazole ring, isothiazole ring, isoxazole ring, benzodiazole ring, benzotriazole ring, benzooxadiazole ring, benzothiadiazole ring, benzothiazole Ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring, diazaanthracene Ring, Triazaanthra Ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring or tetraazaphenanthrene ring, a group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring, and more Preferably, a diazole ring, a triazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, an azaanthracene ring, a diazaanthracene ring, a tria A group obtained by removing two hydrogen atoms directly bonded to the carbon atoms constituting the ring from the anthracene ring, azaphenanthrene ring, diazaphenanthrene ring or triazaphenanthrene ring, more preferably a pyridine ring, a diazabenzene ring, Triazine ring, azanaphth Directly to the carbon atoms constituting the ring from the thalene ring, diazanaphthalene ring, triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring or triazaphenanthrene ring A group in which two hydrogen atoms to be bonded are removed, particularly preferably a group in which two hydrogen atoms directly bonded to a carbon atom constituting the ring are removed from a pyridine ring, a diazabenzene ring or a triazine ring, particularly preferably Is a group in which two hydrogen atoms directly bonded to the carbon atoms constituting the ring are removed from the triazine ring, and these groups optionally have a substituent.

Since the synthesis of the polymer compound is facilitated, the substituent that Ar ^Z may have includes an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent complex. A cyclic group, a substituted amino group or a halogen atom is preferred, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group, An aryl group or a monovalent heterocyclic group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is particularly preferred, an aryl group is particularly preferred, and these groups may further have a substituent.
Since the external quantum efficiency of the light emitting device of the present invention is more excellent, Ar ^Z may have a substituent as an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic ring. Group or substituted amino group is preferred, aryl group, monovalent heterocyclic group or substituted amino group is more preferred, aryl group or monovalent heterocyclic group is further preferred, aryl group is particularly preferred, and these groups are further substituted It may have a group.

When there are a plurality of substituents that Ar ^Z may have, it is preferable that they are bonded to each other and do not form a ring with the atoms to which they are bonded.

The substituent that Ar ^Z may have may further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent heterocyclic ring. Group, substituted amino group or halogen atom is preferable, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group or monovalent heterocyclic group is more preferable, alkyl group, cycloalkyl group, aryl group or monovalent group. The heterocyclic group is more preferable, an alkyl group or an aryl group is particularly preferable, an alkyl group is particularly preferable, and these groups may further have a substituent.

Ar ^Z is preferably a group represented by the formula (ArZ-1) to the formula (ArZ-12), more preferably the formula (ArZ-), because the external quantum efficiency of the light emitting device of the present invention is more excellent. 1) to a group represented by formula (ArZ-9), more preferably a group represented by formula (ArZ-1) to formula (ArZ-5), and particularly preferably a group represented by formula (ArZ- 1), a group represented by formula (ArZ-2) or formula (ArZ-4), and particularly preferably a group represented by formula (ArZ-4).

［式中、Ｒ^1Z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、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又は結合手を表し、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^1Zは、同一でも異なっていてもよい。但し、複数存在するＲ^1Zのうち、２個は結合手である。］

[Wherein R ^1Z represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a bond. These groups may have a substituent. A plurality of R ^1Z may be the same or different. However, of the plurality of R ^1Z , two are bonds. ]

When R ^1Z is other than a bond, the polymer compound can be easily synthesized. Therefore, R ^1Z is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent A heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, still more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or An aryl group, particularly preferably a hydrogen atom or an aryl group, and these groups optionally have a substituent.
When R ^1Z is other than a bond, the external quantum efficiency of the light-emitting device of the present invention is more excellent. Therefore, R ^1Z is a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent A heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an aryl group, a monovalent heterocyclic group or a substituted amino group, and still more preferably a hydrogen atom, an aryl group or a monovalent heterocyclic group. And particularly preferably a hydrogen atom or an aryl group, and these groups optionally have a substituent.

Examples and preferred ranges of substituents that R ^1Z may have are the same as examples and preferred ranges of substituents that Ar ^Z may further have.

Since the arylene group in Ar ^Z1 and Ar ^Z2 is more excellent in the external quantum efficiency of the light emitting device of the present invention, preferably the formula (A-1) to the formula (A-10), the formula (A-19) or the formula (A -20), more preferably a group represented by formula (A-1) to formula (A-7), formula (A-9) or formula (A-19), Preferred is a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), and particularly preferred is formula (A -1) or a group represented by formula (A-2).

Examples and preferred ranges of the divalent heterocyclic group in Ar ^Z1 and Ar ^Z2 are the same as examples and preferred ranges of the divalent heterocyclic group represented by Ar ^Y1 described later.

Examples and preferred ranges of the substituents that Ar ^Z1 and Ar ^Z2 may have are the same as the examples and preferred ranges of the substituent that Ar ^Z may have. Examples and preferred ranges of the substituents that Ar ^Z1 and Ar ^Z2 may have further include the substituents that Ar ^Z may have further have. Examples of the preferred substituents and the preferred ranges are the same.

Ar ^Z1 and Ar ^Z2 are preferably an arylene group which may have a substituent.

n ^Z1 and n ^Z2 are preferably integers of 0 or more and 3 or less, more preferably 1 or 2, and further preferably 1.

  The structural unit represented by the formula (Z) is preferably a structural unit represented by the formula (ZA) because the external quantum efficiency of the light emitting device of the present invention is more excellent.

［式中、
Ａｒ^Z1、Ａｒ^Z2、ｎ^Z1及びｎ^Z2は、前記と同じ意味を表す。
Ｚ¹は、−Ｃ（Ｒ^3Z）＝で表される基又は−Ｎ＝で表される基を表す。３個存在するＺ¹は、同一でも異なっていてもよい。但し、３個存在するＺ¹のうち、少なくとも１個は−Ｎ＝で表される基である。
Ｒ^2Z及びＲ^3Z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、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。］

[Where:
Ar ^Z1 , Ar ^Z2 , n ^Z1 and n ^Z2 represent the same meaning as described above.
Z ¹ represents a group represented by —C (R ^3Z ) ^═ or a group represented by ^—N═ . Three Z ¹ may be the same or different. However, at least one of the three Z ¹ groups is a group represented by —N═.
R ^2Z and R ^3Z each independently represent a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or halogen atom. These groups may have a substituent. ]

Of the three Z ¹ present, at least two are preferably groups represented by —N═, and more preferably all are groups represented by —N═.

R ^2Z is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, since it facilitates the synthesis of the polymer compound. Is 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 particularly preferably an aryl group. These groups are It may have a substituent.
R ^2Z is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, or a substituted amino group because the external quantum efficiency of the light emitting device of the present invention is more excellent. More preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an aryl group or a monovalent heterocyclic group, particularly preferably an aryl group, and these groups are further It may have a substituent.

R ^3Z is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, A cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, particularly preferably a hydrogen atom, and these groups have a substituent. May be.

Examples and preferred ranges of substituents that R ^2Z and R ^3Z may have are the same as examples and preferred ranges of substituents that Ar ^Z may further have. is there.

  The structural unit represented by the formula (Z-A) is preferably a structural unit represented by the formula (Z-A1) to the formula (Z-A4) because the external quantum efficiency of the light-emitting element of the present invention is more excellent. Yes, more preferably a structural unit represented by the formula (Z-A1) or the formula (Z-A3), and still more preferably a structural unit represented by the formula (Z-A1).

［式中、Ｒ^2Z及びＲ^3Zは前記と同じ意味を表す。］

[Wherein R ^2Z and R ^3Z represent the same meaning as described above. ]

  Examples of the structural unit represented by the formula (Z) include structural units represented by the formula (Z-1) to the formula (Z-46), preferably the formula (Z-1) to the formula (Z -28) or a structural unit represented by formula (Z-40) to formula (Z-46).

［式中、
Ｚ²は、−ＣＨ＝で表される基又は−Ｎ＝で表される基を表す。複数存在するＺ²は、同一でも異なっていてもよい。但し、複数存在するＺ²のうち、少なくとも１個は−Ｎ＝で表される基である。
Ｚ³は、−Ｏ−で表される基又は−Ｓ−で表される基を表す。複数存在するＺ³は、同一でも異なっていてもよい。］

[Where:
Z ² represents a group represented by —CH═ or a group represented by —N═. A plurality of Z ² may be the same or different. However, at least one of a plurality of Z ² is a group represented by —N═.
Z ³ represents a group represented by —O— or a group represented by —S—. A plurality of Z ³ may be the same or different. ]

Among a plurality of Z ² , at least two are preferably groups represented by —N═, and more preferably all are groups represented by —N═.

  Since the structural unit represented by the formula (Z) is more excellent in external quantum efficiency of the light emitting device of the present invention, the total amount of the structural units contained in the polymer compound including the structural unit represented by the formula (Z) On the other hand, it is preferably 0.1 to 50 mol%, more preferably 1 to 30 mol%, still more preferably 5 to 15 mol%.

  In the polymer compound containing the structural unit represented by the formula (Z), the structural unit represented by the formula (Z) may be included alone or in combination of two or more.

  Since the polymer compound containing the structural unit represented by the formula (Z) is more excellent in the external quantum efficiency of the light emitting device of the present invention, the structural unit represented by the following formula (Y) (formula (Z) It is preferable that the structural unit is included. Moreover, since the high molecular compound containing the structural unit represented by Formula (Z) is excellent in hole transport property, it is preferable that the polymer compound further includes a structural unit represented by the following formula (X).

  Since the polymer compound containing the structural unit represented by the formula (Z) has excellent hole transportability and more excellent external quantum efficiency of the light emitting device of the present invention, it is further represented by the formula (X). It is preferable to include a structural unit and a structural unit represented by the formula (Y).

  [Structural Unit Represented by Formula (Y)]

［式中、Ａｒ^Y1は、アリーレン基、２価の複素環基、又は、少なくとも一種のアリーレン基と少なくとも一種の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 groups 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)-(A-10), a formula (A-19) or a formula (A A-20), more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19) These groups may have a substituent.

The divalent heterocyclic group represented by Ar ^Y1 is more preferably a formula (AA-10)-(AA-15), a formula (AA-18)-(AA-21), a formula (AA-33) Or a group represented by formula (AA-34), more preferably represented by formula (AA-10), formula (AA-12), formula (AA-14), or formula (AA-33). These groups may have a substituent.

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

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

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)-(Y-6), and from the viewpoint of the external quantum efficiency of the light emitting device of the present invention. , Preferably a structural unit represented by the formula (Y-1)-(Y-3), and from the viewpoint of hole transportability, preferably represented by the formula (Y-4)-(Y-6). This is a structural unit.

［式中、Ｒ^Y1は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在する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、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y11は、同一でも異なっていてもよい。］

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

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

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

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ₂ — is preferably 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 the formula (Y-A1)-(Y-A5), more preferably a group represented by the 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 optionally 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 the formula (Y-B1)-(Y-B5), more preferably a group represented by the 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及び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及び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及び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、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

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

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

  As the structural unit represented by the formula (Y), for example, a structural unit comprising an arylene group represented by the formula (Y-101)-(Y-121), a formula (Y-201)-(Y-206) A divalent heterocyclic group represented by formula (Y-301), wherein at least one arylene group represented by formula (Y-301) and at least one divalent heterocyclic group are directly bonded to each other. Examples include structural units composed of groups.

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, is superior in the external quantum efficiency of the light-emitting device of the present invention. Therefore, the structural unit represented by the formula (Z) Preferably it is 0.5-99 mol% with respect to the total amount of the structural unit contained in the polymer compound to contain, More preferably, it is 50-95 mol%.

A structural unit represented by the formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group are directly bonded. Since the external quantum efficiency of the light emitting device of the present invention is more excellent, the structural unit that is a group of Is 0.5 to 30 mol%, more preferably 3 to 20 mol%.

  In the polymer compound containing the structural unit represented by the formula (Z), only one type of structural unit represented by the formula (Y) may be contained, or two or more types may be contained.

  [Structural Unit Represented by Formula (X)]

［式中、
ａ^X1及びａ^X2は、それぞれ独立に、０以上の整数を表す。
Ａｒ^X1及びＡｒ^X3は、それぞれ独立に、アリーレン基又は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及びＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2及びＡｒ^X4が複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^X1、Ｒ^X2及び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、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^X2及びＲ^X3が複数存在する場合、それらは同一でも異なっていてもよい。］

[Where:
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. And these groups may have a substituent. When there are a plurality of Ar ^X2 and Ar ^X4 , they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are a plurality of R ^X2 and R ^X3 , they may be the same or different. ]

a ^X1 is preferably 2 or less, more preferably 1 because the external quantum efficiency of the light emitting device of the present invention is excellent.

a ^X2 is preferably 2 or less, more preferably 0, because the external quantum efficiency of the light emitting device 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 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 the formula (AA-1), the formula (AA-2), or the formula (AA-7)-(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)-(A-11) Or it is group represented by a formula (A-19), and these groups may 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 kind of arylene group represented by Ar ^X2 and Ar ^X4 and at least one kind of divalent heterocyclic group are directly bonded. Further preferable ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 , respectively.

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 is 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 formula (X-1)-(X-7), more preferably the formula (X-1)-(X-6) And more preferably a structural unit represented by the formula (X-3)-(X-6).

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

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

  Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1% relative to the total amount of the structural units contained in the polymer compound including the structural unit represented by the formula (Z). It is -50 mol%, More preferably, it is 1-40 mol%, More preferably, it is 5-30 mol%.

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

  In the polymer compound containing the structural unit represented by the formula (Z), the structural unit represented by the formula (X) may be contained alone or in combination of two or more.

[Examples of polymer compounds]
Examples of the polymer compound containing the structural unit represented by the formula (Z) include polymer compounds (P-1) to (P-8). Here, the “other” structural unit means a structural unit other than the structural unit represented by the formula (Z), the structural unit represented by the formula (Y), and the structural unit represented by the formula (X). To do.

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

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

  The polymer compound containing the structural unit represented by the formula (Z) may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and other embodiments. However, it is preferably a copolymer.

The number average molecular weight in terms of polystyrene of the polymer compound containing the structural unit represented by the formula (Z) is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ^{4 to} 5 × 10 ^5. And more preferably 3 × 10 ^{4 to} 1.5 × 10 ⁵ .

[Production method]
Examples of the polymer compound containing the structural unit represented by the formula (Z) include Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), International Publication No. 1998/011150, International Manufactured by using a known polymerization method described in JP 2013/200988 A, JP 2012-036388 A, JP 2014-148663 A, JP 2010-196040 A, JP 2010-260879 A, and the like. In other words, for example, it can be produced by using a polymerization method such as a coupling reaction using a transition metal catalyst such as a Suzuki reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction. .

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

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

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

<Compound represented by Formula (1)>
Examples of the aromatic hydrocarbon group represented by Ar ¹ include a monocyclic aromatic hydrocarbon group and a condensed ring aromatic hydrocarbon group, and a condensed ring aromatic hydrocarbon group is preferable. These groups may have a substituent.

In Ar ¹ , the number of carbon atoms of the monocyclic aromatic hydrocarbon group is preferably 6, not including the number of carbon atoms of the substituent.

The monocyclic aromatic hydrocarbon group in Ar ¹ is preferably a group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the benzene ring, and the group has a substituent. It may be.

In Ar ¹ , the number of carbon atoms of the aromatic hydrocarbon group of the condensed ring is usually 7 to 60, preferably 9 to 30 and more preferably 10 to 20 without including the number of carbon atoms of the substituent. It is.

Examples of the aromatic hydrocarbon group of the condensed ring in Ar ¹ include a naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, indene ring, pyrene ring, perylene ring, chrysene And a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a ring or a ring obtained by condensing these rings, preferably naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene A ring, a fluorene ring, a spirobifluorene ring, an indene ring, a pyrene ring, a chrysene ring, or a group in which one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring are removed from these condensed rings More preferably, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring or A group obtained by removing one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the pyrobifluorene ring, and more preferably directly bonded to the carbon atoms constituting the ring from the fluorene ring or the spirobifluorene ring. A group in which one or more hydrogen atoms are removed, particularly preferably a group in which one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring are removed from the fluorene ring, and these groups have substituents. You may have.

In Ar ¹ , the number of carbon atoms of the monocyclic heterocyclic group does not include the number of carbon atoms of the substituent, and is preferably 2 to 5, and more preferably 3 to 5.

Examples of the monocyclic heterocyclic group in Ar ¹ include a pyrrole ring, a diazole ring, a triazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring. , A pyridine ring, a diazabenzene ring and a triazine ring, a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring, and preferably a pyridine ring, a diazabenzene ring and a triazine ring, A group in which one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring are removed, and more preferably one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from a triazine ring These are the groups except for the above, and these groups may have a substituent.

In Ar ¹ , the number of carbon atoms of the heterocyclic group of the condensed ring does not include the number of carbon atoms of the substituent, and is usually 3 to 60, preferably 5 to 30, and more preferably 7 to 20 It is.

Examples of the heterocyclic group of the condensed ring in Ar ¹ include, for example, a benzoxazole ring, a benzisoxazole ring, a benzothiazole ring, a benzoisothiazole ring, a benzoxiadiazole ring, a benzothiadiazole ring, an azanaphthalene ring, and a diazanaphthalene ring , Triazanaphthalene ring, azaanthracene ring, diazaanthracene ring, triazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, benzofuran Ring, dibenzofuran ring, benzothiophene ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring, acridone ring, 5,10-dihydrophenazine ring, or a combination thereof. And a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a ring in which an aromatic ring is condensed, preferably an indole ring, a carbazole ring, an azacarbazole ring, a dia Zacarbazole ring, benzofuran ring, dibenzofuran ring, benzothiophene ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring, acridone ring, 5,10-dihydrophenazine ring, or these rings A group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a condensed ring, and more preferably a carbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring 9,10-dihydroacridine ring or 5,10-dihydride It is a group obtained by removing one or more hydrogen atoms directly bonded to a carbon atom or hetero atom constituting a ring from a lophenazine ring, and more preferably a carbon atom constituting a ring from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring. Or it is the group except one or more hydrogen atoms couple | bonded directly with a hetero atom, and these groups may have a substituent.

Examples and preferred ranges of the substituent that Ar ¹ may have are the same as examples and preferred ranges of the substituent that Ar ^Z may have.

When there are a plurality of substituents that Ar ¹ may have, it is preferable that they are bonded to each other and do not form a ring with the atoms to which they are bonded.

Examples of the substituent that the substituent that Ar ¹ may have and the substituent that the substituent that Ar ^Z may have further may include examples of the substituent that Ar ^Z may further have. Same as example and preferred range.

Ar ¹ is preferably a monocyclic aromatic hydrocarbon group, a condensed aromatic hydrocarbon group or a condensed heterocyclic group, more preferably, since the external quantum efficiency of the light emitting device of the present invention is more excellent. Is a condensed ring aromatic hydrocarbon group or a condensed ring heterocyclic group, and more preferably a condensed ring aromatic hydrocarbon group, and these groups optionally have a substituent.

n ¹ is preferably an integer of 1 or more, 3 or less, more preferably 1 or 2, and even more preferably 2, because the synthesis of the compound represented by formula (1) becomes easy.

n ² is preferably an integer of 0 or more and 3 or less, more preferably 0 or 1, and still more preferably 0, since the synthesis of the compound represented by the formula (1) becomes easy.

Examples of the arylene group and the preferable range of the Ar ² is the same as the examples of the arylene group and the preferable range of the Ar ^Z1 and Ar ^Z2. Examples of the divalent heterocyclic group for Ar ² and preferred ranges are the same as examples and preferred ranges of the divalent heterocyclic group for Ar ^Z1 and Ar ^Z2.

Examples and preferred ranges of substituents that Ar ² may have are the same as examples and preferred ranges of substituents that Ar ^Z may have.

Examples of the substituent that the substituent that Ar ² may have and the substituent that Ar ^Z may further have are as follows. Same as example and preferred range.

R ¹ and R ² are preferably an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, more preferably an aryl group or a monovalent group, because the external quantum efficiency of the light emitting device of the present invention is more excellent. And more preferably an aryl group, and these groups optionally have a substituent.

The aryl group in R ¹ and R ² is preferably a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group or a spirobifluorenyl group, more preferably a phenyl group. , A naphthyl group, a phenanthrenyl group or a fluorenyl group, more preferably a phenyl group, and these groups optionally have a substituent.

The monovalent heterocyclic group in R ¹ and R ² is preferably a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a dibenzofuran ring, 2 of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring from a dibenzothiophene ring, a phenoxazine ring, a phenothiazine ring, a 9,10-dihydroacridine ring, or a 5,10-dihydrophenazine ring A monovalent group excluding one hydrogen atom, more preferably a carbon constituting a ring from a pyridine ring, a diazabenzene ring, a triazine ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, a phenoxazine ring or a phenothiazine ring. Of hydrogen atoms directly bonded to atoms or heteroatoms A monovalent group excluding two hydrogen atoms, more preferably 2 of hydrogen atoms directly bonded from a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring to a carbon atom or a hetero atom constituting the ring. A monovalent group in which two hydrogen atoms are removed, and particularly preferably a monovalent group in which two hydrogen atoms out of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the ring are removed from a carbazole ring. These groups may have a substituent.

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

Examples of the substituent that the substituent which may be possessed by R ¹ and R ² may further have and the preferred range thereof may further be possessed by the substituent which Ar ^Z may have. It is the same as the example and preferable range of a substituent.

Examples of the “divalent group” include an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R ^ZT1 ) —, a group represented by —O—, and And a group represented by -S-, preferably an alkylene group, a cycloalkylene group, a group represented by -N (R ^ZT1 )-, a group represented by -O-, or -S-. More preferably, it is an alkylene group, a group represented by —N (R ^ZT1 ) —, a group represented by —O— or a group represented by —S—, and more preferably — A group represented by O— or a group represented by —S—, and these groups optionally have a substituent. R ^ZT1 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.

Examples and preferred ranges of the substituent that the divalent group may have are the same as examples and preferred ranges of the substituent that Ar ^Z may have.

Examples and preferred ranges of substituents that the divalent group may have further include substituents that the substituent that Ar ^Z may have further may have. Examples of groups are the same as the preferred ranges.

The number of carbon atoms of the alkylene group in the divalent group is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10, not including the number of carbon atoms of the substituent. The number of carbon atoms of the cycloalkylene group in the divalent group is usually 3 to 20 without including the number of carbon atoms of the substituent.
The alkylene group and cycloalkylene group in the divalent group may have a substituent, for example, methylene group, ethylene group, propylene group, butylene group, hexylene group, cyclohexylene group, octylene group, and these And a group in which the hydrogen atom is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a fluorine atom, or the like.

Examples and preferred ranges of the arylene group in the divalent group are the same as examples and preferred ranges of the arylene group in Ar ^Z1 and Ar ^Z2 . Examples and preferred ranges of the divalent heterocyclic group in the divalent group are the same as examples and preferred ranges of the divalent heterocyclic group in Ar ^Z1 and Ar ^Z2 .

R ^ZT1 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. These groups may have a substituent.
Examples and preferred ranges of the substituent that R ^ZT1 may have are the same as examples and preferred ranges of the substituent that Ar ^Z may further have.

Since the synthesis of the compound represented by the formula (1) is facilitated, Ar ² , R ¹ and R ² are each directly linked to a group other than the group bonded to the nitrogen atom to which the group is bonded. It is preferable not to form a ring by bonding or bonding through a divalent group.

Since the external quantum efficiency of the light-emitting device of the present invention is more excellent, R ¹ and R ² are preferably bonded directly or bonded via a divalent group to form a ring.
When R ¹ and R ² are directly bonded or bonded via a divalent group to form a ring, the monovalent complex represented by (R ¹ ) (R ² ) N— The number of carbon atoms of the ring group is usually 5 to 60, preferably 7 to 30, and more preferably 10 to 20 without including the number of carbon atoms of the substituent.
When R ¹ and R ² are directly bonded or bonded via a divalent group to form a ring, the monovalent complex represented by (R ¹ ) (R ² ) N— Examples of the ring group include an azole ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring, 5,10-dihydrophenazine ring, and the like. A ring in which 1 to 5 aromatic rings are condensed to the ring, or a group in which one hydrogen atom directly bonded to the nitrogen atom constituting the ring is removed from the ring in which these rings are condensed, This group may have a substituent.
In a ring condensed with an aromatic ring, the number of carbon atoms of the aromatic ring is usually 3 to 60, preferably 4 to 30, and more preferably 6 to 15 excluding the number of carbon atoms of the substituent. It is. In the ring condensed with an aromatic ring, examples of the aromatic ring include benzene ring, naphthalene ring, indene ring, fluorene ring, dihydrophenanthrene ring, spirobifluorene ring, pyridine ring, diazabenzene ring, triazine ring, indole ring, carbazole ring. Benzofuran ring, dibenzofuran ring, benzothiophene ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring and 5,10-dihydrophenazine ring, preferably benzene ring, indene ring, Fluorene ring, indole ring, carbazole ring, benzofuran ring, dibenzofuran ring, benzothiophene ring or dibenzothiophene ring, more preferably benzene ring, indene ring, indole ring, benzofuran ring or benzothiophene , And still more preferably, a benzene ring, indene ring or indole ring, these rings may have a substituent.
When R ¹ and R ² are directly bonded or bonded via a divalent group to form a ring, the monovalent complex represented by (R ¹ ) (R ² ) N— The ring group is preferably a nitrogen atom constituting a ring from a carbazole ring, indenocarbazole ring, indolocarbazole ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring or 5,10-dihydrophenazine ring. A hydrogen atom 1 directly bonded to a nitrogen atom constituting the ring from a carbazole ring, an indenocarbazole ring, an indolocarbazole ring or a phenoxazine ring. These rings are groups other than those, and these rings may have a substituent.

  The compound represented by the formula (1) is preferably a compound represented by the formula (1-1) because the external quantum efficiency of the light emitting device of the present invention is more excellent.

［式中、Ａｒ¹、ｎ²、Ａｒ²、Ｒ¹及びＲ²は、前記と同じ意味を表す。
Ｘ¹は、−Ｃ(Ｒ⁴)₂−、−Ｃ(Ｒ⁴)＝Ｃ(Ｒ⁴)−、−Ｃ(Ｒ⁴)₂−Ｃ(Ｒ⁴)₂−、−Ｏ−、−Ｓ−、又は、−Ｎ(Ｒ⁵)−で表される基を表す。
Ｒ³、Ｒ⁴及びＲ⁵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、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。Ｒ³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炭素原子とともに環を形成していてもよい。複数存在するＲ⁴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。
ｎ¹'は１以上５以下の整数を表し、ｎ³は１以上７以下の整数を表す。但し、ｎ¹'＋ｎ³は８である。］

[Wherein, Ar ¹ , n ² , Ar ² , R ¹ and R ² represent the same meaning as described above.
X ¹ represents —C (R ⁴ ) ₂ —, —C (R ⁴ ) ═C (R ⁴ ) —, —C (R ⁴ ) ₂ —C (R ⁴ ) ₂ —, —O—, —S—. Or a group represented by —N (R ⁵ ) —.
R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or halogen Represents an atom, and these groups optionally have a substituent. When a plurality of R ³ are present, they may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded. A plurality of R ⁴ 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.
n ¹ ′ represents an integer of 1 to 5, and n ³ represents an integer of 1 to 7. However, n ¹ '+ n ³ is 8. ]

R ³ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more 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 particularly preferably a hydrogen atom, an alkyl group or a cycloalkyl group. Particularly preferred is a hydrogen atom, and these groups optionally have a substituent.

When two or more R < ³ > exists, it is preferable that it mutually couple | bonds and does not form a ring with the carbon atom which each couple | bonds.

X ¹ is preferably -C (R ⁴ ) _2- , -C (R ⁴ ) = C (R ⁴ )-or -C (R ⁴ ) ₂ because the external quantum efficiency of the light emitting device of the present invention is excellent. A group represented by —C (R ⁴ ) ₂ —, more preferably a group represented by —C (R ⁴ ) ₂ — or —C (R ⁴ ) ₂ —C (R ⁴ ) ₂ —. And more preferably a group represented by —C (R ⁴ ) ₂ —.

R ⁴ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, A cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or It is an aryl group, and these groups may have a substituent.

In X ^1, -C (R ⁴⁾ ₂ - group and -C represented by ^{(R 4) = C (R} 4) - a combination of in the group represented by the two R ⁴ is preferably Both are alkyl groups or cycloalkyl groups, both are aryl groups, both are monovalent heterocyclic groups, or one is an alkyl group or cycloalkyl group and the other is an aryl group or monovalent heterocyclic group, more preferably Are both an alkyl group or a cycloalkyl group, both are an aryl group, or one is an alkyl group or a cycloalkyl group and the other is an aryl group, and more preferably both are an alkyl group or a cycloalkyl group, or one Is an alkyl group or a cycloalkyl group and the other is an aryl group, and particularly preferably, one is an alkyl group or a cycloalkyl group and the other is an aryl group. It may have a substituent. -C (R ⁴⁾ ₂ - when two R ⁴ in the group represented to form a ring, -C (R ⁴⁾ ₂ - Examples of the group represented by, preferably the formula (Y-A1 ) -A group represented by the formula (Y-A5), more preferably a group represented by the formula (Y-A4), and these groups each optionally have a substituent.

In X ¹ , at least one of four R ⁴ groups represented by —C (R ⁴ ) ₂ —C (R ⁴ ) ₂ — represents an alkyl group, a cycloalkyl group, an aryl group, or 1 Preferably, all four are alkyl groups, cycloalkyl groups, aryl groups or monovalent heterocyclic groups, and all four are alkyl groups, cycloalkyl groups or aryl. It is more preferable that all four groups are alkyl groups or cycloalkyl groups, and these groups may have a substituent. _{^{C (R 4) 2 -C (}} R 4) 2 - If in the group represented by R ⁴ to form a _{^{ring, -C (R Y2) 2 -C}} (R Y2) 2 - , a group represented by Is preferably a group represented by the formula (Y-B1) -formula (Y-B5), more preferably a group represented by the formula (Y-B3), and these groups have a substituent. You may do it.

R ⁵ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. And more preferably an aryl group or a monovalent heterocyclic group, particularly preferably an aryl group, and these groups optionally have a substituent.

Examples and preferred ranges of substituents that R ³ , R ⁴ and R ⁵ may have are examples and preferred ranges of substituents that Ar ^Z may further have. Is the same.

n ¹ ′ is preferably an integer of 1 or more, 3 or less, more preferably 1 or 2, and even more preferably 2, because the synthesis of the compound represented by Formula (1-1) is facilitated. .

As a compound represented by Formula (1), the compound represented by a following formula is mentioned. In the following formula, Z ³ represents the same meaning as described above.

  The compound represented by formula (1) can be obtained from Aldrich, Luminescence Technology Corp. , AK Scientific, etc. In addition, for example, International Publication No. 2005/049546, International Publication No. 2013/108022, International Publication No. 2006/030527, International Publication No. 2006/025273, International Publication No. 2005/104264, International Publication No. 2012. / 0866668, International Publication No. 2014/157016, and JP2013-256655A.

<Phosphorescent compound>
“Phosphorescent compound” generally means a compound that exhibits phosphorescence at room temperature (25 ° C.), and is preferably a metal complex that emits light from a triplet excited state at room temperature. This metal complex that emits light from a triplet excited state has a central metal atom and a ligand.

  Examples of the central metal atom include a metal atom having an atomic number of 40 or more, a complex having a spin-orbit interaction, and capable of causing an intersystem crossing between a singlet state and a triplet state. Examples of the metal atom include a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, and a platinum atom. Since the external quantum efficiency of the light emitting device of the present invention is excellent, an iridium atom or a platinum atom is preferable.

  As the ligand, for example, 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 anionic polydentate ligands may be mentioned. 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.

[Metal Complex Represented by Formula (M)]
The phosphorescent compound is preferably a metal complex represented by the formula (M).

M ¹ is preferably an iridium atom because the external quantum efficiency of the light emitting device of the present invention is more excellent.
When M ¹ is an iridium atom, n ^M1 is preferably 2 or 3, and more preferably 3.
When M ¹ is a platinum atom, n ^M1 is preferably 2.
E ¹ and E ² are preferably carbon atoms.

Ring R ^M1 is preferably a 5-membered or 6-membered aromatic heterocyclic ring having 1 to 4 nitrogen atoms as ring constituent atoms, such as a pyridine ring, diazabenzene ring, triazine ring, quinoline ring, isoquinoline ring. , A diazole ring or a triazole ring, more preferably a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, an imidazole ring or a triazole ring, and particularly preferably a pyridine ring, a quinoline ring or an isoquinoline ring. A pyridine ring is particularly preferable, and these rings may have a substituent.

Ring R ^M2 is preferably a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and is a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, It is more preferably a diazabenzene ring, triazine ring, pyrrole ring, furan ring or thiophene ring, more preferably a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring or diazabenzene ring, benzene ring, pyridine ring Or it is especially preferable that it is a pyrimidine ring, and it is especially preferable that it is a benzene ring, and these rings may have a substituent.

Examples of the substituent that the ring R ^M1 and the ring R ^M2 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group-substituted amino group, or A halogen atom is preferable, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferable, and an alkyl group, a cycloalkyl group, an aryl group or a monovalent complex is preferable. A cyclic group is more preferred, an alkyl group or an aryl group is particularly preferred, an aryl group is particularly preferred, and these groups may further have a substituent.

Examples of the substituent that the ring R ^M1 and the ring R ^M2 may have further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and a monovalent complex. A cyclic group or a substituted amino group is preferred, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group is more preferred, an alkyl group or a cycloalkyl group is further preferred, and these groups may further have a substituent. .

The substituent that the ring R ^M1 may have and the substituent that the ring R ^M2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded. Is preferably not formed.

The aryl group, monovalent heterocyclic group or substituted amino group in the substituent that the ring R ^M1 and the ring R ^M2 may have is preferably a compound of the formula because the external quantum efficiency of the light emitting device of the present invention is more excellent. It is a group represented by (DA), formula (DB) or formula (DC), more preferably a group represented by formula (DA).

［式中、
ｍ^DA1、ｍ^DA2及び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、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^DA1、Ａｒ^DA2及びＡｒ^DA3は、それぞれ独立に、アリーレン基又は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及び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、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数ある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 may have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

［式中、
ｍ^DA1、ｍ^DA2、ｍ^DA3、ｍ^DA4、ｍ^DA5、ｍ^DA6及び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、芳香族炭化水素基又は複素環基を表し、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及びＡｒ^DA7は、それぞれ独立に、アリーレン基又は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及び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、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数ある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 may have a substituent. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

［式中、
ｍ^DA1は、０以上の整数を表す。
Ａｒ^DA1は、アリーレン基又は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が複数ある場合、それらは同一でも異なっていてもよい。
Ｔ^DAは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[Where:
m ^DA1 represents an integer of 0 or more.
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^{DA1 s} , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]

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

G ^DA is preferably a group represented by the formula (GDA-11) ~ formula (GDA-15), more preferably a group represented by the formula (GDA-11) ~ formula (GDA-14) More preferred is a group represented by the formula (GDA-11) or (GDA-14), and particularly preferred is a group represented by the formula (GDA-11).

［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、又は、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、又は、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、又は、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、アリール基又は１価の複素環基を表し、これらの基は更に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), Ar in formula (DB) ^DA4, or represents a bond between Ar ^DA6 in the formula (DB).
*** is, Ar ^DA3 in the formula (DA), Ar ^DA3 in the formula (DB), Ar in formula (DB) ^DA5, or 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 further have a substituent. When there are a plurality of ^RDA , they may be the same or different. ]

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

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably a phenylene group, a ^fluorenediyl group or a carbazolediyl group, more preferably a formula (A-1) to a formula (A-3), Formula (A-8), Formula (A-9), Formula (AA-10), Formula (AA-11), Formula (AA-33) or Formula (AA-34) More preferably a group represented by formula (ArDA-1) to formula (ArDA-5), particularly preferably a group represented by formula (ArDA-1) to formula (ArDA-3). And particularly preferably a group represented by the formula (ArDA-1) or the formula (ArDA-2), and these groups optionally have a substituent.

［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、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。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, still more preferably an aryl group, The group may have a substituent.

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

［式中、Ｒ^DA及び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 group represented by formula (DA) is preferably a group represented by formula (D-A1) to formula (D-A3), more preferably a group represented by formula (D-A1). .

［式中、
Ｒ^p1、Ｒ^p2及び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又はハロゲン原子を表す。Ｒ^p1及びＲ^p2が複数存在する場合、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又は１を表す。複数存在するｎｐ１は、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 a plurality of R ^p1 and R ^p2 are present, 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 (DB) is preferably a group represented by the formula (D-B1) to the formula (D-B3), more preferably a group represented by the formula (D-B1). .

［式中、
Ｒ^p1、Ｒ^p2及び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又はハロゲン原子を表す。Ｒ^p1及びＲ^p2が複数存在する場合、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又は１を表す。複数存在するｎｐ１及びｎｐ２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 a plurality of R ^p1 and R ^p2 are present, 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 and np2 may be the same or different. ]

  The group represented by the formula (DC) is preferably a group represented by the formula (D-C1) to the formula (D-C4), more preferably the formula (D-C1) to the formula (D-C3). More preferably a group represented by the formula (D-C1) or the formula (D-C2), particularly preferably a group represented by the formula (D-C1).

［式中、
Ｒ^p4及びＲ^p5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又はハロゲン原子を表す。Ｒ^p4及びＲ^p5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。
ｎｐ４は、０〜５の整数を表し、ｎｐ５は、０〜４の整数を表す。］

[Where:
R ^p4 and R ^p5 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 ^p4 and R ^p5 , they may be the same or different.
np4 represents an integer of 0 to 5, and np5 represents an integer of 0 to 4. ]

  np1 is preferably 0 or 1, more preferably 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0. np4 is preferably 0-2. np5 is preferably 0 to 2, and more preferably 0.

R ^p1 , R ^p2 , R ^p3 , R ^p4 and R ^p5 are preferably an alkyl group or a cycloalkyl group.

  As group represented by a formula (DA), group represented by a formula (DA-1)-a formula (DA-12) is mentioned, for example.

［式中、Ｒ^Dは、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、ヘキシル基、２−エチルヘキシル基、ｔｅｒｔ−オクチル基、シクロヘキシル基、メトキシ基、２−エチルヘキシルオキシ基又はシクロへキシルオキシ基を表す。複数存在するＲ^Dは、それぞれ同一でも異なっていてもよい。］

[Wherein, R ^D represents a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group. Represents a group. A plurality of R ^D may be the same or different. ]

  Examples of the group represented by the formula (D-B) include groups represented by the formula (D-B-1) to the formula (D-B-4).

［式中、Ｒ^Dは前記と同じ意味を表す。］

[Wherein, R ^D represents the same meaning as described above. ]

  Examples of the group represented by the formula (D-C) include groups represented by the formula (D-C-1) to the formula (D-C-13).

［式中、Ｒ^Dは前記と同じ意味を表す。］

[Wherein, R ^D represents the same meaning as described above. ]

^RD is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group, and more preferably a tert-butyl group.

Since at least one ring selected from the group consisting of ring R ^M1 and ring R ^M2 is excellent in solubility, it preferably has a substituent.

The substituent which at least one ring selected from the group consisting of ring R ^M1 and ring R ^M2 preferably has an alkyl group, a cycloalkyl group, or formula (DA) to formula (DC). And more preferably an alkyl group or a group represented by formula (DA) to formula (DC), and more preferably a formula (DA) to formula ( DC), particularly preferably a group represented by the formula (DA), and these groups may have a substituent.

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

［式中、＊は、Ｍ¹と結合する部位を表す。］

Wherein * represents a site that binds to M ^1. ]

  The metal complex represented by the formula (M) is preferably a metal complex represented by the formula Ir-1 to the formula Ir-5, more preferably a metal complex represented by the formula Ir-1 to the formula Ir-3, A metal complex represented by formula Ir-1 or formula Ir-2 is more preferred, and a metal complex represented by formula Ir-1 is particularly preferred.

At least one of R ^{D1 to} R ^D8 in the metal complex represented by the formula Ir-1, at least one of R ^{D11 to} R ^D20 in the metal complex represented by the formula Ir-2, represented by the formula Ir-3 At least one of R ^{D1 to} R ^D8 and R ^{D11 to} R ^{D20 in} the metal complex, at least one of R ^{21 to} R ^D26 in the metal complex represented by the formula Ir-4, and represented by the formula Ir-5 At least one of R ^{D31 to} R ^D37 in the metal complex is preferably an alkyl group, a cycloalkyl group, or a group represented by the formula (DA) to the formula (DC), respectively. Preferably, it is an alkyl group or a group represented by the formula (DA) to the formula (DC), and more preferably represented by the formula (DA) to the formula (DC). Group, particularly preferably a group represented by the formula (DA), and these groups optionally have a substituent.

R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36, and R ^D37 are the light emitting elements of the present invention. Since the external quantum efficiency is more excellent, preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably , A hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and more preferably a hydrogen atom, an alkyl group, or a formula (DA) to a formula (D- C), particularly preferably a hydrogen atom, or formula (DA) to formula ( DC), and these groups may have a substituent.

R ^D22 and R ^D33 are preferably represented by an alkyl group, a cycloalkyl group, or a formula (D-A) to a formula (D-C) because the external quantum efficiency of the light-emitting element of the present invention is more excellent. A group represented by formula (DA) to formula (DC), more preferably a group represented by formula (DC), and these groups are: It may have a substituent.

R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 may have a substitution Examples of groups and preferred ranges are the same as examples and preferred ranges of substituents that the ring R ^M1 and ring R ^M2 may further have.

R ^D1 and R ^D2 , R ^D2 and R ^D3 , R ^D3 and R ^D4 , R ^D4 and R ^D5 , R ^D5 and R ^D6 , R ^D6 and R ^D7 , R ^D7 and R ^D8 , R ^D11 and R ^D12 , R ^D12 And R ^D13 , R ^D13 and R ^D14 , R ^D14 and R ^D15 , R ^D15 and R ^D16 , R ^D16 and R ^D17 , R ^D17 and R ^D18 , R ^D18 and R ^D19 , R ^D19 and R ^D20 , R ^D22 and R ^D23 , R ^D23 and R ^D24 , R ^D24 and R ^D25 , R ^D25 and R ^D26 , R ^D31 and R ^D32 , R ^D32 and R ^D33 , R ^D33 and R ^D34 , R ^D34 and R ^D35 , R ^D35 and R ^D36 , R ^D36 and R ^D37 are preferably bonded to each other and do not form a ring with the atoms to which they are bonded.

  The metal complex represented by the formula Ir-1 is preferably a metal complex represented by the formula Ir-11 to Ir-13. The metal complex represented by the formula Ir-2 is preferably a metal complex represented by the formula Ir-21. The metal complex represented by the formula Ir-3 is preferably a metal complex represented by the formula Ir-31 to the formula Ir-33. The metal complex represented by the formula Ir-4 is preferably a metal complex represented by the formula Ir-41 to the formula Ir-43. The metal complex represented by the formula Ir-5 is preferably a metal complex represented by the formula Ir-51 to the formula Ir-53.

［式中、
ｎ_D2は、１又は２を表す。
Ｄは、式(D-A)〜式(D-C)で表される基を表す。複数存在するＤは、同一でも異なっていてもよい。
Ｒ^DCは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^DCは、同一でも異なっていてもよい。
Ｒ^DDは、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^DDは、同一でも異なっていてもよい。］

[Where:
n _D2 represents 1 or 2.
D represents a group represented by formula (DA) to formula (DC). A plurality of D may be the same or different.
R ^DC 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. A plurality of R ^DCs may be the same or different.
R ^DD represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of R ^DD may be the same or different. ]

  Examples of the phosphorescent compound include the metal complexes shown below.

Phosphorescent compounds are available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source.
In addition, Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985), Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984), International Publication No. 2011/024761, International Publication No. 2002/44189, Japanese Patent Application Laid-Open No. 2006-188673, and the like.

<Content of each component, etc.>
In the composition of the present invention, the content of the phosphorescent compound is the sum of the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and the phosphorescent compound. When it is 100 parts by mass, it is usually 0.01 to 95 parts by mass, preferably 0.1 to 80 parts by mass, more preferably 1 to 75 parts by mass, still more preferably 5 to 50 parts by mass, Especially preferably, it is 20-40 mass parts.

  In the composition of the present invention, the content of the compound represented by the formula (1) is such that the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and phosphorescence. When the total with the compound is 100 parts by mass, it is usually 0.01 to 95 parts by mass, preferably 0.05 to 50 parts by mass, more preferably 0.1 to 30 parts by mass, and further preferably 1 to 10 parts. Part by mass.

  In the composition of the present invention, the polymer compound containing the structural unit represented by formula (Z), the compound represented by formula (1), and the phosphorescent compound may each be used alone or in combination. More than one species may be used in combination.

The lowest excited triplet state (T ₁ ) possessed by the polymer compound containing the structural unit represented by formula (Z) and T ₁ possessed by the compound represented by formula (1) are determined using the composition of the present invention. Since the external quantum efficiency of the obtained light-emitting element is excellent, it is preferable that the phosphorescent compound has an energy level equivalent to T ₁ or higher energy level.

  Since the polymer compound containing the structural unit represented by the formula (Z) and the compound represented by the formula (1) can produce a light-emitting element obtained using the composition of the present invention by a solution coating process, phosphorescence emission It is preferable that the compound exhibits solubility in a solvent capable of dissolving the active compound.

<Others>
The composition of the present invention may further contain at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. . However, the light-emitting material, the hole transport material, the hole injection material, the electron transport material, and the electron injection material are represented by the polymer compound including the structural unit represented by the formula (Z) and the formula (1). Different from the compound and the phosphorescent compound.

The composition of the present invention may further contain a solvent.
A composition containing a polymer compound containing a structural unit represented by formula (Z), a compound represented by formula (1), a phosphorescent compound, and a solvent (hereinafter 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.

  In the ink, when the total amount of the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and the phosphorescent compound is 100 parts by mass, Usually, it is 1000-100,000 mass parts, Preferably it is 2000-20000 mass parts.

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

[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, and trinitrofluorenone, and fullerene is preferable.

  In the composition of the present invention, the compounding amount of the hole transport material is the sum of the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and the phosphorescent compound. When it is 100 mass parts, it is 0.1-1000 mass parts normally, Preferably it is 1-400 mass parts, More preferably, it is 5-150 mass parts.

  In the composition of the present invention, the hole transport material may be used alone or in combination of two or more.

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

  Examples of the low molecular compound include a metal complex having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and , Diphenoquinone, and derivatives thereof.

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

  In the composition of the present invention, the amount of the electron transporting material is 100 in total of the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and the phosphorescent compound. When it is set as a mass part, it is 0.1-1000 mass parts normally, Preferably it is 1-400 mass parts, More preferably, it is 5-150 mass parts.

  In the composition of the present invention, the electron transport material may be used alone or in combination of two or more.

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

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

  Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline, and polyquinoxaline, and derivatives thereof; polymers containing an aromatic amine structure in the main chain or side chain, etc. The conductive polymer is mentioned.

  In the composition of the present invention, the compounding amounts of the hole injecting material and the electron injecting material are respectively a polymer compound containing a structural unit represented by the formula (Z), a compound represented by the formula (1), and phosphorescence. When a total with an ionic compound is 100 mass parts, it is 0.1-1000 mass parts normally, Preferably it is 1-400 mass parts, More preferably, it is 5-150 mass parts.

  In the composition of the present invention, 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 contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × 10 ⁻⁵ S / cm to 1 × 10 ³ S / cm. In order to 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.

[Luminescent material]
Luminescent materials (different from phosphorescent compounds) are classified into low molecular compounds and high molecular compounds. The light emitting material may have a crosslinking group.

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

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

  In the composition of the present invention, the content of the luminescent material is 100 masses of the total of the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and the phosphorescent compound. Parts, it is usually 0.1 to 1000 parts by mass, preferably 0.1 to 400 parts by mass.

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

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the 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 100 in total of the polymer compound containing the structural unit represented by the formula (Z), the compound represented by the formula (1), and the phosphorescent compound. When it is made into a mass part, it is 0.001-10 mass parts normally.

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

<Membrane>
The membrane contains the composition of the present invention.

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

  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 containing the composition of the present invention.
As a structure of the light emitting element of this invention, it has the electrode which consists of an anode and a cathode, for example, and the layer containing the composition of this invention provided between this electrode.

[Layer structure]
The layer containing the composition 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, and is preferably a light emitting layer. 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 device 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.

  Examples of the material of the hole transport layer, the electron transport layer, the light emitting layer, the hole injection layer, and the electron injection layer include, for example, the above-described hole transport material, electron transport material, and light emitting material, in addition to the composition of the present invention. , 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 film formation from a solution or a molten state may be used.

  The order, number, and thickness of the layers to be laminated are adjusted in consideration of the external quantum efficiency and the luminance 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 at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.
Each of the anode and the cathode may have a laminated structure of two or more layers.

[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 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 the examples, the polystyrene-equivalent number average molecular weight (Mn) and polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound were determined by the following size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. . The SEC measurement conditions are as follows.

  The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. The mobile phase was run at a flow rate of 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.

LC-MS was measured by the following method.
The measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (manufactured by Agilent, trade name: 1100LCMSD). The LC-MS mobile phase 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 was measured by the following method.
About 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N, N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol. Alternatively, it was dissolved in methylene chloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300).

  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 UV = 254 nm in HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so that the concentration was 0.01 to 0.2% by mass, and 1 to 10 μL was injected into the HPLC depending on the concentration. The HPLC mobile phase was used by changing the ratio of acetonitrile / tetrahydrofuran from 100/0 to 0/100 (volume ratio) and flowing at a flow rate of 1.0 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.

<Compounds M1 to M21> Synthesis and Acquisition of Compounds M1 to M21 Compound M1 was synthesized according to the method described in JP2011-174062.
Compound M2 was synthesized according to the method described in WO2002 / 045184.
Compound M3 was synthesized according to the method described in WO2005 / 049546.
Compound M4 was synthesized according to the method described in JP-A-2008-106241.
Compound M5 and Compound M7 were synthesized according to the method described in JP 2010-189630 A.
Compound M6 and Compound M17 were synthesized according to the method described in International Publication No. 2012/088671.
Compound M8 was synthesized according to the method described in JP 2010-196040 A.
Compound M9, Compound M20 and Compound M21 were synthesized according to the method described in JP-A-2006-176063.
Compound M10 and Compound M11 were synthesized according to the method described in JP2012-131995A.
Compound M12 was synthesized according to the method described in JP 2010-031246 A.
Compound M13 and Compound M14 were synthesized according to the method described in JP 2010-260879 A.
Compound M15 was synthesized according to the method described in JP-A-2015-086215.
Compound M16 was synthesized according to the method described in JP-A No. 2004-143419.
A commercially available product was used as Compound M18.
Compound M19 was synthesized according to the method described in JP2012-144722A.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 After making the inside of the reaction vessel an inert gas atmosphere, Compound M1 (2.69 g), Compound M2 (0.425 g), Compound M3 (1.64 g), Compound M4 (0.238 g), dichlorobis (triphenylphosphine) palladium (2.1 mg) and toluene (62 ml) were added and heated to 105 ° C.
A 20% by mass aqueous tetraethylammonium hydroxide solution (10 ml) was added dropwise to the reaction solution and refluxed for 4.5 hours.
After the reaction, phenylboronic acid (36.8 mg) and dichlorobis (triphenylphosphine) palladium (2.1 mg) were added thereto and refluxed for 16.5 hours.
Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with water, twice with a 3% by mass aqueous acetic acid solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred. The precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order.
The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 3.12 g of a polymer compound HTL-1. Mn of the high molecular compound HTL-1 was 7.8 × 10 ⁴ , and Mw was 2.6 × 10 ⁵ .

  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 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 M4 is a copolymer composed of a molar ratio of 50: 12.5: 30: 7.5.

<Synthesis Example HP1> Synthesis of Polymer Compound HP-1 Polymer compound HP-1 was synthesized according to the method described in JP 2012-036388 A using compound M5, compound M6, and compound M7. The Mn of the polymer compound HP-1 was 9.6 × 10 ⁴ , and the Mw was 2.2 × 10 ⁵ .
The theoretical value obtained from the amount of the raw material used for the polymer compound HP-1 includes a structural unit derived from the compound M5, a structural unit derived from the compound M6, and a structural unit derived from the compound M7. It is a copolymer constituted by a molar ratio of 50:40:10.

<Synthesis Example HP2> Synthesis of Polymer Compound HP-2 Polymer compound HP-2 was synthesized according to the method described in JP 2010-196040 A using compound M5, compound M2, and compound M8. The Mn of the polymer compound HP-2 was 2.2 × 10 ⁵ and the Mw was 7.7 × 10 ⁵ .
The theoretical value obtained from the amount of charged raw materials for polymer compound HP-2 is that the structural unit derived from compound M5, the structural unit derived from compound M2, and the structural unit derived from compound M8 are: It is a copolymer constituted by a molar ratio of 50:40:10.

<Synthesis Example HP3> Synthesis of Polymer Compound HP-3 Polymer compound HP-3 was synthesized using Compound M5, Compound M6, and Compound M9 according to the method described in JP-A-2006-176063. The Mn of the polymer compound HP-3 was 6.4 × 10 ⁴ , and the Mw was 1.4 × 10 ⁵ .
The theoretical value obtained from the amount of the raw material used for the polymer compound HP-3 includes a structural unit derived from the compound M5, a structural unit derived from the compound M6, and a structural unit derived from the compound M9. It is a copolymer constituted by a molar ratio of 50:40:10.

<Synthesis Example HP4> Synthesis of Polymer Compound HP-4 Polymer compound HP-4 was synthesized using Compound M5, Compound M6, and Compound M10 according to the method described in JP2012-131995A. The polymer compound HP-4 had an Mn of 1.3 × 10 ⁵ and an Mw of 3.1 × 10 ⁵ .
The theoretical value obtained from the amount of charged raw materials for polymer compound HP-4 is that the structural unit derived from compound M5, the structural unit derived from compound M6, and the structural unit derived from compound M10 are: It is a copolymer constituted by a molar ratio of 50:40:10.

<Synthesis Example HP5> Synthesis of Polymer Compound HP-5 The polymer compound HP-5 is composed of Compound M5, Compound M11, Compound M6, and Compound M12 according to the method described in JP2010-031246A. Synthesized. The high molecular compound HP-5 had Mn of 1.1 × 10 ⁵ and Mw of 2.8 × 10 ⁵ .
The polymer compound HP-5 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M5, a structural unit derived from the compound M11, a structural unit derived from the compound M6, and a compound. The structural unit derived from M12 is a copolymer composed of a molar ratio of 40: 10: 40: 10.

<Synthesis Example HP6> Synthesis of Polymer Compound HP-6 Polymer compound HP-6 was synthesized using Compound M5, Compound M6, Compound M13, and Compound M14 according to the method described in JP 2010-260879 A. . The polymer compound HP-6 had a Mn of 1.3 × 10 ⁵ and a Mw of 3.8 × 10 ⁵ .
The polymer compound HP-6 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M5, a structural unit derived from the compound M6, a structural unit derived from the compound M13, and a compound. The structural unit derived from M14 is a copolymer composed of a molar ratio of 50: 30: 10: 10.

<Synthesis Example HP7> Synthesis of Polymer Compound HP-7 Polymer Compound HP-7 is a method described in JP-A-2015-086215 using Compound M15, Compound M2, Compound M6, Compound M13, and Compound M16. Was synthesized according to The Mn of the polymer compound HP-7 was 1.4 × 10 ⁵ , and the Mw was 4.1 × 10 ⁵ .
The polymer compound HP-7 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M15, a structural unit derived from the compound M2, a structural unit derived from the compound M6, and a compound. The structural unit derived from M13 and the structural unit derived from the compound M16 is a copolymer composed of a molar ratio of 50: 30: 10: 5: 5.

<Synthesis Example HP8> Synthesis of Polymer Compound HP-8 Polymer Compound HP-8 is a method described in JP-A-2006-176063 using Compound M17, Compound M18, Compound M19, Compound M20 and Compound M16. Was synthesized according to The Mn of the polymer compound HP-8 was 5.3 × 10 ⁴ , and the Mw was 1.3 × 10 ⁵ .
The polymer compound HP-8 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M17, a structural unit derived from the compound M18, a structural unit derived from the compound M19, and a compound. The structural unit derived from M20 and the structural unit derived from compound M16 is a copolymer composed of a molar ratio of 36: 14: 32.5: 10: 7.5.

<Synthesis Example HP9> Synthesis of Polymer Compound HP-9 Polymer Compound HP-9 was prepared by using Compound M17, Compound M18, Compound M19, Compound M21, and Compound M16 as described in JP-A-2006-176063. Was synthesized according to The Mn of the polymer compound HP-9 was 5.1 × 10 ⁴ , and the Mw was 1.3 × 10 ⁵ .
The polymer compound HP-9 has the theoretical values determined from the amounts of raw materials charged, the structural unit derived from the compound M17, the structural unit derived from the compound M18, the structural unit derived from the compound M19, and the compound. The structural unit derived from M21 and the structural unit derived from the compound M16 is a copolymer composed of a molar ratio of 36: 14: 32.5: 10: 7.5.

<Synthesis Example HP10> Synthesis of Polymer Compound HP-10 Polymer Compound HP-10 is a method described in JP 2012-36388 A using Compound M17, Compound M18, Compound M19, Compound M7, and Compound M16. Was synthesized according to The Mn of the polymer compound HP-10 was 8.5 × 10 ⁴ , and the Mw was 2.4 × 10 ⁵ .
The polymer compound HP-10 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound M17, a structural unit derived from the compound M18, a structural unit derived from the compound M19, and a compound. The structural unit derived from M7 and the structural unit derived from the compound M16 is a copolymer composed of a molar ratio of 36: 14: 32.5: 10: 7.5.

<Synthesis Examples G1 to G4> Synthesis of Phosphorescent Compounds G1 to G4 The phosphorescent compound G1 was synthesized according to the method described in JP2013-237789A.
The phosphorescent compound G2 was synthesized according to the method described in International Publication No. 2009/131255.
The phosphorescent compound G3 was synthesized according to the method described in International Publication No. 2011/032626.
The phosphorescent compound G4 was synthesized according to the method described in JP 2014-224101 A.

<Synthesis Examples R1 to R3> Synthesis of Phosphorescent Compounds R1 to R3 The phosphorescent compound R1 was synthesized according to the method described in JP-A-2006-188673.
The phosphorescent compound R2 was synthesized according to the method described in JP-A-2008-179617.
The phosphorescent compound R3 was synthesized according to the method described in JP2011-105701A.

<Compounds H1 to H13> Synthesis or Acquisition of Compounds H1 to H13 Compound H1 was synthesized according to the method described in International Publication No. 2013/108022.
Compound H2 was synthesized according to the method described in International Publication No. 2005/049546.
Compounds H3 to H11 were purchased from Luminesense Technology.
Compound H12 was synthesized according to the method described in International Publication No. 2010/136109.
Compound H13 was synthesized according to the method described in International Publication No. 2008/056746.

  <Synthesis Example H14> Synthesis of Compound H14

After making the inside of the reaction vessel a nitrogen atmosphere, compound EM1a (50.0 g), bis (pinacolato) diboron (26.6 g), [1,1′-bis synthesized according to the method described in JP2010-031259A (Diphenylphosphino) ferrocene] palladium (II) dichloride / dichloromethane complex (PdCl ₂ (dppf) · CH ₂ Cl ₂ , 1.49 g), potassium acetate (26.8 g) and 1,4-dioxane (350 mL) were added. The mixture was stirred for 4 hours under heating to reflux. Then, after cooling to room temperature, ethyl acetate was added, and the reaction solution was washed with ion-exchanged water. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel column chromatography (mixed solvent of hexane and toluene), recrystallized using a mixed solvent of toluene and ethyl acetate, and dried to obtain compound EM1b (12.5 g, white solid). Obtained. The HPLC area percentage value of Compound EM1b was 99.5% or more.
LC-MS (ESI, positive): m / z = 1192 [M] ⁺

After making the inside of the reaction vessel a nitrogen atmosphere, compound EM1c (5.00 g), compound EM2a (4.94 g), dichlorobis (triphenylphosphine) palladium (II) synthesized according to the method described in JP 2012-144722 A (0.121 g), 20 mass% tetraethylammonium hydroxide aqueous solution (2.53 g) and toluene (200 mL) were added, and the mixture was stirred at 55 ° C. for 2 hours. Then, after cooling to room temperature, ion-exchange water was added, and it filtered with the filter which spread celite. After removing the aqueous layer from the obtained filtrate, the obtained organic layer was concentrated under reduced pressure. Hexane, toluene, and activated carbon were added thereto, and the mixture was stirred at room temperature for 1 hour, filtered through a filter with celite, and the filtrate was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene, and a mixed solvent of hexane and ethyl acetate) to obtain a crude product. The crude product was washed with a mixed solvent of acetone and hexane to obtain a solid. To this solid was added hexane, toluene and activated carbon, and the mixture was stirred at room temperature for 1 hour, filtered through a filter with silica gel and celite, and the filtrate was concentrated under reduced pressure to obtain Compound EM2b (2.5 g). It was. The HPLC area percentage value of Compound EM2b was 99.25%.
LC-MS (ESI, positive): m / z = 1259 [M] ⁺

After making the inside of reaction container nitrogen atmosphere, compound EM2b (2.45g), compound EM1b (1.16g), dichlorobis (triphenylphosphine) palladium (II) (55mg), 20 mass% tetraethylammonium hydroxide aqueous solution (1 .15 g) and toluene (25 mL) were added, and the mixture was stirred at 55 ° C. for 2 hours. Then, after cooling to room temperature, ion-exchange water was added, and it filtered with the filter which spread celite. After removing the aqueous layer from the obtained filtrate, the obtained organic layer was concentrated under reduced pressure. Toluene and activated carbon were added thereto, and the mixture was stirred at 40 ° C. for 1 hour, filtered through a filter with celite, and the filtrate was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene), further washed with methanol, and dried to obtain compound H14 (0.83 g). The HPLC area percentage value of Compound H14 was 99.5% or more.
¹ H-NMR (300 MHz, CDCl ₃ ): δ = 0.75 (t, 12H), 1.17-1.59 (m, 140H), 1.95 (s, 6H), 2.44 (t, 8H), 6.20 (d, 2H), 6.77-7.01 (m, 10H), 7.39-7.91 (m, 86H), 8.13 (s, 1H).
LC-MS (ESI, positive): m / z = 3297 [M] ⁺

<Example D1> Production and Evaluation of Light-Emitting Element D1 An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries), which is a hole injection material, was formed into a film with a thickness of 65 nm by spin coating. In an air atmosphere, the hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.
The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. 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.
1. Polymer compound HP-1, compound H1, and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = 65 mass% / 5 mass% / 30 mass%) are added to chlorobenzene. It was dissolved at a concentration of 6% by mass. Using the obtained chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 150 ° C. for 10 minutes in a nitrogen gas atmosphere.
After depressurizing the substrate on which the light emitting layer is formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride is about 4 nm on the light emitting layer as a cathode, and then on the sodium fluoride layer. Aluminum was deposited at about 80 nm. After vapor deposition, the light emitting element 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 external quantum efficiency at 600 cd / m ² was 7.61%, and the CIE chromaticity coordinates (x, y) = (0.30, 0.63).

<Example D2> Production and Evaluation of Light-Emitting Element D2 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H1 and phosphorescent compound G2 (polymer compound HP-1 / compound H1 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D2.
EL light emission was observed by applying a voltage to the light emitting element D2. The external quantum efficiency at 50 cd / m ² was 15.63% and the CIE chromaticity coordinates (x, y) = (0.32, 0.62). The external quantum efficiency at 600 cd / m ² was 16.00%, and the CIE chromaticity coordinates (x, y) = (0.32, 0.63).

<Example D3> Production and Evaluation of Light-Emitting Element D3 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = In place of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H2 and phosphorescent compound G1 (polymer compound HP-1 / compound H2 / phosphorescent compound G1 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D3.
EL light emission was observed by applying a voltage to the light emitting element D3. The external quantum efficiency at 50 cd / m ² was 8.22%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.63). The external quantum efficiency at 600 cd / m ² was 6.96%, and the CIE chromaticity coordinates (x, y) = (0.30, 0.63).

<Example D4> Production and Evaluation of Light-Emitting Element D4 In Example D1, "polymer compound HP-1, compound H1, and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent substance are added to chlorobenzene." Compound G1 = 65% by mass / 5% by mass / 30% by mass) was dissolved at a concentration of 1.6% by mass. ”Instead of“ polymer compound HP-1, compound H2 and phosphorescence in chlorobenzene ” Compound G2 (polymer compound HP-1 / compound H2 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) was dissolved at a concentration of 1.3% by mass. A light emitting device D4 was produced in the same manner as in Example D1.
EL light emission was observed by applying a voltage to the light emitting element D4. The external quantum efficiency at 50 cd / m ² was 8.49%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65). The external quantum efficiency at 600 cd / m ² was 9.10%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.65).

<Comparative Example CD1> Production and Evaluation of Light-Emitting Element CD1 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent substance in chlorobenzene) Compound G1 = 65% by mass / 5% by mass / 30% by mass) was dissolved at a concentration of 1.6% by mass ”instead of“ polymer compound HP-1 and phosphorescent compound G1 (in chlorobenzene) The polymer compound HP-1 / phosphorescent compound G1 = 70% by mass / 30% by mass) was dissolved at a concentration of 1.1% by mass. Was made.
EL light emission was observed by applying a voltage to the light emitting device CD1. The external quantum efficiency at 50 cd / m ² was 1.05%, and the CIE chromaticity coordinates (x, y) = (0.26, 0.64). The external quantum efficiency at 600 cd / m ² was 2.10%, and the CIE chromaticity coordinates (x, y) = (0.25, 0.64).

<Example D5> Production and Evaluation of Light-Emitting Element D5 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H2 and phosphorescent compound G3 (polymer compound HP-1 / compound H2 / phosphorescent compound G3 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D5.
EL light emission was observed by applying a voltage to the light emitting element D5. The external quantum efficiency at 50 cd / m ² was 9.16%, and the CIE chromaticity coordinates (x, y) = (0.31, 0.63).

<Example D6> Production and Evaluation of Light-Emitting Element D6 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H2 and phosphorescent compound G4 (polymer compound HP-1 / compound H2 / phosphorescent compound G4 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D6.
EL light emission was observed by applying a voltage to the light emitting element D6. The external quantum efficiency at 50 cd / m ² was 11.82%, and the CIE chromaticity coordinates (x, y) = (0.27, 0.63).

Example D7 Production and Evaluation of Light-Emitting Element D7 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H3 and phosphorescent compound G2 (polymer compound HP-1 / compound H3 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D7.
EL light emission was observed by applying a voltage to the light emitting element D7. The external quantum efficiency at 50 cd / m ² was 8.74%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.64).

<Example D8> Production and Evaluation of Light-Emitting Element D8 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H4 and phosphorescent compound G2 (polymer compound HP-1 / compound H4 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D8.
EL light emission was observed by applying a voltage to the light emitting element D8. The external quantum efficiency at 50 cd / m ² was 8.21%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.64).

<Example D9> Production and Evaluation of Light-Emitting Element D9 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H5 and phosphorescent compound G2 (polymer compound HP-1 / compound H5 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D9.
EL light emission was observed by applying a voltage to the light emitting element D9. The external quantum efficiency at 50 cd / m ² was 6.62%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65).

<Example D10> Production and Evaluation of Light-Emitting Element D10 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H6 and phosphorescent compound G2 (polymer compound HP-1 / compound H6 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D10.
EL light emission was observed by applying a voltage to the light emitting element D10. The external quantum efficiency at 50 cd / m ² was 8.06%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.65).

<Example D11> Production and Evaluation of Light-Emitting Element D11 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H7 and phosphorescent compound G2 (polymer compound HP-1 / compound H7 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D11.
EL light emission was observed by applying a voltage to the light emitting element D11. The external quantum efficiency at 50 cd / m ² was 8.29%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.65).

<Example D12> Production and Evaluation of Light-Emitting Element D12 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H8 and phosphorescent compound G2 (polymer compound HP-1 / compound H8 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D12.
EL light emission was observed by applying a voltage to the light emitting element D12. The external quantum efficiency at 50 cd / m ² was 7.69%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.66).

<Example D13> Production and Evaluation of Light-Emitting Element D13 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = In place of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H9 and phosphorescent compound G2 (polymer compound HP-1 / compound H9 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D13.
EL light emission was observed by applying a voltage to the light emitting element D13. The external quantum efficiency at 50 cd / m ² was 7.71%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65).

<Example D14> Production and Evaluation of Light-Emitting Element D14 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H10 and phosphorescent compound G2 (polymer compound HP-1 / compound H10 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D14.
EL light emission was observed by applying a voltage to the light emitting element D14. The external quantum efficiency at 50 cd / m ² was 6.50%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65).

Example D15 Production and Evaluation of Light-Emitting Element D15 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H11 and phosphorescent compound G2 (polymer compound HP-1 / compound H11 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D15.
EL light emission was observed by applying a voltage to the light emitting element D15. The external quantum efficiency at 50 cd / m ² was 8.02%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65).

<Example D16> Production and Evaluation of Light-Emitting Element D16 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = In place of “65 mass% / 5 mass% / 30 mass%)”, “polymer compound HP-1, compound H12 and phosphorescent compound G2 (polymer compound HP-1 / compound H12 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D16.
EL light emission was observed by applying a voltage to the light emitting element D16. The external quantum efficiency at 50 cd / m ² was 9.69%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.65).

Example D17 Production and Evaluation of Light-Emitting Element D17 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-1, compound H13 and phosphorescent compound G2 (polymer compound HP-1 / compound H13 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D17.
EL light emission was observed by applying a voltage to the light emitting element D17. The external quantum efficiency at 50 cd / m ² was 9.12%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65).

<Example D18> Production and Evaluation of Light-Emitting Element D18 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-2, compound H2 and phosphorescent compound G2 (polymer compound HP-2 / compound H2 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D18.
EL light emission was observed by applying a voltage to the light emitting element D18. The external quantum efficiency at 50 cd / m ^{2 was} 7.9%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.64).

<Example D19> Production and Evaluation of Light-Emitting Element D19 In Example D1, "polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-3, compound H2 and phosphorescent compound G2 (polymer compound HP-3 / compound H2 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D19.
EL light emission was observed by applying a voltage to the light emitting element D19. The external quantum efficiency at 50 cd / m ² was 9.28%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.64).

<Example D20> Production and Evaluation of Light-Emitting Element D20 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-4, compound H2 and phosphorescent compound G2 (polymer compound HP-4 / compound H2 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to prepare a light emitting device D20.
EL light emission was observed by applying a voltage to the light emitting element D20. The external quantum efficiency at 50 cd / m ² was 3.66%, and the CIE chromaticity coordinate (x, y) = (0.29, 0.64).

<Example D21> Production and Evaluation of Light-Emitting Element D21 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-5, compound H2, and phosphorescent compound G2 (polymer compound HP-5 / compound H2 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D21.
EL light emission was observed by applying a voltage to the light emitting element D21. The external quantum efficiency at 50 cd / m ² was 6.66%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.64).

<Example D22> Production and Evaluation of Light-Emitting Element D22 In Example D1, “polymer compound HP-1, compound H1 and phosphorescent compound G1 (polymer compound HP-1 / compound H1 / phosphorescent compound G1 = Instead of “65% by mass / 5% by mass / 30% by mass)”, “polymer compound HP-6, compound H2, and phosphorescent compound G2 (polymer compound HP-6 / compound H2 / phosphorescent compound G2 = 65% by mass / 5% by mass / 30% by mass) ”was used in the same manner as in Example D1, to fabricate a light emitting device D22.
EL light emission was observed by applying a voltage to the light emitting element D22. The external quantum efficiency at 50 cd / m ² was 8.32%, and the CIE chromaticity coordinates (x, y) = (0.29, 0.65).

<Example D23> Production and Evaluation of Light-Emitting Element D23 An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. On the anode, ND-3202 (manufactured by Nissan Chemical Industries), which is a hole injection material, was formed into a film with a thickness of 65 nm by spin coating. In an air atmosphere, the hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.
The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. 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.
1. Polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = 85 mass% / 5 mass% / 10 mass%) were added to chlorobenzene. It was dissolved at a concentration of 2% by mass. Using the obtained chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 150 ° C. for 10 minutes in a nitrogen gas atmosphere.
After depressurizing the substrate on which the light emitting layer is formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride is about 4 nm on the light emitting layer as a cathode, and then on the sodium fluoride layer. Aluminum was deposited at about 80 nm. After vapor deposition, the light emitting element D23 was produced by sealing using a glass substrate.
EL light emission was observed by applying a voltage to the light emitting element D23. The external quantum efficiency at 50 cd / m ² was 6.49%, and the CIE chromaticity coordinates (x, y) = (0.67, 0.33).

Example D24 Production and Evaluation of Light-Emitting Element D24 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-7, compound H2 and phosphorescent compound R1 (polymer compound HP-7 / compound H2 / phosphorescent compound R1 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D24.
EL light emission was observed by applying a voltage to the light emitting element D24. The external quantum efficiency at 50 cd / m ² was 5.95%, and the CIE chromaticity coordinates (x, y) = (0.68, 0.33).

<Example D25> Production and Evaluation of Light-Emitting Element D25 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-7, compound H14 and phosphorescent compound R1 (polymer compound HP-7 / compound H14 / phosphorescent compound R1 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D25.
EL light emission was observed by applying a voltage to the light emitting element D25. The external quantum efficiency at 50 cd / m ² was 6.76%, and CIE chromaticity coordinates (x, y) = (0.67, 0.32).

<Example D26> Production and Evaluation of Light-Emitting Element D26 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-8, compound H2 and phosphorescent compound R1 (polymer compound HP-8 / compound H2 / phosphorescent compound R1 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D26.
EL light emission was observed by applying a voltage to the light emitting element D26. The external quantum efficiency at 50 cd / m ² was 7.87%, and the CIE chromaticity coordinate (x, y) = (0.67, 0.33).

<Example D27> Production and Evaluation of Light-Emitting Element D27 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-9, compound H2 and phosphorescent compound R1 (polymer compound HP-9 / compound H2 / phosphorescent compound R1 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D27.
EL light emission was observed by applying a voltage to the light emitting element D27. The external quantum efficiency at 50 cd / m ² was 7.28%, and CIE chromaticity coordinates (x, y) = (0.67, 0.33).

<Example D28> Production and Evaluation of Light-Emitting Element D28 In Example D23, "polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-10, compound H2 and phosphorescent compound R1 (polymer compound HP-10 / compound H2 / phosphorescent compound R1 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D28.
EL light emission was observed by applying a voltage to the light emitting element D28. The external quantum efficiency at 50 cd / m ² was 7.38%, and CIE chromaticity coordinates (x, y) = (0.67, 0.33).

<Example D29> Production and Evaluation of Light-Emitting Element D29 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-7, compound H2 and phosphorescent compound R2 (polymer compound HP-7 / compound H2 / phosphorescent compound R2 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D29.
EL light emission was observed by applying a voltage to the light emitting element D29. The external quantum efficiency at 50 cd / m ² was 9.96%, and the CIE chromaticity coordinates (x, y) = (0.62, 0.38).

<Example D30> Production and Evaluation of Light-Emitting Element D30 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-7, compound H2 and phosphorescent compound R3 (polymer compound HP-7 / compound H2 / phosphorescent compound R3 = 85% by mass / 5% by mass / 10% by mass) ”was used in the same manner as in Example D23 to produce a light emitting device D30.
EL light emission was observed by applying a voltage to the light emitting element D30. The external quantum efficiency at 50 cd / m ² was 8.16%, and the CIE chromaticity coordinates (x, y) = (0.64, 0.35).

<Comparative Example CD2> Production and Evaluation of Light-Emitting Element CD2 In Example D23, “polymer compound HP-7, compound H1 and phosphorescent compound R1 (polymer compound HP-7 / compound H1 / phosphorescent compound R1 = Instead of “85 mass% / 5 mass% / 10 mass%)”, “polymer compound HP-7 and phosphorescent compound R1 (polymer compound HP-7 / phosphorescent compound R1 = 90 mass% / 10 mass) %) ”Was used to produce a light emitting device CD2 in the same manner as in Example D23.
EL light emission was observed by applying a voltage to the light emitting device CD2. The external quantum efficiency at 50 cd / m ² was 2.64%, and CIE chromaticity coordinates (x, y) = (0.67, 0.32).

Claims (8)

The composition containing the high molecular compound containing the structural unit represented by Formula (Z), the compound represented by Formula (1), and a phosphorescence-emitting compound.

[Where:
Ar ^Z represents a divalent heterocyclic group having a group represented by —N═ in the ring, and this group may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
Ar ^Z1 and Ar ^Z2 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar ^Z1 are present, they may be the same or different. When a plurality of Ar ^Z2 are present, they may be the same or different.
n ^Z1 and n ^Z2 each independently represent an integer of 0 or more and 5 or less. ]

[Where:
Ar ¹ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
n ¹ represents an integer of 1 to 5.
n ² represents an integer of 0 or more and 5 or less. When a plurality of n ² are present, they may be the same or different.
Ar ² represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar ² are present, they may be the same or different.
R ¹ and R ² each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of R ¹ are present, they may be the same or different. When a plurality of R ² are present, they may be the same or different.
Ar ² , R ¹ and R ² are each bonded directly to a group other than the group bonded to the nitrogen atom to which the group is bonded, or bonded via a divalent group; A ring may be formed. ] The composition according to claim 1, wherein the phosphorescent compound is a metal complex represented by the formula (M).

[Where:
M ¹ represents an iridium atom or a platinum atom.
n ^M1 represents an integer of 1 or more, and n ^M2 represents an integer of 0 or more. However, when M ¹ is an iridium atom, n ^M1 + n ^M2 is 3, and when M ¹ is a platinum atom, n ^M1 + n ^M2 is 2.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. However, at least one of E ¹ and E ² is a carbon atom.
Ring R ^M1 represents an aromatic heterocyclic ring, and this ring may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When there are a plurality of rings R ^M1 , they may be the same or different.
Ring R ^M2 represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings R ^M2 are present, they may be the same or different.
The substituent that the ring R ^M1 may have and the substituent that the ring R ^M2 may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
-A ^D1 --- A ^D2 -represents an anionic bidentate ligand. A ^D1 and A ^D2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom bonded to M ^1, and these atoms may be atoms constituting a ring. When a plurality of -A ^D1 --- A ^D2 -are present, they may be the same or different. ] The metal complex represented by formula (M) is a metal complex represented by formula Ir-1, Formula Ir-2, Formula Ir-3, Formula Ir-4, or Formula Ir-5. A composition according to 1.

[Where:
R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 are each independently a hydrogen atom Represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups may have a substituent. Good. R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 Each may be the same or different.
R ^D1 and R ^D2 , R ^D2 and R ^D3 , R ^D3 and R ^D4 , R ^D4 and R ^D5 , R ^D5 and R ^D6 , R ^D6 and R ^D7 , R ^D7 and R ^D8 , R ^D11 and R ^D12 , R ^D12 And R ^D13 , R ^D13 and R ^D14 , R ^D14 and R ^D15 , R ^D15 and R ^D16 , R ^D16 and R ^D17 , R ^D17 and R ^D18 , R ^D18 and R ^D19 , R ^D19 and R ^D20 , R ^D22 and R ^D23 , R ^D23 and R ^D24 , R ^D24 and R ^D25 , R ^D25 and R ^D26 , R ^D31 and R ^D32 , R ^D32 and R ^D33 , R ^D33 and R ^D34 , R ^D34 and R ^D35 , R ^D35 and R ^D36 , R ^D36 and R ^D37 may be bonded to each other to form a ring together with the atoms to which they are bonded.
-A ^D1 --- A ^D2- represents the same meaning as described above.
n _D1 represents 1, 2 or 3, and n _D2 represents 1 or 2. ] The Ar ¹ is a condensed ring aromatic hydrocarbon group which may have a substituent, or a condensed ring heterocyclic group which may have a substituent. A composition according to claim 1. Ar ^Z is a diazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiazole ring, oxazole ring, isothiazole ring, isoxazole ring, benzodiazole ring, benzotriazole ring, benzooxadiazole ring, benzothiadiazole Ring, benzothiazole ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, tetraazanaphthalene ring, azaanthracene ring , Diazaanthracene ring, triazaanthracene ring, tetraazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, triazaphenanthrene ring or tetraazaphenanthrene ring (This group may be substituted) directly bonded to a hydrogen atom two group remaining after removing the atom is a composition according to any one of claims 1 to 4.   The hole transport material, the hole injection material, the electron transport material, the electron injection material, the light emitting material, and at least one selected from the group consisting of an antioxidant and further containing the hole transport material. Composition.   The composition according to any one of claims 1 to 6, further comprising a solvent.   The light emitting element containing the composition as described in any one of Claims 1-6.