JP2015144260A - Light-emitting element and polymer compound used therefor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a light-emitting element superior in external quantum yield.SOLUTION: A light-emitting element comprises: an anode; a cathode; a light-emitting layer provided between the anode and the cathode; a hole transport layer provided between the anode and the light-emitting layer; and an intermediate layer provided between the light-emitting layer and the hole transport layer to be adjacent to the light-emitting layer and the hole transport layer. The light-emitting layer is arranged by use of a composition described in the item (III) and includes no amine. The hole transport layer is arranged by use of a polymer compound including a divalent aromatic amine residue. The intermediate layer is arranged by use of a polymer compound including an arylene group, and includes no amine. (III) A composition including a phosphorescent compound, of which the maximum peak wavelength of light emission spectra is 400 to less than 480 nm, and a polymer compound including a divalent heterocyclic group.

Description

  The present invention relates to a light emitting device and a polymer compound used therefor.

  Organic electroluminescence elements (hereinafter also referred to as “light-emitting elements”) have high external quantum yield and low driving voltage, and thus can be suitably used for display and illumination applications. ing. This light-emitting element includes organic layers such as a light-emitting layer and a charge transport layer. By using a polymer compound, an organic layer can be formed by a coating method typified by an ink jet printing method, and therefore, a polymer compound used for manufacturing a light-emitting element has been studied.

  If a high external quantum yield can be realized in a light-emitting element using a metal complex that exhibits blue phosphorescence in a light-emitting layer, illumination having a high external quantum yield can be realized. Therefore, research and development of light-emitting elements using metal complexes that exhibit blue phosphorescence in the light-emitting layer have been actively conducted. For example, Patent Document 1 discloses a light-emitting layer using a metal complex that exhibits blue phosphorescence and a low-molecular compound having a heterocyclic structure, and a high-strength component including a structural unit derived from fluorene and a structural unit derived from arylamine. A light-emitting element including a hole transport layer using a molecular compound and having these layers adjacent to each other is described.

JP 2011-068638 A

  However, the light emitting element described in Patent Document 1 described above does not always have an external quantum yield.

  Then, an object of this invention is to provide the light emitting element which is excellent in an external quantum yield. Another object of the present invention is to provide a polymer compound useful for forming an intermediate layer provided in the light emitting device.

When the metal complex showing blue phosphorescence, the heterocyclic ring, and the amine are in contact with each other,
(For example,
(A) When the light emitting device includes a light emitting layer containing a metal complex that exhibits blue phosphorescence, a low molecular compound having a heterocyclic structure, and an amine,
(B) When the light emitting element includes a light emitting layer containing a metal complex that exhibits blue phosphorescence emission, a polymer compound containing a structural unit having a divalent heterocyclic group, and an amine,
(C) A light emitting device includes a light emitting layer containing a metal complex exhibiting blue phosphorescence emission and a low molecular compound having a heterocyclic structure, and a hole transport layer containing an amine, and the light emitting layer and the hole transport If the layers are adjacent,
(D) A light-emitting element includes a light-emitting layer containing a metal complex exhibiting blue phosphorescence emission and a polymer compound containing a structural unit having a divalent heterocyclic group, and a hole transport layer containing an amine, When the light emitting layer and the hole transport layer are adjacent)
The energy transfer from the lowest excited triplet state of the excited metal complex exhibiting blue phosphorescence to the lowest excited triplet state of the exciplex formed by the heterocyclic ring and the amine occurs, and thus the external quantum of the light emitting device In addition to finding that the yield decreases, the present invention has been devised by finding a structure of a light-emitting element that does not cause a decrease in external quantum yield in a state where a metal complex that exhibits blue phosphorescence emission, a heterocyclic ring, and an amine are not in contact with each other. It came to complete.

The present invention, first,
The anode,
A cathode,
A light emitting layer provided between the anode and the cathode;
A hole transport layer provided between the anode and the light emitting layer;
In a light emitting device comprising an intermediate layer provided adjacent to the light emitting layer and the hole transport layer between the light emitting layer and the hole transport layer,
A light emitting layer is obtained using the following composition (I), the following composition (II), the following composition (III), the following composition (IV), or the polymer compound (V) below. And a layer containing neither a compound represented by the following formula (Z) nor a derivative of the compound represented by the following formula (Z):
The hole transport layer is a layer obtained using a polymer compound (P1) containing a structural unit represented by the following formula (X),
The intermediate layer is obtained by using a polymer compound (P2) containing a structural unit represented by the following formula (Y), and a compound represented by the following formula (Z) and a compound represented by the following formula (Z). A light-emitting element which is a layer which does not include any of the derivatives is provided.

(I) A composition containing a phosphorescent compound having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a non-phosphorescent low molecular weight compound having a heterocyclic structure.
(II) A composition containing a high molecular compound containing a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm, and a non-phosphorescent low molecular compound having a heterocyclic structure. object.
(III) A composition comprising a phosphorescent compound having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a polymer compound containing a structural unit represented by the following formula (2).
(IV) a polymer compound including a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm; and a polymer compound including a structural unit represented by the following formula (2): Containing composition.
(V) A polymer compound comprising a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a structural unit represented by the following formula (2).

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

[Wherein Ar ² represents 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 are It may have a substituent. ]

［式中、Ｒ^Ｚ１は、１価の基を表す。複数存在するＲ^Ｚ１は、同一でも異なっていてもよい。］

[Wherein R ^Z1 represents a monovalent group. A plurality of R ^Z1 may be the same or different. ]

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

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

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

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

The present invention secondly,
A structural unit having a structure of a phosphorescent compound represented by the following formula (1-A) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm;
A structural unit represented by the above formula (Y);
And a structural unit having at least one crosslinking group selected from the following crosslinking group A group,
Provided is a polymer compound containing no structural unit represented by the above formula (X).

［式中、
ｎ^１は１以上の整数を表し、ｎ^２は０以上の整数を表し、ｎ^１＋ｎ^２は２または３である。Ｍがイリジウム原子の場合、ｎ^１＋ｎ^２は３であり、Ｍが白金原子の場合、ｎ^１＋ｎ^２は２である。
Ａ^１−Ｇ^１−Ａ^２は、アニオン性の２座配位子を表し、Ｇ^１は、Ａ^１およびＡ^２とともに２座配位子を構成する原子団を表す。Ａ^１およびＡ^２は、それぞれ独立に、炭素原子、酸素原子または窒素原子を表し、これらの原子は環を構成する原子であってもよい。Ａ^１−Ｇ^１−Ａ^２が複数存在する場合、それらは同一でも異なっていてもよい。
Ｍ^１は、イリジウム原子または白金原子を表す。
Ｅ^１Ａ、Ｅ^２Ａ、Ｅ^３Ａ、Ｅ^４Ａ、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂは、それぞれ独立に、窒素原子または炭素原子を表す。Ｅ^１Ａ、Ｅ^２Ａ、Ｅ^３Ａ、Ｅ^４Ａ、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂ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。Ｅ^２Ａ、Ｅ^３Ａ、Ｅ^４Ａ、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂが窒素原子の場合、Ｒ^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂは、存在しても存在しなくてもよい。
Ｒ^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂ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価の複素環基また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^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂ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。Ｒ^２ＡとＲ^３Ａ、Ｒ^３ＡとＲ^４Ａ、Ｒ^２ＡとＲ^２Ｂ、Ｒ^２ＢとＲ^３Ｂ、Ｒ^３ＢとＲ^４Ｂ、および、Ｒ^４ＢとＲ^５Ｂ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。
環Ｒ^１Ａは、窒素原子、Ｅ^１Ａ、Ｅ^２Ａ、Ｅ^３ＡおよびＥ^４Ａとで構成されるトリアゾール環またはイミダゾール環を表す。
環Ｒ^１Bは、２つの炭素原子、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂとで構成されるベンゼン環、ピリジン環またはピリミジン環を表す。］

[Where:
n ¹ represents an integer of 1 or more, n ² represents an integer of 0 or more, and n ¹ + n ² is 2 or 3. When M is an iridium atom, n ¹ + n ² is 3, and when M is a platinum atom, n ¹ + n ² is 2.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand, and G ¹ represents an atomic group constituting a bidentate ligand together with A ¹ and A ² . A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different.
M ¹ represents an iridium atom or a platinum atom.
E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are present, they may be the same or different. When E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are nitrogen atoms, R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are present However, it does not have to exist.
R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B , they may be the same or different. R ^2A and R ^3A , R ^3A and R ^4A , R ^2A and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , and R ^4B and R ^5B are bonded to each other, together with the atoms to which they are bonded A ring may be formed.
Ring R ^1A represents a triazole ring or an imidazole ring composed of a nitrogen atom, E ^1A , E ^2A , E ^3A and E ^4A .
Ring R ^1B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^2B , E ^3B , E ^4B and E ^5B . ]

(Crosslinking group A group)

［式中、Ｒ^ＸＬは、メチレン基、酸素原子または硫黄原子を表し、ｎ^ＸＬは、０〜５の整数を表す。Ｒ^ＸＬ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、ｎ^ＸＬ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。＊は結合位置を表す。これらの架橋基は置換基を有していてもよい。］

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

  ADVANTAGE OF THE INVENTION According to this invention, the light emitting element excellent in an external quantum yield can be provided. In addition, according to the present invention, a polymer compound useful for forming an intermediate layer of the light-emitting element can be provided.

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

<Explanation of common terms>
Hereinafter, terms commonly used in the present specification have the following meanings unless otherwise specified.

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

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

  In this specification, a solid line representing a bond with a central metal in a structural formula representing a phosphorescent compound means a covalent bond or a coordinate bond.

The “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ to 1 × 10 ⁸ . The structural unit contained in the polymer compound is 100 mol% in total.

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

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

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

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

The “alkyl group” may be linear or branched. The carbon atom number of a linear alkyl group is 1-50 normally without including the carbon atom number of a substituent, Preferably it is 3-30, More preferably, it is 4-20. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.
The 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 alkyl group and cycloalkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2 -Ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyl-decyl, dodecyl Cyclohexyl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3 , 5-di-hexylphenyl) propyl group, 6-ethyloxyhexyl group, cyclohexylmethyl group, and 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 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 alkoxy group and the cycloalkoxy group may have a substituent, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, Examples include a hexyloxy group, a cyclohexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, and a lauryloxy group.

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

“P-valent heterocyclic group” (p represents an integer of 1 or more) is a p-group of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, this is an atomic group obtained by removing p hydrogen atoms from an aromatic heterocyclic compound directly bonded to carbon atoms or heteroatoms constituting the ring. A “p-valent aromatic heterocyclic group” is preferable.
`` Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc. A compound in which the ring itself exhibits aromaticity and a heterocyclic ring such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran itself does not exhibit aromaticity, but the aromatic ring is condensed to the heterocyclic ring. Means a compound.

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

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

The “amino group” may have a substituent, and a substituted amino group is preferable. As a substituent which an amino group has, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferable.
Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
Examples of the amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, and bis (3,5-di-tert- Butylphenyl) amino group.

The “alkenyl group” may be linear or branched. The carbon atom number of a linear alkenyl group is 2-30 normally without including the carbon atom number of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkenyl group and the cycloalkenyl group may have a substituent, such as a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4- Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and a group in which these groups have a substituent.

The “alkynyl group” may be linear or branched. The carbon atom number of an alkynyl group is 2-20 normally without including the carbon atom of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The number of carbon atoms of the “cycloalkynyl group” is usually 6-30, preferably 6-20, not including the carbon atoms of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4- Examples include a pentynyl group, 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 a carbon atom constituting a ring from an aromatic hydrocarbon. The carbon atom number of an arylene group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-30, More preferably, it is 6-18.
The arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formula (A-1) to formula (A-20) are preferable. The arylene group includes a group in which a plurality of these groups are bonded.

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

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

［式中、ＲおよびＲ^aは、前記と同じ意味を表す。］

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

  The “crosslinking group” is a group capable of generating a new bond by being subjected to heat treatment, ultraviolet irradiation treatment, radical reaction, etc., preferably, a crosslinking group selected from the following crosslinking group B, It is a group represented by formulas (XL-1) to (XL-17).

(Bridge group B)

［式中、Ｒ^ＸＬ、ｎ^ＸＬおよび＊は、前記と同じ意味を表す。これらの架橋基は置換基を有していてもよい。］

[Wherein R ^XL , n ^XL and * represent the same meaning as described above. These crosslinking 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.

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

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

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

[Where:
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
^TDA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

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

[Where:
^{m DA1, m DA2, m DA3} , m DA4, m DA5, m DA6 and m ^DA7 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
^TDA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably 0 or 1, More preferably 0. Also, 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) ~ (GDA -15), these groups may have a substituent.

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

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

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

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

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

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

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

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

［式中、Ｒ^DAおよびＲ^DBは前記と同じ意味を表す。］

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

  The group represented by the formula (D-A) is preferably a group represented by the formulas (D-A1) to (D-A3).

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

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

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

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

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

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

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

<Light emitting element>
The light emitting device of the present invention will be described.

<Light emitting layer>
First, the light emitting layer with which the light emitting element of this invention is provided is demonstrated.

The light emitting layer provided in the light emitting device of the present invention is
Provided between the anode and the cathode, adjacent to an intermediate layer described later,
The composition of the above (I), the composition of the above (II), the composition of the above (III), the composition of the above (IV), or the polymer compound of the above (V), It is a layer that contains neither the compound represented by Z) nor the derivative of the compound represented by formula (Z).
Among these, the light emitting layer included in the light emitting device of the present invention is obtained using the composition of the above (I) or the composition of the above (III), and the compound represented by the formula (Z) and the formula (Z) It is preferable that the layer does not contain any of the derivatives of the compound represented by formula (1), which is obtained by using the composition of (III) above, and is represented by the formula (Z) and the formula (Z). It is more preferable that the layer does not contain any of compound derivatives.

Regarding the relationship between the light-emitting layer and the composition (I), the composition (II), the composition (III), the composition (IV), or the polymer compound (V). "Obtained using" means using the composition of (I), the composition of (II), the composition of (III), the composition of (IV), or the polymer compound of (V). This means that a light emitting layer is formed.
Even if the composition of the above (I), the composition of the above (II), the composition of the above (III), the composition of the above (IV) or the polymer compound of the above (V) is contained as it is in the light emitting layer. The compound contained in the composition of (I), the composition of (II), the composition of (III) or the composition of (IV) is intramolecular, intermolecular, or those It may be contained in the light emitting layer in a crosslinked state (crosslinked body) in both, or in a state (crosslinked body) in which the polymer compound (V) is crosslinked intramolecularly, intermolecularly or both. The composition of (I), the composition of (II), the composition of (III), the composition of (IV) or the polymer of (V), which may be contained in the light emitting layer It is preferable that the compound is contained in the light emitting layer as it is.

[Phosphorescent compound]
The “phosphorescent compound” contained in the composition of the above (I) and the composition of the above (III) means a compound exhibiting phosphorescence, but preferably emits light from a triplet excited state. It is a metal complex. This metal complex that emits light from a triplet excited state has a central metal atom and a ligand.

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

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

Phosphorescent compounds are available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source.
In addition to the methods described above, “Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of the American Chemical Society, Vol. 106, 6664, 66, 664”. It can also be produced by known methods described in documents such as Japanese Patent Publication No. 2011/024761, International Publication No. 2002/044189, and Japanese Patent Application Laid-Open No. 2006-188673.

The maximum peak of the emission spectrum of the phosphorescent compound is obtained by dissolving the phosphorescent compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, etc. to prepare a dilute solution (1 × 10 ⁻⁶ to 1 × 10 ^−3). It can be evaluated by measuring the PL spectrum of the diluted solution at room temperature. Xylene is preferred as the organic solvent for dissolving the phosphorescent compound.

  The phosphorescent compound is preferably a phosphorescent compound represented by the formula (1).

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

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

E ¹ and E ² are preferably carbon atoms.

  M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, since the external quantum yield of the light emitting device of the present invention is more excellent.

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

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

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

Ring R ² is preferably a 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocycle, and a 6-membered aromatic hydrocarbon ring or 6-membered aromatic More preferably a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, pyridine ring, diazabenzene ring or triazine ring, particularly preferably a benzene ring, pyridine ring or pyrimidine ring. Preferably, these rings may have a substituent.

At least one ring selected from the group consisting of ring R ¹ and ring R ² preferably has a dendron. That is, it is preferable that a part or all of the hydrogen atoms directly bonded to the carbon atom or the hetero atom constituting at least one of the plurality of rings are substituted with a dendron. For example, in Formula (1), when there are a plurality of rings R ¹ and R ² (that is, when n ¹ is 2 or 3), among a plurality of rings R ¹ and a plurality of rings R ² , It is preferred that at least one ring has a dendron.

In the case where at least one of the ring R ¹ and the ring R ² has a dendron, the number of dendrons is usually 1 or more and 5 or less, and it is easy to synthesize a phosphorescent compound. The number is from 3 to 3, more preferably 1 or 2, and even more preferably 1.

In the case where at least one of the rings R ¹ and R ² has a dendron, the dendron is a group represented by the formula (DA) or (DB), and m ^DA1 is 1 or more When it is an integer, Ar ^DA1 bonded to ring R ¹ and / or ring R ² is preferably a phenylene group which may have a substituent, and is a group represented by the formula (ArDA-1). More preferably.

In the case where at least one of the ring R ¹ and the ring R ² has a dendron, the dendron is a group represented by the formula (DA) or (DB), and m ^DA1 is 0 If, G ^DA is attached to a ring R ¹ and / or ring R ² is a formed by removing three hydrogen atoms directly bonded to the carbon atoms constituting the ring from benzene ring which may have a substituent group Preferably, it is a group represented by the formula (GDA-11) or (GDA-12), more preferably a group represented by the formula (GDA-11).

When at least one of the ring R ¹ and the ring R ² has a dendron, the dendron is preferably a group represented by the formula (D-A1) or (D-B1). It is more preferably a group represented by -A1).

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

  When M is a palladium atom or a platinum atom, and the phosphorescent compound represented by the formula (1) has a dendron, the number of dendrons is usually 1 or more and 9 or less, and the formula (1) Since it is easy to synthesize a phosphorescent compound represented by the formula, it is preferably 1 or more and 6 or less, more preferably 2 or more and 4 or less.

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

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

R ¹¹ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group or a substituted amino group, and these groups have a substituent. It may be.

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

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

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

The substituent that the ring R ¹ and the ring R ² may have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, or an aryloxy group. A 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 more preferred, and these groups may further have a substituent. When there are a plurality of substituents that the ring R ¹ and the ring R ² may have, they may be the same or different, and may combine with each other to form a ring together with the atoms to which they are bonded.

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

［式中、＊は、Ｍまたは後述するＭ^１と結合する部位を示す。］

Wherein * indicates the binding site for the M ¹ to M or below. ]

The anionic bidentate ligand represented by A ¹ -G ¹ -A ² may be a ligand represented by the following. However, the anionic bidentate ligand represented by A ¹ -G ¹ -A ² is different from the ligand whose number is defined by the subscript n ¹ .

［式中、
＊は、前記と同じ意味を表す。
Ｒ^Ｌ１は、水素原子、アルキル基、シクロアルキル基、アリール基、１価の複素環基また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。複数存在するＲ^Ｌ１は、同一でも異なっていてもよい。
Ｒ^Ｌ２は、アルキル基、シクロアルキル基、アリール基、１価の複素環基また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:
* Represents the same meaning as described above.
R ^L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent. A plurality of R ^L1 may be the same or different.
R ^L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent. ]

R ^L1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a fluorine atom, and these groups optionally have a substituent.

R ^L2 is preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.

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

［式中、
ｎ^１、ｎ^２およびＡ^１−Ｇ^１−Ａ^２は、前記と同じ意味を表す。
Ｍ^１は、イリジウム原子または白金原子を表す。
Ｅ^１Ａ、Ｅ^２Ａ、Ｅ^３Ａ、Ｅ^４Ａ、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂは、それぞれ独立に、窒素原子または炭素原子を表す。Ｅ^１Ａ、Ｅ^２Ａ、Ｅ^３Ａ、Ｅ^４Ａ、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂ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。Ｅ^２Ａ、Ｅ^３Ａ、Ｅ^４Ａ、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂが窒素原子の場合、Ｒ^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂは、存在しても存在しなくてもよい。
Ｒ^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂ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価の複素環基また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^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂ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^２ＡとＲ^３Ａ、Ｒ^３ＡとＲ^４Ａ、Ｒ^２ＡとＲ^２Ｂ、Ｒ^２ＢとＲ^３Ｂ、Ｒ^３ＢとＲ^４Ｂ、および、Ｒ^４ＢとＲ^５Ｂ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。
環Ｒ^１Ａは、窒素原子、Ｅ^１Ａ、Ｅ^２Ａ、Ｅ^３ＡおよびＥ^４Ａとで構成されるイミダゾール環またはトリアゾール環を表す。
環Ｒ^１Bは、２つの炭素原子、Ｅ^２Ｂ、Ｅ^３Ｂ、Ｅ^４ＢおよびＥ^５Ｂとで構成されるベンゼン環、ピリジン環またはピリミジン環を表す。］

[Where:
n ^{1, n 2} and ^A 1 ^-G 1 -A ² are as defined above.
M ¹ represents an iridium atom or a platinum atom.
E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B each independently represent a nitrogen atom or a carbon atom. When there are a plurality of E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B , they may be the same or different. When E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are nitrogen atoms, R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are present However, it does not have to exist.
R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B , they may be the same or different. R ^2A and R ^3A , R ^3A and R ^4A , R ^2A and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , and R ^4B and R ^5B are bonded to each other, together with the atoms to which they are bonded A ring may be formed.
Ring R ^1A represents an imidazole ring or a triazole ring composed of a nitrogen atom, E ^1A , E ^2A , E ^3A and E ^4A .
Ring R ^1B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^2B , E ^3B , E ^4B and E ^5B . ]

M ¹ is preferably an iridium atom.

At least one ring selected from the group consisting of ring R ^1A and ring R ^1B preferably has a dendron. That is, it is preferable that a part or all of the hydrogen atoms directly bonded to the carbon atom or the hetero atom constituting at least one of the plurality of rings are substituted with a dendron. For example, in Formula (1-A), when there are a plurality of rings R ^1A and rings R ^1B (that is, n ¹ is 2 or 3), a plurality of rings R ^1A and a plurality of rings R ^1B are present. Of these, at least one ring preferably has a dendron.

It is preferable that any one of E ^2A , E ^3A and E ^4A is a nitrogen atom, or any two are nitrogen atoms, E ^2A is a nitrogen atom, or E ^2A and E More preferably, ^3A is a nitrogen atom.

When E ^2A is a nitrogen atom and R ^2A is present, R ^2A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an alkyl group, a cycloalkyl group or an aryl group It is more preferably a group, and these groups may have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

When E ^2A is a carbon atom, R ^2A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group And more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups optionally have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

When E ^3A is a nitrogen atom and R ^3A is present, R ^3A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an alkyl group, a cycloalkyl group or an aryl group It is more preferably a group, and these groups may have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

When E ^3A is a carbon atom, R ^3A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group And more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups optionally have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

When E ^4A is a nitrogen atom and R ^4A is present, R ^3A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and an alkyl group, a cycloalkyl group or an aryl group It is more preferably a group, and these groups may have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

When E ^4A is a carbon atom, R ^4A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group And more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups optionally have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

When the ring R ^1B is a pyridine ring, any one of E ^3B , E ^4B and E ^5B is preferably a nitrogen atom, and more preferably E ^3B is a nitrogen atom.

When ring R ^1B is a diazabenzene ring, any two of E ^3B , E ^4B and E ^5B are preferably nitrogen atoms, and more preferably E ^3B and E ^5B are nitrogen atoms.

Ring R ^1B is preferably a benzene ring.

R ^2B , R ^3B , R ^4B and R ^5B are preferably a hydrogen atom, an alkoxy group, a cycloalkoxy group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a fluorine atom, And more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups optionally have a substituent. The aryl group and monovalent heterocyclic group are preferably dendrons.

At least one selected from the group consisting of R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B is preferably a dendron, and R ^2A , R ^3A , R ^4A , R ^2B , When there are a plurality of R ^3B , R ^4B and R ^5B (that is, n ¹ is 2 or 3), a plurality of R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^{5B are present.} Of these, at least one is preferably a dendron.

Preferably, at least one of R ^2A , R ^3A , R ^4A , R ^3B and R ^4B is a dendron, and more preferably at least one of R ^2A , R ^3A , R ^3B and R ^4B is a dendron. preferable.

R ^5B is preferably a hydrogen atom.

  When the phosphorescent compound represented by the formula (1-A) has a dendron, a preferred range of the number of dendrons is the number of dendrons in the case where the phosphorescent compound represented by the formula (1) has a dendron. This is the same as the preferred range.

Of the rings R ^1A and R ^1B , at least one ring has a dendron, the dendron is a group represented by the formula (DA) or (DB), and m ^DA1 is 0 If, G ^DA is attached to a ring R ^1A and / or ring R ^1B is a formed by removing three hydrogen atoms directly bonded to the carbon atoms constituting the ring from benzene ring which may have a substituent group Preferably, it is a group represented by the formula (GDA-11) or (GDA-12), more preferably a group represented by the formula (GDA-11).

Of the rings R ^1A and R ^1B , at least one ring has a dendron, the dendron is a group represented by the formula (DA) or (DB), and m ^DA1 is 1 or more In the case of an integer, Ar ^DA1 bonded to ring R ^1A and / or ring R ^1B is preferably a phenylene group which may have a substituent, and is a group represented by the formula (ArDA-1). More preferably.

When at least one of the ring R ^1A and the ring R ^1B has a dendron, the dendron is preferably a group represented by the formula (D-A1) or (D-B1), and the formula (D-A1) Is more preferable.

  The phosphorescent compound represented by the formula (1-A) is preferably a phosphorescent compound represented by the formulas (1-A1) to (1-A3), and the formula (1-A1) or ( More preferably, it is a phosphorescent compound represented by 1-A3).

［式中、
Ｍ^１、Ｒ^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^２Ｂ、Ｒ^３Ｂ、Ｒ^４ＢおよびＲ^５Ｂは、前記と同じ意味を表す。
Ｒ^２Ｃ、Ｒ^３Ｃ、Ｒ^４Ｃ、Ｒ^２Ｄ、Ｒ^３Ｄ、Ｒ^４ＤおよびＲ^５Ｄ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価の複素環基また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^２Ｃ、Ｒ^３Ｃ、Ｒ^４Ｃ、Ｒ^２Ｄ、Ｒ^３Ｄ、Ｒ^４ＤおよびＲ^５Ｄ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^２ＣとＲ^３Ｃ、Ｒ^３ＣとＲ^４Ｃ、Ｒ^２ＣとＲ^２Ｄ、Ｒ^２ＤとＲ^３Ｄ、Ｒ^３ＤとＲ^４Ｄ、および、Ｒ^４ＤとＲ^５Ｄ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。
ｎ^１Ａは２または３の整数を表し、Ｍ^１がイリジウムの場合、ｎ^１Ａは３であり、Ｍ^１が白金の場合、ｎ^１Ａは２である。］

[Where:
M ¹ , R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B represent the same meaning as described above.
R ^2C , R ^3C , R ^4C , R ^2D , R ^3D , R ^4D and R ^5D are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^2C , R ^3C , R ^4C , R ^2D , R ^3D , R ^4D and R ^5D , they may be the same or different. R ^2C and R ^3C , R ^3C and R ^4C , R ^2C and R ^2D , R ^2D and R ^3D , R ^3D and R ^4D , and R ^4D and R ^5D are bonded to each other, together with the atoms to which they are bonded A ring may be formed.
n ^1A represents an integer of 2 or 3, and when M ¹ is iridium, n ^1A is 3, and when M ¹ is platinum, n ^1A is 2. ]

R ^2D , R ^3D , R ^4D and R ^5D are each preferably a hydrogen atom, an alkoxy group, a cycloalkoxy group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a fluorine atom, And more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups optionally have a substituent.

R ^5D is more preferably a hydrogen atom.

  Examples of the phosphorescent compound represented by the formula (1-A1) include phosphorescent compounds represented by the formulas (1-A1-1) to (1-A1-17).

  In Table 1, the groups represented by the formulas (Dend-A-1) to (Dend-A-5) are as follows.

［式中、Ｒ^ｐは、水素原子、アルキル基またはシクロアルキル基を表し、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^ｐは、同一でも異なっていてもよい。］

[Wherein R ^p represents a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups optionally have a substituent. A plurality of R ^p may be the same or different. ]

The alkyl group represented by R ^p, a methyl group, tert- butyl group, a hexyl group, a 2-ethylhexyl group or a 2-ethylhexyl group is preferred.

  Examples of the phosphorescent compound represented by the formula (1-A2) include phosphorescent compounds represented by the formulas (1-A2-1) to (1-A2-15).

  In Table 2, the groups represented by the formulas (Dend-A-1) to (Dend-A-5) have the same meaning as described above.

  Examples of the phosphorescent compound represented by the formula (1-A3) include phosphorescent compounds represented by the formulas (1-A3-1) to (1-A3-19).

  Examples of the phosphorescent compound include formulas (1-A1-1) to (1-A1-15), formulas (1-A2-1) to (1-A2-13), and formulas (1-A3-1) to A phosphorescent compound represented by (1-A3-6) is preferred, and is represented by formulas (1-A1-1) to (1-A1-15) or formulas (1-A3-1) to (1-A3-6). ) Is more preferable.

  As described above, the phosphorescent compound is preferably a phosphorescent compound represented by formulas (1-A1) to (1-A3), but even if it is a phosphorescent compound represented by the following, Good.

[Polymer Compound Containing Structural Unit Having Phosphorescent Compound Structure]
The polymer compound containing the structural unit having the structure of the phosphorescent compound contained in the composition of (II) and the composition of (IV) above has a maximum peak wavelength of the above emission spectrum of 400 nm or more and less than 480 nm It is a high molecular compound containing the group (residue) induced | guided | derived from the phosphorescence-emitting compound of 1 as a structural unit. In addition, if this polymer compound further includes a structural unit represented by the formula (2), the polymer compound (V) is obtained.

Examples of the group derived from the phosphorescent compound include an arylene group or divalent heterocyclic group having a substituent obtained by removing one hydrogen atom from the phosphorescent compound, and a hydrogen atom from the phosphorescent compound. Examples thereof include a group in which two hydrogen atoms have been removed and a group in which three hydrogen atoms have been removed from a phosphorescent compound.
When the structural unit is a group obtained by removing three hydrogen atoms from the phosphorescent compound, the polymer compound containing the structural unit having the structure of the phosphorescent compound is branched at the position of the structural unit. In addition, a group obtained by removing one hydrogen atom from a phosphorescent compound may be a terminal group of a polymer compound including a structural unit having a structure of the phosphorescent compound.

  The polymer compound containing a structural unit having the structure of a phosphorescent compound preferably further contains a structural unit represented by the formula (2) described later as a structural unit.

  The structural unit having the structure of the phosphorescent compound preferably has an external quantum yield of the light-emitting element, and is preferably 1 to 40 mol relative to the total amount of structural units contained in the polymer compound containing the structural unit. %, More preferably 5 to 30 mol%.

[Non-phosphorescent low molecular weight compound having a heterocyclic structure]
Examples of the non-phosphorescent low molecular weight compound having a heterocyclic structure contained in the composition (I) and the composition (II) include oxadiazole, thiadiazole, thiazole, oxazole, thiophene, and pyrrole. , Phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, phenoxazine, phenothiazine, dibenzoborol, dibenzosilole, dibenzothiophene, dibenzofuran or benzopyran as a heterocyclic structure Examples thereof include phosphorescent low-molecular compounds. Among these, preferred are non-phosphorescent low molecular weight compounds having oxadiazole, pyrazine, pyrimidine, triazine, pyridazine, quinoline or isoquinoline as a heterocyclic structure, and more preferred are pyrazine, pyrimidine, triazine or pyridazine. Is a non-phosphorescent low-molecular compound having a heterocyclic structure, more preferably a non-phosphorescent low-molecular compound having triazine or pyrimidine as a heterocyclic structure, and particularly preferably a triazine having a heterocyclic structure. It is a non-phosphorescent low molecular weight compound. Among the triazines, 1,3,5-triazine is preferable. Non-phosphorescent low molecular weight compounds having these heterocyclic structures are halogen atoms, cyano groups, alkyl groups, cycloalkyl groups, aryl groups, monovalent heterocyclic groups, alkoxy groups, cycloalkoxy groups, aryloxy groups, It may have an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group or a bridging group. The non-phosphorescent low molecular weight compound having a heterocyclic structure preferably has an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or an aryloxy group, an alkyl group, a cycloalkyl group More preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group or a monovalent heterocyclic group, and particularly preferably an aryl group. .

  The non-phosphorescent low molecular weight compound having a heterocyclic structure contained in the composition (I) and the composition (II) is preferably a compound represented by the formula (H-1). .

［式中、
Ａｒ^Ｈ１およびＡｒ^Ｈ２は、それぞれ独立に、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。
ｎ^Ｈ１およびｎ^Ｈ２は、それぞれ独立に、０または１を表す。ｎ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。複数存在するｎ^Ｈ２は、同一でも異なっていてもよい。
ｎ^Ｈ３は、０以上の整数を表す。
Ｌ^Ｈ１は、アリーレン基、２価の複素環基、または、−［Ｃ（Ｒ^Ｈ１１）_２］ｎ^Ｈ１１−で表される基を表し、これらの基は置換基を有していてもよい。Ｌ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。
ｎ^Ｈ１１は、１以上１０以下の整数を表す。Ｒ^Ｈ１１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｈ１１は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｌ^Ｈ２は、−Ｎ（−Ｌ^Ｈ２１−Ｒ^Ｈ２１）−で表される基を表す。Ｌ^Ｈ２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。
Ｌ^Ｈ２１は、単結合、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Ｈ２１は、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。］

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

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

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

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

n ^H3 is generally an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1.

n ^H11 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and even more preferably 1.

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

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

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

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

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

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

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

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

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

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

［式中、Ａｒ^Ｈ１、Ａｒ^Ｈ２、ｎ^Ｈ３およびＬ^Ｈ１は、前記と同じ意味を表す。］

[Wherein, Ar ^H1 , Ar ^H2 , n ^H3 and L ^H1 represent the same meaning as described above. ]

  Examples of the compound represented by the formula (H-1) include compounds represented by the following formulas (H-101) to (H-118).

[Polymer Compound Containing Structural Unit Represented by Formula (2)]
The polymer compound contained in the composition of (III) and the composition of (IV) includes a structural unit represented by the formula (2). If the polymer compound further includes a structural unit having the structure of a phosphorescent compound, the polymer compound (V) is obtained.

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

[Wherein Ar ² represents 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 are It may have a substituent. ]

The divalent heterocyclic group represented by Ar ² is more preferably a group represented by the formula (AA-1) to the formula (AA-4), and more preferably a formula (AA-4). These groups may have a substituent.

As the arylene group in the divalent group in which at least one kind of arylene group represented by Ar ² and at least one kind of divalent heterocyclic group are directly bonded, the formula (A-1), the formula (A-2), a group represented by formula (A-6) to formula (A-10), formula (A-19) or formula (A-20), more preferably formula (A-1) , Groups represented by formula (A-2), formula (A-7), formula (A-9) or formula (A-19), and these groups may have a substituent.
A more preferable range of the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar ² and at least one divalent heterocyclic group are directly bonded, and a more preferable range thereof are as follows: Each is the same as the more preferable range and further preferable range of the divalent heterocyclic group represented by Ar ² 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.

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

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

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

The substituent that the group represented by Ar ² 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 (2) include structural units represented by the formulas (2-1) to (2-4).

［式中、
Ｒ^Y1は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y1は、同一でも異なっていてもよく、隣接するＲ^Y1同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。
Ｒ^Y3は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[Where:
R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
R ^Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. ]

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

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

  The structural unit represented by the formula (2-1) is preferably a structural unit represented by the formula (2-1 ′), and the structural unit represented by the formula (2-3) is represented by the formula (2 -3 ′) is preferred.

［式中、Ｒ^Y1およびＲ^Y3は、前記と同じ意味を表す。］

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

  Examples of the structural unit represented by the formula (2) include at least one arylene group and at least one divalent heterocyclic group represented by the formulas (2-101) to (2-113). Examples thereof include a structural unit composed of a divalent group directly bonded.

  The structural unit represented by the formula (2) preferably has an external quantum yield of the light-emitting element, and is preferably 0.5 to 30 mol based on the total amount of the structural units contained in the polymer compound having the structural unit. %, More preferably 3 to 20 mol%.

The polymer compound containing the structural unit represented by Formula (2) is a structural unit represented by Formula (Y) described later in <Hole Transport Layer> (however, the structural unit represented by Formula (2)). It is preferable that it further contains.
That is, the polymer compound containing the structural unit represented by the formula (2) contained in the composition of (III) is composed of the structural unit represented by the formula (2) and the structure represented by the formula (Y). A polymer compound containing a unit is preferred.
Moreover, the high molecular compound containing the structural unit represented by Formula (2) contained in the composition of said (IV) is the structure represented by the structural unit represented by Formula (2), and Formula (Y). A polymer compound containing a unit is preferred.
The polymer compound (V) is a polymer compound including a structural unit having a phosphorescent compound structure, a structural unit represented by the formula (2), and a structural unit represented by the formula (Y). Preferably there is.
Examples and preferred ranges of the structural unit represented by formula (Y) are the same as examples and preferred ranges of the structural unit represented by formula (Y) described later in <Hole transport layer>.

[Compound represented by formula (Z) and derivative of compound represented by formula (Z)]
The light-emitting layer included in the light-emitting element of the present invention is a layer that does not include the compound represented by the formula (Z) and the derivative of the compound represented by the formula (Z).

［式中、Ｒ^Ｚ１は、１価の基を表す。複数存在するＲ^Ｚ１は、同一でも異なっていてもよい。］

[Wherein R ^Z1 represents a monovalent group. A plurality of R ^Z1 may be the same or different. ]

Examples of the monovalent group represented by R ^Z1 include a hydrogen atom, a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, and an aryloxy group. Groups, amino groups, substituted amino groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, cycloalkynyl groups and bridging groups.

  The derivative of the compound represented by the formula (Z) means a compound having a remaining group (residue) obtained by removing one or more hydrogen atoms from the compound represented by the formula (Z). And a polymer compound containing a structural unit represented by the formula (X).

  Examples of the polymer compound used for forming the light emitting layer include polymer compounds P-1 to P-6 shown in Table 5 below. Here, the “other” structural unit refers to the structural unit represented by the formula (2), the structural unit represented by the formula (Y), and the structure of the phosphorescent compound represented by the formula (1-A). It means a structural unit other than the structural unit it has.

［表中、ｐ、ｑ、ｒ、ｓおよびｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝１００であり、かつ、１００≧ｐ＋ｑ＋ｒ＋ｓ≧７０である。その他の構成単位とは、式(2)で表される構成単位、式(Y)で表される構成単位および式(1-A)で表される燐光発光化合物の構造を有する構成単位以外の構成単位を意味する。］

[In the table, p, q, r, s and t represent the molar ratio of each constituent unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70. The other structural unit means a structural unit represented by the formula (2), a structural unit represented by the formula (Y), and a structural unit other than the structural unit having the structure of the phosphorescent compound represented by the formula (1-A). A structural unit. ]

[Composition ratio and others]
The composition (I) contains a phosphorescent compound having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a non-phosphorescent low molecular weight compound having a heterocyclic structure. The functional compound is usually 0.1 to 1000 parts by weight, preferably 1 to 200 parts by weight, more preferably 100 parts by weight of the non-phosphorescent low molecular weight compound having a heterocyclic structure. 10 to 100 parts by weight.

  The composition (II) includes a polymer compound containing a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm, and a non-phosphorescent low-phosphorescent compound having a heterocyclic structure. Although the molecular compound is contained, the polymer compound containing a structural unit having the structure of a phosphorescent compound is generally 0. 10 parts by weight with respect to 100 parts by weight of the non-phosphorescent low molecular compound having a heterocyclic structure. It is 1-1000 weight part, Preferably, it is 1-400 weight part, More preferably, it is 10-200 weight part.

  The composition of (III) above contains a phosphorescent compound having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a polymer compound containing a structural unit represented by the formula (2). The phosphorescent compound is usually 0.1 to 1000 parts by weight, preferably 1 to 200 parts by weight with respect to 100 parts by weight of the polymer compound containing the structural unit represented by the formula (2). More preferably, it is 10 to 100 parts by weight.

  The composition of (IV) includes a polymer compound including a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm, and a structural unit represented by the formula (2). A polymer compound containing a structural unit having the structure of a phosphorescent compound is contained in 100 parts by weight of the polymer compound containing the structural unit represented by the formula (2). Usually, it is 0.1 to 1000 parts by weight, preferably 1 to 400 parts by weight, and more preferably 10 to 200 parts by weight.

  The polymer compound (V) includes a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm, and a structural unit represented by the formula (2). The structural unit having the structure of the phosphorescent compound is usually 0.1 to 99 mol%, preferably 0.5 to 80 mol per 100 mol% of the structural unit represented by the formula (2). It is mol%, More preferably, it is 1-50 mol%.

<Hole transport layer>
Next, the hole transport layer provided in the light emitting device of the present invention will be described.

The hole transport layer provided in the light emitting device of the present invention,
Provided between the anode and the light emitting layer, adjacent to an intermediate layer described later,
It is a layer obtained by using the polymer compound (P1) containing the structural unit represented by the formula (X).

“Obtained using” in relation to the relationship between the hole transport layer and the polymer compound (P1) means that the hole transport layer is formed using the polymer compound (P1).
The polymer compound (P1) may be contained in the hole transport layer as it is, or the polymer compound (P1) is in a state where the polymer compound (P1) is crosslinked in the molecule, between the molecules, or both (crosslinked product). Although it may be contained in the transport layer, it is preferable that the polymer compound (P1) is contained in the hole transport layer in a state where the polymer compound (P1) is cross-linked in the molecule, between the molecules, or both. .

[Structural Unit Represented by Formula (X)]
The polymer compound (P1) includes a structural unit represented by the formula (X).

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

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

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

a ^X2 is preferably 2 or less, more preferably 0, because the external quantum yield of the light emitting device of the present invention is more excellent.

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

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

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

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

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

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

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

Examples of 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 include groups represented by the following formulae: These may have a substituent.

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

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

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

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

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

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

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

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

  Examples of the structural unit represented by formula (X) include structural units represented by formulas (X1-1) to (X1-19), preferably formulas (X1-6) to (X1-14). ).

  The structural unit represented by the formula (X) is preferably 0.1 to 50 with respect to the total amount of the structural units contained in the polymer compound (P1) because the hole transport property of the polymer compound (P1) is excellent. It is mol%, More preferably, it is 1-40 mol%, More preferably, it is 5-30 mol%.

  In the polymer compound (P1), only one type of structural unit represented by the formula (X) may be included, or two or more types of structural units may be included.

[Structural Unit Represented by Formula (Y)]
The polymer compound (P1) preferably further includes a structural unit represented by the formula (Y). That is, the polymer compound (P1) preferably includes a structural unit represented by the formula (X) and a structural unit represented by the formula (Y).

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

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

The arylene group represented by Ar ^Y1 is more preferably a formula (A-1), a formula (A-6), a formula (A-7), a formula (A-9) to a formula (A-11), a formula (A-13) or a group represented by formula (A-19), more preferably formula (A-1), 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-4), a formula (AA-10), a formula (AA-13), a formula (AA-15), a formula (AA- 18) or a group represented by formula (AA-20), more preferably a group represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20). These groups may have a substituent.

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

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

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-1) to (Y-7), and the external quantum yield of the light emitting device of the present invention is more excellent. Therefore, it is preferably a structural unit represented by the formula (Y-1) or (Y-2). From the viewpoint of the electron transport property of the polymer compound (P1), the formula (Y-3) or ( Y-4), and from the viewpoint of the hole transport property of the polymer compound (P1), preferably the structural units represented by formulas (Y-5) to (Y-7) is there.

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

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

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

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

In X ^Y1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded. When R ^Y2 forms a ring, —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — The group represented is preferably a group represented by formulas (Y-B1) to (Y-B5), more preferably a group represented by formula (Y-B3), and these groups are substituted. It may have a group.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

[Wherein, R ^Y2 represents the same meaning as described above. ]

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

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

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

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

[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.

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-11) to (Y-55).

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, has a higher external quantum yield of the light-emitting element of the present invention, and therefore is included in the polymer compound (P1). Preferably it is 0.5-80 mol% with respect to the total amount of a unit, More preferably, it is 30-60 mol%.

A structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group directly bonded to each other. Since the structural unit which is a group of the polymer compound (P1) is excellent in charge transporting property, it is preferably 0.5 to 30 mol% based on the total amount of the structural units contained in the polymer compound (P1). More preferably, it is 3-40 mol%.

  In the polymer compound (P1), only one type of structural unit represented by the formula (Y) may be included, or two or more types of structural units may be included.

[Structural unit having a crosslinking group]
The polymer compound (P1) preferably further includes a structural unit having at least one crosslinking group selected from the crosslinking group B group. That is, the polymer compound (P1) preferably includes a structural unit represented by the formula (X) and a structural unit having at least one crosslinking group selected from the bridging group B, and is represented by the formula (X). It is more preferable to include a structural unit having at least one crosslinking group selected from the structural units represented by formula (Y) and the crosslinking group B group.

  Examples of the substituent that the crosslinking groups represented by the formulas (XL-1) to (XL-17) in the crosslinking group B may have include, for example, an alkyl group, a cycloalkyl group, an alkoxy group, and a cycloalkoxy group. , Aryl group, aryloxy group, halogen atom, monovalent heterocyclic group and cyano group.

  As the cross-linking group, the polymer compound (P1) has excellent cross-linking properties, so that the formula (XL-1), (XL-3), (XL-5), (XL-7), (XL-16) or (XL-16) A crosslinking group represented by XL-17) is preferred, and a crosslinking group represented by formula (XL-1) or (XL-17) is more preferred.

  As the structural unit having at least one crosslinking group selected from the bridging group B, a structural unit represented by the formula (3) or a structural unit represented by the formula (3 ′) described below is preferable. It may be a structural unit represented.

  The structural unit having a crosslinking group is preferably a structural unit represented by the formula (3) or a structural unit represented by the formula (3 ′).

［式中、
ｎＡは０〜５の整数を表し、ｎは１または２を表す。
Ａｒ^３は、芳香族炭化水素基または複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^Ａは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子または硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^Ａ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。
Ｘは、架橋基Ｂ群から選ばれる架橋基を表す。Ｘ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:
nA represents an integer of 0 to 5, and n represents 1 or 2.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of ^LA are present, they may be the same or different.
X represents a crosslinking group selected from the crosslinking group B group. When two or more X exists, they may be the same or different. ]

  nA is preferably 0 or 1, more preferably 0, because the external quantum yield of the light emitting device of the present invention is more excellent.

  n is preferably 2 because the external quantum yield of the light-emitting device of the present invention is more excellent.

Ar ³ is preferably an aromatic hydrocarbon group because the external quantum yield of the light emitting device of the present invention is more excellent.

The number of carbon atoms of the aromatic hydrocarbon group represented by Ar ³ 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. is there.
As the arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar ³ , more preferably, the formula (A-1), the formula (A-2), and the formula (A-6) To groups represented by formula (A-10), formula (A-19) or formula (A-20), more preferably formula (A-1), formula (A-2), formula (A -7), a group represented by formula (A-9) or formula (A-19), and these groups may have a substituent.

The number of carbon atoms of the heterocyclic group represented by Ar ³ 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 aromatic hydrocarbon group and heterocyclic group represented by Ar ³ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group. Group, halogen atom, monovalent heterocyclic group and cyano group.

Alkylene group represented by L ^A is not including the carbon atom number of substituent is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3. Cycloalkylene group represented by L ^A is not including the carbon atom number of substituent is usually 3 to 10.
The alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.

Alkylene group and cycloalkylene group represented by L ^A may have a substituent. Examples of the substituent that the alkylene group and the cycloalkylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, and a cyano group.

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

L ^A, since it is easy to synthesize the polymer compound (P1), is preferably a phenylene group or a methylene group.

  The preferred range and more preferred range of the crosslinking group represented by X are the same as the preferred range and more preferred range of the crosslinking group selected from the aforementioned crosslinking group B.

  The structural unit represented by the formula (3) is excellent in stability of the polymer compound (P1) and excellent in crosslinkability of the polymer compound (P1), and therefore is included in the polymer compound (P1). The total amount is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, and still more preferably 3 to 20 mol%.

  In the polymer compound (P1), only one type of structural unit represented by the formula (3) may be included, or two or more types of structural units may be included.

［式中、
ｍＡは０〜５の整数を表し、ｍは１〜４の整数を表し、ｃは０または１の整数を表す。
ｍＡ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^５は、芳香族炭化水素基、複素環基、または、少なくとも１種の芳香族炭化水素環と少なくとも１種の複素環が直接結合した基を表し、これらの基は置換基を有していてもよい。
Ａｒ^４およびＡｒ^６は、それぞれ独立に、アリーレン基または２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^４、Ａｒ^５およびＡｒ^６はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接または酸素原子もしくは硫黄原子を介して結合して、環を形成していてもよい。
Ｋ^Ａは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’’−で表される基、酸素原子または硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’’は、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｋ^Ａ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。
Ｘ’は、架橋基Ｂ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。但し、少なくとも１つのＸ’は、架橋基Ｂ群から選ばれる架橋基である。］

[Where:
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1.
When a plurality of mA are present, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. May be.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or through an oxygen atom or sulfur atom, to form a ring. It may be.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR '' -, a group represented by an oxygen atom or a sulfur atom, these groups have a substituent May be. R ″ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of K ^A are present, they may be the same or different.
X ′ represents a bridging group selected from the bridging group B group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. However, at least one X ′ is a crosslinking group selected from the crosslinking group B group. ]

  mA is preferably 0 or 1 because the external quantum yield of the light emitting device of the present invention is more excellent.

  m is preferably 2 because the external quantum yield of the light emitting device of the present invention is more excellent.

  c is preferably 0 because synthesis of the polymer compound (P1) is facilitated and the external quantum yield of the light-emitting device of the present invention is more excellent.

Ar ⁵ is preferably an aromatic hydrocarbon group because the external quantum yield of the light emitting device of the present invention is more excellent.

The definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar ⁵ are the same as the definition and example of the arylene group represented by Ar ^X2 in the above formula (X). It is.

The definition and example of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar ⁵ are the divalent heterocyclic group represented by Ar ^X2 in the above formula (X). Same as definition and example of part.

The definition and example of the divalent group excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ⁵ and at least one heterocycle are directly bonded are defined by the above formula ( The definition and examples of the divalent group in which at least one arylene group represented by Ar ^X2 in X) and at least one divalent heterocyclic group are directly bonded are the same.

Ar ⁴ and Ar ⁶ are preferably an arylene group because the external quantum yield of the light emitting device of the present invention is more excellent.

The definitions and examples of the arylene groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the arylene groups represented by Ar ^X1 and Ar ^X3 in the above formula (X).

The definitions and examples of the divalent heterocyclic group represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 in the above formula (X). is there.

The groups represented by Ar ⁴ , Ar ⁵ and Ar ⁶ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, Examples thereof include a halogen atom, a monovalent heterocyclic group, and a cyano group.

Alkylene group represented by K ^A, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by L ^A, a cycloalkylene group, an arylene group, a divalent heterocyclic The definition and examples of the ring group are the same.
K ^A, since it is easy to synthesize the polymer compound (P1), is preferably a phenylene group or a methylene group.

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

  The structural unit represented by the formula (3 ′) is included in the polymer compound (P1) because the stability of the polymer compound (P1) is more excellent and the crosslinking property of the polymer compound (P1) is more excellent. It is preferable that it is 0.5-50 mol% with respect to the total amount of the structural unit to be formed, it is more preferable that it is 3-30 mol%, and it is further more preferable that it is 3-20 mol%.

  In the polymer compound (P1), only one type of structural unit represented by formula (3 ′) may be included, or two or more types of structural units may be included.

  As a structural unit represented by Formula (3), the structural unit represented by Formula (3-1)-Formula (3-30) is mentioned, for example, As a structural unit represented by Formula (3 ') Includes, for example, structural units represented by formula (3′-1) to formula (3′-13). Among these, since the crosslinkability of the polymer compound (P1) is excellent, the structural unit represented by any one of the formulas (3-1) to (3-30) is preferable, and the formula (3-1) to the formula A structural unit represented by (3-15), formula (3-19), formula (3-20), formula (3-23), formula (3-25) or formula (3-30) is preferred, The structural unit represented by (3-1) to formula (3-13) or formula (3-30) is more preferred, and in formula (3-1) to formula (3-9) or formula (3-30) The structural unit represented is more preferable.

  Examples of the polymer compound used for forming the hole transport layer include polymer compounds P-11 to P-19 shown in Table 6 below. Here, the `` other '' constituent unit is a constituent unit represented by the formula (X), a constituent unit represented by the formula (Y), a constituent unit represented by the formula (3), and the formula (3 ′). Means a structural unit other than the structural unit represented by

［表中、ｐ、ｑ、ｒ、ｓ、ｔおよびｕは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＋ｕ＝１００であり、かつ、１００≧ｐ＋ｑ＋ｒ＋ｓ＋ｔ≧７０である。その他の構成単位とは、式(X)で表される構成単位、式(Y)で表される構成単位、式(3)で表される構成単位および式(3’)で表される構成単位以外の構成単位を意味する。］

[In the table, p, q, r, s, t and u indicate the molar ratio of each constituent unit. p + q + r + s + t + u = 100 and 100 ≧ p + q + r + s + t ≧ 70. The other structural units are the structural unit represented by the formula (X), the structural unit represented by the formula (Y), the structural unit represented by the formula (3), and the structure represented by the formula (3 ′). Means a structural unit other than a unit. ]

<Intermediate layer>
Next, the intermediate layer provided in the light emitting device of the present invention will be described.

The intermediate layer provided in the light emitting device of the present invention is:
Between the light emitting layer and the hole transport layer, provided adjacent to the light emitting layer and the hole transport layer,
A layer obtained by using the polymer compound (P2) containing the structural unit represented by the formula (Y) and not including the compound represented by the formula (Z) and the derivative of the compound represented by the formula (Z). is there.

“Obtained using” in relation to the relationship between the intermediate layer and the polymer compound (P2) means that the intermediate layer is formed using the polymer compound (P2).
The polymer compound (P2) may be contained in the intermediate layer as it is, or the polymer compound (P2) is contained in the intermediate layer in a state where the polymer compound (P2) is crosslinked in the molecule, between the molecules, or both. However, the polymer compound (P2) is preferably contained in the intermediate layer in a state where the polymer compound (P2) is crosslinked intramolecularly, intermolecularly or both (crosslinked product).

[Structural Unit Represented by Formula (Y)]
The polymer compound (P2) includes a structural unit represented by the formula (Y). Examples and preferred ranges of the structural unit represented by the formula (Y) are the same as the examples and preferred ranges of the structural unit represented by the formula (Y) described above in <Hole transport layer>, but the polymer The structural unit represented by the formula (Y) contained in the compound (P2) is preferably a structural unit represented by the formula (4).

［式中、
Ａｒ^７は、芳香族炭化水素基を表し、この基はＲ^３以外の置換基を有していてもよい。
Ｒ^３は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^３が複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも１つのＲ^３は、他の構成単位と結合を形成する炭素原子の隣の炭素原子に結合する。
ｐ^３は、１以上の整数を表す。］

[Where:
Ar ⁷ represents an aromatic hydrocarbon group, and this group may have a substituent other than R ³ .
R ³ represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of R ³ are present, they may be the same or different. Provided that at least one of R ³ binds to a carbon atom adjacent to the carbon atoms forming a bond with the other structural units.
p ³ is an integer of 1 or greater. ]

The number of carbon atoms of the aromatic hydrocarbon group represented by Ar ⁷ 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. is there.
As the arylene group portion excluding the p ³ substituents of the aromatic hydrocarbon group represented by Ar ⁷ , more preferably, the formula (A-1), the formula (A-2), the formula (A-6) ) To Formula (A-10), Formula (A-19), or Formula (A-20), and more preferably Formula (A-1), Formula (A-2), Formula (A). A-7), a group represented by formula (A-9) or formula (A-19), and these groups optionally have a substituent.

R ³ is preferably an alkyl group, a cycloalkyl group, or an aryl group.

p ³ is preferably an integer of 1 to 4, and more preferably 1 or 2.

  The structural unit represented by the formula (4) is preferably a structural unit represented by the formula (4-1) or (4-2) because the external quantum yield of the light emitting device of the present invention is more excellent. The structural unit represented by formula (4-1) is more preferable.

［式（４−１）中、
Ｒ^Y１Ａは、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ１Ａは、同一でも異なっていてもよい。
Ｒ^Ｙ１Ｂは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ１Ｂは、同一でも異なっていてもよい。］

[In Formula (4-1),
R ^Y1A 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 ^Y1A may be the same or different.
R ^Y1B 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 ^Y1B may be the same or different. ]

R ^Y1A is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, more preferably an alkyl group, a cycloalkyl group or an aryl group, still more preferably an alkyl group or a cycloalkyl group These groups may have a substituent.

R ^Y1B is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, still more preferably a hydrogen atom, and these groups are It may have a substituent.

  The structural unit represented by the formula (4-1) is preferably a structural unit represented by the formula (4-1 ′).

［式中、Ｒ^Ｙ１ＡＡは、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ１ＡＡは、同一でも異なっていてもよい。］

[ ^Wherein , R ^Y1AA 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 ^Y1AA may be the same or different. ]

R ^Y1AA is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, more preferably an alkyl group, a cycloalkyl group or an aryl group, still more preferably an alkyl group or a cyclo It is an alkyl group, and these groups may have a substituent.

［式中、
Ｒ^Y１ＡおよびＲ^Ｙ１Ｂは、前記と同じ意味を表す。
Ｘ^Y1は、−Ｃ(Ｒ^Y1C)_２−、−Ｃ(Ｒ^Y1C)＝Ｃ(Ｒ^Y1C)−または−Ｃ(Ｒ^Y1C)₂−Ｃ(Ｒ^Y1C)₂−で表される基を表す。Ｒ^Y1Cは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y1Cは、同一でも異なっていてもよく、Ｒ^Y1C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 ^Y1A and R ^Y1B represent the same meaning as described above.
X ^{Y1 _{is, -C (R Y1C) 2 -}} , - represents a group represented by ^{- C (R Y1C) = C} (R Y1C) - or _{^{-C (R Y1C) 2 -C (}} R Y1C) 2. R ^Y1C 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 ^Y1C may be the same or different, and R ^Y1C may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

In X ^Y1 , the combination of two R ^Y1C groups in the group represented by —C (R ^Y1C ) 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 ^Y1Cs may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y1C forms a ring, the group represented by —C (R ^Y1C ) ₂ — Is preferably a group represented by formulas (4-A1) to (4-A5), more preferably a group represented by formula (4-A4), and these groups have a substituent. It may be.

In X ^Y1 , the combination of two R ^Y1C groups in the group represented by —C (R ^Y1C ) ═C (R ^Y1C ) — is preferably both an alkyl group or a cycloalkyl group, or one of which is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

In X ^Y1C , four R ^Y1C groups in the group represented by —C (R ^Y1C ) ₂ —C (R ^Y1C ) ₂ — are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y1C may be bonded to each other to form a ring together with the atoms to which each is bonded. When R ^Y1C forms a ring, —C (R ^Y1C ) ₂ —C (R ^Y1C ) ₂ — The group represented is preferably a group represented by formulas (4-B1) to (4-B5), more preferably a group represented by formula (4-B3), and these groups are substituted. It may have a group.

［式中、Ｒ^Y1Cは前記と同じ意味を表す。］

[ ^Wherein R ^Y1C represents the same meaning as described above. ]

  The structural unit represented by the formula (4-2) is preferably a structural unit represented by the formula (4-2 ′).

［式中、Ｒ^Y１ＡおよびＸ^Y1は、前記と同じ意味を表す。］

[Wherein, R ^Y1A and X ^Y1 represent the same meaning as described above. ]

  Examples of the structural unit represented by the formula (4) include structural units composed of aromatic hydrocarbon groups represented by the formulas (4-001) to (4-021).

  Since the external quantum yield of the light emitting device of the present invention is more excellent, the structural unit represented by the formula (4) is 0.5 to 90 mol% with respect to the total amount of the structural units contained in the polymer compound (P2). It is preferable that it is, and it is more preferable that it is 30-85 mol%.

  In the polymer compound (P2), only one type of structural unit represented by formula (4) may be included, or two or more types of structural units may be included.

[Structural unit having a crosslinking group]
The polymer compound (P2) preferably further includes a structural unit having at least one crosslinking group selected from the crosslinking group A group. That is, the polymer compound (P2) preferably includes a structural unit represented by the formula (Y) and a structural unit having at least one crosslinking group selected from the crosslinking group A group, and is represented by the formula (4). It is more preferable to include a structural unit having at least one crosslinking group selected from the structural unit and the crosslinking group A group.

  Examples of the substituent that the crosslinking groups represented by formulas (XL-1) to (XL-17) in the crosslinking group A may have include, for example, an alkyl group, a cycloalkyl group, an alkoxy group, and a cycloalkoxy group. , Aryl group, aryloxy group, halogen atom, monovalent heterocyclic group and cyano group.

  As the crosslinking group, a crosslinking group represented by the formula (XL-1) or (XL-17) is preferable since the crosslinking property of the polymer compound (P2) is excellent.

  As the structural unit having at least one cross-linking group selected from the cross-linking group A group, a structural unit represented by the formula (5) described later is preferable, but may be a structural unit represented below.

  As the structural unit having a crosslinking group, the structural unit represented by the formula (5) is preferable.

［式中、
ｎＡは０〜５の整数を表し、ｎは１または２を表す。
Ａｒ^３は、芳香族炭化水素基または複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^Ｂは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、酸素原子または硫黄原子を表し、これらの基は置換基を有していてもよい。Ｌ^Ｂ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。
Ｘ’’は、架橋基Ａ群から選ばれる架橋基を表す。Ｘ’’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:
nA represents an integer of 0 to 5, and n represents 1 or 2.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
L ^B is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, an oxygen atom or a sulfur atom, and these groups may have a substituent. When a plurality of ^LB are present, they may be the same or different.
X ″ represents a crosslinking group selected from the crosslinking group A group. When a plurality of X ″ are present, they may be the same or different. ]

nA, examples and preferred ranges of n and Ar ^3, and more preferably ranges and more preferred ranges are examples and preferred ranges of nA, n and Ar ³ in the formula (3) is the same as the more this preferred range and a more preferred range .

Examples and preferred ranges alkylene group and cycloalkylene group represented by L ^B is the same as the example and preferred ranges of alkylene group and cycloalkylene group represented by L ^A.

Examples and preferred ranges of the arylene group represented by L ^B is the same as the examples of arylene group and preferred ranges represented by L ^A.

L ^B, since it is easy to synthesize the polymer compound (P1), is preferably a phenylene group or a methylene group.

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

  The structural unit represented by the formula (5) is excellent in stability of the polymer compound (P2) and excellent in crosslinkability of the polymer compound (P2). Therefore, the structural unit contained in the polymer compound (P2). The total amount is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, and still more preferably 3 to 20 mol%.

  In the polymer compound (P2), only one type of structural unit represented by the formula (5) may be included, or two or more types of structural units may be included.

  As a structural unit represented by Formula (5), the structural unit represented by said Formula (3-1)-Formula (3-30) is mentioned, for example. Among these, since the crosslinkability of the polymer compound (P2) is excellent, Formula (3-1) to Formula (3-15), Formula (3-19), Formula (3-20), Formula (3-23) ), A structural unit represented by formula (3-25) or formula (3-30) is preferred, and a structural unit represented by formula (3-1) to formula (3-13) or formula (3-30) Are more preferable, and the structural unit represented by Formula (3-1) to Formula (3-9) or Formula (3-30) is more preferable.

[Structural unit having structure of phosphorescent compound]
Since the polymer compound (P2) has excellent hole transportability, the polymer compound (P2) further has a phosphorescent compound structure represented by the above formula (1-A) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm. It is preferable that a structural unit is included. More specifically, the intermediate layer is a layer that does not contain the compound represented by the formula (Z) and the derivative of the compound represented by the formula (Z). By forming the intermediate layer using the polymer compound (P2) containing the structural unit having the structure of the phosphorescent compound represented by the above, it becomes an intermediate layer excellent in hole transportability, and more efficiently the light emitting layer This is because holes can be transported to the surface. That is, the polymer compound (P2) preferably includes a structural unit represented by the formula (Y) and a structural unit having a phosphorescent compound structure represented by the formula (1-A). And a structural unit having a structure of a phosphorescent compound represented by the formula (1-A) and a structural unit having at least one cross-linking group selected from the cross-linking group A group. preferable.

As the structural unit having the structure of the phosphorescent compound represented by the formula (1-A), for example, the remaining residue obtained by removing one hydrogen atom from the phosphorescent compound represented by the formula (1-A) An arylene group or divalent heterocyclic group as a substituent, the remaining residue obtained by removing two hydrogen atoms from the phosphorescent compound represented by the formula (1-A), and the formula (1-A) The remaining residue which remove | eliminated three hydrogen atoms from the phosphorescence-emitting compound represented by these is mentioned.
When this structural unit is the remaining residue obtained by removing three hydrogen atoms from the phosphorescent compound represented by the formula (1-A), the phosphorescent compound represented by the formula (1-A) The polymer compound (P2) containing a structural unit having a structure is branched at the position of this structural unit. The remaining residue obtained by removing one hydrogen atom from the phosphorescent compound represented by the formula (1-A) is a structural unit having the structure of the phosphorescent compound represented by the formula (1-A). May be a terminal group of the polymer compound (P2) containing.

  Since the structural unit having the structure of the phosphorescent compound represented by the formula (1-A) has an excellent external quantum yield of a light-emitting element manufactured using the polymer compound (P2), the polymer compound (P2 ) Is preferably 0.001 to 50 mol%, and more preferably 0.01 to 30 mol%, based on the total amount of the structural units contained in (1).

  In the polymer compound (P2), only one type of structural unit having the structure of the phosphorescent compound represented by the formula (1-A) may be included, or two or more types of structural units may be included.

<Compound represented by formula (Z) and derivative of compound represented by formula (Z)>
The intermediate layer included in the light-emitting element of the present invention is a layer that does not include the compound represented by the formula (Z) and the derivative of the compound represented by the formula (Z). Definitions and examples of the compound represented by the formula (Z) and the derivative of the compound represented by the formula (Z) are represented by the compound represented by the formula (Z) and the formula (Z) described above in <Light-Emitting Layer>. The definitions and examples of the derivatives of the compounds to be prepared are the same.

  Examples of the polymer compound used for forming the intermediate layer include polymer compounds P-21 to P-26 in Table 7 below. Here, the “other” structural unit refers to the structural unit represented by the formula (Y), the structural unit represented by the formula (5), and the structure of the phosphorescent compound represented by the formula (1-A). It means a structural unit other than the structural unit it has.

［表中、ｐ、ｑ、ｒ、ｓおよびｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝１００であり、かつ、１００≧ｐ＋ｑ＋ｒ＋ｓ≧７０である。その他の構成単位とは、式(Y)で表される構成単位、式(5)で表される構成単位および式(1-A)で表される燐光発光化合物の構造を有する構成単位以外の構成単位を意味する。］

[In the table, p, q, r, s and t represent the molar ratio of each constituent unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70. Other structural units are structural units represented by the formula (Y), structural units represented by the formula (5), and structural units other than the structural units having the structure of the phosphorescent compound represented by the formula (1-A) A structural unit. ]

<Method for producing polymer compound>
Next, the manufacturing method of a high molecular compound is demonstrated.

The polymer compound used in the light-emitting device of the present invention is, for example, at least one selected from the group consisting of a compound represented by the following formula (M-Y1) and a compound represented by the following formula (M-4). Compound, a compound represented by the following formula (M-Y2), a compound represented by the following formula (MX), a compound represented by the following formula (M-2), and a compound represented by the following formula (M-3) Selected from the group consisting of a compound represented by the following formula (M-3 ′), a compound represented by the following formula (M-5), and a compound represented by the following formula (M-PB ^1-A ) It can be produced by condensation polymerization of at least one compound. In this specification, the compounds used for the production of the polymer compound are sometimes collectively referred to as “raw material monomers”.

［式中、
Ａｒ^Y1、Ａｒ^X1〜Ａｒ^X4、Ｒ^X1〜Ｒ^X3、ａ^X1、ａ^X2、Ａｒ²、Ａｒ³、Ｌ^Ａ、ｎＡ、Ｘ、ｎ、Ａｒ⁴〜Ａｒ⁶、Ｋ^Ａ、ｍＡ、Ｘ’、ｍ、ｃ、Ａｒ⁷、Ｒ³、ｐ³、Ｌ^ＢおよびＸ’’は、前記と同じ意味を表す。
Ｚ^C1〜Ｚ^C18は、それぞれ独立に、置換基Ａ群および置換基Ｂ群からなる群から選ばれる基を表す。
ＰＢ^１−Ａは、式（１−Ａ）で表される燐光発光性化合物から水素原子を２個取り除いた基を表す。］

[Where:
Ar ^Y1 , Ar ^{X1 to} Ar ^X4 , R ^{X1 to} R ^X3 , a ^X1 , a ^X2 , Ar ² , Ar ³ , L ^A , nA, X, n, Ar ^{4 to} Ar ⁶ , K ^A , mA, X ′, ^{m, c, Ar 7, R} 3, p 3, L B and X '' are as defined above.
Z ^{C1 to} Z ^C18 each independently represent a group selected from the group consisting of the substituent group A and the substituent group B.
PB ^1-A represents a group obtained by removing two hydrogen atoms from the phosphorescent compound represented by the formula (1-A). ]

For example, when Z ^C1 , Z ^C2 , Z ^C13 and Z ^C14 are groups selected from the substituent group A, Z ^{C3 to} Z ^C12 and Z ^{C15 to} Z ^C18 select groups selected from the substituent group B. .
For example, when Z ^C1 , Z ^C2 , Z ^C13 and Z ^C14 are groups selected from the substituent group B, Z ^{C3 to} Z ^C12 and Z ^{C15 to} Z ^C18 select a group selected from the substituent group A. .

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

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

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

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

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

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

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

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

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

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

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

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

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

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

<Layer structure of light emitting element>
The light emitting element of the present invention may have a layer other than the anode, the cathode, the light emitting layer, the hole transport layer and the intermediate layer (hereinafter also referred to as “other layer”). Examples of other layers include a hole injection layer, an electron transport layer, and an electron injection layer.
The light emitting layer, the hole transport layer, and the intermediate layer can be formed using the above-described light emitting layer material, the above hole transport layer material, and the above intermediate layer material, respectively. (For example, a light emitting material and a hole transport material) may be used in combination.
The hole injection layer, the electron transport layer, and the electron injection layer include a hole injection material, an electron transport material, and an electron injection material, respectively, and can be formed using the hole injection material, the electron transport material, and the electron injection material, respectively. it can.

  The light-emitting material that may be used in combination with the above-described light-emitting layer material, the hole transport material that may be used in combination with the above-described material of the hole transport layer, the hole injection material, the electron transport material, and the electron injection material will be described later. To do.

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

  The thickness of the light emitting layer, hole transport layer, intermediate layer, hole injection layer, electron transport layer and electron injection layer is usually 1 nm to 10 μm.

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

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

  The light emitting layer, the hole transport layer, the intermediate layer, the hole injection layer, the electron transport layer, and the electron injection layer are the materials for the light emitting layer described above, the materials for the hole transport layer described above, the materials for the intermediate layer described above, and holes. Using inks each containing injection material, electron transport material and electron injection material, for example, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, It can be produced by a dip coating method, a spray coating method, a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, or a nozzle coating 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, bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, benzophenone, acetophenone; ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, phenyl acetate, etc. Ester solvent: Ethylene Polyhydric alcohol solvents such as glycol, glycerin and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone and N, N-dimethyl Examples include amide solvents such as formamide. A solvent may be used individually by 1 type, or may use 2 or more types together.

  In the ink, the blending amount of the solvent is based on 100 parts by weight of the light emitting layer material, the hole transport layer material, the intermediate layer material, the hole injection material, the electron transport material, or the electron injection material. The amount is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight.

  The material of the hole transport layer, the material of the intermediate layer, the material of the electron transport layer and the material of the light emitting layer are the layers adjacent to the hole transport layer, the intermediate layer, the electron transport layer and the light emitting layer, respectively, in the production of the light emitting device. In the case of being dissolved in the solvent used at the time of forming, it is preferable that the material 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.

  The heating temperature for crosslinking each layer is usually 25 to 300 ° C., and the luminance life of the light emitting device of the present invention is excellent. Therefore, the heating temperature is preferably 50 to 250 ° C., more preferably 150 to 200 ° C. .

  The kind of light used for light irradiation for cross-linking each layer is, for example, ultraviolet light, near ultraviolet light, or visible light.

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

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

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

  [Luminescent material]

  Examples of the light-emitting material that may be used in combination with the above-described light-emitting layer materials include, for example, naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal. Is mentioned.

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

[Hole transport material]
Examples of the hole transport material that may be used in combination with the material of the hole transport layer described above include polyvinyl carbazole and derivatives thereof. The hole transport material may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone, and fullerene is preferable.

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

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

  Low molecular weight compounds include, for example, metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene and diphenoquinone. As well as these derivatives.

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

  When the light-emitting element of the present invention includes an electron transport layer, the electron transport layer is selected from the group consisting of a structural unit represented by the formula (ET-1) and a structural unit represented by the formula (ET-2). A layer obtained using a polymer compound containing at least one kind of structural unit (hereinafter also referred to as polymer compound (P3)) is preferable.

“Obtained using” in relation to the relationship between the electron transport layer and the polymer compound (P3) means that the electron transport layer is formed using the polymer compound (P3).
The polymer compound (P3) may be contained in the electron transport layer as it is, or the polymer compound (P3) is crosslinked in the molecule, between the molecules, or both (crosslinked product). The polymer compound (P3) is preferably contained in the electron transport layer as it is.

［式中、
ｎＥ１は、１以上の整数を表す。
Ａｒ^Ｅ１は、芳香族炭化水素基または複素環基を表し、これらの基はＲ^Ｅ１以外の置換基を有していてもよい。
Ｒ^Ｅ１は、式（ＥＳ−１）で表される基を表す。Ｒ^Ｅ１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:
nE1 represents an integer of 1 or more.
Ar ^E1 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent other than R ^E1 .
R ^E1 represents a group represented by the formula (ES-1). When a plurality of R ^E1 are present, they may be the same or different. ]

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

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

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

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

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

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

R ^E3 is preferably an arylene group.

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

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

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

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

^Examples of the substituent that R ^E3 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3). R ^E3 preferably has a group represented by the formula (ES-3) as a substituent because the light-emitting efficiency of the light-emitting element of the present invention is excellent.

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

［式中、Ｍ^＋は、Ｌｉ^＋、Ｎａ^＋、Ｋ^＋、Ｃｓ^＋、Ｎ（ＣＨ_３）_４ ^＋、ＮＨ（ＣＨ_３）_３ ^＋、ＮＨ_２（ＣＨ_３）_２ ^＋またはＮ（Ｃ_２Ｈ_５）_４ ^＋を表す。］

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

［式中、
ｎＥ２は１以上の整数を表す。
Ａｒ^Ｅ２は、芳香族炭化水素基または複素環基を表し、これらの基はＲ^Ｅ２以外の置換基を有していてもよい。
Ｒ^Ｅ２は、式（ＥＳ−２）で表される基を表す。Ｒ^Ｅ２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:
nE2 represents an integer of 1 or more.
Ar ^E2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent other than R ^E2 .
R ^E2 represents a group represented by the formula (ES-2). When a plurality of R ^E2 are present, they may be the same or different. ]

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

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

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

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

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

R ^E6 is preferably an arylene group.

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

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

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

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

^Examples of the substituent that R ^E6 may have include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, and a group represented by the formula (ES-3). R ^E6 preferably has a group represented by the formula (ES-3) as a substituent because the light-emitting efficiency of the light-emitting element of the present invention is excellent.

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

［式中、Ｘ⁻は、Ｆ⁻、Ｃｌ⁻、Ｂｒ⁻、Ｉ⁻、テトラフェニルボレート、ＣＦ_３ＳＯ_３ ⁻、またはＣＨ_３ＣＯＯ⁻を表す。］

[Wherein, X ⁻ represents F ⁻ , Cl ⁻ , Br ⁻ , I ⁻ , tetraphenyl borate, CF ₃ SO ₃ ⁻ , or CH ₃ COO ⁻ . ]

  As a structural unit represented by Formula (ET-1) and Formula (ET-2), the structural unit represented by the following formula (ET-31)-Formula (ET-34) is mentioned, for example.

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

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

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

  Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; a group represented by the formula (X) is included in the main chain or side chain Examples thereof include conductive polymers such as polymers.

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

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

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

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

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

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

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

[Measurement condition]
The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 μL was injected into SEC. Tetrahydrofuran was used as the mobile phase of SEC and flowed at a flow rate of 2.0 mL / min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.

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

NMR measurement was performed by the following method.
5 to 10 mg of a measurement sample was dissolved in about 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran (THF-d ₈ ), or methylene dichloride (CD ₂ Cl ₂ ), and an NMR apparatus (Varian, Inc. ), Trade name: INOVA 300 or trade name: MERCURY 400VX).

TLC-MS was measured by the following method.
The sample to be measured is dissolved in toluene, tetrahydrofuran or chloroform and applied onto a DART TLC plate (Techno Applications YSK5-100), and TLC-MS (manufactured by JEOL Ltd., trade name: JMS-T100TD) (The AccuTOF TLC)). The helium gas temperature during measurement was adjusted in the range of 200 to 400 ° C.

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

In this example, the maximum peak wavelength of the emission spectrum of the phosphorescent compound was measured at room temperature with a spectrophotometer (manufactured by JASCO Corporation, FP-6500). A xylene solution prepared by dissolving a phosphorescent compound in xylene at a concentration of about 0.8 × 10 ⁻⁴ wt% was used as a sample. As excitation light, UV light having a wavelength of 325 nm was used.

<Synthesis Example 1> Synthesis of Metal Complex EM1 Metal complex EM1 was synthesized according to the method described in JP2013-147551A. The maximum peak wavelength of the emission spectrum of the metal complex EM1 was 475 nm.

  Polymer compound HP, polymer compound P1, polymer compound P2-1, polymer compound P2-2, polymer compound P2-3, polymer compound P2-4, polymer compound P2-5, polymer compound E1 and The structures of the monomers CM1 to CM15 used in the synthesis of the polymer compound E2 are shown below.

Monomers CM1 to CM15 were synthesized according to the following method, and those having an HPLC area percentage value of 99.5% or more were used.
Monomer CM1 was synthesized according to the method described in JP 2010-189630 A.
Monomer CM2 was synthesized according to the following method.
Monomer CM3 was synthesized according to the following method.
Monomer CM4 was synthesized according to the method described in JP2011-174062.
Monomer CM5 was synthesized according to the method described in WO2002 / 045184.
Monomer CM6 was synthesized according to the method described in WO2005 / 049546.
Monomer CM7 was synthesized according to the method described in JP-A-2008-106241.
Monomer CM8 was recrystallized from a purchased reagent (Aldrich product).
Monomer CM9 was synthesized according to the method described in JP 2010-215886 A.
Monomer CM10 was synthesized according to the method described in International Publication No. 2013/146806.
Monomer CM11 was synthesized according to the method described in International Publication No. 2013/146806.
Monomer CM12 was synthesized according to the following method.
Monomer CM13 was synthesized according to the following method.
Monomer CM14 was synthesized according to the following method.
Monomer CM15 was synthesized according to the method described in JP 2012-33845 A.

<Synthesis Example 2> Synthesis of Monomer CM2

３００ｍＬの三口フラスコに、国際公開第２００９／１３１２５５号に記載の方法に従って合成した化合物ＣＣ１（７．４ｇ，１０ｍｍｏｌ）、２−ヨード−５−ブロモ−ｍ−キシレン（９．３ｇ，３０ｍｍｏｌ）およびテトラキストリフェニルホスフィンパラジウム（０）（０．２３ｇ，０．０４ｍｍｏｌ）を加え、三口フラスコ内の気体をアルゴンガスで置換した。その後、それぞれ予め１０分間アルゴンガスをバブリングすることにより溶存酸素を除去したトルエン（６０ｍＬ）、テトラヒドロフラン（３０ｍＬ）、ｔｅｒｔ−ブタノール（４０ｍＬ）およびイオン交換水（２０ｍＬ）を室温にて加え、その後、２０重量％テトラエチルアンモニウムヒドロキシド水溶液（３０ｇ，８ｍｍｏｌ）を更に加え、５０℃で１２時間攪拌した。得られた反応溶液に、イオン交換水およびトルエンを加え、攪拌、静置した後に、分液を行った。得られた有機層を無水硫酸ナトリウムにより乾燥させ、無機塩をろ別した。得られたろ液から溶媒を減圧留去した後に、アセトニトリルを加え、７０℃で３０分間攪拌し、室温まで冷却し、析出した固体をろ過により取り出した。得られた固体を中圧シリカゲルカラムクロマトグラフィー（ヘキサン／クロロホルム＝１５／１（ｖ／ｖ（体積比であることを示す。以下同様。））により精製し、更に、再結晶（クロロホルム／アセトニトリル＝４／７（ｖ／ｖ））により精製し、減圧乾燥することにより、目的物である化合物ＣＭ２（４．７２ｇ）を白色固体として得た。収率は５５％であった。また、得られた化合物ＣＭ２のＨＰＬＣ面積百分率値は９９．５％以上を示した。必要に応じて、上記の操作を繰り返し行った。

In a 300 mL three-necked flask, compound CC1 (7.4 g, 10 mmol), 2-iodo-5-bromo-m-xylene (9.3 g, 30 mmol) and tetrakis synthesized according to the method described in International Publication No. 2009/131255. Triphenylphosphine palladium (0) (0.23 g, 0.04 mmol) was added, and the gas in the three-necked flask was replaced with argon gas. Thereafter, toluene (60 mL), tetrahydrofuran (30 mL), tert-butanol (40 mL) and ion-exchanged water (20 mL) from which dissolved oxygen was removed by bubbling argon gas for 10 minutes in advance were added at room temperature, and then 20 A weight% aqueous tetraethylammonium hydroxide solution (30 g, 8 mmol) was further added, and the mixture was stirred at 50 ° C. for 12 hours. Ion exchange water and toluene were added to the obtained reaction solution, and the mixture was stirred and allowed to stand, followed by liquid separation. The obtained organic layer was dried with anhydrous sodium sulfate, and the inorganic salt was filtered off. After the solvent was distilled off under reduced pressure from the obtained filtrate, acetonitrile was added, the mixture was stirred at 70 ° C. for 30 minutes, cooled to room temperature, and the precipitated solid was taken out by filtration. The obtained solid was purified by medium pressure silica gel column chromatography (hexane / chloroform = 15/1 (v / v (indicating volume ratio; the same applies hereinafter))), and further recrystallized (chloroform / acetonitrile = 4/7 (v / v)) and dried under reduced pressure to obtain the target compound CM2 (4.72 g) as a white solid in a yield of 55%. The compound CM2 showed an HPLC area percentage value of 99.5% or more, and the above operation was repeated as necessary.

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.82 (d, 2H), 7.23 (m, 4H), 7.17 (s, 2H), 7.12-7.07 (M, 6H), 699-6.95 (m, 4H), 2.52 (t, 4H), 1.95 (s, 12H), 1.59-1.45 (m, 4H), 1.32-1.18 (m, 12H), 0.85 (t, 6H).
LC / MS (ESI-MS (posi)): 850 [M] ⁺

<Synthesis Example 3> Synthesis of Monomer CM3

(First step)
After making the gas in the reaction vessel an argon gas atmosphere, compound CC2 (41.77 g, 120 mmol) synthesized according to the method described in JP 2010-189630 A, bis (pinacol) diboron (91.9 g, 362 mmol), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) dichloromethane complex (1: 1) (Pd (dppf) Cl ₂ .CH ₂ Cl ₂ , CAS No. 95464-05-4, Sigma- While a mixture of Aldrich Co. LLC, 5.096 g, 6.24 mmol), potassium acetate (70.67 g, 720 mmol) and 1,4-dioxane (commercial dehydrated product, 500 mL) was heated in an oil bath at 80 ° C. After stirring for about 8 hours, dilute with toluene (500 mL) The insolubles were removed by passed through a write and silica gel pad, and then to obtain a solid by distilling off the solvent. Methanol (750 mL) was added to the resulting solid and stirred well, then the solid was removed by filtration and dried under reduced pressure to obtain a solid (57 g). The obtained solid was dissolved in hexane, activated carbon was added, and the mixture was stirred for 1 hour while heating in an oil bath at 60 ° C., then insoluble matters were removed by Celite filtration, and then the solvent was distilled off to obtain a white solid. Got. Methanol (750 mL) was added to the obtained solid, stirred for 1 hour while heating to 50 ° C., and then cooled to room temperature. The precipitated solid was taken out by filtration and dried under reduced pressure to give compound CC2a ( 40.59 g) was obtained. The yield was 76%. The obtained compound CC2a showed 99.5% or more by HPLC area percentage value (UV254 nm).

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 8.75 (d, 4H), 8.68 (d, 2H), 8.06 (d, 4H), 7.39 (d, 2H ), 2.73 (t, 2H), 1.71-1.60 (m, 2H), 1.50-1.20 (m, 42H), 0.88 (t, 3H).
TLC / MS (DART, posi): [M + H] ⁺ = 730.49

(Second step)
After making the gas in the reaction vessel an argon gas atmosphere, compound CC2a (25.54 g, 35 mmol), 5-iodo-2-bromo-m-xylene (32.65 g, 105 mmol), toluene (210 mL), tert-butanol (140 mL), tetrahydrofuran (105 mL), ion-exchanged water (70 mL), 20 wt% tetraethylammonium hydroxide aqueous solution (103.1 g, 140 mmol) and tetrakis (triphenylphosphine) palladium (0) (2.45 g, 2.12 mmol) The mixture was stirred for 40 hours while heating in an oil bath set at 40 ° C., cooled to room temperature, toluene (140 mL) and ion-exchanged water (140 mL) were added, and an organic layer was obtained by liquid separation. The obtained organic layer was washed with 5% by weight brine, dried over anhydrous magnesium sulfate, the solid obtained was removed by filtration, and the solvent was evaporated by concentration under reduced pressure to give a brown oil (37 g). ) The obtained brown oil was diluted with toluene, passed through a silica gel short column, and the solvent was distilled off by concentration under reduced pressure to obtain a yellow oil. The resulting yellow oil was purified by medium pressure silica gel column chromatography (hexane), and the fraction containing the desired product was concentrated under reduced pressure, and then purified by recrystallization (a mixed solvent of toluene and methanol). By drying under reduced pressure, Compound CM3 (6.15 g) was obtained. The yield was 21%. The obtained compound CM3 had an HPLC area percentage value of 99.5% or more.

¹ H-NMR (300 MHz, CD ₂ Cl ₂ ): δ (ppm) = 8.86 (d, J = 8.3 Hz, 4H), 8.72 (d, J = 8.3 Hz, 2H), 7. 43 (d, J = 8.3 Hz, 2H), 7.37 (d, J = 8.3 Hz, 4H), 7.32 (s, 4H), 2.75 (t, J = 7.7 Hz, 2H) ), 2.07 (s, 12H), 1.75-1.66 (multit, 2H), 1.42-1.22 (multit, 18H), 0.88 (t, J = 6.6 Hz, 3H) ).
TLC / MS (DART, posi): [M + H] ⁺ = 842.27

<Synthesis Example 4> Synthesis of Monomer CM12

(First step)
The reaction vessel was filled with a nitrogen gas atmosphere, and then synthesized according to the method described in Iridium Chloride Hydrate (67.0 g), Chemistry Material (Chem. Mater.), Vol. 18, 5119-5129 (2006). Compound L1 (128 g), 2-ethoxyethanol (570 mL) and water (190 mL) were added, and the mixture was stirred at 100 ° C. for 18 hours.
Then, it cooled to 15 degreeC, water was added, and the depositing solid was filtered. The obtained solid was washed successively with water and hexane and then dried under reduced pressure to obtain Compound CM12a (142 g, yield 95%, yellow powder).

(Second step)
After making the inside of the reaction vessel a nitrogen gas atmosphere, Compound CM12a (142 g), Compound L1 (252), Silver Trifluoromethanesulfonate (46.3 g) and diglyme (360 mL) were added and stirred at 150 ° C. for 21 hours.
The reaction mixture was cooled and then filtered, and the resulting filtrate was concentrated under reduced pressure. Water was added thereto, and the precipitated solid was collected by filtration. The obtained solid was washed successively with water and methanol, and then dried under reduced pressure to obtain a crude product.
The obtained crude product was purified in turn by silica gel column chromatography (dichloromethane / ethyl acetate) and recrystallization (dichloromethane / methanol), and then dried under reduced pressure to obtain Compound CM12b (158 g, 85% yield, yellow powder). Obtained. The HPLC area percentage value of Compound CM12b was 99.1%.

(Third process)
After making the inside of the reaction vessel a nitrogen gas atmosphere, compound CM12b (113 g), compound L2 (103 g) and toluene (1100 mL), aqueous sodium carbonate (2 mol / L, 264 mL) and tetrakis (triphenylphosphine) palladium (0) ( 6.36 g) was added and the mixture was stirred at 70 ° C. for 7 hours.
After cooling the reaction mixture, the aqueous layer was removed, and the resulting organic layer was washed with brine. The obtained organic layer was concentrated under reduced pressure to obtain a crude product.
The obtained crude product was purified in turn by silica gel column chromatography (hexane / dichloromethane) and recrystallization (dichloromethane / methanol), and then dried under reduced pressure to give compound CM12c (61.8 g, yield 36%, yellow powder). Got. The HPLC area percentage value of Compound CM12c was 86.5%.

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

(Fourth process)
After making the inside of the reaction vessel a nitrogen gas atmosphere, compound CM12c (61.8 g), bis (pinacolato) diboron (30.2 g), potassium acetate (11.7 g), 1,4-dioxane (dehydrated product, 398 mL) and Add [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) dichloromethane complex (Pd (dppf) Cl ₂ .CH ₂ Cl ₂ , 0.65 g) and stir at 100 ° C. for 5.5 hours. did.
The reaction mixture was cooled to room temperature and then filtered, and the obtained filtrate was concentrated to obtain a crude product.
The resulting crude product was purified by silica gel column chromatography (hexane / ethyl acetate) and then dried under reduced pressure to obtain Compound CM12d (47.9 g, yield 75%, yellow powder).

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

(Fifth process)
After making the inside of the reaction vessel a nitrogen gas atmosphere, Compound CM12d (45.7 g), 1,3,5-tribromobenzene (45.0 g), toluene (571 mL), aqueous sodium carbonate solution (1 mol / L, 86 mL), Methyl trioctyl ammonium chloride (manufactured by Sigma Aldrich, trade name Aliquat 336) (0.35 g) and tetrakis (triphenylphosphine) palladium (0) (1.65 g) were added, and the mixture was stirred at 110 ° C. for 3 hours.
After cooling the reaction mixture, the aqueous layer was removed, and the resulting organic layer was washed with brine. The obtained organic layer was concentrated under reduced pressure to obtain a crude product.
The obtained crude product was purified in turn by silica gel column chromatography (hexane / ethyl acetate), recrystallization (toluene / methanol), and recrystallization (ethyl acetate / methanol), and then dried under reduced pressure to give compound CM12 (31.31). 6 g, yield 65%, yellow powder).
The HPLC area percentage value of Compound CM12 was 99.5% or more.

¹ H-NMR (CDCl ₃ -d, 300 MHz): δ (ppm) = 7.82 (s, 2H), 7.74 (d, 6H), 7.64-7.56 (m, 12H), 7 .49 (d, 8H), 7.21-7.17 (m, 2H), 7.00 (d, 1H), 6.87 (d, 2H), 6.77 (d, 1H), 4. 30 (s, 3H), 4.26 (s, 6H), 2.30-2.20 (m, 3H), 2.05-1.88 (m, 3H), 1.40-1.16 ( m, 42H), 0.70 (t, 9H).

LC-MS (UV254 nm-APCI positive): m / z ⁺ = 1706.6 [M + H] ⁺

<Synthesis Example 5> Synthesis of Monomer CM13

(First step)
After the reaction vessel was filled with a nitrogen gas atmosphere, monomer CM7 (96.41 g, 182 mmol), bis (pinacol) diboron (139.3 g, 547 mmol), [1,1′-bis (diphenylphosphino) ferrocene] Dichloropalladium (II) dichloromethane complex (1: 1) (Pd (dppf) Cl ₂ · CH ₂ Cl ₂ , CAS No. 95464-05-4, Sigma-Aldrich Co. LLC, 14.9 g, 18.3 mmol) , Potassium acetate (107.5 g, 1095 mmol) and 1,4-dioxane (commercially dehydrated product, 550 mL) were added, and the mixture was stirred at 80 ° C. for 6 hours. Thereafter, toluene (850 mL) was added thereto, and the solution was passed through a celite and silica gel pad to remove insoluble matters. Thereafter, the solvent was distilled off to obtain a solid. The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred at 60 ° C. for 1 hour. Then, the insoluble matter was removed by passing through Celite. Thereafter, the solvent was distilled off to obtain a solid. Thereafter, the product was purified by recrystallization (acetonitrile) and dried under reduced pressure to obtain the target compound CM13a (113.7 g, yield 91%) as a white solid. The obtained compound CM13a showed 98.7% in terms of HPLC area percentage (UV254 nm).

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.81 (s, 2H), 7.80 (d, 2H), 7.75 (d, 2H), 7.12 (d, 2H) ), 6.89 (d, 2H), 6.86 (s, 2H), 3.07 (d, 8H), 1.31 (s, 24H).
LC / MS (ESI, posi): [M + K] ⁺ = 661.3

(Second step)
The reaction vessel was filled with a nitrogen gas atmosphere, then compound CM13a (107.7 g, 171 mmol), 5-iodo-2-bromo-m-xylene (159.5 g, 513 mmol), toluene (1000 mL), tert-butanol (700 mL) ), Tetrahydrofuran (500 mL), ion-exchanged water (350 mL), 20 wt% tetraethylammonium hydroxide aqueous solution (500 g, 682 mmol) and tetrakis (triphenylphosphine) palladium (0) (5.0 g, 4.3 mmol) were added, The mixture was stirred at 50 ° C. for 64 hours. After cooling the obtained reaction solution to room temperature, toluene (680 mL) and ion-exchange water (680 mL) were added, and the organic layer was obtained by liquid-separating. The obtained organic layer was washed successively with ion-exchanged water and 10% by weight saline and then dried over anhydrous magnesium sulfate. The obtained solid was removed by filtration, and the solvent was evaporated by concentration under reduced pressure to obtain a yellow oil (212 g). The obtained yellow oil was recrystallized (ethyl acetate / acetonitrile). After purification, it was further purified by silica gel column chromatography (hexane / chloroform). Thereafter, the fraction containing the target product was concentrated under reduced pressure, purified by recrystallization (toluene / acetonitrile), and the resulting solid was dried under reduced pressure to obtain the target compound CM13 (81 g, 61% yield). It was. The obtained compound CM13 showed 99.5% or more by HPLC area percentage value (UV254 nm).

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.81 (d, 2H), 7.24 (s, 4H), 7.17 (s, 2H), 7.11 (d, 2H) ), 7.03 (d, 2H), 6.87 (s, 2H), 6.83 (d, 2H), 3.06 (d, 8H) 1.98 (s, 12H).
LC / MS (ESI, posi): [M + K] ⁺ = 773.1

<Synthesis Example 6> Synthesis of monomer CM14

(First step)
After making the inside of the reaction vessel a nitrogen gas atmosphere, monomer CM9 (85.6 g, 186 mmol) was dissolved in tetrahydrofuran (commercially dehydrated grade product, 1900 mL). Thereafter, the resulting solution was cooled to −78 ° C., and while stirring the solution, a hexane solution of n-butyllithium (1.6 mol / L, 256 mL, 409 mmol) was added dropwise, and the mixture was further stirred for 1 hour. Thereafter, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (96.9 g, 521 mmol) was added dropwise thereto, and the mixture was stirred for 3 hours while raising the temperature to 0 ° C. did. The obtained reaction solution was cooled with an ice bath, and hydrochloric acid (1 mol / L) was added dropwise until the reaction solution showed pH 6-7. Thereafter, toluene was added thereto, the temperature was raised to room temperature, and the aqueous layer was removed by liquid separation. Then, it wash | cleans one by one with ion-exchange water and a 10 weight% salt solution, After drying the obtained organic layer with anhydrous sodium sulfate, the inorganic salt was separated by filtration. The obtained filtrate was concentrated under reduced pressure to obtain a solid. Acetonitrile was added to the obtained solid and stirred, and then the solid was collected by filtration. The obtained solid was dried under reduced pressure to obtain the target compound CM14a (92.2 g, yield 89%) as a white solid. It was. The obtained compound CM14a showed 95.6% in terms of HPLC area percentage (UV254 nm).

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.81 (d, 2H), 7.74 (s, 2H), 7.71 (d, 2H), 5.58-5.47 (M, 2H), 4.81 (d, 2H), 4.77 (s, 2H), 2.05-2.00 (m, 4H), 1.82-1.75 (q, 4H), 1.39 (s, 24H), 0.70-0.60 (m, 4H).
LC / MS (ESI, posi): [M + K] ⁺ = 593.3

(Second step)
After making the inside of the reaction vessel a nitrogen gas atmosphere, Compound CM14a (87.0 g, 157 mmol), 5-iodo-2-bromo-m-xylene (146 g, 471 mmol), toluene (950 mL), tert-butanol (630 mL), Tetrahydrofuran (480 mL), ion-exchanged water (320 mL), 20 wt% tetraethylammonium hydroxide aqueous solution (460 g, 625 mmol) and tetrakis (triphenylphosphine) palladium (0) (3.6 g, 3.1 mmol) were added, and 50 ° C. For 22 hours. After cooling the obtained reaction solution to room temperature, toluene (620 mL) and ion-exchanged water (620 mL) were added and liquid-separated to obtain an organic layer. The obtained organic layer was washed successively with ion-exchanged water and 10% by weight saline and then dried over anhydrous magnesium sulfate. After removing the obtained solid by filtration, the solvent was distilled off by concentration under reduced pressure. Then, the silica gel column chromatography (hexane / chloroform) refine | purified and the fraction containing the target object was obtained. The obtained fraction was concentrated under reduced pressure, purified by recrystallization (toluene / acetonitrile), further purified by recrystallization (chloroform / acetonitrile), and the obtained solid was dried under reduced pressure to obtain Compound CM14 (51 g, yield). 49%). The obtained compound CM14 showed 99.5% or more in HPLC area percentage value (UV254 nm).

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.77 (d, 2H), 7.29 (s, 4H), 7.09 (s, 2H), 7.06 (d, 2H) ), 5.58-4.45 (m, 2H), 4.83 (d, 2H), 4.78 (s, 2H), 2.04 (s, 12H), 2.04-1.95 ( m, 4H), 1.83-1.76 (q, 4H), 0.82-0.72 (m, 4H).
LC / MS (ESI, negative): [M + Cl] ⁻ = 701.1

<Synthesis Example 7: Synthesis of Polymer Compound HP1>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (1.9735 g, 3.96 mmol), Compound CM2 (1.7739 g, 2.08 mmol), Compound CM3 (1.6200 g, 1.92 mmol) ), Dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (7.1 mg, 0.008 mmol) and toluene (85 ml) were mixed and heated to 100 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (13.6 ml) was added dropwise to the reaction solution, and the mixture was refluxed for 4 hours.
(Step 3) After the reaction, phenylboronic acid (97.5 mg, 0.80 mmol), 20 wt% tetraethylammonium hydroxide aqueous solution (13.6 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( 3.5 mg, 0.004 mmol) was added and refluxed for 19 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with 3.6% by weight hydrochloric acid, twice with 2.5% by weight ammonia water and six times with ion-exchanged water, and when the resulting solution was added dropwise to methanol, precipitation occurred. occured. 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 3.21 g of the polymer compound HP1. The Mn of the polymer compound HP1 was 9.8 × 10 ⁴ and the Mw was 2.7 × 10 ⁵ .

  The theoretical value obtained from the amount of charged raw materials for the polymer compound HP1 is 50: a structural unit derived from the compound CM1, a structural unit derived from the compound CM2, and a structural unit derived from the compound CM3. It is a copolymer composed of a molar ratio of 26:24.

<Synthesis Example 8: Synthesis of polymer compound P1>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM4 (2.6882 g, 2.96 mmol), Compound CM5 (0.4245 g, 0.75 mmol), Compound CM6 (1.6396 g, 1.80 mmol) ), Compound CM7 (0.2377 g, 0.45 mmol), dichlorobis (triphenylphosphine) palladium (2.1 mg, 0.003 mmol) and toluene (62 ml) were added and heated to 105 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (10 ml) was added dropwise to the reaction solution, and the mixture was refluxed for 4.5 hours.
(Step 3) After the reaction, phenylboronic acid (36.8 mg, 0.30 mmol) and dichlorobis (triphenylphosphine) palladium (2.1 mg, 0.003 mmol) were added thereto and refluxed for 16.5 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation. 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 polymer compound P1. The Mn of the polymer compound P1 was 7.8 × 10 ⁴ and the Mw was 2.6 × 10 ⁵ .

  The theoretical value obtained from the amount of charged raw materials for the polymer compound P1 is that the structural unit derived from the compound CM4, the structural unit derived from the compound CM5, the structural unit derived from the compound CM6, and the compound CM7 The derived structural unit is a copolymer composed of a molar ratio of 50: 12.5: 30: 7.5.

<Synthesis Example 9: Synthesis of Polymer Compound P2-1>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (2.4668 g, 4.95 mmol), Compound CM7 (0.2641 g, 0.50 mmol), Compound CM8 (1.0558 g, 4.00 mmol) ), Compound CM9 (0.2301 g, 0.50 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (4.4 mg, 0.005 mmol) and toluene (32 ml) were added and heated to 100 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (17.0 ml) was added dropwise to the reaction solution, and the mixture was refluxed for 4 hours.
(Step 3) After the reaction, phenylboronic acid (121.9 mg, 1.00 mmol), 20 wt% tetraethylammonium hydroxide aqueous solution (17.0 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( 4.4 mg, 0.005 mmol) was added and refluxed for 19 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with 3.6% by weight hydrochloric acid, twice with 2.5% by weight ammonia water and six times with ion-exchanged water, and when the resulting solution was added dropwise to methanol, precipitation occurred. occured. 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 1.65 g of polymer compound P2-1.
The Mn of the polymer compound P2-1 was 7.1 × 10 ⁴ and the Mw was 3.6 × 10 ⁵ .

  The polymer compound P2-1 has the theoretical values determined from the amounts of the raw materials charged, the structural unit derived from the compound CM1, the structural unit derived from the compound CM7, the structural unit derived from the compound CM8, and the compound. The structural unit derived from CM9 is a copolymer composed of a molar ratio of 50: 5: 40: 5.

<Synthesis Example 10: Synthesis of Polymer Compound P2-2>
(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (1.1347 g, 2.28 mmol), Compound CM2 (1.5692 g, 1.84 mmol), Compound CM7 (0.1215 g, 0.230 mmol) ), Compound CM9 (0.1059 g, 0.23 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.1 mg, 0.0023 mmol) and toluene (45 ml) were added and heated to 100 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (7.8 ml) was added dropwise to the reaction solution and refluxed for 3.5 hours.
(Step 3) After the reaction, phenylboronic acid (0.0561 g, 0.46 mmol), 20 wt% tetraethylammonium hydroxide aqueous solution (7.8 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( 2.0 mg, 0.0023 mmol) was added and refluxed for 19 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with 3.6% by weight hydrochloric acid, twice with 2.5% by weight ammonia water and six times with ion-exchanged water, and when the resulting solution was added dropwise to methanol, precipitation occurred. occured. 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 1.74 g of polymer compound P2-2.
The Mn of the polymer compound P2-2 was 1.3 × 10 ⁵ and the Mw was 5.1 × 10 ⁵ .

  The polymer compound P2-2 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound CM1, a structural unit derived from the compound CM2, a structural unit derived from the compound CM7, and a compound. The structural unit derived from CM9 is a copolymer composed of a molar ratio of 50: 40: 5: 5.

<Example 1: Synthesis of polymer compound P2-3>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (0.7538 g, 1.51 mmol), Compound CM8 (0.4685 g, 1.78 mmol), Compound CM10 (0.3373 g, 0.50 mmol) ), Compound CM11 (0.2472 g, 0.50 mmol), compound CM12 (1.2389 g, 0.73 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.4 mg, 0.0025 mmol) and toluene ( 44 ml) was added and heated to 100 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (8.5 ml) was added dropwise to the reaction solution and refluxed for 7.5 hours.
(Step 3) After the reaction, phenylboronic acid (61.0 mg, 0.50 mmol), 20 wt% tetraethylammonium hydroxide aqueous solution (8.5 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( 2.2 mg, 0.0025 mmol) was added and refluxed for 15.5 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with 3.6% by weight hydrochloric acid, twice with 2.5% by weight ammonia water and five times with ion-exchanged water, and when the resulting solution was added dropwise to methanol, precipitation occurred. occured. 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 1.74 g of polymer compound P2-3.
The Mn of the polymer compound P2-3 was 5.5 × 10 ⁴ , and the Mw was 1.4 × 10 ⁵ .

  The polymer compound P2-3 has a theoretical value obtained from the amount of raw materials charged, a structural unit derived from the compound CM1, a structural unit derived from the compound CM8, a structural unit derived from the compound CM10, and a compound. It is a copolymer in which a structural unit derived from CM11 and a structural unit derived from compound CM12 are configured in a molar ratio of 30: 35.5: 10: 10: 14.5.

<Example 2: Synthesis of polymer compound P2-4>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (1.9675 g, 3.95 mmol), Compound CM8 (0.7678 g, 2.91 mmol), Compound CM12 (0.2187 g, 0.13 mmol) ), Compound CM13 (0.3536 g, 0.48 mmol), compound CM14 (0.3209 g, 0.48 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (3.5 mg, 0.004 mmol) and toluene ( 47 ml) was added and heated to 100 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (13.6 ml) was added dropwise to the reaction solution, and the mixture was refluxed for 6.5 hours.
(Step 3) After the reaction, phenylboronic acid (97.5 mg, 0.80 mmol), 20 wt% tetraethylammonium hydroxide aqueous solution (13.6 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( 3.5 mg, 0.004 mmol) was added and refluxed for 15.5 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with 3.6% by weight hydrochloric acid, twice with 2.5% by weight ammonia water, and six times with ion-exchanged water. occured. 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 1.54 g of polymer compound P2-4.
The Mn of the polymer compound P2-4 was 7.8 × 10 ⁴ , and the Mw was 3.7 × 10 ⁵ .

  The polymer compound P2-4 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound CM1, a structural unit derived from the compound CM8, a structural unit derived from the compound CM12, and a compound. A copolymer in which a structural unit derived from CM13 and a structural unit derived from compound CM14 are configured in a molar ratio of 50: 36.4: 1.6: 6: 6.

<Example 3: Synthesis of polymer compound P2-5>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (0.6285 g, 1.26 mmol), Compound CM12 (1.2817 g, 0.75 mmol), Compound CM13 (0.1841 g, 0.25 mmol) ), Compound CM14 (0.1671 g, 0.25 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.1 mg, 0.0013 mmol) and toluene (37 ml) were added and heated to 100 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (8.5 ml) was added dropwise to the reaction solution, and the mixture was refluxed for 9.5 hours.
(Step 3) After the reaction, phenylboronic acid (30.5 mg, 0.25 mmol), 20 wt% tetraethylammonium hydroxide aqueous solution (8.5 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( 1.1 mg, 0.0013 mmol) was added and refluxed for 19 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with 3.6% by weight hydrochloric acid, twice with 2.5% by weight ammonia water and four times with ion-exchanged water, and when the resulting solution was added dropwise to methanol, precipitation was observed. occured. 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 1.52 g of polymer compound P2-5.
The Mn of the polymer compound P2-5 was 8.8 × 10 ⁴ , and the Mw was 3.2 × 10 ⁵ .

  The polymer compound P2-5 has a theoretical value determined from the amount of raw materials charged, a structural unit derived from the compound CM1, a structural unit derived from the compound CM12, a structural unit derived from the compound CM13, and a compound. The structural unit derived from CM14 is a copolymer composed of a molar ratio of 50: 30: 10: 10.

  Table 8 shows the molar ratio of the structural units contained in the polymer compound synthesized above.

<Synthesis Example 11: Synthesis of Polymer Compound E1>

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, monomer CM15 (9.23 g), monomer CM1 (4.58 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (8. 6 mg) and toluene (175 mL) were added and heated to 105 ° C.
(Step 2) Then, a 12 wt% aqueous sodium carbonate solution (40.3 mL) was added dropwise thereto and refluxed for 29 hours.
(Step 3) Thereafter, phenylboronic acid (0.47 g) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (8.7 mg) were added thereto and refluxed for 14 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. When the obtained reaction solution was cooled and dropped into methanol, precipitation occurred. The precipitate was collected by filtration, washed with methanol and water, and then dried, and the solid obtained was dissolved in chloroform and purified by passing through an alumina column and a silica gel column through which chloroform had been passed in advance. When the obtained purified solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain 7.15 g of polymer compound E1.

The polymer compound E1 had a polystyrene-equivalent number average molecular weight of 3.2 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 6.0 × 10 ⁴ .

  The polymer compound E1 includes a structural unit formed from the monomer CM15 and a structural unit formed from the monomer CM1 in a molar ratio of 50:50 according to a theoretical value obtained from the amount of the raw materials charged. It is a copolymer.

<Synthesis Example 12: Synthesis of Polymer Compound E2>

(Step 1) After adding the polymer compound E1 (3.1 g) to the reaction vessel, the inside of the reaction vessel was filled with an argon gas atmosphere. Thereafter, tetrahydrofuran (130 mL) and methanol (66 mL), cesium hydroxide monohydrate (2.1 g) and water (12.5 mL) were added thereto, and the mixture was stirred at 60 ° C. for 3 hours.
(Step 2) Thereafter, methanol (220 mL) was added thereto and stirred for 2 hours. The obtained reaction mixture was concentrated and then added dropwise to isopropyl alcohol, followed by stirring. As a result, precipitation occurred. The precipitate was collected by filtration and dried to obtain polymer compound E2 (3.5 g).

  The polymer compound E2 has a theoretical value calculated from the amount of the raw material charged for the polymer compound E1, and a structural unit represented by the following formula and a structural unit formed from the monomer CM1 are mixed in a 50:50 mole. It is a copolymer containing by ratio.

<Comparative Example CD1> Fabrication and Evaluation of Light-Emitting Element CD1

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

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

(Formation of light emitting layer)
Polymer compound HP1 and metal complex EM1 (polymer compound HP1 / metal complex EM1 = 60 wt% / 40 wt%) were dissolved in xylene at a concentration of 1.6 wt%. Using the obtained xylene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. .

(Formation of cathode)
The substrate on which the light emitting layer is formed is depressurized to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, and then, as a cathode, sodium fluoride is about 4 nm on the light emitting layer, and then on the sodium fluoride layer. Aluminum was deposited at about 80 nm. After vapor deposition, the light emitting element CD1 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting device CD1. Table 9 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Comparative Example CD2> Fabrication and Evaluation of Light-Emitting Device CD2 After the formation of the hole transport layer in Comparative Example CD1, and before the formation of the light-emitting layer, the same procedure as in Comparative Example CD1 was conducted except that an intermediate layer was formed by the following method. Thus, a light emitting device CD2 was manufactured. EL light emission was observed by applying a voltage to the light emitting device CD2. Table 9 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

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

<Example D1> Production and Evaluation of Light-Emitting Element D1 A light-emitting element D1 was produced in the same manner as Comparative Example CD2, except that polymer compound P2-1 was used instead of polymer compound P1 in comparative example CD2. .
EL light emission was observed by applying a voltage to the light emitting element D1. Table 9 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D2> Production and Evaluation of Light-Emitting Element D2 Light-emitting element D2 was produced in the same manner as Comparative Example CD2, except that polymer compound P2-2 was used instead of polymer compound P1 in comparative example CD2. .
EL light emission was observed by applying a voltage to the light emitting element D2. Table 9 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D3> Production and evaluation of light-emitting element D3 Light-emitting element D3 was produced in the same manner as Comparative Example CD2, except that polymer compound P2-3 was used instead of polymer compound P1 in comparative example CD2. .
EL light emission was observed by applying a voltage to the light emitting element D3. Table 9 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D4> Production and Evaluation of Light-Emitting Element D4 A light-emitting element D4 was produced in the same manner as Comparative Example CD2, except that polymer compound P2-4 was used instead of polymer compound P1 in comparative example CD2. .
EL light emission was observed by applying a voltage to the light emitting element D4. Table 9 shows the external quantum yield EQE [%], emission spectrum peak wavelength [nm], and CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D5> Production and Evaluation of Light-Emitting Element D5 Light-emitting element D5 was produced in the same manner as Comparative Example CD2, except that polymer compound P2-5 was used instead of polymer compound P1 in comparative example CD2. .
EL light emission was observed by applying a voltage to the light emitting element D5. Table 9 shows the external quantum yield EQE [%], emission spectrum peak wavelength [nm], and CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Comparative Example CD3> Production and Evaluation of Light-Emitting Element CD3

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

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

(Formation of light emitting layer)
In toluene, 2,8-di (9H-carbazol-9-yl) dibenzo [b, d] thiophene (DCzDBT) (manufactured by Luminescence Technology Corp) and metal complex EM1 (DCzDBT / metal complex EM1 = 75% by weight / 25 % By weight) was dissolved at a concentration of 2.0% by weight. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. .

(Formation of electron transport layer)
The polymer compound E2 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by weight. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride was about 4 nm on the electron transport layer as a cathode, and then the sodium fluoride layer was formed. About 80 nm of aluminum was deposited thereon. After vapor deposition, the light emitting element CD3 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting device CD3. Table 10 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Comparative Example CD4> Production and Evaluation of Light-Emitting Element CD4 After the formation of the hole transport layer in Comparative Example CD3 and before the formation of the light-emitting layer, the same procedure as in Comparative Example CD3 was conducted except that an intermediate layer was formed by the following method. Thus, a light emitting device CD4 was manufactured. EL light emission was observed by applying a voltage to the light emitting device CD4. Table 10 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

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

<Example D6> Production and evaluation of light-emitting element D6 Light-emitting element D6 was produced in the same manner as Comparative Example CD4, except that polymer compound P2-1 was used instead of polymer compound P1 in comparative example CD4. .
EL light emission was observed by applying a voltage to the light emitting element D6. Table 10 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D7> Production and evaluation of light-emitting element D7 Light-emitting element D7 was produced in the same manner as Comparative Example CD4, except that polymer compound P2-3 was used instead of polymer compound P1 in comparative example CD4. .
EL light emission was observed by applying a voltage to the light emitting element D7. Table 10 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D8> Production and evaluation of light-emitting element D8 Light-emitting element D8 was produced in the same manner as Comparative Example CD4 except that polymer compound P2-4 was used instead of polymer compound P1 in comparative example CD4. .
EL light emission was observed by applying a voltage to the light emitting element D8. Table 10 shows the external quantum yield EQE [%], the maximum peak wavelength [nm] of the emission spectrum, and the CIE chromaticity coordinates (x, y) at 100 cd / m ² .

<Example D9> Production and evaluation of light-emitting device D9 Light-emitting device D9 was produced in the same manner as Comparative Example CD4 except that polymer compound P2-5 was used instead of polymer compound P1 in comparative example CD4. .
EL light emission was observed by applying a voltage to the light emitting element D9. Table 10 shows the external quantum yield EQE [%], emission spectrum peak wavelength [nm], and CIE chromaticity coordinates (x, y) at 100 cd / m ² .

  From these results, it can be seen that the light emitting device of the present invention is excellent in external quantum yield.

Claims (14)

The anode,
A cathode,
A light emitting layer provided between the anode and the cathode;
A hole transport layer provided between the anode and the light emitting layer;
In a light emitting device comprising an intermediate layer provided adjacent to the light emitting layer and the hole transport layer between the light emitting layer and the hole transport layer,
A light emitting layer is obtained using the following composition (I), the following composition (II), the following composition (III), the following composition (IV), or the polymer compound (V) below. And a layer containing neither a compound represented by the following formula (Z) nor a derivative of the compound represented by the following formula (Z):
The hole transport layer is a layer obtained using a polymer compound (P1) containing a structural unit represented by the following formula (X),
The intermediate layer is obtained by using a polymer compound (P2) containing a structural unit represented by the following formula (Y), and a compound represented by the following formula (Z) and a compound represented by the following formula (Z). A light-emitting element which is a layer which does not contain any of the derivatives.

(I) A composition containing a phosphorescent compound having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a non-phosphorescent low molecular weight compound having a heterocyclic structure.
(II) A composition containing a high molecular compound containing a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm, and a non-phosphorescent low molecular compound having a heterocyclic structure. object.
(III) A composition comprising a phosphorescent compound having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a polymer compound containing a structural unit represented by the following formula (2).
(IV) a polymer compound including a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm; and a polymer compound including a structural unit represented by the following formula (2): Containing composition.
(V) A polymer compound comprising a structural unit having a phosphorescent compound structure having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm and a structural unit represented by the following formula (2).

[Wherein Ar ² represents 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 are It may have a substituent. ]

[Wherein R ^Z1 represents a monovalent group. A plurality of R ^Z1 may be the same or different. ]

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

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ] The light emitting element of Claim 1 whose said phosphorescent compound is a phosphorescent compound represented by following formula (1).

[Where:
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹ represents an integer of 1 or more, n ² represents an integer of 0 or more, and n ¹ + n ² is 2 or 3. When M is a ruthenium atom, rhodium atom or iridium atom, n ¹ + n ² is 3, and when M is a palladium atom or platinum atom, n ¹ + n ² is 2.
E ¹ and E ² each independently represents a carbon atom or a nitrogen atom. However, at least one of E ¹ and E ² is a carbon atom.
Ring R ¹ represents a 5-membered or 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings R ¹ are present, they may be the same or different. However, if the ring R ¹ is a 6-membered heteroaromatic ring, E ¹ is a carbon atom.
Ring R ² represents a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocyclic ring, and these rings optionally have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings R ² are present, they may be the same or different. However, when the ring R ² is a 6-membered aromatic heterocyclic ring, E ² is a carbon atom.
In addition, when the ring R ¹ is a 6-membered aromatic heterocyclic ring, the ring R ² has an electron withdrawing group.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand, and G ¹ represents an atomic group constituting a bidentate ligand together with A ¹ and A ² . A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ] The light emitting element of Claim 2 whose phosphorescence-emitting compound represented by said Formula (1) is a phosphorescence-emitting compound represented by following formula (1-A).

[Where:
n ^{1, n 2} and ^A 1 ^-G 1 -A ² are as defined above.
M ¹ represents an iridium atom or a platinum atom.
E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are present, they may be the same or different. When E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are nitrogen atoms, R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are present However, it does not have to exist.
R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B , they may be the same or different. R ^2A and R ^3A , R ^3A and R ^4A , R ^2A and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , and R ^4B and R ^5B are bonded to each other, together with the atoms to which they are bonded A ring may be formed.
Ring R ^1A represents a triazole ring or an imidazole ring composed of a nitrogen atom, E ^1A , E ^2A , E ^3A and E ^4A .
Ring R ^1B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^2B , E ^3B , E ^4B and E ^5B . ]   The light emitting element as described in any one of Claims 1-3 whose said light emitting layer is a layer obtained using the composition of said (III). The structural unit represented by the formula (2) is represented by the group represented by the following formula (AA-1), the group represented by the following formula (AA-2), and the following formula (AA-3). The light emitting element as described in any one of Claims 1-4 which is a structural unit which has an at least 1 sort (s) group chosen from the group which consists of group represented by group and a following formula (AA-4).

[Wherein R represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of R are present, they may be the same or different. ]   The light-emitting element according to claim 5, wherein the structural unit represented by the formula (2) is a structural unit having a group represented by the formula (AA-4).   The light emitting element as described in any one of Claims 1-3 whose said light emitting layer is a layer obtained using the composition of said (I). The light emitting element according to claim 7, wherein the non-phosphorescent low molecular weight compound having a heterocyclic structure contained in the composition of (I) is a compound represented by the following formula (H-1).

[Where:
Ar ^H1 and Ar ^H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
n ^H1 and n ^H2 each independently represent 0 or 1. When a plurality of n ^H1 are present, they may be the same or different. A plurality of n ^H2 may be the same or different.
n ^H3 represents an integer of 0 or more.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R ^H11 ) ₂ ] n ^H11 —, and these groups optionally have a substituent. When a plurality of L ^H1 are present, they may be the same or different.
n ^H11 represents an integer of 1 or more and 10 or less. R ^H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of R ^H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
L ^H2 represents a group represented by -N (-L ^H21 -R ^H21 )-. When a plurality of L ^H2 are present, they may be the same or different.
L ^H21 represents a single bond, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. ] The structural unit represented by the said formula (Y) contained in the said high molecular compound (P2) is a structural unit represented by following formula (4), It is as described in any one of Claims 1-8. Light emitting element.

[Where:
Ar ⁷ represents an aromatic hydrocarbon group, and this group may have a substituent other than R ³ .
R ³ represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of R ³ are present, they may be the same or different. Provided that at least one of R ³ binds to a carbon atom adjacent to the carbon atoms forming a bond with the other structural units.
p ³ is an integer of 1 or greater. ] The light emitting device according to any one of claims 1 to 9, wherein the polymer compound (P2) is a polymer compound further comprising a structural unit having at least one kind of crosslinking group selected from the following crosslinking group A group. .
(Crosslinking group A group)

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * Represents a bonding position. These crosslinking groups may have a substituent. ] The light emitting device according to any one of claims 1 to 10, wherein the polymer compound (P1) is a polymer compound further comprising a structural unit represented by the following formula (Y).

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ] The structural unit represented by the said formula (Y) contained in the said high molecular compound (P1) is a structural unit represented by the following formula (Y-1) or (Y-2). Light emitting element.

[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. ]

[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. ] The light emitting device according to any one of claims 1 to 12, wherein the polymer compound (P1) is a polymer compound further comprising a structural unit having at least one crosslinking group selected from the following crosslinking group B group. .
(Bridge group B)

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * Represents a bonding position. These crosslinking groups may have a substituent. ] A structural unit having a structure of a phosphorescent compound represented by the following formula (1-A) having a maximum peak wavelength of an emission spectrum of 400 nm or more and less than 480 nm;
A structural unit represented by the following formula (Y);
A structural unit having at least one crosslinking group selected from the following crosslinking group A group,
The high molecular compound which does not contain the structural unit represented by following formula (X).

[Where:
n ¹ represents an integer of 1 or more, n ² represents an integer of 0 or more, and n ¹ + n ² is 2 or 3. When M is an iridium atom, n ¹ + n ² is 3, and when M is a platinum atom, n ¹ + n ² is 2.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand, and G ¹ represents an atomic group constituting a bidentate ligand together with A ¹ and A ² . A ¹ and A ² each independently represent a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different.
M ¹ represents an iridium atom or a platinum atom.
E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^1A , E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are present, they may be the same or different. When E ^2A , E ^3A , E ^4A , E ^2B , E ^3B , E ^4B and E ^5B are nitrogen atoms, R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are present However, it does not have to exist.
R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, It represents a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^2A , R ^3A , R ^4A , R ^2B , R ^3B , R ^4B and R ^5B , they may be the same or different. R ^2A and R ^3A , R ^3A and R ^4A , R ^2A and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , and R ^4B and R ^5B are bonded to each other, together with the atoms to which they are bonded A ring may be formed.
Ring R ^1A represents a triazole ring or an imidazole ring composed of a nitrogen atom, E ^1A , E ^2A , E ^3A and E ^4A .
Ring R ^1B represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^2B , E ^3B , E ^4B and E ^5B . ]

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ]
(Crosslinking group A group)

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

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