JP2015110751A - Composition and light emitting element prepared using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition useful for the production of a light emitting element having excellent light emitting efficiency.SOLUTION: This invention relates to a composition comprising a compound represented by formula (1) and a phosphorescent compound (Ar1 is a heterocyclic group; D is, for example, a substituent having a structure of a biphenyl derivative substituted with a triazine ring). The phosphorescent compound is an iridium complex represented by the following formula.

Description

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

  As a light-emitting material used for a light-emitting layer of a light-emitting element, various phosphorescent compounds that emit light from a triplet excited state have been studied. As such phosphorescent compounds, many metal complexes in which the central metal is a transition metal belonging to the fifth period or the sixth period have been studied. For example, Patent Document 1 proposes an organometallic dendrimer represented by the following formula, and an electric charge represented by organometallic dendrimer and 4,4-bis (carbazol-9-yl) biphenyl (CBP). A light-emitting element using a guest-host composition containing a transporting low-molecular compound as a light-emitting layer is described.

JP-T-2004-530254

  However, the light emitting device manufactured using the guest-host composition described in Patent Document 1 described above has not obtained sufficient light emission efficiency.

  Then, an object of this invention is to provide a composition useful for manufacture of the light emitting element which is excellent in luminous efficiency. Another object of the present invention is to provide a light-emitting device obtained using the composition.

The present invention, first,
A compound represented by the following formula (1);
At least one selected from the group consisting of a group represented by the following formula (D-1), a group represented by the following formula (D-2), and a group represented by the following formula (D-3). A composition containing a phosphorescent compound having a group is provided.

［式中、
ｍは、２以上の整数を表す。
Ａｒ^１は、複素環基を表し、この基は置換基を有していてもよい。
Ｄは、下記式（Ｄ−１）で表される基、下記式（Ｄ−２）で表される基、または、下記式（Ｄ−３）で表される基を表す。複数存在するＤは、同一でも異なっていてもよい。］

[Where:
m represents an integer of 2 or more.
Ar ¹ represents a heterocyclic group, and this group may have a substituent.
D represents a group represented by the following formula (D-1), a group represented by the following formula (D-2), or a group represented by the following formula (D-3). A plurality of D may be the same or different. ]

［式中、
ｍ^D1、ｍ^D2、ｍ^D3およびｍ^D4は、それぞれ独立に、０以上の整数を表す。複数存在するｍ^D2、ｍ^D3およびｍ^D4は、それぞれ同一でも異なっていてもよい。
Ｇ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。Ｇ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^D1、Ａｒ^D2、Ａｒ^D3およびＡｒ^D4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^D1、Ａｒ^D2、Ａｒ^D3およびＡｒ^D4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。
Ｔ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。複数存在するＴは、同一でも異なっていてもよい。］

[Where:
m ^D1 , m ^D2 , m ^D3 and m ^D4 each independently represent an integer of 0 or more. A plurality of m ^D2 , m ^D3 and m ^D4 may be the same or different.
G represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. When a plurality of G are present, they may be the same or different.
Ar ^D1 , Ar ^D2 , Ar ^D3 and Ar ^D4 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 ^D1 , Ar ^D2 , Ar ^D3 and Ar ^D4 , they may be the same or different.
T represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of T may be the same or different. ]

  Secondly, the present invention provides a light emitting device obtained using the above composition.

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

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.

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

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 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, 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., and preferably has the formula (B-1), (B-2 ), (B-3), (B-4), (B-5), (B-6), (B-7), (B-8), (B-9), (B-10), A group represented by (B-11), (B-12), (B-13), (B-14), (B-15), (B-16) or (B-17).

［式中、これらの基は置換基を有していてもよい。］

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

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

<Composition>
Next, the composition of the present invention will be described. The composition of the present invention comprises a compound represented by formula (1), a group represented by formula (D-1), a group represented by formula (D-2), and the following formula (D-3): And a phosphorescent compound having at least one group selected from the group consisting of groups represented by:

<Compound represented by Formula (1)>
The compound represented by formula (1) will be described.

  M in the formula (1) is an integer of 2 to 6 because the luminous efficiency of the light-emitting device obtained using the composition of the present invention is more excellent and the production of the compound represented by the formula (1) is easy. It is preferable that it is an integer of 2 to 4, more preferably 3 or 4, and particularly preferably 3.

Ar ¹ in formula (1) is preferably a nitrogen-containing heterocyclic group, and more preferably a nitrogen-containing aromatic heterocyclic group. Examples of the nitrogen-containing heterocyclic group include oxadiazole, thiadiazole, thiazole, oxazole, pyrrole, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, phenoxazine, and phenothiazine. Or a group in which two or more hydrogen atoms directly bonded to a hetero atom are removed, and a ring is formed from oxadiazole, thiadiazole, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole or phenoxazine A group in which two or more hydrogen atoms directly bonded to a carbon atom or a hetero atom are removed is preferable, and a ring-forming carbon atom or hetero atom is selected from pyrimidine, triazine, carbazole, or phenoxazine. More preferably, it is a group obtained by removing two or more hydrogen atoms directly bonded to a child, and two hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from triazine, carbazole or phenoxazine. A group excluding the above is more preferable, and a group obtained by removing two or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from triazine is particularly preferable. A group in which two or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring are removed from triazine is a hydrogen atom directly bonded to a carbon atom constituting a ring of 1,3,5-triazine A group formed by removing two or more is preferable.

  D in Formula (1) represents the group represented by Formula (D-1), the group represented by Formula (D-2), or the group represented by Formula (D-3).

m ^D1 , m ^D2 , m ^D3, and m ^D4 are usually an integer of 10 or less, preferably an integer of 5 or less, and more preferably 0 or 1. Further, m ^D1 , m ^D2 , m ^D3 and m ^D4 are preferably the same integer.

  G is preferably a group represented by the formula (GDA-11) to (GDA-15), more preferably represented by the formula (GDA-11), (GDA-14) or (GDA-15). Group, more preferably a group represented by the formula (GDA-11), and these groups optionally have a substituent.

［式中、
＊は、前記式（Ｄ−１）におけるＡｒ^D1、前記式（Ｄ−２）におけるＡｒ^D1もしくはＡｒ^D2、または、前記式（Ｄ−３）におけるＡｒ^D1、Ａｒ^D2もしくはＡｒ^D3との結合を表す。
＊＊は、前記式（Ｄ−１）におけるＡｒ^D2、前記式（Ｄ−２）におけるＡｒ^D2もしくはＡｒ^D3、または、前記式（Ｄ−３）におけるＡｒ^D2、Ａｒ^D3もしくはＡｒ^D4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が複数存在する場合、それらは同一でも異なっていてもよい。］

[Where:
* ^Represents the bond between Ar ^D1 in the formula (D-1), Ar ^D1 or Ar ^D2 in the formula (D-2), or Ar ^D1 , Ar ^D2 or Ar ^D3 in the formula (D-3). Represent.
** represents a bond with Ar ^D2 in the formula (D-1), Ar ^D2 or Ar ^D3 in the formula (D-2), or Ar ^D2 , Ar ^D3 or Ar ^D4 in the formula (D-3). Represents.
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 a plurality of ^RDA are present, 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 ^D1 , Ar ^D2 , Ar ^D3 and Ar ^D4 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 is preferably a group represented by formulas (TDA-1) to (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-1) is preferably a group represented by the formulas (D-1-a) to (D-1-d).

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

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

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

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

  Examples of the group represented by the formula (D-1) include groups represented by the following formulas (D-1-1) to (D-1-18).

R ^p represents a hydrogen atom, an alkyl group or a cycloalkyl group, and the alkyl group is preferably a methyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a 2-ethylhexyloxy group.

  The group represented by the formula (D-2) is preferably a group represented by the formulas (D-2-a) to (D-2-c).

［式中、Ｒ^p1、Ｒ^p2、Ｒ^p3、ｎｐ１、ｎｐ２およびｎｐ３は、前記と同じ意味を表す。］

[Wherein, R ^p1 , R ^p2 , R ^p3 , np1, np2 and np3 represent the same meaning as described above. ]

  Examples of the group represented by the formula (D-2) include groups represented by the following formulas (D-2-1) to (D-2-8).

R ^p represents the same meaning as described above.

  The group represented by the formula (D-3) is preferably a group represented by the formulas (D-3-a) to (D-3-c).

［式中、Ｒ^p1、Ｒ^p2、Ｒ^p3、ｎｐ１、ｎｐ２およびｎｐ３は、前記と同じ意味を表す。］

[Wherein, R ^p1 , R ^p2 , R ^p3 , np1, np2 and np3 represent the same meaning as described above. ]

  Examples of the group represented by the formula (D-3) include groups represented by the following formulas (D-3-1) to (D-3-8).

R ^p represents the same meaning as described above.

  Since at least one of D in the formula (1) is more excellent in luminous efficiency of the light-emitting element obtained by using the composition of the present invention, the group represented by the formula (D-2) or the formula (D -3) is preferable, and at least two of D are more preferably a group represented by the formula (D-2) or a group represented by the formula (D-3). Preferably, at least two of D are groups represented by the formula (D-2).

  Examples of the compound represented by the formula (1) include compounds represented by the following formulas (1-1) to (1-27), preferably the following formulas (1-1) to (1-25). The compound represented by formula (1-1) to (1-19) is more preferred because the luminous efficiency using the composition of the present invention is more excellent. Compounds represented by formulas (1-1) to (1-13), particularly preferred are compounds represented by formulas (1-1) to (1-6), and particularly preferred are formulas (1- It is a compound represented by 1).

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

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

  As a compound represented by Formula (1), the compound represented by the following is mentioned, for example.

  The manufacturing method of the compound represented by Formula (1) is demonstrated.

  The compound represented by the formula (1) may be produced by any method. For example, the compound represented by the formula (S-1) and the compound represented by the formula (S-2) (m) And a coupling reaction such as Suzuki reaction, Kumada reaction, Stille reaction. More specifically, the compound represented by the formula (S-1) and the compound (m-2) represented by the formula (S-2) are dissolved in an organic solvent, and then an alkali, a catalyst is used as necessary. Can be synthesized by reacting at a temperature not lower than the melting point of the organic solvent and not higher than the boiling point.

［式中、
ｍ、Ａｒ^１およびＤは、前記と同じ意味を表す。
Ｗ^１およびＷ^２は、それぞれ独立に、下記式（Ｗ−１）〜（Ｗ−１０）のいずれかで表される基、アルキルスルホニルオキシ基、シクロアルキルスルホニル基、アリールスルホニルオキシ基、塩素原子、臭素原子またはヨウ素原子を表し、これらの基は置換基を有していてもよい。複数存在するＷ^１およびＷ^２は、それぞれ同一でも異なっていてもよい。］

[Where:
m, Ar ¹ and D represent the same meaning as described above.
W ¹ and W ² are each independently a group represented by any of the following formulas (W-1) to (W-10), an alkylsulfonyloxy group, a cycloalkylsulfonyl group, an arylsulfonyloxy group, a chlorine atom Represents a bromine atom or an iodine atom, and these groups optionally have a substituent. A plurality of W ¹ and W ² may be the same or different. ]

  As a catalyst used for the coupling reaction, a palladium catalyst is preferable. Examples of the palladium catalyst include palladium acetate, bis (triphenylphosphine) palladium (II) dichloride, tetrakis (triphenylphosphine) palladium (0), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium ( II), tris (dibenzylideneacetone) dipalladium (0).

  The palladium catalyst may be used in combination with a phosphorus compound such as triphenylphosphine, tri (o-tolyl) phosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, 1,1′-bis (diphenylphosphino) ferrocene. .

Examples of the alkylsulfonyloxy group represented by W ¹ and W ² include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group.
Examples of the arylsulfonyloxy group represented by W ¹ and W ² include a p-toluenesulfonyloxy group.

The W ^1, since the coupling reaction with the formula (S-1) a compound represented by the formula (S-2) is represented by compounds (m pieces) easily progresses, the formula (W-1) ~ A group represented by any one of (W-10), a trifluoromethanesulfonyloxy group, a bromine atom or an iodine atom is preferred, and a group represented by a bromine atom is more preferred.

As W ² , since the coupling reaction of the compound represented by the formula (S-1) and the compound (m-2) represented by the formula (S-2) easily proceeds, the formula (W-1) A group represented by any one of (W-10), a trifluoromethanesulfonyloxy group, a bromine atom or an iodine atom is preferred, and a group represented by the formula (W-7) is more preferred.

<Phosphorescent compound>
Subsequently, at least one selected from the group consisting of a group represented by the formula (D-1), a group represented by the formula (D-2), and a group represented by the following formula (D-3) A phosphorescent compound having the above group will be described.

  Examples and preferred embodiments of the group represented by the formula (D-1), the group represented by the formula (D-2), and the group represented by the following formula (D-3) included in the phosphorescent compound are as follows: A group represented by the formula (D-1), a group represented by the formula (D-2), and a group represented by the following formula (D-3), which the compound represented by the formula (1) has Examples and preferred forms are the same.

  Examples of the phosphorescent compound include a ruthenium complex, a rhodium complex, a palladium complex, an iridium complex, and a platinum complex, preferably an iridium complex or a platinum complex, and more preferably an iridium complex.

  As the iridium complex, iridium complexes represented by the formulas Ir-1 to Ir-5 are preferable, and iridium complexes represented by the formulas Ir-1 to Ir-4 are more preferable.

［式中、
ｎ_D1は、１、２または３を表し、ｎ_D2は、１または２を表す。
Ｒ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7、Ｒ^D8、Ｒ^D11、Ｒ^D12、Ｒ^D13、Ｒ^D14、Ｒ^D15、Ｒ^D16、Ｒ^D17、Ｒ^D18、Ｒ^D19、Ｒ^D20、Ｒ^D21、Ｒ^D22、Ｒ^D23、Ｒ^D24、Ｒ^D25、Ｒ^D26、Ｒ^D31、Ｒ^D32、Ｒ^D33、Ｒ^D34、Ｒ^D35、Ｒ^D36およびＲ^D37は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基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^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7、Ｒ^D8、Ｒ^D11、Ｒ^D12、Ｒ^D13、Ｒ^D14、Ｒ^D15、Ｒ^D16、Ｒ^D17、Ｒ^D18、Ｒ^D19、Ｒ^D20、Ｒ^D21、Ｒ^D22、Ｒ^D23、Ｒ^D24、Ｒ^D25、Ｒ^D26、Ｒ^D31、Ｒ^D32、Ｒ^D33、Ｒ^D34、Ｒ^D35、Ｒ^D36およびＲ^D37が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
−Ａ^D1---Ａ^D2−は、アニオン性の２座配位子を表し、Ａ^D1およびＡ^D2は、それぞれ独立に、アニオン性の２座配位子を構成する炭素原子、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^D1---Ａ^D2−が複数存在する場合、それらは同一でも異なっていてもよい。
また、式Ｉｒ−１におけるＲ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7およびＲ^D8の少なくとも１つは、前記式（Ｄ−１）で表される基、前記式（Ｄ−２）で表される基、または、前記式（Ｄ−３）で表される基である。
また、式Ｉｒ−２におけるＲ^D11、Ｒ^D12、Ｒ^D13、Ｒ^D14、Ｒ^D15、Ｒ^D16、Ｒ^D17、Ｒ^D18、Ｒ^D19およびＲ^D20の少なくとも１つは、前記式（Ｄ−１）で表される基、前記式（Ｄ−２）で表される基、または、前記式（Ｄ−３）で表される基である。
また、式Ｉｒ−３におけるＲ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7、Ｒ^D8、Ｒ^D11、Ｒ^D12、Ｒ^D13、Ｒ^D14、Ｒ^D15、Ｒ^D16、Ｒ^D17、Ｒ^D18、Ｒ^D19およびＲ^D20の少なくとも１つは、前記式（Ｄ−１）で表される基、前記式（Ｄ−２）で表される基、または、前記式（Ｄ−３）で表される基である。
また、式Ｉｒ−４におけるＲ^D21、Ｒ^D22、Ｒ^D23、Ｒ^D24、Ｒ^D25およびＲ^D26の少なくとも１つは、前記式（Ｄ−１）で表される基、前記式（Ｄ−２）で表される基、または、前記式（Ｄ−３）で表される基である。
また、式Ｉｒ−５におけるＲ^D31、Ｒ^D32、Ｒ^D33、Ｒ^D34、Ｒ^D35、Ｒ^D36およびＲ^D37の少なくとも１つは、前記式（Ｄ−１）で表される基、前記式（Ｄ−２）で表される基、または、前記式（Ｄ−３）で表される基である。］

[Where:
n _D1 represents 1, 2 or 3, and n _D2 represents 1 or 2.
R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 are each independently a hydrogen atom Represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups optionally have a substituent. R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 Each may be the same or different.
-A ^D1 --- A ^D2 -represents an anionic bidentate ligand, and A ^D1 and A ^D2 each independently represent a carbon atom, oxygen atom or Represents a nitrogen atom, and these atoms may be atoms constituting a ring. When a plurality of -A ^D1 --- A ^D2 -are present, they may be the same or different.
In addition, at least one of R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 and R ^{D8 in} the formula Ir-1 is a group represented by the formula (D-1), The group represented by the formula (D-2) or the group represented by the formula (D-3).
In addition, at least one of R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19, and R ^D20 in formula Ir-2 is represented by formula (D-1). A group represented by the formula (D-2), or a group represented by the formula (D-3).
Further, R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R in Formula Ir-3 ^At least one of ^D17 , R ^D18 , R ^D19 and R ^D20 is a group represented by the formula (D-1), a group represented by the formula (D-2), or the formula (D-3). ).
In addition, at least one of R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25, and R ^D26 in Formula Ir-4 is a group represented by Formula (D-1) or Formula (D-2) Or a group represented by the formula (D-3).
In addition, at least one of R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36, and R ^D37 in Formula Ir-5 is a group represented by Formula (D-1), Formula (D -2) or a group represented by the formula (D-3). ]

  Since the iridium complexes represented by the formulas Ir-1 to Ir-5 are easy to synthesize, they are represented by the group represented by the formula (D-1) or the formula (D-2). It preferably has a group, and more preferably has a group represented by the formula (D-1).

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

［式中、＊は、Ｉｒと結合する部位を表す。］

[In formula, * represents the site | part couple | bonded with Ir. ]

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

［式中、
Dは、式(D-1)、式（D-2）または式（D-3）で表される基を表す。複数存在するDは、同一でも異なっていてもよい。
R^DCは、水素原子、アルキル基、シクロアルキル基、アリール基または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^DCは、同一でも異なっていてもよい。
R^DDは、アルキル基、シクロアルキル基、アリール基または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^DDは、同一でも異なっていてもよい。
ｎ_D2は、１または２を表す。］

[Where:
D represents a group represented by the formula (D-1), the formula (D-2) or the formula (D-3). A plurality of D may be the same or different.
R ^DC represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^DCs may be the same or different.
R ^DD represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of R ^DDs may be the same or different.
n _D2 represents 1 or 2. ]

  An iridium complex represented by the formula Ir-11 to Ir-13, an iridium complex represented by the formula Ir-21, an iridium complex represented by the formula Ir-31 to Ir-33, and a formula Ir-41 to Ir-43 In the iridium complex represented by the formulas Ir-51 to Ir-53, a plurality of Ds are preferably the same because of the ease of synthesis of the iridium complex.

  As an iridium complex, the metal complex represented by the following is mentioned, for example.

  Examples of the phosphorescent compound include JP-T-2004-530254, JP-A-2008-179617, JP-A-2011-105701, JP-T-2007-504272, JP-A-2013-147449, and JP-A-2013-147449. It can be synthesized according to the method described in 2013-147450 and US Patent Application Publication No. 2011/0057559.

<Composition ratio, etc.>
Lowest excited triplet energy level (T ₁₎ is possessed by the compound represented by the formula (1), relative to the lowest excited triplet energy level possessed by the phosphorescent compound (T _1), the equivalent energy level Or it is preferable that it is a high energy level.

  Since the luminous efficiency of the light-emitting element obtained using the composition of the present invention is more excellent, the compound represented by the formula (1) and the phosphorescent compound are represented by the group represented by the formula (D-1): It preferably has at least one identical group selected from the group consisting of a group represented by D-2) and a group represented by formula (D-3), and is represented by formula (D-1). It is more preferable to have at least one identical group selected from the group consisting of a group represented by formula (D-2) and a group represented by formula (D-2).

Here, having the same group means that m ^{D1 to} m ^D4 , G, Ar ^{D1 to} Ar ^D4 and T constituting the formulas (D-1), (D-2) and (D-3) are respectively It means having the group which is the same.

  The content of the phosphorescent compound contained in the composition of the present invention is usually 1 to 400 parts by weight, preferably 3 to 200 parts by weight with respect to 100 parts by weight of the compound represented by the formula (1). More preferably, it is 3-100 weight part, More preferably, it is 5-70 weight part.

<Other ingredients>
The composition of the present invention includes a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (different from the phosphorescent compound which is an essential component of the composition of the present invention), and antioxidant. It may further contain at least one material selected from the group consisting of an agent and a solvent.

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

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

  The solvent contained in the ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples of the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, 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 amount of the solvent is usually 1000 to 100,000 parts by weight with respect to 100 parts by weight of the total of the compound represented by the formula (1) and the phosphorescent compound which are essential components of the composition of the present invention. And preferably 2000 to 20000 parts by weight.

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

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

  The compounding amount of the hole transport material is usually 1 to 400 parts by weight based on 100 parts by weight of the total of the compound represented by the formula (1) and the phosphorescent compound which are essential components of the composition of the present invention. And preferably 5 to 150 parts by weight.

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

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

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

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

  The compounding amount of the electron transport material is usually 1 to 400 parts by weight with respect to 100 parts by weight as a total of the compound represented by the formula (1) and the phosphorescent compound which are essential components of the composition of the present invention. Yes, preferably 5 to 150 parts by weight.

  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; polymers containing aromatic amine residues in the main chain or side chain, etc. Examples thereof include conductive polymers.

  The compounding amounts of the hole injecting material and the electron injecting material are usually based on a total of 100 parts by weight of the compound represented by the formula (1) and the phosphorescent compound, which are essential components of the composition of the present invention. 1 to 400 parts by weight, preferably 5 to 150 parts by weight.

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

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

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

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

[Light emitting material]
Luminescent materials (different from phosphorescent compounds that are essential components of the composition of the present invention) are classified into low molecular compounds and high molecular compounds. The light emitting material may have a crosslinking group.

  Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.

  Examples of the polymer compound include phenylene group, naphthalenediyl group, anthracenediyl group, fluorenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, aromatic amine residue, carbazole diyl group, phenoxazine diyl group, phenothiazine diyl. And a polymer compound containing a group, a pyrenediyl group, and the like.

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

  The content of the light emitting material is usually 0.1 to 400 parts by weight with respect to 100 parts by weight of the total of the compound represented by the formula (1) and the phosphorescent compound which are essential components of the composition of the present invention. .

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the compound represented by formula (1) and the phosphorescent compound that are essential components of the composition of the present invention and does not inhibit light emission and charge transport. Examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

  The blending amount of the antioxidant is usually 0.001 to 10 parts by weight with respect to 100 parts by weight of the total of the compound represented by the formula (1) and the phosphorescent compound which are essential components of the composition of the present invention. is there.

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

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

  The film includes an insolubilized film in which components contained in the composition of the present invention are insolubilized in a solvent by crosslinking. The insolubilized film is a film obtained by crosslinking the components contained in the composition of the present invention by external stimulation such as heating and light irradiation. Since the insolubilized film is substantially insoluble in a solvent, the insolubilized film can be suitably used for stacking light emitting elements.

  The heating temperature for crosslinking the film is usually 25 to 300 ° C., and the light emission efficiency becomes good. Therefore, the heating temperature is preferably 50 to 250 ° C., more preferably 150 to 200 ° C.

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

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

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

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

<Light emitting element>
The light-emitting device of the present invention is a light-emitting device obtained by using the composition of the present invention, and the component contained in the composition of the present invention may be cross-linked or contained in the composition of the present invention. The compound represented by the formula (1) and / or the phosphorescent compound may be crosslinked within a molecule or between molecules, or may be crosslinked within a molecule or between molecules. Good.
As a structure of the light emitting element of this invention, it has an electrode which consists of an anode and a cathode, and a layer obtained using the composition of this invention provided between this electrode, for example.

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

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

  As the material for the hole transport layer, electron transport layer, light emitting layer, hole injection layer and electron injection layer, in addition to the composition of the present invention, the above-described hole transport material, electron transport material, light emitting material, positive A hole injection material and an electron injection material are mentioned.

  When the light-emitting element of the present invention has an electron transport layer, the electron transport material used for forming the electron transport layer is represented by the structural unit represented by the formula (ET-1) and the formula (ET-2). A polymer compound containing at least one structural unit selected from the group consisting of structural units is preferred.

［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 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 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.

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

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

  The order, number, and thickness of the layers to be stacked may be adjusted in consideration of light emission efficiency and element lifetime.

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

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

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

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

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

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

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

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

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

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

<Synthesis Example 1> Synthesis of Compound G1 Compound G1 was synthesized according to the method described in JP2009-131255A.

<Synthesis Example 2> Synthesis of Compound G2

  Compound G2a (20.00 g, 74.79 mmol) and iridium chloride trihydrate (11.93 g, 33.83 mmol) synthesized according to the method described in JP-A-2005-99481 were added to the reaction vessel, and the reaction was performed. The gas in the container was replaced with argon gas. Thereafter, 2-ethoxyethanol (180 mL) and water (60 mL) were added thereto, and the inside of the reaction vessel was placed in an argon gas stream, followed by refluxing at 101 to 102 ° C. for 20 hours. After cooling, the resulting mixture was filtered off. The obtained residue was washed with water (400 mL), methanol (200 mL) and hexane (200 mL) in this order, and then dried to obtain compound G2b (22.49 g).

  Compound G2b (22.49 g, 14.79 mmol) and compound G2a (19.77 g, 73.95 mmol) were added to the reaction vessel, and the gas in the reaction vessel was replaced with argon gas. Thereafter, diglyme (128 mL) and silver trifluoromethanesulfonate (7.60 g, 29.58 mmol) were added thereto, and the inside of the reaction vessel was placed under an argon gas stream, followed by stirring at 148 to 150 ° C. for 5 hours. Thereafter, silver trifluoromethanesulfonate (7.60 g, 29.58 mmol) was added thereto, and the mixture was further stirred for 12 hours. After allowing to cool, water (600 mL) was added to the resulting reaction mixture, and the resulting precipitate was filtered off. The resulting precipitate was dissolved in toluene (500 mL) and then filtered. The filtrate obtained was dried over magnesium sulfate, filtered and concentrated to remove the solvent. The obtained residue was dissolved in a mixed solvent consisting of hexane and toluene (hexane / toluene = 3/1 (volume basis)) and purified by silica gel column chromatography, and then the solvent was distilled off. The obtained residue was washed with methanol (200 mL) and then dried. The obtained solid was crystallized using a mixed solvent consisting of toluene and acetonitrile (toluene / acetonitrile = 1.0 / 4.8 (volume basis)), and the obtained crystals were separated by filtration. The obtained solid was washed with methanol and dried to obtain compound G2 (14.30 g).

¹ H NMR (300 MHz, CDCl ₃ ); δ (ppm) = 0.88 (m, 9H), 1.22 (m, 30H), 1.44 (m, 6H), 2.35 (t, J = 7.5 Hz, 6H), 6.69 (m, 6H), 6.78 (t, J = 6.0 Hz, 3H), 7.47 (m, 9H), 7.77 (d, J = 6. 0 Hz, 3H).
LC-MS (APCI, positive) m / z: 992 ([M + H] ⁺ )

<Synthesis Example 3> Synthesis of Compound G3 Compound G3 was synthesized according to the method described in JP-A-2006-188673.

<Synthesis Example 4> Synthesis of Compound G4 Compound G4 was synthesized according to the method described in International Publication No. 2002/44189 pamphlet.

<Synthesis Example 5> Synthesis of Compound G5

(Synthesis of Compound G5-S2)

<Stage1>
After the atmosphere in the reaction vessel was set to an argon gas atmosphere, Compound G5-S2a (250 g), 4-dimethylaminopyridine (178 g) and dichloromethane (3.1 L) were added, and the mixture was cooled in an ice bath. Thereafter, trifluoromethanesulfonic anhydride (376 g) was added dropwise thereto over 1 hour, stirred for 1.5 hours, and then warmed to room temperature. Thereafter, hexane (3.1 L) was added, and the mixture was stirred for 10 minutes, then passed through a silica gel short column, and the solvent was distilled off by concentration under reduced pressure to obtain Compound G5-S2b (441 g) as a white solid. .

<Stage2>
After the inside of the reaction vessel was filled with an argon gas atmosphere, compound G5-S2b (410 g), bis (pinacolato) diboron (338 g), palladium acetate (4.08 g), tri-cyclohexylphosphine (10.2 g), potassium acetate (238 g) ) And dioxane (2.6 L) were added, and the mixture was stirred for 15 hours with heating under reflux. The obtained reaction mixture was passed through a filter covered with celite, and then the obtained filtrate was concentrated to obtain a solid. The obtained solid was dissolved in a mixed solvent of hexane / dichloromethane = 1/1 (volume ratio), then passed through a filter coated with silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. . Methanol was added to the obtained solid and stirred well, then the precipitated solid was collected by filtration and dried under reduced pressure at 50 ° C. overnight to obtain compound G5-S2c (274 g) as a white solid. The HPLC area percentage value (detection wavelength UV254 nm) of compound G5-S2c was 98% or more. Further, the filtrate was concentrated under reduced pressure, methanol was added, and after stirring well, the precipitated solid was collected by filtration and dried under reduced pressure at 50 ° C. overnight to recover compound G5-S2c (45 g) ( Total yield 75%).

<Stage3>
After the inside of the reaction vessel was filled with an argon gas atmosphere, Compound G5-S1 (90 g), Compound G5-S2c (239 g), 20 wt% tetraethylammonium hydroxide aqueous solution (795 g), palladium acetate (0.34 g), tri- ( Orthomethoxyphenyl) phosphine (1.07 g) and toluene (1.7 L) were added, and the mixture was stirred at 95 ° C. for 5.5 hours. The obtained reaction mixture was separated to obtain an organic layer. The obtained organic layer was washed successively with ion-exchanged water and 5% by weight saline and passed through a filter covered with silica gel to remove the solid content. The obtained filtrate was concentrated under reduced pressure and then purified by silica gel column chromatography (hexane / dichloromethane) to obtain a fraction containing the desired product. The obtained fraction was concentrated under reduced pressure, and dried under reduced pressure at 50 ° C. overnight to obtain compound G5-S2d (167 g) as a white solid. The yield was 98%. The HPLC area percentage value (detection wavelength UV254 nm) of compound G5-S2d was 99.4%.

<Stage4>
After the inside of the reaction vessel was filled with an argon gas atmosphere, compound G5-S2d (175 g), bis (pinacolato) diboron (104 g), (1,5-cyclooctadiene) (methoxy) iridium (I) (dimer) (3. 72 g), 4,4′-di-tert-butyl-2,2′-bipyridyl (3.01 g) and cyclohexane (2.0 L) were added, and the mixture was stirred for 4 hours with heating under reflux. Silica gel was added to the resulting reaction mixture and stirred for 30 minutes. Then, the solid content was removed by passing through a filter with silica gel. The obtained filtrate was concentrated under reduced pressure, hexane was added, and the mixture was stirred at room temperature. The precipitated solid was collected by filtration, washed with acetonitrile, and dried at 50 ° C. overnight under reduced pressure to obtain the desired product. Compound G5-S2 (137 g) was obtained as a white solid. The yield was 61%. The HPLC area percentage value (detection wavelength UV254 nm) of compound G5-S2 was 99.3%. By repeating this operation, the required amount of Compound G5-S2 was obtained.

¹ H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.58 (s, 2H), 7.43 (d, 4H), 7.26 (d, 4H), 2.11 (s , 3H), 1.80 (s, 4H), 1.41 (s, 12H), 1.32 (s, 12H), 0.76 (s, 18H).

(Synthesis of Compound G5-S3)

<Stage1>
The reaction vessel was filled with an argon gas atmosphere, then compound G5-S1 (46.0 g), compound G5-S2 (230 g) synthesized in the same manner as described above, 20 wt% tetraethylammonium hydroxide aqueous solution (407 g), acetic acid Palladium (0.17 g), tri- (orthomethoxyphenyl) phosphine (0.55 g) and toluene (880 mL) were added, and the mixture was stirred at 95 ° C. for 5.5 hours. The obtained reaction mixture was separated to obtain an organic layer. The obtained organic layer was washed once with ion-exchanged water, washed once with 5 wt% saline, dried over anhydrous sodium sulfate, and the solid content was removed by filtration. The obtained filtrate was concentrated under reduced pressure, purified by silica gel column chromatography (hexane / chloroform), concentrated under reduced pressure, and dried under reduced pressure at 50 ° C. overnight to give compound G5-S3a (181 g) as a white solid. Got as. The yield was 94%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G5-S3a was 97.9%.

<Stage2>
After making the inside of the reaction vessel an argon gas atmosphere, compound G5-S3a (171 g), bis (pinacolato) diboron (46.5 g), (1,5-cyclooctadiene) (methoxy) iridium (I) (dimer) ( 3.31 g), 4,4′-di-tert-butyl-2,2′-bipyridyl (2.68 g) and cyclohexane (900 mL) were added, and the mixture was stirred for 16 hours under heating to reflux. Silica gel (192 g) was added to the obtained reaction mixture and stirred for 30 minutes, and then the solid content was removed by passing the solution through a filter covered with silica gel. The obtained filtrate was concentrated under reduced pressure, purified by recrystallization (hexane), and the obtained solid was washed with methanol and dried under reduced pressure at 50 ° C. overnight to obtain the target compound G5- S3 (95 g) was obtained as a white solid. The yield was 49%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G5-S3 was 98.7%.

¹ H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.65 (s, 2H), 7.44 (d, 8H), 7.32 (d, 8H), 7.22 (s) , 4H), 2.35 (s, 3H), 2.14 (s, 6H), 1.79 (s, 8H), 1.41 (s, 24H), 1.29 (s, 12H), 0 74 (s, 36H).

(Synthesis of Compound G5)

  Compound G5a was synthesized according to the method described in JP-A-2011-105701, and one having an HPLC area percentage value (detection wavelength UV254 nm) of 99.5% or more was used.

<Stage1>
After the light-shielded reaction vessel was filled with an argon gas atmosphere, compound G5a (4.56 g), compound G5-S3 (8.35 g), tetrahydrofuran (240 mL), tetrakis (triphenylphosphine) palladium (0) (0.332 g) ) And 20 wt% tetraethylammonium hydroxide aqueous solution (17.7 g) were added, and the mixture was stirred for 16 hours under heating to reflux. The obtained reaction mixture was concentrated under reduced pressure, and toluene and ion-exchanged water were added for liquid separation to obtain an aqueous layer and an organic layer. Toluene was added to the obtained aqueous layer for extraction, added to the previously obtained organic layer, washed twice with 5% by weight brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain a solid. It was. The obtained solid was dissolved in toluene and passed through a filter covered with silica gel to obtain a filtrate. After the solvent of the obtained filtrate was distilled off by concentration under reduced pressure, the obtained solid was purified successively by silica gel column chromatography (hexane / toluene) and recrystallization (toluene / isopropanol), and then reduced pressure at 50 ° C. overnight. Drying gave Compound G5 (7.89 g) as a red solid. The yield was 86%. HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G5 was 98.5%.

LC / MS (APCI positive): m / z ⁺ = 3778 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 9.32 (s, 1H), 9.20-9.16 (m, 2H), 9.12 (d, 1H), 8 .96 (d, 1H), 8.62 (s, 1H), 8.41-8.25 (m, 10H), 8.15 (d, 2H), 7.95-7.90 (m, 2H) ), 7.77 (s, 2H), 7.70-7.59 (m, 12H), 7.52 (d, 2H), 7.46-7.18 (m, 56H), 2.33 ( s, 6H), 2.15 (s, 12H), 1.76 (s, 16H), 1.45-1.24 (m, 102H), 0.72 (s, 72H).

<Synthesis Example 6> Synthesis of Compound G6

(Synthesis of Compound S1)

<Stage1>
After the inside of the reaction vessel was under a nitrogen gas stream, 4-tert-octylphenol (250.00 g, 1.21 mol, Aldrich product), N, N-dimethyl-4-aminopyridine (177.64 g, 1.45 mol) and Dichloromethane (3100 mL) was added and this was ice-cooled to 5 ° C. Thereafter, trifluoromethanesulfonic anhydride (376.06 g, 1.33 mol) was added dropwise thereto over 45 minutes. After completion of the dropwise addition, the mixture was stirred for 30 minutes under ice cooling, then returned to room temperature and further stirred for 1.5 hours. Hexane (3100 mL) was added to the obtained reaction mixture, this reaction mixture was filtered using 410 g of silica gel, and further mixed with a mixed solvent (2.5 L) of hexane / dichloromethane (1/1 (volume basis)). The silica gel was washed. The obtained filtrate and washings were concentrated to obtain colorless oil compound S1-a (410.94 g, 1.21 mol, HPLC area percentage value 99.7%).

<Stage2>
After the inside of the reaction vessel was under a nitrogen gas stream, compound S1-a (410.94 g, 1.21 mol), bis (pinacolato) diboron (338.47 g, 1.33 mol), potassium acetate (237.83 g, 2. 42 mol), 1,4-dioxane (2600 mL), palladium acetate (4.08 g, 0.018 mol) and tricyclohexylphosphine (10.19 g, 0.036 mol) were added and refluxed for 2 hours. After cooling to room temperature, the resulting reaction mixture was filtered to collect the filtrate, the filtrate was further washed with 1,4-dioxane (2.5 L), and the resulting filtrate and washing were concentrated. The obtained residue was dissolved in a mixed solvent of hexane / dichloromethane (1/1 (volume basis)), filtered using 770 g of silica gel, and further mixed with hexane / dichloromethane (1/1 (volume basis)). The silica gel was washed with a solvent (2.5 L). The obtained filtrate and washing solution were concentrated, methanol (1500 mL) was added to the obtained residue, and ultrasonic washing was performed for 30 minutes. Thereafter, this was filtered to obtain Compound S1-b (274.27 g). The filtrate and the washing solution were concentrated, methanol was added, ultrasonic washing was performed, and filtration was repeated to obtain Compound S1-b (14.29 g). The total yield of the obtained compound S1-b was 288.56 g.

<Stage3>
After the inside of the reaction vessel was under a nitrogen gas stream, 1,3-dibromobenzene (102.48 g, 0.434 mol), compound S1-b (288.56 g, 0.912 mol), toluene (2100 mL), 20% by weight Tetraethylammonium hydroxide aqueous solution (962.38 g, 1.31 mol) and bis (triphenylphosphine) palladium (II) dichloride (3.04 g, 0.004 mol) were added and refluxed for 7 hours. After cooling to room temperature, the aqueous layer and the organic layer were separated, and the organic layer was collected. Toluene (1 L) was added to this aqueous layer, and the organic layer was further extracted. The obtained organic layers were combined and washed with a mixed aqueous solution of distilled water / saturated saline (1.5 L / 1.5 L). The obtained organic layer was filtered through 400 g of silica gel, and the silica gel was washed with toluene (2 L). The resulting solution was concentrated and the resulting residue was dissolved in hexane. This was purified by silica gel column chromatography. Impurities were eluted with hexane as a developing solvent, and then developed with a mixed solvent of hexane / dichloromethane (10/1 (volume basis)). The obtained fractions were concentrated under reduced pressure to remove the solvent, and colorless crystals of compound S1-c (154.08 g, HPLC area percentage value 99.1%) and crude compound S1-c (38.64 g, HPLC An area percentage value of 83%) was obtained. This crude compound S1-c was purified again under the same development conditions, and the solvent was distilled off under reduced pressure to obtain compound S1-c (28.4 g, HPLC area percentage value 99.6%). The total yield of the obtained compound S1-c was 182.48 g (0.40 mol).

<Stage4>
After the inside of the reaction vessel was placed in a nitrogen gas stream, compound S1-c (182.48 g, 0.401 mol), bis (pinacolato) diboron (112.09 g, 0.441 mol), 4,4′-di-tert- Butyl-2,2′-dipyridyl (3.23 g, 0.012 mol), cyclohexane (2000 mL) and bis (1,5-cyclooctadiene) di-μ-methoxydiiridium (I) (3.99 g, 0.002 g). 006 mol) and refluxed for 2 hours. After air cooling to room temperature, silica gel (220 g) was added over 20 minutes while stirring the resulting reaction mixture. The obtained suspension was filtered through 440 g of silica gel, the silica gel was further washed with dichloromethane (2 L), and the solution was concentrated. Methanol (1100 mL) and dichloromethane (110 mL) were added to the obtained residue, and the mixture was refluxed for 1 hour. After cooling to room temperature, it was filtered. The obtained filtrate was washed with methanol (500 mL), and the obtained solid was dried to obtain compound S1 (220.85 g, 0.380 mol).

¹ H-NMR (CDCl ₃ , 300 MHz): δ (ppm) = 8.00 (s, 2H), 7.92 (s, 1H), 7.60 (d, J = 8.5 Hz, 4H), 7 .44 (d, J = 8.5 Hz, 4H), 1.78 (s, 4H), 1.41 (s, 12H), 1.37 (s, 12H), 0.75 (s, 18H).

(Synthesis of Compound S2)

<Stage1>
After the inside of the reaction vessel was under a nitrogen gas stream, Compound S1 (91.49 g, 158 mmol), m-dibromobenzene (17.70 g, 75 mmol) and toluene (478 mL) were added, and nitrogen gas was bubbled for 20 minutes. Thereafter, 20% by weight tetraethylammonium hydroxide aqueous solution (166 mL, 225 mmol) and bis (triphenylphosphine) palladium (II) dichloride (0.26 g, 0.37 mmol) were added thereto, and the mixture was refluxed for 6.5 hours. After cooling to room temperature, the organic layer was separated from the obtained reaction solution, and this organic layer was washed with water (300 mL) and saturated brine (300 mL) in this order. The obtained organic layer was dried over sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was dissolved in a mixed solvent of hexane / chloroform ((20/1 (volume basis)), purified by silica gel column chromatography, and the solvent was removed by concentration under reduced pressure. (845 mL) and chloroform (56 mL) were added, and the mixture was refluxed for 30 minutes.

<Stage2>
After making the inside of reaction container under nitrogen gas stream, compound S2-a (74.40 g, 76 mmol), bis (pinacolato) diboron (21.13 g, 83 mmol), 4,4′-di-tert-butyl-2, 2′-dipyridyl (609 mg, 2 mmol), cyclohexane (734 mL) and bis (1,5-cyclooctadiene) di-μ-methoxydiiridium (I) (752 mg, 1 mmol) were added and refluxed for 8 hours. After cooling to room temperature with air, silica gel (83.93 g) was added to the resulting reaction solution, and the mixture was purified by silica gel column chromatography (developing solvent: mixed solvent of dichloromethane / acetonitrile (100/1 (volume basis))). The word, the solvent was distilled off under reduced pressure, and the resulting residue was dissolved in toluene (420 mL) and heated to 50 ° C. Thereafter, acetonitrile (839 mL) was added dropwise thereto, and the precipitated solid was filtered. The obtained solid was refluxed in a mixed solvent of hexane / acetonitrile (1/1 (volume basis)) for 30 minutes, cooled to room temperature, and the precipitate was collected by filtration and dried to give compound S2 (68. 53 g) was obtained.

¹ H-NMR (CDCl ₃ , 300 MHz): δ (ppm) = 8.14 (d, J = 1.8 Hz, 2H), 8.09 (m, 1H), 7.85 (d, J = 1. 6 Hz, 4H), 7.82 (m, 2H), 7.64 (d, J = 8.5 Hz, 8H), 7.48 (d, J = 8.5 Hz, 8H), 1.79 (s, 8H), 1.42 (s, 24H), 1.39 (s, 12H), 0.77 (s, 36H).

(Synthesis of Compound G6)

  After the light-shielded reaction vessel was filled with an argon gas atmosphere, Compound G5a (1.34 g), Compound S2 (2.34 g), tetrahydrofuran (60 mL), tetrakis (triphenylphosphine) palladium (0) (98 mg) and 20 wt. % Tetraethylammonium hydroxide aqueous solution (5.2 g) was added, and the mixture was stirred for 18 hours with heating under reflux. Toluene and ion-exchanged water were added to the obtained reaction mixture for liquid separation to obtain an aqueous layer and an organic layer. The obtained aqueous layer was extracted with toluene, added to the previously obtained organic layer, washed successively with ion-exchanged water and 5% by weight saline, and dried over anhydrous sodium sulfate. Then, the solid content was removed by passing through a filter with silica gel. After the solvent was distilled off from the obtained filtrate by concentration under reduced pressure, the obtained solid was purified by silica gel column chromatography (hexane / toluene) to obtain a fraction containing the desired product. The obtained fraction was concentrated under reduced pressure, recrystallized using a mixed solvent of toluene and isopropanol, and then dried under reduced pressure at 50 ° C. overnight to obtain the target compound G6 (2.43 g) as a red solid. Got as. The yield was 73%. The obtained compound G6 had an HPLC area percentage value (detection wavelength UV254 nm) of 99.8%.

LC-MS (APCI positive): m / z = 3694.2 [M + H] ⁺
1H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 9.39 (s, 1H), 9.27-9.21 (m, 2H), 9.17 (d, 1H), 9. 04 (d, 1H), 8.68 (s, 1H), 8.47 (d, 1H), 8.39-8.29 (m, 11H), 8.29 (s, 6H), 8.05 -7.80 (m, 16H), 7.73-7.42 (m, 56H), 7.33 (s, 2H), 1.77 (s, 16H), 1.39-1.21 (m , 102H), 0.74 (s, 72H).

<Synthesis Example 7> Synthesis of Compound G7

(Synthesis of Compound G7b)

  After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, compound G7a (38 g) synthesized according to the method described in JP-A-2008-179617, N-bromosuccinimide (12.1 g) and chloroform (1800 mL) were added, Stir at room temperature for 24 hours. The obtained reaction mixture was passed through a filter covered with silica gel to remove solids. The obtained filtrate was concentrated under reduced pressure to remove the solvent to obtain a solid. The obtained solid was purified by silica gel column chromatography (chloroform / hexane = 1/3) to obtain a fraction containing the desired product. The obtained fraction was concentrated, purified by performing recrystallization (dichloromethane / hexane) three times, and dried under reduced pressure at 50 ° C. overnight to obtain compound G7b (22.1 g) as a red solid. . The yield was 51%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G7b was 99.4%.

LC / MS (APCI-posi): m / z = 1920 [M + H] ^+
1 H-NMR (300 MHz / CD ₂ Cl ₂ ): δ (ppm =) 9.31 (d, 3H), 9.26 (dd, 3H), 8.38 (d, 12H), 8.22 (d , 3H), 7.96 (d, 3H), 7.43 (d, 12H), 7.00 (dd, 3H), 6.82 (d, 3H), 1.23 (s, 18H).

(Synthesis of Compound G7)

<Stage1>
After the inside of the reaction vessel was filled with an argon gas atmosphere, bis (4-tert-butylphenyl) amine (98.5 g), tris (dibenzylideneacetone) dipalladium (0) (3.21 g), tri-tert-butylphosphine Tetrafluoroborate salt (4.06 g), sodium-tert-butoxide (67.3 g) and toluene (665 mL) were added and heated to 80 ° C. with stirring. Thereafter, bromobenzene (57.1 g) dissolved in toluene (55 ml) was added dropwise thereto, and the mixture was stirred at 85 ° C. for 4 hours. The resulting reaction mixture was diluted with toluene (680 ml) and then filtered while hot to remove the solid. Activated clay (35 g) and activated alumina (35 g) were added to the obtained filtrate, and the mixture was stirred at 90 ° C. for 1.5 hours, and then the solid was removed by filtration while hot. The solvent was removed by concentrating the obtained filtrate under reduced pressure to obtain a solid. The obtained solid was purified by recrystallization (hexane / ethanol) twice and dried under reduced pressure at 50 ° C. overnight to obtain the target compound G7-S1 (99 g) as a solid. . The yield was 79%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G7-S1 was 99.9% or more.

<Stage2>
After the light-shielded reaction vessel was filled with an argon gas atmosphere, Compound G7-S1 (71.5 g), N-iodosuccinimide (49.5 g) and N, N-dimethylformamide (800 mL) were added and stirred at 30 ° C. Heated to. Then, trifluoroacetic acid (11.4g) was dripped there, and it stirred at 50 degreeC for 4 hours. Then, it cooled using the ice bath and solid was obtained when ion-exchange water (800 mL) and 10-% sodium chloride aqueous solution (200 mL) were dripped. The obtained solid was dissolved in toluene (1 L) and then washed twice with ion-exchanged water (800 mL) to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to distill off the solvent to obtain a solid. The obtained solid was dried at 50 ° C. under reduced pressure overnight, purified by recrystallization (chloroform / methanol), and dried at 50 ° C. under reduced pressure overnight to obtain the target compound G7-S2. (84 g) was obtained as a solid. The yield was 87%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G7-S2 was 99.4%.

<Stage3>
After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, Compound G7-S2 (7.5 g) and tetrahydrofuran (80 mL) were added. Thereafter, isopropylmagnesium chloride (2 mol / L, 15 mL) dissolved in tetrahydrofuran was added dropwise thereto, and the mixture was stirred at room temperature for 1 hour. Thereafter, the mixture was cooled using an ice bath, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.4 mL) was added, and the mixture was stirred for 5 minutes. Thereafter, the ice bath was removed, and the mixture was stirred for 3 hours while slowly warming to room temperature. Then, after cooling again using an ice bath, extraction was performed using a mixed solvent of ethyl acetate (90 mL) and toluene (30 mL), and the obtained organic layer was washed twice with 15 wt% brine (50 mL). To obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to distill off the solvent to obtain a solid. The obtained solid was purified by recrystallization (chloroform / methanol) twice and dried under reduced pressure at 50 ° C. overnight to obtain the target compound G7-S3 (5.5 g) as a white solid. Got as. The yield was 74%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G7-S3 was 99.5% or more.

TLC / MS (DART positive): m / z = 484 [M + H] ⁺

<Stage4>
After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, compound G7b (5.0 g), compound G7-S3 (4.4 g), tetrakis (triphenylphosphine) palladium (0) (360 mg), 20% by weight tetraethylammonium Aqueous hydroxide (20 mL) and tetrahydrofuran (210 ml) were added, and the mixture was stirred for 24 hours under reflux with heating. Then, it cooled to room temperature, toluene (400 mL) and ion-exchange water (400 mL) were added and extracted, and the organic layer was obtained. The obtained organic layer was washed twice with ion-exchanged water and once with 5 wt% saline to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to distill off the solvent to obtain a solid. The obtained solid was purified by recrystallization (toluene / isopropanol) and dried under reduced pressure at 50 ° C. overnight to obtain Compound G7 (3.9 g) as a red solid. The yield was 55%. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound G7 was 99.5% or more.

¹ H-NMR (300 MHz / CD ₂ Cl ₂ ): δ (ppm) = 9.41 (d, 3H), 9.21 (dd, 3H), 8.39 (d, 12H), 8.26 (d 3H), 7.96 (s, 3H), 7.45 to 7.38 (m, 18H), 7.27 (dd, 12H), 7.23 to 7.16 (m, 6H), 6. 96 (d, 18H), 1.30 (s, 54H), 1.22 (s, 54H).
LC / MS (APCI positive): m / z = 2755 [M + H] ⁺

<Synthesis Example 8> Synthesis of Compound G8

<Stage1>
After making the inside of the reaction vessel an argon gas atmosphere, Compound G8a (9.9 g), Compound S1 (15 g), 2-dicyclohexylphosphino-2 ′, synthesized according to US Patent Application Publication No. 2011/0057559, 6'-dimethoxybiphenyl (0.11 g), tris (dibenzylideneacetone) dipalladium (0.12 g), 20 wt% tetraethylammonium aqueous solution (20 mL), toluene (200 mL) and ethanol (50 mL) were added and heated to reflux. Stirring under for 18 hours. Then, it cooled to room temperature and added toluene and extracted. The obtained organic layer was washed with ion-exchanged water, and then concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel chromatography (ethyl acetate / hexane), recrystallized using a mixed solvent of toluene and acetonitrile, and then dried under reduced pressure to give compound G8b (17 g, yield 90%). Got.

<Stage2>
After the inside of the reaction vessel was filled with an argon gas atmosphere, Compound G8b (10 g), iridium chloride hydrate (2.2 g), 2-ethoxyethanol (120 mL) and water (40 mL) were added, and the mixture was stirred with heating under reflux for 14 hours. did. Then, when it cooled to room temperature and methanol was added, precipitation occurred. The obtained precipitate was filtered, and the obtained solid was washed with methanol and dried under reduced pressure to obtain Intermediate G8 (10 g, yellow powder).

  The reaction vessel was filled with an argon gas atmosphere, intermediate G8 (9.5 g), silver trifluoromethanesulfonate (31 g), dichloromethane (100 mL) and methanol (30 mL) were added, and the mixture was stirred overnight at room temperature. After the deposited precipitate was filtered, the obtained filtrate was concentrated under reduced pressure. Thereafter, compound G8b (7.8 g), 2,6-lutidine (6.7 mL) and diethylene glycol dimethyl ether (180 mL) were added thereto, and the mixture was stirred overnight with heating under reflux. Then, it cooled to room temperature, the mixed solvent of ion-exchange water and methanol was added, and the depositing deposit was filtered. The obtained solid was purified by silica gel chromatography (dichloromethane / hexane), recrystallized using a mixed solvent of toluene and acetonitrile, and then dried under reduced pressure to give compound G8 (1.2 g, yield 6. 5%).

¹ H-NMR (600 MHz, (CD ₃ ) ₂ CO-d ₆ ) δ (ppm) = 8.01-7.97 (m, 9H), 7.91 (d, 6H), 7.81 (d, 12H), 7.59 (d, 12H), 7.25 (s, 3H), 6.92-6.89 (m, 6H), 6.57 (t, 3H), 5.87-5.81 (M, 6H), 2.89-2.86 (m, 3H), 2.52-2.48 (m, 3H), 1.87 (s, 12H), 1.42 (s, 36H), 1.38 (d, 9H), 1.16 (d, 9H), 1.12 (d, 9H), 1.07 (d, 9H), 0.80 (54H).

<Synthesis Example 9> Synthesis of Compound H1

<Step 1>
After making the inside of the reaction vessel a nitrogen gas atmosphere, Compound 1 (336 g, 370 mmol), bis (pinacolato) diboron (113 g, 445 mmol), palladium (II) acetate (1.88 g, 8.37 mmol), tricyclohexylphosphine (4 .68 g, 16.7 mmol), potassium acetate (72.7 g, 741 mmol) and 1,4-dioxane (1580 mL) were added, and the mixture was stirred for 26 hours under heating to reflux. Then, after cooling to room temperature, after adding and diluting 1, 4- dioxane (1000 mL), the solid was removed by filtration. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (n-hexane / dichloromethane = 1/1), and further purified by performing recrystallization (dichloromethane / acetonitrile) twice. The obtained solid was dried under reduced pressure at 50 ° C. overnight to obtain the target compound 2 (276 g) as a white solid. The yield was 84%. The obtained compound 2 had an HPLC area percentage value (detection wavelength UV254 nm) of 99.3%.
Compound 1 was synthesized by the method described in JP 2010-31259 A.

TLC / MS (DART positive): m / z ⁺ = 886 [M + H] ^+
1 H-NMR (300 MHz / CD ₂ Cl ₂ ): δ (ppm) = 8.14 (brs, 3H), 7.88 (d, 4H), 7.84-7.82 (m, 2H), 7 .69 (d, 8H), 7.53 (d, 8H), 1.38 (brs, 48H).

<Step 2>
After the inside of the reaction vessel was filled with an argon gas atmosphere, compound 3 (4.26 g, 10 mmol), compound 2 (29.21 g, 33 mmol), toluene (100 mL), PdCl ₂ (PPh ₃ ) ₂ (35 mg, 0.05 mmol) And 20 weight% tetraethylammonium hydroxide aqueous solution (22g) was added, and it stirred under heating-refluxing for 3 hours. Then, after cooling to room temperature, toluene (600 mL) was added to dilute, then washed twice with ion-exchanged water (200 mL), further washed with 15 wt% saline (200 mL), and the organic layer was separated by liquid separation. Got. Thereafter, the obtained organic layer was dried by adding anhydrous sodium sulfate, the solid was removed by filtration, passed through a silica gel short column, and the resulting solution was concentrated under reduced pressure to obtain a solid. The obtained solid was purified using medium pressure silica gel chromatography (hexane / chloroform), and further purified by recrystallization (hexane / ethanol) three times. The obtained solid was dried under reduced pressure at 50 ° C. overnight to obtain the target compound, Compound H1 (10.9 g) as a white solid. The HPLC area percentage value (detection wavelength UV254 nm) of the obtained compound H1 was 99.5% or more. The yield was 44%.
Compound 3 was synthesized by the method described in JP 2010-189630 A.

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 9.09 (s, 2H), 8.94 (d, 4H), 8.18 (s, 1H), 7.82 (m, 28H) ), 7.67 (m, 24H), 7.50 (d, 24H), 1.38 (s, 72H), 1.34 (s, 36H).

<Synthesis Example 10> Synthesis of Compound H2, Compound H3, and Compound H4

Compound H2 was synthesized according to the method described in JP 2010-189630 A.
Compound H3 was purchased from Luminesense Technology.

<Synthesis Example 11> Synthesis of Polymer Compound P1

Monomer CM1 was synthesized according to the synthesis method described in JP 2010-189630 A.
Monomer CM2 was synthesized according to the synthesis method described in WO2005 / 049546.
Monomer CM3 was synthesized according to the synthesis method described in WO2011 / 049241.

After the inside of the reaction vessel was placed in a nitrogen gas atmosphere, monomer CM1 (3.39 mmol), monomer CM2 (2.96 mmol), monomer CM3 (0.52 mmol) and toluene (73 ml) were added, and about Heated to 80 ° C. Thereafter, palladium acetate (0.77 mg), tris (2-methoxyphenyl) phosphine (4.90 mg) and a 20 wt% tetraethylammonium hydroxide aqueous solution (12.3 g) were added thereto, and the mixture was stirred for about 4 hours under reflux. did. Thereafter, phenylboronic acid (85.6 mg), palladium acetate (0.72 mg), tris (2-methoxyphenyl) phosphine (4.89 mg) and a 20 wt% tetraethylammonium hydroxide aqueous solution (12.3 g) were added thereto. In addition, the mixture was further stirred for about 19.5 hours under reflux. Thereafter, a solution obtained by dissolving sodium N, N-diethyldithiocarbamate trihydrate (0.98 g) in ion-exchanged water (20 ml) was added thereto, and the mixture was stirred for 2 hours while heating to 85 ° C. Thereafter, the organic layer was washed successively with 3.6 wt% hydrochloric acid twice, 2.5 wt% aqueous ammonia solution twice, and ion-exchanged water five times. The obtained organic layer was dropped into methanol to cause precipitation, and the solid was obtained by filtration and drying. The obtained solid was dissolved in toluene, and passed through a silica gel column and an alumina column through which toluene was passed in advance. The obtained solution was added dropwise to methanol to cause precipitation, and the polymer compound P1 (2.907 g) was obtained by filtering and drying. The number average molecular weight (Mn) and weight average molecular weight (Mw) in terms of polystyrene of the polymer compound 1 were Mn = 1.9 × 10 ⁴ and Mw = 9.9 × 10 ⁴ .

  The polymer compound P1 is derived from the structural unit derived from the monomer CM1, the structural unit derived from the monomer CM2, and the structural unit derived from the monomer CM3 in the theoretical value obtained from the charged amount of the monomer. Is a copolymer having a molar ratio of 50: 42.5: 7.5.

<Synthesis Example 12> Synthesis of polymer compound P2

Monomer CM1 was synthesized according to the synthesis method described in JP 2010-189630 A.
Monomer CM4 was synthesized according to the synthesis method described in JP-A-2008-106241.
Monomer CM5 was synthesized according to the synthesis method described in JP 2010-215886 A.
Monomer CM6 was synthesized according to the synthesis method described in International Publication No. 2002/045184.

(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound CM1 (0.995 g), Compound CM4 (0.106 g), Compound CM5 (0.0924 g), Compound CM6 (0.736 g), dichlorobis [ Tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) and toluene (50 ml) were added and heated to 105 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (6.6 ml) was added dropwise to the resulting reaction solution and refluxed for 5.5 hours.
(Step 3) Thereafter, phenylboronic acid (24.4 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (6.6 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) were added thereto. The mixture was 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. The obtained reaction solution was cooled, then 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 obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred. The obtained precipitate was collected by filtration and dried to obtain 0.91 g of polymer compound P2. The Mn of the polymer compound P2 was 5.2 × 10 ⁴ and the Mw was 2.5 × 10 ⁵ .

  The theoretical value obtained from the amount of the raw material used for the polymer compound P2 is that the structural unit derived from the compound CM1, the structural unit derived from the compound CM4, the structural unit derived from the compound CM5, and the compound CM6 The derived structural unit is a copolymer having a molar ratio of 50: 5: 5: 40.

<Synthesis Example 13> Synthesis of polymer compound ET1

Compound ET1-1 was synthesized according to the synthesis method described in JP 2012-33845 A.
Compound ET1-2 was synthesized according to the synthesis method described in JP 2012-33845 A.

(Synthesis of polymer compound ET1a)
The polymer compound ET1a was synthesized according to the synthesis method described in JP 2012-33845 A using the compound ET1-1 and the compound ET1-2.

The Mn of the polymer compound ET1a was 5.2 × 10 ⁴ .

  The polymer compound ET1a is composed of a structural unit derived from the compound ET1-1 and a structural unit derived from the compound ET1-2 in a molar ratio of 50:50 according to the theoretical value obtained from the amount of the raw materials. It is a copolymer obtained.

(Synthesis of polymer compound ET1)
After making the inside of reaction container into inert gas atmosphere, the high molecular compound ET1a (200 mg), tetrahydrofuran (20 mL), and ethanol (20 mL) were added, and it heated at 55 degreeC. Cesium hydroxide (200 mg) dissolved in water (2 mL) was added thereto, and the mixture was stirred at 55 ° C. for 6 hours. Then, after cooling to room temperature, solid was obtained by concentrating under reduced pressure. The obtained solid was washed with water and then dried under reduced pressure to obtain a polymer compound ET1 (150 mg, light yellow solid). From the NMR spectrum of the resulting polymer compound ET1, it was confirmed that the signal derived from the ethyl group at the ethyl ester site of the polymer compound ET1a had completely disappeared.

<Example 1> Production and evaluation of light-emitting element 1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 65 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 0.6% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Compound H1 and compound G1 (compound H1 / compound G1 = 70 wt% / 30 wt%) were dissolved in xylene at a concentration of 3.5 wt%. Using the obtained xylene solution, a film having a thickness of 80 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 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 1 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 1. The driving voltage at 1000 cd / m ² was 6.0 [V], the luminous efficiency was 61.5 [cd / A], and the emission spectrum peak wavelength was 520 [nm]. The results are shown in Table 3.

Comparative Example 1 Production and Evaluation of Light-Emitting Element C1 A light-emitting element C1 was produced in the same manner as in Example 1 except that Compound H2 was used instead of Compound H1 in Example 1.

EL light emission was observed by applying a voltage to the light emitting element C1. The driving voltage at 1000 cd / m ² was 5.4 [V], the light emission efficiency was 22.4 [cd / A], and the emission spectrum peak wavelength was 520 [nm]. The results are shown in Table 3.

Comparative Example 2 Production and Evaluation of Light-Emitting Element C2 A light-emitting element C2 was produced in the same manner as in Example 1 except that CBP was used instead of the compound H1 in Example 1.

EL light emission was observed by applying a voltage to the light emitting element C2. The driving voltage at 1000 cd / m ² was 5.5 [V], the light emission efficiency was 24.0 [cd / A], and the emission spectrum peak wavelength was 520 [nm]. The results are shown in Table 3.

Comparative Example 3 Production and Evaluation of Light-Emitting Element C3 A light-emitting element C3 was produced in the same manner as in Example 1 except that Compound G2 was used instead of Compound G1 in Example 1.

EL light emission was observed by applying a voltage to the light emitting element C3. The driving voltage at 1000 cd / m ² was 5.0 [V], the luminous efficiency was 50.2 [cd / A], and the emission spectrum peak wavelength was 520 [nm]. The results are shown in Table 3.

Comparative Example 4 Production and Evaluation of Light-Emitting Element C4 In place of Compound H1 and Compound G1 (Compound H1 / Compound G1 = 70 wt% / 30 wt%) in Example 1, Compound H2 and Compound G2 (Compound H2 / A light emitting device C4 was produced in the same manner as in Example 1 except that Compound G2 = 70 wt% / 30 wt%) was used.

EL light emission was observed by applying a voltage to the light emitting element C4. The driving voltage at 1000 cd / m ² was 5.1 [V], the light emission efficiency was 11.9 [cd / A], and the emission spectrum peak wavelength was 520 [nm]. The results are shown in Table 3.

Comparative Example 5 Production and Evaluation of Light-Emitting Element C5 Instead of Compound H1 and Compound G1 (Compound H1 / Compound G1 = 70 wt% / 30 wt%) in Example 1, CBP and Compound G2 (CBP / Compound G2) = 70 wt% / 30 wt%) was used in the same manner as in Example 1 to fabricate a light emitting device C5.

EL light emission was observed by applying a voltage to the light emitting element C5. The driving voltage at 1000 cd / m ² was 9.7 [V], the light emission efficiency was 0.4 [cd / A], and the emission spectrum peak wavelength was 520 [nm]. The results are shown in Table 3.

Example 2 Production and Evaluation of Light-Emitting Element 2 Instead of Compound H1 and Compound G1 (Compound H1 / Compound G1 = 70 wt% / 30 wt%) in Example 1, Compound H1 and Compound G3 (Compound H1 / A light emitting device 2 was produced in the same manner as in Example 1 except that the compound G3 = 90 wt% / 10 wt%) was used.

EL light emission was observed by applying a voltage to the light emitting element 2. The driving voltage at 1000 cd / m ² was 10.3 [V], the luminous efficiency was 5.4 [cd / A], and the emission spectrum peak wavelength was 625 [nm]. The results are shown in Table 4.

Example 3 Production and Evaluation of Light-Emitting Element 3 A light-emitting element 3 was produced in the same manner as in Example 2 except that Compound G5 was used instead of Compound G3 in Example 2.

When a voltage was applied to the light emitting element 3, EL light emission was observed. The driving voltage at 1000 cd / m ² was 7.3 [V], the luminous efficiency was 13.2 [cd / A], and the emission spectrum peak wavelength was 615 [nm]. The results are shown in Table 4.

Example 4 Production and Evaluation of Light-Emitting Element 4 Light-emitting element 4 was produced in the same manner as in Example 2 except that compound G6 was used instead of compound G3 in Example 2.

EL light emission was observed by applying a voltage to the light emitting element 4. The driving voltage at 1000 cd / m ² was 7.9 [V], the luminous efficiency was 13.6 [cd / A], and the emission spectrum peak wavelength was 610 [nm]. The results are shown in Table 4.

Example 5 Production and Evaluation of Light-Emitting Element 5 A light-emitting element 5 was produced in the same manner as in Example 2 except that Compound G7 was used instead of Compound G3 in Example 2.

EL light emission was observed by applying a voltage to the light emitting element 5. The driving voltage at 1000 cd / m ² was 7.1 [V], the light emission efficiency was 13.8 [cd / A], and the emission spectrum peak wavelength was 620 [nm]. The results are shown in Table 4.

Comparative Example 6 Production and Evaluation of Light-Emitting Element C6 A light-emitting element C6 was produced in the same manner as in Example 2, except that Compound G4 was used instead of Compound G3 in Example 2.

EL light emission was observed by applying a voltage to the light emitting element C6. The driving voltage at 1000 cd / m ² was 9.6 [V], the luminous efficiency was 1.8 [cd / A], and the emission spectrum peak wavelength was 625 [nm]. The results are shown in Table 4.

<Example 6> Production and evaluation of light-emitting element 6 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
The polymer compound P2 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)
Compound H3 and compound G8 (compound H3 / compound G8 = 75 wt% / 25 wt%) were dissolved in chlorobenzene at a concentration of 2.5 wt%. Using the obtained chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound ET1 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)
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 6 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element 6. The driving voltage at 1000 cd / m ² was 10.2 [V], the luminous efficiency was 19.1 [cd / A], and the emission spectrum peak wavelength was 480,505 [nm]. The results are shown in Table 5.

Claims (11)

A compound represented by the following formula (1);
At least one selected from the group consisting of a group represented by the following formula (D-1), a group represented by the following formula (D-2), and a group represented by the following formula (D-3). And a phosphorescent compound having a group.

[Where:
m represents an integer of 2 or more.
Ar ¹ represents a heterocyclic group, and this group may have a substituent.
D represents a group represented by the following formula (D-1), a group represented by the following formula (D-2), or a group represented by the following formula (D-3). A plurality of D may be the same or different. ]

[Where:
m ^D1 , m ^D2 , m ^D3 and m ^D4 each independently represent an integer of 0 or more. A plurality of m ^D2 , m ^D3 and m ^D4 may be the same or different.
G represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. When a plurality of G are present, they may be the same or different.
Ar ^D1 , Ar ^D2 , Ar ^D3 and Ar ^D4 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 ^D1 , Ar ^D2 , Ar ^D3 and Ar ^D4 , they may be the same or different.
T represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of T may be the same or different. ]   The composition according to claim 1, wherein at least one of D is a group represented by the formula (D-2) or a group represented by the formula (D-3). The composition according to claim 1 or 2, wherein Ar ¹ is a nitrogen-containing heterocyclic group. The composition according to claim 3, wherein Ar ¹ is a heterocyclic group formed by removing two or more hydrogen atoms directly bonded to carbon atoms constituting the ring of 1,3,5-triazine. G represents a group represented by the following formula (GDA-11), a group represented by the following formula (GDA-12), a group represented by the following formula (GDA-13), and the following formula (GDA-14) The composition as described in any one of Claims 1-4 which is group represented by these, or group represented by a following formula (GDA-15).

[Where:
* ^Represents the bond between Ar ^D1 in the formula (D-1), Ar ^D1 or Ar ^D2 in the formula (D-2), or Ar ^D1 , Ar ^D2 or Ar ^D3 in the formula (D-3). Represent.
** represents a bond with Ar ^D2 in the formula (D-1), Ar ^D2 or Ar ^D3 in the formula (D-2), or Ar ^D2 , Ar ^D3 or Ar ^D4 in the formula (D-3). Represents.
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 a plurality of ^RDA are present, they may be the same or different. ]   The composition according to claim 5, wherein G is a group represented by the formula (GDA-11). The phosphorescent compound is an iridium complex represented by the following formula Ir-1, an iridium complex represented by the following formula Ir-2, an iridium complex represented by the following formula Ir-3, or a formula represented by the following formula Ir-4. The composition as described in any one of Claims 1-6 which is an iridium complex represented by the following formula Ir-5.

[Where:
n _D1 represents 1, 2 or 3, and n _D2 represents 1 or 2.
R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 are each independently a hydrogen atom Represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups optionally have a substituent. R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19 , R ^D20 , R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25 , R ^D26 , R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36 and R ^D37 Each may be the same or different.
-A ^D1 --- A ^D2 -represents an anionic bidentate ligand, and A ^D1 and A ^D2 each independently represent a carbon atom, oxygen atom or Represents a nitrogen atom, and these atoms may be atoms constituting a ring. When a plurality of -A ^D1 --- A ^D2 -are present, they may be the same or different.
In addition, at least one of R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 and R ^{D8 in} the formula Ir-1 is a group represented by the formula (D-1), The group represented by the formula (D-2) or the group represented by the formula (D-3).
In addition, at least one of R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R ^D17 , R ^D18 , R ^D19, and R ^D20 in formula Ir-2 is represented by formula (D-1). A group represented by the formula (D-2), or a group represented by the formula (D-3).
Further, R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 , R ^D8 , R ^D11 , R ^D12 , R ^D13 , R ^D14 , R ^D15 , R ^D16 , R in Formula Ir-3 ^At least one of ^D17 , R ^D18 , R ^D19 and R ^D20 is a group represented by the formula (D-1), a group represented by the formula (D-2), or the formula (D-3). ).
In addition, at least one of R ^D21 , R ^D22 , R ^D23 , R ^D24 , R ^D25, and R ^D26 in Formula Ir-4 is a group represented by Formula (D-1) or Formula (D-2) Or a group represented by the formula (D-3).
In addition, at least one of R ^D31 , R ^D32 , R ^D33 , R ^D34 , R ^D35 , R ^D36, and R ^D37 in Formula Ir-5 is a group represented by Formula (D-1), Formula (D -2) or a group represented by the formula (D-3). ] The compound represented by the formula (1) and the phosphorescent compound are:
At least one selected from the group consisting of a group represented by the formula (D-1), a group represented by the formula (D-2), and a group represented by the formula (D-3). The composition according to any one of claims 1 to 7, which has the same group.   The composition according to any one of claims 1 to 8, wherein a content of the phosphorescent compound is 5 to 70 parts by weight with respect to 100 parts by weight of the compound represented by the formula (1). .   The hole transport material, the hole injection material, the electron transport material, the electron injection material, the light emitting material, at least one material selected from the group consisting of an antioxidant and a solvent is further contained. The composition according to one item.   The light emitting element obtained using the composition as described in any one of Claims 1-10.