JP6519108B2 - Composition and light emitting device using the same - Google Patents

Description

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

  A light emitting element using a high molecular compound can be increased in area by a coating method such as an inkjet printing method, and can be driven at a low voltage, so that application to a large display, illumination, Application to the field is expected (see Patent Documents 1 and 2).

  In Patent Document 3, a polymer metal complex that emits blue light, a polymer metal complex that emits green light, and a polymer metal complex that emits red light (any polymer metal complex is a polymer metal complex having a transition metal complex) There is described a white light emitting device using a composition containing Moreover, in Patent Document 4, a white light emitting device using a composition containing two or more types of polymer compounds that exhibit fluorescence (these polymer compounds are polymer compounds having different luminescent colors) Is described.

Japanese Patent Application Laid-Open No. 8-209120 Japanese Patent Application Publication No. 2003-155476 JP 2001-185357 A International Publication No. 2000/46321

  However, a light emitting element using the above composition does not necessarily have sufficient luminance life.

  Then, this invention aims at providing the composition which can be adjusted for luminescent color and is useful for manufacture of the light emitting element which is excellent in the brightness | luminance lifetime. Another object of the present invention is to provide a light emitting device comprising the composition and an illumination comprising the light emitting device.

First of all, the present invention
A polymer compound that exhibits blue fluorescence;
A polymer compound that exhibits green fluorescence,
A metal complex exhibiting red phosphorescence and / or having at least one group selected from the group consisting of a group represented by the following formula (Dend-A) and a group represented by the following formula (Dend-B) Composition having a structure of a metal complex that exhibits red phosphorescence emission having at least one group selected from the group consisting of a group represented by the following formula (Dend-A) and a group represented by the following formula (Dend-B) Provided is a composition containing a polymer compound containing a unit.

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

[In the formula (Dend-A),
G ^DA1 represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 exist, they may be the same or different.
T ^DA2 and T ^DA3 each independently represent an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more. ]

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

[In the formula (Dend-B),
G ^DA1 , G ^DA2 and G ^DA3 each independently represent a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent Good. When a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are present, they may be the same or different.
T ^DA4 , T ^DA5 , T ^DA6 and T ^DA7 each independently represent an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more. ]

Second, the present invention
Furthermore, a composition comprising at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent is provided.

  The present invention thirdly provides a light emitting device comprising the above composition.

  The present invention provides, in a fourth aspect, an illumination including the light emitting element.

  ADVANTAGE OF THE INVENTION According to this invention, adjustment of luminescent color is possible and the composition useful for manufacture of the light emitting element which is excellent in the brightness | luminance lifetime can be provided. Further, according to the present invention, it is possible to provide a light emitting device containing the composition and illumination including the light emitting device.

It is the emission spectrum in 300 cd / m < ² > of the light emitting element D1. Emitting element D1 to D10, a CIE1931 chromaticity coordinates of the emission spectrum at 300 cd / ^{m 2} of BD1, GD1 and RD1.

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

  A polymer compound exhibiting blue fluorescence emission means a sample (film thickness of about 50 nm to 100 nm) formed by depositing a polymer compound alone on a quartz substrate or the like, and when this sample is photoexcited, the maximum peak of the fluorescence emission spectrum A polymer compound having a wavelength of 380 nm or more and less than 490 nm is meant. A polymer compound exhibiting green fluorescence emission means a sample (film thickness of about 50 nm to about 100 nm) formed by depositing a polymer compound alone on a quartz substrate or the like, and when this sample is photoexcited, the maximum peak of the fluorescence emission spectrum A polymer compound having a wavelength of 490 nm or more and less than 570 nm is meant. With a polymer compound containing a structural unit having a structure of a metal complex exhibiting red phosphorescence, a sample (film thickness of about 50 nm to 100 nm) in which a metal complex or a polymer compound is formed separately on a quartz substrate or the like is prepared When this sample is photoexcited, it means metal complexes and polymer compounds whose maximum peak wavelength in the phosphorescence emission spectrum is 570 nm or more and less than 700 nm.

  A metal complex exhibiting red phosphorescence is dissolved in an organic solvent such as toluene, xylene, chloroform or tetrahydrofuran (concentration: about 1 to 100 μM), and when this sample is photoexcited, the maximum peak wavelength of the phosphorescence spectrum is 570 nm or more By metal complex is meant less than 700 nm. As an organic solvent in which a metal complex exhibiting red phosphorescence is dissolved, xylene is preferable.

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

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 units contained in the polymer compound are 100 mol% in total.

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

  The "constituent unit" means a unit which is present one or more in the polymer compound.

The "alkyl group" may be linear, branched or cyclic. The carbon atom number of the linear alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent. The carbon atom number of the branched and cyclic alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent.
The alkyl group may have a substituent, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an tert-butyl group, an n-pentyl group and an isoamyl group. , 2-ethylbutyl group, n-hexyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, cyclohexylethyl group, n-octyl group, 2-ethylhexyl group, 3-n-propylheptyl group, n-decyl group, Unsubstituted alkyl groups such as 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyldecyl group, n-dodecyl group; trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluoro group Hexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3,5-di-n-hexylphenyl) propyl group, 6-ethyloxyhexyl group It includes substituted alkyl groups.

The “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 the aryl group is usually 6 to 60, preferably 6 to 20, more preferably 6 to 10, not including the carbon atom number of the substituent.
The aryl group may have a substituent, and examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 1-pyrenyl, 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 atom in these groups Are groups substituted with an alkyl group, an alkoxy group, an aryl group, a fluorine atom or the like.

The "alkoxy group" may be linear, branched or cyclic. The carbon atom number of the linear alkoxy group is usually 1 to 40, preferably 4 to 10, not including the carbon atom number of the substituent. The carbon atom number of the branched and cyclic alkoxy group is usually 3 to 40, preferably 4 to 10, not including the carbon atom number of the substituent.
The alkoxy group may have a substituent, and examples thereof include a methoxy group, an ethoxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, an isobutyloxy group, an tert-butyloxy group, and an n-pentyloxy group. Group, n-hexyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, 3, 7-dimethyloctyloxy group, lauryl An oxy group is mentioned.

The carbon atom number of the "aryloxy group" is usually 6 to 60, preferably 7 to 48, not including the carbon atom number of the substituent.
The aryloxy group may have a substituent, and examples thereof include phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- The pyrenyloxy group and the group by which the hydrogen atom in these groups was substituted by the alkyl group, the alkoxy group, the fluorine atom etc. are mentioned.

The “p-valent heterocyclic group” (p represents an integer of 1 or more) means p out of hydrogen atoms directly bonded to a carbon atom or a heteroatom constituting a ring from the heterocyclic compound. Means the remaining atomic groups excluding the hydrogen atom of Among the p-valent heterocyclic groups, carbon atoms constituting the ring or the remaining atomic groups obtained by removing p hydrogen atoms from hydrogen atoms directly bonded to a hetero atom from the aromatic heterocyclic compound "P-valent aromatic heterocyclic group" is preferred.
The “aromatic heterocyclic compound” is a complex such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole etc. Compounds in which the ring itself exhibits aromaticity, and heterocycles such as phenoxazine, phenothiazine, dibenzoborole, dibenzosilole, benzopyran and the like themselves have aromatic rings fused to the aromatic ring even if they do not exhibit aromaticity It means a compound.

The carbon atom number of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 14, not including the carbon atom number of the substituent.
The monovalent heterocyclic group may have a substituent, and examples thereof include thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and the like Groups in which a hydrogen atom in any of the groups is substituted with an alkyl group, an alkoxy group or the like.

  The "halogen atom" represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The "amino group" may have a substituent and is preferably a substituted amino group. As a substituent which an amino group has, an alkyl group, an aryl group or a monovalent heterocyclic group is preferable.
As a substituted amino group, a dialkylamino group and a diarylamino group are mentioned, for example.
Examples of the amino group include dimethylamino, diethylamino, diphenylamino, bis (4-methylphenyl) amino, bis (4-tert-butylphenyl) amino, and bis (3,5-di-tert-). And butylphenyl) amino.

The "arylene group" means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The carbon atom number of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 16, not including the carbon atom number of the substituent.
The arylene group may have a substituent, and examples thereof include phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrendiyl group, dihydrophenanthrendiyl group, naphthacene diyl group, fluorenediyl group, pyrene diyl group, perylene diyl group, There may be mentioned a chrysendiyl group and a group in which these groups have a substituent, and preferably a group represented by the formula (A-1) to the formula (A-20). 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、アルキル基またはアリール基を表す。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い。隣接する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 represent a hydrogen atom, an alkyl group or an aryl group. Plural R and R ^a may be the same or different. Adjacent R ^{a 's} may be bonded to each other to form a ring together with the atoms to which they are attached. ]

The carbon atom number of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15, not including the carbon atom number of the substituent.
The divalent heterocyclic group may have a substituent, and examples thereof include pyridine, diazabenzene, triazine, azanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan And thiophenes, azoles, diazoles, and triazoles, and divalent groups in which two hydrogen atoms of hydrogen atoms directly bonded to a carbon atom or hetero atom constituting a ring are removed, and preferably A-21) to a group represented by formula (A-52). 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 a heat treatment, an ultraviolet irradiation treatment, a radical reaction or the like, preferably a group represented by the formulas (B-1), (B-2) ), (B-3), (B-4), (B-5), (B-6), (B-7), (B-8), (B-9), (B-10), (B-11), (B-12), (B-13), (B-14), (B-15)
And (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。］

[Wherein, these groups may have a substituent. ]

  The “substituent” represents a halogen atom, a cyano group, an alkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, an aryloxy group, an amino group or a substituted amino group.

[Polymer compound exhibiting blue fluorescence emission, polymer compound exhibiting green fluorescence emission, and polymer compound including a structural unit having a structure of a metal complex exhibiting red phosphorescence emission]
As the polymer compound that exhibits blue fluorescence, a conjugated polymer compound that exhibits blue fluorescence is preferable. Further, as the polymer compound that exhibits blue fluorescence, a polymer compound that exhibits high fluorescence quantum yield at room temperature is preferable.
As the polymer compound that exhibits green fluorescence, a conjugated polymer compound that exhibits green fluorescence is preferable. Moreover, as a high molecular compound which shows green fluorescence, a high molecular compound which shows high fluorescence quantum yield at room temperature is preferable.
As the polymer compound containing a structural unit having a structure of a metal complex that exhibits red phosphorescence, a conjugated polymer compound containing a structural unit having a structure of a metal complex that exhibits red phosphorescence is preferable. Further, as the metal complex which exhibits red phosphorescence, a metal complex which exhibits high phosphorescence quantum yield at room temperature is preferable.

  The conjugated polymer compound is a polymer compound having a conjugated structure in the polymer main chain, as described in 2nd Edition Standard Chemical Dictionary (issued by Maruzen Co., Ltd.), and more specifically, a multiple bond The π electron, unpaired electron, and non-bonded electron pair are delocalized in the entire polymer main chain. As the conjugated polymer compound, for example, an arylene group, a divalent heterocyclic group, a divalent group in which at least one arylene group and at least one type of divalent heterocyclic group are directly bonded, and A polymer compound containing, as a constitutional unit, at least one group selected from the group consisting of aromatic aromatic amine residues as a constituent unit, and the total content of the constituent units is the total content of constituent units contained in the polymer compound The amount is usually 80% by mole or more, preferably 90% by mole or more, and more preferably 100% by mole. An arylene group, a divalent heterocyclic group, and a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other are represented by the formula (Y) described later Structural units are listed. As a bivalent aromatic amine residue, the structural unit represented by Formula (X) mentioned later is mentioned.

  The polymer compound that exhibits blue fluorescence and the polymer compound that exhibits green fluorescence contain the structural unit represented by formula (Y) because the luminance life of the light emitting device containing the composition of the present invention is more excellent. preferable.

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

[ ^Wherein , Ar ^{Y 1} represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one type of divalent heterocyclic group are directly bonded, Groups may have a substituent. ]

  A polymer compound containing a structural unit having a structure of a metal complex that exhibits red phosphorescence emits a structural unit represented by the above-mentioned formula (Y) because the luminance life of a light emitting device containing the composition of the present invention is more excellent. Is preferred.

The arylene group represented by Ar ^Y1 is more preferably a group represented by the formula (A-1), a formula (A-6), a formula (A-7), a formula (A-9), a formula (A-10) or a formula (A-13) or a group represented by formula (A-19), more preferably a group represented by formula (A-1), formula (A-7), formula (A-9) or formula (A-19) And these groups may have a substituent.

More preferably, the divalent heterocyclic group represented by Ar ^Y1 is represented by the formula (A-24), the formula (A-30), the formula (A-33), the formula (A-35), or the formula (A-). 38) or a group represented by formula (A-40), more preferably a group represented by formula (A-24), formula (A-30), formula (A-38) or formula (A-40) These groups may have a substituent.

More preferable range of an arylene group and a divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded, further preferable The ranges are respectively the same as the more preferable and further preferable ranges of the arylene group and the divalent heterocyclic group represented by Ar ^{Y 1} described above, but at least one arylene group and at least one kind of divalent As a divalent group to which a heterocyclic group is directly bonded, a divalent group in which one arylene group and one divalent heterocyclic group are directly bonded is preferable.

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

Examples of the structural unit represented by formula (Y) include structural units represented by formulas (Y-1) to (Y-7).
The polymer compound that exhibits blue fluorescence, the polymer compound that exhibits green fluorescence, and the polymer compound that includes a structural unit having a structure of a metal complex that exhibits red phosphorescence have a luminance lifetime of a light emitting device that includes the composition of the present invention Is more excellent, the structural unit represented by the formula (Y-1), the structural unit represented by the formula (Y-2), the structural unit represented by the formula (Y-5), the formula (Y-6) And at least one structural unit selected from the group consisting of a structural unit represented by formula (Y-7) and a structural unit represented by formula (Y-2) It is more preferable to include at least one structural unit selected from the group consisting of the structural units represented by formula (Y-5).

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

[Wherein, R ^Y1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Plural R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

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

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

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

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

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

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

In X ^Y1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group which may have a substituent. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which each is attached, and in the case where R ^Y2 forms a ring, -C (R ^Y2 ) ₂ -C (R ^Y2 ) _2- The group represented is preferably a group represented by formulas (Y-B1) to (Y-B5), more preferably a group represented by formula (Y-B3), and these groups are substituted It may have a group.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

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

［式中、
Ｒ^Y1は前記と同じ意味を表す。
Ｒ^Y3は、水素原子、アルキル基、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。］

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

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

［式中、
Ｒ^Y1は前記を同じ意味を表す。
Ｒ^Y4は、水素原子、アルキル基、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。］

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

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

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

  Since the luminance life of the light emitting device containing the composition of the present invention is more excellent, the composition of the present invention comprises a polymer compound exhibiting blue fluorescence, a polymer compound exhibiting green fluorescence and a metal complex exhibiting red phosphorescence. When it is contained, it is preferable that the polymer compound that exhibits blue fluorescence emission and the polymer compound that exhibits green fluorescence emission include a common structural unit represented by Formula (Y).

  Since the luminance life of the light emitting device containing the composition of the present invention is more excellent, the composition of the present invention is a polymer compound showing blue fluorescence, a polymer compound showing green fluorescence and a metal complex showing red phosphorescence. When including a polymer compound including a structural unit having a structure, a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a polymer compound that includes a component having a metal complex structure that exhibits red phosphorescence It is preferable that contains a common structural unit represented by Formula (Y).

  The polymer compound that exhibits blue fluorescence and the polymer compound that exhibits green fluorescence preferably have a structural unit represented by formula (X) because they are excellent in hole transportability, and are represented by formula (Y) It is more preferable to include the structural unit represented by the formula and the structural unit represented by the formula (X).

  A polymer compound containing a structural unit having a structure of a metal complex that exhibits red phosphorescence preferably has a structural unit represented by formula (X) since it has excellent hole transportability, and is preferably represented by formula (Y) It is more preferable to include the constituent unit represented by the formula and the constituent unit represented by formula (X).

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

[In the formula,
Each of a ^X1 and a ^X2 independently represents an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded These groups may have a substituent.
Each of R ^X1 , R ^X2 and R ^X3 independently represents a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

a ^X1 is preferably 2 or less, more preferably 1, because the luminance life of the light emitting device containing the composition of the present invention is more excellent.

a ^X2 is preferably 2 or less, more preferably 0, because the luminance life of the light emitting device containing the composition of the present invention is more excellent.

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

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

More preferably, the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 is represented by Formula (A-21) to Formula (A-26), Formula (A-28) to Formula (A-42) or Formula These groups are groups represented by (A-44) to formula (A-46), and these groups may have a substituent.

Ar ^X1 and Ar ^X3 are preferably an arylene group, more preferably a group represented by Formula (A-1) or Formula (A-9), and still more preferably a group of Formula (A-1) These groups may be substituted.

The arylene group represented by Ar ^X2 and Ar ^X4 is more preferably represented by Formula (A-1), Formula (A-6), Formula (A-7), Formula (A-9), or Formula (A-10) Or a group represented by formula (A-19), and these groups may have a substituent.

More preferable ^examples of the divalent heterocyclic group represented by Ar ^X2 and Ar ^X4 include Formula (A-21) to Formula (A-26) and Formula (A-28) to Formula (A-42). Or groups represented by formulas (A-44) to (A-46), and these groups may have a substituent.

More preferable range of arylene group and divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one divalent heterocyclic group are directly bonded Is at least one selected from Formula (A-1), Formula (A-6), Formula (A-7), Formula (A-9), Formula (A-10) and Formula (A-19) And at least one selected from an arylene group, a group represented by the formula (A-21) to the formula (A-26), a formula (A-28) to the formula (A-42) and a formula (A-44) to the formula (A-46) It is a divalent group to which a kind of divalent heterocyclic group is directly bonded, and these groups may have a substituent.
Examples of the divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one bivalent heterocyclic group are directly bonded to each other include, for example, groups represented by the following formulas: These may have a substituent.

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

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

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

Ar ^X2 and Ar ^X4 are preferably arylene groups, and more preferably formulas (A-1), (A-6), (A-7), (A-9), and (A). -10) or a group represented by formula (A-19), and these groups may have a substituent.

The substituent which the group represented by Ar ^{X1 to} Ar ^X4 and R ^{X1 to} R ^X3 may have is preferably an alkyl group or an aryl group, and these groups may further have a substituent Good.

  Examples of the structural unit represented by the formula (X) include structural units represented by the formulas (X-1) to (X-7).

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

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

  As a structural unit represented by Formula (X), the structural unit represented by Formula (X1-1)-(X1-17) is mentioned, for example, Preferably it is Formula (X1-6)-(X1-14) It is a structural unit represented by).

  The polymer compound that exhibits green fluorescence preferably includes the structural unit represented by the formula (G) because the luminance life of the light emitting device containing the composition of the present invention is more excellent.

［式中、Ａｒ^Ｇは、ベンゾチアジアゾールジイル基、キノキサリン構造を有する２価の基、少なくとも１つのチエニレン基と少なくとも１種のアリーレン基が直接結合した２価の基、少なくとも１種のアリーレン基と少なくとも１つのビニレン基が直接結合した２価の基、ペリレン構造を有する２価の基、または、下記式（Ｘ−８）で表される２価の基を表し、これらの基は置換基を有していてもよい。］

[Wherein, Ar ^G represents a benzothiadiazole diyl group, a divalent group having a quinoxaline structure, a divalent group in which at least one thienylene group and at least one arylene group are directly bonded, and at least one arylene group] Represents a divalent group to which at least one vinylene group is directly bonded, a divalent group having a perylene structure, or a divalent group represented by the following formula (X-8), these groups each having a substituent You may have. ]

［式中、Ｒ^ｘ４は前記と同じ意味を表す。］

[Wherein, R ^x4 represents the same meaning as described above. ]

  Examples of the divalent group having a quinoxaline structure include divalent groups represented by formulas (G-1) to (G-6).

［式中、Ｒは前記と同じ意味を表す。］

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

  Examples of the divalent group in which at least one thienylene group and at least one arylene group are directly bonded to one another include, for example, divalent groups represented by formulas (G-11) to (G-16).

［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. ]

  Examples of the divalent group in which at least one arylene group and at least one vinylene group are directly bonded include, for example, divalent groups represented by formulas (G-21) to (G-26).

［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. ]

  Examples of the divalent group having a perylene structure include divalent groups represented by formulas (G-41) to (G-42).

［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. ]

  [Structural unit having a structure of a metal complex exhibiting red phosphorescence emission and a metal complex exhibiting red phosphorescence emission]

  The metal complex exhibiting red phosphorescence contained in the composition of the present invention is at least one selected from the group consisting of a group represented by the formula (Dend-A) and a group represented by the formula (Dend-B) Have a group of

  In addition, the constituent unit having a structure of a metal complex which exhibits red phosphorescence and is contained in the composition of the present invention can be selected from the group represented by the formula (Dend-A) and the group represented by the formula (Dend-B) And at least one group selected from the group consisting of

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

[In the formula (Dend-A),
G ^DA1 represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. When a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 exist, they may be the same or different.
T ^DA2 and T ^DA3 each independently represent an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more. ]

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

[In the formula (Dend-B),
G ^DA1 , G ^DA2 and G ^DA3 each independently represent a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent Good. When a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are present, they may be the same or different.
T ^DA4 , T ^DA5 , T ^DA6 and T ^DA7 each independently represent an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more. ]

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

G ^DA1 is preferably a group represented by formulas (GDA-11) to (GDA-15), and these groups may have a substituent.

［式中、＊１、＊２および＊３は、各々、Ａｒ^DA1、Ａｒ^DA2およびＡｒ^DA3との結合を表す。Ｒ^DAは、水素原子、アルキル基、アルコキシ基、アリール基または１価の複素環基を表し、これらの基は更に置換基を有していてもよい。Ｒ^DAが複数ある場合、それらは同一でも異なっていてもよい。］

[Wherein, * 1, * 2 and * 3 each represent a bond to Ar ^DA1 , Ar ^DA2 and Ar ^DA3 . R ^DA represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of ^RDAs , they may be the same or different. ]

G ^DA2 is preferably a group represented by formulas (GDA-21) to (GDA-25), and these groups may have a substituent. G ^DA3 is preferably a group represented by formulas (GDA-31) to (GDA-35), and these groups may have a substituent.

［式中、＊２、＊４および＊５は、各々、Ａｒ^DA2、Ａｒ^DA4およびＡｒ^DA5との結合を表す。Ｒ^DAは、水素原子、アルキル基、アルコキシ基、アリール基または１価の複素環基を表し、これらの基は更に置換基を有していてもよい。Ｒ^DAが複数ある場合、それらは同一でも異なっていてもよい。］

[ ^Wherein , * 2, * 4 and * 5 each represents a bond to Ar ^DA2 , Ar ^DA4 and Ar ^DA5 . R ^DA represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of ^RDAs , they may be the same or different. ]

［式中、＊３、＊６および＊７は、各々、Ａｒ^DA3、Ａｒ^DA6およびＡｒ^DA7との結合を表す。Ｒ^DAは、水素原子、アルキル基、アルコキシ基、アリール基または１価の複素環基を表し、これらの基は更に置換基を有していてもよい。Ｒ^DAが複数ある場合、それらは同一でも異なっていてもよい。］

[ ^Wherein , * 3, * 6 and * 7 each represent a bond to Ar ^DA3 , Ar ^DA6 and Ar ^DA7 . R ^DA represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of ^RDAs , they may be the same or different. ]

R ^DA is preferably a hydrogen atom, an alkyl group or an alkoxy group, more preferably a hydrogen atom or an alkyl group, still more preferably a hydrogen atom, and these groups may have a substituent.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably groups represented by Formulas (ArDA-1) to (ArDA-3). When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.

［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、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。］

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

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

T ^DA2 , T ^DA3 , T ^DA4 , T ^DA5 , T ^DA6 and T ^DA7 are preferably groups 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 (Dend-A) is preferably a group represented by the formulas (Dend-A1) to (Dend-A3), and more preferably the formula (Dend-A2) or (Dend-A3) And more preferably a group represented by the formula (Dend-A3).

［式中、
Ｒ^p1、Ｒ^p2およびＲ^p3は、それぞれ独立に、アルキル基、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が複数個存在する場合、それらはそれぞれ同一でも異なっていてもよい。
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。複数存在するｎｐ１は、同一でも異なっていてもよい。］

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

  The group represented by the formula (Dend-B) is preferably a group represented by the formulas (Dend-B1) to (Dend-B3), and more preferably the formula (Dend-B2) or (Dend-B3) And more preferably a group represented by the formula (Dend-B3).

［式中、
Ｒ^p1、Ｒ^p2およびＲ^p3は、それぞれ独立に、アルキル基、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が複数個存在する場合、それらはそれぞれ同一でも異なっていてもよい。
ｎｐ１は０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０または１を表す。ｎｐ１およびｎｐ２が複数個存在する場合、それらはそれぞれ同一でも異なっていてもよい。］

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

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

R ^p1 , R ^p2 and R ^p3 are preferably alkyl groups.

  The structural unit represented by the formula (R) is preferable because a structural unit having a structure of a metal complex that exhibits red phosphorescence emission is more excellent in luminance life of a light emitting device including the composition of the present invention.

［式中、Ａｒ^Ｒは、前記式（Ｄｅｎｄ−Ａ）で表される基および前記式（Ｄｅｎｄ−Ｂ）で表される基からなる群から選ばれる少なくとも１種の基を有する赤色燐光発光を示す金属錯体の構造を有する２価の基を表す。］

[Wherein, in the formula, Ar ^R represents a red phosphorescence emission having at least one group selected from the group consisting of a group represented by the formula (Dend-A) and a group represented by the formula (Dend-B) It represents a divalent group having the structure of the metal complex shown. ]

Ar ^R is preferably a structural unit represented by formulas (Z-R1) to (Z-R14). In the structural units represented by the formulas (Z-R2) to (Z-R14), each of the ligands whose number is defined by the coefficient 2 is bonded to another structural unit.

［式中、
Ｒ^D1およびＲ^D2は、それぞれ独立に、水素原子、アルキル基、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。複数存在するＲ^D1は、同一でも異なっていてもよいが、少なくとも１つのＲ^D1は前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基である。複数存在するＲ^D2は、同一でも異なっていてもよいが、少なくとも１つのＲ^D2は前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基である。
Ｒ^D11は、水素原子、アルキル基、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。複数存在するＲ^D11は、同一でも異なっていてもよい。
Ｄｅｎｄは、前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基を表す。
Ｚ^Ｄは、窒素原子または＝Ｃ（−Ｒ^Ｄ２）−を表す。
−Ａ^D1---Ａ^D2−および−Ａ^D3---Ａ^D4−は、それぞれ独立に、アニオン性の２座配位子を表し、Ａ^D1、Ａ^D2、Ａ^D3およびＡ^D4は、それぞれ独立に、イリジウム原子と結合する炭素原子、酸素原子または窒素原子を表す。
ＭＣＸは、前記式（Ｄｅｎｄ−Ａ）で表される基および前記式（Ｄｅｎｄ−Ｂ）で表される基からなる群から選ばれる少なくとも１種の基を有する赤色燐光発光を示す金属錯体の構造を有する１価の基を表す。
Ａｒ^Ｒ１は、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。
ｎｐ４は、０または１を表す。］

[In the formula,
R ^D1 and R ^D2 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups have a substituent It is also good. Although a plurality of R ^D1 may be the same or different, at least one R ^D1 is a group represented by the above formula (Dend-A) or (Dend-B). Plural R ^D2 may be the same or different, but at least one R ^D2 is a group represented by the above formula (Dend-A) or (Dend-B).
R ^D11 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. Plural R ^D11 may be the same or different.
Dend represents a group represented by the formula (Dend-A) or (Dend-B).
Z ^D represents a nitrogen atom or = C (-R ^D2 )-.
-A ^D1 --- A ^D2 - and -A ^D3 --- A ^D4 - independently represent a bidentate ligand of the ^{anionic, A D1, A D2, A} D3 and A ^D4, respectively Independently, it represents a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom.
MCX is a structure of a metal complex exhibiting red phosphorescence emission having at least one group selected from the group consisting of a group represented by the formula (Dend-A) and a group represented by the formula (Dend-B) Represents a monovalent group having
Ar ^R1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
np4 represents 0 or 1. ]

R ^D11 is preferably a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.

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

［式中、Ｒ^D11およびＤｅｎｄは、前記と同じ意味を表す。Ｚ^Ｋは、窒素原子または＝Ｃ（−Ｒ^D11）−を表す。＊は、イリジウム原子との結合部位を表す。］

[Wherein, R ^D11 and Dend represent the same meaning as described above. Z ^K represents a nitrogen atom or = C (-R ^D11 )-. * Represents a binding site to an iridium atom. ]

Examples of the anionic bidentate ligand represented by -A ^D3 --- A ^D4- include a bidentate ligand represented below.

［式中、ＲおよびＲ^D11は、前記と同じ意味である。Ｚ^Ｌは、窒素原子または＝Ｃ（−Ｒ^D11）−を表す。Ｘは、酸素原子または硫黄原子を表す。＊は、イリジウム原子との結合部位を表す。］

[Wherein, R and R ^D11 have the same meaning as described above. Z ^L represents a nitrogen atom or = C (-R ^D11 )-. X represents an oxygen atom or a sulfur atom. * Represents a binding site to an iridium atom. ]

  MCX is preferably a monovalent group obtained by removing one hydrogen atom from the metal complex represented by the formulas (Z-R21) to (ZR-30).

［式中、
Ｒ^D3およびＲ^D4、は、それぞれ独立に、水素原子、アルキル基、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。複数存在するＲ^D3は、同一でも異なっていてもよいが、少なくとも１つのＲ^D3は前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基である。複数存在するＲ^D4は、同一でも異なっていてもよいが、少なくとも１つのＲ^D4は前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基である。
Ｒ^D1１は前記と同じ意味を表す。
Ｄｅｎｄは、前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基を表す。
Ｚ^Ｆは、窒素原子または＝Ｃ（Ｒ^Ｄ４）−を表す。
−Ａ^D5---Ａ^D6−および−Ａ^D7---Ａ^D8−は、それぞれ独立に、アニオン性の２座配位子を表し、Ａ^D5、Ａ^D6、Ａ^D7およびＡ^D8は、それぞれ独立に、イリジウム原子と結合する炭素原子、酸素原子または窒素原子を表す。
ｋｐは０、１または２を表し、ｋｑは０、１または２を表す。］

[In the formula,
R ^D3 and R ^D4 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups have a substituent May be Plural R ^D3 may be the same or different, but at least one R ^D3 is a group represented by the above formula (Dend-A) or (Dend-B). Plural R ^D4 may be the same or different, but at least one R ^D4 is a group represented by the above formula (Dend-A) or (Dend-B).
R ^D11 represents the same meaning as described above.
Dend represents a group represented by the formula (Dend-A) or (Dend-B).
Z ^F represents a nitrogen atom or = C (R ^D4 )-.
-A ^D5 --- A ^D6 - and -A ^D7 --- A ^D8 - independently represent a bidentate ligand of the ^{anionic, A D5, A D6, A} D7 and A ^D8, respectively Independently, it represents a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom.
kp represents 0, 1 or 2, and kq represents 0, 1 or 2. ]

-A ^D5 --- A ^D6 - The anionic bidentate ligand represented include bidentate ligands represented by the following.

［式中、Ｒ^D11は、前記と同じ意味を表す。Ｚ^Ｍは、窒素原子または＝Ｃ（−Ｒ^D11）−を表す。＊は、イリジウム原子との結合部位を表す。］

[Wherein, R ^D11 represents the same meaning as described above. Z ^M represents a nitrogen atom or = C (-R ^D11 )-. * Represents a binding site to an iridium atom. ]

Examples of the anionic bidentate ligand represented by -A ^D7 --- A ^D8- include the bidentate ligands represented below.

［式中、ＲおよびＲ^D11は、前記と同じ意味を表す。Ｚ^Ｎは、窒素原子または＝Ｃ（−Ｒ^D11）−を表す。＊は、イリジウム原子との結合部位を表す。Ｘは、酸素原子または硫黄原子を表す。］

[Wherein, R and R ^D11 represent the same meaning as described above. Z ^N represents a nitrogen atom or CC (—R ^D11 ) —. * Represents a binding site to an iridium atom. X represents an oxygen atom or a sulfur atom. ]

  The polymer compound containing a constituent unit having a structure of a metal complex exhibiting red phosphorescence contained in the composition of the present invention contains a constituent unit represented by the above formula (Z-R2) or (Z-R3). Are preferable, and it is more preferable to contain the structural unit represented by the following formula (Ir-4). In the structural unit represented by the formula (Ir-4), each of the ligands whose number is defined by the coefficient 2 is bonded to another structural unit.

［式中、Ｒ、ＤｅｎｄおよびＲ^D2は、前記と同じ意味を表す。］

[Wherein, R, Dend and R ^D2 represent the same meaning as described above. ]

  The structural unit having a structure of a metal complex exhibiting red phosphorescence is preferably a structural unit represented by the formula (R2) because the luminance life of the light emitting device containing the composition of the present invention is more excellent. The structural unit represented by the formula (R2) is a structural unit at the end of the terminal structural unit in a polymer compound including a structural unit having a structure of a metal complex that exhibits red phosphorescence.

［式中、Ａｒ^Ｒ２は、前記式（Ｄｅｎｄ−Ａ）で表される基および前記式（Ｄｅｎｄ−Ｂ）で表される基からなる群から選ばれる少なくとも１種の基を有する赤色燐光発光を示す金属錯体の構造を有する１価の基を表す。］

[Wherein, in the formula, Ar ^R2 represents a red phosphorescence emission having at least one group selected from the group consisting of a group represented by the formula (Dend-A) and a group represented by the formula (Dend-B) It represents a monovalent group having the structure of the metal complex shown. ]

Ar ^R2 is preferably a structural unit represented by formulas (Z-R42) to (Z-R54).

［式中、
Ｒ^D1、Ｒ^D2、Ｒ^D1１、Ａｒ^Ｒ１、−Ａ^D1---Ａ^D2−、−Ａ^D3---Ａ^D4−、Ｚ^Ｄ、Ｄｅｎｄおよびｎｐ４は、前記と同じ意味を表す。］

[In the formula,
^{R D1, R D2, R D11} , Ar R1, -A D1 --- A D2 -, - A D3 --- A D4 -, Z D, Dend and np4 are as defined above. ]

  The polymer compound containing a structural unit having a structure of a metal complex exhibiting red phosphorescence contained in the composition of the present invention can be represented by the above formula (Z-R42), (Z-R43) or (Z-R48). It is preferable to include the structural unit to be contained, and it is more preferable to include the structural unit represented by the following formula (Ir-41).

［式中、Ｒ^D2は前記と同じ意味を表す。］

[Wherein, R ^D2 represents the same meaning as described above. ]

  Examples of metal complexes that exhibit red phosphorescence include metal complexes represented by formulas (Z-R31) to (Z-R38).

［式中、
Ｒ^D5およびＲ^D6は、それぞれ独立に、水素原子、アルキル基、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。複数存在するＲ^D5は、同一でも異なっていてもよいが、少なくとも１つのＲ^D5は前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基である。複数存在するＲ^D6は、同一でも異なっていてもよいが、少なくとも１つのＲ^D6は前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基である。
Ｒ^D12は、水素原子、アルキル基、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。複数存在するＲ^D12は、同一でも異なっていてもよい。
Ｄｅｎｄは、前記式（Ｄｅｎｄ−Ａ）または（Ｄｅｎｄ−Ｂ）で表される基を表す。
Ｚ^Hは、窒素原子または＝Ｃ（−Ｒ^Ｄ6）−を表す。
−Ａ^D9---Ａ^D10−および−Ａ^D11---Ａ^D12−は、それぞれ独立に、アニオン性の２座配位子を表し、Ａ^D9、Ａ^D10、Ａ^D11およびＡ^D12は、それぞれ独立に、イリジウム原子と結合する炭素原子、酸素原子または窒素原子を表す。
ｎ_Ｄ１は１、２または３であり、ｎ_Ｄ２は１、２または３を表す。］

[In the formula,
R ^D5 and R ^D6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups have a substituent It is also good. Although a plurality of R ^D5 may be the same or different, at least one R ^D5 is a group represented by the formula (Dend-A) or (Dend-B). Although a plurality of R ^D6 may be the same or different, at least one R ^D6 is a group represented by the above formula (Dend-A) or (Dend-B).
R ^D12 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. Plural R ^D12 may be the same or different.
Dend represents a group represented by the formula (Dend-A) or (Dend-B).
Z ^H represents a nitrogen atom or = C (-R ^D6 )-.
-A ^D9 --- A ^D10 - and -A ^D11 --- A ^D12 - independently represent a bidentate ligand of the ^{anionic, A D9, A D10, A} D11 and A ^D12, respectively Independently, it represents a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom.
n _D1 represents 1, 2 or 3, and n _D2 represents 1, 2 or 3. ]

R ^D12 is preferably a hydrogen atom, an alkyl group or an aryl group, and these groups may have a substituent.

Examples of the anionic bidentate ligand represented by -A ^D9 --- A ^D10- include the bidentate ligands represented below.

［式中、Ｒ^D11およびＤｅｎｄは、前記と同じ意味を表す。Ｚ^Ｏは、窒素原子または＝Ｃ（−Ｒ^D11）−を表す。＊は、イリジウム原子との結合部位を表す。］

[Wherein, R ^D11 and Dend represent the same meaning as described above. Z ^O represents a nitrogen atom or = C (-R ^D11 )-. * Represents a binding site to an iridium atom. ]

Examples of the anionic bidentate ligand represented by -A ¹¹ --- A ^D12- include a bidentate ligand represented by the following.

［式中、ＲおよびＲ^D11は、前記と同じ意味を表す。Ｚ^Ｐは、窒素原子または＝Ｃ（−Ｒ^D11）−を表す。＊は、イリジウム原子との結合部位を表す。Ｘは、酸素原子または硫黄原子を表す。］

[Wherein, R and R ^D11 represent the same meaning as described above. Z ^P represents a nitrogen atom or = C (-R ^D11 )-. * Represents a binding site to an iridium atom. X represents an oxygen atom or a sulfur atom. ]

  The metal complex exhibiting red phosphorescence contained in the composition of the present invention is preferably a metal complex represented by the following formula (Ir-1), (Ir-2) or (Ir-3), The metal complex represented by the formula (Ir-3) is more preferable.

［式中、Ｒ^D5、−Ａ^D9---Ａ^D10−およびｎ_Ｄ１は、前記と同じ意味を表す。］

[Wherein, R ^D5 , -A ^D9 --- A ^D10 -and n _D1 represent the same meaning as described above. ]

［式中、Ｒ^D6、−Ａ¹¹---Ａ^D12−およびｎ_Ｄ２は、前記と同じ意味を表す。］

[Wherein, R ^D6 , -A ¹¹ --- A ^D12 -and n _D2 represent the same meaning as described above. ]

[式中、Ｒ^D6は、前記と同じ意味を表す。ｎ_Ｄ３は１または２を表す。]

[Wherein, R ^D6 represents the same meaning as described above. n _D3 represents 1 or 2; ]

  The metal complex represented by the formula Ir-1 is preferably a metal complex represented by the formulas Ir-12 and Ir-13. The metal complex represented by the formula Ir-2 is preferably a metal complex represented by the formula Ir-21. The metal complex represented by the formula Ir-3 is preferably a metal complex represented by the formula Ir-31 to Ir-33.

［式中、Dendは、式(Dend-A)で表される基を表す。ｎ_D3は１または２を表す。］

[Wherein, Dend represents a group represented by the formula (Dend-A). n _D3 represents 1 or 2; ]

  As a metal complex which shows red phosphorescence luminescence, the metal complex shown below is mentioned, for example.

  The polymer compound that exhibits blue fluorescence, the polymer compound that exhibits green fluorescence, and the polymer compound that includes a structural unit having a structure of a metal complex that exhibits red phosphorescence emit 1 of the structural unit represented by the formula (Y) It may contain only a species, or two or more species.

  The polymer compound that exhibits blue fluorescence, the polymer compound that exhibits green fluorescence, and the polymer compound that includes a structural unit having a structure of a metal complex that exhibits red phosphorescence emit 1 of the structural units represented by formula (X) It may contain only a species, or two or more species.

  It is preferable that the high molecular compound which shows blue fluorescence emission contains the structural unit represented by Formula (Y), and the structural unit represented by Formula (X). The total of the constituent unit represented by the formula (Y) and the constituent unit represented by the formula (X) is preferably 70 mol% or more with respect to all the constituent units contained in the polymer compound, 90 mol % Or more is more preferable, and 100 mol% is more preferable. In addition, the constituent unit represented by the formula (Y) is preferably 50 mol% or more and 100 mol% or less, and 70 mol% or more and 98 mol% or less with respect to all the constituent units contained in the polymer compound. It is more preferable that The structural unit represented by the formula (X) is preferably 0 mol% or more and 50 mol% or less, and 2 mol% or more and 30 mol% or less with respect to all the structural units contained in the polymer compound. Is more preferred.

  The polymer compound that exhibits green fluorescence preferably contains a constituent unit represented by the formula (Y) and a constituent unit represented by the formula (G), and the constituent unit represented by the formula (Y) It is more preferable that the structural unit represented by Formula (X) and the structural unit represented by Formula (G) are included. The constituent unit represented by the formula (G) is preferably 0.1 mol% or more and 10 mol% or less, preferably 0.1 mol% or more and 5 mol%, with respect to all the constituent units contained in the polymer compound. It is more preferable that The total of the constituent unit represented by the formula (Y) and the constituent unit represented by the formula (X) is 90 mol% or more and 99.9 mol% or less based on all the constituent units contained in the polymer compound It is more preferable that it is 95 to 99.9 mol%.

  A polymer compound containing a structural unit having a structure of a metal complex exhibiting red phosphorescence emission can be represented by the structural unit represented by the formula (Y), the structural unit represented by the formula (R) and the formula (R2). Preferably, it contains at least one structural unit selected from the group consisting of the structural units represented by the formula (Y), a structural unit represented by the formula (Y), a structural unit represented by the formula (X), and It is more preferable to include at least one structural unit selected from the group consisting of the structural unit represented by R) and the structural unit represented by formula (R2), and the structural unit represented by formula (Y) It is more preferable that the structural unit represented by Formula (X) and the structural unit represented by Formula (R) are included. At least one structural unit selected from the group consisting of the structural unit represented by the formula (R) and the structural unit represented by the formula (R2) is preferably 0. 1 or less with respect to all the structural units contained in the polymer compound. It is preferable that it is 01 mol% or more and 20 mol% or less, more preferably 0.01 mol% or more and 5 mol% or less, and still more preferably 0.01 mol% or more and 2.5 mol% or less. The total of the constituent unit represented by the formula (Y) and the constituent unit represented by the formula (X) is 80 mol% or more and 99.99 mol% or less with respect to all the constituent units contained in the polymer compound Is preferably 95 mol% to 99.99 mol%, and more preferably 97.5 mol% to 99.99 mol%.

  When the composition of the present invention contains a polymer compound that exhibits blue fluorescence emission, a polymer compound that exhibits green fluorescence emission, and a metal complex that exhibits red phosphorescence emission, the compatibility is more excellent, and therefore, the color exhibits high blue fluorescence emission. It is preferable that the molecular compound and the high molecular compound which exhibits green fluorescence include the common constitutional unit represented by the formula (Y) and the common constitutional unit represented by the formula (X). The sum of the common structural unit represented by the formula (Y) and the common structural unit represented by the formula (X) contained in the polymer compound exhibiting blue fluorescence and the polymer compound exhibiting green fluorescence is respectively The amount is preferably 70 mol% or more, more preferably 80 mol% or more, and still more preferably 94 mol% or more based on all the structural units contained in the polymer compound of the above.

  When the composition of the present invention contains a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a polymer compound that includes a structural unit having a structure of a metal complex that exhibits red phosphorescence, it is compatible The polymer compound that exhibits a blue fluorescence, the polymer compound that exhibits green fluorescence, and the polymer compound that includes a structural unit having a metal complex structure that exhibits red phosphorescence are represented by the formula (Y). It is preferable to include a common structural unit and a common structural unit represented by Formula (X). A common compound represented by the formula (Y) contained in a polymer compound that exhibits a blue fluorescence, a polymer compound that exhibits a green fluorescence, and a polymer unit that includes a structural unit having the structure of the metal complex that exhibits the red phosphorescence The total of the structural unit and the common structural unit represented by the formula (X) is preferably 70 mol% or more, more preferably 80 mol% or more, based on all the structural units contained in each polymer compound. Is more preferably 94 mol% or more.

  When the composition of the present invention contains a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a metal complex that exhibits red phosphorescence, the polymer compound that exhibits blue fluorescence generally has a ratio of 0. 1000 to 99.9899% by weight, the polymer compound exhibiting green fluorescence is 0.0100 to 99.8999% by weight, and the metal complex exhibiting red phosphorescence is 0.0001 to 99.8900% by weight. Since the light emission efficiency of the light emitting device containing the composition is excellent, the polymer compound exhibiting blue fluorescence is 0.5000 to 99.9495% by weight, and the polymer compound exhibiting green fluorescence is 0.0050 to 99.4995% The metal complex exhibiting red phosphorescence is preferably 0.0005 to 10.000% by weight, and the polymer compound exhibiting blue fluorescence is 0.50 to 99.94% by weight It is more preferable that the polymer compound showing green fluorescence emission is 0.05 to 99.49% by weight, and the metal complex showing red phosphorescence emission is 0.01 to 10.0% by weight. The molecular compound is 0.50 to 99.90% by weight, the high molecular compound showing green fluorescence is 0.05 to 99.45% by weight, and the metal complex showing red phosphorescence is 0.05 to 10.0% by weight It is further preferred that

  When the composition of the present invention contains a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a metal complex that exhibits red phosphorescence, a polymer compound that exhibits blue fluorescence, and green fluorescence The emission color can be adjusted by adjusting the weight ratio of the polymer compound to be shown and the metal complex that exhibits red phosphorescence.

  When the composition of the present invention contains a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a polymer compound that includes a structural unit having a metal complex structure that exhibits red phosphorescence, A polymer compound exhibiting blue fluorescence emission is 0.010 to 99.989 wt%, a polymer compound exhibiting green fluorescence emission 0.010 to 99.989 wt%, and a structure having a structure of a metal complex exhibiting red phosphorescence emission The polymer compound containing the unit is 0.001 to 99.980% by weight, and the polymer compound showing blue fluorescence emission is 0.10 to 99.% because the light emitting device containing the composition of the present invention has excellent luminous efficiency. The polymer compound that exhibits 89% by weight of green fluorescence emits 0.10 to 99.89% by weight, and the polymer compound that includes a structural unit having a structure of a metal complex that emits red phosphorescence 0.01 to 99.8 It is preferable that the weight ratio is 0.1% to 99.8% by weight of the polymer compound showing blue fluorescence, 0.1 to 99.8% by weight of the polymer compound showing green fluorescence, and red phosphorescence It is more preferable that the high molecular compound containing the structural unit which has a structure of the metal complex shown is 0.1 to 99.8 weight%.

  When the composition of the present invention contains a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a polymer compound that has a structural unit having a metal complex structure that exhibits red phosphorescence, the blue fluorescence Adjusting the weight ratio of a polymer compound that emits light, a polymer compound that emits green fluorescence, and a polymer compound that includes a structural unit having a structure of a metal complex that emits red phosphorescence, thereby adjusting emission color Is possible.

<Method for producing polymer compound>
Next, a polymer compound exhibiting blue fluorescence, a polymer compound exhibiting green fluorescence, and a polymer compound having a structural unit having a metal complex structure exhibiting red phosphorescence contained in the composition of the present invention are produced. The method will be described.

  In the present specification, the compounds used for producing the polymer compound of the present invention may be collectively referred to as "raw material monomers". The polymer compound of the present invention can be produced by a known condensation polymerization reaction.

The polymer compound which exhibits blue fluorescence is selected from, for example, a compound represented by the formula (M-Y1), a compound represented by the formula (M-Y2) and a compound represented by the formula (M-X1) It can be produced by condensation polymerization of at least one or more compounds.
Examples of the polymer compound that exhibits green fluorescence include a compound represented by formula (M-G1), a compound represented by formula (M-Y1), a compound represented by formula (M-Y2), and a compound represented by formula (M-Y2) It can be produced by condensation polymerization of at least one compound selected from the compounds represented by -X1).
The polymer compound containing a constitutional unit having a structure of a metal complex exhibiting red phosphorescence emission is, for example, a compound represented by the formula (M-R1), a compound represented by the formula (M-R2), a formula (M-Y1) And at least one compound selected from a compound represented by the formula (M-Y2) and a compound represented by the formula (M-X1).

［式中、Ar^Y1、Ar^X1、Ar^X2、Ar^X3、Ar^X4、Ar^X5、R^X1、R^X2、R^X3、a^X1、a^X2、Ar^G、Ar^R、Ar^R2は前記と同じ意味である。Ｚ^C1〜Ｚ^C9は、それぞれ独立に、置換基Ａ群および置換基Ｂ群からなる群から選ばれる基を示す。］

[Wherein, Ar ^Y1 , Ar ^X1 , Ar ^X2 , Ar ^X3 , Ar ^X4 , Ar ^X5 , R ^X1 , R ^X2 , R ^X3 , a ^X1 , a ^X2 , Ar ^G , Ar ^R , Ar ^R2 have the same meaning as described above. It is. Z ^C1 to Z ^C9 each independently represents a group selected from the group consisting of Substituent Group A and substituent group B. ]

For example, when Z ^C1 and Z ^C2 are a group selected from Substituent Group A, Z ^C3 , Z ^C4 , Z ^C5 , Z ^C6 , Z ^C7 , Z ^C8 and Z ^C9 are groups selected from Substituent Group B Choose For example, when Z ^C1 and Z ^C2 are a group selected from Substituent Group B, Z ^C3 , Z ^C4 , Z ^C5 , Z ^C6 , Z ^C7 , Z ^C8 and Z ^C9 are groups selected from Substituent Group A Choose Also, for example, when Z ^C1 , Z ^C3 , Z ^C5 , Z ^C7 and Z ^C9 are a group selected from Substituent Group A, Z ^C2 , Z ^C4 , Z ^C6 and Z ^C8 are selected from Substituent Group B Select a group.

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

As a group represented by -B (OR <^C2> ) ₂ , the group represented by a following formula is illustrated.

  The compound having a group selected from the substituent group A and the compound having a group selected from the substituent group B are condensation-polymerized by a known coupling reaction to form a group selected from the substituent group A and a substituent group B And a carbon atom bonded to a group selected from Therefore, if a compound having two groups selected from the substituent group A and a compound having two groups selected from the substituent group B are subjected to a known coupling reaction, condensation polymerization results in condensation of these compounds. Polymers can be obtained.

  The condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, and may optionally be carried out in the coexistence of a phase transfer catalyst.

  As a catalyst, for example, dichlorobis (triphenylphosphine) palladium, dichlorobis (tris-o-methoxyphenylphosphine) palladium, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium acetate and the like Such as palladium complexes of nickel, nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, nickel complexes such as [bis (1,4-cyclooctadiene)] nickel, etc. Metal complexes; complexes in which these transition metal complexes further have a ligand such as triphenylphosphine, tri-o-tolylphosphine, tri (tert-butylphosphine), tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl and the like Be The catalysts may be used alone or in combination of two or more.

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

  Examples of the base include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride and tripotassium phosphate; organic bases such as tetrabutyl ammonium fluoride and tetrabutyl ammonium hydroxide . The bases may be used alone or in combination of two or more.

  Examples of phase transfer catalysts include tetrabutyl ammonium chloride and tetrabutyl ammonium bromide. The phase transfer catalyst may be used alone or in combination of two or more.

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

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

  Examples of the solvent include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water. The solvents may be used alone or in combination of two or more.

  The amount of the solvent used is usually 10 to 100000 parts by weight with respect to a total of 100 parts by weight of the raw material monomers.

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

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

  The synthesis method of the metal complex which exhibits red phosphorescence can be synthesized according to a known method, for example, the method described in WO 2002/066552 and the like.

  Moreover, the synthesis | combining method of the structural unit which has a structure of the metal complex which shows red phosphorescence emission can be synthesize | combined in accordance with a well-known method, for example, the method as described in Unexamined-Japanese-Patent No. 2011-105701 grade.

  The composition of the present invention further contains at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent. May be

  The composition of the present invention containing a solvent (hereinafter sometimes referred to as "ink") is suitable for producing 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 in the case where a solution such as an inkjet printing method is applied to a printing method via a discharge device, in order to prevent clogging at the discharge and flying deflection. And preferably 1 to 20 mPa · s at 25 ° C.

  The solvent contained in the ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. As the solvent, for example, chlorinated solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc .; ether solvents such as tetrahydrofuran, dioxane, anisole, 4-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellsolve acetate, methyl benzoate and phenyl acetate System solvents; ethylene glycol, Polyhydric alcohol solvents such as serine and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N, N-dimethylformamide and the like And amide solvents of the following. The solvents may be used alone or in combination of two or more.

  In the ink, the compounding amount of the solvent is a structural unit having a structure of a polymer compound showing blue fluorescence, a polymer compound showing green fluorescence, and a metal complex showing red phosphorescence or a metal complex showing red phosphorescence The amount is usually 1000 to 100000 parts by weight, preferably 2000 to 20000 parts by weight, with respect to a total of 100 parts by weight with the polymer compound containing

As a method of producing the ink,
[1] A polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a polymer compound having a structural unit having a metal complex that exhibits red phosphorescence or a metal complex that exhibits red phosphorescence Method of dissolving in one or more solvents after mixing in solid state,
[2] Ink (B) in which a polymer compound exhibiting blue fluorescence is dissolved in one or more solvents, ink (G) in which a polymer compound exhibiting green fluorescence is dissolved in one or more solvents, and red A method of mixing an ink (R) in which a polymer compound having a structural unit having a structure of a metal complex exhibiting phosphorescence emission or a metal complex exhibiting red phosphorescence emission is dissolved in one or more solvents;
[3] An ink (BG) dissolved in one or more solvents after mixing in a solid state a polymer compound that exhibits blue fluorescence and a polymer compound that exhibits green fluorescence, and a metal complex or red that exhibits red phosphorescence A method of mixing an ink (R) in which a polymer compound containing a structural unit having a structure of a metal complex exhibiting phosphorescence is dissolved in one or more solvents;
[4] Ink (B) in which a polymer compound showing blue fluorescence is dissolved in a solvent of one or more solvents, a polymer compound showing green fluorescence and a metal complex or red phosphorescence showing red phosphorescence A method of mixing, in a solid state, a polymer compound containing a structural unit having a structure of a metal complex having a structure of
[5] One or more kinds of solvents after mixing in a solid state a polymer compound having a structure of blue fluorescent light emission and a metal complex showing red phosphorescent light emission or a metal complex showing red phosphorescent light emission. A method of mixing an ink (BR) dissolved in the ink, and an ink (G) in which a polymer compound exhibiting green fluorescence is dissolved in one or more solvents;
[6] Ink (B) in which a polymer compound exhibiting blue fluorescence is dissolved in one or more solvents, ink (G) in which a polymer compound exhibiting green fluorescence is dissolved in one or more solvents, and red Prepare an ink (R) in which a polymer compound having a structural unit having a structure of a metal complex exhibiting phosphorescence emission or a metal complex exhibit red phosphorescence emission is prepared in each of one or more solvents, and using a known coating device And the method of mixing while coating.

  As the method for producing the ink, the production method of [1] is preferable because the production of the ink is easy.

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

  Examples of the polymer compound include polyvinylcarbazole and derivatives thereof; polyarylenes having an aromatic amine structure in the side chain or main chain and derivatives thereof. The macromolecular compound may be a compound having an electron accepting moiety bound thereto. Examples of the electron accepting moiety include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone and the like, with preference given to fullerene.

  In the composition of the present invention, the compounding amount of the hole transport material is a polymer compound showing blue fluorescence, a polymer compound showing green fluorescence, and a metal complex showing red phosphorescence or a metal showing red phosphorescence The amount is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, based on 100 parts by weight in total of the polymer compound containing a structural unit having a complex structure.

  The hole transport material may be used alone or in combination of two or more.

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

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

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

  In the composition of the present invention, the compounding amount of the electron transport material is a polymer compound showing blue fluorescence, a polymer compound showing green fluorescence, a metal complex showing red phosphorescence, or a metal complex showing red phosphorescence The amount is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, based on 100 parts by weight in total with the polymer compound containing a structural unit having the structure of

  The electron transporting material may be used alone or in combination of two or more.

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

  As a low molecular weight compound, metal phthalocyanines, such as copper phthalocyanine; Carbon; Metal oxides, such as molybdenum and tungsten; Metal fluorides, such as lithium fluoride, sodium fluoride, cesium fluoride, potassium fluoride, etc. are mentioned, for example.

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

  In the composition of the present invention, the compounding amounts of the hole injecting material and the electron injecting material are respectively a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a metal complex that exhibits red phosphorescence or The amount is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, based on 100 parts by weight in total of the polymer compound containing a structural unit having a structure of a metal complex exhibiting red phosphorescence.

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

[Ion doping]
When the hole injecting material or the electron injecting material contains a conductive polymer, the conductivity of the conductive polymer is preferably 1 × 10 ⁻⁵ S / cm to 1 × 10 ³ S / cm. The conductive polymer can be doped with an appropriate amount of ions in order to bring the conductivity of the conductive polymer into such a range.

  The type of ion to be doped is an anion if it is a hole injecting material, and a cation if it is an electron injecting material. Examples of the anion include polystyrene sulfonate ion, alkyl benzene sulfonate ion and camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion and tetrabutyl ammonium ion.

  The ion to be doped may be one kind or two or more kinds.

[Light emitting material]
Light emitting materials are classified into low molecular weight compounds and high molecular weight compounds. The light emitting material may have a crosslinking group.

  The low molecular weight compounds include, for example, naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and a triplet light emitting complex having iridium, platinum or europium as a central metal.

  As the polymer compound, for example, phenylene group, naphthalenediyl group, fluorenedyl group, phenanthrendiyl group, dihydrophenanthrendiyl group, group represented by formula (X), carbazole diyl group, phenoxazine diyl group, phenothiazine diyl Examples thereof include polymer compounds containing a group, an anthracenediyl group, a pyrenediyl group and the like.

  The light emitting material may include low molecular weight compounds and high molecular weight compounds, and preferably includes triplet light emitting complexes and high molecular weight compounds.

  As a triplet light emission complex, the metal complex shown below is mentioned, for example.

  In the composition of the present invention, the content of the light emitting material is a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a metal complex that exhibits red phosphorescence or a metal complex that exhibits red phosphorescence. The amount is usually 0.1 to 400 parts by weight with respect to 100 parts by weight in total with a polymer compound containing a structural unit having a structure.

[Antioxidant]
The antioxidant includes a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a polymer having a structural unit having a metal complex that exhibits red phosphorescence or a metal complex that exhibits red phosphorescence. Any compound that is soluble in the same solvent as the compound and does not inhibit light emission and charge transport may be used, and examples include phenolic antioxidants and phosphorus antioxidants.

  In the composition of the present invention, the compounding amount of the antioxidant is a polymer compound that exhibits blue fluorescence, a polymer compound that exhibits green fluorescence, and a metal complex that exhibits red phosphorescence or a metal complex that exhibits red phosphorescence. The amount is usually 0.001 to 10 parts by weight with respect to 100 parts by weight in total with a polymer compound containing a structural unit having the structure of

  The antioxidant may be used alone or in combination of two or more.

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

  The film also includes an insolubilized film in which the polymer compound contained in the composition of the present invention is insolubilized in a solvent by crosslinking. The insolubilized film is a film obtained by crosslinking the polymer compound contained in the composition of the present invention by an external stimulus such as heating or light irradiation. Since the insolubilized film is substantially insoluble in the solvent, it can be suitably used for laminating the light emitting element.

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

  The type of light used for light irradiation to crosslink the film is, for example, ultraviolet light, near ultraviolet light, and visible light.

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

  The film is formed using an ink, for example, spin coating method, casting method, microgravure coating method, gravure coating method, bar coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method And flexo printing, offset printing, ink jet printing, capillary coating, and nozzle coating.

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

<Light emitting element>
The light emitting device of the present invention is a light emitting device containing the composition of the present invention, and the light emitting device includes, for example, a light emitting device containing the composition of the present invention and a polymer compound contained in the composition of the present invention. There are light emitting elements crosslinked intramolecularly, intermolecularly, or both.
The light emitting device of the present invention has, for example, an electrode comprising an anode and a cathode, and a layer containing the composition of the present invention provided between the electrodes.

[Layer structure]
The layer containing the composition of the present invention is usually one or more of a light emitting layer, a hole transporting layer, a hole injecting layer, an electron transporting layer and an electron injecting layer, preferably a light emitting layer. Each of these layers contains a light emitting material, a hole transporting material, a hole injecting material, an electron transporting material, and an electron injecting material. These layers are prepared by dissolving the light emitting material, the hole transporting material, the hole injecting material, the electron transporting material, and the electron injecting material in the above-mentioned solvent, preparing the ink, and using the same film as the above-mentioned film It can be formed using the method.

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

  As materials of the hole transport layer, the electron transport layer, the light emitting layer, the hole injection layer, and the electron injection layer, in addition to the composition of the present invention, the hole transport material, the electron transport material, the light emitting material , Hole injecting materials, and electron injecting materials.

  The material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer are respectively used in forming the hole transport layer, the electron transport layer, and the layer adjacent to the light emitting layer in the preparation of the light emitting device When it is dissolved in the solvent, it is preferable that the material has a crosslinking group in order to avoid the dissolution of the material in the solvent. After each layer is formed using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

  In the case of using a low molecular weight compound as a method of forming each layer such as a light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, an electron injection layer in the light emitting device of the present invention, vacuum evaporation from powder, for example The method includes film formation from a solution or a molten state, and when using a polymer compound, for example, film formation from a solution or a molten state.

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

[Substrate / electrode]
The substrate in the light emitting element may be any substrate that can form an electrode and does not change chemically when forming an organic layer, and is, for example, a substrate made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, it is preferred that the electrode furthest from the substrate be transparent or translucent.

  Examples of the material of the anode include conductive metal oxides and semitransparent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc. Conductive compounds; complexes of silver, palladium and copper (APC); NESA, gold, platinum, silver, copper.

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

[Use]
In order to obtain planar light emission using a light emitting element, a planar anode and a cathode may be arranged to overlap. In order to obtain pattern-like light emission, a method of installing a mask provided with a pattern-like window on the surface of a planar light-emitting element is used. 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 so that several electrodes can be turned ON / OFF independently, a segment type display device capable of displaying numbers, characters, etc. 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 orthogonal to each other. Partial color display and multi-color display can be performed by a method of separately coating a plurality of types of light emitting compositions different from each other and a method of 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 as displays of computers, televisions, portable terminals, and the like. A planar light emitting element can be suitably used as a planar light source for backlight of a liquid crystal display device or a planar light source for illumination. If a flexible substrate is used, it can be used as a curved light source and a display device.

  Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to these examples.

[Measuring method of molecular weight]
In this example, the polystyrene equivalent number average molecular weight (Mn) and the polystyrene equivalent weight average molecular weight (Mw) were determined by GPC (manufactured by Shimadzu Corporation, trade name: LC-10 Avp). The polymer compound to be measured was dissolved in tetrahydrofuran to a concentration of about 0.5% by weight, and 30 μL was injected into GPC. Tetrahydrofuran was used for the mobile phase of GPC, and it flowed at the flow rate of 0.6 mL / min. As a column, two TSKgel SuperHM-H (manufactured by Tosoh Corporation) and one TSKgel SuperH2000 (manufactured by Tosoh Corporation) were connected in series. As a detector, a differential refractive index detector (manufactured by Shimadzu Corporation, trade name: RID-10A) was used.

[Method of measuring emission spectrum peak]
In the present example, the maximum peak wavelength of the fluorescence emission spectrum and the maximum peak wavelength of the phosphorescence emission spectrum were measured by a spectrophotometer (FP6500: JASCO Corporation). In the case of measuring the maximum peak wavelength of the polymer compound, the polymer compound alone was deposited on a quartz substrate to a film thickness of about 65 nm was used as a sample. When measuring the maximum peak wavelength of the metal complex, a xylene solution of about 40 μM was used as a sample. As excitation light, UV light of wavelength 325 nm was used.

[Method for obtaining raw material monomer]
Compound 1a was obtained according to the method described in WO2011-093428.
Compound 1b was obtained according to the method described in WO2012-086671.
Compound 1c was obtained according to the method described in WO2012-086671.
Compound 2b was obtained according to the method described in JP-A-2008-106241.
Compound 2c was obtained according to the method described in WO2012-104579.
Compound 2d was obtained according to the method described in JP-A-2010-10438.
Compound 3 was obtained according to the method described in JP-A-2012-144721.
Compound 4 was obtained according to the method described in WO2005-049546.
Compound 5 was obtained according to the method described in WO2004-099340.
Compound 6 was obtained according to the method described in WO2012-086670.
Compound 7 was obtained according to the method described in JP-A-2010-31259.
Compound 8 was obtained according to the method described in JP-A-2012-122062. Compound 8 is a mixture of compound 8a and compound 8b.
Compound 9 was obtained according to the method described in JP-A-2012-131993.
Compound 11 was obtained according to the method described in WO2008-143272.
Compound 12 was obtained according to the method described in JP-A-2011-105701.
Compounds 1d, 1e, 2a and 10 were obtained according to known methods.
Compound 13 was obtained according to the method described below.

Synthesis Example 1: Synthesis of Polymer Compound 1
(Step 1) After setting the inside of the reaction vessel to an inert gas atmosphere, compound 1a (2.96 mmol), compound 2a (0.75 mmol), compound 4 (1.80 mmol), compound 2b (0.45 mmol), dichlorobis Triphenylphosphine) palladium (2.1 mg, 0.0030 mmol) and toluene (62 ml) were added and heated to 105.degree.
(Step 2) A 20% by weight aqueous solution of tetraethylammonium hydroxide (10 ml) was added dropwise to the reaction mixture, and the mixture was refluxed for 4.5 hours.
(Step 3) After the reaction, phenylboronic acid (36.8 mg, 0.30 mmol) and dichlorobis (triphenylphosphine) palladium (2.1 mg, 0.0030 mmol) were added thereto and refluxed for 16.5 hours.
(Step 4) Thereafter, an aqueous solution of sodium diethyldithiacarbamate was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with water, twice with a 3% by weight aqueous acetic acid solution, and twice with water, and the obtained solution was added dropwise to methanol, whereby a precipitate formed. The precipitate was dissolved in toluene and purified by sequentially passing through an alumina column and a silica gel column.
The obtained solution was added dropwise to methanol and stirred, and then the obtained precipitate was collected by filtration and dried to obtain 3.12 g of polymer compound 1. The Mn of the polymer compound 1 was 7.8 × 10 ⁴ , and the Mw was 2.6 × 10 ⁵ .
The polymer compound 1 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1a, the structural unit derived from the compound 2a, the structural unit derived from the compound 4, and the compound 2b It is a copolymer in which the structural unit to be derived is constituted at a molar ratio of 50: 12.5: 30: 7.5.

Synthesis Example 2 Synthesis of Polymer Compound 2
“(Step 1) in the synthesis of the polymer compound 1” is “compound 1b (1.98 mmol), compound 3 (1.00 mmol), compound 2c (0.78 mmol) after setting the reaction vessel in an inert gas atmosphere, Compound 6 (0.12 mmol), Compound 5 (0.04 mmol), Compound 7 (0.06 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg, 0.0020 mmol) and toluene (47 ml) Were mixed and heated to 105 ° C. ",
In Step 2 of the synthesis of Polymer Compound 1, “20% by weight aqueous tetraethylammonium hydroxide solution (7.5 ml) was added dropwise to the reaction solution and refluxed for 3 hours”.
(Step 3) in the synthesis of macromolecular compound 1 was prepared by adding, after reaction, phenylboronic acid (26.2 mg, 0.21 mmol), 20 wt% aqueous tetraethylammonium hydroxide solution (7.5 ml) and dichlorobis [tris (2-Methoxyphenyl) phosphine] palladium (1.8 mg, 0.0020 mmol) was added and refluxed for 18 hours. "
A polymer compound 2 was obtained in the same manner as in the synthesis of the polymer compound 1 except that 1.23 g of a polymer compound 2 was obtained. The Mn of the polymer compound 2 was 8.9 × 10 ⁴ and the Mw was 2.4 × 10 ⁵ .
The polymer compound 2 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1b, the structural unit derived from the compound 3, the structural unit derived from the compound 2c, and the compound 6 The structural unit to be derived, the structural unit derived from Compound 5, and the structural unit derived from Compound 7 are configured at a molar ratio of 50: 25: 19.5: 3: 1: 1.5 Copolymer. The emission spectrum peak of the polymer compound 2 was 456 nm.

Synthesis Example 3 Synthesis of Polymer Compound 3
(Step 1) After setting the inside of the reaction vessel to an inert gas atmosphere, compound 1b (26.76 mmol), compound 2c (24.28 mmol), compound 5 (2.76 mmol), compound 8 (0.55 mmol), dichlorobis [ Tris (2-methoxyphenyl) phosphine] palladium (4.9 mg, 0.0055 mmol) and toluene (540 ml) were added and heated to 105 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (94 ml) was added dropwise to the reaction mixture, and the mixture was refluxed for 8 hours.
(Step 3) After the reaction, add thereto phenylboronic acid (0.34 g, 2.79 mmol) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (4.9 mg, 0.0055 mmol) to obtain 15.5 Refluxed for time.
(Step 4) Thereafter, an aqueous solution of sodium diethyldithiacarbamate was added thereto, and the mixture was stirred at 40 ° C. for 4 hours. After cooling, the reaction solution was washed once with water, twice with 10 wt% aqueous hydrochloric acid, twice with 3 wt% aqueous ammonia solution, twice with water, and purified by passing through an alumina column and a silica gel column in this order. . The obtained solution was dropped into methanol and stirred, and then the obtained precipitate was collected by filtration and dried to obtain 20.2 g of polymer compound 3. The Mn of the polymer compound 3 was 1.0 × 10 ⁵ , and the Mw was 2.4 × 10 ⁵ .
The polymer compound 3 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1b, the structural unit derived from the compound 2c, the structural unit derived from the compound 5, and the compound 8 It is a copolymer in which the constituent units to be derived are constituted at a molar ratio of 50: 44: 5: 1. The emission spectrum peak of the polymer compound 3 was 511 nm.

Synthesis Example 4 Synthesis of Polymer Compound 4
[Step 1] in the synthesis of the polymer compound 1 is “compound 1c (2.09 mmol), compound 1e (0.82 mmol), compound 2d (1.91 mmol) after setting the reaction vessel in an inert gas atmosphere Compound 5 (0.44 mmol), compound 9 (0.59 mmol), dichlorobis (triphenylphosphine) palladium (2.1 mg, 0.0029 mmol) and toluene (64 ml) were mixed and heated to 105 ° C. ”
In the synthesis of Polymer Compound 1 (Step 2), “20% by weight aqueous tetraethylammonium hydroxide solution (10 ml) was added dropwise to the reaction solution and refluxed for 4 hours”.
(Step 3) in the synthesis of macromolecular compound 1 was prepared by adding, after reaction, phenylboronic acid (35.8 mg, 0.29 mmol), 20% by weight aqueous tetraethylammonium hydroxide solution (10 ml) and dichlorobis (triphenylphosphine). ) Palladium was added (1.1 mg, 0.0015 mmol) and allowed to reflux for 18 h. "
The procedure of synthesis of polymer compound 1 was repeated, except that 2.11 g of polymer compound 4 was obtained. The Mn of the polymer compound 4 was 1.0 × 10 ⁵ , and the Mw was 2.8 × 10 ⁵ .
The polymer compound 4 is a theoretical unit determined from the amount of the raw materials charged, a constitutional unit derived from the compound 1c, a constitutional unit derived from the compound 1e, a constitutional unit derived from the compound 2d, and the compound 5 It is a copolymer in which the structural unit derived | led-out and the structural unit derived from the compound 9 are comprised by the molar ratio of 36: 14: 32.5: 7.5: 10. The emission spectrum peak of the polymer compound 4 was 484 nm.

Synthesis Example 5 Synthesis of Polymer Compound 5
[Step 1] in the synthesis of polymer compound 1 is “compound 1c (3.32 mmol), compound 1d (1.25 mmol), compound 2d (4.06 mmol) after setting the reaction vessel in an inert gas atmosphere Compound 5 (0.55 mmol), dichlorobis (triphenylphosphine) palladium (6.5 mg, 0.0092 mmol) and toluene (101 ml) were mixed and heated to 105 ° C. ”
In the synthesis of Polymer Compound 1 (Step 2), “20% by weight aqueous tetraethylammonium hydroxide solution (16 ml) was added dropwise to the reaction solution and refluxed for 9 hours”.
In the synthesis of Polymer Compound 1 (Step 3), “After reaction, phenylboronic acid (56.2 mg, 0.46 mmol) and dichlorobis (triphenylphosphine) palladium (3.3 mg, 0.0046 mmol) In addition, it was refluxed for 16 hours. ",
A polymer compound 5 was obtained in the same manner as in the synthesis of the polymer compound 1 except that 4.28 g of a polymer compound 5 was obtained. The Mn of the polymer compound 5 was 7.9 × 10 ⁴ and the Mw was 2.0 × 10 ⁵ .
The polymer compound 5 is a theoretical unit determined from the amount of the raw materials to be charged, a constitutional unit derived from the compound 1c, a constitutional unit derived from the compound 1d, a constitutional unit derived from the compound 2d, and the compound 5 It is a copolymer in which the structural unit to be derived is constituted at a molar ratio of 36: 14: 44: 6. The emission spectrum peak of the polymer compound 6 was 453 nm.

Synthesis Example 6: Synthesis of Polymer Compound 6
[Step 1] in the synthesis of the polymer compound 1 is “compound 1c (15.00 mmol), compound 1e (5.92 mmol), compound 2d (19.02 mmol) after setting the reaction vessel in an inert gas atmosphere, Compound 5 (1.69 mmol), compound 10 (0.42 mmol), dichlorobis (triphenylphosphine) palladium (29.7 mg, 0.042 mmol) and toluene (460 ml) were mixed and heated to 105 ° C. ”
In the synthesis of Polymer Compound 1 (Step 2), “20% by weight aqueous tetraethylammonium hydroxide solution (72 ml) was added dropwise to the reaction solution and refluxed for 5 hours”.
(Step 3) in the synthesis of macromolecular compound 1 was “after reaction, phenylboronic acid (257.6 mg, 2.11 mmol) and dichlorobis (triphenylphosphine) palladium (14.8 mg, 0.021 mmol) In addition, it was refluxed for 15 hours. ",
14.15g of high molecular compounds 6 were obtained by carrying out similarly to the synthesis | combination of the high molecular compounds 1 except setting it as it. The Mn of the polymer compound 6 was 9.8 × 10 ⁴ , and the Mw was 3.1 × 10 ⁵ .
The polymer compound 6 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1c, the structural unit derived from the compound 1e, the structural unit derived from the compound 2d, and the compound 5 It is a copolymer in which the structural unit derived | led-out and the structural unit derived from the compound 10 are comprised by the molar ratio of 36: 14: 45: 4: 1. The emission spectrum peak of the polymer compound 6 was 468 nm.

Synthesis Example 7 Synthesis of Polymer Compound 7
(Step 1) in the synthesis of the polymer compound 1 is “compound 1c (2.12 mmol), compound 1e (0.84 mmol), compound 2d (2.51 mmol) after setting the reaction vessel in an inert gas atmosphere”, Compound 5 (0.30 mmol), compound 8 (0.18 mmol), dichlorobis (triphenylphosphine) palladium (2.1 mg, 0.003 mmol) and toluene (64 ml) were mixed and heated to 105 ° C. ”
(Step 2) in the synthesis of the polymer compound 1 was obtained by adding “20% by weight aqueous tetraethylammonium hydroxide solution (10 ml) dropwise to the reaction solution and refluxing for 5 hours”.
(Step 3) in the synthesis of macromolecular compound 1 was prepared by adding “phenylboronic acid (36.8 mg, 0.30 mmol) and dichlorobis (triphenylphosphine) palladium (1.1 mg, 0.015 mmol) thereto”. In addition, it was refluxed for 18 hours. ",
Except that, in the same manner as in the synthesis of the polymer compound 1, 2.40 g of polymer compound 7 was obtained. The Mn of Polymer Compound 7 was 1.1 × 10 ⁵ and the Mw was 2.9 × 10 ⁵ .
The polymer compound 7 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1c, the structural unit derived from the compound 1e, the structural unit derived from the compound 2d, and the compound 5 It is a copolymer in which the structural unit derived | led-out and the structural unit derived from the compound 8 are comprised by the molar ratio of 36: 14: 42: 5: 3. The emission spectrum peak of the polymer compound 7 was 517 nm.

Synthesis Example 8 Synthesis of Polymer Compound 8
[Step 1] in the synthesis of the polymer compound 1 is “compound 1c (2.56 mmol), compound 1 d (1.01 mmol), compound 2 d (3.10 mmol) after setting the reaction vessel in an inert gas atmosphere”, Compound 5 (0.36 mmol), compound 10 (0.07 mmol), compound 8 (0.07 mmol), dichlorobis (triphenylphosphine) palladium (2.5 mg, 0.0036 mmol) and toluene (70 ml) are mixed to give 105 Heated to ° C. ",
In Step 2 of the synthesis of Polymer Compound 1, “20% by weight aqueous tetraethylammonium hydroxide solution (12 ml) was added dropwise to the reaction solution and refluxed for 5 hours”.
(Step 3) in the synthesis of macromolecular compound 1 is “after reaction, phenylboronic acid (44.0 mg, 0.36 mmol) and dichlorobis (triphenylphosphine) palladium (1.3 mg, 0.0018 mmol) In addition, it was refluxed for 14 hours. ",
Except that, in the same manner as in the synthesis of the polymer compound 1, 2.88 g of polymer compound 8 was obtained. The Mn of the polymer compound 6 was 1.0 × 10 ⁵ , and the Mw was 2.5 × 10 ⁵ .
The polymer compound 8 is a theoretical value determined from the amount of the charged raw materials: a constituent unit derived from the compound 1c, a constituent unit derived from the compound 1d, a constituent unit derived from the compound 2d, and the compound 5 A copolymer comprising a derived structural unit, a structural unit derived from compound 10, and a structural unit derived from compound 8 in a molar ratio of 36: 14: 43: 5: 1: 1 It is. The emission spectrum peak of the polymer compound 8 was 512 nm.

Synthesis Example 9 Synthesis of Polymer Compound 9
[Step 1] in the synthesis of polymer compound 1 is “compound 1c (10.25 mmol), compound 1 d (4.03 mmol), compound 2 d (11.82 mmol) after setting the reaction vessel in an inert gas atmosphere, Compound 5 (1.44 mmol), compound 10 (0.29 mmol), compound 11 (0.86 mmol), dichlorobis (triphenylphosphine) palladium (5.1 mg, 0.0072 mmol) and toluene (316 ml) are mixed to give 105 Heated to ° C. ",
In the synthesis of Polymer Compound 1 (Step 2), “20% by weight aqueous tetraethylammonium hydroxide solution (49 ml) was added dropwise to the reaction solution and refluxed for 6 hours”.
(Step 3) in the synthesis of macromolecular compound 1 was “after reaction, phenylboronic acid (175.7 mg, 1.44 mmol) and dichlorobis (triphenylphosphine) palladium (5.1 mg, 0.0072 mmol) In addition, it was refluxed for 14 hours. ",
Except that, in the same manner as in the synthesis of the polymer compound 1, 11.22 g of polymer compound 9 was obtained. The Mn of the polymer compound 9 was 9.1 × 10 ⁴ , and the Mw was 2.3 × 10 ⁵ .
The polymer compound 9 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1c, the structural unit derived from the compound 1d, the structural unit derived from the compound 2d, and the compound 5 A copolymer in which a structural unit derived from the structural unit derived from the compound 10 and a structural unit derived from the compound 11 have a molar ratio of 36: 14: 41: 5: 1: 3. It is. The emission spectrum peak of the polymer compound 9 was 525 nm.

Synthesis Example 10 Synthesis of Polymer Compound 10
[Step 1] in the synthesis of the polymer compound 3 is “compound 1c (8.19 mmol), compound 1e (3.32 mmol), compound 2d (9.61 mmol) after setting the reaction vessel in an inert gas atmosphere”, Compound 5 (1.73 mmol), compound 12 (0.52 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (10.5 mg, 0.012 mmol) and toluene (278 ml) are mixed and heated to 105 ° C. did.",
In the synthesis of polymer compound 3 (Step 2), “20% by weight aqueous tetraethylammonium hydroxide solution (40 ml) was added dropwise to the reaction solution and refluxed for 7 hours”.
(Step 3) in the synthesis of macromolecular compound 3 is “after reaction, phenylboronic acid (0.14 g, 1.18 mmol) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (10.5 mg, 0.012 mmol) was added and allowed to reflux for 15 h. "
Except that the reaction was performed in the same manner as in the synthesis of the polymer compound 3, 9.59 g of polymer compound 10 was obtained. The Mn of the polymer compound 10 was 9.4 × 10 ⁴ , and the Mw was 2.5 × 10 ⁵ .
The polymer compound 10 is a theoretical value determined from the amount of the raw materials charged, and the structural unit derived from the compound 1c, the structural unit derived from the compound 1e, the structural unit derived from the compound 2d, and the compound 5 It is a copolymer in which the structural unit derived | led-out and the structural unit derived from the compound 12 are comprised by the molar ratio of 36: 14: 40.5: 7.3: 2.2. The emission spectrum peak of the polymer compound 10 was 614 nm.

Synthesis Example 11 Synthesis of Polymer Compound 11
[Step 1] in the synthesis of the polymer compound 3 is “compound 1c (8.23 mmol), compound 1e (3.34 mmol), compound 2d (9.66 mmol) after setting the reaction vessel in an inert gas atmosphere”, Compound 5 (1.50 mmol), Compound 10 (0.24 mmol), Compound 12 (0.52 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (10.5 mg, 0.012 mmol) and toluene (278 ml) Were mixed and heated to 105 ° C. ",
In the step 1) (step 2) in the synthesis of the polymer compound 3, “20 wt% tetraethylammonium hydroxide aqueous solution (41 ml) was dropped to the reaction solution and refluxed for 8 hours”.
In the synthesis of polymer compound 3 (Step 1) (Step 3), “After reaction, phenylboronic acid (0.15 g, 1.23 mmol) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium ( Add 10.5 mg, 0.012 mmol) and reflux for 14 h. "
Except that the reaction was performed in the same manner as in the synthesis of the polymer compound 3, 9.55 g of the polymer compound 11 was obtained. The Mn of the polymer compound 11 was 1.0 × 10 ⁵ , and the Mw was 2.6 × 10 ⁵ .
The polymer compound 11 is a theoretical unit determined from the amount of the raw materials charged, a constitutional unit derived from the compound 1c, a constitutional unit derived from the compound 1e, a constitutional unit derived from the compound 2d, and the compound 5 The structural unit derived, the structural unit derived from Compound 10, and the structural unit derived from Compound 12 are configured at a molar ratio of 36: 14: 40.5: 6.3: 1: 2.2. It is a copolymer formed. The emission spectrum peak of the polymer compound 11 was 614 nm.

Synthesis Example 12 Synthesis of Polymer Compound 12
[Step 1] in the synthesis of the polymer compound 3 is “compound 1c (8.32 mmol), compound 1e (3.33 mmol), compound 2d (7.30 mmol) after setting the reaction vessel in an inert gas atmosphere”, Compound 5 (1.74 mmol), Compound 9 (2.33 mmol), Compound 12 (0.57 mmol), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (10.5 mg, 0.012 mmol) and toluene (279 ml) Were mixed and heated to 105 ° C. ",
In the synthesis of polymer compound 3 (Step 2), “20% by weight aqueous tetraethylammonium hydroxide solution (40 ml) was added dropwise to the reaction solution and refluxed for 9 hours”.
In the synthesis of polymer compound 3 (Step 3), “After reaction, phenylboronic acid (0.15 g, 1.23 mmol) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (10.5 mg, 0.012 mmol) was added and allowed to reflux for 14 h. "
10.88g of high molecular compounds 12 were obtained by carrying out similarly to the synthesis | combination of the high molecular compounds 3 except setting it as it. The Mn of the polymer compound 12 was 1.2 × 10 ⁵ , and the Mw was 3.5 × 10 ⁵ .
The polymer compound 12 is a theoretical unit determined from the amount of the raw materials charged, a constitutional unit derived from the compound 1c, a constitutional unit derived from the compound 1e, a constitutional unit derived from the compound 2d, and the compound 5 A molar ratio of 36: 14: 30.7: 7.3: 9.8: 2.2: a derived structural unit, a structural unit derived from Compound 9, and a structural unit derived from Compound 12 It is a copolymer composed of The emission spectrum peak of the polymer compound 12 was 614 nm.

Synthesis Example 13 Synthesis of Metal Complex R1
Metal complex R1 (It is a metal complex represented by said formula COM-8.) Which shows red phosphorescence emission was obtained according to the method as described in Unexamined-Japanese-Patent No. 2011-105701. The emission spectrum peak of the metal complex R1 in the xylene solution was 610 nm.

  The emission spectrum peak of the metal complex CR1 represented by the following formula in the xylene solution was 619 nm.

Synthesis Example 14 Synthesis of Compound 13

  Compound 13a (198 g) synthesized according to the method described in JP-A-2006-188673, and a compound synthesized according to the method described in JP-A-2008-231042 after setting the inside of the reaction vessel to a nitrogen gas atmosphere 13b (42.4 g) and diglyme (600 g) were added and heated to 100 ° C. Thereafter, a mixed solution of silver trifluoromethanesulfonate (39.4 g) and ethanol (dehydrated product) (197 g) was added dropwise thereto, and the mixture was stirred at 100 ° C. for 24 hours. Then, it cooled to room temperature, ion-exchange water (6 L) was added, and the precipitated solid was collected by filtration. The obtained solid was washed with methanol, dissolved in toluene, and filtered through a filter covered with celite. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of hexane and toluene), then washed with hexane and dried under reduced pressure at room temperature to obtain compound 13 (9.4 g). The HPLC area percentage value of compound 13 was 99.5% or more.

LC-MS (APCI, positive): m / z = 1564.5 [M + H] ⁺

Synthesis Example 15 Synthesis of Polymer Compound 13
(Synthesis of Polymer Compound 13)
(Step 1) After setting the inside of the reaction vessel to an inert gas atmosphere, compound 1c (0.875 mmol), compound 1e (0.350 mmol), compound 2d (1.013 mmol), compound 5 (0.158 mmol), compound 10 (0.025 mmol), compound 13 (0.055 mmol), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) and toluene (43 mL) were added and heated to 105.degree.
(Step 2) A 20% by weight aqueous tetraethylammonium hydroxide solution (8.3 mL) was added dropwise to the reaction mixture, and the mixture was refluxed for 5 hours.
(Step 3) After the reaction, phenylboronic acid (61.3 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) were added thereto and refluxed for 14.5.
(Step 4) Thereafter, an aqueous solution of sodium diethyldithiacarbamate was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the resulting reaction solution was washed twice with water, twice with a 3 wt% aqueous acetic acid solution, and twice with water, and the resulting solution was added dropwise to methanol, whereby a precipitate formed. The precipitate was dissolved in toluene and purified by sequentially passing through an alumina column and a silica gel column. The obtained solution was added dropwise to methanol and stirred, and then the obtained precipitate was collected by filtration and dried, to obtain 0.90 g of polymer compound 13. The Mn of the polymer compound 13 was 5.2 × 10 ⁴ and the Mw was 1.6 × 10 ⁵ .
The polymer compound 13 is a theoretical unit determined from the amount of the raw materials charged, a constitutional unit derived from the compound 1c, a constitutional unit derived from the compound 1e, a constitutional unit derived from the compound 2d, and the compound 5 The structural unit derived, the structural unit derived from Compound 10, and the structural unit derived from Compound 13 are configured at a molar ratio of 36: 14: 40.5: 6.3: 1: 2.2. It is a copolymer formed. The emission spectrum peak of the polymer compound 13 was 622 nm.

Preparation Example 1: Preparation of Ink IL
The polymer compound 1 was dissolved in a mixed solvent of anisole and cyclohexylbenzene (weight ratio: anisole / cyclohexylbenzene = 1/1) to prepare 0.5 wt% of ink IL.

Preparation Example 2: Preparation of Ink B1
The polymer compound 2 was dissolved in a mixed solvent of anisole and cyclohexylbenzene (weight ratio: anisole / cyclohexylbenzene = 1/1) to prepare a 1.2 wt% ink B1.

Preparation Example 3: Preparation of Ink B2
Polymer compound 6 was dissolved in xylene to prepare 1.2 wt% of ink B2.

Preparation Example 4: Preparation of Ink B3
Polymer compound 5 was dissolved in xylene to prepare 1.2 wt% of ink B3.

Preparation Example 5 Preparation of Ink G1
The polymer compound 3 was dissolved in a mixed solvent of anisole and cyclohexylbenzene (weight ratio: anisole / cyclohexylbenzene = 1/1) to prepare a 1.2 wt% ink G1.

Preparation Example 6: Preparation of Ink G2
Polymer compound 8 was dissolved in xylene to prepare 1.2% by weight of ink G2.

Preparation Example 7 Preparation of Ink G3
Polymer compound 7 was dissolved in xylene to prepare 1.2 wt% of ink G3.

Preparation Example 8 Preparation of Ink G4
Polymer compound 9 was dissolved in xylene to prepare 1.2% by weight of ink G4.

Preparation Example 9 Preparation of Ink R1
A mixture of the polymer compound 4 and the metal complex R1 (weight ratio: polymer compound 4 / metal complex R1 = 92.5 / 7.5) in a mixed solvent of anisole and cyclohexylbenzene (weight ratio: anisole / A solution of 1.2% by weight of ink R1 was prepared by dissolving in cyclohexylbenzene = 1/1).

Preparation Example 10 Preparation of Ink R2
A mixture of the polymer compound 6 and the metal complex R1 (weight ratio: polymer compound 6 / metal complex R1 = 92.5 / 7.5) was dissolved in xylene to prepare 1.2% by weight of the ink R2 .

Preparation Example 11 Preparation of Ink R3
The metal complex R1 was dissolved in xylene to prepare a 0.06 wt% ink R3.

Preparation Example 12 Preparation of Ink R4
Polymer compound 10 was dissolved in xylene to prepare 1.2 wt% of ink R4.

Preparation Example 13 Preparation of Ink R5
Polymer compound 11 was dissolved in xylene to prepare 1.2 wt% of ink R5.

Preparation Example 14 Preparation of Ink R6
Polymer compound 12 was dissolved in a mixed solvent of anisole and cyclohexylbenzene (weight ratio: anisole / cyclohexylbenzene = 1/1) to prepare 1.2 wt% of ink R6.

Preparation Example 15 Preparation of Ink CR1
A mixture of the polymer compound 4 and the metal complex CR1 (weight ratio: polymer compound 4 / metal complex CR1 = 92.5 / 7.5) in a mixed solvent of anisole and cyclohexylbenzene (weight ratio: anisole / A solution of 1.2% by weight of ink CR1 was prepared by dissolving in cyclohexylbenzene (1/1).

Preparation Example 16 Preparation of Ink R7
The polymer compound 13 was dissolved in xylene to prepare 1.2 wt% of ink R7.

Example D1 Production and Evaluation of Light-Emitting Element D1
A spin-coating method using a PEDOT: PSS (AI4081 manufactured by Heraeus), which is a hole injection material of polythiophene sulfonic acid type, as a hole injection material on a glass substrate provided with an ITO film of 45 nm in thickness by sputtering. C. to a thickness of 60 nm, which was heated at 200.degree. C. for 60 minutes on a hot plate in an air atmosphere.
Next, a film was formed to a thickness of 20 nm by spin coating using an ink IL as a hole transport material, and this was heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere.
Next, an ink composition 1 (weight ratio: ink B1 / ink G1 / ink R1 = 86.5 / 7.0 / 6.5) comprising ink B1, ink G1 and ink R1 was prepared. An ink composition 1 was used as the light emitting layer material to form a film with a thickness of 65 nm by spin coating, and this was heated at 130 ° C. for 10 minutes on a hot plate in a nitrogen gas atmosphere.
Thereafter, about 7 nm of sodium fluoride and then about 120 nm of aluminum were vapor-deposited as a cathode to fabricate a light emitting device D1. Note that metal deposition was started after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less.
When a voltage is applied to the light emitting device D1, an emission spectrum peak derived from the polymer compound 2, an emission spectrum peak derived from the polymer compound 3 and an emission spectrum peak derived from the polymer compound ^{2 in} the emission state of 300 cd / m ² (when 5.2 V is applied) An emission spectrum peak derived from the metal complex R1 was observed. The luminous efficiency in the luminous state of 300 cd / m ² was 6.5 cd / A, and the CIE 1931 chromaticity coordinate was (0.32, 0.36).
After setting the current value so that the initial luminance was 2000 cd / m ² , the device was driven by a constant current, and the time change of luminance was measured. The results are shown in Table 1. The time until the luminance reaches 90% of the initial luminance (hereinafter also referred to as LT90) was 10.3 hours.

Examples D2 to D13: Preparation and Evaluation of Light-Emitting Elements D2 to D13
Light-emitting elements D2 to D13 were produced in the same manner as in Example D1 except that ink compositions 2 to 13 shown in Table 1 were respectively prepared and used instead of the ink composition 1 in Example D1. The evaluation results of the light emitting elements D2 to D13 are also shown in Table 1.

Comparative Example CD1 Preparation and Evaluation of Light-Emitting Element CD1
A light emitting element CD1 was produced in the same manner as in Example D1, except that Ink Composition C1 shown in Table 1 was prepared and used in place of Ink Composition 1 in Example D1. The evaluation results of the light emitting element CD1 are also shown in Table 1. The LT90 was 8.6 hours.

Reference Examples BD1, GD1, and RD1: Preparation and Evaluation of Light-Emitting Elements BD1, GD1, and RD1
Light-emitting elements BD1, GD1, and RD1 were produced in the same manner as in Example D2, except that Inks B1, G1, and R1 shown in Table 1 were respectively prepared and used instead of Ink Composition 2 in Example D2. The evaluation results of the light emitting elements BD1, GD1 and RD1 are also shown in Table 1.

Examples D14 to D23: Preparation and Evaluation of Light-Emitting Elements D14 to D23
Light emitting elements D14 to D23 were produced in the same manner as in Example D1 except that ink compositions 14 to 23 shown in Table 2 were respectively prepared and used instead of ink composition 1 in Example D1. The evaluation results of the light emitting elements D14 to D23 are also shown in Table 2.

Example D24 to D28: Preparation and Evaluation of Light-Emitting Elements D24 to D28
Light-emitting elements D24 to D28 were produced in the same manner as in Example D1 except that ink compositions 24 to 28 shown in Table 3 were respectively prepared and used instead of the ink composition 1 in Example D1. The evaluation results of the light emitting elements D24 to D28 are also shown in Table 3.

  From the light emitting elements D1 to D28, it is understood that the emission color of the light emitting element can be adjusted by using the composition of the present invention. Further, the light emitting element D1 and the light emitting element D11 are compared with the light emitting element CD1 (the weight ratio of each ink included in the ink composition used for forming the light emitting layer of the light emitting element D1, the light emitting element D11 and the light emitting element CD1 is the same It can be seen from the above that the luminance life of the light emitting device containing the composition of the present invention is excellent.

Claims (14)

A polymer compound that exhibits blue fluorescence;
A polymer compound that exhibits green fluorescence,
The following formulas (Z-R31), (Z-R32), (Z-R33), (Z-R34), (Z-R35), (Z-R36), (Z-R37), (Z-R38), A metal complex exhibiting red phosphorescence emission represented by (Ir-1), (Ir-2) or (Ir-3) , and / or the following formula (Z-R31), (Z-R32), (Z-) R33), (Z-R34), (Z-R35), (Z-R36), (Z-R37), (Z-R38), (Ir-1), (Ir-2) or (Ir-3) And a polymer compound containing a structural unit having a structure of a metal complex exhibiting red phosphorescence emission represented by

[In the formula,
R ^D5 and R ^D6 each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups have a substituent It is also good. Plural R ^D5 may be the same or different, but at least one R ^D5 has the following formula (Dend-A1), (Dend-A2), (Dend-A3), (Dend-B1), (Dend) It is a group represented by -B2) or (Dend-B3). Plural R ^D6 may be the same or different, but at least one R ^D6 is a group of the following formulas (Dend-A1), (Dend-A2), (Dend-A3), (Dend-B1), (Dend It is a group represented by -B2) or (Dend-B3).
R ^D12 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. Plural R ^D12 may be the same or different.
Dend represents a group represented by the following formula (Dend-A1), (Dend-A2), (Dend-A3), (Dend-B1), (Dend-B2) or (Dend-B3).
Z ^H represents a nitrogen atom or = C (-R ^D6 )-.
-A ^D9 --- A ^D10 - and -A ^D11 --- A ^D12 - independently represent a bidentate ligand of the ^{anionic, A D9, A D10, A} D11 and A ^D12, respectively Independently, it represents a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom.
n _D1 is 1, 2 or 3, n _D2 is 1, 2 or 3, and n _D3 represents 1 or 2. ]

[In the formula,
R ^p1 , R ^p2 and R ^p3 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom. When a plurality of R ^p1 and R ^p2 exist, they may be identical to or different from one another.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. When a plurality of np1 are present, they may be the same or different. ]

[In the formula,
R ^p1 , R ^p2 and R ^p3 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group or a halogen atom. When a plurality of R ^p1 and R ^p2 exist, they may be identical to or different from one another.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. When a plurality of np1 and np2 exist, they may be identical to or different from each other. ] The composition according to claim 1, wherein the polymer compound exhibiting blue fluorescence emission and the polymer compound exhibiting green fluorescence emission include a structural unit represented by the following formula (Y).

[ ^Wherein , Ar ^{Y 1} represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one type of divalent heterocyclic group are directly bonded, Groups may have a substituent. ]   The composition according to claim 2, wherein the polymer compound containing a constituent unit having a structure of a metal complex exhibiting red phosphorescence emission contains a constituent unit represented by the formula (Y). The composition according to claim 2 or 3, wherein the constitutional unit represented by the formula (Y) is a constitutional unit represented by the following formula (Y-2).

[In the formula,
R ^Y1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Plural R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
X ^Y1 represents a group represented by —C (R ^Y2 ) ₂ —, —C (R ^Y2 ) = C (R ^Y2 ) — or —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ —. R ^Y2 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y2 may be the same or different, and R ^Y2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ] The composition according to any one of claims 1 to 4, wherein the polymer compound that exhibits blue fluorescence emission and the polymer compound that exhibits green fluorescence emission include a constitutional unit represented by the following formula (X) .

[In the formula,
Each of a ^X1 and a ^X2 independently represents an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded These groups may have a substituent.
Each of R ^X1 , R ^X2 and R ^X3 independently represents a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]   The composition according to claim 5, wherein the polymer compound containing a constituent unit having a structure of a metal complex exhibiting red phosphorescence emission contains a constituent unit represented by the formula (X). The high molecular compound which shows the said blue fluorescence light emission, and the high molecular compound which shows the said green fluorescence light emission are described in the structural unit represented by following formula (Y-5) or (Y-6). Composition of

[In the formula,
R ^Y1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. Plural R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
R ^Y4 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]   The composition according to claim 7, wherein the polymer compound including a constituent unit having a structure of a metal complex exhibiting red phosphorescence emission includes a constituent unit represented by the formula (Y-5) or (Y-6). object. The composition according to any one of claims 2, 3, 5 and 6, wherein the polymer compound exhibiting green fluorescence emission comprises a constitutional unit represented by the following formula (G).

[Wherein, Ar ^G represents a benzothiadiazole diyl group, a divalent group having a quinoxaline structure, a divalent group in which at least one thienylene group and at least one arylene group are directly bonded, and at least one arylene group] Represents a divalent group to which at least one vinylene group is directly bonded, a divalent group having a perylene structure, or a divalent group represented by the following formula (X-8), these groups each having a substituent You may have. ]

[Wherein, R ^X4 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group or a cyano group, and these groups have a substituent] It is also good. A plurality of R ^X4 may be the same or different. ] The composition as described in any one of Claims 1-9 whose structural unit which has a structure of the metal complex which shows the said red phosphorescence emission is a structural unit represented by following formula (R).

[Wherein, in the formula, Ar ^R represents the above-mentioned formulas (Z-R31), (Z-R32), (Z-R33), (Z-R34), (Z-R35), (Z-R36), (Z-R37 And (Z-R38), (Ir-1), (Ir-2) or (Ir-3) represents a divalent group having a structure of a metal complex that exhibits red phosphorescence. ] The composition as described in any one of Claims 1-9 whose structural unit which has a structure of the metal complex which shows the said red phosphorescence emission is a structural unit represented by following formula (R2).

[Wherein, in the formula, Ar ^R2 is a group represented by the above formulas (Z-R31), (Z-R32), (Z-R33), (Z-R34), (Z-R35), (Z-R36), (Z-R37 Or (Z-R38), (Ir-1), (Ir-2) or (Ir-3) represents a monovalent group having a structure of a metal complex that exhibits red phosphorescence. ] The film according to any one of claims 1 to 11 , further comprising at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant and a solvent. The composition according to one item. A light emitting device comprising the composition according to any one of claims 1 to 11 . An illumination comprising the light emitting device according to claim 13 .

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