JP6314467B2 - 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 composition.

  Organic electroluminescence elements (hereinafter also referred to as “light-emitting elements”) have high luminous efficiency and low driving voltage, and thus can be suitably used for display and lighting applications. Yes. This light-emitting element includes organic layers such as a light-emitting layer and a charge transport layer. For the light emitting layer of the light emitting element, for example, it has been proposed to use a composition containing a light emitting material and a polymer compound containing a fluorene structural unit and an anthracene structural unit shown below (Patent Document 1). . The polymer compound containing the fluorene structural unit and the anthracene structural unit represented by the following corresponds to the polymer compound 1 contained in the composition of the present invention described later. A composition further containing the polymer compound 2 contained in the composition of the present invention is not described.

JP 2012-144722 A

  However, a light emitting device manufactured using the above composition does not necessarily have sufficient luminous efficiency.

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

The present invention firstly
A luminescent material;
A polymer compound 1 containing a constituent chain represented by the following formula (1) in the main chain;
There is provided a composition containing a polymer compound 2 containing a constituent chain represented by the following formula (2) in the main chain.

_{- [- (A) m1 -B-} ] n1 - (1)

[Where:
m1 represents an integer of 1 to 3, and n1 represents an integer of 4 to 10,000. A plurality of m1 may be the same or different.
A represents a divalent group obtained by removing two hydrogen atoms from the structure represented by the following formula (A-101) or (A-102). A plurality of A may be the same or different.
B represents the following formulas (B-101), (B-102), (B-103), (B-104), (B-105), (B-106), (B-107), (B- 108) or (B-109) represents a divalent group obtained by removing two hydrogen atoms. A plurality of B may be the same or different. ]

［式中、
Ｘは、−ＣＲ^Ｘ＝または−Ｎ＝を表す。Ｒ^Ｘは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＸは、同一でも異なっていてもよい。但し、それぞれの６員環に含まれるＸとしての−Ｎ＝の個数は、０、１または２である。
Ｒ^Ｙは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙは、同一でも異なっていてもよく、Ｒ^Ｙ同士は互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｒ^Ｚは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｚは、同一でも異なっていてもよく、Ｒ^Ｚ同士は互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。］

−［−Ｃ−Ｄ−］_ｎ２− （２）

［式中、
ｎ２は、４〜１００００の整数を表す。
Ｃは、下記式（Ｂ−１０１）または（Ｂ−１０２）で表される構造から水素原子を２個除いた２価の基を表す。
Ｄは、下記式（Ｂ−１０１）、（Ｂ−１０２）、（Ｂ−１０３）、（Ｂ−１０４）または（Ｂ−１０５）で表される構造から水素原子を２個除いた２価の基を表す。]

[Where:
X represents -CR ^X = or -N =. R ^X represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of X may be the same or different. However, the number of -N = as X contained in each 6-membered ring is 0, 1 or 2.
R ^Y represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y may be the same or different, and R ^Y may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
R ^Z represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Z may be the same or different, and R ^Z may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

− [− C−D−] _n2 − (2)

[Where:
n2 represents an integer of 4 to 10,000.
C represents a divalent group obtained by removing two hydrogen atoms from the structure represented by the following formula (B-101) or (B-102).
D is a divalent structure obtained by removing two hydrogen atoms from the structure represented by the following formula (B-101), (B-102), (B-103), (B-104) or (B-105). Represents a group. ]

［式中、
Ｘは、−ＣＲ^Ｘ＝または−Ｎ＝を表す。Ｒ^Ｘは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＸは、同一でも異なっていてもよい。但し、それぞれの６員環に含まれるＸとしての−Ｎ＝の個数は、０、１または２である。
Ｒ^Ｙは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙは、同一でも異なっていてもよく、Ｒ^Ｙ同士は互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。］

[Where:
X represents -CR ^X = or -N =. R ^X represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of X may be the same or different. However, the number of -N = as X contained in each 6-membered ring is 0, 1 or 2.
R ^Y represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y may be the same or different, and R ^Y may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

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

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

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

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

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

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

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

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

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

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

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

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

The “alkyl group” may be linear or branched. The carbon atom number of a linear alkyl group is 1-50 normally without including the carbon atom number of a substituent, Preferably it is 3-30, More preferably, it is 4-20. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30 and more preferably 4 to 20 without including the number of carbon atoms of the substituent.
The alkyl group and cycloalkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2 -Ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyl-decyl, dodecyl Cyclohexyl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3 , 5-di-hexylphenyl) propyl group, 6-ethyloxyhexyl group, cyclohexylmethyl group, and cyclohexylethyl group.

“Aryl group” means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the aryl group does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10.
The aryl group may have a substituent, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups Are groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

The “alkoxy group” may be linear or branched. The number of carbon atoms of a linear alkoxy group is 1-40 normally without including the carbon number of a substituent, Preferably it is 4-10. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The alkoxy group and the cycloalkoxy group may have a substituent, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, Examples include a hexyloxy group, a cyclohexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, and a lauryloxy group.

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

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

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

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

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

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

The “alkynyl group” may be linear or branched. The carbon atom number of an alkynyl group is 2-20 normally without including the carbon atom of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The number of carbon atoms of the “cycloalkynyl group” is usually 6-30, preferably 6-20, not including the carbon atoms of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4- Examples include a pentynyl group, a 1-hexenyl group, a 5-hexynyl group, and a group in which these groups have a substituent.

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

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

[Wherein, R and R ^a each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. A plurality of R and R ^a may be the same or different, and R ^a may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

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

［式中、ＲおよびＲ^aは、前記と同じ意味を表す。］

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

  The “crosslinking group” is a group capable of generating a new bond by being subjected to heat treatment, ultraviolet irradiation treatment, radical reaction, etc., and preferably has the formula (B-1), (B-2 ), (B-3), (B-4), (B-5), (B-6), (B-7), (B-8), (B-9), (B-10), A group represented by (B-11), (B-12), (B-13), (B-14), (B-15), (B-16) or (B-17).

［式中、これらの基は置換基を有していてもよい。］

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

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

<Composition>
The composition of the present invention includes a light emitting material, a polymer compound 1 containing a constituent chain represented by formula (1) in the main chain, and a polymer compound containing a constituent chain represented by formula (2) in the main chain. 2 is contained.

[Luminescent material]
The light emitting material is classified into a low molecular light emitting material and a polymer light emitting material. The light emitting material may have a crosslinking group.

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

  Examples of the polymer light emitting material include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a fluorenediyldiyl group, a phenanthrenediyl group, a dihydrophenanthenediyl group, a group represented by the formula (X) described later, and a carbazolediyl group. , A polymer compound containing a phenoxazinediyl group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, and the like.

  The light emitting material contained in the composition of the present invention is preferably a polymer light emitting material.

  The polymer light emitting material is preferably a polymer light emitting material containing a structural unit represented by the following formula (X).

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

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

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

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

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

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

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

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

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

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

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

The divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one divalent heterocyclic group are directly bonded is represented by Ar ^Y1 in the formula (Y) described later. And the same divalent groups as those obtained by directly bonding at least one kind of arylene group and at least one kind of divalent heterocyclic group.

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

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

  The structural unit represented by the formula (X) is preferably a structural unit represented by the following formula (XX).

［式中、
Ａｒ^X1、Ａｒ^X2およびＡｒ^X3は、前記と同じ意味を表す。
Ａｒ^X4は、アリール基または１価の複素環基の基を表し、これらの基は置換基を有していてもよい。複数存在するＡｒ^X4は、同一でも異なっていてもよい。］

[Where:
Ar ^X1 , Ar ^X2 and Ar ^X3 have the same meaning as described above.
Ar ^X4 represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of Ar ^X4 may be the same or different. ]

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

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

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

  The structural unit represented by the formula (X) is preferably 0.1 to 30 mol% with respect to the total amount of the structural units contained in the polymer light emitting material because the hole transport property of the polymer light emitting material is excellent. More preferably, it is 1-15 mol%, More preferably, it is 1-10 mol%.

  Examples of the structural unit represented by the formula (X) include structural units represented by the formulas (X1-1) to (X1-17), preferably the formulas (X1-3) to (X1-10). ).

  In the polymer light emitting material, the structural unit represented by the formula (X) may be included alone or in combination of two or more.

  The polymer light emitting material preferably further includes a structural unit represented by the following formula (Y).

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

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

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

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

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

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

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

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

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

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

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-1) to (Y-10), and the luminance lifetime of the light emitting device using the composition of the present invention. In view of the above, it is preferably a structural unit represented by the formula (Y-1), (Y-2) or (Y-3), more preferably in the formula (Y-1) or (Y-2). From the viewpoint of the electron transport property of the polymer light-emitting material, it is preferably a structural unit represented by the formulas (Y-4) to (Y-7). From the viewpoint of pore transportability, structural units represented by formulas (Y-8) to (Y-10) are preferred.

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

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

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

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

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

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

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

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

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

［式中、Ｒ^Y2は前記と同じ意味を表す。］

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

［式中、Ｒ^Y1およびＸ^Y1は前記と同じ意味を表す。］

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

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

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

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

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

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

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

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

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, is excellent in the luminance life of a light-emitting element using the composition of the present invention. Preferably it is 0.5-80 mol% with respect to the total amount of a unit, More preferably, it is 30-60 mol%.

A structural unit represented by formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group directly bonded to each other. Is preferably 0.5 to 30 mol%, more preferably 3%, based on the total amount of the structural units contained in the polymer light-emitting material, since the charge transporting property of the polymer light-emitting material is excellent. ~ 20 mol%.

  One type of structural unit represented by the formula (Y) may be contained in the polymer light emitting material, or two or more types may be contained.

  Examples of the polymer light-emitting material include polymer light-emitting materials P-1 to P-7 shown in Table 1 below. Here, the “other” structural unit means a structural unit other than the structural unit represented by the formula (X) and the structural unit represented by the formula (Y).

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

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

[Polymer Compound 1]
The high molecular compound 1 contains the structural chain represented by Formula (1) in a principal chain. The polymer compound 1 includes a structural unit other than the structural chain represented by the formula (1) (for example, the structural unit represented by the formula (X) and the structural unit represented by the formula (Y)) in the main chain. However, it is preferably composed of a structural chain represented by the formula (1) and a structural unit represented by the formula (Y), and is composed only of the structural chain represented by the formula (1). More preferably.

_{- [- (A) m1 -B-} ] n1 - (1)

[Where:
m1 represents an integer of 1 to 3, and n1 represents an integer of 4 to 10,000. A plurality of m1 may be the same or different.
A represents a divalent group obtained by removing two hydrogen atoms from the structure represented by the above formula (A-101) or (A-102). A plurality of A may be the same or different.
B represents the above formulas (B-101), (B-102), (B-103), (B-104), (B-105), (B-106), (B-107), (B- 108) or (B-109) represents a divalent group obtained by removing two hydrogen atoms. A plurality of B may be the same or different. ]

  m1 is preferably 1 or 2, and more preferably 1. A plurality of m1 may be the same or different, but all m1 are preferably 1 or 2, and more preferably 1.

  n1 is preferably an integer of 8 to 10000, more preferably an integer of 30 to 10000, and particularly preferably an integer of 50 to 5000.

X in formulas (A-101), (A-102), and (B-101) to (B109) is preferably -CR ^X =. R ^X in —CR ^X ═ is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group. More preferred is a hydrogen atom, an alkyl group or a cycloalkyl group.

R ^Y in formulas (B-104), (B-105), (B-106) and (B-108) is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. And more preferably an alkyl group, a cycloalkyl group, or an aryl group.

R ^Z in formula (B-109) is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and is a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group. More preferred is a hydrogen atom, an alkyl group or a cycloalkyl group.

In the formulas (B-104), (B-106), and (B-108), one of two R ^Y is an alkyl group or a cycloalkyl group, and the other is an aryl group or a monovalent heterocyclic group. Preferably, one is an alkyl group or a cycloalkyl group, more preferably the other is an aryl group, and one is an alkyl group, and the other is more preferably an aryl group.

Further, the four R ^Y in formula (B-105) are preferably an alkyl group or a cycloalkyl group, and more preferably an alkyl group. When four R ^Y in the formula (B-105) is an alkyl group, two R ^Y selected from the four R ^Y are bonded to each other to form a ring together with the carbon atom to which each R ^Y is bonded. More preferably, two R ^Y selected from four R ^Y are bonded to each other, and the remaining two R ^Y are also bonded to each other to form a ring together with the carbon atoms to which they are bonded.

  The divalent group represented by A is preferably a divalent group represented by the formula (A-103), (A-104), (A-105) or (A-106). It is more preferably a divalent group represented by (A-103) or (A-105).

［式中、Ｒ^Ｘは、前記と同じ意味を表す。］

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

  Examples of the divalent group represented by A include divalent groups represented by formula (A-107) to formula (A-117).

  The divalent group represented by B is represented by formulas (B-110), (B-111), (B-112), (B-113), (B-114), (B-115), (B -116), (B-117), (B-118), (B-119), (B-120), (B-121), (B-122) or 2 represented by (B-123) It is preferably a valent group, and more preferably a divalent group represented by the formula (B-112), (B-116), (B-118), or (B-122).

［式中、Ｒ^Ｘ、Ｒ^ＹおよびＲ^Ｚは、前記と同じ意味を表す。］

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

  Examples of the divalent group represented by B include divalent groups represented by formula (B-124) to formula (B-145).

  In the high molecular compound 1, only 1 type of the structural chain represented by Formula (1) may be included, or 2 or more types may be included. When two or more types of constituent chains represented by the formula (1) are included, it is preferable that the constituent chains represented by the formula (1) are combined to form a chain.

[Polymer Compound 2]
The high molecular compound 2 contains the structural chain represented by Formula (2) in a principal chain. The polymer compound 2 includes a structural unit other than the structural chain represented by the formula (2) (for example, the structural unit represented by the formula (X) and the structural unit represented by the formula (Y)) in the main chain. However, it is preferably composed of a structural chain represented by the formula (2) and a structural unit represented by the formula (Y), and is composed only of the structural chain represented by the formula (2). More preferably.

− [− C−D−] _n2 − (2)

[Where:
n2 represents an integer of 4 to 10,000.
C represents a divalent group obtained by removing two hydrogen atoms from the structure represented by the formula (B-101) or (B-102).
D is a divalent form obtained by removing two hydrogen atoms from the structure represented by the formula (B-101), (B-102), (B-103), (B-104) or (B-105). Represents a group. ]

  n2 is preferably an integer of 8 to 10000, more preferably an integer of 30 to 10000, and particularly preferably an integer of 50 to 5000.

Formula (B-101) X in ~ (B-105), examples and preferred ranges of -CR ^X = and ^{R Y} is represented by X has the formula (B-101) described above for the polymer compound 1 ~ (B -105) are the same as the examples and preferred ranges of X, X represented by X, -CR ^X = and ^RY .

  The divalent group represented by C is preferably a divalent group represented by the formula (B-110) or (B-112).

［式中、Ｒ^Ｘは、前記と同じ意味を表す。］

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

  Examples of the divalent group represented by C include divalent groups represented by formula (C-101) to formula (C-106).

  The divalent group represented by D is preferably a divalent group represented by the formula (B-112) or (B-118).

［式中、Ｒ^ＸおよびＲ^Ｙは、前記と同じ意味を表す。］

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

  Examples of the divalent group represented by D include divalent groups represented by formula (D-101) to formula (D-105).

  In the high molecular compound 2, only 1 type of the structural chain represented by Formula (2) may be contained, or 2 or more types may be contained. When two or more types of constituent chains represented by the formula (2) are included, it is preferable that the constituent chains represented by the formula (2) are bonded to form a chain.

[Production Method of Polymer Light-Emitting Material, Polymer Compound 1 and Polymer Compound 2>
The polymer light-emitting material, polymer compound 1 and polymer compound 2 contained in the composition of the present invention are described in Chemical Review (Chem. Rev.), Vol. 109, pages 897-1091 (2009), respectively. Examples thereof include a method of polymerizing by a coupling reaction using a transition metal catalyst such as a Suzuki reaction, a Yamamoto reaction, a Buchwald reaction, a Stille reaction, a Negishi reaction, and a Kumada reaction. It is done.

  In the above polymerization method, as a method for charging the monomer, a method in which the entire amount of the monomer is charged all at once into the reaction system, a part of the monomer is charged and reacted, and then the remaining monomer is batched. , A method of charging continuously or dividedly, a method of charging monomer continuously or dividedly, and the like.

  Although it does not specifically limit as a transition metal catalyst, A palladium catalyst and a nickel catalyst are mentioned.

  Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination. When the purity of the polymer light-emitting material, polymer compound 1 and polymer compound 2 is low, it can be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, etc. .

  In Examples of the present specification, as an example of a method for producing the polymer light-emitting material, polymer compound 1 and polymer compound 2 contained in the composition of the present invention, a polymerization method utilizing a Suzuki coupling reaction using a palladium catalyst Indicates.

[Composition ratio]
Since the light-emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention are more excellent in the light-emitting efficiency of the light-emitting device obtained using the composition of the present invention, the light-emitting material is adjusted to 100 parts by mass. On the other hand, it is preferable that the polymer compound 1 is contained in an amount of 0.1 to 50 parts by mass and the polymer compound 2 is contained in an amount of 0.1 to 50 parts by mass. It is more preferable that 1-30 mass parts and 1-30 mass parts of high molecular compounds 2 are contained, 3-20 mass parts of high molecular compounds 1 with respect to 100 mass parts of luminescent materials, and high molecular compound More preferably, 3 to 20 parts by mass of 2 is contained.

[Other ingredients]
The composition of the present invention contains a light-emitting material, a polymer compound 1, and a polymer compound 2, and includes a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant, and a solvent. It may contain at least one material selected from the group consisting of:

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

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

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

  In the ink, the amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 100 parts by weight based on the total of 100 parts by weight of the luminescent material, polymer compound 1 and polymer compound 2 contained in the composition of the present invention. Is 2000 to 20000 parts by weight.

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

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

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

  In the composition of the present invention, the amount of the hole transport material is usually 1 to 100 parts by weight with respect to a total of 100 parts by weight of the light-emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention. 400 parts by weight, preferably 5 to 150 parts by weight.

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

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

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

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

  In the composition of the present invention, the compounding amount of the electron transport material is usually 1 to 400 with respect to a total of 100 parts by weight of the light emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention. Parts by weight, preferably 5 to 150 parts by weight.

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

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

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

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

  In the composition of the present invention, the compounding amounts of the hole injection material and the electron injection material are respectively 100 parts by weight in total of the light emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention. The amount is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight.

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

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

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

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

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the luminescent material, polymer compound 1 and polymer compound 2 contained in the composition of the present invention and does not inhibit luminescence and charge transport. Examples thereof include phenolic antioxidants and phosphorus antioxidants.

  In the composition of the present invention, the blending amount of the antioxidant is usually 0.001 to 10 with respect to 100 parts by weight in total of the light emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention. Parts by weight.

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

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

  The film includes an insolubilized film obtained by insolubilizing the light-emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention with respect to a solvent by crosslinking. The insolubilized film is a film obtained by crosslinking the composition of the present invention by an external stimulus such as heating or light irradiation. Since the insolubilized film is substantially insoluble in a solvent, the insolubilized film can be suitably used for stacking light emitting elements.

  The heating temperature for crosslinking the film is usually 25 to 300 ° C, preferably 50 to 250 ° C, more preferably 150 to 200 ° C.

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

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

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

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

<Light emitting element>
The light emitting device of the present invention is a light emitting device obtained by using the composition of the present invention, and the light emitting material, the polymer compound 1 and the polymer compound 2 contained in the composition of the present invention are intermolecular or intermolecular. It may be cross-linked.
As a structure of the light emitting element of this invention, it has an electrode which consists of an anode and a cathode, and a layer obtained using the composition of this invention provided between this electrode, for example.

[Layer structure]
The layer obtained using the composition of the present invention is usually a light emitting layer. In addition to the light emitting layer, the light emitting device of the present invention may have at least one layer selected from the group consisting of a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer. The light emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, and the electron injection layer are the above-described compositions, hole transport materials, hole injection materials, electron transport materials, and electron injection materials, respectively. The ink can be prepared by using the same method as that of the above-described film.

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

  Examples of the material of the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer include the above-described hole transport material, electron transport material, hole injection material, and electron injection material.

  The material for the hole transport layer, the material for the electron transport layer, and the material for the light emitting layer (usually the composition of the present invention) are adjacent to the hole transport layer, the electron transport layer, and the light emitting layer, respectively, in the production of the light emitting device. When dissolved in the solvent used during the formation of the layer, the material preferably has a crosslinking group in order to avoid dissolution of the material in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

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

  The order, number, and thickness of the layers to be stacked may be adjusted in consideration of the driving voltage of the light emitting element and the element life.

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

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

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

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

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

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

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

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

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

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

  Polymer monomer HP-1, polymer light emitting materials EP-1 and EP-2, polymer compound 1P-1, and monomers CM1 to CM16 used in the synthesis of polymer compounds 2P-1 to 2P-3 The structure is shown below.

Monomer CM1 was synthesized according to the synthesis method described in JP2011-174062.
Monomer CM2 was synthesized by the method described in WO 2005/049546.
As the monomer CM3, a commercially available compound was used.
Monomer CM4 was synthesized according to the synthesis method described in JP-A-2008-106241.
Monomer CM5 was synthesized according to the synthesis method described in JP2011-174062.
Monomer CM6 was synthesized according to the synthesis method described in JP2012-144722A.
Monomer CM7 was synthesized according to the synthesis method described in JP2012-144722A.
Monomer CM8 was synthesized according to the synthesis method described in JP-A No. 2004-143419.
Monomer CM9 was synthesized according to the synthesis method described in JP2010-031259A.
As the monomer CM10, a commercially available compound was used.
Monomer CM11 was synthesized according to the synthesis method described in JP2012-144722A.
Monomer CM12 was synthesized according to the synthesis method described in JP 2010-189630 A.
Monomer CM13 was synthesized according to the synthesis method described in JP2012-214732A.
Monomer CM14 was synthesized according to the synthesis method described in JP2012-214732A.
Monomer CM15 was synthesized according to the synthesis method described in JP2012-236970A.
Monomer CM16 was synthesized according to the following method.

  <Synthesis Example 1> Synthesis of Monomer CM16

(First step)
The reaction vessel was filled with a nitrogen gas atmosphere, and tetrahydrofuran (commercially dehydrated product, 600 mL), magnesium (168.2 g, 6.92 mol) and iodine (0.7 g, 2.7 mmol) were added. Thereafter, the temperature was raised to 45 ° C., n-hexyl bromide (224 g, 1.36 mol) was added dropwise, then tetrahydrofuran (commercially dehydrated product, 880 mL) was added, and then n-hexyl bromide (895 g, 5.42 mol). Was diluted with tetrahydrofuran (commercially dehydrated product, 1.82 L) dropwise over 3 hours. Then, it stirred at 50 degreeC for 2 hours. Then, at 50 ° C., [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride (NiCl ₂ (dppp), 29.4 g, 54.2 mmol) was added, and then compound CM16a (343. 5 g, 2.71 mol) was added dropwise. Then, it stirred at 65 degreeC for 5 hours. Tetrahydrofuran (commercially dehydrated product, 5.5 L) was added to the resulting reaction solution, and then cooled to room temperature. The obtained reaction solution was added dropwise to hydrochloric acid (2 mol / L, 3.4 L) cooled to 7 ° C., and then the organic layer was extracted with toluene. The obtained organic layer was washed with water, and then the solvent was distilled off under reduced pressure to obtain the target compound CM16b (425 g) as a yellow oil. The yield was 82%. The HPLC area percentage value of the obtained compound CM16b was 92.7%.

LC / MS (APPI, positive): [M ⁺ ] 176

(Second step)
The reaction vessel was filled with a nitrogen gas atmosphere, and then compound CM16b (424.4 g, 2.23 mmol), dichloromethane (1.7 L) and iodine (56.6 g, 223 mmol) were added. Then, it cooled to 3 degreeC and bromine (908.7g, 5.69mol) was dripped over 2 hours. Thereafter, the mixture was stirred at 5 ° C for 1 hour, and then an aqueous sodium hydroxide solution (10 wt%) was added dropwise. Thereafter, the organic layer was extracted using ion-exchanged water and dichloromethane. The obtained organic layer was concentrated under reduced pressure, toluene and activated carbon were added, and the mixture was stirred for 1 hour and filtered. The obtained filtrate was concentrated under reduced pressure to obtain the target compound CM16c (745.7 g) as a yellow oil. The yield was 87%. The HPLC area percentage value of the obtained compound CM16c was 86.6%.

LC-MS (APPI, positive): [M ⁺ ] 332

(Third process)
After making the inside of the reaction vessel an argon gas atmosphere, compound CM16c (744.5 g, 1.93 mol), 1,2-dimethoxyethane (6.2 L), potassium acetate (1136 g, 11.6 mol) and bis (pinacolato) diboron (1120 g, 4.44 mol) was added. Then, [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (PdCl ₂ (dppf) · CH ₂ Cl ₂ , 47.3 g, 57.9 mmol) was added thereto, Stir at 85 ° C. for 24 hours. Then, it cooled to room temperature and extracted the organic layer using toluene and water. The solvent contained in the obtained organic layer was distilled off under reduced pressure. Toluene and activated carbon were added to the resulting residue, stirred for 1 hour, and filtered. The obtained filtrate was washed with an aqueous sodium chloride solution and water, and then concentrated under reduced pressure. Thereafter, methanol was added thereto, and the precipitated solid was collected by filtration and dried. Isopropanol was added to the obtained solid, dissolved by heating, and then cooled. The precipitated solid was collected by filtration and dried to obtain the target monomer CM16 (709 g) as a white powder solid. The yield was 86%. The HPLC area percentage value of the obtained monomer CM16 was 99.5% or more.

¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 7.53 (s, 2H), 2.81 (t, 2H), 2.48 (s, 3H), 1.55-1.29 (M, 34H), 0.88 (t, 3H).
LC-MS (APPI, positive): [M ⁺ ] 428

<Synthesis Example 2> Synthesis of Polymer Compound HP-1 Polymer compound HP-1 was synthesized according to the synthesis method described in JP 2012-144722 A using monomers shown in the following table. The polymer compound HP-1 is a copolymer in which the structural units derived from the respective monomers are configured in the molar ratio shown in Table 2 below, according to the theoretical values obtained from the charged raw materials.

<Synthesis Example 3> Synthesis of Polymer Light-Emitting Material EP-1 Polymer light-emitting material EP-1 was synthesized according to the synthesis method described in JP 2012-144722 A using monomers shown in the following table. The polymer light-emitting material EP-1 is a copolymer in which the structural units derived from the respective monomers are configured in the molar ratio shown in Table 3 below, according to the theoretical values obtained from the charged raw materials.

<Synthesis Example 4> Synthesis of Polymer Light-Emitting Material EP-2 Polymer light-emitting material EP-2 was synthesized according to the synthesis method described in JP2012-214732A using monomers shown in the following table. The polymer light-emitting material EP-2 is a copolymer in which the structural units derived from the respective monomers are configured in the molar ratio shown in Table 4 below, according to the theoretical values obtained from the charged raw materials.

<Synthesis Example 5> Synthesis of Polymer Compound 1P-1 Polymer compound 1P-1 was synthesized according to a synthesis method described in JP 2012-144722 A using monomers shown in the following table. The polymer compound 1P-1 is an alternating copolymer in which the structural units derived from the respective monomers are composed of the molar ratios shown in Table 5 below, according to the theoretical values determined from the charged raw materials.

<Synthesis Example 6> Synthesis of polymer compound 2P-1 Polymer compound 2P-1 was synthesized according to the synthesis method described in JP 2012-214732 A using monomers shown in the following table. 2P-1 is an alternating copolymer in which the structural units derived from the respective monomers are composed of the molar ratios shown in Table 6 below according to the theoretical values determined from the charged raw materials.

<Synthesis Example 7> Synthesis of polymer compound 2P-2
(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, CM16 (2.96 mmol), CM14 (3.00 mmol), dichlorobis (tris-o-methoxyphenylphosphine) palladium (2.7 mg) and toluene (40 mL) were added. And heated to 105 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (10 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 4.5 hours.
(Step 3) After the reaction, phenylboronic acid (36.8 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (2.7 mg) were added thereto and refluxed for 16.0 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred. The precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.00 g of polymer compound 2P-2. The high molecular compound 2P-2 had Mn of 8.9 × 10 ⁴ and Mw of 3.3 × 10 ⁵ .
The polymer compound 2P-2 is an alternating copolymer in which the structural units derived from the respective monomers are composed of the molar ratio shown in Table 7 below, according to the theoretical values obtained from the amount of the raw materials charged. is there.

<Synthesis Example 8> Synthesis of polymer compound 2P-3
(Step 1) After making the inside of the reaction vessel an inert gas atmosphere, CM12 (1.94 mmol), CM15 (2.00 mmol), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.8 mg) and toluene (40 mL) were added. And heated to 105 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (7 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 6.5 hours.
(Step 3) After the reaction, phenylboronic acid (24.5 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.8 mg) were added thereto and refluxed for 13.8 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the reaction solution was washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and when the resulting solution was added dropwise to methanol, precipitation occurred. The precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.12 g of polymer compound 2P-3. The high molecular compound 2P-3 had Mn of 4.0 × 10 ⁴ and Mw of 1.2 × 10 ⁵ .
The polymer compound 2P-3 is an alternating copolymer in which the structural units derived from the respective monomers are composed of the molar ratios shown in Table 8 below, according to the theoretical values determined from the amounts of the raw materials charged. is there.

<Example D11>
AQ-1200 (manufactured by Plectronics), a polythiophene / sulfonic acid-based hole injecting agent, is applied to a glass substrate on which an ITO film having a thickness of 45 nm is formed by sputtering. A film having a thickness of 35 nm was formed, and this was heated in an air atmosphere at 170 ° C. for 15 minutes on a hot plate to form a hole injection layer.

  Next, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method using a xylene solution (0.6 wt%) of the polymer compound HP-1, and this was formed in a nitrogen gas atmosphere. The hole transport layer was formed by heating on a hot plate at 180 ° C. for 60 minutes.

  Next, a xylene solution (1.2 wt%) of the polymer light-emitting material EP-1, a xylene solution (1.2 wt%) of the polymer compound 1P-1, and a xylene solution of the polymer compound 2P-1 ( 1.2% by weight) was adjusted. And each xylene solution was mixed so that solid content ratio of the high molecular compound EP-1, the high molecular compound 1P-1, and the high molecular compound 2P-1 might be set to 90: 2.5: 7.5. Using this xylene solution, a film having a thickness of 60 nm was formed on the hole transport layer by spin coating, and this was heated on a hot plate at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. A light emitting layer was formed.

Next, about 7 nm of sodium fluoride and then about 120 nm of aluminum were deposited as a cathode on the light emitting layer. After vapor deposition, the light emitting element D11 was produced by sealing using a glass substrate. The metal deposition was started after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less.

When voltage was applied to the light emitting device D11, EL light emission having a peak at 460 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 9.2 cd / A. The results are shown in Table 9.

<Example D12>
Example D11 except that a xylene solution mixed so that the solid content ratio of the polymer light-emitting material EP-1, polymer compound 1P-1 and polymer compound 2P-1 was 80: 5: 15 was used. Similarly, a light-emitting element D12 was manufactured.

When voltage was applied to the light emitting device D12, EL light emission having a peak at 460 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 9.1 cd / A. The results are shown in Table 9.

<Comparative Example CD11>
A light emitting device CD11 was produced in the same manner as in Example D11 except that the xylene solution of the polymer light emitting material EP-1 alone was used.

When voltage was applied to the light emitting device CD11, EL light emission having a peak at 460 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 7.6 cd / A. The results are shown in Table 9.

<Comparative Example CD12>
A light emitting device CD12 was produced in the same manner as in Example D11 except that a xylene solution mixed so that the solid content ratio of the polymer light emitting material EP-1 and the polymer compound 1P-1 was 90:10 was used. did.

When voltage was applied to the light emitting device CD12, EL light emission having a peak at 460 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 8.6 cd / A. The results are shown in Table 9.

<Example D21>
Except for using a xylene solution mixed such that the solid content ratio of the polymer light-emitting material EP-2, polymer compound 1P-1 and polymer compound 2P-1 is 90: 2.5: 7.5, A light emitting device D21 was produced in the same manner as in Example D11.

When voltage was applied to the light emitting device D21, EL light emission having a peak at 455 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 9.6 cd / A. The results are shown in Table 10.

<Example D22>
Except for using a xylene solution mixed so that the solid content ratio of the polymer light-emitting material EP-2, polymer compound 1P-1 and polymer compound 2P-2 was 90: 2.5: 7.5, A light emitting device D22 was produced in the same manner as in Example D11.

When voltage was applied to the light emitting device D22, EL light emission having a peak at 455 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 9.9 cd / A. The results are shown in Table 10.

<Example D23>
Except for using a xylene solution mixed so that the solid content ratio of the polymer light emitting material EP-2, the polymer compound 1P-1 and the polymer compound 2P-3 is 90: 2.5: 7.5, A light emitting device D23 was produced in the same manner as Example D11.

When voltage was applied to the light emitting device D23, EL light emission having a peak at 455 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 9.6 cd / A. The results are shown in Table 10.

<Comparative Example CD21>
A light emitting device CD21 was produced in the same manner as in Example D11 except that a xylene solution mixed so that the solid content ratio of the polymer light emitting material EP-2 and the polymer compound 1P-1 was 90:10 was used. did.

When voltage was applied to the light emitting device CD21, EL light emission having a peak at 455 nm was observed. The efficiency at a luminance of 1000 cd / m ² was 9.1 cd / A. The results are shown in Table 10.

  From these results, it can be seen that the light-emitting element using the composition of the present invention is excellent in luminous efficiency.

Claims (3)

A polymer light-emitting material comprising a structural unit represented by the following formula (XX) and a structural unit represented by the following formula (Y-1) or the following formula (Y-2) ;
Polymer compound 1 containing a structural chain represented by the following formula (1) in the main chain (however, the structural unit represented by the formula (XX) and the structural chain represented by the following formula (2) are used as the main chain. Not included) and
Polymer compound 2 containing a structural chain represented by the following formula (2) in the main chain (however, the structural unit represented by the formula (XX) and the structural chain represented by the formula (1) includes not) and a composition containing,
The composition comprising 3 to 20 parts by mass of the polymer compound 1 and 3 to 20 parts by mass of the polymer compound 2 with respect to 100 parts by mass of the polymer light emitting material .


_{- [- (A) m1 -B-} ] n1 - (1)

[Where:
m1 represents an integer of 1 to 3, and n1 represents an integer of 4 to 10,000. A plurality of m1 may be the same or different.
A represents a divalent group represented by the following formula (A-103), (A-104), (A-105) or (A-106) . A plurality of A may be the same or different.
B represents a divalent group represented by the following formula (B-112), (B-116), (B-118) or (B-122) . A plurality of B may be the same or different. ]

− [− C−D−] _n2 − (2)

[Where:
n2 represents an integer of 4 to 10,000.
C represents a divalent group represented by the following formula (B-110) or (B-112) .
D represents a divalent group represented by the following formula (B-112) or (B-118) . ]

[Where:
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^X2 each independently represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, This group may have a substituent.
Ar ^X4 represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of Ar ^X4 may be the same or different. ]

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

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

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

[Wherein R ^X represents the same meaning as described above.
R ^Y represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
A plurality of R ^Y may be the same or different, and R ^Y may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
R ^Z represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.
A plurality of R ^Z may be the same or different, and R ^Z may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ] The composition according to claim 1, 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, an antioxidant, and a solvent. Emitting device obtained using the composition of claim 1 or 2.