JP6979400B2 - Light emitting element - Google Patents

Description

The present invention relates to a light emitting device.

Light emitting devices such as organic electroluminescence devices can be suitably used for displays and lighting applications, and research and development are being carried out.

For example, Patent Document 1 describes an organic layer containing a polymer compound (P0-1) containing a structural unit represented by the following formula (M0-1) and light emission represented by the following formula (EM0-1). A light emitting device having a light emitting layer containing a material is described. The polymer compound (P0-1) is a polymer compound having no cross-linking group.

For example, Patent Document 2 describes an organic layer containing a crosslinked polymer compound (P0-2) represented by the following formula and a light emitting layer containing a light emitting material represented by the following formula (EM0-2). A light emitting element having the above is described. The polymer compound (P0-2) contains a cross-linking structural unit having a group represented by the formula (XL-A) described later and a cross-linking structural unit having a group represented by the formula (XL-B). Different from high molecular weight compounds.

International Publication No. 2007-100010 Japanese Unexamined Patent Publication No. 2010-183010

As the light emitting element, an element having a sufficiently low drive voltage is required. Therefore, an object of the present invention is to provide a light emitting element having a low drive voltage.

The present invention provides the following [1] to [15].

［式中、
ｎ^１Ｂは、０〜１５の整数を表す。
Ａｒ^１Ｂは、芳香族炭化水素基又は芳香族複素環基を表す。
Ｒ^１Ｂは、ハロゲン原子、シアノ基、アルキル基、シクロアルキル基、アリール基、１価の複素環基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、アルケニル基、シクロアルケニル基、アルキニル基又はシクロアルキニル基を表し、これらの基は置換基を有していてもよい。Ｒ^１Ｂが複数存在する場合、同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。］

［式中、
ｎＡ及びｎＢは、それぞれ独立に、０〜５の整数を表す。
Ｌ^Ａ及びＬ^Ｂは、それぞれ独立に、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^Ａ及びＬ^Ｂ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。
Ｘ^Ａ及びＸ^Ｂは、それぞれ独立に、架橋基を表す。］
［２］前記Ｘ^Ａ又は前記Ｘ^Ｂが、架橋基Ａ群から選ばれる少なくとも１種の架橋基である、［１］に記載の発光素子。

［式中、Ｒ^ＸＬは、メチレン基、酸素原子又は硫黄原子を表し、ｎ^ＸＬは、０〜５の整数を表す。Ｒ^ＸＬが複数存在する場合、それらは同一でも異なっていてもよく、ｎ^ＸＬが複数存在する場合、それらは同一でも異なっていてもよい。＊１は結合位置を表す。これらの架橋基は置換基を有していてもよい。］
［３］前記式（ＸＬ−Ａ）で表される基を有する架橋構成単位が、式（ＸＬ−Ａ１）で表される構成単位又は式（ＸＬ−Ａ２）で表される構成単位である、［１］又は［２］に記載の発光素子。

［式中、
ｎ^Ａ１は、１〜４の整数を表す。ｎ^Ａ１が複数存在する場合、それらは同一でも異なっていてもよい。
ｎ^Ａ２は、０又は１の整数を表す。
Ｘ^ＬＡは、前記式（ＸＬ−Ａ）で表される架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｘ^ＬＡが複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも１つのＸ^ＬＡは、前記式（ＸＬ−Ａ）で表される架橋基である。
Ａｒ^Ａ３は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^Ａ５は、芳香族炭化水素基、複素環基、又は、少なくとも１種の芳香族炭化水素環と少なくとも１種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ａｒ^Ａ４及びＡｒ^Ａ６は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^Ａ４、Ａｒ^Ａ５及びＡｒ^Ａ６はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接又は酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。］
［４］前記式（ＸＬ−Ｂ）で表される基を有する架橋構成単位が、式（ＸＬ−Ｂ１）で表される構成単位又は式（ＸＬ−Ｂ２）で表される構成単位である、［１］又は［２］に記載の発光素子。

［式中、
ｎ^Ｂ１は、１〜４の整数を表す。ｎ^Ｂ１が複数存在する場合、それらは同一でも異なっていてもよい。
ｎ^Ｂ２は、０又は１の整数を表す。
Ｘ^ＬＢは、前記式（ＸＬ−Ｂ）で表される架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｘ^ＬＢが複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも１つのＸ^ＬＢは、前記式（ＸＬ−Ｂ）で表される架橋基である。
Ａｒ^Ｂ３は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^Ｂ５は、芳香族炭化水素基、複素環基、又は、少なくとも１種の芳香族炭化水素環と少なくとも１種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ａｒ^Ｂ４及びＡｒ^Ｂ６は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^Ｂ４、Ａｒ^Ｂ５及びＡｒ^Ｂ６はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接又は酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。］
［５］前記Ｘ^Ａが、前記架橋基Ａ群から選ばれる式（ＸＬ−３）、式（ＸＬ−４）、式（ＸＬ−１３）又は式（ＸＬ−１７）で表される架橋基である、［２］〜［４］のいずれかに記載の発光素子。
［６］前記Ｘ^Ｂが、前記架橋基Ａ群から選ばれる式（ＸＬ−１）、式（ＸＬ−２）、式（ＸＬ−５）、式（ＸＬ−６）、式（ＸＬ−７）、式（ＸＬ−８）、式（ＸＬ−１４）、式（ＸＬ−１５）又は式（ＸＬ−１６）で表される架橋基である、［２］〜［５］のいずれかに記載の発光素子。
［７］前記Ａｒ^１Ｂが、芳香族炭化水素基である、［１］〜［６］のいずれかに記載の発光素子。
［８］前記Ａｒ^１Ｂが、ベンゼン環、ビフェニル環、ナフタレン環、アントラセン環、フェナントレン環、ジヒドロフェナントレン環、トリフェニレン環、ナフタセン環、フルオレン環、スピロビフルオレン環、ピレン環、ペリレン環、クリセン環、インデン環、フルオランテン環、ベンゾフルオランテン環又はアセナフトフルオランテン環から、環を構成する炭素原子に直接結合する水素原子１個以上を除いてなる基である、［７］に記載の発光素子。
［９］前記Ａｒ^１Ｂが、ビフェニル環、フルオレン環、ピレン環、フルオランテン環、ベンゾフルオランテン環又はアセナフトフルオランテン環から、環を構成する炭素原子に直接結合する水素原子１個以上を除いてなる基である、［８］に記載の発光素子。
［１０］前記ｎ^１Ｂが、１〜８の整数である、［１］〜［９］のいずれかに記載の発光素子。
［１１］前記Ｒ^１Ｂが、アルキル基、シクロアルキル基、アリール基、アルケニル基又はシクロアルケニル基（これらの基は置換基を有していてもよい）である、［１］〜［１０］のいずれかに記載の発光素子。
［１２］前記第１の有機層が、前記式（Ｂ）で表される発光材料とホスト材料とを含有する層であり、前記ホスト材料が式（ＦＨ−１）で表される化合物又は式（Ｙ）で表される構成単位を含む高分子化合物である、［１］〜［１１］のいずれかに記載の発光素子。

［式中、
Ａｒ^Ｈ１及びＡｒ^Ｈ２は、それぞれ独立に、アリール基、１価の複素環基又は置換アミノ基を表し、これらの基は置換基を有していてもよい。
ｎ^Ｈ１は、０〜１５の整数を表す。
Ｌ^Ｈ１は、アリーレン基、２価の複素環基、又は、−［Ｃ（Ｒ^Ｈ１１）_２］ｎ^Ｈ１１−で表される基を表し、これらの基は置換基を有していてもよい。Ｌ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。ｎ^Ｈ１１は、１〜１０の整数を表す。Ｒ^Ｈ１１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｈ１１は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。］

［式中、Ａｒ^Ｙ１は、アリーレン基、２価の複素環基、又は、少なくとも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。］
［１３］前記式（Ｂ）で表される発光材料の発光スペクトルの最大ピーク波長が３８０ｎｍ以上５７０ｎｍ以下である、［１］〜［１２］のいずれかに記載の発光素子。
［１４］前記第１の有機層と、前記第２の有機層とが、隣接している、［１］〜［１３］のいずれかに記載の発光素子。
［１５］前記第２の有機層が、前記陽極及び前記第１の有機層との間に設けられた層である、［１］〜［１４］のいずれかに記載の発光素子。[1] A light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode.
The first organic layer is a layer containing a light emitting material represented by the formula (B).
The maximum peak wavelength of the emission spectrum of the light emitting material represented by the formula (B) is 380 nm or more and 750 nm or less.
The second organic layer contains a crosslinked polymer compound containing a structural unit having a group represented by the formula (XL-A) and a structural unit having a group represented by the formula (XL-B). It is a layer to do
A light emitting device in which the group represented by the formula (XL-A) and the group represented by the formula (XL-B) are different groups from each other.

[During the ceremony,
n ^1B represents an integer of 0 to 15.
Ar ^1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
R ^1B is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl. Representing groups, these groups may have substituents. When a ^{plurality of R 1Bs} are present, they may be the same or different, or they may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

[During the ceremony,
nA and nB each independently represent an integer of 0 to 5.
L ^A and L ^B is independently an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups It may have a substituent. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A and L ^B there are a plurality, or different in each of them the same.
X ^A and X ^B each independently represent a cross-linking group. ]
[2] ^{The light emitting device according to [1], wherein the X A} or the X ^B is at least one cross-linking group selected from the cross-linking group A group.

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. ^{If there are multiple RXLs} , they may be the same or different, and ^{if there are multiple nXLs} , they may be the same or different. * 1 represents the bonding position. These cross-linking groups may have substituents. ]
[3] The cross-linking structural unit having a group represented by the formula (XL-A) is a structural unit represented by the formula (XL-A1) or a structural unit represented by the formula (XL-A2). The light emitting element according to [1] or [2].

[During the ceremony,
n ^A1 represents an integer of 1 to 4. When ^{there are a plurality of n A1} , they may be the same or different.
n ^A2 represents an integer of 0 or 1.
X ^LA represents a bridging group represented by the above formula (XL-A), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. If there are multiple X ^LAs , they may be the same or different. However, at least one ^XLA is a cross-linking group represented by the above formula (XL-A).
Ar ^A3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^A5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ^A4 and Ar ^A6 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^A4 , Ar ^A5 and Ar ^A6 each form a ring by directly or via an oxygen atom or a sulfur atom with a group other than the group bonded to the nitrogen atom to which the group is bonded. May be. ]
[4] The cross-linking structural unit having a group represented by the formula (XL-B) is a structural unit represented by the formula (XL-B1) or a structural unit represented by the formula (XL-B2). The light emitting element according to [1] or [2].

[During the ceremony,
n ^B1 represents an integer of 1 to 4. When ^{there are a plurality of n B1} , they may be the same or different.
n ^B2 represents an integer of 0 or 1.
X ^LB represents a bridging group represented by the above formula (XL-B), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. If there are multiple X ^LBs , they may be the same or different. However, at least one ^XLB is a cross-linking group represented by the above formula (XL-B).
Ar ^B3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^B5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ^B4 and Ar ^B6 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^B4 , Ar ^B5 and Ar ^B6 each form a ring by directly or via an oxygen atom or a sulfur atom with a group other than the group bonded to the nitrogen atom to which the group is bonded. May be. ]
[5] The ^{cross-linking group A} is a cross-linking group represented by the formula (XL-3), the formula (XL-4), the formula (XL-13) or the formula (XL-17) selected from the cross-linking group A group. The light emitting element according to any one of [2] to [4].
[6] formula wherein ^{X B} is selected from the crosslinking group A (XL-1), formula (XL-2), formula (XL-5), formula (XL-6), formula (XL-7) , The cross-linking group represented by the formula (XL-8), the formula (XL-14), the formula (XL-15) or the formula (XL-16), according to any one of [2] to [5]. Light emitting element.
[7] The light emitting device according to any one of [1] to [6], ^{wherein Ar 1B is an aromatic hydrocarbon group.}
[8] The Ar ^1B is a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a triphenylene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring, a chrysene ring, and the like. The light emission according to [7], which is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the indene ring, fluoranthene ring, benzofluoranthene ring or acenaftfluoranthene ring. element.
[9] The Ar ^1B comprises one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a biphenyl ring, a fluorene ring, a pyrene ring, a fluoranthene ring, a benzofluoranthene ring or an acenaftfluoranthene ring. The light emitting element according to [8], which is a group to be excluded.
[10] The light emitting device according to any one of [1] to [9], ^{wherein n 1B is an integer of 1 to 8.}
[11] ^{Of [1] to [10], wherein the R 1B} is an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group (these groups may have a substituent). The light emitting element according to any one.
[12] The first organic layer is a layer containing a light emitting material represented by the formula (B) and a host material, and the host material is a compound or a formula represented by the formula (FH-1). The light emitting element according to any one of [1] to [11], which is a polymer compound containing a structural unit represented by (Y).

[During the ceremony,
Ar ^H1 and Ar ^H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.
n ^H1 represents an integer from 0 to 15.
L ^H1 represents an arylene group, a divalent heterocyclic group, or ^{a group represented by − [C (RH11} ) ₂ ] n ^H11 −, and these groups may have a substituent. When ^{there are a plurality of L H1} , they may be the same or different. n ^H11 represents an integer of 1 to 10. ^RH11 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 ^RH11s existing may be the same or different, or may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

[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. The group of may have a substituent. ]
[13] The light emitting device according to any one of [1] to [12], wherein the maximum peak wavelength of the light emission spectrum of the light emitting material represented by the formula (B) is 380 nm or more and 570 nm or less.
[14] The light emitting device according to any one of [1] to [13], wherein the first organic layer and the second organic layer are adjacent to each other.
[15] The light emitting device according to any one of [1] to [14], wherein the second organic layer is a layer provided between the anode and the first organic layer.

According to the present invention, it is possible to provide a light emitting element having a low drive voltage.

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

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

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

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

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

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

By "low molecular compound" does not have a molecular weight distribution, molecular weight means a 1 × 10 ⁴ or less of the compound.

The “constituent unit” means a unit existing in one or more in a polymer compound.

The "alkyl group" may be linear or branched. The number of carbon atoms of the linear alkyl group is usually 1 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 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.

Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an isoamyl group, a 2-ethylbutyl group, a hexyl group and a heptyl. Examples include a group, an octyl group, a 2-ethylhexyl group, a 3-propylheptyl group, a decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, a 2-hexyldecyl group and a dodecyl group. The alkyl group may have a substituent, for example, a group in which a part or all of the hydrogen atom in the alkyl group is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like. It may be there. Examples of the alkyl group having a substituent include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group and a 3- (4-methylphenyl) group. Examples thereof include a propyl group, a 3- (3,5-di-hexylphenyl) propyl group and a 6-ethyloxyhexyl group.

The number of carbon atoms of the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20 without including the number of carbon atoms of the substituent.

Examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group. The cycloalkyl group may have a substituent, for example, a part or all of the hydrogen atom in the cycloalkyl group may be an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like. It may be a substituted group. Examples of the cycloalkyl group having a substituent include a cyclohexylmethyl group and a cyclohexylethyl group.

"Aryl group" means the remaining atomic group excluding 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 is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10 without including the number of carbon atoms of the substituent.

Examples of the aryl group include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthrasenyl group, a 2-anthrasenyl group, a 9-anthrasenyl group, a 1-pyrenyl group, a 2-pyrenyl group and a 4-pyrenyl group. Examples thereof include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group and 4-phenylphenyl group. The aryl group may have a substituent, for example, a part or all of the hydrogen atom in the aryl group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom and the like. It may be an atomic group.

The "alkoxy group" may be either linear or branched. The number of carbon atoms of the linear alkoxy group is usually 1 to 40, preferably 4 to 10 without including the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10 without including the number of carbon atoms of the substituent.

Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and 2 -Examples include ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group and lauryloxy group. The alkoxy group may have a substituent, for example, a group in which a part or all of the hydrogen atom in the alkoxy group is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like. It may be there.

The number of carbon atoms of the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10 without including the number of carbon atoms of the substituent.

Examples of the cycloalkoxy group include a cyclopentyloxy group and a cyclohexyloxy group. The cycloalkoxy group may have a substituent, for example, a part or all of the hydrogen atom in the cycloalkoxy group may be an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like. It may be a substituted group.

"Aryloxy group" means an atomic group in which one aryl group is bonded to an oxygen atom. The number of carbon atoms of the aryloxy group does not include the number of carbon atoms of the substituent and is usually 6 to 60, preferably 6 to 48.

Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthrasenyloxy group, a 9-anthrasenyloxy group and a 1-pyrenyloxy group. The aryloxy group may have a substituent, for example, a part or all of the hydrogen atom in the aryloxy group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom or the like. It may be a group.

A "p-valent heterocyclic group" (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. It means the remaining atomic group excluding the hydrogen atom of. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A "p-valent aromatic heterocyclic group" is preferred.

The "aromatic heterocyclic compound" is a complex such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphor, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinolin, carbazole, dibenzophosphol and the like. Compounds in which the ring itself exhibits aromaticity, and compounds in which an aromatic ring is condensed into the heterocycle even if the heterocycle itself such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran does not exhibit aromaticity. Means.

The number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, without including the number of carbon atoms of the substituent.

Examples of the monovalent heterocyclic group include a thienyl group, a pyrrolyl group, a frill group, a pyridyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group and a triazinyl group. The monovalent heterocyclic group may have a substituent, for example, a part or all of the hydrogen atom in the monovalent heterocyclic group is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or the like. It may be a substituted group.

The "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 the substituent contained in the amino group, 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. Specific substituted amino groups include, for example, a dimethylamino group, a diethylamino group, a diphenylamino group, a bis (4-methylphenyl) amino group, a bis (4-tert-butylphenyl) amino group and a bis (3,5-). Di-tert-butylphenyl) amino groups can be mentioned.

The "alkenyl group" may be either linear or branched. The number of carbon atoms of the linear alkenyl group is usually 2 to 30, not including the number of carbon atoms of the substituent, and is preferably 3 to 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.

Examples of the alkenyl group and the cycloalkenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-hexenyl group, and 5 -Hexenyl group and 7-octenyl group can be mentioned. The alkenyl group may have a substituent, for example, a group in which a part or all of the hydrogen atom in the alkenyl group is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like. It may be there. Further, the cycloalkenyl group may have a substituent, for example, a part or all of the hydrogen atom in the cycloalkenyl group is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a fluorine atom. It may be a group substituted with such as.

The "alkynyl group" may be either linear or branched. The number of carbon atoms of the alkynyl group is usually 2 to 20, not including the carbon atom of the substituent, and is preferably 3 to 20. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, without including the carbon atom of the substituent.

The number of carbon atoms of the "cycloalkynyl group" is usually 4 to 30, preferably 4 to 20, without including the carbon atom of the substituent.

Examples of the alkynyl group and the cycloalkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group and 5 -Hexynyl group is mentioned. The alkynyl group may have a substituent, for example, a group in which a part or all of the hydrogen atom in the alkynyl group is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like. It may be there. Further, the cycloalkynyl group may have a substituent, for example, a part or all of the hydrogen atom in the cycloalkynyl group is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a fluorine atom. It may be a group substituted with such as.

The "arylene group" means the remaining atomic group excluding two hydrogen atoms directly bonded to the carbon atom constituting the ring from the aromatic hydrocarbon. The number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent.

Examples of the arylene group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthreneyl group, a dihydrophenanthreneyl group, a naphthalsendiyl group, a full-orangeyl group, a pyrenediyl group, a perylenediyl group and a chrysendiyl group. The arylene group may have a substituent, for example, a part or all of the hydrogen atom in the arylene group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom and the like. It may be an atomic group.

The arylene group is preferably a group represented by the formulas (A-1) to (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

Wherein, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. R and R ^a there are a plurality, each may be the same or different, bonded R ^a each other to each other, they may form a ring together with the atoms bonded thereto.

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, not including the number of carbon atoms of the substituent.

Examples of the divalent heterocyclic group include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acrydin, dihydroaclydin, furan, thiophene and azole. Examples thereof include divalent groups obtained by removing two hydrogen atoms from the heterocyclic compounds such as diazole and triazole, among the hydrogen atoms directly bonded to the carbon atoms constituting the ring or the heteroatoms. The divalent heterocyclic group may have a substituent, for example, a part or all of the hydrogen atom in the divalent heterocyclic group may be an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl. It may be a group, a group substituted with a fluorine atom or the like.

The divalent heterocyclic group is preferably a group represented by the formulas (AA-1) to (AA-34). A divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

In the formula, R and ^Ra have the same meanings as described above.

The "crosslinking group" is a group capable of forming a new bond by being subjected to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc., and is preferably the above-mentioned crosslinking group. It is a group represented by the formulas (XL-1) to (XL-17) of the group A.

Examples of the "substituted group" include a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group and a substituted amino group. Examples thereof include an alkenyl group, a cycloalkenyl group, an alkynyl group and a cycloalkynyl group. The substituent may be a cross-linking group.

<Light emitting element>
Next, a light emitting device according to an embodiment of the present invention will be described.

The light emitting device according to the present embodiment has an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode. The first organic layer is a layer containing a light emitting material represented by the formula (B) (hereinafter, also referred to as “first light emitting material”), and the second organic layer is a layer of the formula (XL-A). ) Is a layer containing a crosslinked body of a polymer compound containing a crosslinked building block having a group represented by the formula (XL-B) and a crosslinked building block having a group represented by the formula (XL-B).

Examples of the method for forming the first organic layer and the second organic layer include a dry method such as a vacuum vapor deposition method and a wet method such as a spin coating method and an inkjet printing method, and the wet method is preferable.

When the first organic layer is formed by a wet method, it is preferable to use an ink for the first organic layer (hereinafter, also referred to as “first ink”), which will be described later.

When the second organic layer is formed by a wet method, it is preferable to use an ink for the second organic layer (hereinafter, also referred to as “second ink”), which will be described later. After forming the second organic layer, the polymer compound of the second organic layer, which will be described later, contained in the second organic layer can be crosslinked by heating or irradiating with light, and by heating, the second organic layer can be crosslinked. It is preferable to crosslink the polymer compound of the second organic layer described later contained in the organic layer of 2. When the polymer compound of the second organic layer described later is crosslinked (crosslinked body of the polymer compound of the second organic layer described later) and contained in the second organic layer, the second organic layer is used. Is substantially insoluble in the solvent. Therefore, the second organic layer can be suitably used for laminating light emitting elements.

The heating temperature for crosslinking is usually 25 to 300 ° C, preferably 50 to 250 ° C, more preferably 150 ° C to 200 ° C, still more preferably 170 ° C to 190 ° C. The heating time for crosslinking is usually 0.1 to 1000 minutes, preferably 0.5 to 500 minutes, more preferably 1-120 minutes, still more preferably 30 to 90 minutes. ..

The types of light used for light irradiation are, for example, ultraviolet light, near-ultraviolet light, and visible light.

Examples of the method for analyzing the components contained in the first organic layer or the second organic layer include a chemical separation analysis method such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and the like. Instrumental analysis methods such as mass spectrometry (MS), and analysis methods that combine chemical separation analysis methods and instrumental analysis methods can be mentioned.

By performing solid-liquid extraction of the first organic layer or the second organic layer using an organic solvent such as toluene, xylene, chloroform, or tetrahydrofuran, a component (insoluble) that is substantially insoluble in the organic solvent (insoluble). It is possible to separate a component) and a component (dissolving component) that dissolves in an organic solvent. The insoluble component can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and the dissolved component can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.

<First organic layer>
The first organic layer is a layer containing the first light emitting material. The first organic layer may contain the first light emitting material alone or in combination of two or more.

[First light emitting material]

The maximum peak wavelength of the emission spectrum of the first light emitting material is usually 380 nm or more and 750 nm or less, preferably 380 nm or more and 570 nm or less, more preferably 400 nm or more and 550 nm or less, and further preferably 420 nm or more and 520 nm or less. It is particularly preferably 430 nm or more and 510 nm or less.

In the present specification, the maximum peak wavelength of the emission spectrum of a compound is such that the compound is dissolved in an organic solvent such as xylene, toluene, chloroform, or tetrahydrofuran to prepare a dilute solution (1 × 10 ^-6 to 1 × 10 ^-3). It can be evaluated by measuring the PL spectrum of the dilute solution at room temperature (about mass%). Toluene is preferable as the organic solvent for dissolving the compound.

The first light emitting material is a compound represented by the formula (B).

[Compound represented by formula (B)]
n ^1B represents an integer of 0 to 15, preferably an integer of 1 to 8, more preferably an integer of 1 to 6, still more preferably an integer of 1 to 4, and particularly preferably 2 to 4. Is an integer of.

Ar ^1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group.

In Ar ^1B , the number of carbon atoms of the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 30.

Examples of the aromatic hydrocarbon group in Ar ^1B include a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a triphenylene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring and a perylene. Examples thereof include a group consisting of a ring, a chrysene ring, an inden ring, a fluorene ring, a benzofluorene ring or an acenaftfluorene ring excluding one or more hydrogen atoms directly bonded to carbon atoms constituting the ring. The aromatic hydrocarbon group is preferably a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a triphenylene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring or a chrysen. It is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the ring, fluoranthene ring, benzofluorentene ring or acenaftfluoranthene ring, and more preferably a benzene ring or biphenyl. A ring is composed of a ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring, a fluorantene ring, a benzofluorentene ring or an acenaftfluorene ring. A group consisting of one or more hydrogen atoms directly bonded to a carbon atom, more preferably a benzene ring, a biphenyl ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring, a fluoranthene ring, or a benzo. It is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the fluorentene ring or the acenaftfluorene ring, and particularly preferably, a biphenyl ring, a naphthalene ring, a fluorene ring, and pyrene. A group consisting of a ring, a pyrene ring, a fluoranthene ring, a benzofluorentene ring or an acenaftfluoranthene ring excluding one or more hydrogen atoms directly bonded to carbon atoms constituting the ring, and particularly preferably biphenyl. A group consisting of a ring, a fluorene ring, a pyrene ring, a fluoranthene ring, a benzofluorentene ring, or an acenaftfluoranthene ring, excluding one or more hydrogen atoms directly bonded to carbon atoms constituting the ring, and more particularly. Preferably, it is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a pyrene ring, a fluoranthen ring, a benzofluorantene ring or an acenaftfluoranthen ring.

In Ar ^1B , the number of carbon atoms of the aromatic heterocyclic group is usually 2 to 60, preferably 3 to 30, and more preferably 3 to 20.

Examples of the aromatic heterocyclic group in Ar ^1B include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, an indole ring, and a benzodi. Azole ring, benzotriazole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, phenazine ring or Examples thereof include a group consisting of a 5,10-dihydrophenazine ring excluding one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring. The aromatic heterocyclic group is preferably a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an indole ring, a benzodiazole ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a phenoxazine ring. , A phenothiazine ring, a 9,10-dihydroaclysine ring or a 5,10-dihydrophenazine ring from which one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring is removed, more preferably. A hydrogen atom directly bonded to a carbon atom or a heteroatom constituting a ring from a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, a benzodiazole ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring. It is a group except one.

Ar ^1B is preferably an aromatic hydrocarbon group.

R ^1B is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl. Representing groups, these groups may have substituents. R ^1B is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an alkenyl group or a cycloalkenyl group, and more preferably. , Alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group, alkenyl group or cycloalkenyl group, more preferably alkyl group, cycloalkyl group, aryl group, alkenyl group. Alternatively, it is a cycloalkenyl group, particularly preferably an alkyl group, an aryl group or an alkenyl group, and particularly preferably an aryl group. These groups may further have a substituent.

When R ^1B is an aryl group, the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 30 without including the number of carbon atoms of the substituent. It is more preferably 6 to 14.

When R ^1B is an aryl group, examples of the aryl group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, and a pyrene ring. Examples thereof include a group consisting of a perylene ring, a chrysene ring, an inden ring, a fluoranthene ring and a benzofluoranthene ring except for one hydrogen atom directly bonded to a carbon atom constituting the ring. The aryl group is preferably a carbon atom constituting a ring from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a fluorene ring or a benzofluorene ring. It is a group excluding one hydrogen atom directly bonded to, and more preferably constitutes a ring from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a spirobifluorene ring, a fluorene ring or a benzofluorene ring. It is a group excluding one hydrogen atom directly bonded to the carbon atom to be formed, and more preferably, the benzene ring, the naphthalene ring, the fluorene ring or the spirobifluorene ring is directly attached to the carbon atom constituting the ring. It is a group excluding one hydrogen atom to be bonded, and is particularly preferably a phenyl group, a naphthyl group or a fluorenyl group. These groups may further have a substituent.

When R ^1B is a monovalent heterocyclic group, the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 to 30, not including the number of carbon atoms of the substituent. Yes, more preferably 3 to 20.

When R ^1B is a monovalent heterocyclic group, the monovalent heterocyclic group includes, for example, a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, and a diazanaphthalene. Ring, triazanaphthalene ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring, 9,10-dihydroacridine ring, acridone ring, Examples thereof include a group consisting of a phenazine ring and a 5,10-dihydrophenazine ring excluding one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring. The monovalent heterocyclic group is preferably a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a carbazole ring, an azacarbazole ring, a diazacarbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a phenoxazine. It is a group consisting of a ring, a phenothiazine ring, a 9,10-dihydroaclydin ring or a 5,10-dihydrophenazine ring excluding one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring, and more preferably. , Pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring, except for one hydrogen atom directly bonded to the carbon atom or heteroatom constituting the ring. It is the basis of. These groups may further have a substituent.

The ^{substituent that R 1B} may have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom or an alkenyl group. Alternatively, it is a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, and even more preferably an alkyl group. , Cycloalkyl group, aryl group, alkenyl group or cycloalkenyl group, particularly preferably an alkyl group or an aryl group. These groups may further have a substituent.

The examples and preferred ranges of aryl groups and monovalent heterocyclic groups in the substituents that R ^1B may have are the same as the examples and preferred ranges of aryl groups and monovalent heterocyclic groups in ^{R 1B, respectively.} be.

The ^{substituent which R 1B} may have may further include an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group and an aryloxy group. A group, a halogen atom, an alkenyl group or a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group. , More preferably an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, and particularly preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent.

Examples and preferred ranges of aryl groups and monovalent heterocyclic groups in the substituents that the substituents that R ^1B may have may further include the aryl groups and monovalent complex in ^{R 1B, respectively.} It is the same as the example of a ring group and a preferable range.

Since the maximum peak wavelength of the emission spectrum of the compound represented by the formula (B) is a short wavelength, ^{it is preferable that when a plurality of R 1Bs} are present, they are bonded to each other and do not form a ring together with the atoms to which they are bonded.

Examples of the compound represented by the formula (B) include compounds represented by the following formula.

The compound represented by the formula (B) is described in Aldrich, Luminesis Technology Corp. , AK Scientific and the like. In addition, for example, International Publication No. 2007/100010, International Publication No. 2008/059713, International Publication No. 2011/012212, International Publication No. 2012/0962363, International Publication No. 2006/025273, International Publication No. 2006 It can be synthesized according to the method described in / 030527.

[Host material]
Since the drive voltage of the light emitting device according to the present embodiment is lower, the first organic layer is a group consisting of the first light emitting material and the hole injecting property, the hole transporting property, the electron injecting property, and the electron transporting property. It is preferable that the layer contains a host material having at least one function selected from the above. When the first organic layer is a layer containing the first light emitting material and the host material, the host material may be contained alone or in combination of two or more.

When the first organic layer is a layer containing the first light emitting material and the host material, the content of the first light emitting material is 100 parts by mass in total of the first light emitting material and the host material. If so, it is usually 0.05 to 80 parts by mass, preferably 0.1 to 50 parts by mass, more preferably 1 to 30 parts by mass, and further preferably 5 to 15 parts by mass.

When the first organic layer is a layer containing the first light emitting material and the host material, the lowest excited singlet state (S ₁ ) possessed by the host material is such that the driving voltage of the light emitting element according to the present embodiment is set. Since it is lower, it is preferable that the energy level is equivalent to or higher than that of _{S1 of the first light emitting material.} That is, the maximum peak wavelength of the emission spectrum of the host material is equal to or shorter than the maximum peak wavelength of the emission spectrum of the first light emitting material because the external quantum efficiency of the light emitting element according to the present embodiment is excellent. Is preferable.

As the host material, since the light emitting element according to the present embodiment can be produced by the solution coating process, it exhibits solubility in a solvent capable of dissolving the first light emitting material contained in the first organic layer. It is preferable that it is a thing.

Host materials are classified into low molecular weight compounds and high molecular weight compounds. Examples of the host material include a hole transport material described later and an electron transport material described later.

[Small molecule host]
A low molecular weight compound (hereinafter, also referred to as “low molecular weight host”) preferable as a host material will be described.

The small molecule host is preferably a compound represented by the formula (FH-1).

Ar ^H1 and Ar ^H2 are preferably an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have substituents.

When Ar ^H1 and Ar ^H2 are aryl groups, the number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 30, not including the number of carbon atoms of the substituent. It is 6 to 20, more preferably 6 to 14.

When Ar ^H1 and Ar ^H2 are aryl groups, the aryl groups include, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthalene ring, a fluorene ring, and a spirobifluorene ring. Examples thereof include a group consisting of a pyrene ring, a perylene ring, a chrysene ring, an inden ring, a fluoranthene ring or a benzofluoranthene ring except for one hydrogen atom directly bonded to a carbon atom constituting the ring. The aryl group is preferably a hydrogen atom directly bonded to a carbon atom constituting the ring from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring or a chrysen ring. It is a group excluding one, and more preferably one hydrogen atom directly bonded to a carbon atom constituting the ring from a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a fluorene ring or a spirobifluorene ring. It is a group to be excluded, more preferably a phenyl group, a naphthyl group or an anthrasenyl group, and particularly preferably a phenyl group or a naphthyl group. These groups may further have a substituent.

When Ar ^H1 and Ar ^H2 are monovalent heterocyclic groups, the number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 3 without including the number of carbon atoms of the substituent. It is ~ 30, and more preferably 3 to 20.

When Ar ^H1 and Ar ^H2 are monovalent heterocyclic groups, the monovalent heterocyclic group includes, for example, a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, and an azanaphthalene ring. Diazanaphthalene ring, triazanaphthalene ring, indole ring, benzodiazole ring, benzotriazole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, acridine ring , 9,10-Dihydroacridine ring, acridone ring, phenazine ring and 5,10-dihydrophenazine ring, except for one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring. The monovalent heterocyclic group is preferably a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an indole ring, a benzodiazole ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, or a phenoxazine. A group consisting of a ring, a phenothiazine ring, a 9,10-dihydroaclysine ring or a 5,10-dihydrophenazine ring excluding one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, more preferably. , Diazole ring, triazole ring, pyridine ring, diazabenzene ring, triazine ring, benzodiazole ring, benzotriazole ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring, hydrogen directly bonded to the carbon atom or heteroatom constituting the ring. It is a group excluding one atom. These groups may further have a substituent.

When Ar ^H1 and Ar ^H2 are substituted amino groups, the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups further have a substituent. May be. The examples and preferred ranges of aryl groups in the substituents of the amino groups are the same as the examples and preferred ranges of aryl groups in ^{Ar H1} and Ar ^H2. The example and preferred range of the monovalent heterocyclic group in the substituent of the amino group is the same as the example and preferred range of the monovalent heterocyclic group in ^{Ar H1} and Ar ^H2.

The ^{substituents that Ar H1} and Ar ^H2 may have are preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, and a substituted amino. It is a group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and more preferably an alkyl group or a cycloalkyl group. It is a group, an aryl group or a monovalent heterocyclic group, and particularly preferably an alkyl group, a cycloalkyl group or an aryl group. These groups may further have a substituent.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that Ar ^H1 and Ar ^{H2 may have are the aryl groups and monovalent complex in Ar H1} and Ar ^{H2, respectively.} It is the same as the example and preferable range of a ring group and a substituted amino group.

The ^{substituents that the substituents that Ar H1} and Ar ^H2 may have may further include, preferably, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, and the like. It is a cycloalkoxy group, an aryloxy group, a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group. , More preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and particularly preferably an alkyl group or a cycloalkyl group. These groups may further have a substituent.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that the substituents that Ar ^H1 and Ar ^{H2 may have may further have are Ar H1} and Ar, respectively. It is the same as the example and preferable range of the aryl group, the monovalent heterocyclic group and the substituted amino group in Ar ^H2.

n ^H1 is preferably an integer of 0 to 10, more preferably an integer of 1 to 5, and even more preferably an integer of 1 to 3.

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

The examples and preferred ranges of substituents that L ^H1 may have are the same as the examples and preferred ranges of substituents that Ar ^H1 and Ar ^H2 may have.

The arylene group in L ^H1 is preferably a group represented by the formula (A-1) to the formula (A-14) or the formula (A-17) to the formula (A-20), and more preferably the formula. It is a group represented by the formula (A-1) to the formula (A-9), the formula (A-11) to the formula (A-14), the formula (A-19) or the formula (A-20), and more preferably. Is a group represented by the formulas (A-1) to (A-7), formula (A-9), formulas (A-11) to formulas (A-14) or formulas (A-19). Particularly preferably, it is a group represented by the formulas (A-1) to (A-6), the formula (A-11) or the formula (A-12).

The ^{divalent heterocyclic group in L H1} is preferably the formula (AA-1) to the formula (AA-6), the formula (AA-10) to the formula (AA-22) or the formula (AA-24) to the formula. It is a group represented by (AA-34), and more preferably, the formulas (AA-1) to (AA-4), the formulas (AA-10) to the formulas (AA-15), and the formulas (AA-18). )-Formula (AA-21) or formula (AA-27) -formula (AA-34), more preferably formulas (AA-1) to formula (AA-4), formula (AA-4). AA-10) to a group represented by the formula (AA-15) or the formula (AA-27) to the formula (AA-32).

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

^RH11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and a hydrogen atom or an alkyl group. Is more preferable. These groups may have substituents.

^{The examples and preferred ranges of substituents that RH11} may have are the same as the examples and preferred ranges of substituents that Ar ^H1 and Ar ^H2 may have.

Examples of the compound represented by the formula (FH-1) include compounds represented by the following formula.

[Polymer host]
A polymer compound preferable as a host material (hereinafter, also referred to as “polymer host”) will be described.

The polymer host is preferably a polymer compound containing a structural unit represented by the formula (Y).

The ^{arylene group represented by Ar Y1} is preferably the formula (A-1), the formula (A-6), the formula (A-7), the formula (A-9) to the formula (A-11), and the formula (A). -13) or a group represented by the formula (A-19), more preferably the formula (A-1), the formula (A-7), the formula (A-9), the formula (A-11) or the formula. It is a group represented by (A-19). These groups may have substituents.

The ^{divalent heterocyclic group represented by Ar Y1} is preferably the formula (AA-4), the formula (AA-10), the formula (AA-13), the formula (AA-15), the formula (AA-18). Or a group represented by the formula (AA-20), more preferably a group represented by the formula (AA-4), the formula (AA-10), the formula (AA-18) or the formula (AA-20). Is. These groups may have substituents.

Preferred range of arylene group and 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, more preferable range.} Is the same as the preferable range and the more preferable range of the arylene group and the divalent heterocyclic group represented by ^{Ar Y1, respectively.}

The divalent group in which at least one arylene group represented by ^{Ar Y1} and at least one divalent heterocyclic group are directly bonded is at least represented by ^{Ar X2} and Ar ^{X4 of the formula (X).} Examples thereof include those similar to a divalent group in which one arylene group and at least one divalent heterocyclic group are directly bonded.

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

Examples of the structural unit represented by the formula (Y) include the structural units represented by the formulas (Y-1) to (Y-7), and the viewpoint of the drive voltage of the light emitting element according to the present embodiment. From the viewpoint, it is preferably a structural unit represented by the formula (Y-1) or the formula (Y-2), and from the viewpoint of electron transportability of the polymer host, the formula (Y-3) or the formula (Y-3) is preferable. It is a structural unit represented by Y-4), and is preferably a structural unit represented by the formulas (Y-5) to (Y-7) from the viewpoint of hole transportability of the polymer host.

In the formula, ^RY1 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 ^RY1s existing may be the same or different, and adjacent ^RY1s may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

^RY1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group. These groups may have substituents.

The structural unit represented by the formula (Y-1) is preferably the structural unit represented by the formula (Y-1').

In the formula, ^RY11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY11s may be the same or different.

^RY11 is preferably an alkyl group, a cycloalkyl group or an aryl group, and more preferably an alkyl group or a cycloalkyl group. These groups may have substituents.

In the formula, ^RY1 has 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. ^RY2 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 ^RY2s existing may be the same or different, and the ^RY2s may be bonded to each other to form a ring together with the carbon atoms to which the RY2s are bonded.

^RY2 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, -C (R Y2)}} 2 - 2 pieces of combinations of ^{R Y2} in the group represented by is preferably both an alkyl group or a cycloalkyl group, both aryl groups, both monovalent heterocyclic The ring 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. These groups may have substituents. The two existing ^RY2s may be bonded to each other to form a ring together with the atoms to which they are bonded, and when ^RY2 forms a ring, as a group represented by ^{−C (RY2} ) _{2 −.} Is preferably a group represented by the formulas (Y-A1) to (Y-A5), and more preferably a group represented by the formula (Y-A4). These groups may have substituents.

In ^{X Y1, -C (R Y2)} = C (R Y2) - 2 pieces of combinations of ^{R Y2} in the group represented by is preferably both an alkyl group or a cycloalkyl group, or, one is an alkyl group Alternatively, it is a cycloalkyl group and the other is an aryl group. These groups may have substituents.

In _{^{X Y1, -C (R Y2)}} 2 -C (R Y2) 2 - 4 pieces of ^{R Y2} in the group represented by is a preferably an optionally substituted alkyl group or a substituted group It is a cycloalkyl group that may have. Plural ^{R Y2,} taken together, each may form a ring together with the binding ^{atoms, if R Y2} form a ^{_{ring, -C (R Y2) 2 -C}} (R Y2) 2 - with The group represented is preferably a group represented by the formulas (Y-B1) to (Y-B5), and more preferably a group represented by the formula (Y-B3). These groups may have substituents.

In the formula, ^RY2 has the same meaning as described above.

The structural unit represented by the formula (Y-2) is preferably the structural unit represented by the formula (Y-2').

In the formula, ^RY1 and ^XY1 have the same meanings as described above.

In the formula, ^RY1 has the same meaning as described above. ^RY3 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.

^RY3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have substituents.

In the formula, ^RY1 has the same meaning as described above. ^RY4 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.

^RY4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have substituents.

Examples of the structural unit represented by the formula (Y) include the structural units represented by the formulas (Y-11) to (Y-56), and the structural units represented by the formulas (Y-11) to (Y-56) are preferable. It is a structural unit represented by Y-55).

The structural unit represented by the formula (Y) in which Ar ^Y1 is an arylene group has a lower driving voltage of the light emitting element according to the present embodiment, and thus is a structural unit included in the polymer host. It is preferably 10 to 100 mol%, more preferably 50 to 100 mol%, based on the total amount.

A structural unit represented by the formula (Y), in which Ar ^Y1 is 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. Since the structural unit which is the basis of the above is excellent in charge transportability of the polymer host, it is preferably 0.5 to 40 mol%, more preferably 3 with respect to the total amount of the structural units contained in the polymer host. ~ 30 mol%.

The structural unit represented by the formula (Y) may be contained in only one kind or two or more kinds in the polymer host.

Since the polymer host has excellent hole transportability, it is preferable that the polymer host further contains a structural unit represented by the formula (X).

During the ceremony
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 may have a substituent.
Ar ^X2 and Ar ^X4 each independently form 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. Representing, these groups may have substituents. When ^{there are a plurality of Ar X2} and Ar ^X4 , they may be the same or different.
^RX1 , ^RX2 and ^RX3 independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
When ^{there are a plurality of RX2} and ^RX3 , they may be the same or different.

a ^X1 is preferably an integer of 2 or less, and more preferably 1 because the drive voltage of the light emitting element according to the present embodiment is lower.

a ^X2 is preferably an integer of 2 or less, and more preferably 0, because the drive voltage of the light emitting element according to the present embodiment is lower.

^RX1 , ^RX2 and ^RX3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. These groups may have substituents.

The ^{arylene group represented by Ar X1} and Ar ^X3 is 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). Is. These groups may have substituents.

The ^{divalent heterocyclic group represented by Ar X1} and Ar ^X3 is preferably represented by the formula (AA-1), the formula (AA-2) or the formulas (AA-7) to (AA-26). It is the basis. These groups may have substituents.

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

The ^{arylene group represented by Ar X2} and Ar ^X4 is preferably a formula (A-1), a formula (A-6), a formula (A-7), a formula (A-9) to a formula (A-11) or. It is a group represented by the formula (A-19). These groups may have substituents.

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

A preferred range of an arylene group and a 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.} The more preferable range is the same as the preferable range and the more preferable range of the arylene group represented by ^{Ar X1} and Ar ^{X3 and the divalent heterocyclic group, respectively.}

Examples of the divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one divalent heterocyclic group are directly bonded include a group represented by the following formula. , These may have substituents.

In the formula, ^RXX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

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

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

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

In the formula, ^RX4 and ^RX5 are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, halogen atom, monovalent heterocyclic group or cyano group. These groups may have a substituent. A plurality of ^RX4s may be the same or different. A plurality of ^RX5s existing may be the same or different, and adjacent ^RX5s may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 50 mol%, more preferably 0.1 to 50 mol%, based on the total amount of the structural units contained in the polymer host. It is 1 to 40 mol%, more preferably 5 to 30 mol%.

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

In the polymer host, the structural unit represented by the formula (X) may contain only one kind or two or more kinds.

Examples of the polymer host include the polymer compounds (P-1) to (P-6) shown in Table 1. Here, the “other structural unit” means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).

In Table 1, p, q, r, s and t indicate the molar ratio of each structural unit. p + q + r + s + t = 100, and 100 ≧ p + q + r + s ≧ 70.

Examples and preferable ranges of the structural units represented by the formulas (X) and (Y) in the polymer compounds (P-1) to (P-6) are as described above.

The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, and other embodiments, but a plurality of kinds of raw material monomers are used together. It is preferably a copolymer obtained by polymerizing.

The polystyrene-equivalent number average molecular weight of the polymer host is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ^{4 to} 5 × 10 ⁵ , and even ^{more preferably 1.5 × 10 4.} ~ 2 × 10 ⁵ .

[Manufacturing method of polymer host]
The polymer host can be produced by using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc. Examples thereof include a method of polymerizing by a coupling reaction using a transition metal catalyst such as a reaction, a Negishi reaction and a Kumada reaction.

In the above-mentioned polymerization method, as a method of charging the monomers, a method of charging the entire amount of the monomers in a batch, a method of charging a part of the monomers and reacting them, and then collectively charging the remaining monomers. Examples thereof include a method of continuously or separately charging, a method of continuously or separately charging a monomer, and the like.

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

The post-treatment of the polymerization reaction is carried out by a known method, for example, a method of removing water-soluble impurities by separating liquids, a reaction liquid after the polymerization reaction is added to a lower alcohol such as methanol, the precipitated precipitate is filtered, and then dried. The method of making the mixture is used alone or in combination. When the purity of the polymer host is low, it can be purified by a usual method such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography and the like.

[First composition]
The first organic layer is composed of a first light emitting material, the above-mentioned host material, a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant, and a second light emitting material. It may be a layer containing a composition containing at least one material selected from the group (hereinafter, also referred to as “first composition”). However, in the first composition, the second light emitting material is different from the first light emitting material.

[Hole transport material]
The hole transport material is classified into a low molecular weight compound and a high molecular weight compound, and is preferably a high molecular weight compound. The hole transport material may have a cross-linking group.

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

In the first composition, the blending amount of the hole transporting material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass when the first light emitting material is 100 parts by mass.

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

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

Examples of the low molecular weight compound include a phosphorescent compound having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinonedimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinonedimethane, fluorenone, and diphenyldicyanoethylene. And diphenoquinone, as well as derivatives thereof.

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

In the first composition, the blending amount of the electron transporting material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass when the first light emitting material is 100 parts by mass.

The electron transport 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 classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injection material and the electron injection material may have a cross-linking 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; conductivity of polymers having an aromatic amine structure in the main chain or side chain. Examples include sex polymers.

In the first composition, the blending amount of the hole injection material and the electron injection material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, respectively, when the first light emitting material is 100 parts by mass. It is a mass part.

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

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

The type of ion to be doped is an anion in the case of a hole injection material and a cation in the case of an electron injection material. Examples of the anion include polystyrene sulfonic acid ion, alkylbenzene sulfonic acid ion, and cerebral sulfonic acid ion. Examples of the cation include lithium ion, sodium ion, potassium ion and tetrabutylammonium ion.

The type of ion to be doped may be used alone or in combination of two or more.

[Second light emitting material]
The second light emitting material is classified into a low molecular weight compound and a high molecular weight compound. The second light emitting material may have a cross-linking group.

Examples of the low molecular weight compound include naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and triple-term luminescent complexes having iridium, platinum or europium as a central metal.

Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorinatedyl group, a phenantrangeyl group, a dihydrophenantrangeyl group, a structural unit represented by the formula (X), a carbazolediyl group, a phenoxazinediyl group and a phenothiazine. Examples thereof include high molecular weight compounds containing a diyl group, an anthracene diyl group, a pyrienyl group and the like.

The second light emitting material preferably contains a triplet light emitting complex and / or a polymer compound.

Examples of the triplet luminescent complex include the following metal complexes.

In the first composition, the blending amount of the second light emitting material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, when the first light emitting material is 100 parts by mass.

The second light emitting material may be used alone or in combination of two or more.

[Antioxidant]
The antioxidant may be a compound that is soluble in the same solvent as the first light-emitting material and does not inhibit light emission and charge transport, and examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

In the first composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the first light emitting material is 100 parts by mass.

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

[First ink]
As the first ink for forming the first organic layer, a composition containing a first light emitting material and a solvent can be used. The first ink is a spin coat method, a casting method, a micro gravure coat method, a gravure coat method, a bar coat method, a roll coat method, a wire bar coat method, a dip coat method, a spray coat method, a screen printing method, and a flexographic printing method. , Offset printing method, inkjet printing method, capillary coating method, nozzle coating method and other wet methods can be suitably used.

The viscosity of the first ink may be adjusted according to the type of the wet method, but when the solution such as the inkjet printing method is applied to the printing method via the ejection device, clogging and flight bending occur at the time of ejection. Since it is difficult, it is preferably 1 to 20 mPa · s at 25 ° C.

The solvent contained in the first ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of the solvent include chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole, and 4-methylanisol; toluene, and the like. 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 solvent; Polyhydric alcohol solvent such as ethylene glycol, glycerin, 1,2-hexanediol; Alcohol solvent such as isopropyl alcohol and cyclohexanol; Sulfoxide solvent such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N , N-dimethylformamide and other amide-based solvents can be mentioned. The solvent may be used alone or in combination of two or more.

In the first ink, the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, when the first light emitting material is 100 parts by mass.

<Second organic layer>
The second organic layer is a polymer compound containing a cross-linked structural unit having a group represented by the formula (XL-A) and a cross-linked structural unit having a group represented by the formula (XL-B) (hereinafter, "" It is a layer containing a crosslinked body of (also referred to as "polymer compound of the second organic layer").

In the second organic layer, the crosslinked product of the polymer compound of the second organic layer may be contained alone or in combination of two or more.

The crosslinked body of the polymer compound of the second organic layer is obtained by cross-linking the polymer compound of the second organic layer by the above-mentioned method, conditions and the like.

[Polymer compound of the second organic layer]
In the polymer compound of the second organic layer, "the group represented by the formula (XL-A) and the group represented by the formula (XL-B) are different from each other" means that nA and nB are different. , the the ^{L a} and ^{L B} are different, or, means that the ^{X a} and ^{X B} differ.

nA and nB each independently represent an integer of 0 to 5, and since the drive voltage of the light emitting element according to the present embodiment is lower, it is preferably an integer of 0 to 3, and more preferably 0 to 2. It is an integer.

When nA and nB are different, one of nA and nB is preferably 0 or 1, one is 0 and the other is 1 or 2, or one, because synthesis is easy. Is 1 and the other is more preferably 0 or 2.

L ^A and L ^B is independently an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups It may have a substituent. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. L ^A and ^L number of carbon atoms in the alkylene group represented by ^B, not including the carbon atom number of substituent is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10 be. L ^A and L carbon atoms cycloalkylene group represented by ^B, not including the carbon atom number of substituent is usually 3 to 20.

The alkylene group represented by L ^A and L ^B, for example, methylene group, ethylene group, propylene group, butylene group, hexylene group, and octylene group. Alkylene group represented by L ^A and L ^B may have a substituent, and examples of the substituent, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom, a cyano group are preferable. These groups may further have a substituent.

The cycloalkylene group represented by L ^A and L ^B, for example, cyclopentylene group, cyclohexylene group and the like. Cycloalkylene group represented by L ^A and L ^B may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, cycloalkoxy group, a halogen atom, a cyano Groups are preferred. These groups may further have a substituent.

Arylene group represented by L ^A and L ^B may have a substituent. As the arylene group, a phenylene group or a fluoreneyl group is preferable, and an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, and a fluorene-9,9-diyl group are more preferable. The substituent that the arylene group may have includes an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group or a bridging group A. Bridging groups selected from the group are preferred. These groups may further have a substituent.

The divalent heterocyclic group represented by L ^A and ^{L B,} is preferably a group represented by the formula (AA-1) ~ formula (AA-34).

L ^A and L ^B, since production of the polymer compound of the second organic layer becomes easier, preferably, an arylene group or an alkylene group, more preferably a phenylene group, at fluorenediyl group or an alkylene group be. These groups may have substituents.

If the L ^A and L ^B are different, the driving voltage of the light emitting device according to this embodiment is lower, among the L ^A and L ^B, are preferably one of them is an alkylene group. Further, since the crosslinkable polymer compound of the second organic layer is more excellent, the combination of L ^A and L ^B is a combination of the two alkylene groups, combinations of the two arylene group or an alkylene group and arylene It is preferably a combination of groups, more preferably a combination of two alkylene groups, or a combination of an alkylene group and an arylene group.

X ^A and X ^B each independently represent a cross-linking group. Since X ^A or X ^B has a lower driving voltage of the light emitting element according to the present embodiment, it is preferable that X A or X B is at least one cross-linking group selected from the above-mentioned cross-linking group A group, and X ^A and X ^B are It is more preferable that the cross-linking group is at least one selected from the above-mentioned cross-linking group A group.

As the cross-linking group selected from the above-mentioned cross-linking group A group, since it is easy to synthesize, the formulas (XL-1) to (XL-4) and the formulas (XL-7) to (XL-10) are preferable. Alternatively, it is a cross-linking group represented by the formulas (XL-14) to (XL-17), and more preferably, the formula (XL-1), the formula (XL-3), the formula (XL-9), the formula ( It is a cross-linking group represented by the formula (XL-10), the formula (XL-16) or the formula (XL-17), and more preferably the formula (XL-1), the formula (XL-16) or the formula (XL-17). ), Especially preferably a cross-linking group represented by the formula (XL-1) or the formula (XL-17). In the formula in the cross-linking group A group, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, n ^XL represents an integer of 0 to 5, and * 1 represents a bond position.

Since crosslinking of the polymer compound of the second organic layer is more excellent, it is preferable that the X ^A and X ^B differ.

Crosslinking is better than the polymer compound of the second organic layer, and, since the driving voltage of the light emitting device according to this embodiment is lower, X ^A has the formula (XL-3), formula (XL-4 ), The cross-linking group represented by the formula (XL-13) or the formula (XL-17), and represented by the formula (XL-3), the formula (XL-4) or the formula (XL-17). It is more preferable that it is a cross-linking group, and it is further preferable that it is a cross-linking group represented by the formula (XL-17). Further, X ^B is a formula (XL-1), a formula (XL-2), a formula (XL-5), a formula (XL-6), a formula (XL-7), a formula (XL-8), a formula ( It is preferably a cross-linking group represented by the formula (XL-14), the formula (XL-15) or the formula (XL-16), and the formula (XL-1), the formula (XL-2), the formula (XL-14). , The cross-linking group represented by the formula (XL-15) or the formula (XL-16) is more preferable, and the cross-linking group represented by the formula (XL-1) or the formula (XL-16) is preferable. It is more preferable, and it is particularly preferable that it is a cross-linking group represented by the formula (XL-1).

The cross-linking structural unit having a group represented by the formula (XL-A) and the cross-linking structural unit having a group represented by the formula (XL-B) may be a structural unit represented by the following formula.

The cross-linking structural unit having a group represented by the formula (XL-A) is preferably a structural unit represented by the formula (XL-A1) or a structural unit represented by the formula (XL-A2). It is more preferable that the structural unit is represented by (XL-A1).

The cross-linking structural unit having a group represented by the formula (XL-B) is preferably a structural unit represented by the formula (XL-B1) or a structural unit represented by the formula (XL-B2). It is more preferable that the structural unit is represented by (XL-B1).

[Constituent units represented by the formula (XL-A1), the formula (XL-A2), the formula (XL-B1) and the formula (XL-B2)]
n ^A1 represents an integer of 1 to 4, and is preferably 1 or 2, and more preferably 2 because the drive voltage of the light emitting element according to the present embodiment is lower.

n ^A2 represents an integer of 0 or 1, and is preferably 0 because the production of the polymer compound of the second organic layer becomes easy and the drive voltage of the light emitting element according to the present embodiment becomes lower. be.

Ar ^A3 represents an aromatic hydrocarbon group or a heterocyclic group, and since the driving voltage of the light emitting element according to the present embodiment is lower, it is preferably an aromatic hydrocarbon group which may have a substituent. ..

The ^{number of carbon atoms of the aromatic hydrocarbon group represented by Ar A3} is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent. be.

Ar The ^{arylene group moiety excluding the n substituents of the aromatic hydrocarbon group represented by A3} is preferably represented by the groups represented by the formulas (A-1) to (A-20). Group, more preferably of the formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20). It is a group represented, and more preferably a group represented by the formula (A-1), the formula (A-2), the formula (A-7), the formula (A-9) or the formula (A-19). And these groups may have substituents.

The ^{number of carbon atoms of the heterocyclic group represented by Ar A3} is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, not including the number of carbon atoms of the substituent.

The ^{divalent heterocyclic group moiety excluding the n substituents of the heterocyclic group represented by Ar A3} is preferably a group represented by the formulas (AA-1) to (AA-34). be.

The ^{aromatic hydrocarbon group and the heterocyclic group represented by Ar A3} may have a substituent, and the substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group and an aryloxy group. Groups, halogen atoms, monovalent heterocyclic groups and cyano groups are preferred.

Ar ^A5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded. Ar ^A5 is an aromatic hydrocarbon group which may have a substituent because the driving voltage of the light emitting element according to the present embodiment is lower.

The definition and example of the arylene group portion excluding the m substituents of the aromatic hydrocarbon group represented by Ar ^A5 are the same as the definition and example of the arylene group represented by ^{Ar X2 in the formula (X).} ..

The definition and example of the divalent heterocyclic group portion excluding the m substituents of the heterocyclic group represented by Ar ^A5 is the divalent heterocyclic group portion represented by ^{Ar X2 in the formula (X).} Same as definition and example.

The definition and example of a divalent group excluding the m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ^{A5 and at least one heterocyclic ring are directly bonded are given by the formula (X).} It is the same as the definition and the example of the divalent group in which at least one arylene group represented by Ar ^{X2 and at least one divalent heterocyclic group are directly bonded.}

n ^B1 represents an integer of 1 to 4, and is preferably 1 or 2, and more preferably 2 because the drive voltage of the light emitting element according to the present embodiment is lower.

n ^B2 represents an integer of 0 or 1, and is preferably 0 because the production of the polymer compound of the second organic layer becomes easy and the drive voltage of the light emitting element according to the present embodiment becomes lower. be.

Ar ^B3 represents an aromatic hydrocarbon group or a heterocyclic group, and since the driving voltage of the light emitting element according to the present embodiment is lower, it is preferably an aromatic hydrocarbon group which may have a substituent. ..

The ^{number of carbon atoms of the aromatic hydrocarbon group represented by Ar B3} is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent. be.

The ^{arylene group moiety excluding the n substituents of the aromatic hydrocarbon group represented by Ar B3} is preferably represented by a group represented by the formulas (A-1) to (A-20). Group, more preferably of the formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20). It is a group represented, and more preferably a group represented by the formula (A-1), the formula (A-2), the formula (A-7), the formula (A-9) or the formula (A-19). And these groups may have substituents.

The ^{number of carbon atoms of the heterocyclic group represented by Ar B3} is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 18, not including the number of carbon atoms of the substituent.

The ^{divalent heterocyclic group moiety excluding the n substituents of the heterocyclic group represented by Ar B3} is preferably a group represented by the formulas (AA-1) to (AA-34). be.

The ^{aromatic hydrocarbon group and the heterocyclic group represented by Ar B3} may have a substituent, and the substituents include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group and an aryloxy group. Groups, halogen atoms, monovalent heterocyclic groups and cyano groups are preferred.

Ar ^B5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded. Ar ^B5 is an aromatic hydrocarbon group which may have a substituent because the driving voltage of the light emitting element according to the present embodiment is lower.

The definition and example of the arylene group portion excluding the m substituents of the aromatic hydrocarbon group represented by Ar ^B5 are the same as the definition and example of the arylene group represented by ^{Ar X2 in the formula (X).} ..

The definition and example of the divalent heterocyclic group portion excluding the m substituents of the heterocyclic group represented by Ar ^B5 is the divalent heterocyclic group portion represented by ^{Ar X2 in the formula (X).} Same as definition and example.

The definition and example of a divalent group excluding the m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ^{B5 and at least one heterocyclic ring are directly bonded are given in the formula (X).} It is the same as the definition and the example of the divalent group in which at least one arylene group represented by Ar ^{X2 and at least one divalent heterocyclic group are directly bonded.}

Ar ^A4 and Ar ^A6 independently represent an arylene group or a divalent heterocyclic group, respectively.

Ar ^B4 and Ar ^B6 independently represent an arylene group or a divalent heterocyclic group, respectively.

The definitions and examples of the arylene groups represented by Ar ^A4 , Ar ^A6 , Ar ^B4 and Ar ^B6 are the same as the definitions and examples of the arylene groups represented by ^{Ar X1} and Ar ^{X3 in the formula (X).}

The definitions and examples of the divalent heterocyclic groups represented by Ar ^A4 , Ar ^A6 , Ar ^B4 and Ar ^B6 are the definitions and examples of the divalent heterocyclic groups represented by ^{Ar X1} and Ar ^{X3 in the formula (X).} Same as the example.

The ^{groups represented by Ar A4} , Ar ^A5 , Ar ^A6 , Ar ^B4 , Ar ^B5 and Ar ^B6 may have a substituent, and the substituents include an alkyl group, a cycloalkyl group, an alkoxy group and a cycloalkoxy. Groups, aryl groups, aryloxy groups, halogen atoms, monovalent heterocyclic groups and cyano groups are preferred.

Since the structural unit represented by the formula (XL-A1) is excellent in stability and crosslinkability of the polymer compound of the second organic layer, the total amount of the structural units contained in the polymer compound of the second organic layer On the other hand, it is preferably 0.5 to 90 mol%, more preferably 3 to 70 mol%, and further preferably 5 to 50 mol%.

Since the structural unit represented by the formula (XL-B1) is excellent in stability and crosslinkability of the polymer compound of the second organic layer, the total amount of the structural units contained in the polymer compound of the second organic layer On the other hand, it is preferably 0.5 to 90 mol%, more preferably 3 to 70 mol%, and further preferably 5 to 50 mol%.

The structural unit represented by the formula (XL-A2) has excellent stability of the polymer compound of the second organic layer and excellent cross-linking property of the polymer compound of the second organic layer. It is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of the constituent units contained in the polymer compound of the organic layer. be.

The structural unit represented by the formula (XL-B2) has excellent stability of the polymer compound of the second organic layer and excellent cross-linking property of the polymer compound of the second organic layer. It is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, based on the total amount of the constituent units contained in the polymer compound of the organic layer. be.

The structural units represented by the formula (XL-A1), the formula (XL-B1), the formula (XL-A2), and the formula (XL-B2) are 1 in the polymer compound of the second organic layer, respectively. Only seeds may be contained, or two or more kinds may be contained.

[Preferable embodiment of the structural unit represented by the formula (XL-A1), the formula (XL-A2), the formula (XL-B1) and the formula (XL-B2)]
Examples of the structural unit represented by the formula (XL-A1) and the formula (XL-B1) include the structural units represented by the formulas (2-1) to (2-30), and the formula (XL) can be mentioned. Examples of the structural unit represented by −A2) and (XL-B2) include the structural units represented by the formulas (2'-1) to (2'-9). Among these, since the polymer compound of the second organic layer has excellent crosslinkability, it is preferably a structural unit represented by the formulas (2-1) to (2-30), and more preferably the formula (2). -1) to formula (2-15), formula (2-19), formula (2-20), formula (2-23), formula (2-25) or formula (2-30). It is a unit, and more preferably a structural unit represented by the formulas (2-1) to (2-9), formula (2-20), formula (2-22) or formula (2-30).

The total amount of the structural unit having a group represented by the formula (XL-A) and the structural unit having a group represented by the formula (XL-B) contained in the polymer compound of the second organic layer is the first. Since the polymer compound of the organic layer 2 has excellent stability and crosslinkability, it is preferably 0.5 to 90 mol% with respect to the total amount of the structural units contained in the polymer compound of the second organic layer. , More preferably 3 to 75 mol%, still more preferably 5 to 60 mol%.

Only one structural unit having a group represented by the formula (XL-A) and a structural unit having a group represented by the formula (XL-B) are contained in the polymer compound of the second organic layer, respectively. It may be contained, or two or more kinds may be contained.

[Other building blocks]
Since the polymer compound of the second organic layer has excellent hole transportability, it is preferable that the polymer compound further contains a structural unit represented by the formula (X). Further, the polymer compound of the second organic layer preferably further contains a structural unit represented by the formula (Y) because the driving voltage of the light emitting device according to the present embodiment is lower.

Since the polymer compound of the second organic layer has excellent hole transportability and the driving voltage of the light emitting device according to the present embodiment is lower, the structural unit and the formula represented by the formula (X) are further expressed. It is preferable to include the structural unit represented by (Y).

The definitions, examples and preferable ranges of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) which may be contained in the polymer compound of the second organic layer are the above-mentioned highs, respectively. It is the same as the definition, example and preferable range of the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) which the molecular host may include.

In the polymer compound of the second organic layer, the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) are contained in two or more types even if only one type is contained. May be.

Since the structural unit represented by the formula (X) has excellent hole transportability, it is preferably 0.1 to 90 mol% with respect to the total amount of the structural units contained in the polymer compound of the second organic layer. It is more preferably 1 to 70 mol%, still more preferably 10 to 50 mol%.

The structural unit represented by the formula (Y) in which Ar ^Y1 is an arylene group has a higher luminous efficiency of the light emitting element according to the present embodiment, and thus can be used as a polymer compound in the second organic layer. It is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of the constituent units contained.

A structural unit represented by the formula (Y), in which Ar ^Y1 is 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. Since the structural unit which is the basis of the above is excellent in charge transportability of the polymer compound of the second organic layer, it is preferably 0. It is 5 to 40 mol%, more preferably 3 to 30 mol%.

Examples of the polymer compound of the second organic layer include the polymer compounds (P-7) to (P-37) shown in Table 2. Here, the "other structural units" are the formula (XL-A1), the formula (XL-A2), the formula (XL-B1), the formula (XL-B2), the formula (X), and the formula (Y). It means a structural unit other than the represented structural unit.

In Table 2, p ′, p ″, q ′, q ″, r ′, s ′ and t ′ represent the molar ratio of each structural unit. p "+ p" + q "+ q" + r "+ s" + t "= 100, and 70≤p" + p "+ q" + q "+ r" + s "≤100.

Formulas (XL-A1), formulas (XL-A2), formulas (XL-B1), formulas (XL-B2), formulas (X) and formulas in the polymer compounds (P-7) to (P-37). Examples of the structural unit represented by (Y) and a preferable range are as described above.

The polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be another embodiment, but may be plural. It is preferably a copolymer obtained by copolymerizing a seed raw material monomer.

The number average molecular weight in terms of polystyrene of the polymer compound of the second organic layer is preferably ^{5 × 10 3 ~1 × 10 6} , more preferably from ^{1 × 10 4 ~5 × 10 5} , more preferably It is 1.5 × 10 ⁴ to 1 × 10 ⁵ .

[Method for producing polymer compound of second organic layer]
The polymer compound of the second organic layer can be produced by the same method as the above-mentioned method for producing a polymer host.

[Second composition]
The second organic layer is a group consisting of a crosslinked body of the polymer compound of the second organic layer, a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant, and a light emitting material. It may be a layer containing a composition containing at least one material selected from the above (hereinafter, also referred to as “second composition”).

Examples and preferred ranges of the hole transporting material, the electron transporting material, the hole injecting material, the electron injecting material and the light emitting material contained in the second composition are the hole transporting material contained in the first composition. Same as examples and preferred ranges of electron transport material, hole injection material, electron injection material and luminescent material.
In the second composition, the blending amounts of the hole transport material, the electron transport material, the hole injection material, the electron injection material and the light emitting material are 100 parts by mass, respectively, of the crosslinked body of the polymer compound of the second organic layer. , Usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

The examples and preferred ranges of the antioxidant contained in the second composition are the same as the examples and preferred ranges of the antioxidant contained in the first composition. In the second composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass when the crosslinked body of the polymer compound of the second organic layer is 100 parts by mass.

[Second ink]
As the second ink for forming the second organic layer, a composition containing the polymer compound of the second organic layer and the solvent can be used. The second ink can be suitably used for the wet method described in the section of the first ink. The preferred range of the viscosity of the second ink is the same as the preferred range of the viscosity of the first ink. The examples and preferred ranges of the solvent contained in the second ink are the same as the examples and preferred ranges of the solvent contained in the first ink.

In the second ink, the blending amount of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, when the polymer compound of the second organic layer is 100 parts by mass.

<Layer structure of light emitting element>
The light emitting device according to the present embodiment has an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode. The light emitting device according to the present embodiment may have a layer other than the anode, the cathode, the first organic layer, and the second organic layer.

In the light emitting device according to the present embodiment, the first organic layer is usually a light emitting layer (hereinafter, also referred to as "first light emitting layer").

In the light emitting device according to the present embodiment, the second organic layer is usually a hole transport layer, a light emitting layer (hereinafter, also referred to as “second light emitting layer”) or an electron transport layer, and is preferably a hole. It is a transport layer or a second light emitting layer, more preferably a hole transport layer.

In the light emitting element according to the present embodiment, the first organic layer and the second organic layer are preferably adjacent to each other because the driving voltage of the light emitting element is lower. In the light emitting device according to the present embodiment, the second organic layer is preferably a layer provided between the anode and the first organic layer because the driving voltage of the light emitting device is lower, and the anode and the first organic layer are preferable. A hole transport layer or a second light emitting layer provided between the organic layers 1 is more preferable, and a hole transport layer provided between the anode and the first organic layer is further preferable. ..

In the light emitting device according to the present embodiment, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the driving voltage of the light emitting device becomes lower, so that the anode and the first It is preferable to further have a hole injection layer between the two organic layers. Further, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that between the cathode and the first organic layer. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer.

In the light emitting element according to the present embodiment, when the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the drive voltage of the light emitting element becomes lower, so that the anode and the light emitting element It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the second organic layer. Further, when the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that the cathode and the first organic layer are separated from each other. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer in between.

In the light emitting device according to the present embodiment, when the second organic layer is the second light emitting layer provided between the cathode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that the anode and the light emitting element are used. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the first organic layer. Further, when the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that the cathode and the second organic layer are separated from each other. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer in between.

In the light emitting device according to the present embodiment, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the driving voltage of the light emitting device becomes lower, so that the anode and the first organic layer are used. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the organic layer and the hole transport layer. Further, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the driving voltage of the light emitting element becomes lower, so that between the cathode and the second organic layer. , It is preferable to further have an electron injection layer.

Specific layer configurations of the light emitting element according to the present embodiment include, for example, the layer configurations represented by the following (D1) to (D15). The light emitting element usually has a substrate, but may be laminated on the substrate from the anode, or may be laminated on the substrate from the cathode.

(D1) anode / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / cathode (D2) anode / hole transport layer (second organic layer) / second 1 light emitting layer (first organic layer) / cathode (D3) anode / hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / cathode (D4) anode / hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / cathode (D5) anode / hole injection layer / Second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D6) anode / hole injection layer / second light emitting layer (second (Organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D7) anode / hole injection layer / hole transport layer (second organic layer) / second 1 light emitting layer (first organic layer) / cathode (D8) anode / hole injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron transport Layer / cathode (D9) anode / hole injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D10) anode / hole Injection layer / hole transport layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D11) anode / hole injection layer / hole transport Layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode (D12) anode / hole injection layer / hole transport Layer (second organic layer) / first light emitting layer (first organic layer) / second light emitting layer / electron transport layer / electron injection layer / cathode (D13) anode / hole injection layer / hole transport Layer / first light emitting layer (first organic layer) / second light emitting layer (second organic layer) / electron transport layer / electron injection layer / cathode (D14) anode / hole injection layer / hole transport Layer / first light emitting layer (first organic layer) / electron transport layer (second organic layer) / electron injection layer / cathode (D15) anode / hole injection layer / hole transport layer (second organic) Layer) / second light emitting layer / first light emitting layer (first organic layer) / electron transport layer / electron injection layer / cathode

In the above (D1) to (D15), "/" means that the layers before and after the layer are adjacent to each other. Specifically, the "second light emitting layer (second organic layer) / first light emitting layer (first organic layer)" means the second light emitting layer (second organic layer) and the first. It means that the light emitting layer (first organic layer) of the above is adjacently laminated.

Since the drive voltage of the light emitting element according to the present embodiment is lower, the layer structure represented by (D3) to (D12) is preferable, and the layer structure represented by (D7) to (D10) is more preferable.

In the light emitting device according to the present embodiment, the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer, and the cathode are each provided with two or more layers, if necessary. May be.

When a plurality of anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers and cathodes are present, they may be the same or different from each other.

The thickness of the anode, the hole injection layer, the hole transport layer, the first light emitting layer, the second light emitting layer, the electron transport layer, the electron injection layer and the cathode is usually 1 nm to 1 μm, preferably 2 nm to 2 nm. It is 500 nm, more preferably 5 nm to 150 nm.

In the light emitting element according to the present embodiment, the order, number, and thickness of the layers to be laminated may be adjusted in consideration of the luminous efficiency of the light emitting element and the element life.

[Second light emitting layer]
The second light emitting layer is usually a second organic layer or a layer containing a light emitting material. When the second light emitting layer is a layer containing a light emitting material, examples of the light emitting material contained in the second light emitting layer include a light emitting material that may be contained in the above-mentioned first composition. Be done. The light emitting material contained in the second light emitting layer may be contained alone or in combination of two or more.

When the light emitting device according to the present embodiment has a second light emitting layer, and the hole transport layer and the electron transport layer described later are not the second organic layer, the second light emitting layer is the second light emitting layer. It is preferably an organic layer.

[Hole transport layer]
The hole transport layer is usually a second organic layer or a layer containing a hole transport material. When the hole transporting layer is a layer containing a hole transporting material, examples of the hole transporting material include a hole transporting material that may be contained in the above-mentioned first composition. The hole transport material contained in the hole transport layer may be contained alone or in combination of two or more.

When the light emitting device according to the present embodiment has a hole transport layer, and the second light emitting layer described above and the electron transport layer described later are not the second organic layer, the hole transport layer is the second organic layer. It is preferably a layer.

[Electron transport layer]
The electron transport layer is usually a second organic layer or a layer containing an electron transport material, preferably a layer containing an electron transport material. When the electron transport layer is a layer containing an electron transport material, examples of the electron transport material contained in the electron transport layer include an electron transport material that may contain the above-mentioned first composition. .. The electron transport material contained in the electron transport layer may be contained alone or in combination of two or more.

[Hole injection layer and electron injection layer]
The hole injection layer is a layer containing a hole injection material. Examples of the hole injection material contained in the hole injection layer include the hole injection material that may be contained in the above-mentioned first composition. The hole injection material contained in the hole injection layer may be contained alone or in combination of two or more.

The electron injection layer is a layer containing an electron injection material. Examples of the electron-injecting material contained in the electron-injecting layer include an electron-injecting material that may be contained in the above-mentioned first composition. The electron injection material contained in the electron injection layer may be contained alone or in combination of two or more.

[Substrate / Electrode]
The substrate in the light emitting element may be a substrate that can form an electrode and does not chemically change when an organic layer is formed, and is, for example, a substrate made of a material such as glass, plastic, or silicon. When using an opaque substrate, it is preferable that the electrode farthest from the substrate is transparent or translucent.

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

Materials for the cathode include, for example, metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more alloys thereof; one of them. Alloys of more than one species with one or more of silver, copper, manganese, titanium, cobalt, nickel, tungsten, tin; as well as graphite and graphite interlayer 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.

In the light emitting element according to the present embodiment, at least one of the anode and the cathode is usually transparent or translucent, but it is preferable that the anode is transparent or translucent.

Examples of the method for forming the anode and the cathode include a vacuum vapor deposition method, a sputtering method, an ion plating method, a plating method and a laminating method.

[Manufacturing method of light emitting element]
In the light emitting element according to the present embodiment, as a method for forming each layer such as a first light emitting layer, a second light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer, a low molecular weight compound is used. When using, for example, a vacuum vapor deposition method from a powder, a method by forming a film from a solution or a molten state, and when using a polymer compound, for example, a method by forming a film from a solution or a molten state can be mentioned.

The first light emitting layer, the second light emitting layer, the hole transport layer, the electron transport layer, the hole injection layer and the electron injection layer are the first ink, the second ink, and the above-mentioned light emitting material and holes. It can be formed by a wet method such as a spin coat method or an inkjet printing method using an ink containing a transport material, an electron transport material, a hole injection material, and an electron injection material, respectively.

[Use of light emitting element]
In order to obtain planar light emission using a light emitting element, the planar anode and cathode may be arranged so as to overlap each other. In order to obtain patterned light emission, a method of installing a mask having a patterned window on the surface of a planar light emitting element, or forming a layer to be a non-light emitting part extremely thick to make it 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 / OFF independently, a segment type display device capable of displaying numbers, characters, etc. can be obtained. In order to use the dot matrix display device, both the anode and the cathode may be formed in a striped shape and arranged so as to be orthogonal to each other. Partial color display and multi-color display are possible by a method of applying a plurality of types of polymer compounds having different emission colors separately, or a method of using a color filter or a fluorescence conversion filter. The dot matrix display device can be passively driven or can be actively driven in combination with a TFT or the like. These display devices can be used for displays such as computers, televisions, and mobile terminals. The planar light emitting element can be suitably used as a planar light source for a 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 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.

In the examples, the polystyrene-equivalent number average molecular weight (Mn) and the polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound are determined by size exclusion chromatography (SEC) (manufactured by Shimadzu Corporation, trade name: LC-10Avp). Asked by. The measurement conditions of SEC are as follows.
[Measurement condition]
The polymer compound to be measured was dissolved in tetrahydrofuran (THF) at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. THF was used as the mobile phase of the SEC and the flow was performed at a flow rate of 2.0 mL / min. PLgel MIXED-B (manufactured by Polymer Laboratories) was used as a column. A UV-VIS detector (manufactured by Shimadzu Corporation, trade name: SPD-10Avp) was used as the detector.

In this example, the maximum peak wavelength of the emission spectrum of the compound was measured at room temperature with a spectrophotometer (manufactured by JASCO Corporation, trade name: FP-6500). A toluene solution in which the compound was dissolved in xylene at ^{a concentration of about 0.8 × 10 -4} % by mass was used as a sample. As the excitation light, UV light having a wavelength of 325 nm was used.

<Compounds HM-1 to HM-6>
Compound HM-1 was synthesized according to the method described in JP-A-2011-174059.
Compound HM-2 was purchased from AK Scientific.
Compound HM-3 was synthesized according to the method described in International Publication No. 2011/137922.
Compound HM-4 and compound HM-5 were synthesized according to the methods described in JP-A-2011-147422 and International Publication No. 2011/137922.
Compound HM-6 was synthesized according to the method described in WO 2011/098030.

The maximum peak wavelength of the emission spectrum of compound HM-1 was 426 nm.
The maximum peak wavelength of the emission spectrum of compound HM-2 was 425 nm.
The maximum peak wavelength of the emission spectrum of compound HM-3 was 430 nm.
The maximum peak wavelength of the emission spectrum of compound HM-4 was 430 nm.
The maximum peak wavelength of the emission spectrum of compound HM-5 was 415 nm.
The maximum peak wavelength of the emission spectrum of compound HM-6 was 431 nm.

<Compounds EM-1 to EM-8, EM-10 and EM-11>
Compound EM-1 was synthesized according to the method described in JP-A-2011-176304.
Compound EM-2 was synthesized according to the method described in International Publication No. 2008/059713.
Compound EM-3 was synthesized according to the methods described in JP-A-2009-2900091 and JP-A-2011-176304.
Compound EM-4 and compound EM-10 were purchased from Tokyo Chemical Industry Co., Ltd.
Compound EM-5 was synthesized according to the method described in JP-A-2006-176491.
Compound EM-6 was synthesized according to the method described in International Publication No. 2010/013006.
Compound EM-7 was synthesized according to the method described in International Publication No. 2005/033051.
Compound EM-8 was synthesized according to the method described in JP-A-2007-142171.
Compound EM-11 was purchased from Aldrich.

<Synthesis Example EM-9> Synthesis of compound EM-9 Compound EM-9a (3.50 g) synthesized according to the method described in International Publication No. 2009/075203 after setting the inside of the reaction vessel to a nitrogen gas atmosphere. Compound EM-9b (9.00 g), tetrakis (triphenylphosphine) palladium (0) (0.294 g) synthesized according to the method described in JP-A-2015-110751, 20 wt% tetrabutylammonium hydroxide aqueous solution (9.00 g). 18.9 g) and toluene (52 mL) were added, and the mixture was stirred at 80 ° C. for 6 hours. The obtained reaction mixture was cooled to room temperature, hexane was added, and the precipitated solid was collected by filtration. The obtained solid was dissolved in toluene, washed with ion-exchanged water, and then the aqueous layer was removed. The obtained organic layer was filtered through a filter covered with silica gel, and the obtained filtrate was concentrated under reduced pressure. The obtained concentrate was crystallized using a mixed solvent of toluene and acetonitrile and dried under reduced pressure to obtain compound EM-9 (3.5 g). The HPLC area percentage value of compound EM-9 was 99.5% or more.

LC-MS (ESI, positive): m / z = 2043 [M] ⁺

The maximum peak wavelength of the emission spectrum of compound EM-1 was 439 nm.
The maximum peak wavelength of the emission spectrum of compound EM-2 was 441 nm.
The maximum peak wavelength of the emission spectrum of compound EM-3 was 460 nm.
The maximum peak wavelength of the emission spectrum of compound EM-4 was 446 nm.
The maximum peak wavelength of the emission spectrum of compound EM-5 was 446 nm.
The maximum peak wavelength of the emission spectrum of compound EM-6 was 453 nm.
The maximum peak wavelength of the emission spectrum of compound EM-7 was 453 nm.
The maximum peak wavelength of the emission spectrum of compound EM-8 was 502 nm.
The maximum peak wavelength of the emission spectrum of compound EM-9 was 440 nm.
The maximum peak wavelength of the emission spectrum of compound EM-10 was 404 nm.
The maximum peak wavelength of the emission spectrum of compound EM-11 was 448 nm.

<Compounds M1 to M8>
Compound M1 was synthesized according to the method described in JP-A-2011-174062.
Compound M2 was synthesized according to the method described in JP-A-2008-106241.
Compound M3 was synthesized according to the method described in WO 2015/145871.
Compound M4 was synthesized according to the method described in WO 2013/146806.
Compound M5 was synthesized according to the method described in WO 2005/049546.
Compound M6 was synthesized according to the method described in JP-A-2010-215886.
Compound M7 was synthesized according to the method described in WO 2013/146806.
Compound M8 was synthesized according to the method described in JP-A-2010-189630.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 Polymer compound HTL-1 was synthesized by using Compound M1, Compound M5 and Compound M2 according to the method described in JP-A-2013-47315. Mn of the polymer compound HTL-1 is 5.6 × 10 ^4, Mw was 2.4 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-1 has a structural unit derived from the compound M1, a structural unit derived from the compound M5, and a structural unit derived from the compound M2. It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.

<Synthesis Example HTL2> Synthesis of Polymer Compound HTL-2 Polymer compound HTL-2 was synthesized using Compound M5 and Compound M8 according to the method described in International Publication No. 2015/194448.

Mn of the polymer compound HTL-2 is 4.5 × 10 ^4, Mw was 1.5 × 10 ^5.

The polymer compound HTL-2 is composed of a structural unit derived from the compound M5 and a structural unit derived from the compound M8 in a molar ratio of 50:50 according to the theoretical value obtained from the amount of the charged raw material. Is a copolymer.

<Synthesis Example HTL3> Synthesis of Polymer Compound HTL-3 (Step 1) After creating an inert gas atmosphere in the reaction vessel, compound M1 (1.09 g), compound M5 (0.917 g), and compound M2 (0. 0669 g), compound M6 (0.0578 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) and toluene (35 mL) were added and heated to 105 ° C.
(Step 2) A 20 mass% tetraethylammonium hydroxide aqueous solution (22 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 5 hours.
(Step 3) After the reaction, phenylboronic acid (61 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.1 mg) were added thereto, and the mixture was refluxed for 18 hours.
(Step 4) After cooling the reaction solution, the reaction solution was washed twice with water, twice with a 3 mass% acetic acid aqueous solution, and twice with water, and the obtained solution was added dropwise to methanol to cause precipitation. The precipitate was dissolved in toluene and purified by passing it through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol, stirred, and then the obtained precipitate was collected by filtration and dried to obtain 1.31 g of the polymer compound HTL-3.

Mn of the polymer compound HTL-3 is 4.6 × 10 ^4, Mw was 1.5 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-3 has a structural unit derived from the compound M1, a structural unit derived from the compound M5, a structural unit derived from the compound M2, and a compound. The structural unit derived from M6 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Synthesis Example HTL4> Synthesis of Polymer Compound HTL-4 Polymer compound HTL-4 was synthesized by using Compound M3, Compound M4 and Compound M5 according to the method described in International Publication No. 2015/145871.

Mn of the polymer compound HTL-4 is 2.3 × 10 ^4, Mw was 1.2 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-4 has a structural unit derived from the compound M3, a structural unit derived from the compound M4, and a structural unit derived from the compound M5. It is a copolymer composed of a molar ratio of 45: 5: 50.

<Synthesis Example HTL5> Synthesis of Polymer Compound HTL-5 The polymer compound HTL-5 was synthesized by using the compound M8, the compound M7, the compound M2 and the compound M6 according to the method described in International Publication No. 2013/146806. ..

Mn of the polymer compound HTL-5 is 4.3 × 10 ^4, Mw was 3.6 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-5 has a structural unit derived from the compound M8, a structural unit derived from the compound M7, a structural unit derived from the compound M2, and a compound. The structural unit derived from M6 is a copolymer composed of a molar ratio of 50:40: 5: 5.

<Example D1> Fabrication and evaluation of light emitting device D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film to a glass substrate with a thickness of 45 nm by a sputtering method. ND-3202 (manufactured by Nissan Chemical Industries, Ltd.), which is a hole injection material, was formed on the anode to a thickness of 35 nm by a spin coating method. A hole injection layer was formed by heating at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes in an air atmosphere.

(Formation of the second organic layer)
The polymer compound HTL-4 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film was formed on the hole injection layer to a thickness of 20 nm by a spin coating method, and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere. Formed an organic layer of. By this heating, the polymer compound HTL-4 became a crosslinked product.

(Formation of the first organic layer)
Compound HM-2 and compound EM-2 (Compound HM-2 / Compound EM-2 = 91.5% by mass / 8.5% by mass) were dissolved in toluene at a concentration of 2% by mass. Using the obtained toluene solution, a film was formed on the second organic layer by a spin coating method to a thickness of 60 nm, and heated on a hot plate at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. 1 organic layer was formed.

(Cathode formation)
After reducing the pressure of the substrate on which the first organic layer was formed to 1 × 10 ^-4 Pa or less in the vapor deposition machine, sodium fluoride was placed on the first organic layer as a cathode at about 4 nm, and then fluoride. Aluminum was deposited on the sodium layer at about 80 nm. After the vapor deposition, the light emitting element D1 was manufactured by sealing with a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D1. The drive voltage at 400 cd / m ² was 5.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

<Example D2> Fabrication and evaluation of light emitting device D2 A light emitting device D2 was manufactured in the same manner as in Example D1 except that compound EM-1 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D2. The drive voltage at 400 cd / m ² was 5.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Example D3> Fabrication and evaluation of light emitting device D3 A light emitting device D3 was manufactured in the same manner as in Example D1 except that compound EM-3 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D3. The drive voltage at 400 cd / m ² was 6.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D4> Fabrication and evaluation of light emitting device D4 A light emitting device D4 was manufactured in the same manner as in Example D1 except that compound EM-4 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D4. The drive voltage at 400 cd / m ² was 6.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Example D5> Fabrication and evaluation of light emitting device D5 A light emitting device D5 was manufactured in the same manner as in Example D1 except that compound EM-5 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D5. The drive voltage at 400 cd / m ² was 5.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

<Example D6> Preparation and evaluation of light emitting element D6 A light emitting element D6 was produced in the same manner as in Example D1 except that compound EM-6 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D6. The drive voltage at 400 cd / m ² was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.18).

<Example D7> Fabrication and evaluation of light emitting device D7 A light emitting device D7 was manufactured in the same manner as in Example D1 except that compound EM-7 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D7. The drive voltage at 400 cd / m ² was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.24).

<Example D8> Fabrication and evaluation of light emitting device D8 A light emitting device D8 was manufactured in the same manner as in Example D1 except that compound EM-8 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D8. The drive voltage at 400 cd / m ² was 5.5 V, and the CIE chromaticity coordinates (x, y) were (0.25, 0.50).

<Example D9> Fabrication and evaluation of light emitting device D9 A light emitting device D9 was manufactured in the same manner as in Example D1 except that compound HM-3 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D9. The drive voltage at 400 cd / m ² was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.17).

<Example D10> Fabrication and evaluation of light emitting device D10 A light emitting device D10 was manufactured in the same manner as in Example D1 except that compound HM-4 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D10. The drive voltage at 400 cd / m ² was 5.8 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

<Example D11> Fabrication and evaluation of light emitting device D11 A light emitting device D11 was manufactured in the same manner as in Example D1 except that compound HM-5 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D11. The drive voltage at 400 cd / m ² was 5.2 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D12> Fabrication and evaluation of light emitting device D12 A light emitting device D12 was manufactured in the same manner as in Example D1 except that compound EM-9 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D12. The drive voltage at 400 cd / m ² was 5.3 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D13> Fabrication and evaluation of light emitting device D13 A light emitting device D13 was manufactured in the same manner as in Example D1 except that compound HM-6 was used instead of compound HM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D13. The drive voltage at 400 cd / m ² was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.18).

<Example D14> Fabrication and evaluation of light emitting device D14 A light emitting device D14 was manufactured in the same manner as in Example D13, except that compound EM-8 was used instead of compound EM-2 in Example D13.

EL light emission was observed by applying a voltage to the light emitting element D14. The drive voltage at 400 cd / m ² was 6.6 V, and the CIE chromaticity coordinates (x, y) were (0.25, 0.46).

<Example D15> Fabrication and evaluation of light emitting device D15 The light emitting device D15 is the same as that of Example D1 except that the polymer compound HTL-5 is used instead of the polymer compound HTL-4 in Example D1. Was produced.

EL light emission was observed by applying a voltage to the light emitting element D15. The drive voltage at 400 cd / m ² was 4.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

<Example D16> Fabrication and evaluation of light emitting device D16 The light emitting device D16 is the same as that of Example D1 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D1. Was produced.

EL light emission was observed by applying a voltage to the light emitting element D16. The drive voltage at 400 cd / m ² was 5.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.22).

<Comparative Example CD1> Fabrication and Evaluation of Light Emitting Element CD1 The light emitting element CD1 is the same as in Example D1 except that the polymer compound HTL-2 is used instead of the polymer compound HTL-4 in Example D1. Was produced.

EL light emission was observed by applying a voltage to the light emitting element CD1. The drive voltage at 400 cd / m ² was 7.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

The results of Examples and Comparative Examples are shown in Table 3.

<Example D17> Fabrication and evaluation of light emitting element D17 In Example D1 (formation of the first organic layer), "Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91. "Compound HM-1 and Compound EM-1 (Compound HM-1 / Compound EM-1 = 91.5% by mass / 8.5% by mass)" instead of "5% by mass / 8.5% by mass)" Further, light emission was carried out in the same manner as in Example D1 except that the polymer compound HTL-3 was used instead of the polymer compound HTL-4 in (formation of the second organic layer) of Example D1. The element D17 was manufactured.

EL light emission was observed by applying a voltage to the light emitting element D17. The drive voltage at 100 cd / m ^{2 was 10.0 V.}

<Example D18> Fabrication and evaluation of light emitting element D18 In Example D1 (formation of the first organic layer), "Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91. "Compound HM-1 and Compound EM-1 (Compound HM-1 / Compound EM-1 = 91.5% by mass / 8.5% by mass)" instead of "5% by mass / 8.5% by mass)" A light emitting element D18 was produced in the same manner as in Example D1 except that it was used.

EL light emission was observed by applying a voltage to the light emitting element D18. The drive voltage at 100 cd / m ^{2 was 9.2 V.}

<Comparative Example CD2> Preparation and evaluation of light emitting element CD2 In Example D1 (formation of the first organic layer), "Compound HM-2 and Compound EM-2 (Compound HM-2 / Compound EM-2 = 91. "Compound HM-1 and Compound EM-1 (Compound HM-1 / Compound EM-1 = 91.5% by mass / 8.5% by mass)" instead of "5% by mass / 8.5% by mass)" Further, light emission was carried out in the same manner as in Example D1 except that the polymer compound HTL-1 was used instead of the polymer compound HTL-4 in (formation of the second organic layer) of Example D1. The element CD2 was manufactured.

EL light emission was observed by applying a voltage to the light emitting element CD2. The drive voltage at 100 cd / m ^{2 was 11.7 V.}

The results of Examples and Comparative Examples are shown in Table 4.

<Example D19> Fabrication and evaluation of light emitting element D19 A light emitting element D19 was manufactured in the same manner as in Example D16.

EL light emission was observed by applying a voltage to the light emitting element D19. The drive voltage at 100 cd / m ² was 4.4 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Comparative Example CD3> Fabrication and evaluation of light emitting element CD3 Implementation except that the polymer compound HTL-1 was used instead of the polymer compound HTL-3 in (formation of the second organic layer) of Example D19. A light emitting element CD3 was produced in the same manner as in Example D19.

EL light emission was observed by applying a voltage to the light emitting element CD3. The drive voltage at 100 cd / m ² was 6.6 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

The results of Examples and Comparative Examples are shown in Table 5.

<Example D20> Fabrication and evaluation of light emitting element D20 A light emitting element D20 was manufactured in the same manner as in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D20. The drive voltage at 5000 cd / m ² was 9.1 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Example D21> Fabrication and evaluation of light emitting element D21 The light emitting element D21 was manufactured in the same manner as in Example D2.

EL light emission was observed by applying a voltage to the light emitting element D21. The drive voltage at 5000 cd / m ² was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20).

<Example D22> Fabrication and evaluation of light emitting element D22 A light emitting element D22 was manufactured in the same manner as in Example D12.

EL light emission was observed by applying a voltage to the light emitting element D22. The drive voltage at 5000 cd / m ² was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D23> Fabrication and evaluation of light emitting element D23 The light emitting element D23 was manufactured in the same manner as in Example D5.

EL light emission was observed by applying a voltage to the light emitting element D23. The drive voltage at 5000 cd / m ² was 9.5 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D24> Fabrication and evaluation of light emitting element D24 The light emitting element D24 was manufactured in the same manner as in Example D8.

EL light emission was observed by applying a voltage to the light emitting element D24. The drive voltage at 5000 cd / m ² was 8.8 V, and the CIE chromaticity coordinates (x, y) were (0.24,0.49).

<Example D25> Fabrication and evaluation of light emitting device D25 A light emitting device D25 was manufactured in the same manner as in Example D1 except that compound EM-10 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D25. The drive voltage at 5000 cd / m ² was 11.0 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.21).

<Comparative Example CD4> Fabrication and Evaluation of Light Emitting Element CD4 The light emitting element CD4 is the same as in Example D25, except that the polymer compound HTL-2 is used instead of the polymer compound HTL-4 in Example D25. Was produced.

EL light emission was observed by applying a voltage to the light emitting element CD4. The drive voltage at 5000 cd / m ² was 11.7 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.23).

<Comparative Example CD5> Preparation and Evaluation of Light Emitting Element CD5 A light emitting element CD5 was manufactured in the same manner as in Comparative Example CD1.

EL light emission was observed by applying a voltage to the light emitting element CD5. A voltage was applied up to 12 V, but did not reach ^{5000 cd / m 2.}

The results of Examples and Comparative Examples are shown in Table 6.

<Example D26> Fabrication and evaluation of light emitting element D26 A light emitting element D26 was manufactured in the same manner as in Example D6.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D26. The drive voltage at 7500 cd / m ² was 11.2 V, and the CIE chromaticity coordinates (x, y) were (0.14, 0.17).

<Example D27> Fabrication and evaluation of light emitting device D27 A light emitting device D27 was manufactured in the same manner as in Example D1 except that compound EM-11 was used instead of compound EM-2 in Example D1.

EL light emission was observed by applying a voltage to the light emitting element D27. The drive voltage at 7500 cd / m ^{2 was} 11.8 V, and the CIE chromaticity coordinates (x, y) were (0.16, 0.18).

According to the present invention, it is possible to provide a light emitting element having a low drive voltage.

Claims (15)

A light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode.
The first organic layer is a layer containing a light emitting material represented by the formula (B).
The maximum peak wavelength of the emission spectrum of the light emitting material represented by the formula (B) is 380 nm or more and 750 nm or less.
The second organic layer contains a crosslinked polymer compound containing a structural unit having a group represented by the formula (XL-A) and a structural unit having a group represented by the formula (XL-B). It is a layer to do
A light emitting device in which the group represented by the formula (XL-A) and the group represented by the formula (XL-B) are different groups from each other.

[During the ceremony,
n ^1B represents an integer of 1 to 15.
Ar ^1B represents an aromatic hydrocarbon group or an aromatic heterocyclic group.
R ^1B is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl. Representing groups, these groups may have substituents. When a ^{plurality of R 1Bs} are present, they may be the same or different, or they may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

[During the ceremony,
nA and nB each independently represent an integer of 0 to 5.
L ^A and L ^B is independently an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups It may have a substituent. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A and L ^B there are a plurality, or different in each of them the same.
X ^A and X ^B represent different cross-linking groups. ] The light emitting device according to claim 1, wherein the X ^A or the X ^B is at least one cross-linking group selected from the cross-linking group A group.

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. ^{If there are multiple RXLs} , they may be the same or different, and ^{if there are multiple nXLs} , they may be the same or different. * 1 represents the bonding position. These cross-linking groups may have substituents. ] Claim 1 in which the cross-linking structural unit having a group represented by the formula (XL-A) is a structural unit represented by the formula (XL-A1) or a structural unit represented by the formula (XL-A2). Or the light emitting element according to 2.

[During the ceremony,
n ^A1 represents an integer of 1 to 4. When ^{there are a plurality of n A1} , they may be the same or different.
n ^A2 represents an integer of 0 or 1.
X ^LA represents a bridging group represented by the above formula (XL-A), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. If there are multiple X ^LAs , they may be the same or different. However, at least one ^XLA is a cross-linking group represented by the above formula (XL-A).
Ar ^A3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^A5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ^A4 and Ar ^A6 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^A4 , Ar ^A5 and Ar ^A6 each form a ring by directly or via an oxygen atom or a sulfur atom with a group other than the group bonded to the nitrogen atom to which the group is bonded. May be. ] Claim 1 in which the cross-linking structural unit having a group represented by the formula (XL-B) is a structural unit represented by the formula (XL-B1) or a structural unit represented by the formula (XL-B2). Or the light emitting element according to 2.

[During the ceremony,
n ^B1 represents an integer of 1 to 4. When ^{there are a plurality of n B1} , they may be the same or different.
n ^B2 represents an integer of 0 or 1.
X ^LB represents a bridging group represented by the above formula (XL-B), a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups have a substituent. May be. If there are multiple X ^LBs , they may be the same or different. However, at least one ^XLB is a cross-linking group represented by the above formula (XL-B).
Ar ^B3 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
Ar ^B5 represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ^B4 and Ar ^B6 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^B4 , Ar ^B5 and Ar ^B6 each form a ring by directly or via an oxygen atom or a sulfur atom with a group other than the group bonded to the nitrogen atom to which the group is bonded. May be. ] Claimed ^{that the cross-linking group A} is a cross-linking group represented by the formula (XL-3), the formula (XL-4), the formula (XL-13) or the formula (XL-17) selected from the cross-linking group A group. Item 2. The light emitting element according to any one of Items 2 to 4. Wherein ^{X B} is formula selected from the crosslinking group A (XL-1), formula (XL-2), formula (XL-5), formula (XL-6), formula (XL-7), formula ( The light emitting device according to any one of claims 2 to 5, which is a cross-linking group represented by XL-8), formula (XL-14), formula (XL-15) or formula (XL-16). The light emitting device according to any one of claims 1 to 6, wherein Ar ^{1B is an aromatic hydrocarbon group.} The Ar ^1B is a benzene ring, a biphenyl ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a triphenylene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring, a chrysene ring, an inden ring, and the like. The light emitting element according to claim 7, wherein the group is formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the fluoranthene ring, the benzofluoranthene ring or the acenaftfluoranthene ring. The Ar ^1B is formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the biphenyl ring, fluorene ring, pyrene ring, fluoranthene ring, benzofluoranthene ring or acenaftfluoranthene ring. The light emitting element according to claim 8, which is a base. The light emitting device according to any one of claims 1 to 9, wherein n ^{1B is an integer of 1 to 8.} Wherein R ^1B is an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group (which may have these groups the substituents), to any one of claims 1 to 10 The light emitting element described. The first organic layer is a layer containing a light emitting material represented by the formula (B) and a host material.
The light emitting device according to any one of claims 1 to 11, wherein the host material is a compound represented by the formula (FH-1) or a polymer compound containing a structural unit represented by the formula (Y).

[During the ceremony,
Ar ^H1 and Ar ^H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.
n ^H1 represents an integer from 0 to 15.
L ^H1 represents an arylene group, a divalent heterocyclic group, or ^{a group represented by − [C (RH11} ) ₂ ] n ^H11 −, and these groups may have a substituent. When ^{there are a plurality of L H1} , they may be the same or different. n ^H11 represents an integer of 1 to 10. ^RH11 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 ^RH11s existing may be the same or different, or may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

[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. The group of may have a substituent. ] The light emitting device according to any one of claims 1 to 12, wherein the maximum peak wavelength of the light emission spectrum of the light emitting material represented by the formula (B) is 380 nm or more and 570 nm or less. The light emitting device according to any one of claims 1 to 13, wherein the first organic layer and the second organic layer are adjacent to each other. The light emitting device according to any one of claims 1 to 14, wherein the second organic layer is a layer provided between the anode and the first organic layer.