JP6982566B2 - Light emitting element - Google Patents

Description

The present invention relates to a light emitting device.

Organic electroluminescence devices (hereinafter, also referred to as "light emitting devices") can be suitably used for display and lighting applications, and in recent years, research and development of organic electroluminescence devices having a long life and high luminous efficiency. Is being done.

For example, Patent Document 1 describes an organic electroluminescence device in which an organic thin film layer including at least a light emitting layer is sandwiched between a cathode and an anode, wherein the light emitting layer contains a compound having a fluoranthene structure and a fused ring-containing compound. An electroluminescence element is described (claim 1). Specific examples of the compound having a fluoranthene structure include compounds (2-29) and (2-21) represented by the following formulas (paragraph 0110). Specific examples of the fused ring compound include compounds (2a'-55) represented by the following formulas (paragraph 0122).

In Example 13 of Patent Document 1, an organic electroluminescence device containing the compound (2-29) and the compound (2a'-55) in the light emitting layer is described. In the organic electroluminescence device of Example 13, the light emitting layer is a thin-film deposition layer formed by simultaneously depositing compound (2-29) and compound (2a'-55) on a hole transport layer. The hole transport layer is a thin-film deposition layer formed by depositing N, N, N'N'-tetra (4-biphenylyl) benzidine on a hole-injection layer (paragraph 0171).

Further, in Example 21 of Patent Document 1, an organic electroluminescence device containing the compound (2-21) and the compound (2a'-55) in the light emitting layer is described. In the organic electroluminescence element of Example 21, the light emitting layer is a coating layer formed by spin-coating a toluene solution of the compound (2-21) and the compound (2a'-55) onto the hole transport layer. Is. The hole transport layer is a coating layer formed by spin-coating a toluene solution of polymer 1 represented by the following formula on a hole injection layer (paragraph 0177).

ポリマー１

Polymer 1

International Publication No. 2007/100010

However, in the above-mentioned conventional light emitting element, the drive voltage is not sufficiently low and needs to be further lowered.

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 [11].

[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 composition containing the first compound and the first light emitting material, and the maximum peak wavelength of the light emitting spectrum of the first light emitting material is 380 nm or more and 570 nm or less.
The maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first emission material.
The first compound is a compound represented by the formula (1A).
The first light emitting material is a compound represented by the formula (1A) or a compound represented by the formula (1B).
A light emitting device in which the second organic layer is a layer containing a crosslinked body of a crosslinking material.

［式中、
ｎ^1Ａは、１以上１０以下の整数を表す。
ｎ^2Ａは、０以上１０以下の整数を表す。
Ａｒ^1Ａは、３個以上１０個以下のベンゼン環が縮合した、縮合環の芳香族炭化水素基を表す。
Ｒ^1Ａは、縮合環のアリール基を表し、該基は置換基を有していてもよい。Ｒ^1Ａが複数存在する場合、同一でも異なっていてもよい。
Ｒ^２Ａは、ハロゲン原子、シアノ基、アルキル基、シクロアルキル基、単環のアリール基、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^２Ａが複数存在する場合、同一でも異なっていてもよい。
］

[During the ceremony,
n ^1A represents an integer of 1 or more and 10 or less.
n ^2A represents an integer of 0 or more and 10 or less.
Ar ^1A represents an aromatic hydrocarbon group of a fused ring in which 3 or more and 10 or less benzene rings are condensed.
R ^1A represents an aryl group of the fused ring, which group may have a substituent. When ^{there are a plurality of R 1A} , they may be the same or different.
R ^2A is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, a monocyclic aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, and an alkynyl group. Alternatively, it represents a cycloalkynyl group, and these groups may have a substituent. When ^{there are a plurality of R 2A} , they may be the same or different.
]

［式中、
ｎ^1Ｂは、０以上１０以下の整数を表す。
Ａｒ^1Ｂは、芳香族炭化水素基を表す。
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炭素原子とともに環を形成していてもよい。
但し、Ａｒ^1Ｂは、３個以上１０個以下のベンゼン環が縮合した、縮合環の芳香族炭化水素基である場合、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、単環のアリール基、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。］

[During the ceremony,
n ^1B represents an integer of 0 or more and 10 or less.
Ar ^1B represents 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. 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 carbon atoms to which they are bonded.
However, when Ar ^1B is an aromatic hydrocarbon group of a fused ring in which 3 or more and 10 or less benzene rings are condensed, R ^1B is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group or a monocyclic ring. It represents 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 group, and these groups may have a substituent. .. ]

[2] The cross-linking material is
It is a low molecular weight compound having at least one cross-linking group selected from the cross-linking group A group, or a high molecular compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group [1]. The light emitting element according to.
(Crosslink group A group)

［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。］

[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 light emitting element according to [2], wherein the cross-linking material is a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group.

[4] The light emitting device according to [3], wherein the crosslinked structural unit is a structural unit represented by the formula (2) or a structural unit represented by the formula (2').

［式中、
ｎＡは０〜５の整数を表し、ｎは１又は２を表す。ｎＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ^３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。
Ｌ^Ａは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子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が複数存在する場合、それらは同一でも異なっていてもよい。
Ｘは、架橋基Ａ群から選ばれる架橋基を表す。Ｘが複数存在する場合、それらは同一でも異なっていてもよい。］

[During the ceremony,
nA represents an integer from 0 to 5, and n represents 1 or 2. When there are a plurality of nA, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A is plurally present, they may be the same or different.
X represents a cross-linking group selected from the group A of cross-linking groups. If there are multiple X's, they may be the same or different. ]

［式中、
ｍＡは０〜５の整数を表し、ｍは１〜４の整数を表し、ｃは０又は１の整数を表す。ｍＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ^５は、芳香族炭化水素基、複素環基、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^４及びＡｒ^６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^４、Ａｒ^５及びＡｒ^６はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接又は酸素原子もしくは硫黄原子を介して結合して、環を形成していてもよい。
Ｋ^Ａは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子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。Ｋ^Ａが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘ’は、架橋基Ａ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は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’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’は、架橋基Ａ群から選ばれる架橋基である。］

[During the ceremony,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. If there are multiple mAs, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ 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.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If K ^A there are a plurality, they may be the same or different.
X'represents a cross-linking group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group selected from the cross-linking group A group, and these groups may have a substituent. If there are multiple X's, they may be the same or different. However, at least one X'is a cross-linking group selected from the group A of cross-linking groups. ]

[5] The light emitting device according to [1], wherein the crosslinked material is a low molecular weight compound represented by the formula (3).

［式中、
ｍ^B1、ｍ^B2及びｍ^B3は、それぞれ独立に、０以上の整数を表す。複数存在するｍ^B1は、同一でも異なっていてもよい。ｍ^B3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。
Ａｒ⁷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。Ａｒ⁷が複数存在する場合、それらは同一でも異なっていてもよい。
Ｌ^B1は、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−Ｎ(Ｒ’’’)−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^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。
Ｘ’’は、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。複数存在するＸ’’は、同一でも異なっていてもよい。但し、複数存在するＸ’’のうち、少なくとも１つは、架橋基である。］

[During the ceremony,
m ^B1 , m ^B2, and m ^B3 independently represent integers of 0 or more. A plurality of m ^B1s may be the same or different. If there are multiple m ^B3s , they may be the same or different.
Ar ⁷ 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. If Ar ⁷ there are a plurality, they may be the same or different.
^LB1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by −N (R ′'') −, an oxygen atom or a sulfur atom, and these groups are substituents. May have. 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 there are multiple LB1} , they may be the same or different.
X'' represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of X''s may be the same or different. However, at least one of the plurality of X''s present is a cross-linking group. ]

[6] The Ar ^1A is an anthracene ring, a phenanthrene ring, or a ring in which one or more and seven or less benzene rings are condensed on these rings, and one or more hydrogen atoms directly bonded to carbon atoms constituting the ring. The light emitting element according to any one of [1] to [5], which is a group excluding the above.

[7] The compound represented by the formula (1A) is a formula (1A-A1), a formula (1A-A2), a formula (1A-A3), a formula (1A-A4), a formula (1A-A5) or. The light emitting element according to any one of [1] to [6], which is a compound represented by the formula (1A-A6).

[8] The R ^1A is a naphthalene ring, an anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthacene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysene ring, inden ring, fluoranthene ring or A group consisting of a benzofluoranthene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring (the group may have a substituent), [1] to [7]. The light emitting element according to any one of.

[9] The Ar ^1B comprises 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. [1] to [8], which is a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from an inden ring, a fluoranthene ring, a benzofluoranthene ring, or an acenaftfluoranthene ring. The light emitting element according to any one of.

[10] The light emitting device according to any one of [1] to [9], wherein the first organic layer and the second organic layer are adjacent to each other.

[11] The light emitting device according to any one of [1] to [10], wherein the second organic layer is a layer provided between the anode and the first organic layer.

[12] A method for manufacturing 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 composition containing the first compound and the first light emitting material.
The maximum peak wavelength of the emission spectrum of the first light emitting material is 380 nm or more and 570 nm or less.
The maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first emission material.
The first compound is a compound represented by the formula (1A).
The first light emitting material is a compound represented by the formula (1A) or a compound represented by the formula (1B).
The second organic layer is a layer containing a crosslinked body of a crosslinking material.
A step of forming a crosslinked material for forming a second organic layer by a wet method,
A method for manufacturing a light emitting element, comprising a step of cross-linking the formed second organic layer and a step of forming an organic layer on the cross-linked second organic layer by a wet method.

[13] The method for manufacturing a light emitting device according to [12], wherein the organic layer formed on the crosslinked second organic layer by a wet method is 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 is a methyl group, Et is an ethyl group, Bu is a butyl group, i-Pr is an isopropyl group, and t-Bu is 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 .

"Low molecular weight compound" means a compound having no molecular weight distribution and having a molecular weight of 1 × 10 ^{4 or less.}

The “constituent unit” means a unit 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.
The alkyl group may have a substituent, for example, 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, and the like. 2-Ethylbutyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group. , And a group in which the hydrogen atom in these groups is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom or the like, and examples thereof include a trifluoromethyl group, a pentafluoroethyl group and a per. Fluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3,5-di-hexylphenyl) propyl group, 6-ethyloxy A hexyl group can be mentioned.
The number of carbon atoms of the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.
The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, 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, not including the number of carbon atoms of the substituent.
The aryl group may have a substituent, for example, 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, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups. However, examples thereof include a group substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom and the like.

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, not 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, not including the number of carbon atoms of the substituent.
The alkoxy group may have a substituent, for example, 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, and the like. Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is cycloalkyl group, alkoxy group, Examples thereof include a cycloalkoxy group, an aryl group, a group substituted with a fluorine atom and the like.
The number of carbon atoms of the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

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

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

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.
Examples of the amino group include 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.
The alkenyl group and the cycloalkenyl group may have a substituent, for example, 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- Examples thereof include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and a group in which these groups have a substituent.

The "alkynyl group" may be 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.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, 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-. Examples thereof include a pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and a group in which these groups have a substituent.

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.
The arylene group may have a substituent, for example, a phenylene group, a naphthalenediyl group, an anthrasendiyl group, a phenanthrangeyl group, a dihydrophenantrenidyl group, a naphthacendyl group, a full orangeyl group, a pyrenylyl group, a perylenediyl group, and the like. Examples thereof include a chrysendiyl group and a group in which these groups have a substituent, and the groups represented by the formulas (A-1) to (A-20) are preferable. The arylene group includes a group in which a plurality of these groups are bonded.

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

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

The number of carbon atoms of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15, not including the number of carbon atoms of the substituent.
The divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, aclysine, A divalent group obtained by removing two hydrogen atoms from the hydrogen atoms directly bonded to the carbon atom or the hetero atom constituting the ring from dihydroaclydin, furan, thiophene, azole, diazole and triazole is preferable. Is a group represented by equations (AA-1) to (AA-34). A divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

［式中、Ｒ及びＲ^aは、前記と同じ意味を表す。］

[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 a crosslinking group. It is a cross-linking group represented by the formulas (XL-1) to (XL-17) of group A.

The "substituted group" 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 amino group, a substituted amino group and an alkenyl group. , Cycloalkenyl group, alkynyl group or cycloalkynyl group. The substituent may be a cross-linking group.

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

The light emitting element of the present invention is a light emitting element having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode, and the first organic layer is a first. A light emitting element, which is a layer containing a composition containing the compound 1 and a first light emitting material, and the second organic layer is a layer containing a crosslinked body of a crosslinked material.

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 the first ink described later.

When the second organic layer is formed by the wet method, it is preferable to use the second ink described later. After forming the second organic layer, the cross-linking material contained in the second organic layer can be cross-linked by heating or irradiating with light, and by heating, the cross-linking contained in the second organic layer can be cross-linked. It is preferable to crosslink the material. When the crosslinked material is contained in the second organic layer in a state of being crosslinked (crosslinked body of the crosslinked material), the second organic layer 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 ° C to 300 ° C, preferably 50 ° C 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 to 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>
Next, the first organic layer included in the light emitting device of the present invention will be described.
The first organic layer is a layer containing the first compound and the first light emitting material. By combining the first compound and the first light emitting material in the first organic layer, it is possible to form the first organic layer without being limited to the method for forming the first organic layer. Become. Further, since the dispersibility and compatibility between the first compound and the first light emitting material are improved, it is considered that the light emitting device has a lower drive voltage than the conventional light emitting device.

[First compound, first luminescent material]
First, the first compound and the first light emitting material contained in the first organic layer will be described.

The maximum peak wavelength of the emission spectrum of the first compound is preferably 300 nm or more and 550 nm or less, more preferably 340 or more and 495 nm or less, still more preferably 380 nm or more and 480 nm or less, and particularly preferably 400 nm or more and 450 nm or less. Is.

The maximum peak wavelength of the emission spectrum of the first light emitting material is 380 nm or more and 570 nm or less, preferably 400 nm or more and 550 nm or less, more preferably 420 or more and 520 nm or less, and further preferably 430 nm or more and 510 nm or less.
Further, the maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first emission material.

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 wt%). Toluene is preferable as the organic solvent for dissolving the compound.

The first compound preferably has at least one function selected from the group consisting of light emitting property, hole injecting property, hole transporting property, electron injecting property and electron transporting property, and has hole injecting property and hole transporting property. It is more preferable to have at least one function selected from the group consisting of sex, electron injection and electron transport.

The first compound is a compound represented by the formula (1A).
The first light emitting material is a compound represented by the formula (1A) or a compound represented by the formula (1B).

[Compound represented by formula (1A)]
n ^1A is preferably an integer of 1 to 7, and more preferably an integer of 1 to 4.

n ^2A is preferably an integer of 0 to 7, more preferably an integer of 0 to 4, still more preferably an integer of 0 to 2, and particularly preferably 0 or 1.

The "aromatic hydrocarbon group of a fused ring in which 3 or more and 10 or less benzene rings are condensed" constitutes a ring from an aromatic hydrocarbon ring in which only 3 or more and 10 or less benzene rings are condensed. It means a group consisting of one or more hydrogen atoms that are directly bonded to a carbon atom.

The aromatic hydrocarbon group of the fused ring in which 3 or more and 10 or less benzene rings are condensed is preferably an aromatic hydrocarbon group of the fused ring in which 3 or 7 or less benzene rings are condensed. More preferably, it is an aromatic hydrocarbon group of a fused ring in which 3 or more and 5 or less benzene rings are condensed, and more preferably, an aromatic hydrocarbon of a fused ring in which 3 or 4 benzene rings are condensed. It is a group, and these groups may have a substituent.

The aromatic hydrocarbon group of the fused ring obtained by condensing 3 or more and 10 or less benzene rings is an anthracene ring, a phenanthren ring, or a ring in which 1 or more and 7 or less benzene rings are condensed on these rings. , Examples of groups excluding one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring, preferably an anthracene ring, a phenanthren ring, or one or more and three or less benzene rings in these rings. It is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the fused ring, and more preferably from an anthracene ring, benzoanthracene ring, phenanthren ring, benzophenanthrene ring, or perylene ring. , A group consisting of one or more hydrogen atoms directly bonded to a carbon atom constituting the ring, more preferably an anthracene ring, a tetraphen ring, a phenylene ring, a triphenylene ring, a naphthacene ring, a pyrene ring, a perylene ring or the like. It is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the anthracene ring, and is particularly preferably from an anthracene ring, tetraphen ring, phenylene tren ring, naphthalcene ring, pyrene ring or chrysen ring. , A group consisting of one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring, and particularly preferably one or more hydrogen atoms directly bonded to the carbon atoms constituting the ring from the anthracene ring or pyrene ring. It is a group excluding.

The ^{number of carbon atoms of the aryl group of the fused ring in R 1A} is usually 7 to 60, preferably 9 to 30, and more preferably 10 to 18, not including the number of carbon atoms of the substituent.

Examples of the aryl group of the fused ring in R ^1A include naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthalene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysen ring, and inden. Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a ring, a fluoranthene ring or a benzofluoranthrene ring, preferably a naphthalene ring, an anthracene ring, a phenanthrene ring or a dihydrophenanthrene ring. , A group consisting of a fluorene ring, a spirobifluorene ring, a pyrene ring, a fluoranthrene ring, or a benzofluoranthrene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, and more preferably a naphthalene ring. , Anthracene ring, phenanthrene ring, fluorene ring, spirobifluorene ring or pyrene ring, excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, more preferably naphthalene ring or anthracene ring. , A group consisting of a phenanthrene ring or a pyrene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, particularly preferably a naphthyl group, and these groups have a substituent. May be good.

The ^{substituent that R 1A} 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, an aryl group or an alkenyl group, particularly preferably an aryl group, these groups further having a substituent. You may be doing it.

The ^{number of carbon atoms of the aryl group in the substituent that R 1A} may have is usually 6 to 60, preferably 6 to 40, more preferably 6 without including the number of carbon atoms of the substituent. ~ 30.

^Examples of the aryl group in the substituent that R 1A may have include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, and a perylene ring. Examples thereof include a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a chrysene ring, an inden ring, a fluorantene ring and a benzofluorantene ring, and a benzene ring, a naphthalene ring and an anthracene ring are preferable. , Phenyl phenyl ring, dihydrophenantren ring, fluorene ring, spirobifluorene ring, pyrene ring, fluorantene ring or benzofluorentene ring, excluding one hydrogen atom directly bonded to the carbon atom constituting the ring. More preferably, one hydrogen atom directly bonded to a carbon atom constituting the ring is removed from the benzene ring, naphthalene ring, anthracene ring, fluorene ring, spirobifluorene ring, fluorantene ring or benzofluorentene ring. It is a group, more preferably a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring, and particularly preferably. A phenyl group, a naphthyl group or a fluorenyl group is preferable, and a phenyl group is particularly preferable, and these groups may further have a substituent.

The ^{number of carbon atoms of the monovalent heterocyclic group in the substituent that R 1A} may have is usually 2 to 60, preferably 3 to 30, not including the number of carbon atoms of the substituent. More preferably, it is 3 to 20.

Examples of the monovalent heterocyclic group in the substituent that R ^1A may have include 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, acridin ring, 9,10-dihydroacridine ring, acridone ring, phenazine ring. And 5,10-dihydrophenazine rings include groups consisting of a ring excluding one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, preferably a pyridine ring, a diazabenzene ring, a triazine ring, or azanaphthalene. From the ring, diazanaphthalene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridin ring or 5,10-dihydrophenazine ring. It is a group consisting of a group excluding one hydrogen atom directly bonded to a carbon atom or a hetero atom constituting the ring, and more preferably a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a carbazole ring, and the like. It is a group formed by removing one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring from the dibenzofuran ring or the dibenzothiophene ring, and these groups may further have a substituent.

Among the ^{substituted amino groups in the substituents that R 1A} may have, the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups are further substituted. It may have a group. The examples and preferred ranges of aryl groups in the substituents of the amino group are the same as the examples and preferred ranges of aryl groups in the substituents that ^{Ar 1 may have.} 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 the substituent which ^{Ar 1 may have.}

The ^{substituent that the substituent that R 1A} may have may further have is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, or a cycloalkoxy group. , Aryloxy group, halogen atom, alkenyl group or cycloalkenyl group, more preferably alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group, alkenyl group or cycloalkenyl group. It is a 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 an aryl group, and these groups further have a substituent. You may.

Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent which the substituent which may be possessed by R ^1A may further possess are respectively possessed by ^{R 1A.} It is the same as the example and preferable range of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent which may be used.

Since R ^1A has a lower drive voltage for the light emitting element of the present invention, it is preferably a group represented by the formulas (1-S1) to (1-S17), and more preferably the formula (1-S17). S1) to the group represented by the formula (1-S8) or the formula (1-S14) to the formula (1-S17), more preferably the formula (1-S1), the formula (1-S2) or the formula. It is a group represented by the formulas (1-S5) to (1-S8), and is particularly preferably the formula (1-S1), the formula (1-S2), the formula (1-S5) or the formula (1-S6). ), And more preferably a group represented by the formula (1-S1) or the formula (1-S2).

［式中、Ｒ^Ｓ１及びＲ^Ｓ２は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基、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、ハロゲン原子、アルケニル基又はシクロアルケニル基を表し、これらの基は置換基を有していてもよい。］

[In the formula, ^RS1 and ^RS2 are independently hydrogen atom, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, halogen atom and alkenyl. It represents a group or a cycloalkenyl group, and these groups may have a substituent. ]

^RS1 is preferably a hydrogen atom, 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 more preferably a hydrogen atom. It is an alkyl group, a cycloalkyl group, an aryl group, an alkenyl group or a cycloalkenyl group, more preferably a hydrogen atom, an alkyl group, an aryl group or an alkenyl group, and particularly preferably a hydrogen atom, an alkyl group, an aryl group or a hydrogen atom. It is an alkenyl group, particularly preferably a hydrogen atom or an aryl group, and these groups may have a substituent.

^RS2 is preferably a hydrogen atom, 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 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. It is particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and particularly preferably an aryl group, and these groups may have a substituent.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in ^RS1 and ^{RS2 are aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that R 1A} may have, respectively. Same as the example and preferred range of substituted amino groups.

The examples and preferred ranges of substituents that R ^S1 and RS ² may have are the same as the examples and preferred ranges of substituents that R ^1A may have further. be.

^{Examples and preferred ranges of aryl groups in substituents that RS1} and ^RS2 may have, monovalent heterocyclic groups and substituted amino groups, respectively, are aryls in substituents that ^{Ar 1 may have.} The same is true for the examples and preferred ranges of groups, monovalent heterocyclic groups and substituted amino groups.

R ^2A is preferably an alkyl group, a cycloalkyl group, a monocyclic 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. More preferably, it is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a monocyclic aryl group, a monovalent heterocyclic group, an alkenyl group or a cycloalkenyl group, and more preferably an alkyl group or a cycloalkyl group. , A monocyclic aryl group, an alkenyl group or a cycloalkenyl group, particularly preferably an alkyl group, a monocyclic aryl group or an alkenyl group, and particularly preferably a monocyclic aryl group. Further, it may have a substituent.

The ^{number of carbon atoms of the aryl group of the monocyclic ring in R 2A} does not include the number of carbon atoms of the substituent and is preferably 6.

As ^{the aryl group of the monocyclic ring in R 2A, a} phenyl group which may have a substituent is preferable.

Examples and preferred ranges of monovalent heterocyclic groups and substituted amino groups in R ^2A are examples and preferred ranges of monovalent heterocyclic groups and substituted amino groups in the substituents that R ^1A may have, respectively. It is the same.

The examples and preferred ranges of substituents that R ^2A may have are the same as the examples and preferred ranges of substituents that R ^1A may have.

Examples and preferred ranges of the aryl group in the substituent that R ^2A may have, the monovalent heterocyclic group and the substituted amino group, respectively, are the aryl group in the substituent that ^{R 1A may have, 1} It is the same as the example and preferable range of the heterocyclic group and the substituted amino group of the valence.

Examples and preferred ranges of the substituents that the substituents that R ^2A may have may further include the substituents that the substituents that R ^1A may have may further have. Same as example and preferred range.

Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent which the substituent which may be possessed by R ^2A may further possess are respectively possessed by ^{R 1A.} It is the same as the example and preferable range of the aryl group, the monovalent heterocyclic group and the substituted amino group in the substituent which may be used.

In the first compound, the compound represented by the formula (1A) preferably has the formula (1A-A1), the formula (1A-A2), and the formula (1A-A2) because the driving voltage of the light emitting element of the present invention is lower. 1A-A3), formula (1A-A4), formula (1A-A5) or compound represented by formula (1A-A6), more preferably formula (1A-A1), formula (1A-A4). , A compound represented by the formula (1A-A5) or the formula (1A-A6), more preferably a compound represented by the formula (1A-A1) or the formula (1A-A5), and particularly preferably. , A compound represented by the formula (1A-A1).

In the first light emitting material, the compound represented by the formula (1A) preferably has the formula (1A-A1), the formula (1A-A2), and the formula (1A-A2) because the driving voltage of the light emitting element of the present invention is lower. (1A-A3), a compound represented by the formula (1A-A4), the formula (1A-A5) or the formula (1A-A6), more preferably the formula (1A-A1), the formula (1A-A4). ), The compound represented by the formula (1A-A5) or the formula (1A-A6), more preferably the compound represented by the formula (1A-A1) or the formula (1A-A5), and particularly preferably. Is a compound represented by the formula (1A-A5).

Examples of the compound represented by the formula (1A) include a compound represented by the following formula.

[Compound represented by formula (1B)]
n ^1B is 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 an integer of 2 to 4.

The ^{number of carbon atoms of the aromatic hydrocarbon group in Ar 1B} is usually 6 to 60, preferably 6 to 40, and more preferably 6 to 30, not including the number of carbon atoms of the substituent.

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 perene ring. Examples thereof include a group consisting of a lilene ring, a chrysene ring, an inden 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. Preferably, it 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 chrysen 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 fluoranthene ring or the acenaftfluoranthrene ring, and more preferably, a benzene ring, a biphenyl ring, a naphthalene ring, or anthracene. A ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring, a fluoranthene ring, a benzofluoranthene ring or an acenaftfluoranthene ring, which are directly bonded to carbon atoms constituting the ring. It is a group excluding one or more hydrogen atoms, and more preferably a benzene ring, a biphenyl ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring, a fluoranthrene ring, and a benzofluoranthrene ring. Alternatively, it is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the acenaftfluoranthene ring, and particularly preferably, a biphenyl ring, a naphthalene ring, a fluorene ring, a pyrene ring, or a perylene. It is a group formed by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from the ring, fluoranthrene ring, benzofluoranthrene ring or acenaftfluoranthrene ring.

When Ar ^1B is an aromatic hydrocarbon group of a fused ring in which 3 or more and 10 or less benzene rings are condensed, R ^1B is an alkyl group, a cycloalkyl group, a monocyclic aryl group, or a monovalent heterocyclic ring. Group, alkoxy group, cycloalkoxy group, aryloxy group, halogen atom, alkenyl group or cycloalkenyl group, more preferably alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, monocyclic aryl group, 1 It is a valent heterocyclic group, an alkenyl group or a cycloalkenyl group, more preferably an alkyl group, a cycloalkyl group, a monocyclic aryl group, an alkenyl group or a cycloalkenyl group, and particularly preferably an alkyl group or a monocyclic group. Is an aryl group or an alkenyl group, particularly preferably an alkyl group or a monocyclic aryl group, and these groups may further have a substituent.

When Ar ^1B is not an aromatic hydrocarbon group of a fused ring in which 3 or more and 10 or less benzene rings are condensed, R ^1B is an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or an alkoxy. A group, a cycloalkoxy group, an aryloxy 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, or a monovalent heterocyclic group. It is 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 aryl group or an alkenyl group, in which these groups are further substituted. It may have a group.

The examples and preferred ranges of monocyclic aryl groups in R ^1B are the same as the examples and preferred ranges of monocyclic aryl groups in ^{R 2A.}

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in R ^{1B are aryl groups in substituents that R 1A} may have, monovalent heterocyclic groups and substituted amino groups, respectively. It is the same as the example and the preferable range of.

The examples and preferred ranges of substituents that R ^1B may have are the same as the examples and preferred ranges of substituents that R ^1A may have.

Examples and preferred ranges of the aryl group in the substituent that R ^1B may have, the monovalent heterocyclic group and the substituted amino group, respectively, are the aryl group in the substituent that ^{R 1A may have, 1} It is the same as the example and preferable range of the heterocyclic group and the substituted amino group of the valence.

Examples and preferred ranges of substituents that R ^1B may have may further include substituents that R ^1A may further possess. Same as example and preferred range.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that the substituents that R ^{1B may have may further have in R 1A, 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 the substituent which may be used.

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 carbon atoms to which they are bonded, but the compound represented by the formula (1B) may be formed. Since the maximum peak wavelength of the emission spectrum is a short wavelength, it is preferable not to form a ring.

Examples of the compound represented by the formula (1B) are as shown below.

The compound represented by the formula (1A) and the compound represented by the formula (1B) are 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, JP-A-2007-291061, JP-A-2007-314506, JP-A-2007-314510, JP-A-2008- It can be synthesized according to the methods described in JP-A-308485, JP-A-2010-120136, JP-A-2010-123917, JP-A-2011-307744, and JP-A-2011-174059.

[Composition ratio of the first organic layer, etc.]
The first organic layer may contain one kind of the first compound alone, or may contain two or more kinds of the first compound. Further, the first organic layer may contain one kind of the first light emitting material alone, or may contain two or more kinds of the first light emitting material.

In the first organic layer, the content of the first light emitting material is usually 0.05 to 80 parts by weight when the total of the first compound and the first light emitting material is 100 parts by weight, and the present invention. Since the driving voltage of the light emitting element is lower, it is preferably 0.1 to 50 parts by weight, more preferably 1 to 30 parts by weight, and further preferably 5 to 15 parts by weight.

[First composition]
The first organic layer is selected from the group consisting of a first compound, a first light emitting material, a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material and an antioxidant. It may be a layer containing a composition containing at least one kind of material (hereinafter, also referred to as "first composition"). However, in the first composition, the light emitting material is different from the first light emitting material. Further, in the first composition, the hole transporting material, the hole injecting material, the light emitting material, the electron transporting material and the electron injecting material are different from the first compound.

[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 weight, preferably 5 when the total of the first compound and the first light emitting material is 100 parts by weight. ~ 150 parts by weight.

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 weight, preferably 5 to 5 parts by weight, when the total of the first compound and the first light emitting material is 100 parts by weight. It is 150 parts by weight.

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 weight, respectively, when the total of the first compound and the first light emitting material is 100 parts by weight. It is preferably 5 to 150 parts by weight.

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.

[Luminescent material]
Luminescent materials are classified into low molecular weight compounds and high molecular weight compounds. The 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 group represented by the formula (X), a carbazolediyl group, a phenoxazinediyl group and a phenothiazinediyl. Examples thereof include high molecular compounds containing a group, an anthracendiyl group, a pyrienyl group and the like.

The luminescent material preferably comprises a triplet luminescent complex and / or a polymeric compound.

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

In the first composition, the blending amount of the light emitting material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight when the total of the first compound and the first light emitting material is 100 parts by weight. It is a part by weight.

The luminescent 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 compound and the first light emitting material and does not inhibit light emission and charge transport, and may be, for example, a phenolic antioxidant or a phosphorus antioxidant. Can be mentioned.

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

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

[First ink]
The composition containing the first compound, the first light emitting material, and the solvent (hereinafter, also referred to as "first ink") includes a spin coating method, a casting method, a microgravia coating method, and a gravure coating method. , Bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc. Can be suitably used for.

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-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonan, 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 100 to 10000 parts by weight, preferably 2000 to 20000 parts by weight, when the total of the first compound and the first light emitting material is 100 parts by weight. Is.

<Second organic layer>
The second organic layer is a layer containing a crosslinked body of a crosslinking material. Since the crosslinked material is contained in the second organic layer in a crosslinked state, the second organic layer is substantially insoluble in the solvent. Therefore, when the organic layer is formed on the second organic layer by a wet method, the second organic layer is less likely to be eroded by the solvent, and its original function is fully exhibited. Further, the film forming property of the organic layer formed on the second organic layer is improved, and the organic layer having excellent thickness uniformity and surface smoothness is formed.

[Crosslinking material]
The crosslinked body of the crosslinked material is obtained by making the crosslinked material in a crosslinked state by the above-mentioned method, conditions and the like.

The cross-linking material may be a low molecular weight compound or a high molecular weight compound, but has at least one cross-linking group selected from the cross-linking group A group because the driving voltage of the light emitting element of the present invention is lower. A low molecular weight compound (hereinafter, also referred to as “low molecular weight compound of the second organic layer”) or a high molecular weight compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group (hereinafter, also referred to as “low molecular weight compound”). It is also preferably a "polymer compound of the second organic layer"), and more preferably a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. ..

As the cross-linking group selected from the cross-linking group A group, the driving voltage of the light emitting element of the present invention is lower, so that the formulas (XL-1) to (XL-4) and the formulas (XL-7) to are preferable. It is a cross-linking group represented by the formula (XL-10) or the formulas (XL-14) to (XL-17), and more preferably, the formula (XL-1), the formula (XL-3), and the formula (XL). -9), a cross-linking group represented by the formula (XL-10), the formula (XL-16) or the formula (XL-17), more preferably the formula (XL-1), the formula (XL-16). Alternatively, it is a cross-linking group represented by the formula (XL-17), particularly preferably a cross-linking group represented by the formula (XL-1) or the formula (XL-17), and particularly preferably a cross-linking group represented by the formula (XL-). It is a cross-linking group represented by 17).

[Polymer compound of the second organic layer]
The structural unit having at least one cross-linking group selected from the cross-linking group A group contained in the polymer compound of the second organic layer is a structural unit represented by the formula (2) described later or the formula (2'). It is preferably a structural unit represented, but it may be a structural unit represented below.

[Constituent unit represented by equation (2)]
nA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 1 or 2, because the drive voltage of the light emitting element of the present invention is lower.

n is preferably 2 because the drive voltage of the light emitting element of the present invention is lower.

Ar ³ is an aromatic hydrocarbon group which may have a substituent because the driving voltage of the light emitting element of the present invention is lower.

The ^{number of carbon atoms of the aromatic hydrocarbon group represented by Ar 3} is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, 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 3} is preferably a group represented by the formulas (A-1) to (A-20). More preferably, a group represented by the formula (A-1), the formula (A-2), the formula (A-6) to the formula (A-10), the formula (A-19) or the formula (A-20). More preferably, it is 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 are the groups. The group of may have a substituent.

The ^{number of carbon atoms of the heterocyclic group represented by Ar 3} 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 3} 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 3} 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.

Alkylene group represented by L ^A is not including the carbon atom number of substituent is usually 1 to 20, preferably 1 to 15, more preferably 1 to 10. Cycloalkylene group represented by L ^A is not including the carbon atom number of substituent is usually 3 to 20.
The alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group and an octylene group.

Alkylene group and cycloalkylene group represented by L ^A may have a substituent.
As the substituent which the alkylene group and the cycloalkylene group may have, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group are preferable, and these groups further have a substituent. May be.

Arylene group represented by L ^A 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, and these groups may further have substituents.

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

L ^A, since the preparation of the polymer compound of the second organic layer becomes easier, preferably, an arylene group or an alkylene group, more preferably a phenylene group, fluorenediyl group or an alkylene group, these The group of may have a substituent.

As the cross-linking group represented by X, the driving voltage of the light emitting element of the present invention is lower, so that the formulas (XL-1) to (XL-4) and the formulas (XL-7) to (XL-7) are preferable. XL-10) or a cross-linking group represented by the formulas (XL-14) to (XL-17), more preferably the formula (XL-1), the formula (XL-3), the formula (XL-9). ), Formula (XL-10), formula (XL-16) or formula (XL-17), more preferably formula (XL-1), formula (XL-16) or formula. It is a cross-linking group represented by (XL-17), particularly preferably a cross-linking group represented by the formula (XL-1) or the formula (XL-17), and particularly preferably a cross-linking group represented by the formula (XL-17). It is a cross-linking group represented by.

Since the structural unit represented by the formula (2) is excellent in stability and crosslinkability of the polymer compound of the second organic layer, it is relative to the total amount of the structural units contained in the polymer compound of the second organic layer. It is preferably 0.5 to 90 mol%, more preferably 3 to 75 mol%, and further preferably 5 to 60 mol%.

The structural unit represented by the formula (2) may be contained in only one kind or two or more kinds in the polymer compound of the second organic layer.

[Constituent unit represented by equation (2')]
mA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0, because the drive voltage of the light emitting element of the present invention is lower. It is 0.

m is preferably 1 or 2, and more preferably 2 because the drive voltage of the light emitting element of the present invention is lower.

c is preferably 0 because the production of the polymer compound of the second organic layer becomes easy and the driving voltage of the light emitting element of the present invention becomes lower.

Ar ⁵ is an aromatic hydrocarbon group which may have a substituent because the driving voltage of the light emitting element of the present invention is lower.

The definition and example of the arylene group portion excluding the m substituents of the aromatic hydrocarbon group represented by Ar ⁵ are the same as the definition and example of the arylene group represented by ^{Ar X 2 in the formula (X) described later.} Is.

The definition and example of the divalent heterocyclic group portion excluding the m substituents of the heterocyclic group represented by Ar ⁵ are the divalent heterocyclic group represented by ^{Ar X 2 in the formula (X) described later.} It is the same as the definition and example of the part.

Definitions and examples of divalent groups excluding the m substituents of the group in which at least one aromatic hydrocarbon ring represented by Ar ^{5 and at least one heterocyclic ring are directly bonded are described in the formula described later (} 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 in X).

Ar ⁴ and Ar ⁶ are arylene groups which may have a substituent because the driving voltage of the light emitting device of the present invention is lower.

The definitions and examples of the arylene groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the arylene groups represented by ^{Ar X 1} and Ar ^{X 3 in the formula (X) described later.}

The definitions and examples of the divalent heterocyclic groups represented by Ar ⁴ and Ar ⁶ are the same as the definitions and examples of the divalent heterocyclic groups represented by ^{Ar X 1} and Ar ^{X 3 in the formula (X) described later.} be.

The ^{groups represented by Ar 4} , Ar ⁵ and Ar ⁶ 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. Halogen atoms, monovalent heterocyclic groups and cyano groups are preferred.

Alkylene group represented by K ^A, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by L ^A, a cycloalkylene group, an arylene group, a divalent heterocyclic It is the same as the definition and example of the ring group.

K ^A, since production of the polymer compound of the second organic layer becomes easy, it is preferable that a phenylene group or a methylene group.

The definition and example of the cross-linking group represented by X'are the same as the definition and example of the cross-linking group represented by X described above.

The structural unit represented by the formula (2') 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, so that the second organic 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 layer.

The structural unit represented by the formula (2') may be contained in only one kind or two or more kinds in the polymer compound of the second organic layer.

[Preferable embodiment of the structural unit represented by the formula (2) or (2')]
Examples of the structural unit represented by the equation (2) include the structural units represented by the equations (2-1) to (2-30), and the structural units represented by the equation (2') include. For example, the building blocks represented by the equations (2'-1) to (2'-9) can be mentioned. 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) ~ Configuration represented by Eq. (2-15), Eq. (2-19), Eq. (2-20), Eq. (2-23), Eq. (2-25) or Eq. (2-30) It is a unit, and more preferably a structural unit represented by Eq. (2-1) to Eq. (2-9), Eq. (2-20), Eq. (2-22) or Eq. (2-30).

[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 of the present invention is lower.

Since the polymer compound of the second organic layer has excellent hole transportability and the driving voltage of the light emitting device of the present invention is lower, the structural unit represented by the formula (X) and the formula (Y) are further expressed. ) Is preferably included.

［式中、
ａ^X1及びａ^X2は、それぞれ独立に、０以上の整数を表す。
Ａｒ^X1及びＡｒ^X3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^X2及びＡｒ^X4は、それぞれ独立に、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。Ａｒ^X2及びＡｒ^X4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。
Ｒ^X1、Ｒ^X2及びＲ^X3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は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。Ｒ^X2及びＲ^X3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。］

[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. If there are multiple Ar ^X2 and Ar ^X4 , they may be the same or different.
R ^X1 , R ^{X 2} and R ^{X 3} each 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. If there are multiple R ^X2 and R ^{X 3} , they may be the same or different. ]

Since the drive voltage of the light emitting element of the present invention is lower, ^{a X1 is preferably an integer of 2 or less, and more preferably 1.}

Since the drive voltage of the light emitting element of the present invention is lower, ^{a X2 is preferably an integer of 2 or less, and more preferably 0.}

R ^X1 , R ^{X 2} and R ^{X 3} are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be good.

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

The ^{divalent heterocyclic group represented by Ar X1} and Ar ^X3 is more preferably represented by the formula (AA-1), the formula (AA-2) or the formulas (AA-7) to (AA-26). 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 more preferably the formula (A-1), the formula (A-6), the formula (A-7), the formula (A-9) to the formula (A-11). Alternatively, it is a group represented by the formula (A-19), and these groups may have a substituent.

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

A more preferable range of an arylene group and a divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^{X4 and at least one divalent heterocyclic group are directly bonded.} The more preferable range is the same as the more preferable range and the further 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.

［式中、Ｒ^XXは、水素原子、アルキル基、シクロアルキル基、アリール基又は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。］

[In the formula, R ^XX 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. ]

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

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

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

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 equations (X-3) to (X-6).

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

[In the formula, R ^X4 and R ^X5 are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, halogen atom, monovalent heterocyclic group or cyano. Representing groups, these groups may have substituents. A plurality of R ^X4s may be the same or different. A plurality of R ^X5s existing may be the same or different, and adjacent R ^X5s 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 90 mol% with respect to the total amount of the structural units contained in the polymer compound of the second organic layer. , More preferably 1 to 70 mol%, still more preferably 10 to 50 mol%.

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

In the polymer compound of the second organic layer, the structural unit represented by the formula (X) may contain only one kind or two or more kinds.

［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。］

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

The ^{divalent heterocyclic group represented by Ar Y1} is more 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), and particularly preferably represented by the formula (AA-4), the formula (AA-10), the formula (AA-18) or the formula (AA-20). It is a group, and these groups may have a substituent.

A more preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar ^{Y1 and at least one divalent heterocyclic group are directly bonded, further preferable.} The range is the same as the more preferable range and the more preferable range of the arylene group and the divalent heterocyclic group represented by ^{Ar Y1 described above, respectively.}

As a divalent group in which at least one arylene group represented by ^{Ar Y1 and at least one divalent heterocyclic group are directly bonded, at least Ar X 2} and Ar ^{X 4} represented by the formula (X) are represented. 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, and 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 from the viewpoint of the drive voltage of the light emitting element of the present invention. It is a structural unit represented by the formula (Y-1) or the formula (Y-2), and is preferably the formula (Y-3) from the viewpoint of the electron transportability of the polymer compound of the second organic layer. ) Or the structural unit represented by the formula (Y-4), and preferably from the viewpoint of the hole transport property of the polymer compound of the second organic layer, the formulas (Y-5) to (Y-7) are preferable. ) Is a structural unit.

［式中、Ｒ^Y1は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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^Y1は、同一でも異なっていてもよく、隣接するＲ^Y1同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[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 atoms to which they are bonded. ]

^RY1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

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

［式中、Ｒ^Y11は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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^Y11は、同一でも異なっていてもよい。］

[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, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

［式中、
Ｒ^Y1は前記と同じ意味を表す。
Ｘ^Y1は、−Ｃ(Ｒ^Y2)₂−、−Ｃ(Ｒ^Y2)＝Ｃ(Ｒ^Y2)−又は−Ｃ(Ｒ^Y2)₂−Ｃ(Ｒ^Y2)₂−で表される基を表す。Ｒ^Y2は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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^Y2は、同一でも異なっていてもよく、Ｒ^Y2同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[During the ceremony,
^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 they 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 A ring group, or one of which is an alkyl or cycloalkyl group and the other of which is an aryl or monovalent heterocyclic group, more preferably one of which is an alkyl or cycloalkyl group and the other of which is an aryl group. May have a substituent. The two existing ^RY2s may be bonded to each other to form a ring with the atoms to which they are bonded, and when ^RY2 forms a ring, it is represented by ^{−C (RY2} ) _{2 −.} Is preferably a group represented by the formulas (Y-A1) to (Y-A5), more preferably a group represented by the formula (Y-A4), and these groups have a substituent. You may be doing it.

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 may be a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

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 groups represented are preferably groups represented by the formulas (Y-B1) to (Y-B5), more preferably groups represented by the formula (Y-B3), and these groups are represented by the formulas (Y-B3). It may have a substituent.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

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

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

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

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

［式中、
Ｒ^Y1は前記と同じ意味を表す。
Ｒ^Y3は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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。

[During the ceremony,
^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, more preferably an aryl group, and these groups have a substituent. May be.

［式中、
Ｒ^Y1は前記を同じ意味を表す。
Ｒ^Y4は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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。

[During the ceremony,
^RY1 has the same meaning as 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, more preferably an aryl group, and these groups have a substituent. May be.

Examples of the structural unit represented by the formula (Y) include the structural units represented by the formulas (Y-11) to the formula (Y-56), and the structural units represented by the formulas (Y-11) to the formula (Y-11) 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 is included in the polymer compound of the second organic layer because the driving voltage of the light emitting element of the present invention is lower. It is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of the constituent units.

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 0.5 to 0.5 with respect to the total amount of the structural units contained in the polymer compound of the second organic layer. It is 40 mol%, more preferably 3 to 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 compound of the second organic layer.

Examples of the polymer compound of the second organic layer include the polymer compounds P-1 to P-8 shown in Table 1. Here, the “other structural unit” means a structural unit other than the structural unit represented by the equation (2), the equation (2'), the equation (X), and the equation (Y).

［表中、ｐ’、ｑ’、ｒ’、ｓ’及びｔ’は、各構成単位のモル比率を表す。ｐ’＋ｑ’＋ｒ’＋ｓ’＋ｔ’＝100であり、且つ、70≦ｐ’＋ｑ’＋ｒ’＋ｓ’≦100である。］

[In the table, p', q', r', s'and t'represent the molar ratio of each structural unit. p'+ q'+ r'+ s'+ t'= 100, and 70 ≦ p'+ q'+ r'+ s'≦ 100. ]

Examples and preferable ranges of the structural units represented by the formulas (2), (2'), formulas (X) and formulas (Y) in the polymer compounds P-1 to P-8 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 polystyrene-equivalent number average molecular weight of the polymer compound of the second organic layer is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ^{4 to} 5 × 10 ⁵ , and 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 using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc., and Suzuki. Examples thereof include a method of polymerizing by a coupling reaction using a transition metal catalyst such as a reaction, a Yamamoto reaction, a Buchwald reaction, a Stille 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 compound of the second organic layer 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.

[Low molecular weight compound of the second organic layer]
As the low molecular weight compound of the second organic layer, the low molecular weight compound represented by the formula (3) is preferable.

m ^B1 is usually an integer of 0 to 10, and is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, and even more preferably 0 or 0, because it facilitates the synthesis of the crosslinked material. It is 1, and particularly preferably 0.

m ^B2 is usually an integer of 0 to 10, and is preferably an integer of 0 to 5, because it facilitates the synthesis of the cross-linking material and the drive voltage of the light emitting element of the present invention is lower. Is an integer of 0 to 3, more preferably 1 or 2, and particularly preferably 1.

m ^B3 is usually an integer of 0 to 5, and is preferably an integer of 0 to 4, more preferably an integer of 0 to 2, and even more preferably 0, because it facilitates the synthesis of the crosslinked material. be.

Definition and examples of the arylene group part excluding the m ^B3 substituents of the aromatic hydrocarbon group represented by Ar ⁷ has a definition and examples of the arylene group represented by Ar ^X2 in the formula (X) described above It is the same.

The definition and example of the divalent heterocyclic group portion excluding the ^mb3 substituents of the heterocyclic group represented by Ar ⁷ are the divalent heterocyclic ring represented by ^{Ar X 2 in the above formula (X).} Same as the definition and example of the base part.

The definition and example of a divalent group excluding the ^mb3 substituent of the group in which at least one aromatic hydrocarbon ring represented by Ar ⁷ and at least one heterocyclic ring are directly bonded are described in the above formula. 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 in (X).

The definitions and examples of the substituents that the group represented by Ar ⁷ may have are the same as the definitions and examples of the substituents that the group represented by ^{Ar X 2 may have in the above formula (X).} be.

Ar ⁷ is preferably an aromatic hydrocarbon group because the driving voltage of the light emitting element of the present invention is low, and this aromatic hydrocarbon group may have a substituent.

Alkylene group represented by L ^B1, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by the above-mentioned L ^A, a cycloalkylene group, an arylene group, a divalent It is the same as the definition and example of the heterocyclic group of.

Since ^LB1 facilitates the synthesis of the cross-linking material, it is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an arylene group, and further preferably a phenylene group, a fluoreneyl group or It is an alkylene group, particularly preferably a phenylene group or an alkylene group, and these groups may have a substituent.

X'' is preferably a bridging group, an aryl group or a monovalent heterocyclic group represented by any of the formulas (XL-1) to (XL-17), and more preferably the formula (XL). -1), a cross-linking group represented by the formula (XL-3), the formula (XL-7) to the formula (XL-10), the formula (XL-16) or the formula (XL-17), or an aryl group. Yes, more preferably a cross-linking group represented by the formula (XL-1), the formula (XL-16) or the formula (XL-17), a phenyl group, a naphthyl group or a fluorenyl group, and particularly preferably the formula ( It is a cross-linking group represented by XL-16) or formula (XL-17), a phenyl group or a naphthyl group, and particularly preferably a cross-linking group represented by formula (XL-16) or a naphthyl group. These groups may have substituents.

Examples of the cross-linking material include low molecular weight compounds represented by the formulas (3-1) to (3-16), preferably represented by the formulas (3-1) to (3-10). It is a low molecular weight compound, and more preferably a low molecular weight compound represented by the formulas (3-5) to (3-9).

The low molecular weight compounds of the second organic layer are Aldrich, Luminesis Technology Corp. , American Dye Source, etc. In addition, for example, it can be synthesized according to the methods described in International Publication No. 1997/033193, International Publication No. 2005/0352221, and International Publication No. 2005/049548.

In the second organic layer, the crosslinked body of the crosslinking material may be contained alone or in combination of two or more.

[Second composition]
The second organic layer comprises a crosslinked body of a crosslinked material and at least one material selected from the group consisting of a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material and an antioxidant. It may be a layer containing a composition containing (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 luminescent material contained in the second composition are the hole transporting materials contained in the first composition. , Examples and preferred ranges of electron transport materials, hole injection materials, electron injection materials and luminescent materials. 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 usually 1 when the crosslinked body of the crosslinked material is 100 parts by weight. It is ~ 400 parts by weight, preferably 5 to 150 parts by weight.

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 weight when the crosslinked body of the crosslinked material is 100 parts by weight.

[Second ink]
The second composition containing the cross-linking material and the solvent (hereinafter, also referred to as “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 10000 parts by weight, preferably 2000 to 20000 parts by weight, when the crosslinked material is 100 parts by weight.

<Layer structure of light emitting element>
The light emitting device of the present invention may have a layer other than the anode, the cathode, the first organic layer and the second organic layer.

In the light emitting device of the present invention, the first organic layer is usually a light emitting layer (hereinafter referred to as "first light emitting layer").
In the light emitting device of the present invention, the second organic layer is usually a hole transport layer, a second light emitting layer or an electron transport layer, preferably a hole transport layer or a second light emitting layer, and more preferably. Is a hole transport layer.

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

In the light emitting device of the present invention, 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 of the present invention is lower, so that the anode and the light emitting device It is preferable to further have a hole injection layer between the second organic layer and the second organic layer. 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 device of the present invention is lower, so that the cathode and the first organic layer are formed. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer between the two.

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

In the light emitting device of the present invention, 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 device of the present invention is lower, so that the anode 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 and 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 of the present invention is lower, so that the cathode and the second organic layer are formed. It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer between the layers.

In the light emitting device of the present invention, 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 of the present invention is lower, so that the anode and the first 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 1. 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 device of the present invention is lower, so that the cathode and the second organic layer are used. It is preferable to further have an electron injection layer between the two.

Specific layer configurations of the light emitting device of the present invention include, for example, the layer configurations represented by the following (d1) to (d15). The light emitting device of the present invention 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 of the present invention 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 of the present invention, 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 as needed. May be good.
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 of the present invention, the order, number, and thickness of the layers to be laminated may be adjusted in consideration of the driving voltage 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 of the present invention 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 organic layer. Is preferable.

[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 of the present invention has a hole transport layer and the above-mentioned second light emitting layer and the later electron transport layer are not the second organic layer, the hole transport layer is the second organic layer. It is preferable to have.

[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 of the present invention, 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 of the present invention, a low molecular weight compound is used as a method for forming each layer such as 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. In the case, for example, a vacuum vapor deposition method from a powder, a method by forming a film from a solution or a molten state can be mentioned, and when a polymer compound is used, 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.

In a preferred embodiment, the method for manufacturing a light emitting element of the present invention includes a step of forming a second organic layer between an anode and a cathode by a wet method, and a step of cross-linking the formed second organic layer. It includes a step of forming an organic layer on a crosslinked second organic layer by a wet method. The second organic layer is formed on, for example, an anode or an organic layer such as a hole transport layer and a hole injection layer. The organic layer formed on the second organic layer may be the first organic layer, or may be an organic layer such as an electron transport layer, a hole injection layer, and a second light emitting layer.

[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 one of the following size exclusion chromatography (SEC) using tetrahydrofuran as the mobile phase. Asked by. The measurement conditions of SEC are as follows.

The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 μL was injected into SEC. The mobile phase was run 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.

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

TLC-MS was measured by the following method.
The measurement sample is dissolved in any solvent of toluene, tetrahydrofuran or chloroform at an arbitrary concentration, coated on a TLC plate for DART (manufactured by Techno Applications, trade name: YSK5-100), and coated on TLC-MS (JEOL Ltd.). Manufactured by, trade name: JMS-T100TD (The AccuTOF TLC) was used for measurement. The helium gas temperature at the time of measurement was adjusted in the range of 200 to 400 ° C.

NMR was measured by the following method.
About 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran, deuterated dimethylsulfoxide, deuterated acetone, deuterated N, N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol Alternatively, it was dissolved in deuterated methylene chloride and measured using an NMR apparatus (manufactured by Agent, trade name: INOVA300 or MERCURY 400VX).

The value of high performance liquid chromatography (HPLC) area percentage was used as an index of the purity of the compound. Unless otherwise specified, this value is a value at UV = 254 nm by HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2% by weight, and 1 to 10 μL was injected into HPLC depending on the concentration. For the mobile phase of HPLC, the ratio of acetonitrile / tetrahydrofuran was changed from 100/0 to 0/100 (volume ratio), and the flow was carried out at a flow rate of 1.0 mL / min. As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance was used. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as the detector.

In this example, the maximum peak wavelength of the emission spectrum of the compound was measured at room temperature by a spectrophotometer (manufactured by JASCO Corporation, 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.

<Synthesis Example HM1> Synthesis of Compounds HM-1 to HM-6 and Obtained 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 International Publication No. 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.

<Synthetic Example EM1> The synthetic compound EM-1 of the compounds EM-1 to EM-8 and EM-A1 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 was 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-A1 was synthesized according to the method described in JP-A-2011-105643.

<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 atmosphere, specially Compound EM-9b (9.00 g), tetrakis (triphenylphosphine) palladium (0) (0.294 g), 20 wt% tetrabutylammonium hydroxide aqueous solution (18) synthesized according to the method described in Japanese Patent Publication No. 2015-110751. .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-A1 was 454 nm.

<Synthesis Example M1> Synthesis of Compounds M3 to M9 Compound M3 was synthesized according to the method described in International Publication No. 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.
Compounds M6 and M7 were synthesized according to the method described in International Publication No. 2002/045184.
Compound M8 was synthesized according to the method described in International Publication No. 2011/049241.
Compound M9 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 using Compound M6 and Compound M7 according to the method described in JP2012-36381.

The number average molecular weight and weight-average molecular weight in terms of polystyrene of the polymer compound HTL-1, respectively, were Mn = 8.1 × 10 ⁴ and Mw = 3.4 × 10 ^5.

According to the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-1 is composed of the structural unit derived from the compound M6 and the structural unit derived from the compound M7 in a molar ratio of 50:50. Is a copolymer.

<Synthesis example HTL2> Synthesis of polymer compound HTL-2

The polymer compound HTL-2 was synthesized using the compound M5 and the compound M9 according to the method described in International Publication No. 2015/194448.

The number average molecular weight and weight-average molecular weight in terms of polystyrene of the polymer compound HTL-2, respectively, were Mn = 4.5 × 10 ⁴ and Mw = 1.5 × 10 ^5.

According to the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-2 is composed of the structural unit derived from the compound M5 and the structural unit derived from the compound M9 in a molar ratio of 50:50. Is a copolymer.

<Synthesis Example HTL3> Synthesis of Polymer Compound HTL-3 The polymer compound HTL-3 was synthesized using the compound M6, the compound M7 and the compound M8 according to the method described in International Publication No. 2011/049241.

The number average molecular weight and weight-average molecular weight in terms of polystyrene of the polymer compound HTL-3, respectively, were Mn = 8.9 × 10 ⁴ and Mw = 4.2 × 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 M6, a structural unit derived from the compound M7, and a structural unit derived from the compound M8. It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.

<Synthesis Example HTL4> Synthesis of Polymer Compound HTL-4 Polymer Compound 2 was synthesized using Compound M3, Compound M4 and Compound M5 according to the method described in International Publication No. 2015/145871.

The number average molecular weight and weight-average molecular weight in terms of polystyrene of the polymer compound HTL-4, respectively, were Mn = 2.3 × 10 ⁴ and Mw = 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.

<Obtaining low molecular weight compound HTM-1>
The low molecular weight compound HTM-1 was purchased from Luminesecense Technology.

<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 with 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 weight. 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 to obtain a second film. 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 weight / 8.5% by weight) were dissolved in toluene at a concentration of 2% by weight. Using the obtained toluene solution, a film was formed on the second organic layer to a thickness of 60 nm by a spin coating method, and heated at 150 ° C. for 10 minutes on a hot plate 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 by 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> Fabrication 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 element D15 In Example D1 (formation of a second organic layer), "the polymer compound HTL-4 was dissolved in xylene at a concentration of 0.6% by weight". Instead, the light emitting element D15 was produced in the same manner as in Example D1 except that "Compound HTM-1 was dissolved in chlorobenzene at a concentration of 0.9% by weight."

EL light emission was observed by applying a voltage to the light emitting element D15. The drive voltage at 400 cd / m ² was 5.8 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.16).

<Example D16> Fabrication and evaluation of light emitting device D16 A light emitting device D16 was manufactured in the same manner as in Example D15 except that compound EM-3 was used instead of compound EM-2 in Example D15.

EL light emission was observed by applying a voltage to the light emitting element D16. The drive voltage at 400 cd / m ² was 6.5 V and the CIE chromaticity coordinates (x, y) were (0.16, 0.12).

<Example D17> Fabrication and evaluation of light emitting device D17 A light emitting device D17 was manufactured in the same manner as in Example D15 except that compound EM-9 was used instead of compound EM-2 in Example D15.

EL light emission was observed by applying a voltage to the light emitting element D17. The drive voltage at 400 cd / m ² was 6.4 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.15).

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

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).

<Example D18> Fabrication and evaluation of light emitting device D18 A light emitting device D18 is used in the same manner as in Example D1 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D1. Made.

EL light emission was observed by applying a voltage to the light emitting element D18. The drive voltage at 3000 cd / m ² was 8.0 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.17). The drive voltage at 5000 cd / m ² was 9.3 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.17).

<Example D19> Fabrication and evaluation of light emitting device D19 A light emitting device D19 is used in the same manner as in Example D2 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D2. Made.

EL light emission was observed by applying a voltage to the light emitting element D19. The drive voltage at 3000 cd / m ² was 8.1 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.16). The drive voltage at 5000 cd / m ² was 9.5 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.16).

<Example D20> Fabrication and evaluation of light emitting device D20 A light emitting device D20 is used in the same manner as in Example D2 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D8. Made.

EL light emission was observed by applying a voltage to the light emitting element D20. The drive voltage at 3000 cd / m ² was 7.0 V and the CIE chromaticity coordinates (x, y) were (0.22, 0.48). The drive voltage at 5000 cd / m ² was 7.9 V and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).

<Example D21> Fabrication and evaluation of light emitting device D21 The light emitting device D21 is used in the same manner as in Example D17 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D17. Made.

EL light emission was observed by applying a voltage to the light emitting element D21. The drive voltage at 3000 cd / m ² was 8.5 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.12). The drive voltage at 5000 cd / m ² was 10.1 V and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).

<Example D22> Fabrication and evaluation of light emitting device D22 The light emitting device D22 is used in the same manner as in Example D13 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D13. Made.

EL light emission was observed by applying a voltage to the light emitting element D22. The drive voltage at 3000 cd / m ² was 8.2 V, and the CIE chromaticity coordinates (x, y) were (0.21, 0.43). The drive voltage at 5000 cd / m ² was 9.5 V and the CIE chromaticity coordinates (x, y) were (0.22, 0.48).

<Comparative Example CD2> Preparation and Evaluation of Light Emitting Element CD2 A light emitting device CD2 was produced in the same manner as in Example D12 except that compound EM-A1 was used instead of compound EM-2 in Example D12.

EL light emission was observed by applying a voltage to the light emitting element CD2. The drive voltage at 3000 cd / m ² was 9.0 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.13). The drive voltage at 5000 cd / m ² was 11.1 V and the CIE chromaticity coordinates (x, y) were (0.15, 0.13).

<Comparative Example CD3> Fabrication and Evaluation of Light Emitting Element CD3 The light emitting element CD3 is used in the same manner as in Example D1 except that the polymer compound HTL-1 is used instead of the polymer compound HTL-4 in Example D1. Made.

EL light emission was observed by applying a voltage to the light emitting element CD3. The drive voltage at 3000 cd / m ² was 11.0 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.13). Moreover, although the voltage was applied up to 12V, it did not reach ^{5000 cd / m 2.}

<Example D23> Fabrication and evaluation of light emitting element D23 The light emitting element D23 is used in the same manner as in Example D2 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D2. Made.

EL light emission was observed by applying a voltage to the light emitting element D23. The drive voltage at 100 cd / m ² was 4.6 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.17). The drive voltage at 200 cd / m ² was 5.0 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.15).

<Comparative Example CD4> Preparation and Evaluation of Light Emitting Element CD4 A light emitting element CD4 was produced in the same manner as in Example D23 except that compound HM-1 was used instead of compound HM-2 in Example D23.

EL light emission was observed by applying a voltage to the light emitting element CD4. The drive voltage at 100 cd / m ² was 10.6 V, and the CIE chromaticity coordinates (x, y) were (0.19, 0.17). Moreover, although the voltage was applied up to 12V, it did not reach ^{200cd / m 2.}

Claims (10)

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 composition containing the first compound and the first light emitting material.
The maximum peak wavelength of the emission spectrum of the first light emitting material is 380 nm or more and 570 nm or less.
The maximum peak wavelength of the emission spectrum of the first compound is shorter than the maximum peak wavelength of the emission spectrum of the first emission material.
The first compound is a compound represented by the formula (1A).
The first light emitting material is a compound represented by the formula (1B).
A light emitting device in which the second organic layer is a layer containing a crosslinked body of a crosslinked material having only one type of crosslinked group.

[During the ceremony,
n ^1A represents an integer of 1 or more and 10 or less.
n ^2A represents an integer of 0 or more and 10 or less.
Ar ^1A represents an aromatic hydrocarbon group of a fused ring in which 3 or more and 10 or less benzene rings are condensed.
R ^1A represents an aryl group of the fused ring, which group may have a substituent. When ^{there are a plurality of R 1A} , they may be the same or different.
R ^2A is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, a monocyclic aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, and an alkynyl group. Alternatively, it represents a cycloalkynyl group, and these groups may have a substituent. When ^{there are a plurality of R 2A} , they may be the same or different.
]

[During the ceremony,
n ^1B represents an integer of 0 or more and 10 or less.
Ar ^1B represents a group consisting of a fluoranthene ring, a benzofluoranthene ring or an acenaftfluoranthene ring excluding one or more hydrogen atoms directly bonded to a carbon atom constituting the ring.
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 carbon atoms to which they are bonded. ] The cross-linking material
The first aspect of the present invention, which is a low molecular weight compound having one kind of cross-linking group selected from the group A of the cross-linking group, or a high molecular compound containing a cross-linking structural unit having one kind of cross-linking group selected from the group A of the cross-linking group. Light emitting element.
(Crosslink 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. ] The light emitting element according to claim 2, wherein the cross-linking material is a polymer compound containing a cross-linking structural unit having one kind of cross-linking group selected from the cross-linking group A group. The light emitting device according to claim 3, wherein the cross-linked structural unit is a structural unit represented by the formula (2) or a structural unit represented by the formula (2').

[During the ceremony,
nA represents an integer from 0 to 5, and n represents 1 or 2. When there are a plurality of nA, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -NR '- represents a group represented by an oxygen atom or a sulfur atom in these groups have a substituent May be good. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A is plurally present, they may be the same or different.
X represents a cross-linking group selected from the group A of cross-linking groups. ]

[During the ceremony,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. If there are multiple mAs, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocycle are directly bonded, and these groups have a substituent. May be.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ 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.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent May be good. R'represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If K ^A there are a plurality, they may be the same or different.
X'is a cross-linking group selected from the group A of cross-linking groups, a hydrogen atom, an alkyl group, a cycloalkyl group,
It represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If there are multiple X's, they may be the same or different. However, at least one X'is a cross-linking group selected from the group A of cross-linking groups. ] The light emitting device according to claim 1, wherein the crosslinked material is a low molecular weight compound represented by the formula (3).

[During the ceremony,
m ^{B 1} , m ^{B 2} and m ^{B 3} each independently represent an integer greater than or equal to 0. A plurality of m ^{B 1s} may be the same or different. If there are multiple m ^{B 3} , they may be the same or different.
Ar ⁷ 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. If Ar ⁷ there are a plurality, they may be the same or different.
^LB1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N (R''')-, an oxygen atom or a sulfur atom, and these groups are substituents. May have. 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 there are multiple LB 1} , they may be the same or different.
X'' represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of X''s may be the same or different. However, at least one of the plurality of X''s present is a cross-linking group. ] The Ar ^1A is an anthracene ring, a phenanthrene ring, or a ring in which one or more and seven or less benzene rings are condensed with these rings, except for one or more hydrogen atoms directly bonded to carbon atoms constituting the ring. The light emitting element according to any one of claims 1 to 5, which is a base thereof. The compound represented by the formula (1A) is a formula (1A-A1), a formula (1A-A2), a formula (1A-A3), a formula (1A-A4), a formula (1A-A5) or a formula (1A). The light emitting element according to any one of claims 1 to 6, which is a compound represented by −A6).

The R ^1A is 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, an inden ring, a fluoranthene ring or a benzofluorane ring. One of claims 1 to 7, which is a group formed by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from the fluorene ring (the group may have a substituent). The light emitting element according to. The light emitting device according to any one of claims 1 to 8, 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 9, wherein the second organic layer is a layer provided between the anode and the first organic layer.