JP7033397B2 - 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 light emission 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 fluorentene 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).

２－２９

2-29

２－２１

2-21

In Example 13 of Patent Document 1, an organic electroluminescence device containing a compound (2-29) in a light emitting layer is described. In the organic electroluminescence element of Example 13, the light emitting layer is a thin-film deposition layer formed by simultaneously vapor-depositing the compound (2-29) and the condensed ring-containing compound on the 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 a compound (2-21) in a 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 fused ring-containing compound onto the hole transport layer. 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, the above-mentioned conventional light emitting element does not always have sufficient luminous efficiency, and needs to be further improved.
Therefore, an object of the present invention is to provide a light emitting element having excellent luminous efficiency.

The present invention provides the following [1] to [12].

[1] A light emitting device having an anode, a cathode, a first organic layer and a second organic layer provided between the anode and the cathode, and the first organic layer is represented by the formula (1). A light emitting device which is a layer containing the represented compound, and the second organic layer is a layer containing a crosslinked body of a crosslinking material.

［式中、
環Ｒ^１Ａ、環Ｒ^２Ａ及び環Ｒ^３Ａは、それぞれ独立に、芳香族炭化水素環を表し、該環は置換基を有していてもよい。該置換基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、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、環Ｒ^１Ａ、環Ｒ^２Ａ及び環Ｒ^３Ａのうちの少なくとも一つは、式（１－Ｓ）で表される基を有する。］

[During the ceremony,
Ring R ^1A , ring R ^2A , and ring R ^3A each independently represent an aromatic hydrocarbon ring, and the ring may have a substituent. When a plurality of the substituents 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 atom to which each is bonded.
However, at least one of ring R ^1A , ring R ^2A and ring R ^3A has a group represented by the formula (1-S). ]

［式中、Ａｒ^１Ｓ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。］

[In the formula, Ar ^1S represents an aryl group of the fused ring, and the group may have a substituent. ]

[2] The cross-linking material contains a low molecular weight compound having at least one cross-linking group selected from the cross-linking group A group or a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group. The light emitting element according to [1], which is a molecular compound.
(Crosslinking 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. When there are a plurality of R ^XLs , they may be the same or different, and when there are a plurality of n ^XLs , 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 of 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.
^LA represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and 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 there are multiple ^LAs , 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.
^KA represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and 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 there are multiple ^KAs , 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. ]

The light emitting device according to [1], wherein the crosslinked material is a small molecule 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 there are multiple Ar ^7s , 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 ring R ^1A , the ring R ^2A , and the ring R ^3A are a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, and a pyrene. The ring, a perylene ring, a chrysene ring, an inden ring, a fluoranthene ring or a benzofluoranthene ring (these rings may have a substituent), according to any one of [1] to [5]. Light emitting element.

[7] Any of [1] to [6], wherein the compound represented by the formula (1) is a compound represented by the formula (1-A) or a compound represented by the formula (1-B). The light emitting element described in Crab.

［式中、
Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ、Ｒ^１４Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ、Ｒ^３１Ａ、Ｒ^３２Ａ及びＲ^３３Ａ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、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
但し、Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ、Ｒ^１４Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ、Ｒ^３１Ａ、Ｒ^３２Ａ及びＲ^３３Ａのうちの少なくとも一つは、前記式（１－Ｓ）で表される基を有する。
Ｒ^１１ＡとＲ^１２Ａ、Ｒ^１２ＡとＲ^１３Ａ、Ｒ^１３ＡとＲ^１４Ａ、Ｒ^１４ＡとＲ^３１Ａ、Ｒ^３１ＡとＲ^３２Ａ、Ｒ^３２ＡとＲ^３３Ａ、Ｒ^３３ＡとＲ^２３Ａ、Ｒ^２３ＡとＲ^２２Ａ、Ｒ^２２ＡとＲ^２１Ａ、及び、Ｒ^２１ＡとＲ^１１Ａは、それぞれ結合して、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。］

[During the ceremony,
R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A are hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group. , Aryloxy group, monovalent heterocyclic group, substituted amino group or halogen atom, and these groups may have a substituent.
However, at least one of R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A is represented by the above formula (1-S). Has a group.
R ^11A and R ^12A , R ^12A and R ^13A , R ^13A and R ^14A , R ^14A and R ^31A , R ^31A and R ^32A , R ^32A and R ^33A , R ^33A and R ^23A , R ^23A and R ^22A , R ^22A . And R ^21A , and R ^21A and R ^11A may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

［式中、
Ｒ^１１Ｂ、Ｒ^１４Ｂ、Ｒ^１５Ｂ、Ｒ^１６Ｂ、Ｒ^１７Ｂ、Ｒ^１８Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ、Ｒ^３１Ｂ、Ｒ^３２Ｂ及びＲ^３３Ｂ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、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
但し、Ｒ^１１Ｂ、Ｒ^１４Ｂ、Ｒ^１５Ｂ、Ｒ^１６Ｂ、Ｒ^１７Ｂ、Ｒ^１８Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ、Ｒ^３１Ｂ、Ｒ^３２Ｂ及びＲ^３３Ｂのうちの少なくとも一つは、前記式（１－Ｓ）で表される基を有する。
Ｒ^１１ＢとＲ^１５Ｂ、Ｒ^１５ＢとＲ^１６Ｂ、Ｒ^１６ＢとＲ^１７Ｂ、Ｒ^１７ＢとＲ^１８Ｂ、Ｒ^１８ＢとＲ^１４Ｂ、Ｒ^１４ＢとＲ^３１Ｂ、Ｒ^３１ＢとＲ^３２Ｂ、Ｒ^３２ＢとＲ^３３Ｂ、Ｒ^３３ＢとＲ^２３Ｂ、Ｒ^２３ＢとＲ^２２Ｂ、Ｒ^２２ＢとＲ^２１Ｂ、及び、Ｒ^２１ＢとＲ^１１Ｂは、それぞれ結合して、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。］

[During the ceremony,
R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B are hydrogen atoms, alkyl groups, cycloalkyl groups, alkoxy groups, It represents a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups may have a substituent.
However, at least one of R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B is the above-mentioned formula (1-). It has a group represented by S).
R ^11B and R ^15B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , R ^18B and R ^14B , R ^14B and R ^31B , R ^31B and R ^32B , R ^32B and R ^33B , R ^33B . And R ^23B , R ^23B and R ^22B , R ^22B and R ^21B , and R ^21B and R ^11B , respectively, may be bonded to form a ring together with the carbon atom to which each is bonded. ]

[8] The Ar ^1S is a naphthalene ring, 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 light emitting device according to any one of [1] to [8], wherein the maximum peak wavelength of the emission spectrum of the compound represented by the formula (1) is 380 nm or more and 570 nm or less.

[10] The first organic layer further contains at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant and a light emitting material. , [1] to any one of [9].

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

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

[13] 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 compound represented by the formula (1).
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 device, 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.

[14] The method for manufacturing a light emitting device according to [13], 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 excellent luminous efficiency.

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 .

"Small molecule 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 either 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 without 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. A compound in which the ring itself exhibits aromaticity, and a compound 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, preferably 3 to 20, not including the number of carbon atoms of the substituent.
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, preferably 3 to 20, without including the carbon atom of the substituent. 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 the two hydrogen atoms directly bonded to the carbon atoms 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 phenantrenidyl 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。］

[In the formula, R and Ra independently represent ^a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, respectively. 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 does not include the number of carbon atoms of the substituent and is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15.
The divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acrydin, Examples thereof include divalent groups obtained by removing two hydrogen atoms from dihydroaclydin, furan, thiophene, azole, diazole, and triazole from the hydrogen atoms directly bonded to the carbon atom or hetero atom constituting the ring. Is a group represented by the formulas (AA-1) to (AA-34). A divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

［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 device of the present invention is 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, and the first organic layer is of the formula (1). It is a light emitting device which is a layer containing the compound represented by 1), and the second organic layer is a layer containing a crosslinked body of a crosslinking 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., and even 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 analysis.

<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 a compound represented by the formula (1).

<Compound represented by the formula (1)>
Next, the compound represented by the formula (1) will be described. The compound represented by the formula (1) is a light emitting material. The first organic layer may contain one compound represented by the formula (1) alone, or may contain two or more compounds.

The maximum peak wavelength of the emission spectrum of the compound represented by the formula (1) is preferably 380 nm or more and 570 nm or less, more preferably 390 nm or more and 520 nm or less, still more preferably 400 nm or more and 500 nm or less, and particularly preferably. It is 420 nm or more and 480 nm or less.

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

The number of carbon atoms of the aromatic hydrocarbon ring in rings R ^1A , ring R ^2A and ring R ^3A is usually 6 to 60, preferably 6 to 30, not including the number of carbon atoms of the substituent, and more. It is preferably 6 to 20.

Rings R ^1A , ring R ^2A and ring R ^3A include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring and a perylene ring. Examples thereof include a chrysen ring, an inden ring, a fluoranthene ring and a benzofluorentene ring, and since the light emitting element of the present invention has excellent light emission efficiency, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a spirobifluorene ring or A pyrene ring is preferable, a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring is more preferable, a benzene ring or a phenanthrene ring is more preferable, and these rings may have a substituent.

Ring R ^1A is preferably a naphthalene ring which may have a substituent because the luminous efficiency of the light emitting device of the present invention is more excellent.

Since the ring R ^2A and the ring R ^3A have higher luminous efficiency of the light emitting element of the present invention, a benzene ring which may have a substituent is preferable.

The substituents that the ring R ^1A , the ring R ^2A and the ring R ^3A may have are preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, and the like. It is an aryloxy group, a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and further preferably. , An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, particularly preferably an aryl group, and these groups are further preferred. It may have a substituent.

The number of carbon atoms of the aryl group in the substituents that the ring R ^1A , the ring R ^2A and the ring R ^3A may have is usually 6 to 60, preferably 6 without including the number of carbon atoms of the substituent. It is ~ 30, more preferably 6-20.

Examples of the aryl group in the substituents that the ring R ^1A , the ring R ^2A and the ring R ^3A may have include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthalene ring and a fluorene ring. , Spirovifluorene ring, pyrene ring, perylene ring, chrysen ring, inden ring, fluoranthrene ring and benzofluoranthrene ring, except for one hydrogen atom directly bonded to the carbon atom constituting the ring. , Preferably from a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a fluoranthene ring or a benzofluorentene ring, directly bonded to a carbon atom constituting the ring. It is a group consisting of a group excluding one hydrogen atom, and more preferably a carbon atom constituting a ring from a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring, a spirobifluorene ring, a fluoranthrene ring or a benzofluoranthrene ring. It is a group except for one hydrogen atom directly bonded to, and more preferably, hydrogen directly bonded to a carbon atom constituting the ring from a benzene ring, a naphthalene ring, a fluorene ring or a spirobifluorene ring. It is a group excluding one atom, particularly preferably a phenyl group, a naphthyl group or a fluorenyl group, and particularly preferably a phenyl group, and these groups may further have a substituent.

The number of carbon atoms of the monovalent heterocyclic group in the substituents that the ring R ^1A , the ring R ^2A and the ring R ^3A may have is usually 2 to 60, not including the number of carbon atoms of the substituent. , It is preferably 3 to 30, and more preferably 3 to 20.

Examples of the monovalent heterocyclic group in the substituent that the ring R ^1A , the ring R ^2A and the ring R ^3A may have include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring and a triazine ring. Azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, indole ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, aclydin ring, 9,10- Examples thereof include a group consisting of a dihydroacridin ring, an acridone ring, a phenazine ring and a 5,10-dihydrophenazine ring excluding one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, and a pyridine ring is preferable. , Diazabenzene ring, triazine ring, azanaphthalene ring, diazanaphthalene ring, carbazole ring, azacarbazole ring, diazacarbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring or It is a group consisting of a 5,10-dihydrophenazine ring excluding one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, and more preferably a pyridine ring, a diazabenzene ring, a triazine ring, or an azanaphthalene ring. , A diazanaphthalene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, except for one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, and these groups further contain a substituent. You may have.

Among the substituted amino groups in the substituents that the ring R ^1A , the ring R ^2A and the ring R ^3A may have, the substituent of the amino group is preferably an aryl group or a monovalent heterocyclic group, and the aryl group is preferable. More preferably, these groups may further have substituents. 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 ring R ^1A , ring R ^2A and ring R ^3A may have. Examples and preferred ranges of monovalent heterocyclic groups in the substituents of the amino group include examples of monovalent heterocyclic groups in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have. Same as the preferred range.

Substituents that may be further possessed by the substituents that the rings R ^1A , the ring R ^2A and the ring R ^3A may have are preferably an alkyl group, a cycloalkyl group, an aryl group, and a monovalent complex. It is a ring group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a substituted amino group or a halogen atom, and more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group. Alternatively, it is a substituted amino group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, particularly preferably an alkyl group, a cycloalkyl group or an aryl group, and particularly preferably. It is an alkyl group or a cycloalkyl group, and these groups may further have a substituent.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that the substituents that the rings R ^1A , R ^2A and R ^3A may have may further have. , The examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, respectively.

If there are multiple substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, they may be the same or different and may be bonded together to form a ring with the carbon atoms to which they are bonded. Although it may be formed, it is preferable not to form a ring because the maximum peak wavelength of the emission spectrum of the compound represented by the formula (1) is a short wavelength.

"At least one of ring R ^1A , ring R ^2A and ring R ^3A has a group represented by the formula (1-S)" means that of ring R ^1A , ring R ^2A and ring R ^3A . It means that a part or all of the hydrogen atom directly bonded to the carbon atom constituting at least one ring is substituted with the group represented by the formula (1-S).

Since the luminous efficiency of the light emitting device of the present invention is excellent, it is preferable that at least one of the ring R ^1A and the ring R ^2A has a group represented by the formula (1-S), and the ring R ^2A has the formula (1-S). It is more preferable to have a group represented by S).

The number of groups represented by the formula (1-S) contained in at least one of the rings R ^1A , the ring R ^2A and the ring R ^3A is usually 1 to 10, and is preferable because it is easy to synthesize. It is 1 to 5, more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1.

The number of groups represented by the formula (1-S) contained in the compound represented by the formula (1) is usually 1 to 15, the luminous efficiency of the light emitting device of the present invention is excellent, and the synthesis is easy. Therefore, it is preferably 1 to 10, more preferably 1 to 5, still more preferably 1 to 3, particularly preferably 1 or 2, and preferably 1.

When the compound represented by the formula (1) has a plurality of groups represented by the formula (1-S), they may be the same or different.

[Group represented by formula (1-S)]
The number of carbon atoms of the aryl group of the fused ring in Ar ^1S 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 Ar ^1S include naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, triphenylene ring, naphthalene ring, fluorene ring, spirobifluorene ring, pyrene ring, perylene ring, chrysen ring, inden ring, fluorene ring or benzo. Examples thereof include a group consisting of a fluorene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, preferably a naphthalene ring, an anthracene ring, a phenanthrene ring, a dihydrophenanthrene ring, a fluorene ring, and a spirobi. It is a group consisting of a fluorene ring, a pyrene ring, a fluorene ring or a benzofluorene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, and more preferably a naphthalene ring, an anthracene ring or a fluorene ring. , A group consisting of a spirobifluorene ring, a fluorene ring or a benzofluorene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, more preferably a naphthalene ring, a fluorene ring or a spirobi. A group consisting of a fluorene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, particularly preferably a naphthyl group or a fluoreneyl group, even if these groups have a substituent. good.

The examples and preferred ranges of substituents that Ar ^1S may have are the same as the examples and preferred ranges of substituents that ring R ^1A , ring R ^2A and ring R ^3A may have.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that Ar ^1S may have are included in Ring R ^1A , Ring R ^2A and Ring R ^3A , respectively. It is the same as the examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the preferred substituents.

Examples and preferred ranges of substituents that Ar ^1S may have may further include substituents that ring R ^1A , ring R ^2A and ring R ³ may have. It is the same as the example and preferable range of substituents which may be possessed.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that the substituents that the rings R ^1A , R ^2A and R ^3A may have may further have. , The examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, respectively.

The group represented by the formula (1-S) is preferably a group represented by the formulas (1-S1) to (1-S17) because the luminous efficiency of the light emitting element of the present invention is more excellent. More preferably, it is a group represented by the formula (1-S1) to the formula (1-S8) or the formula (1-S14) to the formula (1-S17), and more preferably, the formula (1-S1), It is a group represented by the formula (1-S2) or the formula (1-S5) to the formula (1-S8), and is particularly preferably the formula (1-S1), the formula (1-S2), and the formula (1-S8). It is a group represented by 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、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。］

[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, substituted amino group or Representing a halogen atom, these groups may have substituents. ]

^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 or a substituted amino group, and more preferably a hydrogen atom, an alkyl group, and the like. It is a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, in particular. A hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group is preferable, and a hydrogen atom or an aryl group is particularly preferable, 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 or a substituted amino group, and more preferably an alkyl group or a cycloalkyl group. , An alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and particularly preferably an alkyl group. It may be a cycloalkyl group or an aryl group, 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 aryls in substituents that ring R1A , ring R2A} and ring ^R3A may have, respectively. The same is true for the examples and preferred ranges of groups, monovalent heterocyclic groups and substituted amino groups.

Examples and preferred ranges of substituents that ^RS1 and ^RS2 may have include substitutions that may be further possessed by the substituents that ring ^{R1A ,} ring ^R2A and ring R3 may have. Same as the group example and preferred range.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that ^RS1 and ^RS2 may have include ring R ^1A , ring R ^2A and ring R ^3A , 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.

The compound represented by the formula (1) is preferably a compound represented by the formula (1-A) or a compound represented by the formula (1-B) because the luminous efficiency of the light emitting device is more excellent. More preferably, it is a compound represented by the formula (1-B).

<Compound represented by the formula (1-A)>
The examples and preferred ranges of R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A are the same as those of ^{RS 1} and preferred ranges, respectively.

Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A are: 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 the ring R ^1A , the ring R ^2A and the ring R ^3A may have, respectively.

Examples and preferred ranges of substituents that R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A may have are Ring R ^1A , Ring. It is the same as the example and preferable range of substituents that R ^2A and ring R ^3A may have.

Aryl groups, monovalent heterocyclic groups and substitutions in the substituents that R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A may have. Examples of amino groups and preferred ranges are examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, respectively. Is the same as.

Examples of substituents that may be further possessed by the substituents that may be possessed by R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A . And the preferred range is the same as the examples and preferred ranges of substituents that may be further possessed by the substituents that ring R ^1A , ring R ^2A and ring R ³ may have.

The aryl in the substituents that the substituents that R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A may have may further have. Examples and preferred ranges of groups, monovalent heterocyclic groups and substituted amino groups are aryl groups and monovalent heterocycles in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, respectively. Same as for examples and preferred ranges of groups and substituted amino groups.

Since the luminous efficiency of the light emitting device of the present invention is more excellent, at least one of R ^11A , R ^12A , R ^13A , R ^14A , R ^22A , R ^23A , R ^32A and R ^33A is represented by the formula (1-S). It is preferable that the group is represented by a group, and at least one of R ^12A , R ^13A , R ^22A , R ^23A , R ^32A and R ^33A is a group represented by the formula (1-S). Preferably, at least one of R ^12A , R ^23A and R ^33A is more preferably a group represented by the formula (1-S), and at least one of R ^23A and R ^33A is of the formula (1). It is particularly preferable that the group is represented by —S).

R ^11A and R ^14A are preferably a hydrogen atom, an aryl group or a group represented by the formula (1-S), and more preferably a hydrogen atom or a group because the light emitting efficiency of the light emitting element of the present invention is further excellent. It is an aryl group, more preferably an aryl group.

R ^12A , R ^13A , R ^21A , R ^22A , R ^31A and R ^32A are preferably hydrogen atoms, aryl groups or groups represented by the formula (1-S) because they are easy to synthesize, and more preferably. Is a hydrogen atom or an aryl group, more preferably a hydrogen atom.

Since R ^23A and R ^33A are more excellent in luminous efficiency of the light emitting element of the present invention, they are preferably a hydrogen atom, an aryl group or a group represented by the formula (1-S), and more preferably a hydrogen atom or a group represented by the formula (1-S). It is a group represented by the formula (1-S).

R ^11A and R ^12A , R ^12A and R ^13A , R ^13A and R ^14A , R ^14A and R ^31A , R ^31A and R ^32A , R ^32A and R ^33A , R ^33A and R ^23A , R ^23A and R ^22A , R ^22A . And R ^21A , and R ^21A and R ^11A have short wavelengths at the maximum peak wavelength of the emission spectrum of the compound represented by the formula (1-A). It is preferable not to form a ring.

<Compound represented by formula (1-B)>
Examples and preferred ranges of R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B are examples of R ^S1 and preferred, respectively. Same as range.

Aryl groups represented by R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B , and monovalent heterocyclic groups and substitutions. Examples of amino groups and preferred ranges are examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, respectively. Is the same as.

Examples and preferred ranges of substituents that R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B may have are: , Ring R ^1A , Ring R ^2A and Ring R ^3A may have the same examples and preferred ranges of substituents.

Aryl groups and monovalents in the substituents that R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B may have. Examples and preferred ranges of the heterocyclic group and the substituted amino group of the above are the aryl group in the substituent which the ring R ^1A , the ring R ^2A and the ring R ^3A may have, respectively, the monovalent heterocyclic group and the substituted amino. Same as the group example and preferred range.

There are further substituents that R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B may have. The examples and preferred ranges of the preferred substituents are the same as the examples and preferred ranges of the substituents which the rings R ^1A , R ^2A and Ring R ³ may have may further have. ..

There are further substituents that R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B may have. Examples and preferred ranges of aryl groups, monovalent heterocyclic groups and substituted amino groups in the preferred substituents are the aryl groups in the substituents that ring R ^1A , ring R ^2A and ring R ^3A may have, respectively. Same as for examples and preferred ranges of monovalent heterocyclic groups and substituted amino groups.

Since the luminous efficiency of the light emitting device of the present invention is more excellent, at least one of R ^11B , R ^14B , R ^16B , R ^17B , R ^22B , R ^23B , R ^32B and R ^33B is represented by the formula (1-S). It is preferable that the group is represented by a group, and at least one of R ^16B , R ^17B , R ^22B , R ^23B , R ^32B and R ^33B is a group represented by the formula (1-S). Preferably, at least one of R ^16B , R ^17B , R ^23B and R ^33B is more preferably a group represented by the formula (1-S), and at least one of R ^16B and R ^23B is of the formula (1-S). It is particularly preferable that the group is represented by (1-S).

R ^11B and R ^14B are preferably a hydrogen atom, an aryl group or a group represented by the formula (1-S), and more preferably a hydrogen atom or a group because the light emitting efficiency of the light emitting element of the present invention is further excellent. It is an aryl group, more preferably an aryl group.

R ^15B , R ^18B , R ^21B , R ^22B , R ^31B and R ^32B are preferably hydrogen atoms, aryl groups or groups represented by the formula (1-S) because they are easy to synthesize, and more preferably. Is a hydrogen atom or an aryl group, more preferably a hydrogen atom.

R ^16B , R ^17B , R ^23B and R ^33B are preferably hydrogen atoms, aryl groups or groups represented by the formula (1-S) because the luminous efficiency of the light emitting element of the present invention is further excellent. It is preferably a hydrogen atom or a group represented by the formula (1-S).

R ^11B and R ^15B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , R ^18B and R ^14B , R ^14B and R ^31B , R ^31B and R ^32B , R ^32B and R ^33B , R ^33B . And R ^23B , R ^23B and R ^22B , R ^22B and R ^21B , and R ^21B and R ^11B have short wavelengths at the maximum peak wavelength of the emission spectrum of the compound represented by the formula (1-B). It is preferable that they are bonded to each other and do not form a ring together with the carbon atom to which they are bonded.

Specific examples of the compound represented by the formula (1) include compounds represented by the following formula.

The compound represented by the formula (1) is described in Aldrich, Lumisense 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-2011-037744, and JP-A-2011-174059.

[Host material]
Since the luminous efficiency of the light emitting element of the present invention is more excellent, the first organic layer is composed of the compound represented by the formula (1) and the hole injecting property, the hole transporting property, the electron injecting property and the electron transporting property. It is preferable that the layer contains a host material having at least one function selected from the group. When the first organic layer is a layer containing the compound represented by the formula (1) and the host material, the host material may be contained alone or in combination of two or more. good.

When the first organic layer is a layer containing the compound represented by the formula (1) and the host material, the content of the compound represented by the formula (1) is represented by the formula (1). When the total of the compound and the host material is 100 parts by weight, it is usually 0.05 to 80 parts by weight, preferably 0.1 to 50 parts by weight, more preferably 1 to 30 parts by weight, and further preferably 5 parts. ~ 15 parts by weight.

When the first organic layer is a layer containing the compound represented by the formula (1) and the host material, the lowest excited singlet state (S ₁ ) of the host material is the light emission of the light emitting element of the present invention. Since the efficiency is excellent, it is preferable that the energy level is equivalent to or higher than that of S ₁ of the compound represented by the formula (1).

As the host material, since the light emitting element of the present invention can be produced by a solution coating process, it is soluble in a solvent capable of dissolving the compound represented by the formula (1) contained in the first organic layer. It is preferable that it indicates.

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

[Small molecule host]
A small molecule compound (hereinafter referred to as "small molecule host") preferable as a host material will be described.

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

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

[During the ceremony,
Ar ^H1 and Ar ^H2 each independently represent an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.
n ^H1 represents an integer of 0 or more and 15 or less.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by − [C ( ^RH11 ) ₂ ] n ^H11 −, and these groups may have a substituent. When there are a plurality of L ^H1 , they may be the same or different. n ^H11 represents an integer of 1 or more and 10 or less. R ^H11 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. The plurality of R ^H11s present may be the same or different, or may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

Ar ^H1 and Ar ^H2 are preferably an aryl group or a monovalent heterocyclic group, and more preferably an aryl group. More preferably, from the viewpoint of luminous efficiency, at least one of Ar ^H1 and Ar ^H2 is an aryl group of the fused ring. These groups may have substituents.

The number of carbon atoms of the aryl group in Ar ^H1 and Ar ^H2 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 20, excluding the number of carbon atoms of the substituent.

Examples of the aryl group in Ar ^H1 and Ar ^H2 include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, a perylene ring and a chrysen ring. Examples thereof include a group consisting of an inden ring, a fluoranthene ring or a benzofluorentene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, preferably a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring. , Dihydrophenanthrene ring, fluorene ring, spirobifluorene ring, pyrene ring or chrysen ring, excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, more preferably a benzene ring or naphthalene. A group consisting of a ring, an anthracene ring, a pyrene ring, a fluorene ring, or a spirobifluorene ring excluding one hydrogen atom directly bonded to a carbon atom constituting the ring, more preferably a phenyl group, and further preferably a phenyl group. It may be a naphthyl group or an anthrasenyl group, particularly preferably a phenyl group or a naphthyl group, and these groups may further have a substituent.

The definitions, examples and preferred ranges of aryl groups of fused rings in Ar ^H1 and Ar ^H2 are the same as the definitions, examples and preferred ranges of aryl groups of fused rings in Ar ^1S .

The number of carbon atoms of the monovalent heterocyclic group in Ar ^H1 and Ar ^H2 is usually 2 to 60, preferably 3 to 30, and more preferably 3 to 20 without including the number of carbon atoms of the substituent. Is.

Examples of the monovalent heterocyclic group in Ar ^H1 and Ar ^H2 include a pyrrole ring, a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, an azanaphthalene ring, a diazanaphthalene ring, a triazanaphthalene ring, and an indol. Ring, benzodiazole ring, benzotriazole 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 ring, except for one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, preferably a diazole ring, a triazole ring, or a pyridine ring. , Diazabenzene ring, triazine ring, indole ring, benzodiazole ring, benzotriazole ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring or 5,10-dihydrophenazine It is a group consisting of a ring excluding one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, and more preferably a diazole ring, a triazole ring, a pyridine ring, a diazabenzene ring, a triazine ring, or a benzodiazole. It is a group consisting of a ring, a benzotriazole ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring except for one hydrogen atom directly bonded to a carbon atom or a heteroatom constituting the ring, and these groups further contain a substituent. You may have.

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

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

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

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

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

n ^H1 is preferably an integer of 0 or more and 10 or less, more preferably an integer of 1 or more and 5 or less, and further preferably an integer of 1 or more and 3 or less.

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

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

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

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

n ^H11 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and further preferably 1.

^RH11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and a hydrogen atom or an alkyl group. More preferably, these groups may have a substituent.

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

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

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

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

［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-8), and from the viewpoint of the luminous efficiency of the light emitting element of the present invention. , Preferably a structural unit represented by the formula (Y-1), the formula (Y-2) or the formula (Y-8), and is preferably the formula (Y-) from the viewpoint of electron transportability of the polymer host. It is a structural unit represented by 3) or the formula (Y-4), and is preferably represented by the formulas (Y-5) to (Y-7) from the viewpoint of hole transportability of the polymer host. It is a structural unit.

The polymer host is preferably a polymer compound containing a structural unit represented by the formula (Y-2) and / or the formula (Y-8) because the luminous efficiency of the light emitting element of the present invention is more excellent. More preferably, it is a polymer compound containing a structural unit represented by the formula (Y-2) and the formula (Y-8).

［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 represents a group represented by -C ( ^RY2 ) _2- , -C ( ^RY2 ) = C ( ^RY2 )-or -C ( ^RY2 ) ₂ -C ( ^RY2 ) _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 XY1} , the combination of two ^RY2s in the group represented by −C ( ^RY2 ) ₂₋ is preferably a complex having both an alkyl group or a cycloalkyl group, both having an aryl group, and both having a monovalent value. 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 XY1} , the combination of two ^RY2s in the group represented by −C ( ^RY2 ) = C ( ^RY2 ) − 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 XY1} , the four ^RY2s among the groups represented by −C ( ^RY2 ) ₂ −C ( ^RY2 ) ₂₋ preferably contain an alkyl group or a substituent which may have a substituent. It is a cycloalkyl group that may have. Multiple ^RY2s may be bonded to each other to form a ring with the atoms to which they are bonded. If ^RY2 forms a ring, then -C ( ^RY2 ) ₂ -C ( ^RY2 ) _2- 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.

［式中、Ｒ^Y1は前記を同じ意味を表す。］

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

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 has a higher luminous efficiency of the light emitting element of the present invention, and therefore is included in the total amount of the structural units contained in the polymer host. On the other hand, it is preferably 10 to 100 mol%, and more preferably 50 to 100 mol%.

It is a structural unit represented by the formula (Y), and Ar ^Y1 is a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. Since the structural unit which is the basis of the above is excellent in charge transportability of the polymer host, it is preferably 0.5 to 40 mol%, more preferably 3 to 30% with respect to the total amount of the structural units contained in the polymer host. Mol%.

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

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

［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 luminous efficiency of the light emitting device of the present invention is more excellent, a ^X1 is preferably an integer of 2 or less, and more preferably 1.

Since a ^X2 has a higher luminous efficiency of the light emitting device of the present invention, it 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 the formula (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.

The substituents that the groups represented by Ar ^X1 to Ar ^X4 and R ^X1 to R ^X3 may have are preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups further have a substituent. You may 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 formulas (X-3) to (X). 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 50 mol%, more preferably 1 to 1 to the total amount of the structural units contained in the polymer host. It is 40 mol%, more preferably 5 to 30 mol%.

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

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

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

［表中、ｐ、ｑ、ｒ、ｓ及びｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝100であり、かつ、100≧ｐ＋ｑ＋ｒ＋ｓ≧70である。］

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

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

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

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

[Manufacturing method of polymer host]
The polymer host can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc., and can be produced by Suzuki reaction, Yamamoto reaction, Buchwald, etc. Examples thereof include a method of polymerizing by a coupling reaction using a transition metal catalyst such as a 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 host is low, it can be purified by a usual method such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography and the like.

[First composition]
The first organic layer includes a compound represented by the formula (1), and the above-mentioned host material, hole transport material, hole injection material, electron transport material, electron injection material, and light emitting material (represented by the formula (1)). Even a layer containing a composition (hereinafter, also referred to as "first composition") containing at least one material selected from the group consisting of an antioxidant (hereinafter, also referred to as "first composition"). good.

[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 to 150 parts by weight, when the compound represented by the formula (1) is 100 parts by weight. Is.

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

[Electron transport material]
Electron transport materials are classified into low molecular weight compounds and high molecular weight compounds. The electron transport material may have a 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 150 parts by weight, when the compound represented by the formula (1) is 100 parts by weight. be.

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, preferably 1 to 400 parts by weight, respectively, when the compound represented by the formula (1) is 100 parts by weight. Is 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 phenantrenicyl group, a dihydrophenanthrendyl 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 anthracene diyl group, 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 compound represented by the formula (1) is 100 parts 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 compound represented by the formula (1) and does not inhibit light emission and charge transport. For example, a phenolic antioxidant and a phosphorus-based antioxidant may be used. Can be mentioned.

In the first composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by weight when the compound represented by the formula (1) is 100 parts by weight.

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

[First ink]
The composition containing the compound represented by the formula (1) and the solvent (hereinafter, also referred to as “first ink”) includes a spin coating method, a casting method, a microgravia coating method, a gravure coating method, and a bar. Suitable for wet methods such as coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexo printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc. Can be 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 during ejection. Since it is difficult, it is preferably 1 to 20 mPa · s at 25 ° C.

The solvent contained in the first ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of the solvent include chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisol; toluene, 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 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight, when the compound represented by the formula (1) is 100 parts by weight.

<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 since the light emitting efficiency of the light emitting element of the present invention is more excellent, the cross-linking material has at least one cross-linking group selected from the cross-linking group A group. A molecular compound (hereinafter, also referred to as "low molecular weight compound of the second organic layer") or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A group (hereinafter, "" It is also referred to as 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 light emitting element of the present invention has more excellent light emitting efficiency, and therefore, the formulas (XL-1) to (XL-4) and the formulas (XL-7) to formulas (XL-7) to the formulas 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), 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) or the like. 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-17). ) Is a cross-linking group.

[Polymer compound of the second organic layer]
The structural unit having at least one cross-linking group selected from the group A of the cross-linking 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 luminous efficiency of the light emitting element of the present invention is more excellent.

n is preferably 2 because the luminous efficiency of the light emitting element of the present invention is more excellent.

Ar ³ is an aromatic hydrocarbon group which may have a substituent because the luminous efficiency of the light emitting element of the present invention is more excellent.

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.

The alkylene group represented by ^LA is usually 1 to 20, preferably 1 to 15, and more preferably 1 to 10 without including the number of carbon atoms of the substituent. The cycloalkylene group represented by ^LA is usually 3 to 20 without including the number of carbon atoms of the substituent.
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.

The alkylene group and the cycloalkylene group represented by ^LA 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.

The arylene group represented by ^LA 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 LA is preferably a group represented by the formulas ( ^AA -1) to (AA-34).

^LA is preferably an arylene group or an alkylene group, and more preferably a phenylene group, a fluorinatedyl group or an alkylene group because it facilitates the production of the polymer compound of the second organic layer. The group of may have a substituent.

As the cross-linking group represented by X, since the light emitting efficiency of the light emitting element of the present invention is more excellent, the formulas (XL-1) to (XL-4) and the formulas (XL-7) to (XL) are preferable. -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). , XL-10, formula (XL-16) or formula (XL-17), more preferably formula (XL-1), formula (XL-16) or formula (XL-1). 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 the cross-linking group represented by the formula (XL-17). It is a crosslinked group represented.

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, still more preferably 0 or 1, and particularly preferably 0, because the luminous efficiency of the light emitting element of the present invention is more excellent. Is.

m is preferably 1 or 2, and more preferably 2 because the luminous efficiency of the light emitting device of the present invention is more excellent.

c is preferably 0 because it facilitates the production of the polymer compound of the second organic layer and the luminous efficiency of the light emitting element of the present invention is more excellent.

Ar ⁵ is an aromatic hydrocarbon group which may have a substituent because the luminous efficiency of the light emitting element of the present invention is more excellent.

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 luminous efficiency of the light emitting device of the present invention is more excellent.

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.

The definitions and examples of the alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by ^KA are the alkylene group, cycloalkylene group, arylene group and divalent complex represented by ^LA , respectively. It is the same as the definition and example of the ring group.

^KA is preferably a phenylene group or a methylene group because it facilitates the production of the polymer compound of the second organic layer.

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 formula (2) include the structural units represented by the formulas (2-1) to (2-30), and the structural units represented by the formula (2') include. For example, the structural units 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) -Structure 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).

［その他の構成単位］
第２の有機層の高分子化合物は、正孔輸送性が優れるので、更に、式(Ｘ)で表される構成単位を含むことが好ましい。また、第２の有機層の高分子化合物は、本発明の発光素子の発光効率がより優れるので、更に、式(Ｙ)で表される構成単位を含むことが好ましい。

[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, since the polymer compound of the second organic layer has more excellent luminous efficiency of the light emitting device of the present invention, it is preferable that the polymer compound further contains a structural unit represented by the formula (Y).

Since the polymer compound of the second organic layer has excellent hole transportability and the luminous efficiency of the light emitting device of the present invention is more excellent, the structural unit represented by the formula (X) and the formula (Y) are further excellent. It is preferable to include a structural unit represented by.

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

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

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

The structural unit represented by the formula (Y) in which Ar ^Y1 is an arylene group is included in the polymer compound of the second organic layer because the luminous efficiency of the light emitting element of the present invention is more excellent. It is preferably 0.5 to 80 mol%, more preferably 30 to 60 mol%, based on the total amount of the constituent units.

It is a structural unit represented by the formula (Y), and 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%.

Examples of the polymer compound of the second organic layer include the polymer compounds P-7 to P-14 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-7 to P-14 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 the same method as the above-mentioned method for producing a polymer host.

[Small molecule compound in the second organic layer]
The small molecule compound of the second organic layer is preferably a small molecule compound represented by the formula (3).

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, because it facilitates the synthesis of the cross-linking material. It is 1, and particularly preferably 0.

m ^B2 is usually an integer of 0 to 10, which facilitates the synthesis of the crosslinked material and has more excellent luminous efficiency of the light emitting element of the present invention. Therefore, it is preferably an integer of 0 to 5, more preferably. It 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 cross-linking material. be.

The definition and example of the arylene group portion excluding the ^mb3 substituent of the aromatic hydrocarbon group represented by Ar ⁷ are the definition and example of the arylene group represented by Ar ^{X 2} in the above formula (X). 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). It is the 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 luminous efficiency of the light emitting element of the present invention is more excellent, and this aromatic hydrocarbon group may have a substituent.

The definitions and examples of the alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by ^LB1 are as described above, respectively, of the alkylene group, cycloalkylene group, arylene group and divalent represented by ^LA . 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), formula (XL-3), formula (XL-7) to formula (XL-10), formula (XL-16) or a bridging group represented by 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 small molecule compounds represented by the formulas (3-1) to (3-16), preferably represented by the formulas (3-1) to (3-10). It is a small molecule compound, and more preferably a small molecule compound represented by the formulas (3-5) to (3-9).

The small molecule compound of the second organic layer is 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 light emitting material contained in the second composition are the hole transporting material contained in the first composition. Same as examples and preferred ranges of electron transport material, hole injection material, electron injection material and luminescent material. In the second composition, the blending amount of the hole transport material, the electron transport material, the hole injection material, the electron injection material and the light emitting material is usually 1 when the crosslinked body of the crosslinked material is 100 parts by weight. It is up to 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 100,000 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 device of the present invention, the first organic layer and the second organic layer are preferably adjacent to each other because the light emitting efficiency of the light emitting device of the present invention is more excellent. 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 luminous efficiency of the light emitting device of the present invention is more excellent, and the anode and the first organic layer are preferable. A hole transport layer or a second light emitting layer provided between the organic layers 1 is more preferable, and a hole transport layer provided between the anode and the first organic layer is further preferable. ..

In the light emitting device of the present invention, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, so that the anode and the first It is preferable to further have a hole injection layer between the two organic layers. Further, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the first organic layer are used. 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 element 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 luminous efficiency of the light emitting element of the present invention is more excellent, so that the anode and the light emitting element It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the second organic layer. Further, when the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the first organic layer It is preferable to further have at least one layer of an electron injecting layer and an electron transporting layer 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 cathode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, so that the anode and 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. Further, when the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the second organic layer are more excellent. 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 an electron transport layer provided between the cathode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, 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 transport layer. Further, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the luminous efficiency of the light emitting device of the present invention is more excellent, so that the cathode and the second organic layer are combined. It is preferable to have an electron injection layer in between.

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 luminous efficiency of the light emitting device of the present invention is more excellent, 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 device of the present invention, the order, number, and thickness of the layers to be laminated may be adjusted in consideration of the luminous efficiency of the light emitting device and the device 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 compound; composite 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 intercalation compounds. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy.

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 a first light emitting layer, a second light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer. 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 the planar light emitting element, or forming an extremely thick layer to be a non-light emitting part 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. However, Examples D1, D3, D4, D5, D7, D8, D10 and D11 are reference 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 to 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 a 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 toluene at a concentration of about 0.8 × 10 ^-4 wt% 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 and HM-2, Obtained Compound HM-1 was synthesized according to the method described in JP-A-2011-174059.
Compound HM-2 was purchased from AK Scientific.

<Synthesis Example EM1> The synthetic compound EM-1 of the compounds EM-1, EM-2 and EM-3 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.

<Synthesis Example EM4> Synthesis of compound EM-4 Compound EM-4a (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, JP-A-2015. Compound EM-4b (9.00 g), tetrakis (triphenylphosphine) palladium (0) (0.294 g), and 20 wt% tetrabutylammonium hydroxide aqueous solution (18.9 g) synthesized according to the method described in JP-A-101751. ) 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] ⁺

<Synthesis Example EM5> Synthetic compound EM-5 of compound EM-5 was synthesized according to the method described in International Publication No. 2008/059713.

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 440 nm.
The maximum peak wavelength of the emission spectrum of compound EM-5 was 432 nm.

<Synthesis Example M1> Synthesis and Acquisition of Compounds M1 to M11 Compound M1 was synthesized according to the method described in JP2012-144721.
As the compound M2, a commercially available product was used.
Compound M3 was synthesized according to the method described in WO 2015/145871.
Compound M4 was synthesized according to the method described in WO 2013/146806.
Compound M5 was synthesized according to the method described in WO 2005/049546.
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.
Compound M10 was synthesized according to the method described in International Publication No. 2002/045184.
Compound M11 was synthesized according to the method described in JP-A-2012-144721.

<Synthesis Example HP1> Synthesis of Polymer Compound HP-1
(Step 1) After the inside of the reaction vessel is made into an inert gas atmosphere, compound M1 (1.73 g), compound M2 (0.843 g), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.2 mg) and toluene (40 ml). ) Was added and heated to 105 ° C.
(Step 2) A 20 wt% tetraethylammonium hydroxide aqueous solution (8.7 g) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 3 hours.
(Step 3) Then, 9-bromoanthracene (64.1 mg), a 20 wt% tetraethylammonium hydroxide aqueous solution (8.8 g) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.2 mg) are added thereto. It was refluxed for 16 hours.
(Step 4) Then, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling the obtained reaction solution, the mixture was washed twice with water, twice with a 3 wt% acetic acid aqueous solution, and twice with water, and the obtained solution was added dropwise to methanol to cause precipitation. The precipitate was dissolved in toluene and purified by passing the solution in the order of an alumina column and a silica gel column. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain 0.91 g of the polymer compound HP-1. The polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HP-1 were Mn = 1.2 × 10 ⁵ and Mw = 4.8 × 10 ⁵ , respectively.

According to the theoretical value obtained from the amount of the charged raw material, the polymer compound HP-1 is composed of the structural unit derived from the compound M1 and the structural unit derived from the compound M2 in a molar ratio of 50:50. Is a copolymer.

<Synthesis Example HP2> Synthesis of Polymer Compound HP-2 The polymer compound HP-2 was synthesized using the compounds M7, M10 and the compound M11 according to the method described in JP-A-2011-176304.

The polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HP-2 were Mn = 3.9 × ^{10 4} and Mw = 1.0 × 105, respectively.

According to the theoretical value obtained from the amount of the charged raw material, the polymer compound HP-2 has 50 constituent units derived from the compound M10, the constituent units derived from the compound M11, and the constituent units derived from the compound M7. It is a copolymer composed of a molar ratio of: 45: 5.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 Polymer compound HTL-1 was synthesized by using Compound M6 and Compound M7 according to the method described in JP2012-36381.

The polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HTL-1 were Mn = 8.1 × ^{10 4} and Mw = 3.4 × 105, respectively.

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

The polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HTL-2 were Mn = ^4.5 × 10 ⁴ and Mw = 1.5 × 105, respectively.

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 polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HTL- ³ were Mn = 8.9 × 10 ⁴ and Mw = 4.2 × 105, respectively.

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 polystyrene-equivalent number average molecular weight and weight average molecular weight of the polymer compound HTL-4 were Mn = 2.3 × ^{10 4} and Mw = 1.2 × 105, respectively.

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 the small molecule compound HTL-5>
The small molecule compound HTL-5 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 to a thickness of 35 nm by a spin coating method. The 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 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 by a spin coating method to a thickness of 60 nm, and heated on a hot plate at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. 1 organic layer was formed.

(Cathode formation)
After reducing the pressure of the substrate on which the first organic layer was formed to 1 × 10 ^-4 Pa or less in the vapor deposition machine, sodium fluoride was placed on the first organic layer as a cathode 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 luminous efficiency at 50 cd / m ² was 4.13 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.24). The luminous efficiency at 200 cd / m ² was 4.11 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.23).

<Example D2> Preparation and evaluation of light emitting element D2 A light emitting element D2 was produced in the same manner as in Example D1 except that the polymer compound HP-1 was used instead of the compound HM-2 in Example D1. ..

EL light emission was observed by applying a voltage to the light emitting element D2. The luminous efficiency at 50 cd / m ² was 5.44 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.16). The luminous efficiency at 200 cd / m ² was 5.49 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.16).

<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 luminous efficiency at 50 cd / m ² was 3.08 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.20). The luminous efficiency at 200 cd / m ² was 2.66 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.18).

<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 luminous efficiency at 50 cd / m ² was 2.21 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17). The luminous efficiency at 200 cd / m ² was 2.01 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17).

<Example D5> Fabrication and evaluation of light emitting element D5 The light emitting element D5 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 D5. The luminous efficiency at 50 cd / m ² was 2.19 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.16). The luminous efficiency at 200 cd / m ² was 2.30 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.18).

<Example D6> Fabrication and evaluation of light emitting element D6 The light emitting element D6 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 D6. The luminous efficiency at 50 cd / m ² was 3.03 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.15). The luminous efficiency at 200 cd / m ² was 3.70 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.15).

<Example D7> Fabrication and evaluation of light emitting device D7 The light emitting device D7 is used in the same manner as in Example D3 except that the polymer compound HTL-3 is used instead of the polymer compound HTL-4 in Example D3. Made.

EL light emission was observed by applying a voltage to the light emitting element D7. The luminous efficiency at 50 cd / m ² was 0.99 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.12). The luminous efficiency at 200 cd / m ² was 1.10 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.12).

<Example D8> Fabrication and evaluation of light emitting element D8 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 D8 was produced in the same manner as in Example D1 except that "the low molecular weight compound HTL-5 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 D8. The luminous efficiency at 50 cd / m ² was 2.56 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17). The luminous efficiency at 200 cd / m ² was 3.26 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.16).

<Example D9> Fabrication and evaluation of light emitting element D9 In Example D2 (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 D9 was produced in the same manner as in Example D2, except that "the low molecular weight compound HTL-5 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 D9. The luminous efficiency at 50 cd / m ² was 3.59 cd / A, and the CIE chromaticity coordinates (x, y) were (0.17, 0.20). The luminous efficiency at 200 cd / m ² was 4.16 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

<Example D10> Fabrication and evaluation of light emitting element D10 In Example D3 (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 D10 was produced in the same manner as in Example D3, except that "the low molecular weight compound HTL-5 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 D10. The luminous efficiency at 50 cd / m ² was 1.83 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.14). The luminous efficiency at 200 cd / m ² was 2.12 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.13).

<Example D11> Fabrication and evaluation of light emitting element D11 In Example D4 (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 D11 was produced in the same manner as in Example D4, except that "the low molecular weight compound HTL-5 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 D11. The luminous efficiency at 50 cd / m ² was 2.13 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.17). The luminous efficiency at 200 cd / m ² was 2.61 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.16).

<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 luminous efficiency at 50 cd / m ² was 0.48 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19). The luminous efficiency at 200 cd / m ² was 0.62 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.19).

<Comparative Example CD2> Preparation and evaluation of the light emitting element CD2 The light emitting element CD2 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 CD2. The luminous efficiency at 50 cd / m ² was 0.37 cd / A, and the CIE chromaticity coordinates (x, y) were (0.14, 0.14). The luminous efficiency at 200 cd / m ² was 0.54 cd / A, and the CIE chromaticity coordinates (x, y) were (0.14, 0.14).

<Comparative Example CD3> Fabrication and evaluation of light emitting device CD3 Compound HM-1 was used instead of compound HM-2 in Example D6. Further, the compound EM-1 was used instead of the compound EM-3. Other than that, the light emitting device CD3 was produced in the same manner as in Example D6.

EL light emission was observed by applying a voltage to the light emitting element CD3. The luminous efficiency at 50 cd / m ² was 0.07 cd / A, 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 .

<Comparative Example CD4> Preparation and Evaluation of Light Emitting Element CD4 A light emitting device CD4 was produced in the same manner as in Example D5 except that compound EM-5 was used instead of compound EM-2 in Example D5.

EL light emission was observed by applying a voltage to the light emitting element CD4. The luminous efficiency at 50 cd / m ² was 0.15 cd / A, and the CIE chromaticity coordinates (x, y) were (0.17, 0.20). The luminous efficiency at 200 cd / m ² was 0.20 cd / A, and the CIE chromaticity coordinates (x, y) were (0.17, 0.19).

<Example D12> Fabrication and evaluation of light emitting device D12 A light emitting device D12 was manufactured in the same manner as in Example D5 except that the polymer compound HP-2 was used instead of the compound HM-2 in Example D5. ..

EL light emission was observed by applying a voltage to the light emitting element D12. The luminous efficiency at 100 cd / m ² was 2.19 cd / A, and the CIE chromaticity coordinates (x, y) were (0.16, 0.22).

<Comparative Example CD5> Fabrication and Evaluation of Light Emitting Element CD5 A light emitting device CD5 is used in the same manner as in Example D12 except that the polymer compound HTL-1 is used instead of the polymer compound HTL-3 in Example D12. Made.

EL light emission was observed by applying a voltage to the light emitting element CD5. The luminous efficiency at 100 cd / m ² was 0.99 cd / A, and the CIE chromaticity coordinates (x, y) were (0.15, 0.15).

<Comparative Example CD6> Preparation and Evaluation of Light Emitting Element CD6 A light emitting device CD6 was produced in the same manner as in Example D12 except that compound EM-5 was used instead of compound EM-2 in Example D12.

EL light emission was observed by applying a voltage to the light emitting element CD6. The luminous efficiency at 100 cd / m ² was 1.01 cd / A, and the CIE chromaticity coordinates (x, y) were (0.17, 0.20).

Claims (14)

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 small molecule compound represented by the formula (1) and a host material .
The host material is a polymer compound containing a structural unit represented by the formula (Y).
A light emitting device in which the second organic layer is a layer containing a crosslinked body of a crosslinking material.

[During the ceremony,
Ring R ^1A , ring R ^2A , and ring R ^3A each independently represent an aromatic hydrocarbon ring, and the ring may have a substituent. When a plurality of the substituents 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 atom to which each is bonded.
However, at least one of ring R ^1A , ring R ^2A and ring R ^3A has a group represented by the formula (1-S). ]

[In the formula, Ar ^1S represents an aryl group of the fused ring, and the group may have a substituent. ]

[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 cross-linking material
Claim 1 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. The light emitting element according to.
(Crosslinking 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. When there are a plurality of R ^XLs , they may be the same or different, and when there are a plurality of n ^XLs , 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 at least one 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 of 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.
^LA represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and 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 there are multiple ^LAs , 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. ]

[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.
^KA represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR'-, an oxygen atom or a sulfur atom, and 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 there are multiple ^KAs , 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. ] The light emitting device according to claim 1, wherein the crosslinked material is a small molecule compound represented by the formula (3).

[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 there are multiple Ar ^7s , 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. ] The ring R ^1A , the ring R ^2A , and the ring R ^3A are a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a dihydrophenanthrene ring, a naphthacene ring, a fluorene ring, a spirobifluorene ring, a pyrene ring, and a perylene. The light emitting element according to any one of claims 1 to 5, which is a ring, a chrysene ring, an inden ring, a fluoranthene ring or a benzofluoranthene ring (these rings may have a substituent). The compound according to any one of claims 1 to 6, wherein the compound represented by the formula (1) is a compound represented by the formula (1-A) or a compound represented by the formula (1-B). Light emitting element.

[During the ceremony,
R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A are hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group. , Aryloxy group, monovalent heterocyclic group, substituted amino group or halogen atom, and these groups may have a substituent.
However, at least one of R ^11A , R ^12A , R ^13A , R ^14A , R ^21A , R ^22A , R ^23A , R ^31A , R ^32A and R ^33A is represented by the above formula (1-S). Has a group.
R ^11A and R ^12A , R ^12A and R ^13A , R ^13A and R ^14A , R ^14A and R ^31A , R ^31A and R ^32A , R ^32A and R ^33A , R ^33A and R ^23A , R ^23A and R ^22A , R ^22A . And R ^21A , and R ^21A and R ^11A may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

[During the ceremony,
R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B are hydrogen atoms, alkyl groups, cycloalkyl groups, alkoxy groups, It represents a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups may have a substituent.
However, at least one of R ^11B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21B , R ^22B , R ^23B , R ^31B , R ^32B and R ^33B is the above-mentioned formula (1-). It has a group represented by S).
R ^11B and R ^15B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , R ^18B and R ^14B , R ^14B and R ^31B , R ^31B and R ^32B , R ^32B and R ^33B , R ^33B . And R ^23B , R ^23B and R ^22B , R ^22B and R ^21B , and R ^21B and R ^11B , respectively, may be bonded to form a ring together with the carbon atom to which each is bonded. ] The Ar ^1S 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 (the group may have a substituent) obtained by removing one hydrogen atom directly bonded to a carbon atom constituting the ring from the fluorene ring. The light emitting element according to. The light emitting element according to any one of claims 1 to 8, wherein the maximum peak wavelength of the light emission spectrum of the compound represented by the formula (1) is 380 nm or more and 570 nm or less. The first organic layer further contains at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, an antioxidant and a light emitting material. The light emitting element according to any one of 1 to 9. The light emitting device according to any one of claims 1 to 10, 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 11, wherein the second organic layer is a layer provided between the anode and the first organic layer. 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 small molecule compound represented by the formula (1) and a host material .
The host material is a polymer compound containing a structural unit represented by the formula (Y).
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 device, 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.

[During the ceremony,
Ring R ^1A , ring R ^2A , and ring R ^3A each independently represent an aromatic hydrocarbon ring, and the ring may have a substituent. When a plurality of the substituents 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 atom to which each is bonded.
However, at least one of ring R ^1A , ring R ^2A and ring R ^3A has a group represented by the formula (1-S). ]

[In the formula, Ar ^1S represents an aryl group of the fused ring, and the group may have a substituent. ]

[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 method for manufacturing a light emitting device according to claim 13, wherein the organic layer formed on the crosslinked second organic layer by a wet method is the first organic layer.