JP2019050371A - Light-emitting element - Google Patents

Abstract

To provide a light-emitting element superior in light emission efficiency.SOLUTION: A light-emitting element comprises first and second organic layers provided between positive and negative electrodes. The first organic layer includes: a low-molecular compound including no transition metal, which satisfies at least one of requirements (i) and (ii); and a phosphorescent transition metal complex having dendron. In the light-emitting element, the second organic layer includes a crosslinked body of a high molecular compound having crosslinking groups. Supposing that the total molecular weight of the high molecular compound is X, and the total number of crosslinking groups is Y, the value of (Y×1000)/Xis 0.25 or more. (i) An absolute value of difference in energy level between the lowest triplet excited state and the lowest singlet excited state is less than 0.25 eV. (ii) The low-molecular compound is represented by the formula (T-1). [nis 0 to 5; nis 1 to 10; Aris a substituent amino group or particular monovalent heterocyclic group; Lis an alkylene group, an arylene group or the like; and Arrepresents a particular aromatic hydrocarbon group or a heterocyclic group.]SELECTED DRAWING: None

Description

  The present invention relates to a light emitting device.

Light emitting elements such as organic electroluminescent elements can be suitably used for display and illumination applications, and research and development have been conducted. For example, Patent Document 1 describes a light emitting device having an organic layer containing a polymer compound (P0) having a crosslinking group, and a light emitting layer containing a host material and a phosphorescent transition metal complex. The polymer compound (P0) is a polymer compound having a value of (Y ₁ × 1000) / X ₁ of less than 0.25.

International Publication No. 2015/192941

However, the light emitting element described above does not necessarily have sufficient luminous efficiency.
Then, an object of this invention is to provide the light emitting element which is excellent in luminous efficiency.

The present invention provides the following [1] to [16].
[1]
A light emitting device comprising 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 low-molecular compound containing no transition metal satisfying at least one of the requirements (i) and (ii), and a phosphorescent transition metal complex having dendron,
The second organic layer is a layer containing a crosslinked product of a polymer compound containing a structural unit having a crosslinking group,
Assuming that the sum of the molecular weights of all the constituent units constituting the polymer compound is X ₁ and the sum of the number of crosslinking groups contained in all the constituent units constituting the polymer compound is Y ₁ :

の値が０．２５以上である、前記発光素子。
（i）最低三重項励起状態のエネルギー準位と最低一重項励起状態のエネルギー準位との差の絶対値が０．２５ｅＶ未満である。
（ii）式（Ｔ−１）で表される。

The light emitting element, wherein the value of is 0.25 or more.
(I) The absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is less than 0.25 eV.
(Ii) It is represented by Formula (T-1).

［式中、
ｎ^T1は、０以上５以下の整数を表す。ｎ^T1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^T2は、１以上１０以下の整数を表す。
Ａｒ^T1は、置換アミノ基又は１価の複素環基を表し、該１価の複素環基は、環内に二重結合を有さない窒素原子を含み、且つ、環内に＝Ｎ−で表される基、−Ｃ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）−で表される基、及び、−Ｓ（＝Ｏ）₂−で表される基を含まない１価の複素環基であり、これらの基は置換基を有していてもよい。Ａｒ^T1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^T1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^T1'−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^T1'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^T1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^T2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。
但し、Ａｒ^T1のすべてが置換アミノ基、又は、式（Ｔ１−１Ａ）で表される基である場合、Ａｒ^T2は、環内に＝Ｎ−で表される基を２個以上含む単環の複素環基、環内に−Ｃ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）₂−で表される基及び＝Ｎ−で表される基からなる群より選ばれる少なくとも１つを含む縮合環の複素環基、又は、電子求引性基若しくは環内に−Ｃ（＝Ｏ）−で表される基を含む芳香族炭化水素基であり、これらの基は置換基を有していてもよい。］

[In the formula,
n ^T1 represents an integer of 0 or more and 5 or less. When there are a plurality of n ^{T1 's} , they may be the same or different.
n ^T2 represents an integer of 1 or more and 10 or less.
Ar ^T1 represents a substituted amino group or a monovalent heterocyclic group, the monovalent heterocyclic group containing a nitrogen atom having no double bond in the ring, and = N in the ring a group represented by, -C (= O) - group represented by, -S (= O) - group represented by _{and,, -S (= O) 2} - does not include a group represented by 1 It is a divalent heterocyclic group, and these groups may have a substituent. When a plurality of Ar ^T1 are present, they may be the same or different.
L ^T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR ^T1 '-, an oxygen atom or a sulfur atom, and these groups have a substituent May be R ^T1 ′ 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. When a plurality of L ^T1 are present, they may be the same or different.
Ar ^T2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
However, when all of Ar ^T1 is a substituted amino group or a group represented by formula (T1-1A), Ar ^T2 is a single ring containing two or more groups represented by = N- in the ring Heterocyclic group, a group represented by —C (= O) — in the ring, a group represented by —S (= O) —, a group represented by —S (= O) ₂ — and NN A heterocyclic group of a fused ring containing at least one selected from the group consisting of-, or an electron withdrawing group or an aroma containing a group represented by -C (= O)-within the ring Group hydrocarbon groups, and these groups may have a substituent. ]

［式中、
Ｘ^T1は、単結合、酸素原子、硫黄原子、−Ｎ(Ｒ^XT1)−で表される基、又は、−Ｃ(Ｒ^XT1')₂−で表される基を表す。Ｒ^XT1及びＲ^XT1'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、１価の複素環基、置換アミノ基、ハロゲン原子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^XT1'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原子とともに環を形成していてもよい。
Ｒ^T1、Ｒ^T2、Ｒ^T3、Ｒ^T4、Ｒ^T5、Ｒ^T6、Ｒ^T7及びＲ^T8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、１価の複素環基、置換アミノ基、ハロゲン原子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。］
［２］
前記架橋基が、架橋基Ａ群から選ばれる架橋基である、［１］に記載の発光素子。
（架橋基Ａ群）

[In the formula,
X ^T1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by -N (R ^XT1 )-, or a group represented by -C (R ^XT1 ') _2- . R ^XT1 and R ^XT1 ′ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or A cyano group is represented, and these groups may have a substituent. The plurality of R ^XT1 's may be the same or different, and may be combined with each other to form a ring together with the atoms to which they are attached.
R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 , R ^T7 and R ^T8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may have a substituent. ]
[2]
The light emitting device according to [1], wherein the crosslinking group is a crosslinking group selected from a crosslinking group A group.
(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い。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く、該置換基が複数存在する場合、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。］
［３］
前記架橋基を有する構成単位が、式（２）で表される構成単位又は式（２’）で表される構成単位である、［２］に記載の発光素子。

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5]. When two or more R ^XL exist, they may be the same or different. When there are a plurality of n ^XL , they may be the same or different. * 1 represents a bonding position. These crosslinking groups may have a substituent, and when there are a plurality of such substituents, they may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]
[3]
The light emitting device according to [2], wherein the structural unit having a crosslinking group is a structural unit represented by Formula (2) or a structural unit represented by 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。
Ａｒ³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、前記架橋基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。］

[In the formula,
nA represents an integer of 0 to 5, and n represents 1 or 2. When a plurality of nA are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent It is also good. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A is plurally present, they may be the same or different.
X represents a crosslinking group selected from the aforementioned crosslinking group A group. When two or more X exist, they may be 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。
Ａｒ⁵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。
Ａｒ⁴及びＡｒ⁶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。
Ａｒ⁴、Ａｒ⁵及びＡｒ⁶はそれぞれ、該基が結合している窒素原子に結合している該基以外の基と、直接結合又は酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。
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、前記と同じ意味を表す。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、前記架橋基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、前記架橋基Ａ群から選ばれる架橋基である。］
［４］
前記デンドロンを有する燐光発光性遷移金属錯体が、式（１）で表される金属錯体である、［１］〜［３］のいずれかに記載の発光素子。

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When there are a plurality of 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 heterocyclic ring are directly bonded, and these groups have a substituent It 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 being directly bonded or bonded via an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which the group is bonded It may be done.
K ^A 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 each have a substituent It is also good. R 'represents the same meaning as described above. If K ^A there are a plurality, they may be the same or different.
X 'represents a bridging group selected from the above bridging group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent . When a plurality of X 'are present, they may be the same or different. However, at least one X ′ is a crosslinking group selected from the aforementioned crosslinking group A group. ]
[4]
The light emitting element in any one of [1]-[3] whose phosphorescence transition metal complex which has the said dendron is a metal complex represented by Formula (1).

［式中、
Ｍは、ルテニウム原子、ロジウム原子、パラジウム原子、イリジウム原子又は白金原子を表す。
ｎ¹は１以上の整数を表し、ｎ²は０以上の整数を表す。但し、Ｍがルテニウム原子、ロジウム原子又はイリジウム原子の場合、ｎ¹＋ｎ²は３であり、Ｍがパラジウム原子又は白金原子の場合、ｎ¹＋ｎ²は２である。
Ｅ¹及びＥ²は、それぞれ独立に、炭素原子又は窒素原子を表す。但し、Ｅ¹及びＥ²の少なくとも一方は炭素原子である。Ｅ¹及びＥ²が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
環Ｌ¹は、芳香族複素環を表し、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、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｌ¹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。
環Ｌ²は、芳香族炭化水素環又は芳香族複素環を表し、これらの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、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｌ²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。
環Ｌ¹が有していてもよい置換基と、環Ｌ²が有していてもよい置換基とは、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
環Ｌ¹及び環Ｌ²のうちの少なくとも一つは、デンドロンを有する。
Ａ¹−Ｇ¹−Ａ²は、アニオン性の２座配位子を表す。Ａ¹及びＡ²は、それぞれ独立に、炭素原子、酸素原子又は窒素原子を表し、これらの原子は環を構成する原子であってもよい。Ｇ¹は、単結合、又は、Ａ¹及びＡ²とともに２座配位子を構成する原子団を表す。Ａ¹−Ｇ¹−Ａ²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。］
［５］
前記式（１）で表される金属錯体が、式（１−Ａ）で表される金属錯体である、［４］に記載の発光素子。

[In the formula,
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹ represents an integer of 1 or more, and n ² represents an integer of 0 or more. However, when M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹ + n ² is 3, and when M is a palladium atom or a platinum atom, n ¹ + n ² is 2.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. However, at least one of E ¹ and E ² is a carbon atom. When a plurality of E ¹ and E ² exist, they may be the same or different.
The ring L ¹ represents a heteroaromatic ring, and the ring may have a substituent. When there are a plurality of such substituents, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings L ¹ exist, they may be the same or different.
The ring L ² represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When there are a plurality of such substituents, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings L ² exist, they may be the same or different.
The substituent which ring L ¹ may have and the substituent which ring L ² may have may be bonded to each other to form a ring together with the atoms to which they are attached.
At least one of ring L ¹ and ring L ² has a dendron.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. Each of A ¹ and A ² independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand with A ¹ and A ² . When ^two or more A ¹ -G ¹ -A ² are present, they may be the same or different. ]
[5]
The light emitting device according to [4], wherein the metal complex represented by the formula (1) is a metal complex represented by the formula (1-A).

［式中、
Ｍ、ｎ¹、ｎ²、Ｅ¹及びＡ¹−Ｇ¹−Ａ²は、前記と同じ意味を表す。
環Ｌ^1Aは、ピリジン環、ジアザベンゼン環、アザナフタレン環、ジアザナフタレン環、トリアゾール環又はジアゾール環を表し、これらの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、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｌ^1A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。
Ｅ^21A、Ｅ^22A、Ｅ^23A及びＥ^24Aは、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ^21A、Ｅ^22A、Ｅ^23A及びＥ^24Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。Ｅ^21Aが窒素原子の場合、Ｒ^21Aは存在しない。Ｅ^22Aが窒素原子の場合、Ｒ^22Aは存在しない。Ｅ^23Aが窒素原子の場合、Ｒ^23Aは存在しない。Ｅ^24Aが窒素原子の場合、Ｒ^24Aは存在しない。
Ｒ^21A、Ｒ^22A、Ｒ^23A及びＲ^24A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、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。Ｒ^21A、Ｒ^22A、Ｒ^23A及びＲ^24Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。Ｒ^21AとＲ^22A、Ｒ^22AとＲ^23A、Ｒ^23AとＲ^24A、及び、環Ｌ^1Aが有していてもよい置換基とＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。
但し、環Ｌ^1Aがデンドロンを有するか、或いは、Ｒ^21A、Ｒ^22A、Ｒ^23A及びＲ^24Aのうちの少なくとも１つは、デンドロンである。
環Ｌ^2Aは、ベンゼン環、ピリジン環又はジアザベンゼン環を表す。］
［６］
前記式（１−Ａ）で表される金属錯体が、式（１−Ｂ１）、式（１−Ｂ２）、式（１−Ｂ３）、式（１−Ｂ４）又は式（１−Ｂ５）で表される金属錯体である、［５］に記載の発光素子。

[In the formula,
M, n ¹ , n ² , E ¹ and A ¹ -G ¹ -A ² have the same meaning as described above.
The ring L ^1A represents a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring or a diazole ring, and these rings may have a substituent. When there are a plurality of such substituents, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When two or more rings L ^1A are present, they may be the same or different.
E ^21A , E ^22A , E ^23A and E ^24A each independently represent a nitrogen atom or a carbon atom. When there are a plurality of E ^21A , E ^22A , E ^23A and E ^24A , they may be the same or different. When E ^21A is a nitrogen atom, R ^21A is absent. When E ^22A is a nitrogen atom, R ^22A is absent. When E ^23A is a nitrogen atom, R ^23A is absent. When E ^24A is a nitrogen atom, R ^24A is absent.
R ^21A , R ^22A , R ^23A and R ^24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino A group or a halogen atom is represented, and these groups may have a substituent. When there are a plurality of R ^21A , R ^22A , R ^23A and R ^24A , they may be the same or different. R ^21A and R ^22A , R ^22A and R ^23A , R ^23A and R ^24A , and a substituent which may be possessed by the ring L ^1A and R ^21A respectively combine to form a ring together with the atoms to which they are attached You may form.
However, ring L ^1A has a dendron, or at least one of R ^21A , R ^22A , R ^23A and R ^24A is a dendron.
Ring L ^2A represents a benzene ring, a pyridine ring or a diazabenzene ring. ]
[6]
The metal complex represented by the formula (1-A) is represented by the formula (1-B1), the formula (1-B2), the formula (1-B3), the formula (1-B4) or the formula (1-B5) The light emitting element as described in [5] which is a metal complex represented.

［式中、
Ｍ、ｎ¹、ｎ²、Ｒ^21A、Ｒ^22A、Ｒ^23A、Ｒ^24A及びＡ¹−Ｇ¹−Ａ²は、前記と同じ意味を表す。
ｎ¹¹及びｎ¹²は、それぞれ独立に、１又は２を表す。但し、Ｍがルテニウム原子、ロジウム原子又はイリジウム原子の場合、ｎ¹¹＋ｎ¹²は３であり、Ｍがパラジウム原子又は白金原子の場合、ｎ¹¹＋ｎ¹²は２である。
Ｒ^11B、Ｒ^12B、Ｒ^13B、Ｒ^14B、Ｒ^15B、Ｒ^16B、Ｒ^17B及びＲ^18B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、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。Ｒ^11B、Ｒ^12B、Ｒ^13B、Ｒ^14B、Ｒ^15B、Ｒ^16B、Ｒ^17B及びＲ^18Bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
但し、Ｒ^11B、Ｒ^12B、Ｒ^13B、Ｒ^14B、Ｒ^15B、Ｒ^16B、Ｒ^17B、Ｒ^18B、Ｒ^21A、Ｒ^22A、Ｒ^23A及びＲ^24Aのうち、少なくとも１つはデンドロンである。
式（１−Ｂ１）中、Ｒ^11BとＲ^12B、Ｒ^12BとＲ^13B、Ｒ^13BとＲ^14B、及び、Ｒ^11BとＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。式（１−Ｂ２）中、Ｒ^13BとＲ^14B、Ｒ^13BとＲ^15B、Ｒ^15BとＲ^16B、Ｒ^16BとＲ^17B、Ｒ^17BとＲ^18B、及び、Ｒ^18BとＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。式（１−Ｂ３）中、Ｒ^11BとＲ^12B、Ｒ^12BとＲ^13B、Ｒ^11BとＲ^21A、Ｒ^13BとＲ^14B、Ｒ^13BとＲ^15B、Ｒ^15BとＲ^16B、Ｒ^16BとＲ^17B、Ｒ^17BとＲ^18B、及び、Ｒ^18BとＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。式（１−Ｂ４）中、Ｒ^11BとＲ^18B、Ｒ^14BとＲ^15B、Ｒ^15BとＲ^16B、Ｒ^16BとＲ^17B、Ｒ^17BとＲ^18B、及び、Ｒ^11BとＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。式（１−Ｂ５）中、Ｒ^11BとＲ^12B、Ｒ^12BとＲ^18B、Ｒ^15BとＲ^16B、Ｒ^16BとＲ^17B、Ｒ^17BとＲ^18B、及び、Ｒ^11BとＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］
［７］
前記デンドロンが、式（Ｄ−Ａ）又は式（Ｄ−Ｂ）で表される基である、［１］〜［６］のいずれかに記載の発光素子。

[In the formula,
M, n ¹ , n ² , R ^21A , R ^22A , R ^23A , R ^24A and A ¹ -G ¹ -A ² have the same meanings as described above.
n ¹¹ and n ¹² each independently represent 1 or 2; However, when M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹¹ + n ¹² is 3, and when M is a palladium atom or a platinum atom, n ¹¹ + n ¹² is 2.
R ^11B , R ^12B , R ^13B , R ^14B , R ^15B , R ^16B , R ^17B and R ^18B each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^11B , R ^12B , R ^13B , R ^14B , R ^15B , R ^16B , R ^17B and R ^18B , they may be the same or different.
However, at least one of R ^11B , R ^12B , R ^13B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21A , R ^22A , R ^23A and R ^24A is a dendron.
In the formula (1-B1), R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , and R ^11B and R ^21A respectively bond to form a ring with the atoms to which each is bonded. It may be In the formula (1-B2), ^R13B and ^R14B , ^R13B and ^R15B , ^R15B and ^R16B , ^R16B and ^R17B , ^R17B and ^R18B , and ^R18B and ^R21A respectively bind And may form a ring together with the atoms to which they are attached. Wherein (1-B3), R ^11B and R ^12B, R ^12B and R ^13B, R ^11B and R ^21A, R ^13B and R ^14B, R ^13B and R ^15B, R ^15B and R ^16B, R ^16B and R ^17B, R ^17B and R ^18B and R ^18B and R ^21A may be combined to form a ring together with the atoms to which they are attached. In the formula (1-B4), R ^11B and R ^18B , R ^14B and R ^15B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , and R ^11B and R ^21A are respectively bonded And may form a ring together with the atoms to which they are attached. In the formula (1-B5), R ^11B and R ^12B , R ^12B and R ^18B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , and R ^11B and R ^21A are respectively bonded And may form a ring together with the atoms to which they are attached. ]
[7]
The light emitting device according to any one of [1] to [6], wherein the dendron is a group represented by Formula (D-A) or Formula (D-B).

［式中、
ｍ^DA1、ｍ^DA2及びｍ^DA3は、それぞれ独立に、０以上の整数を表す。
Ｇ^DAは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^DA1、Ａｒ^DA2及びＡｒ^DA3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^DA1、Ａｒ^DA2及びＡｒ^DA3が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^DAは、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。複数あるＴ^DAは、同一でも異なっていてもよい。］

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

［式中、
ｍ^DA1、ｍ^DA2、ｍ^DA3、ｍ^DA4、ｍ^DA5、ｍ^DA6及びｍ^DA7は、それぞれ独立に、０以上の整数を表す。
Ｇ^DAは、窒素原子、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。複数あるＧ^DAは、同一でも異なっていてもよい。
Ａｒ^DA1、Ａｒ^DA2、Ａｒ^DA3、Ａｒ^DA4、Ａｒ^DA5、Ａｒ^DA6及びＡｒ^DA7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^DA1、Ａｒ^DA2、Ａｒ^DA3、Ａｒ^DA4、Ａｒ^DA5、Ａｒ^DA6及びＡｒ^DA7が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^DAは、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。複数あるＴ^DAは、同一でも異なっていてもよい。］
［８］
前記式（Ｄ−Ａ）で表される基が、式（Ｄ−Ａ１）、式（Ｄ−Ａ２）、式（Ｄ−Ａ３）、式（Ｄ−Ａ４）又は式（Ｄ−Ａ５）で表される基である、［７］に記載の発光素子。

[In the formula,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more.
G ^DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. A plurality of G ^DAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. The plurality of ^TDAs may be the same or different. ]
[8]
The group represented by the formula (D-A) is a group represented by formula (D-A1), formula (D-A2), formula (D-A3), formula (D-A4) or formula (D-A5). The light emitting device according to [7], which is a

［式中、
Ｒ^p1、Ｒ^p2、Ｒ^p3及びＲ^p4は、それぞれ独立に、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又はハロゲン原子を表す。Ｒ^p1、Ｒ^p2及びＲ^p4が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
ｎｐ１は、０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０又は１を表し、ｎｐ４は０〜４の整数を表す。複数あるｎｐ１は、同一でも異なっていてもよい。］
［９］
前記式（Ｄ−Ｂ）で表される基が、式（Ｄ−Ｂ１）、式（Ｄ−Ｂ２）、式（Ｄ−Ｂ３）、式（Ｄ−Ｂ４）、式（Ｄ−Ｂ５）又は式（Ｄ−Ｂ６）で表される基である、［７］に記載の発光素子。

[In the formula,
R ^p1 , R ^p2 , R ^p3 and R ^p4 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p1 , R ^p2 and R ^p4 , they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. The plurality of np1 may be the same or different. ]
[9]
The group represented by Formula (D-B) is a group represented by Formula (D-B1), Formula (D-B2), Formula (D-B3), Formula (D-B4), Formula (D-B5) or Formula The light emitting element as described in [7] which is a group represented by (D-B6).

［式中、
Ｒ^p1、Ｒ^p2、Ｒ^p3及びＲ^p4は、それぞれ独立に、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又はハロゲン原子を表す。Ｒ^p1、Ｒ^p2及びＲ^p4が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
ｎｐ１は０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０又は１を表し、ｎｐ４は０〜４の整数を表す。複数あるｎｐ１は同一でも異なっていてもよい。複数あるｎｐ２は、それらは同一でも異なっていてもよい。］
［１０］
前記Ａｒ^T1の少なくとも１つが、式（Ｔ１−１）で表される基である、［１］〜［９］のいずれかに記載の発光素子。

[In the formula,
R ^p1 , R ^p2 , R ^p3 and R ^p4 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p1 , R ^p2 and R ^p4 , they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. Plural np1 may be the same or different. The plurality of np2 may be the same or different. ]
[10]
The light emitting element according to any one of [1] to [9], wherein at least one of the Ar ^T1 is a group represented by Formula (T1-1).

［式中、Ｘ^T1は前記と同じ意味を表す。
環Ｒ^T1及び環Ｒ^T2は、それぞれ独立に、環内に−Ｃ（＝Ｏ）−で表される基を含まない芳香族炭化水素環、又は、環内に＝Ｎ−で表される基、−Ｃ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）−で表される基、及び、−Ｓ（＝Ｏ）₂−で表される基を含まない複素環を表し、これらの環は置換基を有していてもよい。］
［１１］
前記式（T１−１）で表される基が、式（T１−１Ａ）、式（T１−１Ｂ）、式（T１−１Ｃ）又は式（T１−１Ｄ）で表される基である、［１０］に記載の発光素子。

[Wherein, X ^T1 represents the same meaning as described above.
Ring ^RT1 and ring ^RT2 are each independently an aromatic hydrocarbon ring which does not contain a group represented by -C (= O)-in the ring, or a group represented by = N- in the ring And a group represented by -C (= O)-, a group represented by -S (= O)-, and a heterocycle not containing a group represented by -S (= O) _2- , These rings may have a substituent. ]
[11]
The group represented by Formula (T1-1) is a group represented by Formula (T1-1A), Formula (T1-1B), Formula (T1-1C), or Formula (T1-1D), 10].

［式中、
Ｘ^T1は、前記と同じ意味を表す。
Ｘ^T2及びＸ^T3は、それぞれ独立に、単結合、酸素原子、硫黄原子、−Ｎ(Ｒ^XT2)−で表される基、又は、−Ｃ(Ｒ^XT2')₂−で表される基を表す。Ｒ^XT2及びＲ^XT2'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、１価の複素環基、置換アミノ基、ハロゲン原子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^XT2'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原子とともに環を形成していてもよい。
Ｒ^T1、Ｒ^T2、Ｒ^T3、Ｒ^T4、Ｒ^T5、Ｒ^T6、Ｒ^T7、Ｒ^T8、Ｒ^T9、Ｒ^T10、Ｒ^T11及びＲ^T12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、１価の複素環基、置換アミノ基、ハロゲン原子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。］
［１２］
前記Ａｒ^T2が、環内に＝Ｎ−で表される基を２個以上含む、置換基を有していてもよい単環の複素環基である、［１］〜［１１］のいずれかに記載の発光素子。
［１３］
前記遷移金属を含まない低分子化合物が、前記要件（i）及び前記要件（ii）を満たす、［１］〜［１２］のいずれかに記載の発光素子。
［１４］
前記第１の有機層が、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料及び酸化防止剤からなる群より選ばれる少なくとも１種を更に含有する、［１］〜［１３］のいずれかに記載の発光素子。
［１５］
前記第１の有機層と前記第２の有機層とが隣接している、［１］〜［１４］のいずれかに記載の発光素子。
［１６］
前記第２の有機層が、前記陽極及び前記第１の有機層との間に設けられた層である、［１］〜［１５］のいずれかに記載の発光素子。

[In the formula,
X ^T1 represents the same meaning as described above.
X ^T2 and X ^T3 each independently represent a single bond, an oxygen atom, a sulfur atom, a group represented by -N (R ^XT2 )-, or a group represented by -C (R ^XT2 ') _2- Represent. R ^XT2 and R ^XT2 ′ each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or A cyano group is represented, and these groups may have a substituent. Plural R ^XT2 's may be the same or different, and may combine with each other to form a ring together with the atoms to which they are attached.
R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 , R ^T7 , R ^T8 , R ^T9 , R ^T10 , R ^T11 and R ^T12 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group And an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may have a substituent. ]
[12]
Wherein Ar ^T2 is a group represented = by N- in the ring containing 2 or more, a heterocyclic group of single-may have a substituent group ring, any one of [1] to [11] The light emitting element as described in.
[13]
The light emitting element in any one of [1]-[12] that the low molecular weight compound which does not contain the said transition metal satisfy | fills said requirement (i) and said requirement (ii).
[14]
The first organic layer further contains at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant, [1] The light emitting element in any one of [13].
[15]
The light emitting element in any one of [1]-[14] which the said 1st organic layer and the said 2nd organic layer adjoin.
[16]
The light emitting device according to any one of [1] to [15], wherein the second organic layer is a layer provided between the anode and the first organic layer.

  According to the present invention, it is possible to provide a light emitting element which is excellent in light emission efficiency.

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

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

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

The hydrogen atom may be a deuterium atom or a light hydrogen atom.
In the formula representing a metal complex, the solid line representing the bond to 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 number average molecular weight in terms of polystyrene of 1 × 10 ³ to 1 × 10 ⁸ .
The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be another embodiment.
When the polymer compound is used for the preparation of a light emitting device, the terminal group of the polymer compound is preferably a stable group since the light emission characteristics or the brightness life may be reduced if the polymerization active group remains as it is. It is. The terminal group of the polymer compound is preferably a group conjugated with the main chain, and preferably, for example, an aryl group or a monovalent heterocyclic group bonded to the main chain of the polymer compound via a carbon-carbon bond. Can be mentioned.

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

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

The "alkyl group" may be linear or branched. The carbon atom number of the linear alkyl group is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent. The carbon atom number of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent.
The alkyl group may have a substituent, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a 2-butyl group, an isobutyl group, a tert-butyl group, a pentyl group and an isoamyl group 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl And a group in which a 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 (for example, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group , Perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- (3,5-di-hexene) And sylphenyl) propyl and 6-ethyloxyhexyl).
The carbon atom number of the "cycloalkyl group" is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the carbon atom number of the substituent.
The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group and a cyclohexylethyl group.

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

The "alkoxy group" may be linear or branched. The carbon atom number of the linear alkoxy group is usually 1 to 40, preferably 4 to 10, not including the carbon atom number of the substituent. The carbon atom number of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the carbon atom number of the substituent.
The alkoxy group may have a substituent, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, And heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3, 7-dimethyloctyloxy group, lauryloxy group, and a hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, Examples thereof include groups substituted with a cycloalkoxy group, an aryl group, a fluorine atom and the like.
The carbon atom number of the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10, not including the carbon atom number of the substituent.
The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

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

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

The carbon atom number of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, not including the carbon atom number of the substituent.
The monovalent heterocyclic group may have a substituent, and examples thereof include thienyl group, pyrrolyl group, furyl group, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and the like Groups in which a hydrogen atom in any of the groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or the like.

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

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

The "alkenyl group" may be linear or branched. The carbon atom number of the linear alkenyl group is usually 2 to 30, preferably 3 to 20, not including the carbon atom number of the substituent. The carbon atom number of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the carbon atom number of the substituent.
The carbon atom number of the "cycloalkenyl group" is usually 3 to 30, preferably 4 to 20, not including the carbon atom number of the substituent.
The alkenyl group and cycloalkenyl group may have a substituent, and examples thereof include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4- Examples include pentenyl group, 1-hexenyl group, 5-hexenyl group, 7-octenyl group, and groups in which these groups have a substituent.

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

The "arylene group" means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The carbon atom number of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the carbon atom number of the substituent.
The arylene group may have a substituent, and examples thereof include phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrendiyl group, dihydrophenanthrendiyl group, naphthacene diyl group, fluorenediyl group, pyrene diyl group, perylene di group, There may be mentioned a chrysendiyl group and a group in which these groups have a substituent, and preferably a group represented by the formula (A-1) to the formula (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

［式中、Ｒ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ともに環を形成していてもよい。］

[Wherein, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. Plural R and R ^a may be the same as 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 carbon atom number of the divalent heterocyclic group is usually 2 to 60, preferably 3 to 20, and more preferably 4 to 15, not including the carbon atom number of the substituent.
The divalent heterocyclic group may have a substituent, and examples thereof include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, and the like. Preferred are dihydroacridines, furans, thiophenes, azoles, diazoles and triazoles, and divalent groups in which two hydrogen atoms of hydrogen atoms directly bonded to ring carbon atoms or hetero atoms are removed, preferably Are groups represented by formulas (AA-1) to (AA-34). The 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。］

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

  The “crosslinking group” is a group capable of generating a new bond by being subjected to heat treatment, ultraviolet irradiation treatment, near ultraviolet irradiation treatment, visible light irradiation treatment, infrared irradiation treatment, radical reaction, etc. Preferred are crosslinking groups represented by formulas (XL-1) to (XL-19) of the crosslinking group A group.

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

  "Dendron" is a group having a regular tree-like branched structure in which an atom or a ring is a branch point. As a metal complex having a dendron as a partial structure (hereinafter, also referred to as a “metal complex having a dendron”), for example, WO 02/067343, JP 2003-231692 A, WO 2003 / Examples of such a structure include those described in US Pat. In the present specification, the aryl group, the monovalent heterocyclic group and the substituted amino group may be dendron. The dendron is preferably a group represented by formula (DA) or formula (DB).

[Group Represented by Formula (DA) or Formula (DB)]
m ^{DA1 to} m ^DA7 are usually integers of 10 or less, preferably 5 or less, more preferably 2 or less, and further preferably 0 or 1. It is preferable that m ^{DA2 to} m ^DA7 be the same integer.

G ^DA is preferably an aromatic hydrocarbon group or a heterocyclic group, more preferably a hydrogen directly bonded to a carbon atom or nitrogen atom constituting a ring from a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring or a carbazole ring It is a group formed by removing 3 atoms, and these groups may have a substituent.
The substituent that G ^DA may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and more preferably an alkyl group, It is a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.
G ^DA is preferably a group represented by Formula (GDA-11) to Formula (GDA-15), more preferably a group represented by Formula (GDA-11) to Formula (GDA-14) And more preferably a group represented by the formula (GDA-11) or the formula (GDA-14).

［式中、
＊は、式(D-A)におけるＡｒ^DA1、式(D-B)におけるＡｒ^DA1、式(D-B)におけるＡｒ^DA2、または、式(D-B)におけるＡｒ^DA3との結合を表す。
＊＊は、式(D-A)におけるＡｒ^DA2、式(D-B)におけるＡｒ^DA2、式(D-B)におけるＡｒ^DA4、または、式(D-B)におけるＡｒ^DA6との結合を表す。
＊＊＊は、式(D-A)におけるＡｒ^DA3、式(D-B)におけるＡｒ^DA3、式(D-B)におけるＡｒ^DA5、または、式(D-B)におけるＡｒ^DA7との結合を表す。
Ｒ^DAは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基または１価の複素環基を表し、これらの基は更に置換基を有していてもよい。Ｒ^DAが複数ある場合、それらは同一でも異なっていてもよい。］

[In the formula,
* Is, Ar ^DA1 in the formula (DA), Ar ^DA1 in the formula (DB), Ar in formula (DB) ^DA2, or represents a bond between Ar ^DA3 in the formula (DB).
** is, Ar ^DA2 in the formula (DA), Ar ^DA2 in the formula (DB), or Ar ^DA4, in the formula (DB), represents a bond between Ar ^DA6 in the formula (DB).
*** is, Ar ^DA3 in the formula (DA), Ar ^DA3 in the formula (DB), or Ar ^DA5, in the formula (DB), represents a bond between Ar ^DA7 in formula (DB).
R ^DA 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 further have a substituent. When there are a plurality of ^RDAs , they may be the same or different. ]

R ^DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have a substituent May be

Ar ^{DA1 to} Ar ^DA7 are preferably a phenylene group, a ^fluorenediyl group or a carbazole diyl group, more preferably a group represented by the formula (ArDA-1) to the formula (ArDA-5), further preferably Is a group represented by the formula (ArDA-1) to the formula (ArDA-3), particularly preferably a group represented by the formula (ArDA-2), and these groups each have a substituent It is also good.

［式中、
Ｒ^DAは、前記と同じ意味を表す。
Ｒ^DBは、水素原子、アルキル基、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^DBが複数ある場合、それらは同一でも異なっていてもよい。］

[In the formula,
R ^DA has the same meaning as described above.
R ^DB 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. When there are multiple R ^DBs , they may be the same or different. ]

R ^DB is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group, The group may have a substituent.

Examples of Ar ^DA1 to Ar ^DA7 substituent which may be possessed and preferred ranges are the same as examples and preferred ranges of the substituents which may be possessed by G ^DA.

T ^DA is preferably a group represented by Formula (TDA-1) to Formula (TDA-3), and more preferably a group represented by Formula (TDA-1).

［式中、Ｒ^DA及びＲ^DBは、前記と同じ意味を表す。］

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

The group represented by Formula (DA) is preferably a group represented by Formula (D-A1) to Formula (D-A5), more preferably Formula (D-A1) or Formula (D-A3) Or a group represented by formula (D-A5), more preferably a group represented by formula (D-A1), formula (D-A3) or formula (D-A5).
The group represented by Formula (DB) is preferably a group represented by Formula (D-B1) to Formula (D-B6), more preferably Formula (D-B1), Formula (D-B3) Or a group represented by the formula (D-B5), more preferably a group represented by the formula (D-B1).

The alkyl group or cycloalkyl group in R ^{p1 to} R ^p6 is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a cyclohexyl group or a tert-octyl group.

The alkoxy group or cycloalkoxy group in R ^{p1 to} R ^p6 is preferably a methoxy group, a 2-ethylhexyloxy group or a cyclohexyloxy group.

R ^{p1 to} R ^p6 are preferably an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent, and more preferably, which may have a substituent It is an alkyl group, more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group.

  As the dendron, for example, a group represented by Formula (D-A-1) to Formula (D-A-12) and a group represented by Formula (D-B-1) to Formula (D-B-7) Groups are mentioned.

［式中、Ｒ^Dは、水素原子、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、ヘキシル基、２−エチルヘキシル基、ｔｅｒｔ−オクチル基、シクロヘキシル基、メトキシ基、２−エチルヘキシルオキシ基又はシクロへキシルオキシ基を表す。Ｒ^D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。］

[Wherein, R ^D is a hydrogen atom, methyl group, ethyl group, isopropyl group, tert-butyl group, hexyl group, 2-ethylhexyl group, tert-octyl group, cyclohexyl group, methoxy group, 2-ethylhexyloxy group or Represents a cyclohexyloxy group. If R ^D is plurally present, they may be the same or different. ]

^RD is preferably a hydrogen atom, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or a tert-octyl group.

<Light emitting element>
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, wherein the first organic layer is And a layer containing a low-molecular compound containing no transition metal satisfying at least one of the requirements (i) and (ii), and a phosphorescent transition metal complex having a dendron, wherein the second organic layer is It is a layer containing a crosslinked product of a polymer compound containing a constituent unit having a crosslinking group, and the total of the molecular weights of all constituent units constituting the polymer compound is X _1, and all constituent units constituting the polymer compound Let Y ₁ be the sum of the number of crosslinking groups that

の値が０．２５以上であり、前記発光素子である。

Of the light emitting element is 0.25 or more.

Examples of the method of forming the first organic layer and the second organic layer include dry methods such as vacuum deposition, and wet methods such as spin coating and inkjet printing, with wet methods being preferable.
When the first organic layer is formed by a wet method, it is preferable to use a first ink described later.

  When the second organic layer is formed by a wet method, it is preferable to use a second ink described later. After forming the second organic layer, the polymer compound containing a structural unit having a crosslinking group contained in the second organic layer can be crosslinked by heating or light irradiation. It is preferable to crosslink the polymer compound containing the structural unit having a crosslinking group contained in the second organic layer. When the polymer compound containing a structural unit having a crosslinking group is crosslinked (a crosslinked product of a polymer compound containing a structural unit having a crosslinking group) and is contained in the second organic layer, the second organic layer Is substantially insolubilized 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 260 ° C., more preferably 130 ° C. to 230 ° C., still more preferably 180 ° C. to 210 ° C. .
The heating time is usually 0.1 minutes to 1000 minutes, preferably 0.5 minutes to 500 minutes, more preferably 1 minute to 120 minutes, and still more preferably 10 minutes to 60 minutes.

  The type of light used for light irradiation is, for example, ultraviolet light, near ultraviolet light, or visible light.

  As an analysis method of the component contained in the first organic layer or the second organic layer, for example, a device such as chemical separation analysis such as extraction, infrared spectroscopy, nuclear magnetic resonance spectroscopy, mass spectrometry, etc. Analysis methods include analysis methods combining chemical separation analysis methods and instrumental analysis methods.

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

<Phosphorescent transition metal complex having dendron>
The “phosphorescent transition metal complex” usually means a compound which exhibits phosphorescence at room temperature (25 ° C.), preferably a metal complex which emits light from a triplet excited state at room temperature. The metal complex that emits light from this triplet excited state has a central metal atom and a ligand.

  The central metal atom includes, for example, a metal atom having an atomic number of 40 or more, which has spin-orbit interaction in the complex and can cause intersystem crossing between a singlet state and a triplet state. As a metal atom, a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, and a platinum atom are mentioned, for example, Since the luminous efficiency of the light emitting element of this invention is more excellent, Preferably it is an iridium atom or a platinum atom.

  As the ligand, for example, a neutral or anionic monodentate ligand which forms at least one kind of bond selected from the group consisting of a coordinate bond and a covalent bond with a central metal atom, or Neutral or anionic polydentate ligands can be mentioned. The bond between the central metal atom and the ligand includes, for example, metal-nitrogen bond, metal-carbon bond, metal-oxygen bond, metal-phosphorus bond, metal-sulfur bond and metal-halogen bond. The polydentate ligand usually means a bidentate to six-dentate ligand.

[Metal Complex Represented by Formula (1)]
The phosphorescent transition metal complex having dendron is preferably a metal complex represented by the formula (1) because the light emission efficiency of the light emitting device of the present invention is more excellent.

M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the light emission efficiency of the light emitting device of the present invention is more excellent.
When M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹ is preferably 2 or 3, and more preferably 3.
When M is a palladium atom or a platinum atom, n ¹ is preferably 2.
E ¹ and E ² are preferably carbon atoms.

The carbon atom number of the aromatic heterocyclic ring in the ring L ¹ is usually 2 to 60, preferably 3 to 30, and more preferably 4 to 15, not including the carbon atom number of the substituent. The ring L ¹ is preferably a 5-membered aromatic heterocycle or a 6-membered aromatic heterocycle, and is a 5-membered aromatic heterocycle having one or more and four or less nitrogen atoms as a constituent atom or one More preferably, it is a 6-membered aromatic heterocyclic ring having a nitrogen atom of 4 or less as a constituent atom, and these rings may have a substituent. However, when ring L ¹ is a six-membered aromatic heterocycle, E ¹ is preferably a carbon atom.
The ring L ¹ includes, for example, diazole ring, triazole ring, tetrazole ring, pyridine ring, diazabenzene ring, triazine ring, azanaphthalene ring and diazanaphthalene ring, preferably pyridine ring, diazabenzene ring, azanaphthalene ring A diazanaphthalene ring, a triazole ring or a diazole ring, more preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, and even more preferably a pyridine ring, a quinoline ring or an isoquinoline ring, These rings may have a substituent.

The number of carbon atoms in the aromatic hydrocarbon ring in the ring L ² is not including the carbon atom number of substituent is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18. The aromatic hydrocarbon ring in the ring L ² includes a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring and a ring formed by condensing 2 to 5 of these rings. The light emitting device of the present invention is more excellent in light emission efficiency, and is preferably a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring or dihydrophenanthrene ring, more preferably a benzene ring, fluorene ring or dihydrophenanthrene ring, and further preferably Is a benzene ring, and these rings may have a substituent.
The carbon atom number of the aromatic heterocycle in ring L ² is usually 2 to 60, preferably 3 to 15, not including the carbon atom number of the substituent. Examples of the aromatic heterocyclic ring in the ring L ² include a pyrrole ring, a diazole ring, a furan ring, a thiophene ring, a pyridine ring, a diazabenzene ring, and a ring having one or more and five or less aromatic rings fused to these rings. Preferably, a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, an indole ring, a benzofuran ring, a benzothiophene ring, a carbazole ring, an azacarbazole ring, a diazacarbazole because the light emission efficiency of the light emitting device of the invention is more excellent. Ring, dibenzofuran ring or dibenzothiophene ring, more preferably pyridine ring, diazabenzene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring, still more preferably pyridine ring or diazabenzene ring, and these rings are substituted It may have a group. When ring R ² is a 6-membered aromatic heterocycle, E ² is preferably a carbon atom.
The ring L ² is preferably a benzene ring, a fluorene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring because the light emitting efficiency of the light emitting device of the present invention is further excellent. Preferably, it is a benzene ring, a pyridine ring or a diazabenzene ring, more preferably a benzene ring, and these rings may have a substituent.

“At least one of ring L ¹ and ring L ² has a dendron” is an atom (preferably a carbon atom or a ring atom constituting at least one ring of a plurality of ring L ¹ and ring L ² ) It means that some or all of hydrogen atoms directly bonded to the nitrogen atom) are substituted by dendron. In the metal complex represented by formula (1), wherein ring L ¹ and the ring L ² there are a plurality of ring L ¹ and the ring L ² there are a plurality, at least one but may have a dendron Since the light emitting device of the present invention is more excellent in luminous efficiency, all of the plurality of rings L ¹ , all of the plurality of rings L ² , or all of the plurality of rings L ¹ and rings L ² are dendrons. It is preferable to have, and it is more preferable that all of the plurality of ring L ¹ or all of the plurality of ring L ² have dendron.

The substituent which ring L ¹ and ring L ² may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, It is a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an aryl group, a monovalent heterocyclic group or It is a substituted amino group, and these groups may further have a substituent.

The aryl group in the substituent which may be possessed by ring L ¹ and ring L ² is preferably a phenyl group, a naphthyl group, a phentrenyl group, a dihydrophentrenyl group or a fluorenyl group, and a phenyl group or a fluorenyl group Is more preferable, a phenyl group is more preferable, and these groups may have a substituent.
The monovalent heterocyclic group in the substituent which may be possessed by ring L ¹ and ring L ² is pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, dibenzofuranyl group, dibenzothienyl group, Carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group is preferable, and pyridyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothienyl group or carbazolyl group is more preferable, pyridyl group, pyrimidinyl group The group or the triazinyl group is more preferable, the triazinyl group is particularly preferable, and these groups may have a substituent.
In the substituted amino group in the substituent which ring L ¹ and ring L ² may have, as a substituent that the amino group has, an aryl group or a monovalent heterocyclic group is preferable, and an aryl group is more preferable, Groups may further have a substituent. The example and the preferable range of the aryl group in the substituent which an amino group has are the same as the example and the preferable range of the aryl group in the substituent which the ring L ¹ and the ring L ² may have. The example and the preferred range of the monovalent heterocyclic group in the substituent which the amino group has is the same as the example and the preferred range of the monovalent heterocyclic group in the substituent which the ring L ¹ and the ring L ² may have. It is.

In the substituents that ring L ¹ and ring L ² may have, at least one of the aryl group, the monovalent heterocyclic group and the substituted amino group is preferably a dendron.

The substituent which the substituent which ring L ¹ and ring L ² may optionally have may further have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group. It is an oxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably It is an alkyl group or an aryl group, and these groups may further have a substituent.

When a plurality of substituents which may be possessed by the ring L ¹ are present, they are preferably bonded to each other so as not to form a ring with the atoms to which they are bonded. When a plurality of substituents which may be possessed by the ring L ² are present, they are preferably bonded to each other so as not to form a ring with the atoms to which they are bonded. It is preferable that the substituent which the ring L ¹ may have and the substituent which the ring L ² may have are bonded to each other and do not form a ring with the atoms to which they are bonded.

[Anionic bidentate ligand]
Examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² include a ligand represented by the following formula. . However, the anionic bidentate ligand represented by A ¹ -G ¹ -A ² is different from the ligand whose number is defined by the index n ¹ .

［式中、＊は、Ｍと結合する部位を表す。］

[Wherein, * represents a site binding to M. ]

  The metal complex represented by the formula (1) is preferably a metal complex represented by the formula (1-A) because the light emission efficiency of the light emitting device of the present invention is more excellent.

The ring L ^1A is preferably a pyridine ring, a diazabenzene ring, an azanaphthalene ring or a diazanaphthalene ring, and more preferably a pyridine ring, a quinoline ring or an isoquinoline ring, because the light emitting efficiency of the light emitting device of the present invention is more excellent. These rings may have a substituent.
The examples and the preferred ranges of the substituent which the ring L ^1A may have are the same as the examples and the preferred range of the substituent which the ring L ¹ and the ring L ² may have.
When a plurality of substituents that the ring L ^1A may have are present, they are preferably bonded to each other and do not form a ring with the atoms to which they are bonded.

When ring L ^2A is a pyridine ring, a pyridine ring in which E ^21A is a nitrogen atom, a pyridine ring in which E ^22A is a nitrogen atom, or a pyridine ring in which E ^23A is a nitrogen atom is preferable, and E ^22A is a nitrogen atom Certain pyridine rings are more preferred.
When ring L ^2A is a diazabenzene ring, a pyrimidine ring wherein E ^21A and E ^23A is a nitrogen atom or a pyrimidine ring wherein E ^22A and E ^24A are a nitrogen atom is preferable, and E ^22A and E ^24A are a nitrogen atom The pyrimidine ring is more preferred.
The ring L ^2A is preferably a benzene ring.
E ^{21A to} E ^24A are preferably carbon atoms.

R ^{21A to} R ^24A are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, since the luminous efficiency of the light emitting device of the present invention is more excellent. Preferably, they are a hydrogen atom, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.
R ^21A and R ^24A are more preferably hydrogen atoms.

When ring L ^2A has a dendron, it is preferable that R ^22A or R ^23A be a dendron, and it is more preferable that R ^22A be a dendron.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^{21A to} R ^24A are respectively the aryl group in the substituent that the ring L ¹ and the ring L ² may have, and the monovalent group. And the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.
Examples and preferred ranges of the substituent which may be possessed by R ^{21A to} R ^24A are the examples of the substituent which the substituent which the ring L ¹ and the ring L ² may optionally have may further have and It is the same as the preferred range.
R ^21A and R ^22A , R ^22A and R ^23A , R ^23A and R ^24A , and a substituent which may be possessed by the ring L ^1A and R ^21A respectively combine to form a ring together with the atoms to which they are attached It is preferable not to form.

  The metal complex represented by the formula (1-A) is preferably represented by the formula (1-A1) to the formula (1-A4) or the formula (1-B1) because the light emitting efficiency of the light emitting device of the present invention is more excellent. A metal complex represented by the formula (1-B5), more preferably a metal complex represented by the formula (1-B1) to the formula (1-B5), still more preferably the formula (1-B1) And a metal complex represented by the formula (1-B3), particularly preferably a metal complex represented by the formula (1-B1).

  [Metal Complex Represented by Formula (1-A1) to Formula (1-A4)]

［式中、Ｍ、ｎ¹、ｎ²、Ｒ^21A〜Ｒ^24A及びＡ¹−Ｇ¹−Ａ²は、前記と同じ意味を表す。
Ｒ^11A〜Ｒ^13A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、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。Ｒ^11A〜Ｒ^13Aが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
式（１−Ａ１）中、Ｒ^11AとＲ^21Aとは互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。式（１−Ａ２）中、Ｒ^12AとＲ^13Aとは互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。式（１−Ａ３）及び式（１−Ａ４）中、Ｒ^11AとＲ^12A、Ｒ^12AとＲ^13A、及び、Ｒ^11AとＲ^21Aは、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。］

[Wherein, M, n ¹ , n ² , R ^{21A to} R ^24A and A ¹ -G ¹ -A ² represent the same meaning as described above.
R ^{11A to} R ^13A each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom These groups may have a substituent. When there are a plurality of R ^{11A to} R ^13A , they may be the same or different.
In formula (1-A1), R ^11A and R ^21A may be bonded to each other to form a ring together with the atoms to which each is bonded. In formula (1-A2), R ^12A and R ^13A may be bonded to each other to form a ring together with the atoms to which each is bonded. In formulas (1-A3) and (1-A4), R ^11A and R ^12A , R ^12A and R ^13A , and R ^11A and R ^21A respectively combine to form a ring with the atoms to which each is attached It may be done. ]

In formulas (1-A1) and (1-A3), R ^11A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group or a monovalent group The heterocyclic group is more preferably an aryl group, and these groups may have a substituent.
In formula (1-A3), R ^12A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and more preferably a hydrogen atom or an alkyl group Or an aryl group, more preferably a hydrogen atom, and these groups may have a substituent.

In formulas (1-A2) and (1-A4), R ^12A is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and more preferably an aryl group or a monovalent group The heterocyclic group is more preferably an aryl group, and these groups may have a substituent.
In formula (1-A4), R ^11A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and more preferably a hydrogen atom or an alkyl group Or an aryl group, more preferably a hydrogen atom, and these groups may have a substituent.

In formulas (1-A1) to (1-A4), R ^13A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably Is a hydrogen atom, an alkyl group or an aryl group, more preferably a hydrogen atom, and these groups may have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^{11A to} R ^13A are respectively the aryl group in the substituent which the ring L ¹ and the ring L ² may have, and the monovalent group. And the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.
Examples and preferred ranges of the substituent which may be possessed by R ^{11A to} R ^13A are the examples of the substituent which the substituent which the ring L ¹ and the ring L ² may have may further have and It is the same as the preferred range.

In formulas (1-A1) to (1-A4), at least one of R ^{21A to} R ^24A is preferably a dendron, more preferably R ^22A or R ^23A is a dendron, and R ^22A is a dendron. It is further preferred that

In formulas (1-A1) to (1-A4), R ^11A and R ^12A , R ^12A and R ^13A , and R ^11A and R ^21A respectively combine to form a ring with the atoms to which each is attached Preferably not.

[Metal Complex Represented by Formula (1-B1) to Formula (1-B5)]
R ^{11B to} R ^18B are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, because the light emitting efficiency of the light emitting device of the present invention is more excellent. Preferably, they are a hydrogen atom, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

R ^11B and R ^{14B to} R ^18B are preferably hydrogen atoms because they facilitate the synthesis of metal complexes, and these groups may have a substituent.
R ^12B is preferably a hydrogen atom or dendron, more preferably a hydrogen atom, because these compounds further enhance the luminous efficiency of the light emitting device of the present invention, and these groups may have a substituent.
R ^{13 B} is preferably a hydrogen atom or dendron because the light emission efficiency of the light emitting device of the present invention is further excellent, and these groups may have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^{11B to} R ^18B are respectively an aryl group in a substituent which may be possessed by the ring L ¹ and the ring L ² , a monovalent group And the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.
Examples and preferred ranges of the substituent which may be possessed by R ^{11B to} R ^18B are the examples of the substituent which the substituent which the ring L ¹ and the ring L ² may optionally have may further have and It is the same as the preferred range.

In the formula (1-B1), at least one of R ^{11B to} R ^14B and R ^{21A to} R ^24A is a dendron, and the light emission efficiency of the light emitting device of the present invention is more excellent. Therefore, R ^12B , R ^13B , R ^22A and It is preferred that at least one of R ^23A is dendron, more preferably at least one of R ^13B and R ^22A is dendron, and still more preferably, R ^13B or R ^22A is dendron.

In the formula (1-B2), at least one of R ^{13B to} R ^18B and R ^{21A to} R ^24A is a dendron, and the light emission efficiency of the light emitting device of the present invention is more excellent. Thus, R ^13B , R ^22A and R ^23A are preferable. It is preferred that at least one be dendron, more preferred that at least one of R ^22A and R ^23A be dendron, and even more preferred that R ^22A be dendron.

In the formula (1-B3), at least one of R ^{11B to} R ^18B and R ^{21A to} R ^24A is a dendron, and the light emission efficiency of the light emitting device of the present invention is more excellent. Therefore, R ^12B , R ^13B , R ^22A and It is preferred that at least one of R ^23A is dendron, more preferably at least one of R ^13B and R ^22A is dendron, and still more preferably, R ^13B or R ^22A is dendron.

Wherein (1-B4), at least one of R ^11B, R ^14B ~R ^18B and R ^21A to R ^24A are dendron, the emission efficiency of the light-emitting device of the present invention is more excellent, the R ^22A and R ^23A it is preferred that at least one is a dendron, more preferably at least one of R ^22A is dendron, more preferably R ^22A is dendron.

Wherein ^{(1-B5), R 11B} , R 12B, at least one of R ^15B to R ^18B and R ^21A to R ^24A are dendron, the emission efficiency of the light-emitting device of the present invention is more excellent, R ^22A and preferably, at least one of R ^23A is a dendron, more preferably at least one of R ^22A is dendron, more preferably R ^22A is dendron.

R ^{11 B} and R ^{12 B} , R ^{12 B} and R ^{13 B} , R ^{13 B} and R ^{14 B} , R ^{11 B} and R ^{21 A} , R ^{13 B} and R ^{15 B} , R ^{15 B} and R ^{16 B in the} formulas (1-B1) to (1-B5) , R ^16B and R ^17B , R ^17B and R ^18B , R ^18B and R ^21A , R ^11B and R ^18B , R ^14B and R ^15B , and R ^12B and R ^18B respectively bind to atoms to which they are bonded It is preferred not to form a ring together with

  Examples of phosphorescent transition metal complexes having dendrons include metal complexes represented by the following formula.

Phosphorescent transition metal complexes having dendrons are described, for example, in "Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)", "Journal of the American Chemical Society, Vol. 106, 6647-6653 (1984). ], JP 2004-530254 A, JP 2008-179617 A, JP 2011-105701 A, JP 2007-504272 A, WO 2006/121811, JP 2013-147450 A). It can synthesize | combine according to the method described in Unexamined-Japanese-Patent No. 2014-224101.
It is preferable that the low molecular weight compound (hereinafter referred to as “compound (T)”) containing no transition metal contained in the first organic layer is a thermally activated delayed fluorescence (TADF) compound.
The molecular weight of the compound (T) is usually 1 × 10 ² to 1 × 10 ⁴ , preferably 2 × 10 ^{2 to} 5 × 10 ³ , more preferably 3 × 10 ^{2 to} 3 × 10 ³ , More preferably, it is 5 × 10 ^{2 to} 1.5 × 10 ³ .

In the requirement (i), the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state (hereinafter referred to as “ΔE _ST ”) is the light emission of the light emitting device of the present invention Since the efficiency is more excellent, it is preferably 0.20 eV or less, more preferably 0.16 eV or less, and still more preferably 0.13 eV or less. Further, ΔE _ST is preferably 0.001 eV or more, more preferably 0.005 eV or more, still more preferably 0.01 eV or more, particularly preferably 0.015 eV or more, particularly preferably 0. It is 05 eV or more.

Calculation of the value of ΔE _ST of the compound is structural optimization of the ground state of the compound by density functional theory at B3LYP level. At that time, 6-31G * is used as a basis function. Then, using the obtained structure-optimized structure, ΔE _ST of the compound is calculated by the time-dependent density functional method of B3LYP level. However, when 6-31G * contains an unusable atom, LANL2DZ is used for the atom. In addition, as a quantum chemistry calculation program, it calculates using Gaussian09.

In the requirement (ii), ΔE _ST of the compound represented by the formula (T-1) is usually 0.60 eV or less, and the light emission efficiency of the light emitting device of the present invention is more excellent. More preferably, it is 0.20 eV or less, More preferably, it is 0.16 eV or less. Further, ΔE _ST of the compound represented by the formula (T-1) is usually 0.0001 eV or more, preferably 0.001 eV or more, more preferably 0.005 eV or more, and still more preferably 0. .01 eV or more, particularly preferably 0.015 eV or more, and particularly preferably 0.05 eV or more.

n ^T1 is preferably an integer of 0 or more and 3 or less, more preferably 0 or 1, because the light emission efficiency of the light emitting element of the present invention is more excellent.
n ^T2 is preferably an integer of 1 or more and 5 or less, more preferably 1 or 2, because the light emission efficiency of the light emitting element of the present invention is more excellent.
The “nitrogen atom having no double bond” means a nitrogen atom having only a single bond between the nitrogen atom and all atoms bonded to the nitrogen atom.
“Containing a nitrogen atom having no double bond in the ring” means —N (—R ^N ) — (wherein, R ^N represents a hydrogen atom or a substituent) in the ring or a formula:

で表される基を含むことを意味する。

Is meant to include the group represented by

A group represented by = N-, a group represented by -C (= O)-, and -S (= O)-which contains a nitrogen atom having no double bond in the ring and In the monovalent heterocyclic group not including the group represented and the group represented by -S (= O) _2- (hereinafter referred to as "monovalent donor type heterocyclic group"), the ring is constituted. The number of nitrogen atoms having no double bond is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3, and still more preferably 1 or 2.

  In the monovalent donor-type heterocyclic group, the number of carbon atoms constituting the ring is usually 2 to 60, preferably 5 to 40, and more preferably 10 to 25.

The monovalent donor type heterocyclic group includes, for example, pyrrole ring, indole ring, carbazole ring, 9,10-dihydroacridine ring, 5,10-dihydrophenazine ring, phenoxazine ring, phenothiazine ring, indolocarbazole ring, 1 hydrogen atom directly bonded to a carbon atom or hetero atom constituting a ring from an indenocarbazole ring, or a ring in which one or more and five or more aromatic hydrocarbon rings and / or heterocycles are fused to these heterocycles These groups may have a substituent. However, the aromatic hydrocarbon ring which may be fused to the heterocyclic ring is an aromatic hydrocarbon ring which does not contain a group represented by -C (= O)-in the ring. The heterocycle which may be fused to the heterocycle is a group represented by = N-, a group represented by -C (= O)-, a group represented by -S (= O)-in the ring, And a heterocycle which does not contain a group represented by -S (= O) _2- .

The number of carbon atoms of "an aromatic hydrocarbon ring which does not contain a group represented by -C (= O)-in the ring" is usually 6 to 60, preferably 6 to 60, not including the number of carbon atoms of a substituent, Is 6 to 30, and more preferably 6 to 18.
As an aromatic hydrocarbon ring which does not contain the group represented by -C (= O)-in the ring, for example, a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring and these rings Is a ring in which 2 to 5 are fused, preferably a benzene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring or a dihydrophenanthrene ring, and more preferably a benzene ring, a fluorene ring or It is a spirobifluorene ring, more preferably a benzene ring or a fluorene ring, and these rings may have a substituent.

“In the ring, a group represented by NN—, a group represented by —C (OO) —, a group represented by —S (= O) —, and —S (= O) ₂ — The carbon atom number of the heterocycle which does not contain the represented group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the carbon atom number of the substituent. .
In the ring, a group represented by = N-, a group represented by -C (= O)-, a group represented by -S (= O)-, and a table represented by -S (= O) _2- And heterocyclic groups not containing a substituted group include pyrrole ring, furan ring, thiophene ring, indole ring, benzofuran ring, benzothiophene ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, dibenzosilole ring, dibenzophosphole ring, phenoxy Sazine ring, phenothiazine ring, 9,10-dihydroacridine ring, 5,10-dihydrophenazine ring, aromatic hydrocarbon ring which does not contain a group represented by -C (= Z ^T1 )-in the ring on these rings And rings in which one or more and five or less are fused, and rings in which these rings are fused two or more and five or less, preferably carbazole ring, dibenzofuran ring, dibenzothiophene ring, phenoxazine Ring, phenothiazine ring, 9,10-dihydroacridine ring or 5,10-dihydrophenazine ring, more preferably a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these rings have a substituent It is also good.

  A monovalent donor-type heterocyclic group is preferably a carbazole ring, a 9,10-dihydroacridine ring, a 5,10-dihydrophenazine ring, a phenoxazine ring, a phenothiazine because the luminous efficiency of the light emitting device of the present invention is more excellent. A ring, an indolocarbazole ring or an indenocarbazole ring excluding one hydrogen atom directly bonded to a carbon atom or hetero atom constituting the ring, more preferably a carbazole ring, an indolocarbazole ring or It is a group obtained by removing one hydrogen atom directly bonded to a carbon atom or hetero atom constituting a ring from a nocarbazole ring, and these groups may have a substituent.

Examples and preferred ranges of the substituted amino group in Ar ^T1 are the same as examples and preferred ranges of the substituted amino group in the substituent which may be Ar ^T1 is have to be described later.

The substituent which Ar ^T1 may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen It is an atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group, an aryl group or a monovalent heterocyclic group And these groups may further have a substituent.

The aryl group in the substituent which Ar ^T1 may have is preferably a phenyl group, a naphthyl group, a fentenyl group, a dihydrophenthenyl group or a fluorenyl group, more preferably a phenyl group or a fluorenyl group, and further a phenyl group Preferably, these groups may have a substituent.
As a monovalent heterocyclic group in the substituent which Ar ^T1 may have, pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, azacarbazolyl group , Diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group is preferable, pyridyl group, pyrimidinyl group, triazinyl group, dibenzofuranyl group, dibenzothienyl group or carbazolyl group is more preferable, and dibenzofuranyl group, dibenzothienyl group or Carbazolyl groups are more preferable, and these groups may have a substituent.
In the substituted amino group in the substituent which Ar ^T1 may have, as a substituent which an amino group has, an aryl group or a monovalent heterocyclic group is preferable, an aryl group is more preferable, and these groups are further substituted It may have a group. The example and the preferable range of the aryl group in the substituent which an amino group has are the same as the example and the preferable range of the aryl group in the substituent which Ar ^T1 may have. The example and the preferable range of the monovalent | monohydric heterocyclic group in the substituent which an amino group has are the same as the example and the preferable range of the monovalent | monohydric heterocyclic group in the substituent which Ar ^T1 may have.

Preferred examples of the substituent which the substituent which Ar ^T1 may have may further have preferably include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent group. Are a heterocyclic group, a substituted amino group, a halogen atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group Or an aryl group, which may further have a substituent.

Ar ^T1 is an aryl group of the substituent which may further have the substituent which may have, examples and preferable range of the monovalent heterocyclic group and substituted amino group, respectively, Ar ^T1 is have The examples and the preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in the optional substituents are the same.

At least one of Ar ^T1 is preferably a monovalent donor-type heterocyclic group, and more preferably a group represented by Formula (T1-1), since the light emitting device of the present invention is more excellent in light emission efficiency. These groups may have a substituent.
Ar ^T1 is preferably a monovalent donor-type heterocyclic group, and more preferably a group represented by Formula (T1-1), because the external quantum efficiency of the light-emitting device of the present invention is further excellent. These groups may have a substituent.

An example and a preferred range of the substituent which may be possessed by the ring R ^T1 and the ring R ^T2 represented by the formula (T1-1) are an example of the substituent which may be possessed by Ar ^T1 and a preferable range It is the same as the range.

At least one of ring R ^T1 and ring R ^T2 is preferably an aromatic hydrocarbon ring which does not contain a group represented by —C (= O) — in the ring, and the ring is a substituent You may have.

The ring ^RT1 and the ring ^RT2 are each preferably a benzene ring, a naphthalene ring, a fluorene ring, a spirobifluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a carbazole ring, a dibenzofuran because the light emitting efficiency of the light emitting device of the present invention is more excellent. Ring, dibenzothiophene ring, phenoxazine ring, phenothiazine ring, 9,10-dihydroacridine ring or 5,10-dihydrophenazine ring, more preferably benzene ring, fluorene ring, spirobifluorene ring, carbazole ring, dibenzofuran It is a ring or a dibenzothiophene ring, more preferably a benzene ring, a fluorene ring or a carbazole ring, and these rings may have a substituent.

X ^T1 is a single bond, an oxygen atom, a sulfur atom or a group represented by —C (R ^XT1 ′) ₂ —, more preferably a single bond, an oxygen atom or a sulfur atom, still more preferably a single bond is there.

R ^XT1 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group These groups may have a substituent.

R ^XT1 ′ is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group or an aryl group, and still more preferably an alkyl group, The group may have a substituent.

It is preferred that a plurality of R ^XT1 'be bonded to each other so as not to form a ring with the carbon atom to which each is bonded.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^XT1 and R ^XT1 ′ are respectively an aryl group in a substituent which may be possessed by Ar ^T1 and a monovalent heterocyclic group And the same as the examples and preferred ranges of the substituted amino group.

The example and the preferred range of the substituent which R ^XT1 and R ^XT1 ′ may have are the same as the example and the preferred range of the substituent which the substituent which Ar ^T1 may have may further have. It is.

  The group represented by Formula (T1-1) is preferably a group represented by Formula (T1-1A) to Formula (T1-1D), because the light emission efficiency of the light emitting device of the present invention is more excellent. More preferably, they are groups represented by Formula (T1-1A) to Formula (T1-1C).

X ^T2 and X ^T3 are preferably a single bond, a group represented by -N (R ^XT2 )-, or a group represented by -C (R ^XT2 ') _2- .
At least one of X ^T2 and X ^T3 is preferably a single bond, and more preferably X ^T3 is a single bond.
When at least one of X ^T2 and X ^T3 is a single bond, the other is an oxygen atom, a sulfur atom, a group represented by -N (R ^XT2 )-, or -C (R ^XT2 ') _2- It is preferable that it is group represented by these, and it is more preferable that it is group represented by -N (R ^<XT2 )-, or group represented by -C (R ^<XT2 ') _2- .

Examples and preferred ranges of R ^XT2 are the same as the examples and preferred ranges of R ^XT1 .
Examples and preferred ranges of R ^XT2 'are the same as the examples and preferred ranges of R ^XT1 '.
Examples and preferred ranges of the substituent that R ^XT2 and R ^XT2 ′ may have are the same as the examples and the preferred range of the substituent that R ^XT1 and R ^XT1 ′ may have.

R ^{T1 to} R ^T12 are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, 1 Is more preferably a divalent heterocyclic group or a substituted amino group, still more preferably a hydrogen atom, an alkyl group, an aryl group or a monovalent heterocyclic group, and these groups further have a substituent It is also good.

Wherein ^{(T1-1A), R T1, R} T2, R T4, R T5, R T7 and R ^T8 are each particularly preferably a hydrogen atom.

Wherein (T1-1B) ~ formula (T1-1D), R ^T1 ~R ^T12 is particularly preferably a hydrogen atom.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^{T1 to} R ^T12 are respectively an aryl group in a substituent which may be possessed by Ar ^T1 , a monovalent heterocyclic group and Examples and preferred ranges of the substituted amino group are the same.
Examples and preferred ranges of the substituents which may be possessed by R ^{T1 to} R ^T12 are the same as the examples and preferred ranges of the substituent which the substituent which may be possessed by Ar ^T1 may further have. is there.

L ^T1 is preferably an arylene group or a divalent heterocyclic group, more preferably an arylene group, and these groups may have a substituent.

The arylene group represented by L ^T1 is preferably a group represented by Formula (A-1) to Formula (A-9), Formula (A-19) or Formula (A-20), and Preferably, it is a group represented by Formula (A-1) to Formula (A-3), Formula (A-8) or Formula (A-9), and more preferably, Formula (A-1) or (A It is a group represented by A-2), and these groups may have a substituent.
The divalent heterocyclic group represented by L ^T1 is preferably a group represented by the formula (AA-1) to the formula (AA-6), a formula (AA-10) to the formula (AA-15) or a formula (AA-). 18) to a group represented by the formula (AA-22), more preferably a group represented by the formula (AA-1) to the formula (AA-4) or the formula (AA-10) to the formula (AA-15) .

The example and the preferable range of a substituent which L ^T1 may have are the same as the examples and a preferable range of a substituent which Ar ^T1 may have.

R ^T1 ′ is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups may have a substituent.
The example and the preferred range of the aryl group and the monovalent heterocyclic group in R ^T1 ′ are the same as the examples and the preferred range of the aryl group and the monovalent heterocyclic group in the substituent which Ar ^T1 may have, respectively. It is.
The example and the preferable range of the substituent which ^RT1 'may have are the same as the example and the preferable range of the substituent which the substituent which Ar ^T1 may have may further have.

The carbon atom number of the aromatic hydrocarbon group in Ar ^T2 is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the carbon atom number of the substituent.
The aromatic hydrocarbon group in Ar ^T2 is preferably an electron-withdrawing group or an aromatic group containing a group represented by -C (= O)-in the ring because the light emitting efficiency of the light emitting device of the present invention is more excellent. Group hydrocarbon groups, and these groups may have a substituent.

  Examples of the aromatic hydrocarbon group containing a group represented by -C (= O)-in the ring include naphthoquinone ring, anthraquinone ring, phenanthtoquinone ring, indenone ring, fluorenone ring, tetralone ring, benzene in these rings A ring in which one or more and five or less rings are fused, or a group in which one or more hydrogen atoms directly bonded to carbon atoms constituting the ring are removed from the ring in which these rings are fused two or more and five or less Preferably a group in which one or more hydrogen atoms directly bonded to carbon atoms constituting the ring are removed from a naphthoquinone ring, an anthraquinone ring, a phenanthrene quinone ring, a fluorenone ring or a phenanthrenone ring, and these groups are substituted It may have a group.

Examples of the aromatic hydrocarbon group other than the aromatic hydrocarbon group containing a group represented by -C (= O)-in the ring in Ar ^T2 include a benzene ring, a naphthalene ring, an indene ring, a fluorene ring and a phenanthrene ring And a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from a dihydrophenanthrene ring or a ring formed by condensing 2 to 5 of these rings, and the light emitting device of the present invention Of the benzene ring, the fluorene ring, the spirobifluorene ring, the phenanthrene ring, or the dihydrophenanthrene ring by one or more hydrogen atoms directly bonded to carbon atoms constituting the ring. And more preferably a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting the ring from a benzene ring, and these rings have a substituent It can have.

  The aromatic hydrocarbon group containing an electron withdrawing group is preferably an aromatic hydrocarbon group having an electron withdrawing group as a substituent, and this group has a substituent other than the electron withdrawing group It may be

  As an electron withdrawing group, the alkyl group which has a fluorine atom as a substituent, a fluorine atom, a cyano group, a nitro group, an acyl group, and a carboxyl group are mentioned, for example, Preferably, it is a cyano group.

  The alkyl group having a fluorine atom as a substituent is preferably a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group or a perfluorooctyl group.

  In the aromatic hydrocarbon group containing an electron-withdrawing group, the number of electron-withdrawing groups possessed by the aromatic hydrocarbon group is usually 1 to 10, preferably 1 to 5, and more The number is preferably 1 to 3, and more preferably 1 or 2.

The carbon atom number of the heterocyclic group in Ar ^T2 is usually 2 to 60, preferably 2 to 30, and more preferably 3 to 15, not including the carbon atom number of the substituent.

The heterocyclic group in Ar ^T2 is preferably a monocyclic heterocyclic group containing two or more groups represented by = N- in the ring, or, because the light emitting efficiency of the light emitting device of the present invention is more excellent. A group represented by —C (= O) —, a group represented by —S (= O) —, a group represented by —S (= O) ₂ — and NN— in the ring A heterocyclic group of a fused ring containing at least one group selected from the group consisting of groups, more preferably a monocyclic heterocyclic group containing two or more groups represented by = N- in the ring These groups may have a substituent.

  The monocyclic heterocyclic group containing two or more groups represented by = N- in the ring is a triazole ring, an oxadiazole ring, a thiadiazole ring, a diazabenzene ring or a triazine ring, and the carbon atom constituting the ring is And groups in which one or more hydrogen atoms directly bonded are removed, preferably groups in which one or more hydrogen atoms directly bonded to carbon atoms constituting the ring are removed from a triazole ring, diazabenzene ring or triazine ring, More preferably, it is a group obtained by removing one or more hydrogen atoms directly bonded to carbon atoms constituting a ring from a pyrimidine ring or a triazine ring, and these groups may have a substituent.

A group represented by —C (= O) —, a group represented by —S (= O) —, a group represented by —S (= O) ₂ — and NN— in the ring As a heterocyclic group of a fused ring containing at least one group selected from the group consisting of groups, benzothiophene dioxide ring, benzothiophene oxide ring, benzopyranone ring, azanaphthalene ring, diazanaphthalene ring, triazanaphthalene ring, An azaindole ring, a diazaindole ring, a quinolinone ring, a benzodiazole ring, a benzotriazole ring, a benzooxadiazole ring, a benzothiadiazole ring, a ring in which one to five aromatic rings are fused to these rings, or It is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a ring formed by condensing these rings by 2 or more and 5 or less, preferably dibenzothiophene dioxide , Dibenzothiophene oxide ring, dibenzopyranone ring, azanaphthalene ring, diazanaphthalene ring, azaanthracene ring, diazaanthracene ring, azaphenanthrene ring, diazaphenanthrene ring, azacarbazole ring, diazacarbazole ring, or acridone It is a group excluding one or more hydrogen atoms directly bonded to atoms constituting the ring from the ring, more preferably a dibenzothiophene dioxide ring, a dibenzopyranone ring, an azanaphthalene ring, a diazanaphthalene ring, an azaanthracene It is a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a ring, diazaanthracene ring or diazaphenanthrene ring, more preferably an atom constituting a ring from a dibenzothiophene dioxide ring A group excluding one or more hydrogen atoms directly bonded to These groups may have a substituent.

A group represented by —C (= O) —, a group represented by —S (= O) —, a group represented by —S (= O) ₂ — and NN— in the ring The heterocyclic group of the fused ring containing at least one group selected from the group consisting of groups is preferably selected from a group represented by -S (= O) ₂ -and a group represented by = N- in the ring. A heterocyclic group of a fused ring containing at least one group selected from the group consisting of, more preferably a heterocyclic group of a fused ring containing a group represented by -S (= O) _2-; May have a substituent.
A group represented by —C (= O) —, a group represented by —S (= O) —, a group represented by —S (= O) ₂ — and NN— in the ring The heterocyclic group of the fused ring containing at least one group selected from the group consisting of groups, represented by -S (= O)-, a group represented by -C (= O)-contained in the ring The total number of groups represented by groups, -S (= O) _2- and groups represented by = N- is usually 1 to 10, preferably 1 to 5 and more preferably Is one to three, more preferably one.

In Ar ^T2 , a monocyclic heterocyclic group containing two or more groups represented by = N- in the ring, and a group represented by -C (= O)-in the ring, -S (= O A heterocyclic group other than a fused ring containing at least one group selected from the group consisting of a group represented by-), a group represented by -S (= O) ₂ -and a group represented by = N- The heterocyclic group is preferably a group obtained by removing one or more hydrogen atoms directly bonded to atoms constituting a ring from a pyridine ring, a diazole ring, a dibenzofuran ring or a dibenzothiophene ring, and these groups are substituents May be included.

Ar ^T2 is preferably a monocyclic heterocyclic group containing two or more groups represented by = N- in the ring, or -C (= in the ring, because Ar ^T2 is more excellent in the light emission efficiency of the light-emitting element of the present invention. It is selected from the group consisting of a group represented by O)-, a group represented by -S (= O)-, a group represented by -S (= O) ₂ -and a group represented by = N- A heterocyclic group of a fused ring containing at least one group, or an aromatic hydrocarbon group containing an electron-withdrawing group or a group represented by —C (= O) — in the ring, more preferably A monocyclic heterocyclic group containing two or more groups represented by = N- in the ring, or a group represented by -C (= O)-in the ring, -S (= O)- A heterocyclic group of a fused ring containing at least one group selected from the group consisting of a group represented by -S (= O) ₂ -and a group represented by = N-, more preferably , In the ring = - a monocyclic heterocyclic group containing group two or more represented by, and these groups may have a substituent.

As a substituent which may be possessed by Ar ^T2 (different from the group represented by the formula (1T ′) described later, and the same applies hereinafter), an alkyl group, a cycloalkyl group and an alkoxy group are preferable. And a monovalent heterocyclic group other than a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent donor type heterocyclic group or an electron withdrawing group, and more preferably an alkyl group, an aryl group or a monovalent group. It is a monovalent heterocyclic group other than a donor type heterocyclic group or an electron withdrawing group, more preferably an alkyl group or an aryl group, and these groups may have a substituent.

The example and the preferable range of the aryl group in the substituent which Ar ^T2 may have are the same as the example and the preferable range of the aryl group in the substituent which Ar ^T1 may have.

  The monovalent heterocyclic group other than the monovalent donor type heterocyclic group is preferably pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, dibenzofuranyl group, dibenzothienyl group, azacarbazolyl group, or It is a diazacarbazolyl group, and these groups may have a substituent.

The example and the preferable range of the substituent which the substituent which Ar ^T2 may have may further have are the substituents of the substituent which Ar ^T1 may have may further have. Same as example and preferred range.

  The compound represented by the formula (T-1) is preferably a compound represented by the formula (T′-1) to the formula (T′-16), because the light emitting efficiency of the light emitting device of the present invention is more excellent. More preferably, it is a compound represented by Formula (T'-1)-Formula (T'-5) or Formula (T'-10)-Formula (T'-12), More preferably, it is a formula It is a compound represented by (T'-1) or Formula (T'-3), Especially preferably, it is a compound represented by Formula (T'-3).

［式中、
Ｔ^X1は、酸素原子、硫黄原子又は−Ｎ（Ｒ^1T）−で表される基を表す。
Ｔ^X2は、＝Ｎ−で表される基又は＝Ｃ（Ｒ^1T）−で表される基を表す。
Ｔ^X3は、−Ｃ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）−で表される基又は−Ｓ（＝Ｏ）₂−で表される基を表す。
Ｔ^X4は、酸素原子、硫黄原子、−Ｎ（Ｒ^1T）−で表される基、−Ｃ（＝Ｏ）−で表される基、−Ｓ（＝Ｏ）−で表される基又は−Ｓ（＝Ｏ）₂−で表される基を表す。
Ｒ^1T及びＲ^1T'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、１価のドナー型複素環基以外の１価の複素環基、電子求引性基又は式（１T’）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。
複数存在するＲ^1Tは、同一でも異なっていてもよい。但し、複数存在するＲ^1Tのうち、少なくとも１個は式（１T’）で表される基である。
複数存在するＲ^1T'は、同一でも異なっていてもよい。但し、複数存在するＲ^1T'のうち、少なくとも１個は式（１T’）で表される基であり、且つ、少なくとも１個は電子求引性基である。］

[In the formula,
T ^X1 represents an oxygen atom, a sulfur atom or a group represented by —N (R ^1T ) —.
T ^X2 represents a group represented by = N- or a group represented by = C (R ^1T )-.
T ^X3 represents a group represented by -C (= O)-, a group represented by -S (= O)-or a group represented by -S (= O) _2- .
T ^X4 is an oxygen atom, a sulfur atom, a group represented by -N (R ^1T )-, a group represented by -C (= O)-, a group represented by -S (= O)-or- Represents a group represented by S ((O) ₂ —.
R ^1T and R ^1T ′ each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent complex other than a monovalent donor heterocyclic group A ring group, an electron withdrawing group or a group represented by the formula (1T ′) is represented, and these groups may have a substituent.
Plural R ^1Ts may be the same or different. However, among the R ^1T presence of a plurality of, at least one is a group represented by the formula (1T ').
Plural R ^1T 's may be the same or different. However, among the plurality of R ^1T 's, at least one is a group represented by formula (1T'), and at least one is an electron-withdrawing group. ]

T ^X1 is preferably a group represented by -N (R ^1T )-.
T ^X3 is preferably a group represented by -C (= O)-or a group represented by -S (= O) _2- , more preferably -S (= O) _2- Group.
T ^{X 4} is preferably an oxygen atom, a sulfur atom, a group represented by -N (R ^1T )-, a group represented by -C (= O)-or a group represented by -S (= O) _2- And more preferably an oxygen atom, a sulfur atom or a group represented by -N (R ^1T )-, still more preferably an oxygen atom.

Among the plurality of R ^1T 's, n ^T2 is preferably a group represented by formula (1T').
Among the plurality of R ^1T 's, n ^T2 is preferably a group represented by formula (1T').

Among the plurality of R ^1T ', 1 to 5 are preferably electron withdrawing groups, 1 to 3 are more preferably electron withdrawing groups, and 1 or 2 are preferably electron withdrawing groups. It is more preferable that it is an attractive group.

［式中、Ｌ^T1、ｎ^T1及びＡｒ^T1は、前記と同じ意味を表す。］

[Wherein, L ^T1 , n ^T1 and Ar ^T1 represent the same meaning as described above. ]

R ^1T is preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group other than a monovalent donor-type heterocyclic group, an electron-withdrawing group or a group represented by formula (1T ′) And more preferably a hydrogen atom, an alkyl group, an aryl group or a group represented by the formula (1T ′), and still more preferably a hydrogen atom, an aryl group or a group represented by the formula (1T ′) These groups may have a substituent.

R ^1T ′ is preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group other than a monovalent donor-type heterocyclic group, an electron-withdrawing group or a group represented by the formula (1T ′) And more preferably a hydrogen atom, an alkyl group, an aryl group, an electron withdrawing group or a group represented by the formula (1T ′), and still more preferably a hydrogen atom, an electron withdrawing group or a formula It is a group represented by 1T '), and these groups may have a substituent.

The example and the preferable range of the substituent which R ^1T and R ^1T ′ may have are the same as the example and the preferable range of the substituent which the substituent which Ar ^T1 may have may further have. It is.

  The compound (T) preferably satisfies the requirement (i) and the requirement (ii) because the light emission efficiency of the light emitting device of the present invention is more excellent.

As a compound (T), the compound represented by a following formula is mentioned, for example. In the formula, Z ¹ represents a group represented by -N = or a group represented by -CH =. Z ² represents an oxygen atom or a sulfur atom. Z ³ is, -C (= O) - represents a group represented by - a group represented by or a -S (= O) _2. When a plurality of Z ¹ , Z ² and Z ³ exist, they may be the same or different.

Z ¹ is preferably a group represented by -N =. Z ² is preferably an oxygen atom. Z ³ is preferably a group represented by —S (= O) ₂ —.

  Compound (T) is available from Aldrich, Luminescence Technology Corp. For example, WO2007 / 063754, WO2008 / 056746, WO2011 / 032686, WO2012 / 096263, JP2009-227663A, and the like. It may be synthesized according to the method described in JP-A-2010-275255, Advanced Materials (Adv. Mater), vol. 26, pp. 7931-7958, 2014.

[First composition]
The first organic layer comprises a compound (T), a phosphorescent transition metal complex having a dendron, a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material and an antioxidant. It may be a layer containing a composition containing at least one selected from the group (hereinafter also referred to as "first composition"). However, in the first composition, the hole transport material, the hole injection material, the electron transport material, the electron injection material and the light emitting material are different from the compound (T). In the first composition, the light emitting material is different from the phosphorescent transition metal complex having dendron.

[Hole transport material]
Hole transport materials are classified into low molecular weight compounds and high molecular weight compounds, and are preferably high molecular weight compounds. The hole transport material may have a crosslinking group.

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

In the first composition, the compounding amount of the hole transporting material is usually 1 to 400 parts by mass, assuming that the total of the compound (T) and the phosphorescent transition metal complex having dendron is 100 parts by mass. And preferably 5 to 150 parts by mass.
The hole transport material may be used alone or in combination of two or more.

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

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

  As a high molecular compound, polyphenylene, polyfluorene, and these derivatives are mentioned, for example. The polymer compound may be doped with metal.

In the first composition, the compounding amount of the electron transporting material is usually 1 to 400 parts by mass, assuming that the total of the compound (T) and the phosphorescent transition metal complex having dendron is 100 parts by mass, Preferably, it is 5 to 150 parts by mass.
The electron transporting material may be used alone or in combination of two or more.

[Hole Injection Material and Electron Injection Material]
The hole injecting material and the electron injecting material are classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injecting material and the electron injecting material may have a crosslinking group.

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

  As the polymer compound, for example, polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive materials such as polymers containing an aromatic amine structure in the main chain or side chain Polymers are included.

In the first composition, the compounding amount of the hole injecting material and the electron injecting material is usually 1 when the total of the compound (T) and the phosphorescent transition metal complex having dendron is 100 parts by mass. It is -400 parts by mass, preferably 5 to 150 parts by mass.
Each of the electron injecting material and the hole injecting material may be used alone or in combination of two or more.

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

The type of ion to be doped is an anion if it is a hole injecting material, and a cation if it is an electron injecting material. Examples of the anion include polystyrene sulfonate ion, alkyl benzene sulfonate ion and camphor sulfonate ion. Examples of the cation include lithium ion, sodium ion, potassium ion and tetrabutyl ammonium ion.
The ions to be doped may be used singly or in combination of two or more.

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

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

  Examples of the polymer compound include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a fluorenediyl group, a phenanthrenediyl group, a dihydrophenanthrendiyl group, a group represented by the formula (X) described later, a carbazole diyl group, and a phenoxyl group. The high molecular compound containing a sadindiyl group, phenothiazine diyl group, pyrene diyl group etc. is mentioned.

  In the first composition, the compounding amount of the light emitting material is usually 0.1 to 400 parts by mass, preferably 100 parts by mass, with the total of the compound (T) and the phosphorescent transition metal complex having dendron being preferable. Is 5 to 150 parts by mass.

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

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the compound (T) and the phosphorescent transition metal complex having dendron and does not inhibit light emission and charge transport, and examples thereof include phenolic antioxidants and phosphorus And antioxidants.

In the first composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass, based on 100 parts by mass of the total of the compound (T) and the phosphorescent transition metal complex having dendron.
The antioxidant may be used alone or in combination of two or more.

[First ink]
A composition containing the compound (T), a phosphorescent transition metal complex having a dendron, and a solvent (hereinafter, also referred to as “first ink”) can be spin-coated, casting, or microgravure-coated Gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, ink jet printing method, capillary coating method, nozzle coating method Etc. can be suitably used.

  The viscosity of the first ink may be adjusted according to the type of application method, but when a solution such as inkjet printing method is applied to a printing method via an ejection device, clogging and flight bending occur during ejection. As 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 that can dissolve or uniformly disperse the solid content in the ink. As the solvent, for example, chlorinated solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, etc .; ether solvents such as tetrahydrofuran, dioxane, anisole, 4-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellsolve acetate, methyl benzoate and phenyl acetate System solvents; ethylene glycol, Polyhydric alcohol solvents such as serine and 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N, N-dimethylformamide and the like And amide solvents of the following. The solvents may be used alone or in combination of two or more.

  In the first ink, the compounding amount of the solvent is usually 1000 to 100000 parts by mass, preferably 2000, when the total of the compound (T) and the phosphorescent transition metal complex having dendron is 100 parts by mass. -20000 parts by mass.

<Second organic layer>
The second organic layer is a layer containing a crosslinked body of a polymer compound containing a structural unit having a crosslinking group (hereinafter also referred to as “polymer compound of second organic layer”).

  The crosslinked product of the polymer compound of the second organic layer can be obtained by bringing the polymer compound of the second organic layer into a crosslinked state by the method, conditions, and the like described above.

[Polymer Compound of Second Organic Layer]
The polymer compound of the second organic layer is preferably a polymer compound containing a structural unit having at least one type of crosslinking group selected from the group of crosslinking groups A, because the light emitting device of the present invention is excellent in light emission efficiency .

  As the crosslinking group selected from the crosslinking group A group, since the light emission efficiency of the light emitting device of the present invention is more excellent, it is preferable that Formula (XL-1) to Formula (XL-4), and Formula (XL-7) to Formula (XL-10) or a crosslinking group represented by Formula (XL-16) to Formula (XL-19), and more preferably, Formula (XL-1), Formula (XL-3), or Formula (XL-) 9) a crosslinking group represented by the formula (XL-10), the formula (XL-16) or the formula (XL-17) to the formula (XL-19), more preferably a formula (XL-1), A crosslinking group represented by the formula (XL-16) or the formula (XL-17) to the formula (XL-19), particularly preferably a group represented by the formula (XL-1) or the formula (XL-17) It is a crosslinking group.

  The structural unit having at least one crosslinking group selected from the crosslinking group A, which is contained in the polymer compound of the second organic layer, is represented by the structural unit represented by the formula (2) or the formula (2 ′) The structural unit is preferably a structural unit represented by the following formula.

The structural unit nA represented by the formula (2) is preferably an integer of 0 to 3 and more preferably an integer of 0 to 2 because the light emission efficiency of the light emitting device of the present invention is more excellent.
n is preferably 2, because the light emission efficiency of the light emitting device of the present invention is more excellent.

Ar ³ is preferably an aromatic hydrocarbon group which may have a substituent, because the light emission efficiency of the light emitting device of the present invention is more excellent.
The carbon atom number 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 carbon atom number of the substituent. is there.
The arylene group moiety excluding the n substituents of the aromatic hydrocarbon group represented by Ar ³ is preferably a group represented by Formula (A-1) to Formula (A-20), More preferably, a group represented by Formula (A-1), Formula (A-2), Formula (A-6) to Formula (A-10), Formula (A-19) or Formula (A-20) And more preferably a group represented by Formula (A-1), Formula (A-2), Formula (A-7), Formula (A-9) or Formula (A-19), Groups may have a substituent.

The carbon atom number 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 carbon atom number 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 Formula (AA-1) to Formula (AA-34) is there.

The aromatic hydrocarbon group and the heterocyclic group represented by Ar ³ may have a substituent, and as the substituent, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group can be mentioned Preferred is a group, a halogen atom, a monovalent heterocyclic group and a cyano group.

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

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

Arylene group represented by L ^A may have a substituent. The arylene group is preferably a phenylene group or a fluorenediyl group, more preferably an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group or a fluorene-9,9-diyl group. Examples of the substituent which the arylene group may have include 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 A crosslinking group selected from the group is preferable, and these groups may further have a substituent.

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

L ^A is preferably an arylene group or an alkylene group, and more preferably a phenylene group, a fluorenicyl group or an alkylene group, since L ^A facilitates the production of the polymer compound of the second organic layer. Groups may have a substituent.

  As the crosslinking group represented by X, since the light emission efficiency of the light emitting device of the present invention is more excellent, Formula (XL-1) to Formula (XL-4), Formula (XL-7) to Formula (XL-10) Or a crosslinking group represented by Formula (XL-16) to Formula (XL-19), and more preferably, Formula (XL-1), Formula (XL-3), Formula (XL-9), Formula (XL) XL-10) a crosslinking group represented by the formula (XL-16) or the formula (XL-17) to the formula (XL-19), more preferably a formula (XL-1), a formula (XL-16) Or a crosslinking group represented by Formula (XL-17) to Formula (XL-19), and particularly preferably a crosslinking group represented by Formula (XL-1) or Formula (XL-17).

  The constituent unit represented by the formula (2) may be contained singly or in combination of two or more in the polymer compound of the second organic layer.

-The structural unit represented by the formula (2 ') is preferably an integer of 0 to 3, more preferably an integer of 0 to 2 because the light emission efficiency of the light emitting device of the present invention is more excellent. It is preferably 0 or 1, and particularly preferably 0.

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

  c is preferably 0 because the production of the polymer compound of the second organic layer is facilitated and the light emission efficiency of the light emitting device of the present invention is more excellent.

Ar ⁵ is preferably an aromatic hydrocarbon group which may have a substituent, because the light emission efficiency of the light emitting device of the present invention is more excellent.

The definition and examples of the arylene group moiety of the aromatic hydrocarbon group represented by Ar ⁵ excluding the m substituents are the same as the definitions and examples of the arylene group represented by Ar ^{X 2} in formula (X) .

The definition and examples of the divalent heterocyclic group moiety excluding the m substituents of the heterocyclic group represented by Ar ⁵ are the same as those of the divalent heterocyclic group moiety represented by Ar ^X2 in formula (X) Same as definition and example.

The definition and examples of divalent groups other than m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ⁵ and at least one hetero ring are directly bonded are represented by the formula (X) The definitions and examples 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 to each other are the same as the definition and the example.

Ar ⁴ and Ar ⁶ each are preferably an arylene group which may have a substituent, because the light emission efficiency of the light emitting device of the present invention is more excellent.

The definition and the example of the arylene group represented by Ar ⁴ and Ar ⁶ are the same as the definition and the example of the arylene group represented by Ar ^X1 and Ar ^X3 in the formula (X).

The definitions and examples of the divalent heterocyclic group represented by Ar ⁴ and Ar ⁶ are the same as the definitions and the examples of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 in Formula (X).

The group represented by Ar ⁴ , Ar ⁵ and Ar ⁶ may have a substituent, and as the substituent, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, A halogen atom, a monovalent heterocyclic group and a cyano group are preferred.

The definitions and examples of the alkylene group, cycloalkylene group, arylene group and divalent heterocyclic group represented by K ^A are respectively the alkylene group, cycloalkylene group, arylene group and divalent hetero group represented by L ^A The same as the definition and examples of the ring group.

K ^A is preferably a phenylene group or a methylene group because this facilitates the production of the polymer compound of the second organic layer.

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

  The constituent unit represented by the formula (2 ′) may be contained singly or in combination of two or more types in the polymer compound of the second organic layer.

-Preferred embodiment of the structural unit represented by the formula (2) or (2 ') The structural unit represented by the formula (2) is represented by, for example, the formula (2-1) to the formula (2-30) Structural units represented by formula (2 ′) include, for example, structural units represented by formulas (2′-1) to (2′-9).

-Other structural unit The polymer compound of the second organic layer preferably has a structural unit represented by Formula (X) since it has excellent hole transportability. Further, since the polymer compound of the second organic layer is more excellent in the light emission efficiency of the light emitting element of the present invention, it is preferable to further include a structural unit represented by the formula (Y).

  The polymer compound of the second organic layer is excellent in the hole transportability and further excellent in the light emission efficiency of the light emitting device of the present invention, and therefore the structural unit represented by the formula (X) and the formula (Y) It is preferable that the structural unit represented by these is included.

［式中、
ａ^X1及びａ^X2は、それぞれ独立に、０以上の整数を表す。
Ａｒ^X1及びＡｒ^X3は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^X2及びＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2及びＡｒ^X4が複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^X1〜Ｒ^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。］

[In the formula,
Each of a ^X1 and a ^X2 independently represents an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^X2 and Ar ^X4 are each independently an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded These groups may have a substituent. When a plurality of Ar ^X2 and Ar ^X4 exist, they may be the same or different.
Each of R ^{X1 to} R ^X3 independently 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. When a plurality of R ^X2 and R ^X3 exist, they may be the same or different. ]

^Each of a ^X1 and a ^X2 is preferably an integer of 2 or less, more preferably 0 or 1, because the light emission efficiency of the light emitting device of the present invention is more excellent.

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

The arylene group represented by Ar ^X1 and Ar ^X3 is more preferably a group represented by Formula (A-1) or Formula (A-9), and still more preferably represented by Formula (A-1) It is a group.
The divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 is more preferably represented by Formula (AA-1), Formula (AA-2) or Formula (AA-7) to Formula (AA-26) And more preferably a group represented by formula (AA-10) to formula (AA-15) or formula (AA-18) to formula (AA-22), particularly preferably a group represented by formula (AA-). 10) A group represented by formula (AA-11) or formula (AA-18) to formula (AA-22).
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 represented by Formula (A-1), Formula (A-6), Formula (A-7), Formula (A-9) to Formula (A-11) Or a group represented by formula (A-19), and these groups may have a substituent.
The more preferable range of the divalent heterocyclic group represented by Ar ^X2 and Ar ^X4 is the same as the more preferable range of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 .

More preferable range of 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 And the more preferable ranges are the same as the more preferable ranges and the further preferable ranges of the arylene group and the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 respectively.
Examples of the divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^X4 and at least one bivalent heterocyclic group are directly bonded to each other include, for example, groups represented by the following formulas: These may have a substituent.

［式中、Ｒ^XXは、水素原子、アルキル基、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。］

[Wherein, 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 substituent which the group represented by Ar ^{X1 to} Ar ^X4 and R ^{X1 to} R ^X3 may have is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups further have a substituent It may be done.

  The structural unit represented by the formula (X) is preferably a structural unit represented by the formula (X-1) to the formula (X-7).

［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ともに環を形成していてもよい。］

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

  The structural unit represented by the formula (X) is preferably 0.1 to 90% by mole based on the total amount of the structural units contained in the polymer compound of the second organic layer because the hole transportability is excellent. More preferably, it is 1-70 mol%, More preferably, it is 10-50 mol%.

  As a structural unit represented by Formula (X), the structural unit represented by Formula (X1-1)-Formula (X1-19) is mentioned, for example.

  In the polymer compound of the second organic layer, the structural unit represented by the formula (X) may be contained alone or in combination of two or more.

［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。］

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

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

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

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

^Examples of the divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded to each other include at least one represented by Ar ^X2 and Ar ^X4 in the formula (X) The same groups as the divalent group in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded to each other can be mentioned.

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

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-1) to (Y-7), and from the viewpoint of the light emission efficiency of the light emitting device of the present invention And preferably a structural unit represented by Formula (Y-1) or Formula (Y-2), and from the viewpoint of the electron transportability of the polymer compound of the second organic layer, preferably Or a structural unit represented by the formula (Y-4), and from the viewpoint of the hole transportability of the polymer compound of the second organic layer, preferably a group represented by the formula (Y-5) to the formula (Y-7) It is a structural unit represented by).

［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ともに環を形成していてもよい。］

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

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

  The constitutional unit represented by the formula (Y-1) is preferably a constitutional unit represented by the formula (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。］

[Wherein, R ^Y11 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. Plural R ^Y11 may be the same or different. ]

R ^Y11 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ともに環を形成していてもよい。］

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

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

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

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

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

［式中、Ｒ^Y2は前記と同じ意味を表す。］

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

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

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

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

［式中、
Ｒ^Y1は前記と同じ意味を表す。
Ｒ^Y3は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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 ^Y1 represents the same meaning as described above.
R ^Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

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

［式中、
Ｒ^Y1は前記を同じ意味を表す。
Ｒ^Y4は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は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 ^Y1 has the same meaning as described above.
R ^Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

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

  Examples of the constitutional unit represented by the formula (Y) include constitutional units represented by the formula (Y-11) to the formula (Y-56).

The structural unit represented by the formula (Y), wherein Ar ^Y1 is an arylene group, is included in the polymer compound of the second organic layer because the light emitting device of the present invention is more excellent in the light emission efficiency. Preferably it is 0.5-80 mol% with respect to the total amount of structural units, More preferably, it is 30-60 mol%.

A constituent unit represented by the formula (Y), wherein Ar ^{Y 1} is a divalent heterocyclic group, or a bivalent in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. The structural unit which is a group of the above is preferably 0.5 to the total amount of structural units contained in the polymer compound of the second organic layer, because the charge transportability of the polymer compound of the second organic layer is excellent. It is 40 mol%, more preferably 3 to 30 mol%.
The structural unit represented by the formula (Y) may be contained singly or in combination of two or more in the polymer compound of the second organic layer.

  Examples of the polymer compound of the second organic layer include polymer compounds P-1 to P-8 shown in Table 1. Here, the “other structural unit” means a structural unit other than the structural units represented by Formula (2), Formula (2 ′), Formula (X), and Formula (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 ′ each represent a molar ratio of each constituent unit. p ′ + q ′ + r ′ + s ′ + t ′ = 100 and 70 ≦ p ′ + q ′ + r ′ + s ′ ≦ 100. ]

  The polymer compound of the second organic layer may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, and may be other embodiments, but plural It is preferable that it is a copolymer which copolymerized the raw material monomer of seed | species.

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 > -1 * 10 < ⁵ >.

[Method for producing polymer compound of second organic layer]
The polymer compound of the second organic layer can be produced using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, p. 897-1091 (2009), etc. Examples thereof include a method of polymerization by a coupling reaction using a transition metal catalyst such as a reaction, Yamamoto reaction, Buchwald reaction, Stille reaction, Negishi reaction and Kumada reaction.

  In the above-mentioned polymerization method, as a method of charging the monomers, a method of charging the whole amount of the monomers at once into the reaction system, charging a part of the monomers and reacting them, then batching the remaining monomers, A method of charging continuously or in parts, a method of charging monomers continuously or in parts, etc. may be mentioned.

  Examples of transition metal catalysts include palladium catalysts and nickel catalysts.

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

[(Y ₁ × 1000) / X ₁ value]
The value of (Y ₁ × 1000) / X ₁ in the polymer compound of the second organic layer can be determined, for example, by the following method.
First, for each constitutional unit of the polymer compound, a value x obtained by multiplying the molar ratio C of the constitutional unit to the total mole of all constitutional units and the molecular weight M of the constitutional unit, and the molar ratio C and the constitutional unit A value y is obtained by multiplying the number n of the crosslinking groups possessed. Next, the sum of x obtained for each structural unit is X ₁ , and the sum of y obtained for each structural unit is Y ₁ .
The value of (Y ₁ × 1000) / X ₁ is approximately equal to the average number of crosslinking groups per 1000 molecular weight of the polymer compound of the second organic layer, and the crosslinking group in the polymer compound of the second organic layer It can be effectively used as an index indicating the average number of

A specific method of calculating the average number of crosslinking groups is described based on the polymer compound HTL-8 used in Example D11. The macromolecular compound HTL-8 has a structural unit derived from the compound M7, the compound M8 and the compound M5. The molar ratio of each constituent unit to the total moles of all constituent units is 0.45 for the constituent unit derived from compound M7, 0.05 for the constituent unit derived from compound M8, and the constituent unit derived from compound M5 It is 0.50. The molecular weight of the structural unit derived from compound M7 is 776.45, the molecular weight of the structural unit derived from compound M8 is 240.20, and the molecular weight of the structural unit derived from compound M5 is 750.51. The number of crosslinking groups in the structural unit derived from compound M7 is 2, the number of crosslinking groups in the structural unit derived from compound M8 is 2, the number of crosslinking groups in the structural unit derived from compound M5 is 0 It is. From these numerical values, X ₁ , Y ₁ and (Y ₁ × 1000) / X ₁ can be obtained as follows.
X ₁ = (0.45 × 776.45) + (0.05 × 240.20) + (0.50 × 750.51) = 736.67
Y ₁ = (0.45 × 2) + (0.05 × 2) + (0.50 × 0) = 1.00
(Y ₁ × 1000) / X ₁ = (1.00 × 1000) /736.67=1.36

The value of (Y ₁ × 1000) / X ₁ is usually 0.25 or more and 10.0 or less, and is preferably 0.28 or more and 5.0 or less because the light emission efficiency of the light emitting device of the present invention is more excellent. More preferably, it is 0.30 or more and 3.0 or less, more preferably 0.30 or more and 2.0 or less, and particularly preferably 0.30 or more and 1.0 or less.

The value of (Y ₁ × 1000) / X ₁ is calculated to be 0.201 for the polymer compound (P0) described in Patent Document 1 using the above method.

[Second composition]
The second organic layer is selected from the group consisting of a crosslinked product of the polymer compound of the second organic layer, a hole transporting material, a hole injecting material, an electron transporting material, an electron injecting material, a light emitting material and an antioxidant. It may be a layer containing a composition containing at least one material (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 And the same as the examples and preferred ranges of the electron transport material, the hole injection material, the electron injection material and the light emitting material. In the second composition, the compounding amounts of the hole transporting material, the electron transporting material, the hole injecting material, the electron injecting material and the light emitting material are each 100 parts by mass of the crosslinked product of the polymer compound of the second organic layer When it is set, it is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

  The example and the preferable range of the antioxidant contained in a 2nd composition are the same as the example and a preferable range of the antioxidant contained in a 1st composition. In the second composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass, based on 100 parts by mass of the crosslinked product of the polymer compound of the second organic layer.

A composition containing the polymer compound of the second organic layer and a solvent (hereinafter also referred to as “second ink”) is suitably used in the wet method described in the section of the first ink. Can. The preferred range of the viscosity of the second ink is the same as the preferred range of the viscosity of the first ink. Examples and preferred ranges of the solvent contained in the second ink are the same as examples and preferred ranges of the solvent contained in the first ink.
In the second ink, the compounding amount of the solvent is usually 1000 to 100000 parts by mass, preferably 2000 to 20 000 parts by mass, based on 100 parts by mass of the polymer compound of the second organic layer.

<Layer configuration 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. The first organic layer is usually a light emitting layer (hereinafter, referred to as "first light emitting layer"). The second organic layer is usually a hole transporting layer, a second light emitting layer or an electron transporting layer, preferably a hole transporting layer or a second light emitting layer, more preferably a hole transporting layer .

The first organic layer and the second organic layer are preferably adjacent to each other because the light emission efficiency of the light emitting device of the present invention is more excellent.
The second organic layer is preferably a layer provided between the anode and the first organic layer, because the light emission efficiency of the light emitting device of the present invention is more excellent, and the second organic layer is preferably between the anode and the first organic layer. The hole transporting layer or the second light emitting layer provided is more preferable, and the hole transporting layer provided between the anode and the first organic layer is still more preferable.

  In the first organic layer, the compound (T) and the phosphorescent transition metal complex having dendron may be contained singly or in combination of two or more. In the second organic layer, the crosslinked body of the crosslinked material may be contained singly or in combination of two or more.

  When the second organic layer is a hole transport layer provided between the anode and the first organic layer, the light emission efficiency of the light emitting device of the present invention is more excellent, and therefore, between the anode and the second organic layer It is preferable to further include a hole injection layer. When the second organic layer is a hole transport layer provided between the anode and the first organic layer, the light emission efficiency of the light emitting device of the present invention is more excellent, and therefore, between the cathode and the first organic layer Preferably, at least one of the electron injection layer and the electron transport layer is further included.

  When the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the light emitting efficiency of the light emitting device of the present invention is more excellent. It is preferable to further include at least one layer of a hole injection layer and a hole transport layer in between. When the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the light emitting efficiency of the light emitting element of the present invention is more excellent. It is preferable to further include at least one of the electron injection layer and the electron transport layer in between.

  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. It is preferable to further include at least one layer of a hole injection layer and a hole transport layer in between. When the second organic layer is the second light emitting layer provided between the cathode and the first organic layer, the light emitting efficiency of the light emitting element of the present invention is more excellent. It is preferable to further include at least one of the electron injection layer and the electron transport layer in between.

  When the second organic layer is an electron transporting layer provided between the cathode and the first organic layer, the light emitting device of the present invention is more excellent in the light emission efficiency, so that it is between the anode and the first organic layer. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer. When the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the light emitting device of the present invention is more excellent in the light emission efficiency, so that it is between the cathode and the second organic layer. It is preferable to further have an electron injection layer.

  Examples of the layer configuration of the light emitting device of the present invention include the layer configurations represented by (D1) to (D15). The light emitting device of the present invention generally has a substrate, but may be laminated from the anode on the substrate or may be laminated from the cathode on the substrate.

(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 First 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 / positive Injection layer / hole transport layer (second organic layer) / first light emission 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 / 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 (D1) to (D15), "/" means that layers before and after that are stacked adjacent to each other. Specifically, “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” refers to the second light emitting layer (second organic layer) and the first light emitting layer It means that the light emitting layer (first organic layer) is stacked adjacent to one another.

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 may each be provided in two or more layers, as necessary.
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.

  The thicknesses 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 are usually 1 nm to 1 μm, preferably 2 nm to It is 500 nm, more preferably 5 nm to 150 nm.

  In the light emitting element of the present invention, the order, the number, and the thickness of the layers to be stacked may be adjusted in consideration of the light emission efficiency, the driving voltage and the element life of the light emitting element.

[Second light emitting layer]
The second light emitting layer is usually a second organic layer or a layer containing a light emitting material, preferably 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 which may be contained in the above-mentioned second composition. Be The light emitting materials contained in the second light emitting layer may be contained singly or in combination of two or more.
When the light emitting device of the present invention has the second light emitting layer, and the hole transport layer described later and the electron transport layer described later are not the second organic layer, the second light emitting layer is the second organic layer Is preferred.

[Hole transport layer]
The hole transport layer is usually a second organic layer or a layer containing a hole transport material, preferably a second organic layer. When the hole transport layer is a layer containing a hole transport material, examples of the hole transport material include a hole transport material which may be contained in the first composition described above. The hole transport material contained in the hole transport layer may be contained singly or in combination of two or more.
When the light emitting device of the present invention has a hole transporting layer and the above-mentioned second light emitting layer and the electron transporting layer described later are not the second organic layer, the hole transporting layer is the second organic layer. Is preferred.

[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 which may be contained in the above-mentioned first composition. . The electron transporting material contained in the electron transporting layer may be contained singly or in combination of two or more.
When the light emitting device of the present invention has an electron transporting layer, and the above-mentioned second light emitting layer and the above hole transporting layer are not the second organic layer, the electron transporting layer is the second organic layer Is preferred.

[Hole Injection Layer and Electron Injection Layer]
The hole injection layer is a layer containing a hole injection material. As a hole injection material contained in a hole injection layer, the hole injection material which the above-mentioned 1st composition may contain is mentioned, for example. The hole injection material contained in the hole injection layer may be contained singly or in combination of two or more.
The electron injection layer is a layer containing an electron injection material. As an electron injection material contained in an electron injection layer, the electron injection material which the above-mentioned 1st composition may contain is mentioned, for example. The electron injecting material contained in the electron injecting layer may be contained singly or in combination of two or more.

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

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

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

In the light emitting device of the present invention, at least one of the anode and the cathode is usually transparent or translucent, but preferably the anode is transparent or translucent.
Examples of the method of forming the anode and the cathode include a vacuum evaporation method, a sputtering method, an ion plating method, a plating method and a laminating method.

[Method of manufacturing light emitting device]
As a method of forming each layer such as the first light emitting layer, the second light emitting layer, the hole transporting layer, the electron transporting layer, the hole injecting layer and the electron injecting layer, when using a low molecular weight compound, for example, A vacuum vapor deposition method, a method by film formation from a solution or molten state may be mentioned, and when using a polymer compound, for example, a method by film formation from a solution or molten state may be mentioned.
The first light emitting layer, the second light emitting layer, the hole transporting layer, the electron transporting layer, the hole injecting layer and the electron injecting layer include the first ink, the second ink, and the light emitting material described above, the holes It can be formed by an application method such as a spin coating method or an inkjet printing method using an ink containing each of a transport material, an electron transport material, a hole injection material and an electron injection material.

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

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

  In Examples, the polystyrene equivalent number average molecular weight (Mn) of the polymer compound and the polystyrene equivalent weight average molecular weight (Mw) were determined by size exclusion chromatography (SEC) using tetrahydrofuran as a mobile phase. The SEC measurement conditions are as follows.

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

The calculation of the value of ΔE _ST of the compound was structural optimization of the ground state of the compound by the density functional theory of B3LYP level. At that time, 6-31 G * was used as a basis function. Then, using the obtained structure-optimized structure, ΔE _ST of the compound was calculated by the time-dependent density functional method of B3LYP level. In addition, it calculated using Gaussian 09 as a quantum chemistry calculation program.

Synthesis Example M Synthesis of Compounds M1 to M25 Compound M1 was synthesized according to the method described in JP-A-2010-189630.
Compound M2 was synthesized according to the method described in JP-A-2008-106241.
Compound M3 was synthesized according to the method described in JP-A-2010-215886.
Compounds M4, M9 and M10 were synthesized according to the method described in WO2002 / 045184.
Compound M5 was synthesized according to the method described in WO 2005/049546.
Compound M6 was synthesized according to the method described in WO 2011/049241.
Compound M7 was synthesized according to the method described in WO 2015/145871.
Compounds M8 and M18 were synthesized according to the method described in WO 2013/146806.
Compounds M11, M13, M15, M16, M19 and M24 were synthesized according to the method described in WO 2016/031639.
Compounds M12 and M14 were synthesized according to the method described in JP-A-2011-174062.
Compound M17 was synthesized according to the method described in JP-A-2014-1328.
Compound M20 was synthesized according to the method described in WO 2017/146083.
Compound M21 was synthesized according to the method described in JP-A-2010-215886.
Compounds M22 and M23 were synthesized according to the method described in WO 2013/191088.
Compound M25 was synthesized according to the method described in WO 2017/146083.

<Synthesis Example HTL-1> Synthesis of Polymer Compound HTL-1 After the inside of the reaction vessel is changed to an inert gas atmosphere, Compound M1 (0.995 g), Compound M2 (0.106 g), Compound M3 (0.0924 g) Compound M4 (0.736 g), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) and toluene (50 ml) were added and heated to 105 ° C. A 20% by mass aqueous tetraethylammonium hydroxide solution (6.6 ml) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 5.5 hours. After that, phenylboronic acid (24.4 mg), 20% by mass aqueous tetraethylammonium hydroxide solution (6.6 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) were added thereto, and the reaction was continued for 14 hours. It was allowed to reflux. Thereafter, an aqueous solution of sodium diethyldithiacarbamate was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting reaction solution was cooled and then washed twice with water, twice with a 3% by mass aqueous acetic acid solution, and twice with water, and the obtained solution was added dropwise to methanol, whereby a precipitate was generated. The obtained precipitate was dissolved in toluene, and purified by passing through an alumina column and a silica gel column in this order. The resulting solution was added dropwise to methanol and stirred, whereupon a precipitate formed.
The obtained precipitate was collected by filtration and dried to obtain 0.91 g of a polymer compound HTL-1. The Mn of the polymer compound HTL-1 was 5.2 × 10 ⁴ , and the Mw was 2.5 × 10 ⁵ .

The polymer compound HTL-1 has a structural unit derived from the compound M1, a structural unit derived from the compound M4, a structural unit derived from the compound M2, and a compound in the theoretical value determined from the amount of the starting materials It is a copolymer in which the constituent unit derived from M3 is constituted at a molar ratio of 50: 40: 5: 5.
The value (average number of crosslinking groups) of (Y ₁ × 1000) / X ₁ of the polymer compound HTL-1 was 0.73.

<Synthesis Example HTL-2> Synthesis of Polymer Compounds HTL-2 to HTL-17 and HTL-C1 to HTL-C3 Polymer Compounds (Copolymer) HTL-2 to HTL-17 and HTL-C1 to HTL-C3 Were synthesized using the compounds of the types and molar ratios described in Table 2 by the synthesis method described in the same table. The values of Mn, Mw and (Y ₁ × 1000) / X ₁ (the average number of crosslinking groups) of the obtained polymer compound are as described in Table 2.

Synthetic Examples G and R Synthesis of Metal Complexes G1 to G6 and R1 to R4 The metal complex G1 was synthesized according to the method described in JP-A-2013-237789.
The metal complex G2 was synthesized according to the method described in WO 2009/131255.
The metal complex G3 was synthesized according to the method described in WO 2011/032626.
The metal complex G4 was synthesized according to the method described in JP-A-2014-224101.
Metal complexes G5 and G6 were synthesized according to the method described in JP-A-2014-224101.
Metal complex R1 was synthesize | combined according to the method of Unexamined-Japanese-Patent No. 2006-188673.
The metal complex R2 was synthesized according to the method described in JP-A-2008-179617.
Metal complex R3 was synthesize | combined according to the method of Unexamined-Japanese-Patent No. 2011-105701.
The metal complex R4 was synthesized according to the method described in WO 2003/040256.

Synthesis Example H Synthesis and Acquisition of Compounds H1 to H8 and HC1 to HC3 Compound H1 was synthesized according to the method described in WO 2010/136109.
Compound H2 was synthesized according to the method described in WO 2014/115743.
Compound H3 was synthesized according to the method described in WO2006 / 114966.
Compound H4 was synthesized according to the method described in WO 2011/070963.
Compound H5 was synthesized according to the method described in WO 2008/056746.
Compounds H6, H8, HC1 and HC3 were purchased from Luminescense Technology.
Compound H7 was synthesized according to the method described in JP-A-2010-254676.
Compound HC2 was synthesized according to the method described in JP-A-2010-189630.

Example D1 Production and Evaluation of Light-Emitting Element D1 (Formation of Anode and Hole Injection Layer)
An anode was formed by depositing an ITO film with a thickness of 45 nm on a glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a hole injection agent of polythiophene sulfonic acid type, is formed into a film with a thickness of 35 nm by spin coating on the anode, and 170 ° C. on a hot plate under air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of second organic layer)
The polymer compound HTL-2 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film is formed to a thickness of 20 nm by spin coating on the hole injection layer, and the film is heated at 180 ° C. for 60 minutes on a hot plate under a nitrogen gas atmosphere. Organic layer (hole transport layer) was formed. By this heating, the polymer compound HTL-2 became a crosslinked body.

(Formation of the first organic layer)
Compound H1 and metal complex G2 (compound H1 / metal complex G2 = 70% by mass / 30% by mass) were dissolved in toluene at a concentration of 2% by mass. Using the obtained toluene solution, a film is formed on the second organic layer to a thickness of 80 nm by spin coating, and the first organic layer is heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. A (light emitting layer) was formed.

(Formation of cathode)
After reducing the pressure of the substrate on which the first organic layer is formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride is formed on the first organic layer to a thickness of about 4 nm as a cathode, and then About 80 nm of aluminum was deposited on the sodium fluoride layer. After vapor deposition, sealing was performed using a glass substrate, to fabricate a light emitting device D1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting device D1. The luminous efficiency [lm / W] and CIE chromaticity coordinates were measured at a current density of 0.25 mA / cm ² . The results are shown in Table 3.

<Examples D2 to D12, Comparative Examples CD1 to CD2> Preparation and Evaluation of Light-Emitting Elements D2 to D12 and CD1 to CD2 Instead of “polymer compound HTL-2” in (Formation of the second organic layer) of Example D1 Light emitting elements D2 to D12 and CD1 to CD2 were produced in the same manner as in Example D1 except that the materials listed in Table 3 were used. EL light emission was observed by applying a voltage to the light emitting elements D2 to D12 and CD1 to CD2. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 3.

Comparative Example CD3 Preparation and Evaluation of Light-Emitting Element CD3 “Compound H1 and Metal Complex G2 (Compound H1 / Metal Complex G2 = 70 mass% / 30 Mass%)” (Formation of the First Organic Layer) of Example D1 A light emitting device CD3 was produced in the same manner as in Example D1 except that the materials listed in Table 3 were used instead of. By applying a voltage to the light emitting element CD3, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 3.

Examples D13 to D16, D19, D20, and D22 and Comparative Example CD4 Preparation and Evaluation of Light-Emitting Elements D13 to D16, D19, D20, D22, and CD4 "High in (formation of second organic layer) of Example D1 The compound H1 and the metal complex G2 (compound H1 / metal) were used in place of “Molecular compound HTL-2” and the materials described in Table 4 were used and “the formation of the first organic layer” in Example D1 was “toluene The complex G2 = 70% by mass / 30% by mass) was dissolved at a concentration of 2% by mass. ”“ The material described in Table 4 was dissolved in chlorobenzene at a concentration of 2% by mass. ” Light-emitting elements D13 to D16, D19, D20, D22, and CD4 were produced in the same manner as in Example D1 except for the above. EL light emission was observed by applying a voltage to the light emitting elements D13 to D16, D19, D20, D22 and CD4. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 4.

Example D17 Preparation and Evaluation of Light-Emitting Element D17 Using “Polymer Compound HTL-1” in place of “Polymer Compound HTL-2” in (Formation of the Second Organic Layer) of Example D1 and Further Dissolve “compound H1 and metal complex G2 (compound H1 / metal complex G2 = 70 mass% / 30 mass%) in toluene at (formation of first organic layer) of Example D1 at a concentration of 2 mass% Except that “the compound H2 and the metal complex G2 (compound H2 / metal complex G2 = 70% by mass / 30% by mass) are dissolved in toluene at a concentration of 3% by mass” instead of “.” A light emitting device D17 was produced in the same manner as in Example D1. By applying a voltage to the light emitting device D17, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 4.

Example D18, D21, D23 and Comparative Example CD5 Preparation and Evaluation of Light-Emitting Elements D18, D21, D23, and CD5 "Polymer Compound HTL-2" in (Formation of Second Organic Layer) of Example D1 and Then, instead of “compound H1 and metal complex G2 (compound H1 / metal complex G2 = 70 mass% / 30 mass%)” in (Formation of the first organic layer) of Example D1, the materials described in Table 4 are used Light-emitting elements D18, D21, D23 and CD5 were produced in the same manner as in Example D1 except for using them. EL light emission was observed by applying a voltage to the light emitting elements D18, D21, D23 and CD5. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 4.

Examples D24 to D28 and Comparative Example CD6 Preparation and Evaluation of Light-Emitting Elements D24 to D28 and CD6 Instead of “polymer compound HTL-2” in (Formation of the second organic layer) of Example D1, Table 5 Light-emitting elements D24 to D28 and CD6 were produced in the same manner as in Example D1, except that the materials described in were used. EL light emission was observed by applying a voltage to the light emitting elements D24 to D28 and CD6. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.075 mA / cm ² are shown in Table 5.

Examples D29 to D31 Preparation and Evaluation of Light-Emitting Elements D29 to D31 “Polymer Compound HTL-1” in place of “Polymer Compound HTL-2” in (Formation of the Second Organic Layer) of Example D1 Further, in place of “the compound H1 and the metal complex G2 (compound H1 / metal complex G2 = 70 mass% / 30 mass%)” in (Formation of the first organic layer) of Example D1, Light-emitting elements D29 to D31 were produced in the same manner as in Example D1, except that the described materials were used. By applying a voltage to the light emitting elements D29 to D31, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 15 mA / cm ² are shown in Table 6.

Examples D32 and D33 Preparation and Evaluation of Light-Emitting Elements D32 and D33 “Polymer Compound HTL-1” in place of “Polymer Compound HTL-2” in (Formation of the Second Organic Layer) of Example D1 Further, 2 mass% of “compound H1 and metal complex G2 (compound H1 / metal complex G2 = 70 mass% / 30 mass%) in“ Toluene in Example D1 (formation of first organic layer) A light emitting device D32 and a light emitting device D32 were prepared in the same manner as in Example D1 except that “the material described in Table 6 was dissolved in chlorobenzene at a concentration of 2% by mass” instead of being dissolved at a concentration. D33 was produced. By applying a voltage to the light emitting elements D32 and D33, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 15 mA / cm ² are shown in Table 6.

Example D34 Preparation and Evaluation of Light-Emitting Element D34 (Formation of Anode and Hole Injection Layer)
An anode was formed by depositing an ITO film with a thickness of 45 nm on a glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a hole injection agent of polythiophene sulfonic acid type, is formed into a film with a thickness of 65 nm by spin coating on the anode, and 170 ° C. on a hot plate under an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of second organic layer)
The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the obtained xylene solution, a film is formed to a thickness of 20 nm by spin coating on the hole injection layer, and the film is heated at 180 ° C. for 60 minutes on a hot plate under a nitrogen gas atmosphere. Organic layer (hole transport layer) was formed. By this heating, the polymer compound HTL-1 became a crosslinked body.

(Formation of the first organic layer)
Compound H1 and metal complex R1 (compound H1 / metal complex R1 = 90% by mass / 10% by mass) were dissolved in xylene at a concentration of 3% by mass. Using the obtained xylene solution, a film is formed on the second organic layer to a thickness of 80 nm by spin coating, and the first organic layer is heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. A (light emitting layer) was formed.

(Formation of cathode)
After reducing the pressure of the substrate on which the first organic layer is formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride is formed on the first organic layer to a thickness of about 4 nm as a cathode, and then About 80 nm of aluminum was deposited on the sodium fluoride layer. After vapor deposition, sealing was performed using a glass substrate to fabricate a light emitting device D34.

(Evaluation of light emitting element)
By applying a voltage to the light emitting element D34, EL light emission was observed. The luminous efficiency [lm / W] and CIE chromaticity coordinates were measured at a current density of 0.25 mA / cm ² . The results are shown in Table 7.

Example D35 Preparation and Evaluation of Light-Emitting Element D35 Except using “polymer compound HTL-8” in place of “polymer compound HTL-1” in (Formation of the second organic layer) of Example D34. In the same manner as in Example D34, a light emitting device D35 was produced. By applying a voltage to the light emitting device D35, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 7.

Examples D36 and D37 Preparation and Evaluation of Light-Emitting Devices D36 and D37 “Compound H1 and metal complex R1 (compound H1 / metal complex R1 = 90 mass% / 10 in (Formation of first organic layer) of Example D34 Light emitting devices D36 and D37 were produced in the same manner as in Example D34 except that the material described in Table 7 was used instead of “mass%)”. By applying a voltage to the light emitting elements D36 and D37, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 7.

<Comparative Examples CD7 and CD8> Preparation and evaluation of light emitting elements CD7 and CD8 Using the materials described in Table 7 instead of “polymer compound HTL-1” in (Formation of the second organic layer) of Example D34. Further, “the compound H1 and the metal complex R1 (the compound H1 / the metal complex R1 = 90% by mass / 10% by mass) in (the formation of the first organic layer) of Example D34 in a concentration of 3% by mass Light emitting elements CD7 and CD8 were prepared in the same manner as in Example D34 except that “the material listed in Table 7 was dissolved in toluene at a concentration of 2% by mass” instead of being dissolved. Made. By applying a voltage to the light emitting elements CD7 and CD8, EL light emission was observed. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 7.

Comparative Example CD9 Preparation and Evaluation of Light-Emitting Element CD9 In “The formation of the second organic layer”, “The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass.” In Example D34. Instead of this, “the polymer compound HTL-2 was dissolved in chlorobenzene at a concentration of 0.6 mass%”, and “the xylene in Example D34 (formation of the first organic layer) was compound H1. And the metal complex R1 (compound H1 / metal complex R1 = 90% by mass / 10% by mass) was dissolved at a concentration of 3% by mass, “2% by mass of the material described in Table 7 in toluene A light emitting device CD9 was produced in the same manner as in Example D34, except that it was dissolved at a concentration of EL light emission was observed by applying a voltage to the light emitting element CD9. The measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of 0.25 mA / cm ² are shown in Table 7.

Example D38 Preparation and Evaluation of Light-Emitting Element D38 Compound H1 and Metal Complex R1 (Compound H1 / Metal Complex R1 = 90% by Mass / 10 Mass in “Formation of First Organic Layer) of Example D34 %) Was dissolved at a concentration of 3% by mass. The same as Example D 34 except that “the material described in Table 8 was dissolved at a concentration of 2% by mass in toluene”. The light emitting device D38 was manufactured. EL light emission was observed by applying a voltage to the light emitting element D38. Table 8 shows the measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of ² mA / cm ² .

Examples D39 to D42 Preparation and Evaluation of Light-Emitting Elements D39 to D42 “Compound H1 and Metal Complex R1 (Compound H1 / Metal Complex R1 = 90% by Mass / 10 in (Formation of First Organic Layer) of Example D34) Light emitting elements D39 to D42 were produced in the same manner as in Example D34 except that the material described in Table 8 was used instead of “mass%)”. By applying a voltage to the light emitting elements D39 to D42, EL light emission was observed. Table 8 shows the measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of ² mA / cm ² .

Comparative Examples CD10 and CD11 Preparation and Evaluation of Light-Emitting Elements CD10 and CD11 Compound H1 and Metal Complex R1 (Compound H1 / Metal Complex R1 = 90 Mass in “Formation of First Organic Layer) of Example D34 % / 10% by mass) was dissolved at a concentration of 3% by mass "except that" the material described in Table 8 was dissolved in chlorobenzene at a concentration of 2% by mass ". Light emitting elements CD10 and CD11 were produced in the same manner as Example D34. By applying a voltage to the light emitting elements CD10 and CD11, EL light emission was observed. Table 8 shows the measurement results of luminous efficiency [lm / W] and CIE chromaticity coordinates at a current density of ² mA / cm ² .

Claims (16)

A light emitting device comprising 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 low-molecular compound containing no transition metal satisfying at least one of the requirements (i) and (ii), and a phosphorescent transition metal complex having dendron,
The second organic layer is a layer containing a crosslinked product of a polymer compound containing a structural unit having a crosslinking group,
When the total molecular weight of all the structural units that constitute the polymer compound and X _1, the total number of crosslinking groups all the structural units having constituting the polymer compound was a _{Y 1, (Y 1 × 1000} ) The light emitting element, wherein the value of / X ₁ is 0.25 or more.
(I) The absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is less than 0.25 eV.
(Ii) It is represented by Formula (T-1).

[In the formula,
n ^T1 represents an integer of 0 or more and 5 or less. When there are a plurality of n ^{T1 's} , they may be the same or different.
n ^T2 represents an integer of 1 or more and 10 or less.
Ar ^T1 represents a substituted amino group or a monovalent heterocyclic group, the monovalent heterocyclic group containing a nitrogen atom having no double bond in the ring, and = N in the ring a group represented by, -C (= O) - group represented by, -S (= O) - group represented by _{and,, -S (= O) 2} - does not include a group represented by 1 It is a divalent heterocyclic group, and these groups may have a substituent. When a plurality of Ar ^T1 are present, they may be the same or different.
L ^T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -NR ^T1 '-, an oxygen atom or a sulfur atom, and these groups have a substituent May be R ^T1 ′ 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. When a plurality of L ^T1 are present, they may be the same or different.
Ar ^T2 represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
However, when all of Ar ^T1 is a substituted amino group or a group represented by formula (T1-1A), Ar ^T2 is a single ring containing two or more groups represented by = N- in the ring Heterocyclic group, a group represented by —C (= O) — in the ring, a group represented by —S (= O) —, a group represented by —S (= O) ₂ — and NN A heterocyclic group of a fused ring containing at least one selected from the group consisting of-, or an electron withdrawing group or an aroma containing a group represented by -C (= O)-within the ring Group hydrocarbon groups, and these groups may have a substituent. ]

[In the formula,
X ^T1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by -N (R ^XT1 )-, or a group represented by -C (R ^XT1 ') _2- . R ^XT1 and R ^XT1 ′ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or A cyano group is represented, and these groups may have a substituent. The plurality of R ^XT1 's may be the same or different, and may be combined with each other to form a ring together with the atoms to which they are attached.
R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 , R ^T7 and R ^T8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may have a substituent. ] The light emitting device according to claim 1, wherein the crosslinking group is a crosslinking group selected from a crosslinking group A group.
(Crosslinking group A group)

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5]. When two or more R ^XL exist, they may be the same or different. When there are a plurality of n ^XL , they may be the same or different. * 1 represents a bonding position. These crosslinking groups may have a substituent, and when there are a plurality of such substituents, they may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ] The light emitting element according to claim 2, wherein the structural unit having a crosslinking group is a structural unit represented by Formula (2) or a structural unit represented by Formula (2 ′).

[In the formula,
nA represents an integer of 0 to 5, and n represents 1 or 2. When a plurality of nA are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent It is also good. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. If L ^A is plurally present, they may be the same or different.
X represents a crosslinking group selected from the aforementioned crosslinking group A group. When two or more X exist, they may be same or different. ]

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When there are a plurality of 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 heterocyclic ring are directly bonded, and these groups have a substituent It 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 being directly bonded or bonded via an oxygen atom or a sulfur atom to a group other than the group bonded to the nitrogen atom to which the group is bonded It may be done.
K ^A 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 each have a substituent It is also good. R 'represents the same meaning as described above. If K ^A there are a plurality, they may be the same or different.
X 'represents a bridging group selected from the above bridging group A, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent . When a plurality of X 'are present, they may be the same or different. However, at least one X ′ is a crosslinking group selected from the aforementioned crosslinking group A group. ] The light emitting element according to any one of claims 1 to 3, wherein the phosphorescent transition metal complex having dendron is a metal complex represented by the formula (1).

[In the formula,
M represents a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ¹ represents an integer of 1 or more, and n ² represents an integer of 0 or more. However, when M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹ + n ² is 3, and when M is a palladium atom or a platinum atom, n ¹ + n ² is 2.
E ¹ and E ² each independently represent a carbon atom or a nitrogen atom. However, at least one of E ¹ and E ² is a carbon atom. When a plurality of E ¹ and E ² exist, they may be the same or different.
The ring L ¹ represents a heteroaromatic ring, and the ring may have a substituent. When there are a plurality of such substituents, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings L ¹ exist, they may be the same or different.
The ring L ² represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When there are a plurality of such substituents, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of rings L ² exist, they may be the same or different.
The substituent which ring L ¹ may have and the substituent which ring L ² may have may be bonded to each other to form a ring together with the atoms to which they are attached.
At least one of ring L ¹ and ring L ² has a dendron.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. Each of A ¹ and A ² independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand with A ¹ and A ² . When ^two or more A ¹ -G ¹ -A ² are present, they may be the same or different. ] The light emitting device according to claim 4, wherein the metal complex represented by the formula (1) is a metal complex represented by the formula (1-A).

[In the formula,
M, n ¹ , n ² , E ¹ and A ¹ -G ¹ -A ² have the same meaning as described above.
The ring L ^1A represents a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, a triazole ring or a diazole ring, and these rings may have a substituent. When there are a plurality of such substituents, they may be bonded to each other to form a ring together with the atoms to which they are bonded. When two or more rings L ^1A are present, they may be the same or different.
E ^21A , E ^22A , E ^23A and E ^24A each independently represent a nitrogen atom or a carbon atom. When there are a plurality of E ^21A , E ^22A , E ^23A and E ^24A , they may be the same or different. When E ^21A is a nitrogen atom, R ^21A is absent. When E ^22A is a nitrogen atom, R ^22A is absent. When E ^23A is a nitrogen atom, R ^23A is absent. When E ^24A is a nitrogen atom, R ^24A is absent.
R ^21A , R ^22A , R ^23A and R ^24A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino A group or a halogen atom is represented, and these groups may have a substituent. When there are a plurality of R ^21A , R ^22A , R ^23A and R ^24A , they may be the same or different. R ^21A and R ^22A , R ^22A and R ^23A , R ^23A and R ^24A , and a substituent which may be possessed by the ring L ^1A and R ^21A respectively combine to form a ring together with the atoms to which they are attached You may form.
However, ring L ^1A has a dendron, or at least one of R ^21A , R ^22A , R ^23A and R ^24A is a dendron.
Ring L ^2A represents a benzene ring, a pyridine ring or a diazabenzene ring. ] The metal complex represented by the formula (1-A) is represented by the formula (1-B1), the formula (1-B2), the formula (1-B3), the formula (1-B4) or the formula (1-B5) The light emitting device according to claim 5, which is a metal complex represented.

[In the formula,
M, n ¹ , n ² , R ^21A , R ^22A , R ^23A , R ^24A and A ¹ -G ¹ -A ² have the same meanings as described above.
n ¹¹ and n ¹² each independently represent 1 or 2; However, when M is a ruthenium atom, a rhodium atom or an iridium atom, n ¹¹ + n ¹² is 3, and when M is a palladium atom or a platinum atom, n ¹¹ + n ¹² is 2.
R ^11B , R ^12B , R ^13B , R ^14B , R ^15B , R ^16B , R ^17B and R ^18B each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or an aryl group It represents an oxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^11B , R ^12B , R ^13B , R ^14B , R ^15B , R ^16B , R ^17B and R ^18B , they may be the same or different.
However, at least one of R ^11B , R ^12B , R ^13B , R ^14B , R ^15B , R ^16B , R ^17B , R ^18B , R ^21A , R ^22A , R ^23A and R ^24A is a dendron.
In the formula (1-B1), R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , and R ^11B and R ^21A respectively bond to form a ring with the atoms to which each is bonded. It may be In the formula (1-B2), ^R13B and ^R14B , ^R13B and ^R15B , ^R15B and ^R16B , ^R16B and ^R17B , ^R17B and ^R18B , and ^R18B and ^R21A respectively bind And may form a ring together with the atoms to which they are attached. Wherein (1-B3), R ^11B and R ^12B, R ^12B and R ^13B, R ^11B and R ^21A, R ^13B and R ^14B, R ^13B and R ^15B, R ^15B and R ^16B, R ^16B and R ^17B, R ^17B and R ^18B and R ^18B and R ^21A may be combined to form a ring together with the atoms to which they are attached. In the formula (1-B4), R ^11B and R ^18B , R ^14B and R ^15B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , and R ^11B and R ^21A are respectively bonded And may form a ring together with the atoms to which they are attached. In the formula (1-B5), R ^11B and R ^12B , R ^12B and R ^18B , R ^15B and R ^16B , R ^16B and R ^17B , R ^17B and R ^18B , and R ^11B and R ^21A are respectively bonded And may form a ring together with the atoms to which they are attached. ] The light emitting element according to any one of claims 1 to 6, wherein the dendron is a group represented by formula (D-A) or formula (D-B).

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

[In the formula,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more.
G ^DA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. A plurality of G ^DAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. The plurality of ^TDAs may be the same or different. ] The group represented by the formula (D-A) is a group represented by formula (D-A1), formula (D-A2), formula (D-A3), formula (D-A4) or formula (D-A5). The light emitting device according to claim 7, which is a

[In the formula,
R ^p1 , R ^p2 , R ^p3 and R ^p4 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p1 , R ^p2 and R ^p4 , they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. The plurality of np1 may be the same or different. ] The group represented by Formula (D-B) is a group represented by Formula (D-B1), Formula (D-B2), Formula (D-B3), Formula (D-B4), Formula (D-B5) or Formula The light emitting element according to claim 7, which is a group represented by (D-B6).

[In the formula,
R ^p1 , R ^p2 , R ^p3 and R ^p4 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p1 , R ^p2 and R ^p4 , they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, np3 represents 0 or 1, and np4 represents an integer of 0 to 4. Plural np1 may be the same or different. The plurality of np2 may be the same or different. ] The light emitting element according to any one of claims 1 to 9, wherein at least one of the Ar ^T1 is a group represented by a formula (T1-1).

[Wherein, X ^T1 represents the same meaning as described above.
Ring ^RT1 and ring ^RT2 are each independently an aromatic hydrocarbon ring which does not contain a group represented by -C (= O)-in the ring, or a group represented by = N- in the ring And a group represented by -C (= O)-, a group represented by -S (= O)-, and a heterocycle not containing a group represented by -S (= O) _2- , These rings may have a substituent. ] The group represented by Formula (T1-1) is a group represented by Formula (T1-1A), Formula (T1-1B), Formula (T1-1C), or Formula (T1-1D). 11. A light emitting device according to item 10.

[In the formula,
X ^T1 represents the same meaning as described above.
X ^T2 and X ^T3 each independently represent a single bond, an oxygen atom, a sulfur atom, a group represented by -N (R ^XT2 )-, or a group represented by -C (R ^XT2 ') _2- Represent. R ^XT2 and R ^XT2 ′ each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or A cyano group is represented, and these groups may have a substituent. Plural R ^XT2 's may be the same or different, and may combine with each other to form a ring together with the atoms to which they are attached.
R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 , R ^T7 , R ^T8 , R ^T9 , R ^T10 , R ^T11 and R ^T12 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group And an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may have a substituent. ] The Ar ^T2 is a monocyclic or heterocyclic group which may have a substituent and which contains two or more groups represented by = N- in the ring. The light emitting element as described in.   The light emitting element according to any one of claims 1 to 12, wherein the low molecular weight compound containing no transition metal satisfies the requirement (i) and the requirement (ii).   The first organic layer further contains at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. The light emitting element as described in any one of 13.   The light emitting element according to any one of claims 1 to 14, 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 15, wherein the second organic layer is a layer provided between the anode and the first organic layer.