JP2018083941A - Composition and light emitting element prepared therewith - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a light emitting element with high emission efficiency.SOLUTION: A composition contains a metal complex represented by formula (1), and a metal complex, such as an Ir complex, with phenylpyridine as a ligand [where, M is a Rh, Pd, Ir or Pt atom. n1 is an integer of 1 or greater, n2 is an integer of 0 or greater, n1+n2 is 2 or 3. E1 is a C or N atom. Ring B is an aromatic hydrocarbon ring or aromatic heterocycle. Z1A is a group represented by =N-, and the like. R1 is a C2-30 alkyl group. Ar1A is a cyclic substituent. A1-G1-A2 are anionic bidentate ligands].SELECTED DRAWING: None

Description

  The present invention relates to a composition and a light emitting device using the composition.

  Light-emitting elements such as organic electroluminescence elements can be suitably used for display and lighting applications, and research and development are being conducted. For example, Patent Document 1 describes a light-emitting element having a light-emitting layer containing a composition containing a metal complex (B) and a metal complex (R) represented by the following formula.

JP 2011-253980 A

  However, the light emitting element described above does not necessarily have sufficient light emission efficiency.

  Accordingly, an object of the present invention is to provide a light emitting element having excellent light emission efficiency. Another object of the present invention is to provide a composition useful for producing a light-emitting device having excellent luminous efficiency.

［式中、
Ｍは、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。
ｎ^１は１以上の整数を表し、ｎ^２は０以上の整数を表し、ｎ^１＋ｎ^２は２又は３である。
Ｍがロジウム原子又はイリジウム原子の場合、ｎ^１＋ｎ^２は３であり、Ｍがパラジウム原子又は白金原子の場合、ｎ^１＋ｎ^２は２である。
Ｅ^１は、炭素原子又は窒素原子を表す。Ｅ^１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Ｂ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、それらは互いに結合して、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Ｂ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。
Ｚ^１Ａは、＝Ｎ−で表される基又は＝Ｃ（Ｒ^Ｚ１Ａ）−で表される基を表す。Ｚ^１Ａが複数存在する場合、それらは同一であっても異なっていてもよい。Ｒ^Ｚ１Ａは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
Ｒ^１は、炭素原子数２以上３０以下のアルキル基を表し、これらの基は置換基を有していてもよい。Ｒ^１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^１Ａは、式（Ａｒ−１Ａ）で表される基を表す。Ａｒ^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。
Ａ^１−Ｇ^１−Ａ^２は、アニオン性の２座配位子を表す。Ａ^１及びＡ^２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。Ｇ^１は、単結合、又は、Ａ^１及びＡ^２とともに２座配位子を構成する原子団を表す。Ａ^１−Ｇ^１−Ａ^２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。］

［式中、
環Ａ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、それらは互いに結合して、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。
Ｒ^２及びＲ^３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、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。］

［式中、
Ｍ^２は、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。
ｎ^３は１以上の整数を表し、ｎ^４は０以上の整数を表し、ｎ^３＋ｎ^４は２又は３である。
Ｍ^２がロジウム原子又はイリジウム原子の場合、ｎ^３＋ｎ^４は３であり、Ｍ^２がパラジウム原子又は白金原子の場合、ｎ^３＋ｎ^４は２である。
Ｅ^４は、炭素原子又は窒素原子を表す。Ｅ^４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Ｌ^１は、６員の芳香族複素環を表し、こ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、それらは互いに結合して、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Ｌ^１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Ｌ^２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、それらは互いに結合して、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Ｌ^２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Ｌ^１が有していてもよい置換基と環Ｌ^２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Ｌ^１及び環Ｌ^２からなる群から選ばれる少なくとも１つの環は、置換基として式（１−Ｔ）で表される基を有する。式（１−Ｔ）で表される基が複数存在する場合、それらは同一でも異なっていてもよい。
Ａ^３−Ｇ^２−Ａ^４は、アニオン性の２座配位子を表す。Ａ^３及びＡ^４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。Ｇ^２は、単結合、又は、Ａ^３及びＡ^４とともに２座配位子を構成する原子団を表す。Ａ^３−Ｇ^２−Ａ^４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。］

［式中、Ｒ^１Ｔ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、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。］
［２］前記式（１）で表される金属錯体が、式（１−１）で表される金属錯体である、［１］に記載の組成物。

［式中、
Ｍ、Ｚ^１Ａ、ｎ^１、ｎ^２、Ｒ^１、Ａｒ^１Ａ及びＡ^１−Ｇ^１−Ａ^２は、前記と同じ意味を表す。
環Ｂ^１は、ベンゼン環、ピリジン環又はジアザベンゼン環を表し、Ｅ^１Ｂ、Ｅ^２Ｂ、Ｅ^３Ｂ及びＥ^４Ｂは、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ^１Ｂ、Ｅ^２Ｂ、Ｅ^３Ｂ及びＥ^４Ｂ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^１Ｂが窒素原子の場合、Ｒ^１Ｂは存在しない。Ｅ^２Ｂが窒素原子の場合、Ｒ^２Ｂは存在しない。Ｅ^３Ｂが窒素原子の場合、Ｒ^３Ｂは存在しない。Ｅ^４Ｂが窒素原子の場合、Ｒ^４Ｂは存在しない。
Ｒ^１Ｂ、Ｒ^２Ｂ、Ｒ^３Ｂ及びＲ^４Ｂ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^１Ｂ、Ｒ^２Ｂ、Ｒ^３Ｂ及びＲ^４Ｂ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^１ＢとＲ^２Ｂ、Ｒ^２ＢとＲ^３Ｂ、及び、Ｒ^３ＢとＲ^４Ｂ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。］
［３］前記式（１−１）で表される金属錯体が、式（１−２）で表される金属錯体である、［２］に記載の組成物。

［式中、Ｍ、Ｚ^１Ａ、ｎ^１、ｎ^２、Ｒ^１、Ａｒ^１Ａ、Ａ^１−Ｇ^１−Ａ^２、Ｒ^１Ｂ、Ｒ^２Ｂ、Ｒ^３Ｂ及びＲ^４Ｂは、前記と同じ意味を表す。］
［４］前記式（Ａｒ−１Ａ）で表される基が、式（Ａｒ−２Ａ）で表される基である、［１］〜［３］のいずれかに記載の組成物。

［式中、Ｒ^２及びＲ^３は、前記と同じ意味を表す。
環Ａ^１は、ベンゼン環、ピリジン環又はジアザベンゼン環を表し、Ｅ^１Ａ、Ｅ^２Ａ及びＥ^３Ａは、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ^１Ａが窒素原子の場合、Ｒ^１Ａは存在しない。Ｅ^２Ａが窒素原子の場合、Ｒ^２Ａは存在しない。Ｅ^３Ａが窒素原子の場合、Ｒ^３Ａは存在しない。
Ｒ^１Ａ、Ｒ^２Ａ及びＲ^３Ａ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^１ＡとＲ^２Ａ、及び、Ｒ^２ＡとＲ^３Ａ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。］
［５］前記式（Ａｒ−２Ａ）で表される基が、式（Ａｒ−３Ａ）で表される基である、［４］に記載の組成物。

［式中、Ｒ^２、Ｒ^３、Ｒ^１Ａ、Ｒ^２Ａ及びＲ^３Ａは、前記と同じ意味を表す。］
［６］前記式（２）で表される金属錯体が、式（２−Ｂ）で表される金属錯体である、［１］〜［５］のいずれかに記載の組成物。

［式中、
Ｍ^２、ｎ^３、ｎ^４及びＡ^３−Ｇ^２−Ａ^４は、前記と同じ意味を表す。
環Ｌ^１Ｂは、ピリジン環又はピリミジン環を表し、環Ｌ^２Ｂは、ベンゼン環、ピリジン環又はジアザベンゼン環を表し、Ｅ^１１Ｂ、Ｅ^１２Ｂ、Ｅ^１３Ｂ、Ｅ^１４Ｂ、Ｅ^２１Ｂ、Ｅ^２２Ｂ、Ｅ^２３Ｂ及びＥ^２４Ｂは、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ^１１Ｂ、Ｅ^１２Ｂ、Ｅ^１３Ｂ、Ｅ^１４Ｂ、Ｅ^２１Ｂ、Ｅ^２２Ｂ、Ｅ^２３Ｂ及びＥ^２４Ｂ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^１１Ｂが窒素原子の場合、Ｒ^１１Ｂは存在しない。Ｅ^１２Ｂが窒素原子の場合、Ｒ^１２Ｂは存在しない。Ｅ^１３Ｂが窒素原子の場合、Ｒ^１３Ｂは存在しない。Ｅ^１４Ｂが窒素原子の場合、Ｒ^１４Ｂは存在しない。Ｅ^２１Ｂが窒素原子の場合、Ｒ^２１Ｂは存在しない。Ｅ^２２Ｂが窒素原子の場合、Ｒ^２２Ｂは存在しない。Ｅ^２３Ｂが窒素原子の場合、Ｒ^２３Ｂは存在しない。Ｅ^２４Ｂが窒素原子の場合、Ｒ^２４Ｂは存在しない。
Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂは、それぞれ独立に、水素原子又は式（１−Ｔ）で表される基を表す。Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂ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^１１ＢとＲ^１２Ｂ、Ｒ^１２ＢとＲ^１３Ｂ、Ｒ^１３ＢとＲ^１４Ｂ、Ｒ^１１ＢとＲ^２１Ｂ、Ｒ^２１ＢとＲ^２２Ｂ、Ｒ^２２ＢとＲ^２３Ｂ、及び、Ｒ^２３ＢとＲ^２４Ｂ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、Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂからなる群から選ばれる少なくとも１つは、式（１−Ｔ）で表される基である。］
［７］前記式（２−Ｂ）で表される金属錯体が、式（２−Ｂ１）で表される金属錯体、式（２−Ｂ２）で表される金属錯体、式（２−Ｂ３）で表される金属錯体、式（２−Ｂ４）で表される金属錯体又は式（２−Ｂ５）で表される金属錯体である、［６］に記載の組成物。

［式中、
Ｍ^２、ｎ^３、ｎ^４、Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ、Ｒ^２４Ｂ及びＡ^３−Ｇ^２−Ａ^４は、前記と同じ意味を表す。
ｎ^３１及びｎ^３２は、それぞれ独立に、１以上の整数を表し、ｎ^３１＋ｎ^３２は２又は３である。Ｍ^２がロジウム原子又はイリジウム原子の場合、ｎ^３１＋ｎ^３２は３であり、Ｍ^２がパラジウム原子又は白金原子の場合、ｎ^３１＋ｎ^３２は２である。
Ｒ^１５Ｂ、Ｒ^１６Ｂ、Ｒ^１７Ｂ及びＲ^１８Ｂは、それぞれ独立に、水素原子又は式（１−Ｔ）で表される基を表す。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。Ｒ^１５ＢとＲ^１６Ｂ、Ｒ^１６ＢとＲ^１７Ｂ、及び、Ｒ^１７ＢとＲ^１８Ｂ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、式（２−Ｂ１）及び式（２−Ｂ３）中、Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂからなる群から選ばれる少なくとも１つは、式（１−Ｔ）で表される基であり、式（２−Ｂ２）中、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂからなる群から選ばれる少なくとも１つは、式（１−Ｔ）で表される基であり、式（２−Ｂ４）中、Ｒ^１１Ｂ、Ｒ^１４Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂからなる群から選ばれる少なくとも１つは、式（１−Ｔ）で表される基であり、式（２−Ｂ５）中、Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^２１Ｂ、Ｒ^２２Ｂ、Ｒ^２３Ｂ及びＲ^２４Ｂからなる群から選ばれる少なくとも１つは、式（１−Ｔ）で表される基である。］
［８］前記Ｒ^１Ｔが、置換基を有していてもよいアルキル基、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、又は、式（Ｄ−Ｃ）で表される基である、［１］〜［７］のいずれかに記載の組成物。

［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。
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。複数存在するＴ^ＤＡは、同一でも異なっていてもよい。］

［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。複数存在する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。
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。複数存在するＴ^ＤＡは、同一でも異なっていてもよい。］

［式中、
ｍ^ＤＡ１は、０以上の整数を表す。
Ａｒ^ＤＡ１は、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。
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。］
［９］式（Ｈ−１）で表される化合物を更に含有する、［１］〜［８］のいずれかに記載の組成物。

［式中、
Ａｒ^Ｈ１及びＡｒ^Ｈ２は、それぞれ独立に、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。
ｎ^Ｈ１及びｎ^Ｈ２は、それぞれ独立に、０又は１を表す。ｎ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。複数存在するｎ^Ｈ２は、同一でも異なっていてもよい。
ｎ^Ｈ３は、０以上１０以下の整数を表す。
Ｌ^Ｈ１は、アリーレン基、２価の複素環基、又は、−［Ｃ（Ｒ^Ｈ１１）_２］ｎ^Ｈ１１−で表される基を表し、これらの基は置換基を有していてもよい。Ｌ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。ｎ^Ｈ１１は、１以上１０以下の整数を表す。Ｒ^Ｈ１１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｈ１１は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｌ^Ｈ２は、−Ｎ（−Ｌ^Ｈ２１−Ｒ^Ｈ２１）−で表される基を表す。Ｌ^Ｈ２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^Ｈ２１は、単結合、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。Ｒ^Ｈ２１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。］
［１０］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、酸化防止剤及び溶媒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］〜［９］のいずれかに記載の組成物。
［１１］［１］〜［１０］のいずれかに記載の組成物を含有する発光素子。 The present invention provides the following [1] to [11].
[1] A composition comprising a metal complex represented by formula (1) and a metal complex represented by formula (2).

[Where:
M represents a rhodium atom, a palladium atom, an iridium atom, or a platinum atom.
n ¹ represents an integer of 1 or more, n ² represents an integer of 0 or more, and n ¹ + n ² is 2 or 3.
When M is 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 represents a carbon atom or a nitrogen atom. When a plurality of E ¹ are present, they may be the same or different.
Ring B represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, 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 B are present, they may be the same or different.
Z ^1A represents a group represented by ^═N— or a group represented by ═C (R ^Z1A ) —. When a plurality of Z ^1A are present, they may be the same or different. R ^Z1A represents 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, and these groups are substituent groups. You may have.
R ¹ represents an alkyl group having 2 to 30 carbon atoms, and these groups may have a substituent. When a plurality of R ¹ are present, they may be the same or different.
Ar ^1A represents a group represented by the formula (Ar-1A). When a plurality of Ar ^1A are present, they may be the same or different.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represent 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 together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ]

[Where:
Ring A represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
R ² and R ³ each independently represents 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, The group may have a substituent. ]

[Where:
M ² represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ³ represents an integer of 1 or more, n ⁴ represents an integer of 0 or more, and n ³ + n ⁴ is 2 or 3.
When M ² is a rhodium atom or an iridium atom, n ³ + n ⁴ is 3, and when M ² is a palladium atom or a platinum atom, n ³ + n ⁴ is 2.
E ⁴ represents a carbon atom or a nitrogen atom. When a plurality of E ⁴ are present, they may be the same or different.
Ring L ¹ represents a 6-membered aromatic heterocyclic ring, and this ring may have a substituent. When a plurality of such substituents are present, 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 are present, they may be the same or different.
Ring L ² represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, these rings may have a substituent. When a plurality of such substituents are present, 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 are present, they may be the same or different.
The substituent that the ring L ¹ may have and the substituent that the ring L ² may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
At least one ring selected from the group consisting of ring L ¹ and ring L ² has a group represented by the formula (1-T) as a substituent. When a plurality of groups represented by the formula (1-T) are present, they may be the same or different.
A ³ -G ² -A ⁴ represents a bidentate ligand of the anionic. A ³ and A ⁴ each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. G ² represents a single bond or an atomic group constituting a bidentate ligand together with A ³ and A ⁴ . When a plurality of A ³ -G ² -A ⁴ are present, they may be the same or different. ]

[Wherein R ^1T represents 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, and these groups are substituted. It may have a group. ]
[2] The composition according to [1], wherein the metal complex represented by the formula (1) is a metal complex represented by the formula (1-1).

[Where:
M, Z ^1A , n ¹ , n ² , R ¹ , Ar ^1A and A ¹ -G ¹ -A ² represent the same meaning as described above.
Ring B ¹ represents a benzene ring, a pyridine ring or a diazabenzene ring, and E ^1B , E ^2B , E ^3B and E ^4B each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^1B , E ^2B , E ^3B and E ^4B are present, they may be the same or different. When E ^1B is a nitrogen atom, R ^1B does not exist. When E ^2B is a nitrogen atom, R ^2B does not exist. When E ^3B is a nitrogen atom, R ^3B does not exist. When E ^4B is a nitrogen atom, R ^4B does not exist.
R ^1B , R ^2B , R ^3B and R ^4B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group Represents a group or a halogen atom, and these groups optionally have a substituent. When there are a plurality of R ^1B , R ^2B , R ^3B and R ^4B , they may be the same or different. R ^1B and R ^2B , R ^2B and R ^3B , and R ^3B and R ^4B may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
[3] The composition according to [2], wherein the metal complex represented by the formula (1-1) is a metal complex represented by the formula (1-2).

[Wherein, M, Z ^1A , n ¹ , n ² , R ¹ , Ar ^1A , A ¹ -G ¹ -A ² , R ^1B , R ^2B , R ^3B and R ^4B represent the same meaning as described above. ]
[4] The composition according to any one of [1] to [3], wherein the group represented by the formula (Ar-1A) is a group represented by the formula (Ar-2A).

[Wherein R ² and R ³ represent the same meaning as described above.
Ring A ¹ represents a benzene ring, a pyridine ring or a diazabenzene ring, and E ^1A , E ^2A and E ^3A each independently represent a nitrogen atom or a carbon atom. When E ^1A is a nitrogen atom, R ^1A does not exist. When E ^2A is a nitrogen atom, R ^2A does not exist. When E ^3A is a nitrogen atom, R ^3A does not exist.
R ^1A , R ^2A and R ^3A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or halogen. Represents an atom, and these groups optionally have a substituent. R ^1A and R ^2A , and R ^2A and R ^3A may be bonded to each other to form a ring together with the atoms to which they are bonded. ]
[5] The composition according to [4], wherein the group represented by the formula (Ar-2A) is a group represented by the formula (Ar-3A).

[Wherein, R ² , R ³ , R ^1A , R ^2A and R ^3A represent the same meaning as described above. ]
[6] The composition according to any one of [1] to [5], wherein the metal complex represented by the formula (2) is a metal complex represented by the formula (2-B).

[Where:
M ² , n ³ , n ⁴ and A ³ -G ² -A ⁴ represent the same meaning as described above.
Ring L ^1B represents a pyridine ring or a pyrimidine ring, Ring L ^2B represents a benzene ring, a pyridine ring or a diazabenzene ring, and E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B each independently represents a nitrogen atom or a carbon atom. When there are a plurality of E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B , they may be the same or different. When E ^11B is a nitrogen atom, R ^11B does not exist. When E ^12B is a nitrogen atom, R ^12B does not exist. When E ^13B is a nitrogen atom, R ^13B does not exist. When E ^14B is a nitrogen atom, R ^14B does not exist. When E ^21B is a nitrogen atom, R ^21B does not exist. When E ^22B is a nitrogen atom, R ^22B does not exist. When E ^23B is a nitrogen atom, R ^23B does not exist. When E ^24B is a nitrogen atom, R ^24B does not exist.
R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B each independently represent a hydrogen atom or a group represented by the formula (1-T). When there are a plurality of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B , they may be the same or different. R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , R ^11B and R ^21B , R ^21B and R ^22B , R ^22B and R ^23B , and R ^23B and R ^24B are combined, You may form the ring with the atom to which each couple | bonds. However, at least one selected from the group consisting of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T). ]
[7] The metal complex represented by the formula (2-B) is a metal complex represented by the formula (2-B1), a metal complex represented by the formula (2-B2), or a formula (2-B3). The composition according to [6], which is a metal complex represented by formula (2-B4) or a metal complex represented by formula (2-B5).

[Where:
M ² , n ³ , n ⁴ , R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B , R ^24B and A ³ -G ² -A ⁴ represent the same meaning as described above.
n ³¹ and n ³² each independently represent an integer of 1 or more, and n ³¹ + n ³² is 2 or 3. When M ² is a rhodium atom or an iridium atom, n ³¹ + n ³² is 3, and when M ² is a palladium atom or a platinum atom, n ³¹ + n ³² is 2.
R ^15B , R ^16B , R ^17B and R ^18B each independently represent a hydrogen atom or a group represented by the formula (1-T). When there are a plurality of R ^15B , R ^16B , R ^17B and R ^18B , they may be the same or different. R ^15B and R ^16B , R ^16B and R ^17B , and R ^17B and R ^18B may be bonded to each other to form a ring together with the atoms to which they are bonded. However, in formula (2-B1) and formula (2-B3), at least one selected from the group consisting of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is In the formula (2-B2), at least one selected from the group consisting of R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T): In the formula (2-B4), at least one selected from the group consisting of R ^11B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T). In the formula (2-B5), at least one selected from the group consisting of R ^11B , R ^12B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T). And a group represented by the formula (1-T) A. ]
[8] The R ^1T may have a substituent, an alkyl group, a group represented by the formula (DA), a group represented by the formula (DB), or a formula (D- The composition according to any one of [1] to [7], which is a group represented by C).

[Where:
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 optionally have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally 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 optionally have a substituent. A plurality of ^TDAs may be the same or different. ]

[Where:
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 optionally have a substituent. A plurality of ^GDA 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 optionally have a substituent. A plurality of ^TDAs may be the same or different. ]

[Where:
m ^DA1 represents an integer of 0 or more.
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar ^DA1 are present, they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]
[9] The composition according to any one of [1] to [8], further containing a compound represented by the formula (H-1).

[Where:
Ar ^H1 and Ar ^H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
n ^H1 and n ^H2 each independently represent 0 or 1. When a plurality of n ^H1 are present, they may be the same or different. A plurality of n ^H2 may be the same or different.
n ^H3 represents an integer of 0 or more and 10 or less.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R ^H11 ) ₂ ] n ^H11 —, and these groups ^optionally have a substituent. When a plurality of L ^H1 are present, they may be the same or different. n ^H11 represents an integer of 1 or more and 10 or less. R ^H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
L ^H2 represents a group represented by -N (-L ^H21 -R ^H21 )-. When a plurality of L ^H2 are present, they may be the same or different. L ^H21 represents a single bond, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. R ^H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. ]
[10] Further containing 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, an antioxidant and a solvent, [1] to [9] The composition in any one of.
[11] A light emitting device comprising the composition according to any one of [1] to [10].

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

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

<Explanation of common terms>
Terms commonly used in this 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 the metal complex, the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.

The “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ or more (for example, 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 other embodiments.

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

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

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

The “alkyl group” may be linear or branched. The number of carbon atoms of the linear alkyl group is usually 1 to 50, preferably 1 to 30, preferably 1 to 15, more preferably 1 without including the number of carbon atoms of the substituent. -10. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, preferably 3 to 15, more preferably 3 to 3, not including the carbon atoms of the substituent. 10.
The alkyl group may have a substituent. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl group, hexyl group and heptyl. Group, octyl group, 2-ethylhexyl group, 3-propylheptyl group, decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-hexyldecyl group, dodecyl group and the like. The alkyl group may be a group in which some or all of the hydrogen atoms in these groups are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like. Examples of such an alkyl group include a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, a perfluorooctyl group, a 3-phenylpropyl group, and 3- (4-methylphenyl) propyl. Group, 3- (3,5-di-hexylphenyl) propyl group, 6-ethyloxyhexyl group.
The number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30 and more preferably 4 to 20 without including the number of carbon atoms of the substituent.
The cycloalkyl group may have a substituent. Examples of the cycloalkyl group include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

“Aryl group” means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The carbon atom number of an aryl group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-20, More preferably, it is 6-10.
The aryl group may have a substituent. As the aryl group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, Examples include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group and the like. The aryl group may be a group in which some or all of the hydrogen atoms in these groups are 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 a linear alkoxy group is 1-40 normally without including the carbon atom number of a substituent, Preferably it is 4-10. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The alkoxy group may have a substituent. Examples of the alkoxy group include methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2 -Ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group and the like. The alkoxy group may be a group in which part or all of the hydrogen atoms in these groups are substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
The number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The cycloalkoxy group may have a substituent. Examples of the cycloalkoxy group include a cyclohexyloxy group.

The number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
The aryloxy group may have a substituent. Examples of the aryloxy group include a phenoxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 1-anthracenyloxy group, a 9-anthracenyloxy group, and a 1-pyrenyloxy group. The aryloxy group may be a group in which some or all of the 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.

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

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

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

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

The “alkenyl group” may be linear or branched. The carbon atom number of a linear alkenyl group is 2-30 normally without including the carbon atom number of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkenyl group and the cycloalkenyl group may have a substituent. Examples of the alkenyl group include a vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4-pentenyl group, 1-hexenyl group, 5-hexenyl group, Examples include 7-octenyl groups and groups in which some or all of the hydrogen atoms in these groups have been substituted with substituents. Examples of the cycloalkenyl group include a cyclohexenyl group, a cyclohexadienyl group, a cyclooctatrienyl group, a norbornylenyl group, and a group in which part or all of the hydrogen atoms in these groups are substituted with a substituent. .

The “alkynyl group” may be linear or branched. The carbon atom number of an alkynyl group is 2-20 normally without including the carbon atom of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent. Examples of the alkynyl group include ethynyl group, 1-propynyl group, 2-propynyl group, 2-butynyl group, 3-butynyl group, 3-pentynyl group, 4-pentynyl group, 1-hexynyl group, 5-hexynyl group, And the group by which one part or all part of the hydrogen atom in these groups was substituted by the substituent is mentioned. Examples of the cycloalkynyl group include a cyclooctynyl group.

The “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The carbon atom number of an arylene group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-30, More preferably, it is 6-18.
The arylene group may have a substituent. Examples of the arylene group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthacenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, a chrysenediyl group, and these groups. Examples include a group in which part or all of the hydrogen atoms are substituted with a substituent. The arylene group is preferably a group represented by Formula (A-1) to Formula (A-20). The arylene group includes a group in which a plurality of these groups are bonded.

In the formula, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, preferably a hydrogen atom or an alkyl group , A cycloalkyl group, an aryl group or a monovalent heterocyclic group. A plurality of R and R ^a may be the same or different, and R ^a may be bonded to each other to form a ring together with the atoms to which each is bonded.

The carbon atom number of a bivalent heterocyclic group is 2-60 normally without including the carbon atom number of a substituent, Preferably, it is 3-20, More preferably, it is 4-15.
The divalent heterocyclic group may have a substituent. Examples of the divalent heterocyclic group include pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, A divalent group obtained by removing two hydrogen atoms from a hydrogen atom directly bonded to a carbon atom or a hetero atom constituting a ring from diazole or triazole. The divalent heterocyclic group may be a group in which part or all of the hydrogen atoms in these groups are substituted with a substituent. The divalent heterocyclic group is preferably a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

In the formula, 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, and the like. The crosslinking group is preferably a group represented by any one of formulas (B-1) to (B-17). These groups may have a substituent.

  “Substituent” refers to 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, carbon atom It represents an alkenyl group, a cycloalkenyl group, an alkynyl group or a cycloalkynyl group having a number of 2 or more. The substituent may be a crosslinking group.

<Metal Complex Represented by Formula (1)>
The metal complex represented by the formula (1) is usually a metal complex that exhibits phosphorescence at room temperature (25 ° C.), and preferably a metal complex that emits light from a triplet excited state at room temperature.

Coordinated metal complex represented by formula (1) is as defined and M is a central metal, and a ligand which is defined the number of index n ^1, the number of index n ² It consists of a child.

  M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, since the light emitting efficiency of the light emitting device containing the composition of the present embodiment is more excellent.

When M is 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 is preferably a carbon atom.

The number of carbon atoms of the aromatic hydrocarbon ring in ring B is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18 without including the number of carbon atoms of the substituent.
Examples of the aromatic hydrocarbon ring in ring B include a benzene ring, a naphthalene ring, an indene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, and a ring in which these rings are condensed. The aromatic hydrocarbon ring in ring B is preferably a benzene ring, naphthalene ring, indene ring, fluorene ring, phenanthrene ring or dihydrophenanthrene ring, more preferably a benzene ring, fluorene ring or dihydrophenanthrene ring, More preferably, it is a benzene ring, and these rings may have a substituent.

The number of carbon atoms of the aromatic heterocyclic ring in ring B is usually 4 to 60, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The aromatic heterocycle in ring B includes pyrrole ring, diazole ring, furan ring, thiophene ring, pyridine ring, diazabenzene ring, azanaphthalene ring, diazanaphthalene ring, indole ring, benzodiazole ring, benzofuran ring, benzothiophene. Examples thereof include a ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a ring obtained by condensing an aromatic ring with these rings. The aromatic heterocycle in ring B is preferably a pyrrole ring, a diazole ring, a furan ring, a thiophene ring, a pyridine ring, a diazabenzene ring, an azanaphthalene ring, a diazanaphthalene ring, an indole ring, a benzodiazole ring, a benzofuran ring, A benzothiophene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, more preferably a pyridine ring, a diazabenzene ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, more preferably a pyridine ring or a diazabenzene ring, These rings may have a substituent.

Ring B is preferably a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocyclic ring, because the light-emitting device containing the composition of the present embodiment is more excellent in luminous efficiency. More preferably, it is 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, and more preferably a benzene ring, a pyridine ring or a diazabenzene ring, Particularly preferred are benzene rings, which may have a substituent. When ring B is a 6-membered aromatic heterocyclic ring, E ¹ is preferably a carbon atom.

  As the substituent that the ring B may have, 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 is preferable. , An alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom is more preferable, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic ring. A group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is particularly preferred, an aryl group is particularly preferred, and these groups may further have a substituent.

  As the aryl group in the substituent which ring B may have, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a dihydrophenanthrenyl group, a fluorenyl group or a pyrenyl group is preferable, and a phenyl group, a naphthyl group or A fluorenyl group is more preferred, a phenyl group is still more preferred, and these groups may have a substituent.

  Examples of the monovalent heterocyclic group in the substituent that ring B may have include a pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, azacarbazolyl group A diazacarbazolyl group, a phenoxazinyl group or a phenothiazinyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group or a carbazolyl group is more preferable, and a pyridyl group, a pyrimidinyl group or a triazinyl group is more preferable. More preferably, these groups may have a substituent.

  In the substituted amino group in the substituent that the ring B may have, the amino group preferably has an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups are further substituted. It may have a group. Examples and preferred ranges of the aryl group in the substituent that the amino group has are the same as examples and preferred ranges of the aryl group in the substituent that the ring B may have. Examples and preferred ranges of the monovalent heterocyclic group in the substituent that the amino group has are the same as examples and preferred ranges of the monovalent heterocyclic group in the substituent that the ring B may have.

  Among the substituents that the ring B may have, as the aryl group, monovalent heterocyclic group, and substituted amino group, the light emitting device containing the composition of the present embodiment is more excellent in luminous efficiency. A group represented by (DA), (DB) or (DC) is preferred, and a group represented by formula (DA) or (DC) is more preferred.

[Group represented by formula (DA), (DB) or (DC)]
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably an integer of 2 or less, Preferably 0 or 1. m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are preferably the same integer, and m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are More preferably, they are the same integer.

G ^DA is preferably a group represented by the formula (GDA-11) ~ formula (GDA-15), more preferably a group represented by the formula (GDA-11) ~ formula (GDA-14) And more preferably a group represented by the formula (GDA-11) or the formula (GDA-14), particularly preferably a group represented by the formula (GDA-11).

Where
* Is, ^{Ar DA1} in the formula (D-A), formula (D-B) in ^{Ar DA1,} formula (D-B) ^Ar in ^DA2, or represents a bond between ^{Ar DA3} in the formula (D-B).
** is, ^{Ar DA2} in the formula (D-A), ^{Ar DA2} in the formula (D-B), ^Ar in the formula (D-B) ^DA4, or represents a bond between ^{Ar DA6} in the formula (D-B) .
*** is, ^{Ar DA3} in formula (D-A), ^{Ar DA3} in formula (D-B), ^{Ar DA5} in formula (D-B), or, the bond between ^{Ar DA7} in formula (D-B) Represent.
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 a plurality of ^RDA are present, 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 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably a phenylene group, a ^fluorenediyl group or a carbazolediyl group, more preferably a formula (A-1) to a formula (A-3), Formula (A-8), Formula (A-9), Formula (AA-10), Formula (AA-11), Formula (AA-33) or Formula (AA-34) More preferably a group represented by formula (ArDA-1) to formula (ArDA-5), particularly preferably a group represented by formula (ArDA-1) to formula (ArDA-3). And particularly preferably a group represented by the formula (ArDA-1).

Where
R ^DA represents 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 optionally have a substituent. When two or more ^RDB exists, 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, and still more preferably an aryl group. The group may have a substituent.

T ^DA is preferably a group represented by the formula (TDA-1) ~ formula (TDA-3), more preferably a group represented by the formula (TDA-1).

In the formula, R ^DA and R ^DB represent the same meaning as described above.

  The group represented by the formula (DA) is preferably a group represented by the formula (D-A1) to the formula (D-A4), more preferably the formula (D-A1) or the formula (D- A3) or a group represented by formula (D-A4), more preferably a group represented by formula (D-A1) or formula (D-A4), and particularly preferably a group represented by formula (D-A1). It is group represented by these.

Where
R ^p1 , R ^p2 , R ^p3 and R ^p4 each independently represents 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. A plurality of np1 may be the same or different.

  The group represented by the formula (D-B) is preferably a group represented by the formula (D-B1) to the formula (D-B3), more preferably the formula (D-B1) or the formula (D- A group represented by B3), and more preferably a group represented by the formula (D-B1).

Where
R ^p1 , R ^p2 and R ^p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. When there are a plurality of np1 and np2, they may be the same or different.

  The group represented by the formula (D-C) is preferably a group represented by the formula (D-C1) to the formula (D-C4), more preferably the formula (D-C1) to the formula (D- C3), more preferably a group represented by formula (D-C1) or (D-C2), and particularly preferably a group represented by formula (D-C1). .

Where
R ^p4 , R ^p5 and R ^p6 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When a plurality of R ^p4 , R ^p5 and R ^p6 are present, they may be the same or different.
np4 represents an integer of 0 to 4, np5 represents an integer of 0 to 5, and np6 represents an integer of 0 to 5.

  np1 is preferably 0 or 1, more preferably 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0. np4 is preferably an integer of 0 to 2. np5 is preferably an integer of 1 to 3. np6 is preferably an integer of 0 to 2.

R ^p1 , R ^p2 , R ^p3 , R ^p4 , R ^p5 and R ^p6 are preferably alkyl groups or cycloalkyl groups, more preferably methyl groups, ethyl groups, isopropyl groups, tert-butyl groups, hexyl groups, A 2-ethylhexyl group, a cyclohexyl group or a tert-octyl 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 group represented by a formula (DA), group represented by a formula (DA-1)-a formula (DA-12) is mentioned, for example.

In the formula, ^RD represents a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group. Represents. When two or more ^RD exists, they may be the same or different.

  Examples of the group represented by the formula (D-B) include groups represented by the formula (D-B-1) to the formula (D-B-4).

In the formula, ^RD represents the same meaning as described above.

  Examples of the group represented by the formula (D-C) include groups represented by the formula (D-C-1) to the formula (D-C-13).

In the formula, ^RD represents the same meaning as described above.

^RD is 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.

  When there are a plurality of substituents that the ring B may have, they may be bonded to each other to form a ring together with the atoms to which they are bonded, but the metal complex represented by the formula (1) Since the maximum peak wavelength of the emission spectrum becomes a short wavelength, it is preferable not to form a ring.

  Examples of the substituent that the ring B may have further include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent heterocyclic ring. Group, substituted amino group or halogen atom is preferable, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, monovalent heterocyclic group, substituted amino group or fluorine atom is more preferable, alkyl group, cycloalkyl A group or an aryl group is more preferable, an alkyl group is particularly preferable, and these groups may further have a substituent.

  Examples of the aryl group, monovalent heterocyclic group, or substituted amino group in the substituent that the substituent that the ring B may have further may have further examples and preferred ranges thereof may include the ring B. Examples of preferred aryl groups, monovalent heterocyclic groups, and substituted amino groups and the preferred ranges thereof are the same.

Z ^1A is preferably a group represented by ═N—.

R ^Z1A is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably a hydrogen atom, An alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and particularly preferably a hydrogen atom, and these groups are further substituted. It may have a group.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group or substituted amino group in R ^Z1A are examples of the aryl group, monovalent heterocyclic group or substituted amino group in the substituent that ring B may have. And the same as the preferred range.

Examples and preferred ranges of the substituent that R ^Z1A may have are the same as examples and preferred ranges of the substituent that the substituent that ring B may further have.

The number of carbon atoms of the alkyl group in R ¹ is preferably 3 or more, more preferably 4 or more, and even more preferably 5 or more, not including the number of carbon atoms of the substituent. Further, the number of carbon atoms of the alkyl group in R ¹ is preferably 30 or less, more preferably 20 or less, even more preferably 15 or less, and particularly preferably, without including the number of carbon atoms of the substituent. It is 10 or less, and particularly preferably 8 or less.

The substituent that R ¹ may have is preferably 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. More preferably, it is a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, and more preferably a cycloalkyl group or an aryl group. The group may further have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group or substituted amino group in the substituent that R ¹ may have are the aryl group, monovalent in the substituent that ring B may have, and the like. This is the same as the examples and preferred ranges of the heterocyclic group or substituted amino group.

R ¹ is preferably an alkyl group having 2 to 30 carbon atoms that does not have a substituent because synthesis of the metal complex represented by the formula (1) is facilitated.

R ¹ is preferably a branched alkyl group having 3 to 30 carbon atoms, more preferably a branched alkyl group having 3 to 15 carbon atoms, because the light emitting efficiency of the light emitting device of this embodiment is more excellent. More preferably, it is a branched alkyl group having 3 to 10 carbon atoms, particularly preferably a branched alkyl group having 4 to 10 carbon atoms, and particularly preferably 5 to 8 carbon atoms. A branched alkyl group. These groups preferably have no substituent.

In the alkyl group in R ¹ , the branched alkyl group includes isopropyl group, sec-butyl group, isobutyl group, tert-butyl group, isopentyl group, neopentyl group, tert-pentyl group, 1,1-dimethylbutyl group, 1 -Ethylbutyl group, 2-ethylbutyl group, 1,1-dimethylpentyl group, 1,1-diethylpropyl group, 1,2-dimethylpentyl group, 1,1-dimethylhexyl group, 1-ethyl-1-methylpentyl group 1,1,3,3-tetramethylbutyl group, 1,2-dimethylhexyl group, 1-propylpentyl group, 2-ethylhexyl group, 1,1-dimethylheptyl group, 1,1-dipropylbutyl group, 1-butylhexyl group, 1-propylheptyl group, 1,1,3,7-tetramethyloctyl group and 1,1,2-trie A tiloctyl group is preferred.

[Group Represented by (Formula Ar-1A)]
Examples and preferred ranges of aromatic hydrocarbon rings in ring A are the same as examples and preferred ranges of aromatic hydrocarbon rings in ring B. Examples and preferred ranges of the aromatic heterocycle in ring A are the same as examples and preferred ranges of the aromatic hydrocarbon ring in ring B.

  Ring A is preferably a 5-membered or 6-membered aromatic hydrocarbon ring, or a 5-membered or 6-membered aromatic heterocyclic ring, since the light-emitting device containing the composition of the present embodiment is more excellent in luminous efficiency. More preferably, it is 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, and more preferably a benzene ring, a pyridine ring or a diazabenzene ring, Particularly preferred are benzene rings, which may have a substituent.

  As the substituent that the ring A may have, 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 is preferable. , An alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom is more preferable, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic ring. A group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is particularly preferred, and these groups may further have a substituent.

  Examples and preferred ranges of the aryl group, monovalent heterocyclic group or substituted amino group in the substituent that the ring A may have are the aryl group, monovalent in the substituent that the ring B may have. The examples are the same as the examples and preferred ranges of the heterocyclic group or substituted amino group.

  When there are a plurality of substituents that the ring A may have, they may be bonded to each other to form a ring together with the atoms to which they are bonded, but the metal complex represented by the formula (1) Since the maximum peak wavelength of the emission spectrum becomes a short wavelength, it is preferable not to form a ring.

  Examples of the substituents that the substituent that the ring A may have and the substituents that the substituent that the ring B may optionally have further include examples of the substituent that the ring A may further have. Same as example and preferred range.

R ² and R ³ are preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a fluorine atom, more preferably an alkyl group, A cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and particularly preferably an alkyl group. It may have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group or substituted amino group in R ² and R ³ are the aryl group, monovalent heterocyclic group or substituted amino group in the substituent that ring B may have. Examples of groups are the same as the preferred ranges.

The alkyl group in R ² and R ³ is preferably an alkyl group having 1 to 7 carbon atoms, more preferably the number of carbon atoms, because the synthesis of the metal complex represented by the formula (1) is facilitated. It is a 1-5 alkyl group, More preferably, it is a C1-C3 alkyl group, It is especially preferable that these groups do not have a substituent.

Examples and preferred ranges of substituents that R ² and R ³ may have are the same as examples and preferred ranges of substituents that R ¹ may have.

R ² and R ³ are preferably the same.

  The group represented by the formula (Ar-1A) is preferably a group represented by the formula (Ar-2A) since the light emitting efficiency of the light emitting device containing the composition of the present embodiment is more excellent.

E ^1A , E ^2A and E ^3A are preferably carbon atoms.

R ^1A , R ^2A and R ^3A are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, and more Preferably, it is a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these The group may have a substituent.

R ^1A and R ^3A are particularly preferably a hydrogen atom, an alkyl group, or an aryl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.
R ^2A is particularly preferably a hydrogen atom, an alkyl group or an aryl group, particularly preferably an alkyl group or an aryl group, and still more preferably an alkyl group, and these groups have a substituent. It may be.

Examples of the aryl group, monovalent heterocyclic group or substituted amino group in R ^1A , R ^2A and R ^3A and preferred ranges thereof are the aryl group and monovalent heterocyclic group in the substituent that Ring B may have. Or it is the same as the example and preferable range of a substituted amino group.

Examples and preferred ranges of substituents that R ^1A , R ^2A and R ^3A may have are examples and preferred ranges of substituents that ring B may further have. Is the same.

R ^1A and R ^2A and R ^2A and R ^3A may be bonded to each other to form a ring together with the atoms to which they are bonded, but it is preferable that no ring is formed.

When ring A ¹ is a pyridine ring, a pyridine ring in which E ^1A is a nitrogen atom is preferable.
When ring A ¹ is a diazabenzene ring, a pyrimidine ring in which E ^1A and E ^3A are nitrogen atoms is preferred.
Ring ^{A 1} is benzene ring.

[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 subscript n ¹ .

Where
* Represents a site that binds to M.
R ^L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent. A plurality of R ^L1 may be the same or different.
R ^L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent.

R ^L1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a fluorine atom, more preferably a hydrogen atom or an alkyl group, still more preferably a hydrogen atom, and these groups are substituted. It may have a group.

R ^L2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent. Good.

<Metal Complex Represented by Formula (1-1)>
The metal complex represented by the formula (1) is preferably a metal complex represented by the formula (1-1) because the luminous efficiency of the light emitting device containing the composition of the present embodiment is more excellent.

E ^1B , E ^2B , E ^3B and E ^4B are preferably carbon atoms.

R ^1B , R ^2B , R ^3B and R ^4B are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom. More preferably, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group. Yes, these groups may further have a substituent.

R ^1B , R ^3B and R ^4B are particularly preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups may further have a substituent.
R ^2B is particularly preferably a hydrogen atom, an alkyl group or an aryl group, particularly preferably a hydrogen atom or an aryl group, and still more preferably a hydrogen atom, and these groups further have a substituent. You may do it.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group or substituted amino group in R ^1B , R ^2B , R ^3B and R ^4B are the aryl group and monovalent group in the substituent that ring B may have. The examples are the same as the examples and preferred ranges of the heterocyclic group or substituted amino group.

Examples of the substituent that R ^1B , R ^2B , R ^3B, and R ^4B may have and preferred ranges thereof are examples of the substituent that the ring B may further have. And the same as the preferred range.

When Ring B ¹ is a pyridine ring, ring B ¹ represents a pyridine ring E ^1B is a nitrogen atom, a pyridine ring E ^2B is a nitrogen atom, or, that E ^3B is a pyridine ring is a nitrogen atom Preferably, E ^2B is a pyridine ring which is a nitrogen atom.
When ring B ¹ is a diazabenzene ring, ring B ¹ is preferably a pyrimidine ring in which E ^2B and E ^4B are nitrogen atoms, or a pyrimidine ring in which E ^1B and E ^3B are nitrogen atoms, and E ^2B And E ^4B is more preferably a pyrimidine ring which is a nitrogen atom.
Ring B ¹ is preferably a benzene ring.

  The metal complex represented by the formula (1-1) is preferably a metal complex represented by the formula (1-2) because the light emission efficiency of the light emitting device containing the composition of the present embodiment is more excellent. .

  As a metal complex represented by Formula (1), the metal complex represented by a following formula is mentioned, for example.

Where
Z ^A represents a group represented by —CH═ or a group represented by —N═. If Z ^A is plurally present, they may be the same or different. Z ^A is preferably a group represented by —N═.
Z ^B represents a group represented by -O- or a group represented by -S-.

<Method for Producing Metal Complex Represented by Formula (1)>
The metal complex represented by the formula (1) can be produced, for example, by a method of reacting a ligand compound with a metal compound. You may perform the functional group conversion reaction of the ligand of a metal complex as needed.

The metal complex represented by the formula (1) includes, for example, the step A in which the compound represented by the formula (M-1) is reacted with the metal compound or a hydrate thereof, and the compound obtained in the step A. (Hereinafter also referred to as “metal complex intermediate (1)”) and a compound represented by formula (M-1) or a precursor of a ligand represented by A ¹ -G ¹ -A ^2. It can manufacture by the method including the process B made to react.

In the formula, M, n ¹ , n ² , E ¹ , ring B, Z ^1A , R ¹ , Ar ^1A and A ¹ -G ¹ -A ² represent the same meaning as described above.

  In step A, examples of the metal compound include iridium chloride, tris (acetylacetonato) iridium (III), chloro (cyclooctadiene) iridium (I) dimer, iridium acetate (III) and the like; chloroplatinic acid Platinum compounds such as potassium; palladium compounds such as palladium chloride and palladium acetate; and rhodium compounds such as rhodium chloride. Examples of hydrates of metal compounds include iridium chloride trihydrate and rhodium chloride trihydrate.

  As a metal complex intermediate (1), the metal complex represented by a formula (M-2) is mentioned, for example.

In the formula, M, E ¹ , ring B, Z ^1A , R ¹ , Ar ^1A and A ¹ -G ¹ -A ² represent the same meaning as described above.
n ^{1 ′} represents 1 or 2. When M is a rhodium atom or an iridium atom, n ^{1 ′} is 2. When M is a palladium atom or a platinum atom, n ^{1 ′} is 1.

  In step A, the amount of the compound represented by the formula (M-1) is usually 2 to 20 mol with respect to 1 mol of the metal compound or hydrate thereof.

In Step B, the amount of the compound represented by the formula (M-1) or the precursor of the ligand represented by A ¹ -G ¹ -A ² is 1 mol of the metal complex intermediate (1). Usually, it is 1-100 mol.

  In step B, the reaction is preferably performed in the presence of a silver compound such as silver trifluoromethanesulfonate. When using a silver compound, the quantity is 2-20 mol normally with respect to 1 mol of metal complex intermediates (1).

  Step A and Step B are usually performed in a solvent. Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, and 2-ethoxyethanol; ether solvents such as diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, and diglyme. Halogen compounds such as methylene chloride and chloroform; nitrile solvents such as acetonitrile and benzonitrile; hydrocarbon solvents such as hexane, decalin, toluene, xylene and mesitylene; N, N-dimethylformamide and N, N-dimethylacetamide Amide solvents such as acetone, dimethyl sulfoxide, water and the like.

  In Step A and Step B, the reaction time is usually 30 minutes to 200 hours, and the reaction temperature is usually between the melting point and boiling point of the solvent present in the reaction system.

  The compounds, catalysts, and solvents used in the reaction described in <Method for producing metal complex represented by formula (1)> may be used singly or in combination of two or more.

<Metal Complex Represented by Formula (2)>
The metal complex represented by the formula (2) is usually a metal complex that exhibits phosphorescence at room temperature (25 ° C.), and preferably a metal complex that emits light from a triplet excited state at room temperature.

The metal complex represented by the formula (2) has a central metal M ² , a ligand whose number is defined by the subscript n ³ , and a coordination whose number is defined by the subscript n ⁴ . It is composed of a scale.

M ² is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the light-emitting efficiency of the light-emitting device containing the composition of the present embodiment is more excellent.

When M ² is a rhodium atom or an iridium atom, n ³ is preferably 2 or 3, and more preferably 3.

When M ² is a palladium atom or a platinum atom, n ³ is preferably 2.

E ⁴ is preferably a carbon atom.

Ring L ¹ is preferably a 6-membered aromatic heterocyclic ring having 1 or more and 4 or less nitrogen atoms as a constituent atom, and preferably a 6-membered aromatic having 1 or more and 2 or less nitrogen atoms as a constituent atom. More preferred are group heterocycles, and these rings may have a substituent.
Examples of the ring L ¹ include a pyridine ring, a diazabenzene ring, a quinoline ring and an isoquinoline ring, a pyridine ring, a pyrimidine ring, a quinoline ring or an isoquinoline ring is preferable, and a pyridine ring, a quinoline ring or an isoquinoline ring is more preferable. A ring or an isoquinoline ring is more preferable, and these rings may have a substituent.

Examples and preferred ranges of the aromatic hydrocarbon ring in the ring L ² are the same as examples and preferred ranges of the aromatic hydrocarbon ring in the ring B. Examples and preferred ranges of the aromatic heterocyclic ring in the ring L ² are the same as those of the aromatic hydrocarbon ring and the preferred range in the ring B.

Examples and preferred ranges of ring L ² are the same as examples and preferred ranges of ring B. However, when the ring L ² is a 6-membered aromatic heterocyclic ring, E ⁴ is a carbon atom.

“At least one ring selected from the group consisting of ring L ¹ and ring L ² has a group represented by the formula (1-T) as a substituent” means ring L ¹ and ring L ² It means that the group represented by the formula (1-T) is directly bonded to at least one atom (preferably a carbon atom or a nitrogen atom). In the metal complex represented by the formula (2), when there are a plurality of rings L ¹ and L ² (that is, when n ³ is 2 or 3), among the plurality of rings L ¹ and L ² It suffices that at least one ring has a group represented by the formula (1-T), but all of a plurality of rings L ¹ , all of a plurality of rings L ² , or a plurality of rings L ¹ and all of the rings L ² preferably have a group represented by the formula (1-T), and all of the plurality of rings L ¹ or all of the plurality of rings L ² are represented by the formula (1 It is more preferable to have a group represented by -T), and it is even more preferable that all of the plurality of rings L ² have a group represented by the formula (1-T).

Ring L ² preferably has a group represented by formula (1-T).

As the substituent that the ring L ¹ and the ring L ² may have (substituent other than the group represented by the formula (1-T)), a cyano group, an alkenyl group, or a cycloalkenyl group is preferable. The group may further have a substituent.

When there are a plurality of substituents that the ring L ¹ may have (substituents other than the group represented by formula (1-T)), they are bonded to each other to form a ring together with the atoms to which they are bonded. Although it may form, it is preferable not to form a ring.
When there are a plurality of substituents that the ring L ² may have (substituents other than the group represented by formula (1-T)), they are bonded to each other to form a ring together with the atoms to which each is bonded. Although it may form, it is preferable not to form a ring.
The substituent which ring L ¹ may have (substituent other than the group represented by formula (1-T)) and the substituent which ring L ² may have (formula (1-T)) May be bonded to each other to form a ring with the atoms to which they are bonded, but it is preferable that no ring is formed.

Examples of the anionic bidentate ligand represented by A ³ -G ² -A ⁴ and preferred ranges thereof include examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² and It is the same as a preferable range. In the anionic bidentate ligand represented by A ³ -G ² -A ⁴ , * in the above formula represents a site that binds to M ² . However, the anionic bidentate ligand represented by A ³ -G ² -A ⁴ is different from the ligand whose number is defined by the subscript n ³ .

[Group Represented by Formula (1-T)]
Examples and preferred ranges of the aryl group represented by R ^1T are the same as examples and preferred ranges of the aryl group in the substituent that the ring B may have.
Examples and preferred ranges of the monovalent heterocyclic group represented by R ^1T are the same as examples and preferred ranges of the monovalent heterocyclic group in the substituent that B may have.
Examples and preferred ranges of the substituted amino group represented by R ^1T are the same as examples and preferred ranges of the substituted amino group in the substituent that B may have.

Examples and preferred ranges of the substituent that R ^1T may have are the same as examples and preferred ranges of the substituent that the substituent that ring B may further have.

R ^1T is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, since the luminous efficiency of the light-emitting device containing the composition of the present embodiment is more excellent. A substituted amino group or a fluorine 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 alkyl group or a formula (DA ), (D-B) or (D-C), particularly preferably an alkyl group (particularly an alkyl group having 4 to 8 carbon atoms) or a formula (DA) These groups may have a substituent.

In the groups represented by formulas ( ^DA ) and (DB) in R ^1T, GDA is preferably a group represented by formulas (GDA-11) to (GDA-15), more preferably Is a group represented by formulas (GDA-11) to (GDA-14), more preferably a group represented by formula (GDA-11) or (GDA-14), and particularly preferably GDA-11).

In R ^1T , the group represented by the formula (DA) is preferably a group represented by the formulas (D-A1) to (D-A4), more preferably the formula (D-A1). , (D-A3) or (D-A4), more preferably a group represented by formula (D-A1) or (D-A3), particularly preferably D-A1) (particularly, a group represented by the formula (D-A1) in which np1 is 1, np2 is 0, and ^Rp1 is an alkyl group).

In R ^1T , the group represented by the formula (D-B) is preferably a group represented by the formulas (D-B1) to (D-B3), more preferably the formula (D-B1). Or it is group represented by (D-B3), More preferably, it is group represented by Formula (D-B1).

In R ^1T , the group represented by the formula (D-C) is preferably a group represented by the formulas (D-C1) to (D-C4), more preferably the formula (D-C1). To (D-C3), more preferably a group represented by formula (D-C1) or (D-C2), and particularly preferably a group represented by formula (D-C1). Group.

<Metal Complex Represented by Formula (2-B)>
The metal complex represented by the formula (2) is preferably a metal complex represented by the formula (2-B) since the light emitting efficiency of the light emitting device containing the composition of the present embodiment is more excellent.

E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B are preferably carbon atoms.

When the ring L ^1B is a pyrimidine ring, a pyrimidine ring in which E ^11B is a nitrogen atom is preferable.
Ring L ^1B is preferably a pyridine ring.

When the ring L ^1B has a group represented by the formula (1-T), R ^11B , R ^12B or R ^13B is preferably a group represented by the formula (1-T), and R ^12B or R ^13B Is more preferably a group represented by the formula (1-T), and R ^13B is more preferably a group represented by the formula (1-T).

When ring L ^2B is a pyridine ring, a pyridine ring in which E ^21B is a nitrogen atom, a pyridine ring in which E ^22B is a nitrogen atom, or a pyridine ring in which E ^23B is a nitrogen atom is preferable, and E ^22B is a nitrogen atom. Some pyridine rings are more preferred.
When ring L ^2B is a diazabenzene ring, a pyrimidine ring in which E ^21B and E ^23B are nitrogen atoms, or a pyrimidine ring in which E ^22B and E ^24B are nitrogen atoms is preferable, and E ^22B and E ^24B are nitrogen atoms. A pyrimidine ring is more preferred.
Ring L ^2B is preferably a benzene ring.

When the ring L ^2B has a group represented by the formula (1-T), R ^22B , R ^23B or R ^24B is preferably a group represented by the formula (1-T), and R ^22B or R ^23B Is more preferably a group represented by the formula (1-T), and R ^23B is more preferably a group represented by the formula (1-T).

Ring L ^2B preferably has a group represented by formula (1-T).

An atom to which R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , R ^11B and R ^21B , R ^21B and R ^22B , R ^22B and R ^23B , or R ^23B and R ^24B are bonded to each other. In the case of forming a ring together, the ring to be formed is preferably an aromatic hydrocarbon ring or an aromatic heterocycle, more preferably an aromatic hydrocarbon ring, and a benzene ring, and these rings have a substituent. May be. In the case of forming a ring, examples and preferred ranges of the aromatic hydrocarbon ring and aromatic heterocycle in the ring to be formed are the same as examples and preferred ranges of the aromatic hydrocarbon ring and aromatic heterocycle in ring B, respectively. It is. In the case of forming a ring, examples and preferred ranges of the substituent that the ring may have are examples and preferred ranges of the substituent that the ring B may further have. Is the same.

  Since the metal complex represented by the formula (2-B) is more excellent in luminous efficiency of the light emitting device containing the composition of the present embodiment, the metal complex represented by the formula (2-B1), the formula (2- A metal complex represented by B2), a metal complex represented by formula (2-B3), a metal complex represented by formula (2-B4), or a metal complex represented by formula (2-B5) It is more preferable that it is a metal complex represented by the formula (2-B1), a metal complex represented by the formula (2-B2), or a metal complex represented by the formula (2-B3). More preferably, it is a metal complex represented by 2-B1) or a metal complex represented by formula (2-B2).

R ^15B , R ^16B , R ^17B and R ^18B are preferably hydrogen atoms.

R ^15B and R ^16B , R ^16B and R ^17B , and R ^17B and R ^18B may be bonded to each other to form a ring with the atoms to which they are bonded, but it is preferable that no ring is formed.

  As a metal complex represented by Formula (2), the metal complex represented by a following formula is mentioned, for example.

The metal complex represented by the formula (2) can be obtained from Aldrich, Luminescence Technology Corp. Available from the American Dye Source.
As other methods of obtaining the above, for example, “Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of the American Chemical Society, Vol. Described in JP-T-2004-530254, JP-A-2008-179617, JP-A-2011-105701, JP-T-2007-504272, International Publication No. 2006/121811, and JP-A-2013-147450. Can be synthesized according to the methods described.

<Composition>
The composition of this embodiment is a composition containing the metal complex represented by Formula (1) and the metal complex represented by Formula (2).

  The composition of this embodiment may contain individually 1 type of the metal complex represented by Formula (1), and may contain 2 or more types. The composition of this embodiment may contain individually 1 type of the metal complex represented by Formula (2), and may contain 2 or more types.

  The composition of the present embodiment adjusts the emission color by adjusting the ratio of the content of the metal complex represented by the formula (1) and the content of the metal complex represented by the formula (2). It is also possible to adjust the emission color to white.

  The light emission color of the light emitting element can be confirmed by measuring the light emission chromaticity of the light emitting element and obtaining chromaticity coordinates (CIE chromaticity coordinates). For example, the white luminescent color preferably has a chromaticity coordinate X in the range of 0.20 to 0.55 and a chromaticity coordinate Y in the range of 0.20 to 0.55. More preferably, X of the chromaticity coordinates is in the range of 0.25 to 0.50, and Y of the chromaticity coordinates is in the range of 0.25 to 0.50.

  From the viewpoint of adjusting the emission color of the light emitting device containing the composition of the present embodiment (particularly adjusting the emission color to white), the emission spectrum of the light emitting device containing the composition of the present embodiment is 380 nm or more and 495 nm. Preferably, it has a maximum emission wavelength of less than 400 nm, more preferably has a maximum emission wavelength of 400 nm or more and 490 nm or less, further preferably has a maximum emission wavelength of 420 nm or more and 485 nm or less, and has a maximum emission wavelength of 440 nm or more and 480 nm or less. It is particularly preferable to have it. These maximum emission wavelengths are preferably the maximum emission wavelengths derived from the light emission of the metal complex represented by the formula (1).

  From the viewpoint of adjusting the emission color of the light emitting device containing the composition of the present embodiment (particularly adjusting the emission color to white), the emission spectrum of the light emitting device containing the composition of the present embodiment is 495 nm or more and 750 nm. The maximum emission wavelength is preferably less than 500 nm, the maximum emission wavelength is more preferably 500 nm or more and 680 nm or less, and the maximum emission wavelength is further preferably 505 nm or more and 640 nm or less. These maximum emission wavelengths are preferably maximum emission wavelengths derived from light emission of the metal complex represented by the formula (2).

  From the viewpoint of adjusting the emission color of the light emitting device containing the composition of the present embodiment (particularly adjusting the emission color to white), the content of the metal complex represented by the formula (2) is expressed by the formula (1). When the content of the metal complex represented by 100 is 100 parts by mass, it is preferably 0.01 to 50 parts by mass, more preferably 0.1 to 30 parts by mass, and still more preferably 0.5 to 10 parts by mass. It is a mass part, Most preferably, it is 1-5 mass parts.

<Other ingredients>
The composition of this embodiment is represented by a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (however, a metal complex represented by the formula (1) and a formula (2)). It may be different from a metal complex), and may further contain at least one selected from the group consisting of an antioxidant and a solvent.

[Host material]
Since the luminous efficiency of the light emitting device containing the composition of the present embodiment is more excellent, the composition of the present embodiment is at least one selected from hole injection property, hole transport property, electron injection property, and electron transport property. It is preferable to further contain a host material having a function. The composition of this embodiment may contain 1 type of host materials independently, and may contain 2 or more types.

  When the composition of the present embodiment further contains a host material, the content of the host material is the sum of the metal complex represented by the formula (1), the metal complex represented by the formula (2), and the host material. Is usually 1 to 99 parts by mass, preferably 10 to 90 parts by mass, more preferably 30 to 85 parts by mass, and still more preferably 50 to 80 parts by mass.

The lowest excited triplet state (T ₁ ) possessed by the host material is more excellent in the light emission efficiency of the light-emitting device containing the composition of the present embodiment. Therefore, the lowest excited triplet possessed by the metal complex represented by the formula (1) It is preferable that the energy level be higher than that in the state (T ₁ ).

  As the host material, a light-emitting element containing the composition of this embodiment can be produced by a solution coating process, so that the metal complex represented by formula (1) and the metal complex represented by formula (2) are dissolved. It is preferable that it is soluble in a solvent that can be used.

  The host material is classified into a low molecular compound (low molecular host) and a high molecular compound (polymer host), and the composition of the present embodiment may contain any host material. The host material that may be contained in the composition of the present embodiment is preferably a low molecular compound.

[Low molecular host]
The low molecular weight compound (hereinafter referred to as “low molecular weight host”) preferable as the host material will be described.

  The low molecular host is preferably a compound represented by the formula (H-1).

Ar ^H1 and Ar ^H2 are phenyl group, fluorenyl group, spirobifluorenyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, thienyl group, benzothienyl group, dibenzothienyl group, furyl group, benzofuryl Group, dibenzofuryl group, pyrrolyl group, indolyl group, azaindolyl group, carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxazinyl group or phenothiazinyl group, phenyl group, fluorenyl group, spirobifluorene Nyl group, pyridyl group, pyrimidinyl group, triazinyl group, dibenzothienyl group, dibenzofuryl group, carbazolyl group or azacarbazolyl group is more preferable, fluorenyl group, spirobifluorenyl group, dibenzothienyl group More preferably dibenzofuryl group or a carbazolyl group, especially preferably a group represented by the formula (TDA-3), these groups may have a substituent.

As the substituent that Ar ^H1 and Ar ^H2 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable, and an alkyl group, a cyclo An alkoxy group, an alkoxy group or a cycloalkoxy group is more preferable, an alkyl group or a cycloalkoxy group is more preferable, and these groups may further have a substituent.

n ^H1 is preferably 1. n ^H2 is preferably 0.
n ^H3 is generally an integer of 0 or more and 10 or less, preferably an integer of 0 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and particularly preferably 1.
n ^H11 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 or more and 3 or less, and even more preferably 1.

R ^H11 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and a hydrogen atom or an alkyl group. It is more preferable that these groups may have a substituent.

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

L ^H1 represents formula (A-1) to formula (A-3), formula (A-8) to formula (A-10), formula (AA-1) to formula (AA-6), formula (AA- 10) to a group represented by formula (AA-21) or formula (AA-24) to formula (AA-34), preferably a group represented by formula (A-1), formula (A-2), formula (A A-8), formula (A-9), formula (AA-1) to formula (AA-4), formula (AA-10) to formula (AA-15), formula (AA-33) or formula (AA) -34) is more preferable, and the group represented by formula (A-1), formula (A-2), formula (A-8), formula (AA-2), formula (AA-4), A group represented by formula (AA-10), formula (AA-12), formula (AA-14), or (AA-33) is more preferable, and formula (A-8), formula (AA-10) is more preferable. ), A group represented by formula (AA-12) or formula (AA-14) Is particularly preferable, and a group represented by the formula (AA-14) is particularly preferable.

As the substituent that L ^H1 may have, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group is preferable, and an alkyl group, an alkoxy group, an aryl group Group or a monovalent heterocyclic group is more preferable, an alkyl group, an aryl group or a monovalent heterocyclic group is further preferable, and a monovalent heterocyclic group is particularly preferable, and these groups further have a substituent. Also good.

L ^H21 is preferably a single bond or an arylene group, more preferably a single bond, and this arylene group may have a substituent.

The definition and examples of the arylene group or divalent heterocyclic group represented by L ^H21 are the same as the definitions and examples of the arylene group or divalent heterocyclic group represented by L ^H1 .

R ^H21 is preferably an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.

The definitions and examples of the aryl group and monovalent heterocyclic group represented by R ^H21 are the same as the definitions and examples of the aryl group and monovalent heterocyclic group represented by Ar ^H1 and Ar ^H2 .

Definitions and examples of the substituent that R ^H21 may have are the same as the definitions and examples of the substituent that Ar ^H1 and Ar ^H2 may have.

  The compound represented by the formula (H-1) is preferably a compound represented by the formula (H-2).

In the formula, Ar ^H1 , Ar ^H2 , n ^H3 and L ^H1 represent the same meaning as described above.

  Examples of the compound represented by Formula (H-1) include compounds represented by Formula (H-101) to Formula (H-118).

  Examples of the polymer compound used for the host material include a polymer compound that is a hole transport material described later and a polymer compound that is an electron transport material described later.

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

  Examples of the low molecular weight compound include triphenylamine and derivatives thereof, N, N′-di-1-naphthyl-N, N′-diphenylbenzidine (α-NPD), and N, N′-diphenyl-N, An aromatic amine compound such as N′-di (m-tolyl) benzidine (TPD) can be used.

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

  In the composition of the present embodiment, the content of the hole transport material is usually 100 parts by mass when the total of the metal complex represented by the formula (1) and the metal complex represented by the formula (2) is 100 parts by mass. 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

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

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

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

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

  In the composition of this embodiment, the content of the electron transport material is usually 1 when the total of the metal complex represented by the formula (1) and the metal complex represented by the formula (2) is 100 parts by mass. It is -400 mass parts, Preferably it is 5-150 mass parts.

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

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

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

  Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.

  In the composition of this embodiment, the content of the hole injection material and the electron injection material is 100 parts by mass of the total of the metal complex represented by the formula (1) and the metal complex represented by the formula (2), respectively. In general, it is 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

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

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

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

  Doping ions may be used alone or in combination of two or more.

[Luminescent material]
Luminescent materials (however, different from the metal complex represented by the formula (1) and the metal complex represented by the formula (2)) are classified into low molecular compounds and high molecular compounds. The light emitting material may have a crosslinking group.

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

  Examples of the triplet luminescent complex include the metal complexes shown below.

  Examples of the polymer compound include arylene groups such as a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, an anthracenediyl group, and a pyrenediyl group; two hydrogen atoms from an aromatic amine. And a polymer compound containing an aromatic amine residue such as a group to be removed; and a group selected from divalent heterocyclic groups such as a carbazolediyl group, a phenoxazinediyl group and a phenothiazinediyl group.

  The light emitting material is preferably a triplet light emitting complex or a polymer compound.

  In the composition of the present embodiment, the content of the luminescent material is usually 1 to 100 parts by mass when the total of the metal complex represented by the formula (1) and the metal complex represented by the formula (2) is 100 parts by mass. 400 parts by mass, preferably 5 to 150 parts by mass.

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

[Antioxidant]
The antioxidant is, for example, a compound that is soluble in at least one solvent capable of dissolving the metal complex represented by the formula (1) and the metal complex represented by the formula (2) and does not inhibit light emission and charge transport. It is preferable that Examples of the antioxidant include a phenolic antioxidant and a phosphorus antioxidant.

  In the composition of the present embodiment, the content of the antioxidant is usually 0 when the total of the metal complex represented by the formula (1) and the metal complex represented by the formula (2) is 100 parts by mass. 0.001 to 10 parts by mass.

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

<Ink>
The composition of the present embodiment containing a solvent (hereinafter also referred to as “ink”) is spin coating, casting, micro gravure coating, gravure coating, bar coating, roll coating, wire bar coating. , Dip coating, spray coating, screen printing, flexographic printing, offset printing, ink jet printing, capillary coating, nozzle coating, and other wet methods.

  The viscosity of the ink may be adjusted according to the type of wet method, but when applying a solution such as an inkjet printing method to a printing method that passes through a discharge device, clogging and flight bending at the time of discharge are less likely to occur. Preferably, it is 1 to 20 mPa · s at 25 ° C.

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

  In the ink, the content of the solvent is usually 1000 to 100,000 parts by mass when the total of the metal complex represented by the formula (1) and the metal complex represented by the formula (2) is 100 parts by mass. Preferably it is 2000-20000 mass parts.

<Membrane>
The film of this embodiment contains a metal complex represented by the formula (1) and a metal complex represented by the formula (2). The film can also be referred to as a film composed of the composition of the present embodiment.

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

  The film is made of ink, for example, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method. It can be produced by a wet method such as a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, or a nozzle coating method.

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

<Light emitting element>
The light emitting device of the present embodiment is a light emitting device containing the composition of the present embodiment.
The light emitting device of this embodiment has, for example, an anode, a cathode, and a layer containing the composition of this embodiment provided between the anode and the cathode.

[Layer structure]
The layer containing the composition of the present embodiment is usually at least one of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, and preferably a light emitting layer. . Each of these layers includes a light emitting material, a hole transport material, a hole injection material, an electron transport material, or an electron injection material. In each of these layers, an ink is prepared by dissolving a light emitting material, a hole transport material, a hole injection material, an electron transport material, or an electron injection material in the above-described solvent, and the above-described film is formed using the ink. Can be formed by the same method.

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

  As a material of the hole transport layer, the electron transport layer, the light emitting layer, the hole injection layer, and the electron injection layer, for example, in addition to the composition of the present embodiment, the above-described hole transport material, electron transport material, and light emission, respectively. Examples include materials, hole injection materials, and electron injection materials.

  As for a positive hole transport layer, an electron carrying layer, and a light emitting layer, it is desirable for the material which comprises each layer not to melt | dissolve in the solvent used at the time of formation of an adjacent layer, respectively. In order to avoid dissolution in a solvent, each layer is preferably formed using a material having a crosslinking group. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

  In the light emitting device of this embodiment, as a method of forming each layer such as a light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer, when using a low molecular weight compound, for example, vacuum from powder Examples of the method include vapor deposition and a method of forming a film from a solution or a molten state. When a polymer compound is used, for example, a method of forming a film from a solution or a molten state is used.

  The order, number, and thickness of the layers to be laminated are adjusted in consideration of the external quantum efficiency and the luminance lifetime.

[Substrate / Electrode]
The substrate in the light-emitting element is a substrate that does not change chemically when forming electrodes and forming an organic layer (for example, a light-emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc.) Preferably there is. The substrate may be a substrate made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, the electrode farthest from the substrate is preferably transparent or translucent.

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

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

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

  The preferred embodiment of the present invention has been described above, but the present invention is not limited to the above embodiment.

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

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

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

NMR was measured by the following method.
About 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N, N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol. Or it melt | dissolved in the methylene chloride and measured using the NMR apparatus (The product made from Varian (Varian, Inc.), brand name: INOVA300 or MERCURY 400VX, or the product made from Bruker, brand name: AVANCE600).

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

<Synthesis Examples M1-M5, RM1> Synthesis of Compounds M1-M5 and Metal Complex RM1 Compound M1 was synthesized according to the method described in International Publication No. 2015/145871.
Compounds M2, M4 and M5 were synthesized according to the method described in International Publication No. 2013/146806.
Compound M3 was synthesized according to the method described in WO2005 / 049546.
The metal complex RM1 was synthesized according to the method described in International Publication No. 2009/157424.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 Polymer compound HTL-1 was synthesized according to the method described in International Publication No. 2015/145871 using Compound M1, Compound M2, and Compound M3. The number average molecular weight and weight average molecular weight in terms of polystyrene of the polymer compound HTL-1 were Mn = 2.3 × 10 ⁴ and Mw = 1.2 × 10 ⁵ , respectively.
The theoretical value obtained from the amount of the raw material used for the polymer compound HTL-1 is that the structural unit derived from the compound M1, the structural unit derived from the compound M2, and the structural unit derived from the compound M3 are: It is a copolymer constituted by a molar ratio of 45: 5: 50.

<Synthesis Example EML1> Synthesis of Polymer Compound EML-1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound M4 (2.52 g), Compound M2 (0.470 g), Compound M5 (4. 90 g), metal complex RM1 (0.530 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (4.2 mg) and toluene (158 mL) were added and heated to 100 ° C.
(Step 2) A 20% by mass tetraethylammonium hydroxide aqueous solution (16 mL) was added dropwise to the reaction solution and refluxed for 8 hours.
(Step 3) After the reaction, phenylboronic acid (116 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (4.2 mg) were added thereto and refluxed for 15 hours.
(Step 4) Thereafter, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 85 ° C. for 2 hours. After cooling, the reaction solution was washed with 3.6% by mass hydrochloric acid, 2.5% by mass ammonia water and water, and when the resulting solution was added dropwise to methanol, precipitation occurred. The precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 6.02 g of a polymer compound EML-1. The Mn of the polymer compound EML-1 was 3.8 × 10 ⁴ , and the Mw was 4.5 × 10 ⁵ .

  The high molecular compound EML-1 has a theoretical value obtained from the amount of raw materials charged, a structural unit derived from the compound M4, a structural unit derived from the compound M2, a structural unit derived from the compound M5, and a metal. The constitutional unit derived from the complex RM1 is a copolymer composed of a molar ratio of 40: 10: 47: 3.

<Synthesis Example ET1> Synthesis of Polymer Compound ET1 (Synthesis of Polymer Compound ET1a)
The polymer compound ET1a is obtained by using a compound ET1-1 synthesized according to the method described in JP2012-33845A and a compound ET1-2 synthesized according to the method described in JP2012-33845A. It was synthesized according to the method described in Kai 2012-33845.

The Mn of the polymer compound ET1a was 5.2 × 10 ⁴ .

  The polymer compound ET1a is composed of a structural unit derived from the compound ET1-1 and a structural unit derived from the compound ET1-2 in a molar ratio of 50:50 according to the theoretical value obtained from the amount of the raw materials. Copolymer.

(Synthesis of polymer compound ET1)
After making the inside of reaction container into inert gas atmosphere, the high molecular compound ET1a (200 mg), tetrahydrofuran (20 mL), and ethanol (20 mL) were added, and it heated at 55 degreeC. Thereafter, cesium hydroxide (200 mg) dissolved in water (2 mL) was added thereto, and the mixture was stirred at 55 ° C. for 6 hours. Then, after cooling to room temperature, solid was obtained by concentrating under reduced pressure. The obtained solid was washed with water and then dried under reduced pressure to obtain a polymer compound ET1 (150 mg, light yellow solid). From the NMR spectrum of the resulting polymer compound ET1, it was confirmed that the signal derived from the ethyl group at the ethyl ester site of the polymer compound ET1a had completely disappeared.

<Synthesis Example B1> Synthesis of Metal Complex B1 Metal complex B1 was synthesized by the following method.

(Synthesis of Compound L1-3)
After making the inside of reaction container nitrogen atmosphere, compound L1-1 (100g) and tetrahydrofuran (1L) were added and it cooled at 0 degreeC. To this, triethylamine (54 mL) was slowly added and stirred at 0 ° C. for 10 minutes. The compound L1-2 was dripped there, Then, it stirred at room temperature for 16 hours. The obtained reaction solution was concentrated under reduced pressure, and then ion-exchanged water was added and stirred for 1 hour to produce a solid. The obtained solid was collected by filtration, further washed with ethyl acetate, and dried under reduced pressure to obtain compound L1-3 (110 g). The HPLC area percentage value of Compound L1-3 was 99.5% or more.

The analysis results of Compound L1-3 were as follows.
¹ H-NMR (400 MHz, DMSO-d ₆ ): δ (ppm) = 1.03 (s, 9H), 2.07 (s, 2H), 7.48-7.60 (m, 3H), 7 .87-7.89 (m, 2H), 9.74 (s, 1H), 10.26 (s, 1H).

(Synthesis of Compound L1-5)
After making the inside of reaction container nitrogen atmosphere, compound L1-3 (40g) and xylene (400mL) were added and it was made 0 degreeC. The compound L1-4 (36.3g) was added there, and it stirred at 0 degreeC for 10 minutes. Thereto was added phosphorus pentachloride (53.3 g) dropwise, followed by stirring at 130 ° C. for 5 days. Then, the obtained reaction liquid was cooled to room temperature and concentrated under reduced pressure. The resulting reaction mixture was extracted with ethyl acetate and saturated aqueous sodium bicarbonate. The obtained organic layer was washed successively with water and saturated brine. Thereafter, the obtained organic layer was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was successively purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate) and reverse phase column chromatography (mixed solvent of water and acetonitrile), and further dried under reduced pressure to give compound L1- 5 (8 g) was obtained. The HPLC area percentage value of Compound L1-5 was 99.5%.

The analysis results of Compound L1-5 were as follows.
LC-MS (APCI, positive): m / z = 376 [M + H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 1.09 (s, 9H), 1.36 (s, 9H), 1.90 (s, 6H), 2.35 (s, 2H) ), 7.17 (s, 2H), 7.22-7.31 (m, 3H), 7.37-7.39 (m, 2H).

(Synthesis of metal complex B1)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (1.5 g), compound L1-5 (5.8 g) and pentadecane (2 mL) were added, and the mixture was stirred at 300 ° C. for 22 hours. . Thereafter, the obtained reaction solution was cooled to room temperature, and toluene was added thereto for dissolution, followed by concentration under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of heptane and ethyl acetate), further crystallized using a mixed solvent of toluene and heptane, and then dried under reduced pressure to obtain a metal complex. B1 (1.8 g) was obtained. The HPLC area percentage value of the metal complex B1 was 99.5% or more.

The analysis result of the metal complex B1 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 7.33 (s, 6H), 6.91-6.94 (m, 3H), 6.50 (td, 3H), 6 .30-6.34 (m, 3H), 6.09-6.12 (m, 3H), 2.21-2.25 (m, 3H), 2.13-2.16 (m, 3H) , 2.09 (s, 9H), 1.86 (s, 9H), 1.36-1.42 (m, 27H), 1.00-1.04 (m, 27H).

<Synthesis Example B2> Synthesis of Metal Complex B2 Metal complex B2 was synthesized by the following method.

(Synthesis of Compound L2-2)
After making the inside of reaction container nitrogen atmosphere, compound L1-1 (500g), tetrahydrofuran (5L), and triethylamine (585mL) were added, and it stirred at 0 degreeC. The compound L2-1 was dripped there, Then, it stirred at room temperature for 16 hours. After filtering the obtained reaction liquid, the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was washed with ethyl acetate and then dried under reduced pressure to obtain Compound L2-2 (500 g). The HPLC area percentage value of Compound L2-2 was 99.4%.

The analysis result of the compound L2-2 was as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 1.22 (d, 6H), 2.54-2.63 (m, 1H), 7.40-7.56 (m, 3H) 7.80-7.83 (m, 2H), 9.06 (s, 1H), 9.42 (s, 1H).

(Synthesis of Compound L2-3)
After making the inside of reaction container nitrogen atmosphere, compound L2-2 (40g), dichlorobenzene (400mL) and compound L1-4 (85g) were added, and it stirred at -10 degreeC. Thereto, phosphorus pentachloride (22 mL) was added dropwise. Then, it stirred at -10 degreeC for 30 minutes, and also after stirring at room temperature for 1 hour, it stirred at 185 degreeC for 18 hours. Then, the obtained reaction liquid was cooled to room temperature and concentrated under reduced pressure. The resulting reaction mixture was extracted with methylene chloride and ion exchange water. The obtained organic layer was dried over magnesium sulfate and filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mixed solvent of heptane and ethyl acetate), further crystallized using acetonitrile, and then dried under reduced pressure to give compound L2-3 (10 g). Got. The HPLC area percentage value of Compound L2-3 was 99.4%.

The analysis result of the compound L2-3 was as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 1.32 (d, 6H), 1.35 (s, 9H), 1.94 (s, 6H), 2.55-2.62 (M, 1H), 7.17 (s, 2H), 7.22-7.33 (m, 3H), 7.39-7.41 (m, 2H).

(Synthesis of metal complex B2)
The reaction vessel was filled with a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (3.5 g), compound L2-3 (10 g) and pentadecane (2 mL) were added, and the mixture was stirred at 285 ° C. for 18 hours. Thereafter, the obtained reaction solution was cooled to room temperature and purified by silica gel column chromatography (mixed solvent of heptane and ethyl acetate) and silica gel column chromatography (mixed solvent of methylene chloride and ethyl acetate), and further, heptane and toluene Crystallization was performed using a mixed solvent of Then, metal complex B2 (1.2g) was obtained by drying the obtained solid under reduced pressure. The HPLC area percentage value of the metal complex B2 was 99.5% or more. The required amount of metal complex B2 was obtained by repeating the above operation.

The analysis result of the metal complex B2 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 7.35 (brs, 3H), 7.34 (brs, 3H), 6.86 (dd, 3H), 6.49 (td) , 3H), 6.33 (td, 3H), 6.13 (d, 3H), 2.53 (spt, 3H), 2.15 (s, 9H), 1.90 (s, 9H), 1 .39 (s, 27H), 1.23 (d, 9H), 1.11 (d, 9H).

<Synthesis Example B3> Synthesis of Metal Complex B3 Metal complex B3 was synthesized by the following method.

(Synthesis of Compound L3-2)
After making the inside of reaction container nitrogen atmosphere, compound L1-1 (50g) and N-methyl-2-pyrrolidone (200mL) were added, and it stirred at 0 degreeC. The compound L3-1 (40g) dissolved in N-methyl-2-pyrrolidone (40mL) was dripped there, Then, it stirred at room temperature for 18 hours. Then, the precipitate was obtained by pouring the obtained reaction liquid into ion-exchange water (1.2L). The resulting precipitate was collected by filtration and further washed successively with 1M aqueous hydrochloric acid solution, ion-exchanged water and heptane. Then, the obtained solid was dried under reduced pressure to obtain Compound L3-2 (43 g, white solid).

The analysis result of the compound L3-2 was as follows.
¹ H-NMR (600 MHz, CDCl ₃ ) δ (ppm) = 9.64 (br, 1H), 8.90 (br, 1H), 7.86 (d, 2H), 7.56 (t, 1H) 7.45 (t, 2H), 7.02-7.08 (m, 3H), 2.41 (s, 6H).

(Synthesis of Compound L3-3)
After making the inside of reaction container nitrogen atmosphere, compound L3-2 (43g) and toluene (740mL) were added, and it stirred at room temperature. Thereto was added phosphorus pentachloride (67 g) little by little, and the mixture was stirred at 110 ° C. for 21 hours. The obtained reaction solution was cooled to room temperature, poured into ice water (500 mL), stirred for 2 hours, and the aqueous layer was removed. The obtained organic layer was washed with ion-exchanged water and a 10% by mass aqueous sodium hydrogen carbonate solution, and the obtained organic layer was dried over magnesium sulfate and then filtered. The obtained filtrate was concentrated under reduced pressure to obtain Compound L3-3 (40 g).

(Synthesis of Compound L3-5)
After making the inside of reaction container nitrogen atmosphere, compound L3-3 (40g), compound L3-4 (32g), and xylene (800mL) were added, and it stirred at room temperature. The p-toluenesulfonic acid (3g) was added there, and it stirred at 120 degreeC for 116 hours. Then, after cooling the obtained reaction liquid to room temperature, ion-exchange water (800 mL) was added there, and it stirred at room temperature for 1 hour. Thereafter, the aqueous layer was removed, and then the obtained organic layer was washed with a 5% by mass aqueous sodium hydrogen carbonate solution. The obtained organic layer was dried over magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified successively by silica gel column chromatography (mixed solvent of heptane and ethyl acetate) and silica gel column chromatography (acetonitrile and tetrahydrofuran) to give compound L3-5 (1.3 g, white solid). Obtained. The HPLC area percentage value of Compound L3-5 was 99.5% or more. The required amount of compound L3-5 was obtained by repeating the above operation.

The analysis result of Compound L3-5 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ) δ (ppm) = 7.42 (d, 2H), 7.30 (t, 1H), 7.24 (t, 2H), 7.15 (t, 1H), 6.98 (d, 2H), 6.85 (s, 2H), 2.51 (t, 2H), 2.07 (s, 6H), 1.81 (s, 6H), 1. 56 (m, 2H), 1.26-1.32 (m, 6H), 0.88 (t, 3H).

(Synthesis of metal complex B3)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (0.6 g), compound L3-5 (2.0 g) and tridecane (2 mL) were added, and the mixture was stirred at 250 ° C. for 120 hours. . Then, after cooling the obtained reaction liquid to room temperature, it refine | purified by silica gel column chromatography (the mixed solvent of heptane and ethyl acetate), and also crystallized using the mixed solvent of methylene chloride and acetonitrile. The obtained solid was dried under reduced pressure to obtain Metal Complex B3 (0.6 g, yellow solid). The HPLC area percentage value of the metal complex B3 was 99.2%.

The analysis result of the metal complex B3 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ) δ (ppm) = 7.04-7.08 (m, 6H), 6.93 (s, 3H), 6.92 (s, 3H), 6. 88 (d, 3H), 6.84 (d, 3H), 6.61 (t, 3H), 6.43 (t, 3H), 6.29 (d, 3H), 2.57 (t, 6H) ), 2.12 (s, 9H), 1.95 (s, 9H), 1.82 (s, 9H), 1.70 (s, 9H), 1.62 (m, 6H), 1.28 -1.36 (m, 18H), 0.89 (t, 9H).

<Synthesis Example B4> Synthesis of Metal Complex B4 Metal complex B4 was synthesized by the following method.

(Synthesis of Compound L4-2)
After making the inside of reaction container nitrogen atmosphere, compound L1-1 (100g), triethylamine (114mL), and tetrahydrofuran (1.5L) were added, and it stirred at 0 degreeC. The compound L4-1 (52 mL) was dripped there, Then, it stirred at room temperature for 16 hours. Then, after filtering the obtained reaction liquid, the crude product was obtained by concentrating the obtained filtrate. The obtained crude product was crystallized using ethyl acetate and then dried under reduced pressure to obtain Compound L4-2 (70 g). The HPLC area percentage value of Compound L4-2 was 98.7%.

The analysis result of the compound L4-2 was as follows.
LC-MS (APCI, positive): m / z = 179 [M + H] ^+
1 H-NMR (300 MHz, DMSO-d ₆ ) δ (ppm) = 10.26 (br, 1H), 9.86 (br, 1H), 7.83-7.86 (m, 2H), 7. 45-7.56 (m, 3H), 1.90 (s, 3H).

(Synthesis of Compound L4-4)
After making the inside of reaction container nitrogen atmosphere, compound L4-2 (70g) and xylene (700mL) were added and it stirred at room temperature. Thereto was added phosphorus pentachloride (123 g) little by little, and the mixture was stirred at 130 ° C. for 2 hours, and then cooled to room temperature. Thereto, Compound L4-3 (70 g) was added little by little and then stirred at 130 ° C. for 8 hours. Thereafter, the resulting reaction solution was cooled to room temperature and then concentrated under reduced pressure. Thereto, ethyl acetate was added, and the obtained organic layer was washed successively with ion-exchanged water, a 10% by mass aqueous sodium hydrogen carbonate solution and saturated brine. The obtained organic layer was dried over sodium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate), and further crystallized using a mixed solvent of N, N-dimethylformamide and water. The obtained solid was dried under reduced pressure to obtain Compound L4-4 (70 g, white solid). The HPLC area percentage value of Compound L4-4 was 99.2%.

The analysis result of Compound L4-4 was as follows.
LC-MS (APCI, positive): m / z = 320 [M + H] ^+
1 H-NMR (400 MHz, CDCl ₃ ) δ (ppm) = 7.53-7.58 (m, 1H), 7.48 (d, 2H), 7.33 (d, 2H), 7.28- 7.30 (m, 1H), 7.21-7.25 (m, 2H), 2.39 (q, 2H), 2.26 (s, 3H), 1.14 (d, 6H), 0 .87 (d, 6H).

(Synthesis of metal complex B4)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (1.2 g), compound L4-4 (4.0 g) and tridecane (1 mL) were added, and the mixture was stirred at 280 ° C. for 18 hours. . Then, after cooling the obtained reaction liquid to room temperature, it refine | purified by silica gel column chromatography (the mixed solvent of ethyl acetate and methanol), and also crystallized using the mixed solvent of toluene and acetonitrile. The obtained solid was dried under reduced pressure to obtain metal complex B4 (1.7 g, yellow solid). The HPLC area percentage value of the metal complex B4 was 99.5% or more.

The analysis result of metal complex B4 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ) δ (ppm) = 7.56 (t, 3H), 7.42 (dd, 3H), 7.40 (dd, 3H), 6.87 (dd, 3H), 6.52 (td, 3H), 6.35 (td, 3H), 6.17 (dd, 3H), 2.83 (hept, 3H), 2.34 (hept, 3H), 2. 10 (s, 9H), 1.23 (d, 9H), 0.98 (d, 9H), 0.96 (d, 9H), 0.92 (d, 9H).

<Synthesis Example B5> Synthesis of Metal Complex B5 Metal Complex B5 was synthesized by the following method.

(Synthesis of Compound L5-2)
After making the inside of reaction container nitrogen atmosphere, compound L1-1 (200 g), triethylamine (225 mL) and tetrahydrofuran (3 L) were added, and it cooled at 0 degreeC. The compound L5-1 (198g) was dripped there, Then, it stirred at room temperature for 16 hours. After filtering the obtained reaction liquid, the crude product was obtained by concentrating the obtained filtrate under reduced pressure. The obtained crude product was washed with ethyl acetate and then dried under reduced pressure to obtain Compound L5-2 (172 g). The HPLC area percentage value of Compound L5-2 was 99.2%.

The analysis result of Compound L5-2 was as follows.
¹ H-NMR (400 MHz, DMSO-d ₆ ): δ (ppm) = 0.88 (t, 3H), 1.18 (s, 6H), 1.57 (q, 2H), 7.47-7 .58 (m, 3H), 7.89-7.91 (m, 2H), 9.51 (s, 1H), 10.20 (s, 1H).

(Synthesis of Compound L5-3)
After making the inside of reaction container nitrogen atmosphere, compound L5-2 (100g) and toluene (700mL) were added and it stirred at room temperature. Thereto was added phosphorus pentachloride (178 g) little by little, and the mixture was stirred at 110 ° C. for 18 hours, and then cooled to room temperature. The obtained reaction solution was concentrated to obtain a crude product L5-2 ′ (65 g). Then, after making the inside of reaction container again nitrogen atmosphere, toluene (1L), compound L1-4 (43g), and p-toluenesulfonic acid (6.5g) were added, and it stirred at 110 for 3 days. Thereafter, the resulting reaction solution was cooled to room temperature and then concentrated under reduced pressure. Thereto was added ethyl acetate, and the resulting organic layer was washed with ion-exchanged water. The obtained organic layer was dried over sodium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate), and further crystallized using a mixed solvent of acetonitrile and ethyl acetate. The obtained solid was purified by reverse phase column chromatography and then dried under reduced pressure to obtain Compound L5-3 (16 g). The HPLC area percentage value of Compound L5-3 was 99.4%.

The analysis result of Compound L5-3 was as follows.
LC-MS (APCI, positive): m / z = 376 [M + H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 0.89 (t, 3H), 1.19 (s, 6H), 1.33 (s, 9H), 1.71 (q, 2H) ), 1.97 (s, 6H), 7.12 (s, 2H), 7.19-7.23 (m, 2H), 7.27-7.28 (m, 1H), 7.33- 7.36 (m, 2H).

(Synthesis of metal complex B5)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (1.5 g), compound L5-3 (4.0 g) and tridecane (2 mL) were added, and the mixture was stirred at 280 ° C. for 28 hours. . Then, after cooling the obtained reaction liquid to room temperature, it refine | purified by silica gel column chromatography (a mixed solvent of heptane and ethyl acetate), and also crystallized using the mixed solvent of toluene and methanol. The obtained solid was dried under reduced pressure to obtain metal complex B5 (1.0 g, yellow solid). The HPLC area percentage value of the metal complex B5 was 99.5% or more.

The analysis result of the metal complex B5 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 7.31 (s, 6H), 6.91 (d, 3H), 6.48 (td, 3H), 6.24-6 .30 (m, 3H), 5.87 (d, 3H), 2.12-2.15 (m, 9H), 1.94 (s, 9H), 1.58-1.66 (m, 3H) ), 1.50-1.57 (m, 3H), 1.38 (s, 27H), 1.12-1.16 (m, 9H), 1.04-1.08 (m, 9H), 0.84 (t, 9H).

<Synthesis Example B6> Synthesis of Metal Complex B6 Metal Complex B6 was synthesized by the following method.

(Synthesis of reaction mixture L6-1 ′)
After making the inside of reaction container nitrogen atmosphere, compound L6-1 (50g) and thionyl chloride (100mL) were added, and it stirred under recirculation | reflux for 3 hours. Thereafter, the reaction mixture was cooled to room temperature, and then thionyl chloride was distilled off under reduced pressure to obtain a reaction mixture L6-1 ′.

(Synthesis of Compound L6-2)
After making the inside of reaction container nitrogen atmosphere, compound L1-1 (47g) and tetrahydrofuran (1L) were added and it cooled at 0 degreeC. To this, triethylamine (54 mL) was slowly added and stirred at 0 ° C. for 45 minutes. Thereto, the reaction mixture L6-1 ′ (total amount) obtained in (Synthesis of the reaction mixture L6-1 ′) was slowly added. Then, it stirred at room temperature for 16 hours. After filtering the obtained reaction liquid, the crude product was obtained by concentrating the obtained filtrate under reduced pressure. The obtained crude product was washed with a mixed solvent of ethyl acetate and hexane, and then dried under reduced pressure to obtain Compound L6-2 (50 g). The HPLC area percentage value of Compound L6-2 was 95.2%. The required amount of compound L6-2 was obtained by repeating the above operation.

The analysis result of Compound L6-2 was as follows.
LC-MS (APCI, positive): m / z = 263 [M + H] ^+
1 H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 0.84 (t, 9H), 1.64 (q, 6H), 7.39-7.54 (m, 3H), 7.81 -7.84 (m, 2H), 8.72-8.74 (m, 1H), 9.66-9.68 (m, 1H).

(Synthesis of Compound L6-3)
After making the inside of reaction container nitrogen atmosphere, compound L6-2 (58g) and toluene (600mL) were added, and it stirred at room temperature. Thereto was slowly added phosphorus pentachloride (92 g), and the mixture was stirred at 110 ° C. for 3 hours. Then, the obtained reaction liquid was cooled to room temperature, and compound L1-4 (78.2 g) and p-toluenesulfonic acid (3 g) were added thereto. Then, after stirring at 130 ° C. for 4 days, the reaction solution was cooled to room temperature. The obtained reaction solution was concentrated under reduced pressure, ethyl acetate (2 L) was added thereto, and then washed with a 10 mass% aqueous sodium hydrogen carbonate solution. The obtained organic layer was dried over magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (mixed solvent of methanol and chloroform), further crystallized using acetonitrile, and then dried under reduced pressure to obtain Compound L6-3 (6 g). . The HPLC area percentage value of Compound L6-3 was 99.1%.

The analysis result of Compound L6-3 was as follows.
LC-MS (APCI, positive): m / z = 404 [M + H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 0.83 (t, 9H), 1.34 (s, 9H), 1.64 (q, 6H), 1.96 (s, 6H) ), 7.12 (s, 2H), 7.20-7.23 (m, 2H), 7.28-7.34 (m, 3H).

(Synthesis of metal complex B6)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (1.4 g), compound L6-3 (4.6 g) and pentadecane (2 mL) were added, and the mixture was stirred at 300 ° C. for 18 hours. . Thereafter, the obtained reaction solution was cooled to room temperature, and toluene was added thereto for dissolution, followed by concentration under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (mixed solvent of heptane and ethyl acetate), further crystallized using a mixed solvent of acetonitrile and toluene, and then dried under reduced pressure to obtain a metal complex. B6 (2.8 g) was obtained. The HPLC area percentage value of the metal complex B6 was 99.5% or more.

The analysis result of the metal complex B6 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 7.30 (s, 6H), 6.90 (d, 3H), 6.44-6.48 (m, 3H), 6 .22-6.26 (m, 3H), 5.77 (d, 3H), 2.10 (s, 9H), 1.89 (s, 9H), 1.56 (s, 18H), 1. 38 (s, 27H), 0.73 (t, 27H).

<Synthesis Example B7> Synthesis of Metal Complex B7 Metal complex B7 was synthesized by the following method.

(Synthesis of metal complex B7 ′)
After making the inside of reaction container nitrogen atmosphere, metal complex B2 (2.2g) and methylene chloride (30mL) were added, and it stirred at 0 degreeC. Thereto, N-bromosuccinimide (0.95 g) was slowly added over 15 minutes, and then the reaction solution was slowly heated from 0 ° C. to room temperature, and further stirred at room temperature for 20 hours. Then, after adding methanol (100 mL) there, the precipitate was obtained by stirring for 15 minutes. The obtained precipitate was collected by filtration, further washed with methanol, and then dried under reduced pressure to obtain metal complex B7 ′ (2.1 g). The HPLC area percentage value of the metal complex B7 ′ was 99.3%.

The analysis result of metal complex B7 ′ was as follows.
LC-MS (APCI, positive): m / z = 1468 [M + H] ⁺

(Synthesis of metal complex B7)
After making the inside of reaction container nitrogen atmosphere, metal complex B7 ′ (1.0 g), compound L7-1 (1.2 g), toluene (50 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd ₂ ( dba) ₃ ) (9.4 mg) and 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) (8.4 mg) were added, and the temperature was raised to 80 ° C. Then, 20 mass% tetraethylammonium hydroxide aqueous solution (1.8 mL) was added there, and it stirred under heating-refluxing for 20 hours. Thereafter, the obtained reaction solution was cooled to room temperature, the aqueous layer was removed, and the obtained organic layer was filtered with a filter covered with silica gel. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of methylene chloride and ethyl acetate), further crystallized using a mixed solvent of acetonitrile and toluene, and then dried under reduced pressure to obtain metal complex B7. (0.72 g) was obtained. The HPLC area percentage value of the metal complex B7 was 99.5% or more.

The analysis result of the metal complex B7 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 7.57-7.61 (m, 15H), 7.49 (d, 12H), 7.43 (d, 6H), 7 .27 (d, 3H), 7.23 (d, 3H), 7.21 (d, 3H), 7.09 (dd, 3H), 6.65 (d, 3H), 2.61 (spt, 3H), 2.24 (s, 9H), 2.08 (s, 9H), 1.38 (s, 54H), 1.28 (d, 9H), 1.18 (d, 9H), 0. 93 (s, 27H).

<Synthesis Example B8> Synthesis of Metal Complex B8 Metal Complex B8 was synthesized by the following method.

(Synthesis of Compound L8-1)
After making the inside of reaction container nitrogen atmosphere, compound L1-4 (200 g), triethylamine (472 mL) and tetrahydrofuran (2 L) were added, and it cooled to 0 degreeC. Thereto, Compound L5-1 (228 g) was slowly added dropwise, followed by stirring at room temperature for 16 hours. After filtering the obtained reaction liquid, the crude product was obtained by concentrating the obtained filtrate under reduced pressure. The obtained crude product was washed with ethyl acetate and then dried under reduced pressure to obtain Compound L8-1 (205 g). The HPLC area percentage value of Compound L8-1 was 99.5% or more.

The analysis result of Compound L8-1 was as follows.
LC-MS (APPI, positive): m / z = 276 [M + H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 1.01 (t, 3H), 1.31 (s, 6H), 1.33 (s, 9H), 1.70 (q, 2H) ), 2.23 (s, 6H), 6.84-7.09 (m, 3H).

(Synthesis of Compound L8-3)
After making the inside of reaction container nitrogen atmosphere, compound L8-1 (115 g), monochlorobenzene (1.2 L), 2-fluoropyridine (44.6 g) and trifluoromethanesulfonic anhydride (130 g) were added, and at room temperature. Stir. The compound L8-2 (23g) was added there, and it stirred at room temperature for 1 hour, Then, it stirred at 90 degreeC for 18 hours. Then, the obtained reaction liquid was cooled to room temperature, and chloroform was added there. The obtained reaction liquid was washed with a 10% by mass aqueous sodium hydrogen carbonate solution, and further washed twice with ion-exchanged water. The obtained organic layer was dried over magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate), further crystallized using acetonitrile, and then dried under reduced pressure to give compound L8-3 (100 g). Got. The HPLC area percentage value of Compound L8-3 was 99.5% or more.

The analysis result of the compound L8-3 was as follows.
LC-MS (APCI, positive): m / z = 454 [M + H] ^+
1 H-NMR (400 MHz, DMSO-d ₆ ): δ (ppm) = 0.79 (t, 3H), 1.12 (s, 6H), 1.31 (s, 9H), 1.62 (q , 2H), 1.91 (s, 6H), 7.16 (s, 2H), 7.27-7.39 (m, 3H), 7.56 (d, 1H).

(Synthesis of Compound L8-5)
After making the inside of reaction container nitrogen atmosphere, compound L8-3 (50 g), compound L8-4 (22 g), toluene (500 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd ₂ (dba) ₃ ) (1 g), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) (0.9 g) was added, and the temperature was raised to 60 ° C. 25 mass% tetraethylammonium hydroxide aqueous solution (260 mL) was added there, and it stirred under heating-refluxing for 18 hours. Then, after filtering the obtained reaction liquid with the filter which spread celite, celite was wash | cleaned with ethyl acetate. After removing the aqueous layer from the obtained filtrate, the obtained organic layer was washed with ion-exchanged water. The obtained organic layer was dried over magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (a mixed solvent of hexane and ethyl acetate), further crystallized using acetonitrile, and then dried under reduced pressure to give compound L8-5 (36 g). Got. Compound L8-5 had an HPLC area percentage value of 99.5% or more.

The analysis result of Compound L8-5 was as follows.
LC-MS (APCI, positive): m / z = 508 [M + H] ^+
1 H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 0.92 (t, 3H), 1.23 (s, 6H), 1.35 (s, 9H), 1.37 (s, 9H) ), 1.73 (q, 2H), 2.01 (s, 6H), 7.19 (d, 2H), 7.20 (s, 2H), 7.26-7.28 (m, 1H) , 7.34-7.39 (m, 3H), 7.51-7.54 (m, 1H), 7.69-7.72 (m, 1H).

(Synthesis of metal complex B8)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (2.1 g), compound L8-5 (8.6 g) and pentadecane (3 mL) were added, and the mixture was stirred at 300 ° C. for 24 hours. . Then, solid was deposited by cooling a reaction liquid to room temperature. The precipitated solid was collected by filtration, and the obtained solid was purified by silica gel column chromatography (mixed solvent of methylene chloride and ethyl acetate). Further, after crystallization using a mixed solvent of acetonitrile and methylene chloride, By drying under reduced pressure, metal complex B8 (4.0 g) was obtained. The HPLC area percentage value of the metal complex B8 was 99.5% or more.

The analysis result of the metal complex B8 was as follows.
LC-MS (ESI, positive): m / z = 1713 [M + H] ^+
1 H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 0.92 (t, 9H), 1.11 (s, 9H), 1.22 (s, 9H), 1.27 (s 27H), 1.42 (s, 27H), 1.56-1.62 (m, 3H), 1.64-1.72 (m, 3H), 2.02 (s, 9H), 2. 18 (s, 9H), 6.24 (d, 3H), 6.92 (dd, 3H), 7.04 (d, 6H), 7.15 (d, 3H), 7.19 (d, 6H) ), 7.38 (d, 6H).

<Synthesis Example B9> Synthesis of Metal Complex B9 Metal Complex B9 was synthesized by the following method.

(Synthesis of Compound L9-1)
After making the inside of reaction container nitrogen atmosphere, 4-bromo-2,6-dimethylaniline (100 g), triethylamine (253 mL) and tetrahydrofuran (1.5 L) were added, and it cooled to 0 degreeC. Compound L5-1 (124 mL) was slowly added dropwise thereto, and the mixture was stirred at room temperature for 16 hours. After filtering the obtained reaction liquid, the crude product was obtained by concentrating the obtained filtrate under reduced pressure. The obtained crude product was crystallized using acetonitrile, and then dried under reduced pressure to obtain Compound L9-1 (125 g). The HPLC area percentage value of Compound L9-1 was 98.7%.

The analysis result of the compound L9-1 was as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 0.96 (t, 3H), 1.29 (s, 6H), 1.68 (q, 2H), 2.16 (s, 6H) ), 6.93 (brs, 1H), 7.08 (s, 2H).

(Synthesis of Compound L9-2)
After making the inside of reaction container nitrogen atmosphere, compound L9-1 (120 g), monochlorobenzene (1.2 L), 2-fluoropyridine (43 g) and trifluoromethanesulfonic anhydride (125 g) were added and stirred at room temperature. . The compound L8-2 (95.2g) was added there, and it stirred at room temperature for 1 hour, Then, it stirred at 90 degreeC for 18 hours, and also stirred at 130 degreeC for 12 hours. Then, the obtained reaction liquid was cooled to room temperature, and ethyl acetate was added there. The obtained reaction liquid was washed with a 10% by mass aqueous sodium hydrogen carbonate solution, and further washed twice with ion-exchanged water. The obtained organic layer was dried over magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was crystallized using acetonitrile and then dried under reduced pressure to obtain Compound L9-2 (70 g). The HPLC area percentage value of Compound L9-2 was 99.5% or more.

The analysis result of the compound L9-2 was as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 0.89 (t, 3H), 1.22 (s, 6H), 1.71 (q, 2H), 1.99 (s, 6H) ), 7.11-7.14 (m, 2H), 7.37 (s, 2H), 7.46-7.49 (m, 1H), 7.64-7.65 (m, 1H).

(Synthesis of Compound L9-3)
After making the inside of reaction container nitrogen atmosphere, compound L9-2 (60 g), phenylboronic acid (38.3 g), toluene (600 mL), tris (dibenzylideneacetone) dipalladium (0) (Pd ₂ (dba) ₃ ) (2.3 g) and 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) (2.1 g) were added, and the temperature was raised to 60 ° C. 25 mass% tetraethylammonium hydroxide aqueous solution (300 mL) was added there, and it stirred under heating-refluxing for 18 hours. Then, after filtering the obtained reaction liquid with the filter which spread celite, celite was wash | cleaned with ethyl acetate. After removing the aqueous layer from the obtained filtrate, the obtained organic layer was washed with ion-exchanged water. The obtained organic layer was dried over magnesium sulfate and then filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a crude product. The obtained crude product was crystallized using acetonitrile, and further crystallized using a mixed solvent of acetonitrile and toluene. The obtained solid was successively purified by silica gel column chromatography (mixed solvent of hexane and ethyl acetate) and reverse phase column chromatography (mixed solvent of water and acetonitrile), and then dried under reduced pressure to give compound L9. -3 (34 g) was obtained. The HPLC area percentage value of Compound L9-3 was 99.5% or more.

The analysis result of the compound L9-3 was as follows.
¹ H-NMR (400 MHz, CDCl ₃ ): δ (ppm) = 0.95 (t, 3H), 1.29 (s, 6H), 1.79 (q, 2H), 2.01 (s, 6H) ), 7.26-7.31 (m, 5H), 7.36-7.57 (m, 8H), 7.65-7.69 (m, 3H).

(Synthesis of metal complex B9)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (1.3 g), compound L9-3 (5.0 g) and pentadecane (2 mL) were added, and the mixture was stirred at 300 ° C. for 24 hours. . Thereafter, the reaction solution was cooled to 50 ° C., and toluene was added thereto. Then, after cooling the obtained reaction liquid to room temperature, it wash | cleaned with ion-exchange water. The obtained organic layer was concentrated under reduced pressure to obtain a solid. The obtained solid was purified by silica gel column chromatography (mixed solvent of methylene chloride and ethyl acetate), further crystallized using a mixed solvent of acetonitrile and toluene, and then dried under reduced pressure to obtain metal complex B9. (0.65 g) was obtained. The HPLC area percentage value of the metal complex B9 was 99.5% or more.

The analysis result of the metal complex B9 was as follows.
¹ H-NMR (600 MHz, THF-d ₈ ): δ (ppm) = 7.77 (dd, 6H), 7.65 (s, 6H), 7.50 (t, 6H), 7.41 (tt 3H), 7.25 (d, 3H), 7.11 (dd, 6H), 6.98-7.02 (m, 9H), 6.93-6.97 (m, 3H), 6. 33 (d, 3H), 2.27 (s, 9H), 2.13 (s, 9H), 1.75-1.79 (m, 4H), 1.64-1.70 (m, 4H) , 1.30 (s, 9H), 1.22 (s, 9H), 1.00 (t, 9H).

<Synthesis and Acquisition of Metal Complexes G1-G3>
The metal complex G1 was purchased from Luminescience Technology.
The metal complex G2 was synthesized according to the method described in JP2013-237789A.
The metal complex G3 was synthesized according to the method described in International Publication No. 2009/131255.

<Synthesis and Acquisition of Metal Complexes R1 to R7>
The metal complex R1 was purchased from Luminescence Technology.
Metal complex R2 was purchased from American Dye Source.
The metal complex R3 was synthesized according to the method described in International Publication No. 2002/44189.
The metal complex R4 was synthesized according to the method described in JP-A-2006-188673.
Metal complex R5 was purchased from Luminescence Technology.
The metal complex R6 was synthesized according to the method described in JP2008-179617A.
Metal complex R7 was synthesized according to the method described in JP2011-105701A.

<Example D1> Fabrication and evaluation of light-emitting element D1 (Formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport 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 having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Compound HM-1, metal complex B1 and metal complex R3 (compound HM-1 / metal complex B1 / metal complex R3 = 74 mass% / 25 mass% / 1 mass%) are dissolved in toluene at a concentration of 2 mass%. It was. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. Compound HM-1 used was purchased from Luminescience Technology.

(Formation of electron transport layer)
The polymer compound ET1 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride was about 4 nm on the electron transport layer as a cathode, and then the sodium fluoride layer About 80 nm of aluminum was deposited thereon. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
By applying a voltage to the light emitting element D1, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 495 nm, and 625 nm was observed. Light emission at 470 nm and 495 nm was light emission derived from the metal complex B1, and light emission at 625 nm was light emission derived from the metal complex R3. The luminous efficiency at 50 cd / m ² was 7.5 [lm / W], and the chromaticity coordinates (x, y) were (0.55, 0.32).

<Example D2> Production and Evaluation of Light-Emitting Element D2 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74% by mass / 25% by mass / 1% by mass)”, “compound HM-1, metal complex B5 and metal complex R3 (compound HM-1 / metal complex B5 / metal complex R3 = 74% by mass / 25”) Except that “mass% / 1 mass%)” was used, a light emitting device D2 was fabricated in the same manner as in Example D1.

By applying a voltage to the light-emitting element D2, EL light emission having a maximum emission wavelength of an emission spectrum at 465 nm, 495 nm, and 625 nm was observed. The light emission at 465 nm and 495 nm was light emission derived from the metal complex B5, and the light emission at 625 nm was light emission derived from the metal complex R3. The light emission efficiency at 50 cd / m ² was 7.0 [lm / W], and the chromaticity coordinates (x, y) were (0.56, 0.32).

<Comparative Example CD1> Production and Evaluation of Light-Emitting Element CD1 “Compound HM-1, Metal Complex B1, and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3) in Example D1 (Formation of Light-Emitting Layer)” = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B1 and Metal Complex R1 (Compound HM-1 / Metal Complex B1 / Metal Complex R1) = 74 mass% / 25 The light emitting device CD1 was manufactured in the same manner as in Example D1 except that “mass% / 1 mass%)” was used.

By applying a voltage to the light emitting device CD1, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 495 nm, 620 nm and 675 nm was observed. The light emission at 465 nm and 495 nm was light emission derived from the metal complex B1, and the light emission at 620 nm and 675 nm was light emission derived from the metal complex R1. The light emission efficiency at 50 cd / m ² was 4.7 [lm / W], and the chromaticity coordinates (x, y) were (0.47, 0.33).

<Comparative Example CD2> Production and Evaluation of Light-Emitting Element CD2 “Compound HM-1, Metal Complex B1, and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3) in Example D1 (Formation of Light-Emitting Layer)” = “74% by mass / 25% by mass / 1% by mass)”, “compound HM-1, metal complex B3 and metal complex R3 (compound HM-1 / metal complex B3 / metal complex R3 = 74% by mass / 25”) The light emitting device CD2 was fabricated in the same manner as in Example D1 except that “mass% / 1 mass%)” was used.

By applying a voltage to the light emitting device CD2, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 500 nm, and 620 nm was observed. Light emission at 470 nm and 500 nm was light emission derived from the metal complex B3, and light emission at 620 nm was light emission derived from the metal complex R3. The luminous efficiency at 50 cd / m ² was 2.6 [lm / W], and the chromaticity coordinates (x, y) were (0.55, 0.32).

<Example D3> Production and Evaluation of Light-Emitting Element D3 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B1, Metal Complex G2 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex G2 / Metal) A light emitting device D3 was produced in the same manner as in Example D1, except that “complex R3 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D3, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 505 nm, and 620 nm was observed. These luminescences were luminescences derived from the metal complex B1, the metal complex G2, and the metal complex R3, respectively. The light emission efficiency at 100 cd / m ² was 19.7 [lm / W], and the chromaticity coordinates (x, y) were (0.30, 0.49).

<Example D4> Production and Evaluation of Light-Emitting Element D4 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B1, Metal Complex G3 and Metal Complex R4 (Compound HM-1 / Metal Complex B1 / Metal Complex G3 / Metal) A light emitting device D4 was produced in the same manner as in Example D1, except that “complex R4 = 73.9 mass% / 25 mass% / 1 mass% / 0.1 mass%)” was used.

By applying a voltage to the light emitting element D4, EL light emission having a maximum light emission wavelength of an emission spectrum at 465 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B1, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 15.7 [lm / W], and the chromaticity coordinates (x, y) were (0.28, 0.43).

<Example D5> Production and Evaluation of Light-Emitting Element D5 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = "74 mass% / 25 mass% / 1 mass%)" instead of "Compound HM-1, Metal Complex B2, Metal Complex G2 and Metal Complex R3 (Compound HM-1, Metal Complex B2 / Metal Complex G2 / Metal) A light emitting device D5 was produced in the same manner as in Example D1, except that “complex R3 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D5, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 505 nm, and 620 nm was observed. These luminescences were luminescences derived from the metal complex B2, the metal complex G2, and the metal complex R3, respectively. The luminous efficiency at 100 cd / m ² was 16.1 [lm / W], and the chromaticity coordinates (x, y) were (0.34, 0.47).

<Example D6> Production and Evaluation of Light-Emitting Element D6 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B2, metal complex G3 and metal complex R4 (compound HM-1 / metal complex B2 / metal complex G3 / metal) A light emitting device D6 was produced in the same manner as in Example D1, except that “complex R4 = 73.9 mass% / 25 mass% / 1 mass% / 0.1 mass%)” was used.

By applying a voltage to the light emitting element D6, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 510 nm and 620 nm was observed. These luminescences were luminescences derived from the metal complex B2, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 18.1 [lm / W], and the chromaticity coordinates (x, y) were (0.32, 0.47).

<Example D7> Production and Evaluation of Light-Emitting Element D7 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B5, metal complex G3 and metal complex R4 (compound HM-1 / metal complex B5 / metal complex G3 / metal) A light emitting device D7 was produced in the same manner as in Example D1, except that the complex R4 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass) was used.

By applying a voltage to the light emitting element D7, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 510 nm, and 620 nm was observed. These luminescences were luminescences derived from the metal complex B5, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 19.0 [lm / W], and the chromaticity coordinates (x, y) were (0.29, 0.47).

<Example D8> Production and Evaluation of Light-Emitting Element D8 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B6, metal complex G3 and metal complex R4 (compound HM-1 / metal complex B6 / metal complex G3 / metal) A light emitting device D8 was produced in the same manner as in Example D1, except that “complex R4 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D8, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 510 nm and 620 nm was observed. These luminescences were luminescences derived from the metal complex B6, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 16.5 [lm / W], and the chromaticity coordinates (x, y) were (0.29, 0.47).

<Example D9> Production and Evaluation of Light-Emitting Element D9 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B7, metal complex G2 and metal complex R5 (compound HM-1 / metal complex B7 / metal complex G2 / metal) A light emitting device D9 was produced in the same manner as in Example D1, except that “complex R5 = 73.9 mass% / 25 mass% / 1 mass% / 0.1 mass%)” was used.

By applying a voltage to the light emitting element D9, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B7, the metal complex G2, and the metal complex R5, respectively. The light emission efficiency at 100 cd / m ² was 43.2 [lm / W], and the chromaticity coordinates (x, y) were (0.27, 0.51).

<Example D10> Production and Evaluation of Light-Emitting Element D10 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B7, metal complex G3 and metal complex R4 (compound HM-1 / metal complex B7 / metal complex G3 / metal) A light emitting device D10 was produced in the same manner as in Example D1, except that “complex R4 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D10, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B7, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 35.9 [lm / W], and the chromaticity coordinates (x, y) were (0.28, 0.49).

<Example D11> Production and Evaluation of Light-Emitting Element D11 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B8, Metal Complex G2 and Metal Complex R5 (Compound HM-1 / Metal Complex B8 / Metal Complex G2 / Metal) A light emitting device D11 was produced in the same manner as in Example D1, except that “complex R5 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D11, EL light emission having a maximum emission wavelength of an emission spectrum at 480 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B8, the metal complex G2, and the metal complex R5, respectively. The light emission efficiency at 100 cd / m ² was 19.3 [lm / W], and the chromaticity coordinates (x, y) were (0.30, 0.51).

<Example D12> Production and Evaluation of Light-Emitting Element D12 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B8, metal complex G3 and metal complex R4 (compound HM-1 / metal complex B8 / metal complex G3 / metal) A light emitting device D12 was produced in the same manner as in Example D1, except that “complex R4 = 73.9 mass% / 25 mass% / 1 mass% / 0.1 mass%)” was used.

By applying a voltage to the light emitting element D12, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B8, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 18.1 [lm / W], and the chromaticity coordinates (x, y) were (0.31, 0.48).

<Example D13> Production and Evaluation of Light-Emitting Element D13 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B9, Metal Complex G2 and Metal Complex R5 (Compound HM-1 / Metal Complex B9 / Metal Complex G2 / Metal) A light emitting device D13 was produced in the same manner as in Example D1, except that “complex R5 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D13, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B9, the metal complex G2, and the metal complex R5, respectively. The light emission efficiency at 100 cd / m ² was 37.6 [lm / W], and the chromaticity coordinates (x, y) were (0.29, 0.51).

<Example D14> Production and Evaluation of Light-Emitting Element D14 "Compound HM-1, Metal Complex B1, and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B9, metal complex G3 and metal complex R4 (compound HM-1 / metal complex B9 / metal complex G3 / metal) A light emitting device D14 was produced in the same manner as in Example D1, except that “complex R4 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting element D14, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B9, the metal complex G3, and the metal complex R4, respectively. The light emission efficiency at 100 cd / m ² was 25.6 [lm / W], and the chromaticity coordinates (x, y) were (0.32, 0.49).

<Example D15> Production and Evaluation of Light-Emitting Element D15 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B8, Metal Complex G3 and Metal Complex R6 (Compound HM-1 / Metal Complex B8 / Metal Complex G3 / Metal) A light emitting device D15 was produced in the same manner as in Example D1, except that the complex R6 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass) was used.

By applying a voltage to the light emitting element D15, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 585 nm was observed. These luminescences were luminescences derived from the metal complex B8, the metal complex G3, and the metal complex R6, respectively. The light emission efficiency at 100 cd / m ² was 20.0 [lm / W], and the chromaticity coordinates (x, y) were (0.42, 0.46).

<Example D16> Production and Evaluation of Light-Emitting Element D16 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B8, Metal Complex G3 and Metal Complex R7 (Compound HM-1 / Metal Complex B8 / Metal Complex G3 / Metal) A light emitting device D16 was produced in the same manner as in Example D1, except that “complex R7 = 73.9 mass% / 25 mass% / 1 mass% / 0.1 mass%)” was used.

By applying a voltage to the light emitting element D16, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 605 nm was observed. These luminescences were luminescences derived from the metal complex B8, the metal complex G3, and the metal complex R7, respectively. The light emission efficiency at 100 cd / m ² was 15.9 [lm / W], and the chromaticity coordinates (x, y) were (0.37, 0.46).

<Comparative Example CD3> Preparation and Evaluation of Light-Emitting Element CD3 “Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3) in Example D1 (Formation of Light-Emitting Layer)” = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B2, Metal Complex G1 and Metal Complex R2 (Compound HM-1 / Metal Complex B2 / Metal Complex G1 / Metal) A light emitting device CD3 was produced in the same manner as in Example D1 except that “complex R2 = 73.9% by mass / 25% by mass / 1% by mass / 0.1% by mass)” was used.

By applying a voltage to the light emitting device CD3, EL light emission having a maximum emission wavelength of an emission spectrum at 470 nm, 505 nm, and 620 nm was observed. These luminescences were luminescences derived from the metal complex B2, the metal complex G1, and the metal complex R2, respectively. The light emission efficiency at 100 cd / m ² was 12.3 [lm / W], and the chromaticity coordinates (x, y) were (0.36, 0.45).

<Comparative Example CD4> Production and Evaluation of Light-Emitting Element CD4 "Compound HM-1, Metal Complex B1 and Metal Complex R3 (Compound HM-1 / Metal Complex B1 / Metal Complex R3" in Example D1 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B3, metal complex G2 and metal complex R3 (compound HM-1 / metal complex B3 / metal complex G2 / metal) A light emitting device CD4 was produced in the same manner as in Example D1 except that “complex R3 = 73.9 mass% / 25 mass% / 1 mass% / 0.1 mass%)” was used.

By applying a voltage to the light emitting device CD4, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 505 nm, and 615 nm was observed. These luminescences were luminescences derived from the metal complex B3, the metal complex G2, and the metal complex R3, respectively. The light emission efficiency at 100 cd / m ² was 8.0 [lm / W], and the chromaticity coordinates (x, y) were (0.31, 0.49).

<Example D17> Fabrication and evaluation of light-emitting element D17 (Formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of second light emitting layer)
The polymer compound EML-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm is formed on the hole injection layer by spin coating, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes to form a second film. The light emitting layer was formed.

(Formation of light emitting layer)
Compound HM-1, metal complex B5 and metal complex G3 (compound HM-1 / metal complex B5 / metal complex G3 = 74% by mass / 25% by mass / 1% by mass) are dissolved in toluene at a concentration of 2% by mass. It was. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the second light-emitting layer by spin coating, and the light-emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. .

(Formation of electron transport layer)
The polymer compound ET1 was dissolved in 2,2,3,3,4,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,4,5,5-octafluoro-1-pentanol solution, a film having a thickness of 10 nm was formed on the light emitting layer by spin coating, An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the electron transport layer was formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride was about 4 nm on the electron transport layer as a cathode, and then the sodium fluoride layer About 80 nm of aluminum was deposited thereon. After vapor deposition, the light emitting element D17 was produced by sealing using a glass substrate.

(Evaluation of light emitting element)
By applying a voltage to the light emitting element D17, EL light emission having a maximum light emission wavelength of an emission spectrum at 470 nm, 510 nm, and 595 nm was observed. These luminescences were luminescences derived from the metal complex B5, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 38.5 [lm / W], and the chromaticity coordinates (x, y) were (0.43, 0.43).

<Example D18> Production and Evaluation of Light-Emitting Element D18 "Compound HM-1, Metal Complex B5, and Metal Complex G3 (Compound HM-1 / Metal Complex B5 / Metal Complex G3) in Example D17 (Formation of Light-Emitting Layer)" = “74 mass% / 25 mass% / 1 mass%)” instead of “Compound HM-1, Metal Complex B2, and Metal Complex G3 (Compound HM-1, Metal Complex B2 / Metal Complex G3 = 74 mass% / 25 Except that “mass% / 1 mass%)” was used, a light emitting device D18 was fabricated in the same manner as in Example D17.

By applying a voltage to the light emitting element D18, EL light emission having a maximum light emission wavelength of an emission spectrum at 475 nm, 510 nm, and 595 nm was observed. These luminescences were luminescences derived from the metal complex B2, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 27.4 [lm / W], and the chromaticity coordinates (x, y) were (0.45, 0.43).

<Example D19> Production and Evaluation of Light-Emitting Element D19 "Compound HM-1, Metal Complex B5, and Metal Complex G3 (Compound HM-1 / Metal Complex B5 / Metal Complex G3" in Example D17 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B6 and metal complex G3 (compound HM-1 / metal complex B6 / metal complex G3 = 74 mass% / 25 Except that “mass% / 1 mass%)” was used, a light emitting device D19 was produced in the same manner as in Example D17.

By applying a voltage to the light emitting element D19, EL light emission having a maximum light emission wavelength of an emission spectrum at 465 nm, 510 nm, and 595 nm was observed. These luminescences were luminescences derived from the metal complex B6, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 41.6 [lm / W], and the chromaticity coordinates (x, y) were (0.47, 0.44).

<Example D20> Production and Evaluation of Light-Emitting Element D20 "Compound HM-1, Metal Complex B5, and Metal Complex G3 (Compound HM-1 / Metal Complex B5 / Metal Complex G3) in Example D17 (Formation of Light-Emitting Layer)" = "74 mass% / 25 mass% / 1 mass%)" instead of "Compound HM-1, Metal Complex B7 and Metal Complex G3 (Compound HM-1, Metal Complex B7 / Metal Complex G3 = 74 mass% / 25 Except that “mass% / 1 mass%)” was used, a light emitting device D20 was fabricated in the same manner as in Example D17.

By applying a voltage to the light emitting element D20, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 595 nm was observed. These luminescences were luminescences derived from the metal complex B7, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 49.5 [lm / W], and the chromaticity coordinates (x, y) were (0.47, 0.44).

<Example D21> Production and Evaluation of Light-Emitting Element D21 "Compound HM-1, Metal Complex B5, and Metal Complex G3 (Compound HM-1 / Metal Complex B5 / Metal Complex G3" in Example D17 (Formation of Light-Emitting Layer) = “74% by mass / 25% by mass / 1% by mass)”, “compound HM-1, metal complex B8 and metal complex G3 (compound HM-1 / metal complex B8 / metal complex G3 = 74% by mass / 25”) Except for using “mass% / 1 mass%)”, a light emitting device D21 was fabricated in the same manner as in Example D17.

By applying a voltage to the light emitting element D21, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 595 nm was observed. These luminescences were luminescences derived from the metal complex B8, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 52.2 [lm / W], and the chromaticity coordinates (x, y) were (0.45, 0.45).

<Example D22> Production and Evaluation of Light-Emitting Element D22 "Compound HM-1, Metal Complex B5, and Metal Complex G3 (Compound HM-1 / Metal Complex B5 / Metal Complex G3" in Example D17 (Formation of Light-Emitting Layer) = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B9 and metal complex G3 (compound HM-1 / metal complex B9 / metal complex G3 = 74 mass% / 25 Except that “mass% / 1 mass%)” was used, a light emitting device D22 was fabricated in the same manner as in Example D17.

By applying a voltage to the light emitting element D22, EL light emission having a maximum emission wavelength of an emission spectrum at 480 nm, 510 nm, and 595 nm was observed. These luminescences were luminescence derived from the metal complex B9, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 49.6 [lm / W], and the chromaticity coordinates (x, y) were (0.46, 0.46).

<Comparative Example CD5> Production and Evaluation of Light-Emitting Element CD5 "Compound HM-1, Metal Complex B5 and Metal Complex G3 (Compound HM-1 / Metal Complex B5 / Metal Complex G3) in Example D7 (Formation of Light-Emitting Layer)" = “74 mass% / 25 mass% / 1 mass%)” instead of “compound HM-1, metal complex B4 and metal complex G3 (compound HM-1 / metal complex B4 / metal complex G3 = 74 mass% / 25 Except for using “mass% / 1 mass%)”, a light emitting device CD5 was fabricated in the same manner as in Example D7.

By applying a voltage to the light-emitting element CD5, EL light emission having a maximum emission wavelength of an emission spectrum at 465 nm, 515 nm, and 595 nm was observed. These luminescences were luminescences derived from the metal complex B4, the metal complex G3, and the polymer compound EML-1. The light emission efficiency at ²⁰ cd / m ² was 24.9 [lm / W], and the chromaticity coordinates (x, y) were (0.47, 0.44).

Claims (11)

The composition containing the metal complex represented by Formula (1), and the metal complex represented by Formula (2).

[Where:
M represents a rhodium atom, a palladium atom, an iridium atom, or a platinum atom.
n ¹ represents an integer of 1 or more, n ² represents an integer of 0 or more, and n ¹ + n ² is 2 or 3.
When M is 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 represents a carbon atom or a nitrogen atom. When a plurality of E ¹ are present, they may be the same or different.
Ring B represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, 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 B are present, they may be the same or different.
Z ^1A represents a group represented by ^═N— or a group represented by ═C (R ^Z1A ) —. When a plurality of Z ^1A are present, they may be the same or different. R ^Z1A represents 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, and these groups are substituent groups. You may have.
R ¹ represents an alkyl group having 2 to 30 carbon atoms, and these groups may have a substituent. When a plurality of R ¹ are present, they may be the same or different.
Ar ^1A represents a group represented by the formula (Ar-1A). When a plurality of Ar ^1A are present, they may be the same or different.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represent 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 together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ]

[Where:
Ring A represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be bonded to each other to form a ring together with the atoms to which they are bonded.
R ² and R ³ each independently represents 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, The group may have a substituent. ]

[Where:
M ² represents a rhodium atom, a palladium atom, an iridium atom or a platinum atom.
n ³ represents an integer of 1 or more, n ⁴ represents an integer of 0 or more, and n ³ + n ⁴ is 2 or 3.
When M ² is a rhodium atom or an iridium atom, n ³ + n ⁴ is 3, and when M ² is a palladium atom or a platinum atom, n ³ + n ⁴ is 2.
E ⁴ represents a carbon atom or a nitrogen atom. When a plurality of E ⁴ are present, they may be the same or different.
Ring L ¹ represents a 6-membered aromatic heterocyclic ring, and this ring may have a substituent. When a plurality of such substituents are present, 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 are present, they may be the same or different.
Ring L ² represents an aromatic hydrocarbon ring or aromatic heterocyclic ring, these rings may have a substituent. When a plurality of such substituents are present, 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 are present, they may be the same or different.
The substituent that the ring L ¹ may have and the substituent that the ring L ² may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
At least one ring selected from the group consisting of ring L ¹ and ring L ² has a group represented by the formula (1-T) as a substituent. When a plurality of groups represented by the formula (1-T) are present, they may be the same or different.
A ³ -G ² -A ⁴ represents a bidentate ligand of the anionic. A ³ and A ⁴ each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring. G ² represents a single bond or an atomic group constituting a bidentate ligand together with A ³ and A ⁴ . When a plurality of A ³ -G ² -A ⁴ are present, they may be the same or different. ]

[Wherein R ^1T represents 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, and these groups are substituted. It may have a group. ] The composition according to claim 1, wherein the metal complex represented by the formula (1) is a metal complex represented by the formula (1-1).

[Where:
M, Z ^1A , n ¹ , n ² , R ¹ , Ar ^1A and A ¹ -G ¹ -A ² represent the same meaning as described above.
Ring B ¹ represents a benzene ring, a pyridine ring or a diazabenzene ring, and E ^1B , E ^2B , E ^3B and E ^4B each independently represent a nitrogen atom or a carbon atom. When a plurality of E ^1B , E ^2B , E ^3B and E ^4B are present, they may be the same or different. When E ^1B is a nitrogen atom, R ^1B does not exist. When E ^2B is a nitrogen atom, R ^2B does not exist. When E ^3B is a nitrogen atom, R ^3B does not exist. When E ^4B is a nitrogen atom, R ^4B does not exist.
R ^1B , R ^2B , R ^3B and R ^4B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group Represents a group or a halogen atom, and these groups optionally have a substituent. When there are a plurality of R ^1B , R ^2B , R ^3B and R ^4B , they may be the same or different. R ^1B and R ^2B , R ^2B and R ^3B , and R ^3B and R ^4B may be bonded to each other to form a ring together with the atoms to which they are bonded. ] The composition according to claim 2, wherein the metal complex represented by the formula (1-1) is a metal complex represented by the formula (1-2).

[Wherein, M, Z ^1A , n ¹ , n ² , R ¹ , Ar ^1A , A ¹ -G ¹ -A ² , R ^1B , R ^2B , R ^3B and R ^4B represent the same meaning as described above. ] The composition according to any one of claims 1 to 3, wherein the group represented by the formula (Ar-1A) is a group represented by the formula (Ar-2A).

[Wherein R ² and R ³ represent the same meaning as described above.
Ring A ¹ represents a benzene ring, a pyridine ring or a diazabenzene ring, and E ^1A , E ^2A and E ^3A each independently represent a nitrogen atom or a carbon atom. When E ^1A is a nitrogen atom, R ^1A does not exist. When E ^2A is a nitrogen atom, R ^2A does not exist. When E ^3A is a nitrogen atom, R ^3A does not exist.
R ^1A , R ^2A and R ^3A are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or halogen. Represents an atom, and these groups optionally have a substituent. R ^1A and R ^2A , and R ^2A and R ^3A may be bonded to each other to form a ring together with the atoms to which they are bonded. ] The composition according to claim 4, wherein the group represented by the formula (Ar-2A) is a group represented by the formula (Ar-3A).

[Wherein, R ² , R ³ , R ^1A , R ^2A and R ^3A represent the same meaning as described above. ] The composition according to any one of claims 1 to 5, wherein the metal complex represented by the formula (2) is a metal complex represented by the formula (2-B).

[Where:
M ² , n ³ , n ⁴ and A ³ -G ² -A ⁴ represent the same meaning as described above.
Ring L ^1B represents a pyridine ring or a pyrimidine ring, Ring L ^2B represents a benzene ring, a pyridine ring or a diazabenzene ring, and E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B each independently represents a nitrogen atom or a carbon atom. When there are a plurality of E ^11B , E ^12B , E ^13B , E ^14B , E ^21B , E ^22B , E ^23B and E ^24B , they may be the same or different. When E ^11B is a nitrogen atom, R ^11B does not exist. When E ^12B is a nitrogen atom, R ^12B does not exist. When E ^13B is a nitrogen atom, R ^13B does not exist. When E ^14B is a nitrogen atom, R ^14B does not exist. When E ^21B is a nitrogen atom, R ^21B does not exist. When E ^22B is a nitrogen atom, R ^22B does not exist. When E ^23B is a nitrogen atom, R ^23B does not exist. When E ^24B is a nitrogen atom, R ^24B does not exist.
R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B each independently represent a hydrogen atom or a group represented by the formula (1-T). When there are a plurality of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B , they may be the same or different. R ^11B and R ^12B , R ^12B and R ^13B , R ^13B and R ^14B , R ^11B and R ^21B , R ^21B and R ^22B , R ^22B and R ^23B , and R ^23B and R ^24B are combined, You may form the ring with the atom to which each couple | bonds. However, at least one selected from the group consisting of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T). ] The metal complex represented by the formula (2-B) is represented by the metal complex represented by the formula (2-B1), the metal complex represented by the formula (2-B2), and the formula (2-B3). The composition according to claim 6, which is a metal complex represented by formula (2-B4) or a metal complex represented by formula (2-B5).

[Where:
M ² , n ³ , n ⁴ , R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B , R ^24B and A ³ -G ² -A ⁴ represent the same meaning as described above.
n ³¹ and n ³² each independently represent an integer of 1 or more, and n ³¹ + n ³² is 2 or 3. When M ² is a rhodium atom or an iridium atom, n ³¹ + n ³² is 3, and when M ² is a palladium atom or a platinum atom, n ³¹ + n ³² is 2.
R ^15B , R ^16B , R ^17B and R ^18B each independently represent a hydrogen atom or a group represented by the formula (1-T). When there are a plurality of R ^15B , R ^16B , R ^17B and R ^18B , they may be the same or different. R ^15B and R ^16B , R ^16B and R ^17B , and R ^17B and R ^18B may be bonded to each other to form a ring together with the atoms to which they are bonded. However, in formula (2-B1) and formula (2-B3), at least one selected from the group consisting of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is In the formula (2-B2), at least one selected from the group consisting of R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T): In the formula (2-B4), at least one selected from the group consisting of R ^11B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T). In the formula (2-B5), at least one selected from the group consisting of R ^11B , R ^12B , R ^21B , R ^22B , R ^23B and R ^24B is a group represented by the formula (1-T). And a group represented by the formula (1-T) A. ] R ^1T is an alkyl group which may have a substituent, a group represented by the formula (DA), a group represented by the formula (D-B), or a formula (D-C). The composition according to any one of claims 1 to 7, which is a group represented.

[Where:
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 optionally have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally 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 optionally have a substituent. A plurality of ^TDAs may be the same or different. ]

[Where:
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 optionally have a substituent. A plurality of ^GDA 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 optionally have a substituent. A plurality of ^TDAs may be the same or different. ]

[Where:
m ^DA1 represents an integer of 0 or more.
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When a plurality of Ar ^DA1 are present, they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ] The composition according to any one of claims 1 to 8, further comprising a compound represented by the formula (H-1).

[Where:
Ar ^H1 and Ar ^H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent.
n ^H1 and n ^H2 each independently represent 0 or 1. When a plurality of n ^H1 are present, they may be the same or different. A plurality of n ^H2 may be the same or different.
n ^H3 represents an integer of 0 or more and 10 or less.
L ^H1 represents an arylene group, a divalent heterocyclic group, or a group represented by — [C (R ^H11 ) ₂ ] n ^H11 —, and these groups ^optionally have a substituent. When a plurality of L ^H1 are present, they may be the same or different. n ^H11 represents an integer of 1 or more and 10 or less. R ^H11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^H11 may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
L ^H2 represents a group represented by -N (-L ^H21 -R ^H21 )-. When a plurality of L ^H2 are present, they may be the same or different. L ^H21 represents a single bond, an arylene group or a divalent heterocyclic group, and these groups may have a substituent. R ^H21 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. ]   The hole transport material, the hole injection material, the electron transport material, the electron injection material, the light emitting material, the antioxidant, and further contains at least one selected from the group consisting of an antioxidant and a solvent. A composition according to 1.   The light emitting element containing the composition as described in any one of Claims 1-10.