JP2018085505A - Light emitting device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a light emitting device having excellent external quantum efficiency.SOLUTION: The light emitting device includes: an anode; a cathode; a first organic layer and a second organic layer provided between the anode and the cathode. The first organic layer is a layer A containing a metal complex having a specific structure. The second organic layer is a polymer compound containing a constitutional unit having a group in which one or more hydrogen atoms is removed from metal complex represented by Formula (2), and a layer B containing at least one of crosslinked polymers of the polymer compound, or a layer C 'containing metal complex represented by Formula (2) and a crosslinked product of a compound having a crosslinking group.SELECTED DRAWING: None

Description

  The present invention relates to a light emitting element.

  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 metal complex 1 represented by the following formula and a red phosphorescent material. Note that the light-emitting element described in Patent Document 1 is a light-emitting element including a phosphorescent material in only one layer. Further, the light-emitting element described in Patent Document 1 is a light-emitting element having only one light-emitting layer.

JP 2011-253980 A

  However, the above-described light emitting device does not necessarily have sufficient external quantum efficiency.

  Therefore, an object of the present invention is to provide a light-emitting element having excellent external quantum 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、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又は炭素原子数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。
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。］
［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］に記載の発光素子。

［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］陽極と、陰極と、前記陽極及び前記陰極の間に設けられた第１の有機層及び第２の有機層と、を有し、
前記第１の有機層及び前記第２の有機層が、発光層であり、
前記第１の有機層が、式（１’）で表される金属錯体を含有する層Ａ’である、発光素子。

［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、該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、前記式（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。］
［４］前記第２の有機層が、
前記式（２）で表される金属錯体から水素原子１個以上を除いた基を有する構成単位を含む高分子化合物、及び、前記高分子化合物の架橋体のうち、少なくとも１種を含有する層Ｂ、又は、
前記式（２）で表される金属錯体を含有する層Ｃである、［３］に記載の発光素子。
［５］陽極と、陰極と、前記陽極及び前記陰極の間に設けられた第１の有機層及び第２の有機層と、を有し、
前記第１の有機層が、前記式（１’）で表される金属錯体を含有する層Ａ’であり、
前記第２の有機層が、
前記式（２）で表される金属錯体から水素原子１個以上を除いた基を有する構成単位を含む高分子化合物、及び、前記高分子化合物の架橋体のうち、少なくとも１種を含有する層Ｂ、又は、
前記式（２）で表される金属錯体を含有する層Ｃ
である、発光素子。
［６］前記第２の有機層が、前記層Ｂであり、
前記高分子化合物が、架橋基を有する構成単位を更に含む、［１］、［２］、［４］及び［５］のいずれかに記載の発光素子。
［７］前記第２の有機層が、前記層Ｂであり、
前記構成単位が、式（２−１Ｂ）で表される構成単位、式（２−２Ｂ）で表される構成単位、式（２−３Ｂ）で表される構成単位又は式（２−４Ｂ）で表される構成単位である、［１］、［２］及び［４］〜［６］のいずれかに記載の発光素子。

［式中、
Ｍ^１Ｂは、式（２）で表される金属錯体から水素原子１個を除いた基を表す。
Ｌ^Ｃは、酸素原子、硫黄原子、−Ｎ（Ｒ^Ａ）−、−Ｃ（Ｒ^Ｂ）_２−、−Ｃ（Ｒ^Ｂ）＝Ｃ（Ｒ^Ｂ）−、−Ｃ≡Ｃ−、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^Ａは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Ｂ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^Ｂ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^Ｃ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^ｃ１は０以上の整数を表す。］

［式中、
Ｍ^１Ｂは前記と同じ意味を表す。
Ｌ^ｄ及びＬ^ｅは、それぞれ独立に、酸素原子、硫黄原子、−Ｎ（Ｒ^Ａ）−、−Ｃ（Ｒ^Ｂ）_２−、−Ｃ（Ｒ^Ｂ）＝Ｃ（Ｒ^Ｂ）−、−Ｃ≡Ｃ−、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^Ａ及びＲ^Ｂは、前記と同じ意味を表す。Ｌ^ｄ及びＬ^ｅ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。
ｎ^ｄ１及びｎ^ｅ１は、それぞれ独立に、０以上の整数を表す。複数存在するｎ^ｄ１は、同一でも異なっていてもよい。
Ａｒ^１Ｍは、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。］

［式中、
Ｌ^ｄ及びｎ^ｄ１は、前記と同じ意味を表す。
Ｍ^２Ｂは、式（２）で表される金属錯体から水素原子２個を除いた基を表す。］

［式中、
Ｌ^ｄ及びｎ^ｄ１は、前記と同じ意味を表す。
Ｍ^３Ｂは、式（２）で表される金属錯体から水素原子３個を除いた基を表す。］
［８］前記第２の有機層が、前記層Ｂ又は前記層Ｃ’であり、
前記架橋基が、架橋基Ａ群から選ばれる架橋基である、［１］、［２］又は［６］に記載の発光素子。
（架橋基Ａ群）

［式中、Ｒ^ＸＬは、メチレン基、酸素原子又は硫黄原子を表し、ｎ^ＸＬは、０〜５の整数を表す。Ｒ^ＸＬが複数存在する場合、それらは同一でも異なっていてもよい。複数存在するｎ^ＸＬは、同一でも異なっていてもよい。＊１は結合位置を表す。これらの架橋基は置換基を有していてもよい。］
［９］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］〜［８］のいずれかに記載の発光素子。

［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。］
［１０］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］〜［９］のいずれかに記載の発光素子。

［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、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。Ｒ^１１Ｂ、Ｒ^１２Ｂ、Ｒ^１３Ｂ、Ｒ^１４Ｂ、Ｒ^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。］
［１１］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、［１０］に記載の発光素子。

［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、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^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。］
［１２］前記第１の有機層が、式（Ｈ−１）で表される化合物、及び／又は、式（Ｙ）で表される構成単位を含む高分子化合物を更に含有する、［１］〜［１１］のいずれかに記載の発光素子。

［式中、
Ａｒ^Ｈ１及びＡｒ^Ｈ２は、それぞれ独立に、アリール基又は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。］

［式中、Ａｒ^Ｙ１は、アリーレン基、２価の複素環基、又は、アリーレン基と２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。］
［１３］前記第１の有機層が、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料及び酸化防止剤からなる群より選ばれる少なくとも１種を更に含有する、［１］〜［１２］のいずれかに記載の発光素子。
［１４］前記第１の有機層と前記第２の有機層とが隣接している、［１］〜［１３］のいずれかに記載の発光素子。
［１５］前記第２の有機層が、前記陽極及び前記第１の有機層との間に設けられた層である、［１］〜［１４］のいずれかに記載の発光素子。 The present invention provides the following [1] to [15].
[1] An anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer A containing a metal complex represented by the formula (1),
The second organic layer is
Layer B containing at least one of a polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (2), and a crosslinked product of the polymer compound Or
The light emitting element which is layer C 'containing the crosslinked body of the compound which has a metal complex represented by Formula (2), and a crosslinking group.

[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 a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, or an alkyl group having 2 to 30 carbon atoms, This group 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.
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. ]
[2] The light emitting device 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] An anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer and the second organic layer are light emitting layers;
The light emitting element whose said 1st organic layer is layer A 'containing the metal complex represented by Formula (1').

[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 the group 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. ]
[4] The second organic layer is
A layer containing at least one of a polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by the formula (2), and a crosslinked product of the polymer compound B or
The light-emitting element according to [3], which is the layer C containing the metal complex represented by the formula (2).
[5] having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer A ′ containing a metal complex represented by the formula (1 ′),
The second organic layer is
A layer containing at least one of a polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by the formula (2), and a crosslinked product of the polymer compound B or
Layer C containing a metal complex represented by the formula (2)
A light emitting element.
[6] The second organic layer is the layer B,
The light emitting device according to any one of [1], [2], [4], and [5], wherein the polymer compound further includes a structural unit having a crosslinking group.
[7] The second organic layer is the layer B,
The structural unit is a structural unit represented by formula (2-1B), a structural unit represented by formula (2-2B), a structural unit represented by formula (2-3B), or formula (2-4B). The light emitting element in any one of [1], [2] and [4]-[6] which is a structural unit represented by these.

[Where:
M ^1B represents a group obtained by removing one hydrogen atom from the metal complex represented by the formula (2).
L ^C represents an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C≡C—, an arylene group or It represents a divalent heterocyclic group, and these groups may have a substituent. R ^A 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. R ^B 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 ^RBs may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. When a plurality of ^LC are present, they may be the same or different.
n ^c1 represents an integer of 0 or more. ]

[Where:
M ^1B represents the same meaning as described above.
L ^d and ^{L e} each independently represent an oxygen atom, a sulfur _{^{atom, -N (R A) -,}} - C (R B) 2 -, - C (R B) = C (R B) -, - C Represents ≡C—, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A and R ^B represent the same meaning as described above. When a plurality of L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. ]

[Where:
L ^d and n ^d1 represent the same meaning as described above.
M ^2B represents a group obtained by removing two hydrogen atoms from the metal complex represented by the formula (2). ]

[Where:
L ^d and n ^d1 represent the same meaning as described above.
M ^3B represents a group obtained by removing three hydrogen atoms from the metal complex represented by the formula (2). ]
[8] The second organic layer is the layer B or the layer C ′,
The light emitting device according to [1], [2], or [6], wherein the crosslinking group is a crosslinking group selected from the crosslinking group A group.
(Crosslinking group A group)

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different. A plurality of n ^XL may be the same or different. * 1 represents a binding position. These crosslinking groups may have a substituent. ]
[9] The light emitting device according to any one of [1] to [8], 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. ]
[10] The light emitting device according to any one of [1] to [9], 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 are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent. 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. ]
[11] 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 light emitting element according to [10], 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 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 ^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. ]
[12] The first organic layer further contains a compound represented by the formula (H-1) and / or a polymer compound containing a structural unit represented by the formula (Y). [1] -The light emitting element in any one of [11].

[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. ]

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, and these groups have a substituent. It may be. ]
[13] The first organic layer further contains at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. 1]-[12] The light emitting element in any one.
[14] The light emitting device according to any one of [1] to [13], wherein the first organic layer and the second organic layer are adjacent to each other.
[15] The light emitting device according to any one of [1] to [14], wherein the second organic layer is a layer provided between the anode and the first organic layer.

  According to the present invention, a light emitting device having excellent external quantum 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, etc. Preferably, it is a crosslinking group represented by Formula (XL-1) to Formula (XL-17) of the crosslinking group A group.

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

<Light emitting element>
The first light emitting device of this embodiment is a light emitting device having an anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode.

<First organic layer>
The first organic layer is a layer A containing a metal complex represented by the formula (1). The layer A may contain individually 1 type of the metal complex represented by Formula (1), and may contain 2 or more types. The layer A containing the metal complex represented by the formula (1) is preferably a layer A ′ containing the metal complex represented by the formula (1 ′). That is, the metal complex represented by the formula (1) is preferably a metal complex represented by the formula (1 ′). The layer A ′ may contain one kind of metal complex represented by the formula (1 ′) alone or may contain two or more kinds.

-Metal complex represented by formula (1) and metal complex represented by formula (1 ') The metal complex represented by formula (1) and the metal complex represented by formula (1') are usually at room temperature. A metal complex exhibiting phosphorescence at (25 ° C.), preferably a metal complex exhibiting light emission from a triplet excited state at room temperature.

The metal complex represented by the formula (1) and the metal complex represented by the formula (1 ′) are a central metal M, a ligand whose number is defined by the subscript n ¹ , and a subscript. and a ligand whose number is defined by n ² .

  M is preferably an iridium atom or a platinum atom, and more preferably an iridium atom, because the external quantum efficiency of the light emitting device of this 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, since the external quantum efficiency of the light-emitting device of this embodiment is more excellent. Preferred is a benzene ring, fluorene ring, dihydrophenanthrene ring, pyridine ring, diazabenzene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring, more preferred is a benzene ring, pyridine ring or diazabenzene ring, and particularly preferred is benzene. It is a ring, and these rings 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, an aryl group, a monovalent heterocyclic group, and a substituted amino group are more excellent in the external quantum efficiency of the light-emitting element of this embodiment, and therefore have the formula (DA ), A group represented by (DB) or (DC), and a group represented by formula (DA) or (DC) is more preferable.

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.

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 of the metal complex represented by the formula (1 ′) is 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.

R ¹ is preferably a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group, a fluorine atom, or an alkyl group having 2 to 30 carbon atoms, and more preferably. Is a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group or an alkyl group having 2 to 30 carbon atoms, more preferably a cycloalkyl group, an aryl group or 2 to 30 carbon atoms. The following alkyl groups, particularly preferably an aryl group or an alkyl group having 2 to 30 carbon atoms, particularly preferably an alkyl group having 2 to 30 carbon atoms, and these groups are further substituted It may have a group.
That is, R ¹ is preferably R ^{1 ′} .

Examples and preferred ranges of the aryl group, monovalent heterocyclic group or substituted amino group for R ¹ 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.

The number of carbon atoms of the alkyl group in R ¹ and R ^{1 ′} does not include the number of carbon atoms of the substituent, and is preferably 3 or more, more preferably 4 or more, and even more preferably 5 or more. The number of carbon atoms of the alkyl group in R ¹ and R ^{1 ′} does not include the number of carbon atoms of the substituent, is preferably 30 or less, more preferably 20 or less, and even more preferably 15 or less. Particularly preferably, it is 10 or less, and particularly preferably 8 or less.

When R ¹ is an alkyl group having 2 to 30 carbon atoms, the substituent that R ¹ may have is preferably a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or an aryloxy group. A monovalent heterocyclic group, a substituted amino group or a halogen atom, more preferably 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, they are a cycloalkyl group or an aryl group, and these groups may further have a substituent.

Since the synthesis of the metal complex represented by the formula (1) and the metal complex represented by the formula (1 ′) is facilitated, an alkyl group having 2 to 30 carbon atoms in R ¹ and R ^{1 ′} is substituted. It preferably has no group.

In case R ¹ is an alkyl group having 2 to 30 carbon atoms, an aryl group in the substituent which may be R ¹ optionally has, monovalent examples and preferred ranges of the heterocyclic group or a substituted amino group, ring Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that B may have are the same as the preferred range.

The alkyl group having 2 to 30 carbon atoms in R ¹ and R ^{1 ′} is preferably a branched alkyl group having 3 to 30 carbon atoms because the external quantum efficiency of the light emitting device of this embodiment is more excellent. More preferably a branched alkyl group having 3 to 15 carbon atoms, still more preferably a branched alkyl group having 3 to 10 carbon atoms, and particularly preferably a branched alkyl group having 4 to 10 carbon atoms. An alkyl group, particularly preferably a branched alkyl group having 5 to 8 carbon atoms. These groups preferably have no substituent.

In the alkyl group in R ¹ and 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-dimethyl group. Butyl 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-di- Propylbutyl, 1-butylhexyl, 1-propylheptyl, 1,1,3,7-tetramethyloctyl and 1,1, - triethyl octyl group are preferable.

When R ¹ is other than an alkyl group having 2 to 30 carbon atoms, examples and preferred ranges of the substituent that R ¹ may have are further included in the substituent that ring B may have. Examples of the substituents that may be present and the preferred ranges are the same.

Examples and preferred ranges of the substituent which may be possessed by R 1 ^'is when R ¹ is an alkyl group having 2 to 30 carbon atoms, examples of the substituent which may be R ¹ optionally has and It is the same as a preferable range.

[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, because the external quantum efficiency of the light-emitting device of the present embodiment is more excellent. Preferred is a benzene ring, fluorene ring, dihydrophenanthrene ring, pyridine ring, diazabenzene ring, carbazole ring, dibenzofuran ring or dibenzothiophene ring, more preferred is a benzene ring, pyridine ring or diazabenzene ring, and particularly preferred is benzene. It is a ring, and these rings 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, an alkyl 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 of the metal complex represented by the formula (1 ′) is 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.

Since the alkyl group in R ² and R ³ facilitates the synthesis of the metal complex represented by the formula (1) and the metal complex represented by the formula (1 ′), it preferably has 1 to 7 carbon atoms. An alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms, still more preferably an alkyl group having 1 to 3 carbon atoms, and it is particularly preferable that these groups have no substituent. preferable.

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) because the external quantum efficiency of the light emitting device of this 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) and Formula (1′-1)>
The metal complex represented by the formula (1) is preferably a metal complex represented by the formula (1-1) because the external quantum efficiency of the light emitting device of this embodiment is more excellent.
The metal complex represented by the formula (1 ′) is preferably a metal complex represented by the formula (1′-1) because the external quantum efficiency of the light emitting device of this embodiment is more excellent.

In the formula, M, Z ^1A , n ¹ , n ² , R ¹ , Ar ^1A , A ¹ -G ¹ -A ² , E ^1B , E ^2B , E ^3B , E ^4B , R ^1B , R ^2B , R ^3B , R ^4B and ring B ¹ represent the same meaning as described above.

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 external quantum efficiency of the light emitting device of this embodiment is more excellent.
The metal complex represented by the formula (1′-1) is preferably a metal complex represented by the formula (1′-2) because the external quantum efficiency of the light emitting device of this embodiment is more excellent.

In the formula, 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.

  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.

[Host material]
Since the external quantum efficiency of the light emitting device of the present embodiment is more excellent, the first organic layer has a metal complex represented by the formula (1) or the formula (1 ′), a hole injection property, a hole transport property, A layer containing a host material having at least one function of electron injection property and electron transport property is preferable. The 1st organic layer may contain 1 type of host materials independently, and may contain 2 or more types.

  When the first organic layer is a layer containing a metal complex represented by formula (1) or formula (1 ′) and a host material, a metal represented by formula (1) or formula (1 ′) The content of the complex is usually 0.1 to 50 parts by mass, preferably 1 to 50 parts by mass, with the total of the metal complex represented by formula (1) or formula (1 ′) and the host material being 100 parts by mass. It is 45 mass parts, More preferably, it is 5-40 mass parts, More preferably, it is 10-30 mass parts.

Since the lowest excited triplet state (T ₁ ) of the host material is more excellent in the external quantum efficiency of the light emitting device of this embodiment, the lowest excitation of the metal complex represented by the formula (1) or the formula (1 ′) It is preferable that the energy level be higher than that of the triplet state (T ₁ ).

  As the host material, since the light-emitting element of this embodiment can be manufactured by a solution coating process, the host material has solubility in a solvent capable of dissolving the metal complex represented by the formula (1) or the formula (1 ′). It is preferable that it is shown.

  The host material is classified into a low molecular compound (low molecular host) and a high molecular compound (polymer host), and the first organic layer may contain any host material. The host material that may be contained in the first organic layer 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.

[Polymer host]
A polymer compound preferable as the host compound (hereinafter referred to as “polymer host”) is preferably a polymer compound containing a structural unit represented by the formula (Y).

The arylene group represented by Ar ^Y1 is more preferably the formula (A-1), the formula (A-2), the formula (A-6) to the formula (A-10), the formula (A-19) or the formula A group represented by formula (A-20), more preferably formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19). ), And these groups may have a substituent.

The divalent heterocyclic group represented by Ar ^Y1 is more preferably a formula (AA-1) to a formula (AA-4), a formula (AA-10) to a formula (AA-15), a formula (AA- 18) to a group represented by formula (AA-21), formula (AA-33), or formula (AA-34), more preferably formula (AA-4), formula (AA-10), formula It is a group represented by (AA-12), formula (AA-14) or formula (AA-33), and these groups may have a substituent.

More preferred ranges and further preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group in which the arylene group represented by Ar ^Y1 and the divalent heterocyclic group are directly bonded are the above-mentioned Ar. This is the same as the more preferable range and further preferable range of the arylene group and divalent heterocyclic group represented by ^Y1 .

  Examples of the “divalent group in which an arylene group and a divalent heterocyclic group are directly bonded” include a group represented by the following formula, and these may have a substituent.

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

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

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

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-1) to the formula (Y-10). From the viewpoint of the external quantum efficiency of the light emitting device of the present embodiment. Is preferably a structural unit represented by formula (Y-1) to formula (Y-3), and preferably from formula (Y-4) from the viewpoint of electron transport properties of the light-emitting device of the present embodiment. Is a structural unit represented by Formula (Y-7), and is preferably represented by Formula (Y-8) to Formula (Y-10) from the viewpoint of hole transportability of the light emitting device of this embodiment. This is a structural unit.

In the formula, R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

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

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

In the formula, R ^Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y11 may be the same or different.

R ^Y11 is preferably an alkyl group, a cycloalkyl group, or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups optionally have a substituent.

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

R ^Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. You may do it.

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

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

In ^XY1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded. When R ^Y2 forms a ring, —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — Are preferably groups represented by the formulas (Y-B1) to (Y-B5), more preferably groups represented by the formula (Y-B3). It may have a substituent.

In the formula, R ^Y2 represents the same meaning as described above.

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

In the formula, R ^Y1 and X ^Y1 represent the same meaning as described above.

In the formula, R ^Y1 and X ^Y1 represent the same meaning as described above.

  The structural unit represented by the formula (Y-3) is preferably a structural unit represented by the formula (Y-3 ′).

In the formula, R ^Y11 and X ^Y1 represent the same meaning as described above.

In the formula, R ^Y1 represents the same meaning as described above. R ^Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent.

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

  The structural unit represented by the formula (Y-4) is preferably a structural unit represented by the formula (Y-4 ′), and the structural unit represented by the formula (Y-6) is represented by the formula (Y It is preferable that it is a structural unit represented by -6 ').

In the formula, R ^Y1 and R ^Y3 represent the same meaning as described above.

In the formula, R ^Y1 represents the same meaning as described above. R ^Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.

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

  As the structural unit represented by Formula (Y), for example, a structural unit composed of an arylene group represented by Formula (Y-101) to Formula (Y-121), Formula (Y-201) to Formula (Y— 206), a divalent heterocyclic group, an arylene group represented by the formula (Y-300) to the formula (Y-304) and a divalent heterocyclic group directly bonded to each other. The structural unit which consists of these groups is mentioned.

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, is excellent in the external quantum efficiency of the light-emitting device of the present embodiment. Therefore, the total amount of the structural units contained in the polymer host The amount is preferably 0.5 to 90 mol%, more preferably 30 to 80 mol%.

A structural unit represented by the formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, Since the charge transport property of the light emitting device of this embodiment is excellent, it is preferably 0.5 to 40 mol%, more preferably 3 to 30 mol%, based on the total amount of structural units contained in the polymer host. is there.

  One type of structural unit represented by the formula (Y) may be contained in the polymer host, or two or more types may be contained.

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

Where
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, and these groups are substituents You may have. When a plurality of Ar ^X2 and Ar ^X4 are present, they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of R ^X2 and R ^X3 are present, they may be the same or different.

a ^X1 is preferably 2 or less, more preferably 1, because the external quantum efficiency of the light emitting device of this embodiment is more excellent.
a ^X2 is preferably 2 or less, more preferably 0, because the external quantum efficiency of the light emitting device of this embodiment is more excellent.

R ^X1 , R ^X2 and R ^X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. Also good.

The arylene group represented by Ar ^X1 and Ar ^X3 is more preferably a group represented by Formula (A-1) or Formula (A-9), and even more preferably represented by Formula (A-1). These groups may have a substituent.

The divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 is more preferably represented by formula (AA-1), formula (AA-2), or formula (AA-7) to formula (AA-26). These groups may have a substituent.

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

The arylene group represented by Ar ^X2 and Ar ^X4 is more preferably a formula (A-1), a formula (A-6), a formula (A-7), a formula (A-9) to a formula (A-11). ) Or a group represented by the formula (A-19), and these groups optionally have a substituent.

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

More preferred ranges and further preferred ranges of the arylene group and the divalent heterocyclic group in the divalent group in which the arylene group represented by Ar ^X2 and Ar ^X4 and the divalent heterocyclic group are directly bonded are respectively This is the same as the more preferable range and further preferable range of the arylene group and divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 .

Examples of the divalent group in which the arylene group represented by Ar ^X2 and Ar ^X4 and the divalent heterocyclic group are directly bonded include an arylene group represented by Ar ^Y1 in the formula (Y) and a divalent heterocyclic group And the same as the divalent group directly bonded to each other.

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

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

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

In the formula, R ^X4 and R ^X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano group. These groups may have a substituent. A plurality of R ^X4 may be the same or different. A plurality of R ^X5 may be the same or different, and adjacent R ^X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded.

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

  Examples of the structural unit represented by Formula (X) include structural units represented by Formula (X1-1) to Formula (X1-11), and preferably Formula (X1-3) to Formula (X1). -10).

  In the polymer host, only one type of structural unit represented by the formula (X) may be included, or two or more types of structural units may be included.

  Examples of the polymer host include polymer compounds P-1 to P-6.

  In the table, p, q, r, s, and t indicate the molar ratio of each structural unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70. The other structural unit means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).

  The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A polymerized copolymer is preferred.

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

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

  In the polymerization method, as a method of charging the monomer, a method of charging the entire amount of the monomer into the reaction system at once, a part of the monomer is charged and reacted, and then the remaining monomer is batched, Examples thereof include a method of charging continuously or divided, a method of charging monomer continuously or divided, and the like.

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

  Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination. When the purity of the polymer host is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, or the like.

[First composition]
The first organic layer includes a metal complex represented by the formula (1) or the formula (1 ′), the host material, the hole transport material, the hole injection material, the electron transport material, the electron injection material, and the light emitting material. (However, it is different from the metal complex represented by Formula (1).) And at least one selected from the group consisting of antioxidants (hereinafter also referred to as “first composition”). It may be a layer containing

[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 first composition, the content of the hole transport material is usually 1 to 400 parts by mass when the metal complex represented by formula (1) or formula (1 ′) is 100 parts by mass, Preferably it is 5-150 mass parts.

  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 first composition, the content of the electron transport material is usually 1 to 400 parts by mass when the metal complex represented by the formula (1) or the formula (1 ′) is 100 parts by mass, preferably Is 5 to 150 parts by mass.

  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 first composition, the contents of the hole injecting material and the electron injecting material are usually 1 to 100 parts by mass, respectively, when the metal complex represented by the formula (1) or the formula (1 ′) is 100 parts by mass. 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]
The light emitting material (however, different from the metal complex represented by the formula (1)) is classified into a low molecular compound and a high molecular compound. 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 polymer compound include arylene groups such as a phenylene group, naphthalenediyl group, fluorenediyl group, phenanthrene diyl group, dihydrophenanthrene diyl group, anthracenediyl group, and pyrenediyl group; a structural unit represented by the formula (X) And a polymer compound containing 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 metal complex shown below, a metal complex represented by the formula (2), a polymer compound of a layer B described later, or a crosslinked product of a polymer compound of a layer B described below, Is a metal complex represented by the formula (2), a polymer compound of the layer B described later, or a crosslinked product of the polymer compound of the layer B described later, more preferably represented by the formula (2). It is a metal complex.

  In the first composition, the content of the light emitting material is usually 1 to 400 parts by mass when the metal complex represented by the formula (1) or the formula (1 ′) is 100 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]
For example, the antioxidant is preferably a compound that is soluble in at least one solvent capable of dissolving the metal complex represented by the formula (1) or the formula (1 ′) and does not inhibit light emission and charge transport. . Examples of the antioxidant include a phenolic antioxidant and a phosphorus antioxidant.

  In the first composition, the content of the antioxidant is usually 0.001 to 10 parts by mass when the metal complex represented by the formula (1) or the formula (1 ′) is 100 parts by mass. .

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

<Ink>
A composition containing a metal complex represented by formula (1) or formula (1 ′) and a solvent (hereinafter also referred to as “first ink”) is prepared by spin coating, casting, or microgravure coating. Method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic printing method, offset printing method, ink jet printing method, capillary coating method, nozzle coating method It can use suitably for wet methods, such as.

  The viscosity of the first ink may be adjusted according to the type of wet method. However, when a solution such as an ink jet printing method is applied to a printing method that passes through a discharge device, clogging at the time of discharge and flight bending occur. Since it is difficult, it is preferably 1 to 20 mPa · s at 25 ° C.

  The solvent contained in the first ink is preferably a solvent 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 first ink, the content of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 100 parts by mass when the metal complex represented by the formula (1) or formula (1 ′) is 100 parts by mass. It is 20000 parts by mass.

<Second organic layer>
Next, the layer B which is one of the preferred embodiments of the second organic layer will be described.

<Layer B>
The layer B includes a structural unit (hereinafter referred to as “metal” in which one or more hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting the metal complex are removed from the metal complex represented by the formula (2). A layer containing at least one of a polymer compound (hereinafter also referred to as “polymer compound of layer B”) and a cross-linked product of the polymer compound of layer B. It is.
In the layer B, the polymer compound of the layer B and the crosslinked product of the polymer compound of the layer B may be contained 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 external quantum efficiency of the light emitting device of this 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, a pyridine ring is particularly 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.

The substituent that the ring L ¹ and the ring L ² may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, A substituted amino group or a halogen atom, more preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a fluorine atom, still more preferably, An alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, particularly preferably a group represented by the formula (DA), (DB) or (DC) Particularly preferred is a group represented by the formula (DA), and these groups may further have a substituent.

At least one of Ring L ¹ and Ring L ² preferably has a substituent.

Examples and preferred ranges of the aryl group in the substituent that the ring L ¹ and the ring L ² may have are the same as examples and preferred ranges of the aryl group in the substituent that the ring B may have.
Examples of the monovalent heterocyclic group in the substituent that the ring L ¹ and the ring L ² may have and preferred ranges thereof are examples of the monovalent heterocyclic group in the substituent that B may have and It is the same as a preferable range.
Examples and preferred ranges of the substituted amino group in the substituent that the ring L ¹ and the ring L ² may have are the same as examples and preferred ranges of the substituted amino group in the substituent that B may have. .

In the groups represented by the formulas ( ^DA ) and (DB) in the substituents that the ring L ¹ and the ring L ² may have, G ^DA is preferably a group represented by the formula (GDA-11) to ( GDA-15), more preferably groups represented by formulas (GDA-11) to (GDA-14), and still more preferably formula (GDA-11) or (GDA-14). It is group represented by these.

In the substituents that the ring L ¹ and the ring L ² may have, the groups represented by the formula (DA) are preferably represented by the formulas (D-A1) to (D-A4). A group represented by the formula (D-A1), (D-A3) or (D-A4), and more preferably a group represented by the formula (D-A1) or (D-A3). And particularly preferably a group represented by the formula (D-A1).

In the substituents that the ring L ¹ and the ring L ² may have, the groups represented by the formula (DB) are preferably represented by the formulas (D-B1) to (D-B3). A group represented by formula (D-B1) or (D-B3), more preferably a group represented by formula (D-B1).

In the substituents that the ring L ¹ and the ring L ² may have, the group represented by the formula (DC) is preferably represented by the formulas (D-C1) to (D-C4). A group represented by formulas (D-C1) to (D-C3), more preferably a group represented by formula (D-C1) or (D-C2). And particularly preferred is a group represented by the formula (D-C1).

When there are a plurality of substituents that the ring L ¹ may have, they 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 there are a plurality of substituents that the ring L ² may have, they 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.
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, It is preferable not to form a ring.

Examples of the substituent that the ring L ¹ and the ring L ² may have further may have a substituent and the ring B may further have a substituent. Examples of the preferred substituents and the preferred ranges are the same.

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 .

<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) because the external quantum efficiency of the light emitting device of this 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.

R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent group. A heterocyclic group, a substituted amino group or a fluorine atom, 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. Or a group represented by the formula (DA), (DB) or (DC), particularly preferably a hydrogen atom or a group represented by the formula (DA). Yes, these groups may have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group in R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B are the ring L ¹ and Examples of the aryl group, monovalent heterocyclic group and substituted amino group in the substituent that the ring L ² may have are the same as the preferred range.

Examples of substituents that R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B, and R ^24B may have are as follows. Are the same as the examples and preferred ranges of the substituents that may further have.

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 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.

Since the external quantum efficiency of the light emitting device of this embodiment is more excellent, at least one of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is an alkyl group, cyclo It is preferably an alkyl 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, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, More preferably, it is 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, A group represented by the formula (D-A), (D-B) or (D-C) is particularly preferred, and is represented by the formula (D-A). Is particularly preferably a group, these groups may have a substituent.

At least one of R ^11B , R ^12B , R ^13B , R ^14B , R ^21B , R ^22B , R ^23B and R ^24B is an alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group When it is a monovalent heterocyclic group, substituted amino group or halogen atom, at least one of R ^12B , R ^13B , R ^22B and R ^23B is 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 preferred, and R ^13B or R ^22B is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, An aryloxy group, monovalent heterocyclic group, substituted amino group or halogen atom; And these groups may have a substituent.

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 the external quantum efficiency of the light emitting device of this embodiment, the metal complex represented by the formula (2-B1), represented by the formula (2-B2). It is preferably a metal complex represented by the formula (2-B3), a metal complex represented by the formula (2-B4), or a metal complex represented by the formula (2-B5). More preferably, it is a metal complex represented by (2-B1), a metal complex represented by formula (2-B2), or a metal complex represented by formula (2-B3). Or a metal complex represented by the formula (2-B2) is more preferred, and a metal complex represented by the formula (2-B1) is particularly preferred.

R ^15B , R ^16B , R ^17B and R ^18B 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 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 or a cycloalkyl group, particularly preferably. Is a hydrogen atom, and these groups may have a substituent.

Examples of aryl group, monovalent heterocyclic group and substituted amino group in R ^15B , R ^16B , R ^17B and R ^18B and preferred ranges thereof are the substituents that ring L ¹ and ring L ² may have, respectively. Are the same as the examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group.

Examples of substituents that R ^15B , R ^16B , R ^17B and R ^18B may have and preferred ranges thereof are examples of substituents that the substituent which ring B may have may further have. And the same as the preferred range.

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.

[Metal complex structural unit]
The metal complex constituent unit is preferably one or more and five or less hydrogen atoms from the metal complex represented by the formula (2) because the external quantum efficiency of the light emitting device of this embodiment is excellent and the synthesis is easy. And more preferably a structural unit containing a group in which 1 or more and 3 or less hydrogen atoms have been removed from the metal complex represented by formula (2). A structural unit represented by (2-1B), a structural unit represented by formula (2-2B), a structural unit represented by formula (2-3B), or a structural unit represented by formula (2-4B) And particularly preferably a structural unit represented by the formula (2-1B), a structural unit represented by the formula (2-2B), or a structural unit represented by the formula (2-3B), particularly preferably. It is a structural unit represented by Formula (2-3B).

The structural unit R ^A represented by the formula (2-1B) is preferably an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. It may be.

R ^B 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, a cycloalkyl group or an aryl group, and a hydrogen atom or an alkyl group. Is more preferable, and a hydrogen atom is particularly preferable, and these groups may have a substituent.

L ^C is preferably —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, more preferably —C (R ^B ) ₂ — or an arylene group, and an arylene group. It is further more preferable, and it is especially preferable that it is group represented by a formula (A-1) or (A-2), and these groups may have a substituent.

Examples and preferred ranges of the arylene group and divalent heterocyclic group represented by L ^C are the same as the examples and preferred ranges of the arylene group and divalent heterocyclic group represented by Ar ^Y1 , respectively.

Examples and preferred ranges of the substituents that R ^A , R ^B and L ^C may have are the same as examples and preferred ranges of the substituents which the group represented by Ar ^Y1 may have, respectively. .

n ^c1 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably 0. .

  When the polymer compound of the layer B is a polymer compound containing a structural unit represented by the formula (2-1B), the structural unit represented by the formula (2-1B) is a terminal structural unit.

  The “terminal structural unit” means a terminal structural unit of the polymer compound, and the terminal structural unit is preferably a structural unit derived from a terminal blocking agent in the production of the polymer compound. .

M ^1B is more preferably a group represented by the formula (BM-1).

Where
M ² , E ⁴ , ring L ¹ , ring L ² and A ³ -G ² -A ⁴ represent the same meaning as described above.
Ring L ¹¹ represents a 6-membered aromatic heterocyclic ring, and these rings may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
Ring L ¹² 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 the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
However, one of the ring L ¹¹ and the ring L ¹² has one bond.
n ¹¹ and ^{n 12} each independently represent an integer of 0 or more. However, n ¹¹ + n ¹² is 1 or 2. When M ² is a rhodium atom or an iridium atom, n ¹¹ + n ¹² is 2, and when M ² is a palladium atom or a platinum atom, n ¹¹ + n ¹² is 1.

When M ² is a rhodium atom or an iridium atom, n ¹¹ is more preferably 2.

When M ² is a palladium atom or a platinum atom, n ¹¹ is preferably 1.

When ring L ¹¹ does not have a bond, the definition, examples and preferred ranges of ring L ¹¹ are the same as the definitions, examples and preferred ranges of ring L ¹ described above.

When ring L ¹¹ has a bond, the definition, examples and preferred ranges of the ring portion excluding the bond of ring L ¹¹ are the same as the definition, examples and preferred ranges of ring L ¹ described above.

When ring L ¹² does not have a bond, the definition, examples and preferred ranges of ring L ¹² are the same as the definitions, examples and preferred ranges of ring L ² described above.

When ring L ¹² has a bond, the definition, examples and preferred ranges of the ring portion excluding the bond of ring L ¹² are the same as the definition, examples and preferred ranges of ring L ² described above.

The definitions, examples and preferred ranges of the substituents that the ring L ¹¹ and the ring L ¹² may have are the same as the definitions, examples and the preferred ranges of the substituents which the ring L ¹ and the ring L ² may have. It is.

[Structural Unit Represented by Formula (2-2B)]
L ^d is preferably —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, more preferably an arylene group or a divalent heterocyclic group, and an arylene group. Further preferred is a group represented by the formula (A-1) or (A-2), and these groups optionally have a substituent.

^Le is preferably —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, more preferably —C (R ^B ) ₂ — or an arylene group, and an arylene group. It is further more preferable, and it is especially preferable that it is group represented by a formula (A-1) or (A-2), and these groups may have a substituent.

Examples of the arylene group and divalent heterocyclic group represented by L ^d and L ^e and preferred ranges are respectively the same as the examples and preferred ranges of the arylene group and divalent heterocyclic group represented by Ar ^Y1 is there.

n ^d1 and n ^e1 are usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, still more preferably 0 or 1, particularly preferably. 0.

Ar ^1M is a benzene ring, a naphthalene ring, a fluorene ring, a phenanthrene ring, a dihydrophenanthrene ring, a pyridine ring, a diazabenzene ring, a triazine ring, a carbazole ring, a phenoxazine ring, or a phenothiazine ring. The group is preferably a group in which three hydrogen atoms directly bonded are removed, and three hydrogen atoms directly bonded to carbon atoms constituting the ring are excluded from a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring or dihydrophenanthrene ring. More preferably a group obtained by removing three hydrogen atoms directly bonded to the carbon atoms constituting the ring from the benzene ring or fluorene ring, and the carbon constituting the ring from the benzene ring. Particularly preferred is a group excluding three hydrogen atoms directly bonded to the atom. Preferably, these groups may have a substituent.

Examples and preferred ranges of the substituents that L ^d , ^Le and Ar ^1M may have are the same as the examples and preferred ranges of the substituents which the group represented by Ar ^Y1 may have, respectively. It is.

[Structural Unit Represented by Formula (2-3B)]
M ^2B is more preferably a group represented by the formula (BM-2) or (BM-3), and even more preferably a group represented by the formula (BM-2).

Where
M ² , E ⁴ , ring L ¹ , ring L ² , ring L ¹¹ , ring L ¹² and A ³ -G ² -A ⁴ represent the same meaning as described above. A plurality of the rings L ¹¹ may be the same or different. A plurality of the rings L ¹² may be the same or different.
n ¹³ and ^{n 14} each independently represent an integer of 0 or more. However, n ¹³ + n ¹⁴ is 0 or 1. When M ² is a rhodium atom or an iridium atom, n ¹³ + n ¹⁴ is 1, and when M ² is a palladium atom or a platinum atom, n ¹³ + n ¹⁴ is 0.

When M ² is a rhodium atom or an iridium atom, n ¹³ is preferably 1.

Where
M ² , E ⁴ , ring L ¹ , ring L ² , A ³ -G ² -A ⁴ , n ¹¹ and n ¹² represent the same meaning as described above.
Ring L ¹³ represents a 6-membered aromatic heterocyclic ring, and these rings optionally have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
Ring L ¹⁴ represents an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and these rings optionally have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded.
However, one of the ring L ¹³ and the ring L ¹⁴ has two bonds, or each of the ring L ¹³ and the ring L ¹⁴ has one bond.

When ring L ¹³ does not have a bond, the definition, examples and preferred ranges of ring L ¹³ are the same as the definitions, examples and preferred ranges of ring L ¹ .

When ring L ¹³ has a bond, the definition, examples and preferred ranges of the ring portion excluding the bond of ring L ¹³ are the same as the definition, example and preferred range of ring L ¹ .

When ring L ¹⁴ does not have a bond, the definition, examples and preferred ranges of ring L ¹⁴ are the same as the definition, examples and preferred ranges of ring L ² .

When ring L ¹⁴ has a bond, the definition, examples and preferred ranges of the ring portion excluding the bond of ring L ¹⁴ are the same as the definition, example and preferred range of ring L ² .

Definitions, examples and preferred ranges of the substituents that the ring L ¹³ and the ring L ¹⁴ may have are the same as the definitions, examples and preferred ranges of the substituents which the ring L ¹ and the ring L ² may have. It is.

Each of the ring L ¹³ and the ring L ¹⁴ preferably has one bond.

[Structural Unit Represented by Formula (2-4B)]
M ^3B is preferably a group represented by the formula (BM-4).

Where
M ² , E ⁴ , Ring L ¹¹ , Ring L ¹² , Ring L ¹³ and Ring L ¹⁴ represent the same meaning as described above.
n ¹⁵ represents 0 or 1. n ¹⁶ represents 1 or 3. However, when M ² is a rhodium atom or an iridium atom, n ¹⁵ is 0 and n ¹⁶ is 3. When M ² is a palladium atom or a platinum atom, n ¹⁵ is 1 and n ¹⁶ is 1.

  Examples of the metal complex constituent unit include formulas (1G-1) to (1G-13), (2G-1) to (2G-16), (3G-1) to (3G-23) or (4G-1). ) To (4G-6).

Where
^RD represents the same meaning as described above.
De represents a group represented by the formula (D-A), (D-B) or (D-C).

  Since the metal complex constituent unit is excellent in the external quantum efficiency of the light emitting device of the present embodiment, it is preferably 0.01 to 50 mol% with respect to the total amount of constituent units contained in the polymer compound of layer B, More preferably, it is 0.1-30 mol%, More preferably, it is 0.5-10 mol%, Most preferably, it is 1-5 mol%. One type of metal complex structural unit may be contained in the polymer compound of layer B, or two or more types may be contained.

The polymer compound of the layer B can form the light-emitting element of this embodiment by a wet method, and the light-emitting element can be stacked. Therefore, a polymer compound containing a metal complex constituent unit and a constituent unit having a crosslinking group (hereinafter, It is also preferably referred to as “polymer compound of layer B ′”.
That is, it is preferable that the cross-linked product of the polymer compound in the layer B is a cross-linked product of the polymer compound in the layer B ′.

  The metal complex constituent unit is preferably 0.01 to 50 mol% with respect to the total amount of constituent units contained in the polymer compound of the layer B ′ because the external quantum efficiency of the light emitting device of the present embodiment is excellent. More preferably, it is 0.1-30 mol%, More preferably, it is 0.5-10 mol%, Most preferably, it is 1-5 mol%. One type of metal complex structural unit may be contained in the polymer compound of the layer B ′, or two or more types may be contained.

  Since the structural unit having a crosslinking group is excellent in stability and crosslinkability of the polymer compound in the layer B ′, it is preferably 0.5 to It is 80 mol%, More preferably, it is 3-65 mol%, More preferably, it is 5-50 mol%. One type of structural unit having a crosslinking group may be contained in the polymer compound of the layer B ′, or two or more types may be contained.

  Since the polymer compound of the layer B is excellent in hole transportability, it is preferable that the polymer compound further includes a structural unit represented by the formula (X). Since the polymer compound of the layer B ′ has excellent hole transport properties, it is preferable that the polymer compound further includes a structural unit represented by the formula (X).

  The definition, examples, and preferred ranges of the structural unit represented by the formula (X) that may be contained in the polymer compound in the layer B and the polymer compound in the layer B ′ may be contained in the polymer host described above. The definition, examples, and preferred ranges of the structural unit represented by formula (X) are the same.

  When the polymer compound of the layer B includes a structural unit represented by the formula (X), the structural unit represented by the formula (X) contained in the polymer compound of the layer B has a higher hole transport property. , Preferably 1 to 90 mol%, more preferably 10 to 70 mol%, still more preferably 30 to 50 mol%, based on the total amount of structural units contained in the polymer compound of layer B. . When the polymer compound of the layer B ′ contains a structural unit represented by the formula (X), the structural unit represented by the formula (X) contained in the polymer compound of the layer B ′ has more hole transportability. Since it is excellent, it is preferably 1 to 90 mol%, more preferably 10 to 70 mol%, still more preferably 30 to 50 mol based on the total amount of structural units contained in the polymer compound of the layer B ′. %.

  One type of structural unit represented by the formula (X) may be contained in the polymer compound of the layer B, or two or more types may be contained. One type of structural unit represented by the formula (X) may be contained in the polymer compound of the layer B ′, or two or more types may be contained.

  Since the high molecular compound of the layer B is excellent in the external quantum efficiency of the light emitting device of this embodiment, the layer B preferably further includes a structural unit represented by the formula (Y). The polymer compound of the layer B ′ preferably further includes a structural unit represented by the formula (Y) because the external quantum efficiency of the light emitting device of this embodiment is excellent.

  The definition, examples, and preferred ranges of the structural unit represented by the formula (Y) that may be contained in the polymer compound in the layer B and the polymer compound in the layer B ′ may be contained in the polymer host described above. The definition, examples, and preferred ranges of the structural unit represented by the formula (Y) are the same.

When the polymer compound of the layer B includes a structural unit represented by the formula (Y) and Ar ^Y1 is an arylene group, the structural unit represented by the formula (Y) contained in the polymer compound of the layer B is Since the luminance lifetime of the light emitting device of this embodiment is more excellent, it is preferably 0.5 to 90 mol%, more preferably 30 to 80, based on the total amount of structural units contained in the polymer compound of layer B. Mol%.
When the polymer compound of the layer B ′ includes a structural unit represented by the formula (Y) and Ar ^Y1 is an arylene group, the structural unit represented by the formula (Y) contained in the polymer compound of the layer B ′ Since the luminance lifetime of the light emitting device of this embodiment is more excellent, it is preferably 0.5 to 90 mol%, more preferably based on the total amount of structural units contained in the polymer compound of the layer B ′. 30 to 80 mol%.

The polymer compound of the layer B includes a structural unit represented by the formula (Y), and Ar ^Y1 is a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded. The structural unit represented by the formula (Y) contained in the polymer compound of the layer B is more excellent in the charge transport property of the light-emitting device of the present embodiment, and therefore the composition contained in the polymer compound of the layer B. Preferably it is 0.5-50 mol% with respect to the total amount of a unit, More preferably, it is 3-30 mol%.
The polymer compound of the layer B ′ contains a structural unit represented by the formula (Y), and Ar ^Y1 is a divalent heterocyclic group or a divalent heterocyclic group in which an arylene group and a divalent heterocyclic group are directly bonded. In the case of the group, the structural unit represented by the formula (Y) contained in the polymer compound of the layer B ′ is more excellent in the charge transporting property of the light emitting device of the present embodiment. Preferably it is 0.5-50 mol% with respect to the total amount of the structural unit contained, More preferably, it is 3-30 mol%.

  One type of structural unit represented by the formula (Y) may be contained in the polymer compound of the layer B, or two or more types may be contained. One type of structural unit represented by the formula (Y) may be contained in the polymer compound of the layer B ′, or two or more types may be contained.

[Structural unit having a crosslinking group]
In the structural unit having a crosslinkable group, the crosslinkable group is preferably a crosslinkable group selected from the crosslinkable group A group because the external quantum efficiency of the light emitting device of this embodiment is excellent.

  As the bridging group selected from the bridging group A group, since the external quantum efficiency of the light emitting device of this embodiment is more excellent, the formula (XL-1) to the formula (XL-4) and the formula (XL-7) are preferable. To a crosslinking group represented by Formula (XL-10) or Formula (XL-14) to Formula (XL-17), and more preferably Formula (XL-1), Formula (XL-3), Formula ( XL-9), a formula (XL-10), a formula (XL-16), or a crosslinking group represented by a formula (XL-17), more preferably a formula (XL-1) or a formula (XL-16). Or a crosslinking group represented by formula (XL-17), particularly preferably a crosslinking group represented by formula (XL-1) or (XL-17), and particularly preferred is formula (XL). -17).

  As the cross-linking group selected from the cross-linking group A group, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, and the cross-linking property of the polymer compound of the layer B ′ is more preferable. 2) to the formula (XL-4), the formula (XL-7) to the formula (XL-10), the formula (XL-14), the formula (XL-15) or the crosslinking group represented by the formula (XL-17) And more preferably a crosslinking group represented by formula (XL-9), formula (XL-10) or formula (XL-17), particularly preferably represented by formula (XL-17). It is a crosslinking group.

  The structural unit having at least one crosslinking group selected from the crosslinking group A group in the polymer compound of the layer B ′ is a structural unit represented by the formula (Z) or a structural unit represented by the formula (Z ′). The structural unit is preferably a structural unit represented by the formula (Z), but may be a structural unit represented by the following formula.

  When the polymer compound of layer B ′ contains two or more structural units having at least one crosslinking group selected from the crosslinking group A group, the structural unit having at least one crosslinking group selected from the crosslinking group A group It is preferable that at least two of these have different crosslinking groups. Examples of combinations of different crosslinking groups include Formula (XL-1), Formula (XL-2), Formula (XL-5) to Formula (XL-8), or Formula (XL-14) to Formula (XL-16). A combination of the crosslinking group represented by formula (XL-3), formula (XL-4), formula (XL-13) or formula (XL-17) is preferred, and the formula (XL -1) or a crosslinkable group represented by formula (XL-16) and a crosslinkable group represented by formula (XL-17) are more preferred, and a crosslinkable group represented by formula (XL-1) And a combination with a crosslinking group represented by the formula (XL-17) is more preferred.

-The structural unit represented by the formula (Z)

Where
nA represents an integer of 0 to 5, and n represents 1 or 2. When a plurality of nA are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good. R ′ 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 a plurality of ^LA are present, they may be the same or different.
X represents a crosslinking group selected from the crosslinking group A group. When two or more X exists, they may be the same or different.

  nA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 1, since the external quantum efficiency of the light emitting device of the present embodiment is more excellent.

  n is preferably 2 because the external quantum efficiency of the light emitting device of this embodiment is more excellent.

Ar ³ is preferably an aromatic hydrocarbon group which may have a substituent since the external quantum efficiency of the light emitting device of this embodiment is more excellent.

The number of carbon atoms of the aromatic hydrocarbon group represented by Ar ³ is usually 6 to 60, preferably 6 to 30 and more preferably 6 to 18 without including the number of carbon atoms of the substituent. is there.
The arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar ³ is preferably a group represented by the formula (A-1) to the formula (A-20), More preferably, groups represented by formula (A-1), formula (A-2), formula (A-6) to formula (A-10), formula (A-19) or formula (A-20) And more preferably a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), This group may have a substituent.

The number of carbon atoms of the heterocyclic group represented by Ar ³ is usually 2 to 60, preferably 3 to 30 and more preferably 4 to 18 without including the number of carbon atoms of the substituent.
The divalent heterocyclic group part excluding n substituents of the heterocyclic group represented by Ar ³ is preferably a group represented by the formula (AA-1) to the formula (AA-34). is there.

The aromatic hydrocarbon group and heterocyclic group represented by Ar ³ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group. Group, halogen atom, monovalent heterocyclic group and cyano group are preferred.

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

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

Arylene group represented by L ^A may have a substituent. As the arylene group, a phenylene group or a fluorenediyl group is preferable, and an m-phenylene group, a p-phenylene group, a fluorene-2,7-diyl group, or a fluorene-9,9-diyl group is more preferable. Examples of the substituent that the arylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, or a bridging group A. A crosslinking group selected from the group is preferred, and these groups may further have a substituent.

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

L ^A, since it is easy to manufacture the polymer compound layers B ', preferably, an arylene group or an alkylene group, more preferably a phenylene group, fluorenediyl group or an alkylene group, these groups May have a substituent.

  As the bridging group represented by X, the external quantum efficiency of the light-emitting device of the present embodiment is more excellent. Therefore, the formula (XL-1) to the formula (XL-4) and the formula (XL-7) to the formula are preferable. (XL-10) or a crosslinking group represented by the formula (XL-14) to the formula (XL-17), more preferably the formula (XL-1), the formula (XL-3), the formula (XL- 9), a crosslinking group represented by formula (XL-10), formula (XL-16) or formula (XL-17), more preferably formula (XL-1), formula (XL-16) or A crosslinking group represented by the formula (XL-17), particularly preferably a crosslinking group represented by the formula (XL-1) or the formula (XL-17), and particularly preferably a formula (XL-17). ).

  As the cross-linking group represented by X, the external quantum efficiency of the light-emitting device of the present embodiment is more excellent, and the cross-linkability of the polymer compound of the layer B ′ is more preferable. Therefore, the formula (XL-2) is preferable. A crosslinking group represented by formula (XL-4), formula (XL-7) to formula (XL-10), formula (XL-14), formula (XL-15) or formula (XL-17). More preferably, it is a crosslinking group represented by formula (XL-9), formula (XL-10) or formula (XL-17), and particularly preferred is a crosslinking group represented by formula (XL-17). It is.

Since the structural unit represented by the formula (Z) is excellent in the stability and crosslinkability of the polymer compound in the layer B ′, It is 0.5-80 mol%, More preferably, it is 3-65 mol%, More preferably, it is 5-50 mol%.
One type of structural unit represented by the formula (Z) may be contained in the polymer compound of the layer B ′, or two or more types may be contained.

  When the polymer compound of the layer B ′ includes two or more structural units represented by the formula (Z), at least two structural units represented by the formula (Z) have a crosslinking group represented by X. Preferably they are different from each other. The preferable range of the combination of the crosslinking groups represented by different X is the same as the preferable range of the combination of the different crosslinking groups described above.

  A structural unit represented by the formula (Z ′)

Where
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. When a plurality of mA are present, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ⁴ , Ar ^5, and Ar ⁶ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring by bonding directly or through an oxygen atom or sulfur atom. You may do it.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good. R ′ 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 a plurality of K ^A are present, they may be the same or different.
X ′ represents a bridging group selected from the bridging group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. When a plurality of X ′ are present, they may be the same or different. However, at least one X ′ is a crosslinking group selected from the crosslinking group A group.

  mA is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, particularly preferably because the external quantum efficiency of the light emitting device of this embodiment is more excellent. Is 0.

  m is preferably 1 or 2 and more preferably 2 because the external quantum efficiency of the light emitting device of the present embodiment is more excellent.

  “c” is preferably 0 because the polymer compound of the layer B ′ can be easily produced and the external quantum efficiency of the light emitting device of this embodiment is more excellent.

Ar ⁵ is preferably an aromatic hydrocarbon group which may have a substituent since the external quantum efficiency of the light emitting device of this embodiment is more excellent.

The definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar ⁵ are the same as the definition and example of the arylene group represented by Ar ^X2 in formula (X). .

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

The definition and example of the divalent group excluding m substituents of the group in which the aromatic hydrocarbon ring represented by Ar ⁵ and the heterocyclic ring are directly bonded are represented by Ar ^X2 in the formula (X). This is the same as the definition and examples of a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded.

Ar ⁴ and Ar ⁶ are preferably an arylene group which may have a substituent since the external quantum efficiency of the light emitting device of this embodiment is more excellent.

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

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

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

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

K ^A, because it is easy to manufacture the polymer compound layers B ', is preferably a phenylene group or a methylene group.

  The definition and example of the crosslinking group represented by X ′ are the same as the definition and example of the crosslinking group represented by X.

  The structural unit represented by the formula (Z ′) is excellent in the stability of the polymer compound in the layer B ′ and the crosslinkability of the polymer compound in the layer B ′. Preferably it is 0.5-50 mol% with respect to the total amount of the structural unit contained, More preferably, it is 3-30 mol%, More preferably, it is 5-20 mol%. One type of structural unit represented by the formula (Z ′) may be included in the polymer compound of the layer B ′, or two or more types may be included.

  When the polymer compound of the layer B ′ contains two or more structural units represented by the formula (Z ′), at least two structural units represented by the formula (Z ′) are represented by X ′. It is preferred that the crosslinking groups are different from each other. The preferable range of the combination of different crosslinking groups represented by X ′ is the same as the preferable range of the combination of different crosslinking groups described above.

-Preferred embodiment of the structural unit represented by formula (Z) or (Z ') Examples of the structural unit represented by formula (Z) are those represented by formula (Z-1) to formula (Z-30). Examples of the structural unit represented by the formula (Z ′) include structural units represented by the formula (Z′-1) to the formula (Z′-9). Among these, since the crosslinkability of the polymer compound of the layer B ′ is excellent, it is preferably a structural unit represented by the formula (Z-1) to the formula (Z-30), more preferably the formula (Z-1). ) To (Z-15), (Z-19), (Z-20), (Z-23), (Z-25) or (Z-30). And more preferably a structural unit represented by formula (Z-1) to formula (Z-9) or formula (Z-30).

  Examples of the polymer compound in the layer B and the polymer compound in the layer B ′ include polymer compounds P-15 to P-29. Here, the “other” structural unit refers to a structural unit other than a structural unit having a metal complex, a structural unit having a crosslinking group, a structural unit represented by the formula (X), and a structural unit represented by the formula (Y). means.

  In the table, p "", q "", r "", s "", t "" and u "" represent the molar ratio of each constituent unit. p ″ ′ + q ′ ″ + r ′ ″ + s ′ ″ + t ′ ″ + u ′ ″ = 100 and 70 ≦ p ′ ″ + q ′ ″ + r ′ ″ + s ′ ″ + t '' '≦ 100.

  The polymer compound in the layer B and the polymer compound in the layer B ′ may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, respectively. Although it may be, it is preferable that it is a copolymer formed by copolymerizing plural kinds of raw material monomers.

The number average molecular weight in terms of polystyrene of the polymer compound in layer B and the polymer compound in layer B ′ is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ^{4 to} 5 × 10 ⁵ . Yes, more preferably 1.5 × 10 ⁴ to 1 × 10 ⁵ .

-Manufacturing method of polymer compound of layer B and polymer compound of layer B 'The polymer compound of layer B and the polymer compound of layer B' should be manufactured by the same method as the manufacturing method of the polymer host described above. Can do. As production methods other than the above, for example, Japanese Patent Application Laid-Open No. 2003-171659, International Publication No. 2006/003000, Japanese Patent Application Laid-Open No. 2010-43243, Japanese Patent Application Laid-Open No. 2011-105701, International Publication No. 2013/021180, It can be synthesized according to the methods described in Japanese Unexamined Patent Application Publication No. 2015-174931 and Japanese Unexamined Patent Application Publication No. 2015-174932.

-Composition of layer B and composition of layer B 'Layer B is composed of the polymer compound of layer B (or a crosslinked product thereof), a hole transport material, a hole injection material, an electron transport material, an electron injection material, and light emission. It may be a layer containing a composition containing at least one material selected from the group consisting of a material and an antioxidant (hereinafter also referred to as “the composition of layer B”).
The layer B is at least selected from the group consisting of the polymer compound of the layer B ′ (or a crosslinked product thereof), a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. It may be a layer containing a composition containing one kind of material (hereinafter also referred to as “the composition of layer B ′”).

  Examples and preferred ranges of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material contained in the composition of layer B and the composition of layer B ′ are contained in the first composition. Examples of the hole transporting material, electron transporting material, hole injecting material, electron injecting material, and light emitting material to be used are the same as the preferred range. In the composition of layer B, the content of the hole transport material, electron transport material, hole injection material, electron injection material, and light emitting material is 100 parts by mass of the polymer compound of layer B (or a crosslinked product thereof). In general, it is 1 to 1000 parts by mass, preferably 5 to 500 parts by mass. In the composition of the layer B ′, the contents of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material are respectively 100% of the polymer compound (or a crosslinked product thereof) of the layer B ′. When it is set as a mass part, it is 1-1000 mass parts normally, Preferably it is 5-500 mass parts.

  Examples and preferred ranges of the antioxidant contained in the composition of the layer B and the composition of the layer B ′ are the same as those of the antioxidant and the preferred range contained in the first composition. In the composition of layer B, the content of the antioxidant is usually 0.001 to 10 parts by mass when the polymer compound of layer B (or a crosslinked product thereof) is 100 parts by mass. In the composition of the layer B ′, the content of the antioxidant is usually 0.001 to 10 parts by mass when the polymer compound (or a crosslinked product thereof) of the layer B ′ is 100 parts by mass.

Layer B ink and layer B ′ ink Layer B is, for example, a composition containing the polymer compound of layer B and a solvent (hereinafter also referred to as “ink of layer B”) or layer B. It can be formed using a composition containing a polymer compound of 'and a solvent (hereinafter also referred to as “ink of layer B”). The ink of the layer B and the ink of the layer B ′ can be suitably used for the wet method described in the section of the first ink. The preferable range of the viscosity of the ink of the layer B and the ink of the layer B ′ is the same as the preferable range of the viscosity of the first ink. Examples and preferred ranges of the solvent contained in the ink of the layer B and the ink of the layer B ′ are the same as those of the solvent contained in the first ink.

  In the ink of layer B, the content of the solvent is usually 1000 to 100000 parts by mass, preferably 2000 to 20000 parts by mass, when the polymer compound of layer B is 100 parts by mass. In the ink of the layer B ′, the content of the solvent is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass when the polymer compound of the layer B ′ is 100 parts by mass.

<Layer C>
Next, the layer C which is one of the preferred embodiments of the second organic layer will be described.

Layer C is a layer containing a metal complex represented by Formula (2). In the layer C, the metal complex represented by the formula (2) may be contained singly or in combination of two or more.
The layer C is preferably a layer C ′ containing a metal complex represented by the formula (2) and a crosslinked product of a compound having a crosslinking group. In the layer C ′, the metal complex represented by the formula (2) and the crosslinked product of the compound having a crosslinking group may be contained singly or in combination of two or more.

  Examples of the compound having a crosslinkable group include a low molecular compound having a crosslinkable group and a polymer compound containing a structural unit having a crosslinkable group, and the external quantum efficiency of the light emitting device of this embodiment is more excellent. A low molecular compound having at least one crosslinking group selected from Group A (hereinafter, also referred to as “low molecular compound of layer C ′”), or at least one crosslinking group selected from Group A. A polymer compound containing a structural unit (hereinafter also referred to as “polymer compound of layer C ′”) is preferable, and a polymer compound of layer C ′ is more preferable. The polymer compound in the layer B ′ is different from the polymer compound in the layer C ′. That is, the polymer compound of the layer C ′ is a polymer compound that does not contain a metal complex structural unit.

  Examples and preferred ranges of the crosslinking group in the compound having a crosslinking group are the same as examples and preferred ranges of the crosslinking group in the structural unit having the crosslinking group.

[Polymer compound of layer C ′]
The definition, examples, and preferred ranges of the structural unit having at least one crosslinking group selected from the crosslinking group A group in the polymer compound of the layer C ′ are at least selected from the crosslinking group A group in the polymer compound of the layer B ′. The definition, examples, and preferred ranges of the structural unit having one type of crosslinking group are the same.

  The constitutional unit having at least one kind of crosslinking group selected from the crosslinking group A group is excellent in stability and crosslinkability of the polymer compound in the layer C ′, and therefore the total of the constitutional units contained in the polymer compound in the layer C ′. Preferably it is 0.5-80 mol% with respect to quantity, More preferably, it is 3-65 mol%, More preferably, it is 5-50 mol%.

  One type of structural unit having at least one type of cross-linking group selected from the cross-linking group A group may be contained in the polymer compound of the layer C ′, or two or more types may be contained.

  In the polymer compound of the layer C ′, the structural unit having at least one crosslinking group selected from the crosslinking group A group is preferably represented by the structural unit represented by the formula (Z) or the formula (Z ′). And more preferably a structural unit represented by the formula (Z).

  When the polymer compound of the layer C ′ includes a structural unit represented by the formula (Z), the structural unit represented by the formula (Z) is excellent in stability and crosslinkability of the polymer compound of the layer C ′. , Preferably 0.5 to 80 mol%, more preferably 3 to 65 mol%, still more preferably 5 to 50 mol, based on the total amount of structural units contained in the polymer compound of layer C ′. %. One type of structural unit represented by the formula (Z) may be contained in the polymer compound of the layer C ′, or two or more types may be contained.

  When the polymer compound of the layer C ′ includes a structural unit represented by the formula (Z ′), the structural unit represented by the formula (Z ′) has excellent stability of the polymer compound of the layer C ′, and The cross-linking property of the polymer compound in the layer C ′ is excellent, so that it is preferably 0.5 to 50 mol%, more preferably 3%, based on the total amount of the structural units contained in the polymer compound in the layer C ′. It is -30 mol%, More preferably, it is 5-20 mol%. One type of structural unit represented by the formula (Z ′) may be included in the polymer compound of the layer C ′, or two or more types may be included.

  Since the polymer compound in the layer C ′ is excellent in hole transportability, it is preferable that the polymer compound further includes a structural unit represented by the formula (X). The definition, examples, and preferred ranges of the structural unit represented by the formula (X) that may be contained in the polymer compound of the layer C ′ are represented by the formula (X) that may be contained in the aforementioned polymer host. This is the same as the definition, examples and preferred ranges of structural units.

  When the polymer compound of the layer C ′ contains a structural unit represented by the formula (X), the structural unit represented by the formula (X) contained in the polymer compound of the layer C ′ has more hole transport properties. Since it is excellent, it is preferably 1 to 90 mol%, more preferably 10 to 70 mol%, still more preferably 30 to 50 mol, based on the total amount of structural units contained in the polymer compound of the layer C ′. %. One type of structural unit represented by the formula (X) may be included in the polymer compound of the layer C ′, or two or more types may be included.

  Since the polymer compound of the layer C ′ is excellent in the external quantum efficiency of the light emitting device of this embodiment, it is preferable that the polymer compound further includes a structural unit represented by the formula (Y). The definition, examples, and preferred ranges of the structural unit represented by the formula (Y) that the polymer compound of the layer C ′ may contain are represented by the formula (Y) that the polymer host described above may contain. This is the same as the definition, examples and preferred ranges of structural units.

When the polymer compound of the layer C ′ includes a structural unit represented by the formula (Y) and Ar ^Y1 is an arylene group, the structural unit represented by the formula (Y) contained in the polymer compound of the layer C ′ Since the external quantum efficiency of the light emitting device of this embodiment is more excellent, it is preferably 0.5 to 90 mol%, more preferably, based on the total amount of structural units contained in the polymer compound of the layer C ′. Is 30 to 80 mol%. The polymer compound of the layer C ′ contains a structural unit represented by the formula (Y), and Ar ^Y1 is a divalent heterocyclic group, or a divalent heterocyclic group in which an arylene group and a divalent heterocyclic group are directly bonded. In the case of the group, the structural unit represented by the formula (Y) contained in the polymer compound of the layer C ′ is more excellent in the charge transport property of the light emitting device of the present embodiment. Preferably it is 0.5-50 mol% with respect to the total amount of the structural unit contained, More preferably, it is 3-30 mol%.

  One type of structural unit represented by the formula (Y) may be included in the polymer compound of the layer C ′, or two or more types may be included.

  Examples of the polymer compound of the layer C ′ include polymer compounds P-7 to P-14. Here, the “other” structural unit means a structural unit other than the structural unit having a crosslinking group and the structural units represented by the formula (X) and the formula (Y).

  In the table, p ′, q ′, r ′, s ′, and t ′ represent the molar ratio of each structural unit. p ′ + q ′ + r ′ + s ′ + t ′ = 100 and 70 ≦ p ′ + q ′ + r ′ + s ′ ≦ 100.

  The polymer compound of the layer C ′ may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A copolymer obtained by copolymerizing raw material monomers is preferred.

The number average molecular weight in terms of polystyrene of the polymer compound of the layer C ′ is preferably 5 × 10 ³ to 1 × 10 ⁶ , more preferably 1 × 10 ^{4 to} 5 × 10 ⁵ , more preferably 1. It is 5 * 10 < ⁴ > -1 * 10 < ⁵ >.

-Manufacturing method of polymer compound of layer C 'The polymer compound of layer C' can be manufactured by the method similar to the manufacturing method of the above-mentioned polymer host.

[Low molecular compound of layer C ′]
The low molecular compound of the layer C ′ is preferably a low molecular compound represented by the formula (3).

Where
m ^B1 , m ^B2 and m ^B3 each independently represent an integer of 0 or more. A plurality of m ^B1 may be the same or different. When a plurality of m ^B3 are present, they may be the same or different.
Ar ⁷ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent. When a plurality of Ar ⁷ are present, they may be the same or different.
L ^B1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by —N (R ′ ″) —, an oxygen atom or a sulfur atom, and these groups are substituents. You may have. R ′ ″ 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 a plurality of L ^B1 are present, they may be the same or different.
X ″ represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of X ″ may be the same or different. However, at least one of a plurality of X ″ is a crosslinking group.

m ^B1 is usually an integer of 0 to 10, and is preferably an integer of 0 to 5, more preferably an integer of 0 to 2, because it facilitates the synthesis of the low molecular weight compound in the layer C ′. More preferably, it is 0 or 1, and particularly preferably 0.

m ^B2 is usually an integer of 0 to 10, and it is easy to synthesize a low molecular compound of the layer C ′, and the external quantum efficiency of the light emitting device of the present embodiment is more excellent. It is an integer, more preferably an integer of 0 to 3, further preferably 1 or 2, and particularly preferably 1.

m ^B3 is generally an integer of 0 to 5, and is preferably an integer of 0 to 4, more preferably an integer of 0 to 2, because the synthesis of the low molecular compound of the layer C ′ is facilitated. More preferably, it is 0.

The definition and examples of the arylene group part excluding m ^B3 substituents of the aromatic hydrocarbon group represented by Ar ⁷ are the same as the definitions and examples of the arylene group represented by Ar ^X2 in formula (X). is there.

The definition and example of the divalent heterocyclic group part excluding m ^B3 substituents of the heterocyclic group represented by Ar ⁷ are the divalent heterocyclic group part represented by Ar ^X2 in formula (X) The same as the definitions and examples.

The definition and example of a divalent group excluding m ^B3 substituents of a group in which an aromatic hydrocarbon ring and a heterocycle represented by Ar ⁷ are directly bonded are represented by Ar ^X2 in formula (X). This is the same as the definition and examples of the divalent group in which the arylene group and the divalent heterocyclic group are directly bonded.

The definition and example of the substituent that the group represented by Ar ⁷ may have are the same as the definition and example of the substituent that the group represented by Ar ^X2 in formula (X) may have.

Ar ⁷ is preferably an aromatic hydrocarbon group because the external quantum efficiency of the light emitting device of this embodiment is more excellent, and this aromatic hydrocarbon group may have a substituent.

Alkylene group represented by L ^B1, a cycloalkylene group, an arylene group, a divalent definitions and examples of the heterocyclic group, respectively, the alkylene group represented by L ^A, a cycloalkylene group, an arylene group, a divalent heterocyclic The definition and examples of the ring group are the same.

L ^B1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably an alkylene group or an arylene group, still more preferably a phenylene group, because synthesis of the low molecular compound of the layer C ′ is facilitated. A fluorenediyl group or an alkylene group, particularly preferably a phenylene group or an alkylene group, and these groups optionally have a substituent.

  X ″ is preferably a bridging group, an aryl group or a monovalent heterocyclic group represented by any one of the formulas (XL-1) to (XL-17), more preferably the formula (XL). -1), a formula (XL-3), a formula (XL-7) to a formula (XL-10), a formula (XL-16) or a crosslinkable group represented by the formula (XL-17), or an aryl group And more preferably a crosslinking group, a phenyl group, a naphthyl group or a fluorenyl group represented by the formula (XL-1), the formula (XL-16) or the formula (XL-17). XL-16) or a crosslinking group represented by formula (XL-17), a phenyl group or a naphthyl group, particularly preferably a crosslinking group represented by formula (XL-16) or a naphthyl group, These groups may have a substituent.

  Examples of the low molecular compound of the layer C ′ include low molecular compounds represented by formula (3-1) to formula (3-16), and preferably formula (3-1) to formula (3-10). ), And more preferably low molecular compounds represented by formula (3-5) to formula (3-9).

  The low molecular weight compound of layer C 'is described in Aldrich, Luminescence Technology Corp. Available from the American Dye Source. In addition, it is compoundable according to the method described in the international publication 1997/033193, the international publication 2005/035221, and the international publication 2005/049548, for example.

-Composition of layer C and composition of layer C 'Layer C comprises a metal complex represented by formula (2), a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and It may be a layer containing a composition containing at least one selected from the group consisting of antioxidants (hereinafter also referred to as “the composition of layer C”). However, the metal complex represented by the formula (2) is different from the hole transport material, the hole injection material, the electron transport material, the electron injection material, and the light emitting material.
Layer C ′ comprises a metal complex represented by formula (2), a crosslinked product of a compound having a crosslinking group, a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. It may be a layer containing a composition containing at least one selected from the group consisting of agents (hereinafter also referred to as “composition of layer C ′”). However, a crosslinked product of a compound having a metal complex and a crosslinking group represented by the formula (2) is different from a hole transport material, a hole injection material, an electron transport material, an electron injection material, and a light emitting material.

  Examples and preferred ranges of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light-emitting material contained in the composition of the layer C and the composition of the layer C ′ are the same as those in the first composition. Examples of the hole transport material, electron transport material, hole injection material, electron injection material, and light-emitting material to be contained are the same as the examples and preferred ranges. In the composition of layer C, the contents of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material were each 100 parts by mass of the metal complex represented by the formula (2). In this case, it is usually 1 to 1000 parts by mass, preferably 5 to 500 parts by mass. In the composition of the layer C ′, the contents of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light emitting material each have a metal complex represented by the formula (2) and a crosslinking group. When the total of the compound and the crosslinked product is 100 parts by mass, it is usually 1 to 1000 parts by mass, preferably 5 to 500 parts by mass.

  Examples and preferred ranges of the antioxidant contained in the composition of the layer C and the composition of the layer C ′ are the same as those of the antioxidant and the preferred range contained in the first composition. In the composition of layer C, the content of the antioxidant is usually 0.001 to 10 parts by mass when the metal complex represented by the formula (2) is 100 parts by mass. In the composition of layer C ′, the content of the antioxidant is usually 0. When the total of the metal complex represented by formula (2) and the crosslinked product of the compound having a crosslinking group is 100 parts by mass. 001 to 10 parts by mass.

Layer Ink and Layer C ′ Ink Layer C is, for example, a composition containing a metal complex represented by formula (2) and a solvent (hereinafter also referred to as “ink of layer C”). Can be formed. Layer C ′ uses, for example, a composition containing a metal complex represented by the formula (2), a compound having a crosslinking group, and a solvent (hereinafter also referred to as “ink of layer C ′”). Can be formed. The ink of the layer C and the ink of the layer C ′ can be suitably used for the wet method described in the section of the first ink. The preferable range of the viscosity of the ink of the layer C and the ink of the layer C ′ is the same as the preferable range of the viscosity of the first ink. Examples and preferred ranges of the solvent contained in the ink of the layer C and the ink of the layer C ′ are the same as the examples and preferred ranges of the solvent contained in the first ink.

  In the ink of layer C, the content of the solvent is usually 1000 to 100000 parts by mass, preferably 2000 to 20000 parts by mass, when the metal complex represented by the formula (2) is 100 parts by mass. In the ink of layer C ′, the content of the solvent is usually 1000 to 100000 parts by mass when the total of the metal complex represented by the formula (2) and the compound having a crosslinking group is 100 parts by mass. Preferably it is 2000-20000 mass parts.

<Layer structure of light emitting element>
The light emitting element of this embodiment may have layers other than an anode, a cathode, a 1st organic layer, and a 2nd organic layer.

In the light emitting device of this embodiment, the first organic layer and the second organic layer are preferably adjacent to each other because the external quantum efficiency of the light emitting device of this embodiment is more excellent.
In the light emitting device of this embodiment, the second organic layer is preferably a layer provided between the anode and the first organic layer because the external quantum efficiency of the light emitting device of this embodiment is more excellent.

In the light emitting device of the present embodiment, when the first organic layer is the layer A, the second organic layer is the layer B or the layer C ′, and the external quantum efficiency of the light emitting device of the present embodiment is more excellent. Layer B is preferred.
In the light emitting device of the present embodiment, when the first organic layer is the layer A ′, the second organic layer is the layer B or the layer C, and the external quantum efficiency of the light emitting device of the present embodiment is more excellent. Layer B or layer C ′ is preferable, and layer B is more preferable.

In the light emitting device of the present embodiment, the first organic layer is preferably a light emitting layer (hereinafter referred to as “first light emitting layer”).
In the light emitting device of the present embodiment, the second organic layer is usually a hole transport layer, a light emitting layer (that is, a light emitting layer separate from the first light emitting layer, hereinafter referred to as “second light emitting layer”). Or an electron transport layer, preferably a hole transport layer or a second light-emitting layer, and more preferably a second light-emitting layer.

  In the light emitting device of this embodiment, when the first organic layer is the first light emitting layer and the second organic layer is the second light emitting layer, the first organic layer is the layer A ′. Since the external quantum efficiency of the light emitting device of this embodiment is more excellent, it is preferable that the first organic layer is the layer A ′ and the second organic layer is the layer B or the layer C. More preferably, the organic layer is layer A ′, and the second organic layer is layer B or layer C ′, the first organic layer is layer A ′, and the second organic layer is More preferably, it is layer B.

In the light emitting device of this embodiment, when the first light emitting layer and the second light emitting layer are provided, the light emitting device is adjusted by adjusting the light emitting color of the first light emitting layer and the light emitting color of the second light emitting layer. The emission color can be adjusted, and the emission color can also be adjusted to white.
For example, when the first light emitting layer is the layer A and the second light emitting layer is the layer B, the content of the metal complex represented by the formula (1) in the layer A and the layer B in the layer B It is possible to adjust the emission color by adjusting the polymer compound or the content of the crosslinked polymer compound of layer B, and 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). The white luminescent color is, for example, in which the chromaticity coordinate X is in the range of 0.20 to 0.55 and the chromaticity coordinate Y is in the range of 0.20 to 0.55. It is preferable that the degree coordinate X is in the range of 0.25 to 0.50, and the chromaticity coordinate Y is in the range of 0.25 to 0.50.

  From the viewpoint of adjusting the emission color of the light emitting device of this embodiment (particularly adjusting the emission color to white), the emission spectrum of the light emitting device of this embodiment preferably has a maximum emission wavelength of 380 nm or more and less than 495 nm. More preferably, it has a maximum emission wavelength of 400 nm to 490 nm, more preferably a maximum emission wavelength of 420 nm to 485 nm, and particularly preferably a maximum emission wavelength of 440 nm to 480 nm. These maximum emission wavelengths are preferably the maximum emission wavelengths derived from the light emission of the light emitting material contained in the first organic layer, because the external quantum efficiency of the light emitting device of this embodiment is more excellent. It is more preferable that the maximum emission wavelength derived from the light emission of the metal complex or the maximum emission wavelength derived from the light emission of the metal complex represented by the formula (1 ′), of the metal complex represented by the formula (1 ′) More preferably, the maximum emission wavelength is derived from light emission.

  From the viewpoint of adjusting the emission color of the light emitting device of this embodiment (particularly adjusting the emission color to white), the emission spectrum of the light emitting device of this embodiment preferably has a maximum emission wavelength of 495 nm or more and less than 750 nm. More preferably, the maximum emission wavelength is 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 the maximum emission wavelengths derived from the light emission of the light emitting material contained in the second organic layer, since the external quantum efficiency of the light emitting device of this embodiment is more excellent. More preferably, it is a maximum emission wavelength derived from light emission of the light emitting material contained in C, and is derived from light emission of the metal complex constituting unit contained in the polymer compound of the layer B or the metal complex represented by the formula (2). The maximum emission wavelength is more preferable, and the maximum emission wavelength derived from the light emission of the metal complex constituent unit contained in the polymer compound of the layer B is particularly preferable.

  From the viewpoint of adjusting the emission color of the light-emitting element of this embodiment (particularly adjusting the emission color to white), the emission spectrum of the light-emitting element of this embodiment has two or more maximum emission wavelengths at 495 nm or more and less than 750 nm. It is preferable to have. Of the two or more maximum emission wavelengths, the difference between at least two maximum emission wavelengths is preferably 10 to 200 nm, more preferably 20 to 150 nm, and still more preferably 40 to 120 nm. Of these two maximum emission wavelengths, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, so at least one is the maximum emission wavelength derived from the light emission of the light emitting material contained in the second organic layer. It is more preferable that it is the maximum emission wavelength derived from light emission of the light emitting material contained in the layer B or the layer C, and it is represented by the metal complex constituent unit contained in the polymer compound of the layer B or the formula (2) The maximum emission wavelength derived from the light emission of the metal complex is more preferable, and the maximum emission wavelength derived from the light emission of the metal complex constituent unit contained in the polymer compound of the layer B is particularly preferable.

  From the viewpoint of adjusting the emission color of the light-emitting element of this embodiment (particularly adjusting the emission color to white), the emission spectrum of the light-emitting element of this embodiment has two or more maximum emission wavelengths at 495 nm or more and less than 750 nm. It is preferable. Among the two or more maximum emission wavelengths, the combination of at least two maximum emission wavelengths has one maximum emission wavelength (hereinafter, also referred to as “maximum emission wavelength on the short wavelength side”) of 500 nm or more and less than 570 nm, In addition, it is preferable that the other maximum emission wavelength (hereinafter also referred to as “longest emission wavelength on the long wavelength side”) be 570 nm or more and 680 nm or less. The maximum emission wavelength on the short wavelength side is preferably from 505 nm to 550 nm. The maximum emission wavelength on the long wavelength side is preferably from 590 nm to 640 nm.

  The maximum emission wavelength on the short wavelength side is preferably the maximum emission wavelength derived from light emission of the light emitting material contained in the first organic layer, since the external quantum efficiency of the light emitting device of this embodiment is more excellent. When the maximum emission wavelength on the short wavelength side is the maximum emission wavelength derived from the light emission of the light emitting material contained in the first organic layer, the first organic layer has the metal complex represented by formula (1) or the formula ( It is preferable that the metal complex represented by 1 ') and the metal complex represented by Formula (2) are included, and the maximum emission wavelength on the short wavelength side is derived from the light emission of the metal complex represented by Formula (2). It is more preferable that the light emission wavelength be a maximum emission wavelength.

  The maximum emission wavelength on the long wavelength side is preferably the maximum emission wavelength derived from the light emission of the light emitting material contained in the second organic layer, because the external quantum efficiency of the light emitting device of this embodiment is more excellent. Or it is more preferable that it is the maximum light emission wavelength originating in light emission of the luminescent material contained in the layer C, and it is light emission of the metal complex structural unit contained in the polymer compound of the layer B, or the metal complex represented by Formula (2). It is more preferable that the emission wavelength is derived from the maximum emission wavelength, and it is particularly preferable that the emission wavelength be derived from the light emission of the metal complex constituent unit contained in the polymer compound of layer B.

  In the light emitting device of this embodiment, when the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of this embodiment is more excellent. Preferably, at least one of a hole injection layer and a hole transport layer is further provided between the anode and the second organic layer. Further, when the second organic layer is a second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, so that the cathode and the first organic layer It is preferable to further include at least one of an electron injection layer and an electron transport layer between the organic layer.

  In the light emitting device of this embodiment, when the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of this embodiment is more excellent. It is preferable to further include at least one of a hole injection layer and a hole transport layer between the anode and the first organic layer. In addition, when the second organic layer is a second light emitting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, so the cathode and the second organic layer It is preferable to further include at least one of an electron injection layer and an electron transport layer between the organic layer.

  In the light emitting device of the present embodiment, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, It is preferable to further have a hole injection layer between the anode and the second organic layer. In addition, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, so the cathode and the first organic layer It is preferable to further include at least one of an electron injection layer and an electron transport layer between the layers.

  In the light emitting device of the present embodiment, when the second organic layer is an electron transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present embodiment is more excellent. Preferably, at least one of a hole injection layer and a hole transport layer is further provided between the first organic layer and the first organic layer. In addition, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present embodiment is more excellent, so the cathode and the second organic layer It is preferable to further have an electron injection layer between them.

  As a specific layer structure of the light emitting device of the present embodiment, for example, layer structures represented by the following (D1) to (D15) can be given. The light emitting device of this embodiment usually has a substrate, but may be laminated from the anode on the substrate, or may be laminated from the cathode on the substrate.

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

  In the above (D1) to (D15), “/” means that the front and back layers are adjacently stacked. For example, “second light emitting layer (second organic layer) / first light emitting layer (first organic layer)” means a second light emitting layer (second organic layer) and a first light emitting layer. (First organic layer) means that they are laminated adjacent to each other.

  Since the external quantum efficiency of the light emitting device of this embodiment is more excellent, the layer configuration represented by (D3) to (D12) is preferable, the layer configuration represented by (D3) to (D10) is more preferable, and (D3 ) To (D6) are more preferable.

In the light emitting device of this embodiment, the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer, and the cathode are each provided in two or more layers as necessary. May be.
When there are a plurality of anodes, hole injection layers, hole transport layers, second light emitting layers, electron transport layers, electron injection layers, and cathodes, the materials constituting them may be the same or different.

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

  In the light emitting element of this embodiment, the order, the number, and the thickness of the layers to be stacked may be adjusted in consideration of the light emission efficiency and the element life of the light emitting element.

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

  When the light-emitting element of the present embodiment has the second light-emitting layer, and the later-described hole transport layer and the later-described electron transport layer are not the second organic layer, the second light-emitting layer is the second organic layer. A layer is preferred.

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

  When the light-emitting element of the present embodiment has a hole transport layer and the above-described second light-emitting layer and an electron transport layer described later are not the second organic layer, the hole transport layer is the second organic layer. It is preferable that

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

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

  The electron injection layer is a layer containing an electron injection material. As an electron injection material contained in an electron injection layer, the electron injection material which the above-mentioned 1st composition may contain is mentioned, for example. The electron injection material contained in the electron injection layer may be contained singly or in combination of two or more.

[Substrate / Electrode]
The substrate in the light-emitting element is preferably a substrate that does not change chemically when the electrodes and the organic layer are formed. The substrate may be a substrate made of a material such as glass, plastic, or silicon. When an opaque substrate is used, it is preferable that the electrode farthest from the substrate is 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.

  In the light emitting device of this embodiment, at least one of the anode and the cathode is usually transparent or translucent, but the anode is preferably transparent or translucent.

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

[Method for Manufacturing Light-Emitting Element]
In the light emitting device of this embodiment, as a method for forming the first organic layer, the second organic layer, and other layers, when using a low molecular compound, for example, from a vacuum deposition method from a powder, a solution or a molten state In the case of using a polymer compound, for example, a method of forming a film from a solution or a molten state is used.

  The first organic layer, the second organic layer, and other layers can be formed by a wet method such as a spin coating method or an ink jet printing method using the inks including the various inks and various materials described above. Note that the first organic layer and the second organic layer may be formed by a dry method such as a vacuum evaporation method.

  When the first organic layer is formed by a wet method, it is preferable to use the first ink.

  When the second organic layer is the layer B and the layer B is formed by a wet method, the ink of the layer B or the ink of the layer B ′ is preferably used, and the ink of the layer B ′ is more preferably used. . When the second organic layer is formed by a wet method using the ink of layer B ′, the layer contained in the second organic layer by heating or light irradiation (preferably heating) after the layer formation. The polymer compound B ′ can be crosslinked. When the polymer compound of the layer B ′ is in a crosslinked state (crosslinked product of the polymer compound of the layer B ′) and contained in the second organic layer, the second organic layer is substantially free from the solvent. It is insolubilized. Therefore, the second organic layer can be suitably used for stacking light emitting elements.

  When the second organic layer is the layer C and the layer C is formed by a wet method, it is preferable to use the ink of the layer C.

  When the second organic layer is the layer C ′ and the layer C ′ is formed by a wet method, it is preferable to use the ink of the layer C ′. In the case where the second organic layer is formed by a wet method using the ink of the layer C ′, after the layer is formed, by crosslinking or heating (preferably heating), the crosslinking contained in the second organic layer A compound having a group can be crosslinked. When the compound having a crosslinking group is contained in the second organic layer in a crosslinked state (crosslinked product of the compound having a crosslinking group), the second organic layer is substantially insolubilized in the solvent. . Therefore, the second organic layer can be suitably used for stacking light emitting elements.

The heating temperature for crosslinking is usually 25 ° C to 300 ° C, preferably 50 ° C to 260 ° C, more preferably 130 ° C to 230 ° C, and further preferably 180 ° C to 210 ° C. .
The heating time is usually 0.1 minutes to 1000 minutes, preferably 0.5 minutes to 500 minutes, more preferably 1 minute to 120 minutes, and further preferably 10 minutes to 60 minutes. .

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

  Examples of the analysis method of the components contained in the first organic layer or the second organic layer include chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Examples include instrumental analysis methods such as mass spectrometry (MS), and analysis methods combining chemical separation analysis methods and instrumental analysis methods.

  By subjecting the first organic layer or the second organic layer to solid-liquid extraction using an organic solvent such as toluene, xylene, chloroform, tetrahydrofuran, etc., components that are substantially insoluble in the organic solvent (insoluble Component) and a component that dissolves in an organic solvent (dissolved component). Insoluble components can be analyzed by infrared spectroscopy or nuclear magnetic resonance spectroscopy, and dissolved components can be analyzed by nuclear magnetic resonance spectroscopy or mass spectrometry.

[Uses of light-emitting elements]
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-M3> Synthesis of Compounds M1-M3 Compounds M1, M2, and M3 were synthesized according to the method described in International Publication No. 2013/146806.

<Synthesis Example R1, RM1> Synthesis of Metal Complex R1 and RM1 Metal Complex R1 was synthesized according to the method described in JP-A-2008-179617.
The metal complex RM1 was synthesized according to the method described in International Publication No. 2009/157424.

<Synthesis Example G1> Synthesis of Metal Complex G1 Metal complex G1 was synthesized according to the method described in International Publication No. 2009/131255.

<Synthesis Example HTL1> Synthesis of Polymer Compound HTL-1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound M1 (0.800 g), Compound M2 (0.149 g), Compound M3 (1. 66 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.4 mg) and toluene (45 mL) were added and heated to 100 ° C.
(Step 2) A 20% by mass aqueous tetraethylammonium hydroxide solution (16 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 7 hours.
(Step 3) After the reaction, 2-ethylphenylboronic acid (90 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.3 mg) were added thereto and refluxed for 17.5 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 1.64 g of the polymer compound HTL-1. Mn of the high molecular compound HTL-1 was 3.5 × 10 ⁴ , and Mw was 2.2 × 10 ⁵ .

  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 40:10:50.

<Synthesis Example EML1> Synthesis of Polymer Compound EML-1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound M1 (2.52 g), Compound M2 (0.470 g), Compound M3 (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 polymer compound EML-1 has theoretical values determined from the amounts of the raw materials charged, a structural unit derived from the compound M1, a structural unit derived from the compound M2, a structural unit derived from the compound M3, 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 reaction mixture L1-2 ′)
After making the inside of reaction container nitrogen atmosphere, compound L1-2 (50 g) and thionyl chloride (100 mL) were added and stirred under 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 L1-2 ′.

(Synthesis of Compound L1-3)
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 L1-2 ′ (total amount) obtained in (synthesis of reaction mixture L1-2 ′) 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 L1-3 (50 g). The HPLC area percentage value of Compound L1-3 was 95.2%. The required amount of compound L1-3 was obtained by repeating the above operation.

The analysis results of Compound L1-3 were 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 L1-5)
After making the inside of reaction container nitrogen atmosphere, compound L1-3 (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 L1-5 (6 g). . The HPLC area percentage value of Compound L1-5 was 99.1%.

The analysis results of Compound L1-5 were 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 B1)
After making the inside of the reaction vessel a nitrogen atmosphere, tris (acetylacetonato) iridium (III) (1.4 g), compound L1-5 (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. B1 (2.8 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) = 7.30 (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 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 results of Compound 5-3 were 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 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 B6)
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 B6. (0.65 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) = 7.77 (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 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).

<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 second organic 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 organic layer (second light emitting layer) was formed.

(Formation of first organic layer)
Compound HM-1 and metal complex B1 (compound HM-1 / metal complex B1 = 75% by mass / 25% by mass) were dissolved in toluene at a concentration of 2% by mass. Using the obtained toluene solution, a film having a thickness of 75 nm was formed on the second organic layer by spin coating, and the first organic layer was heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. (First light emitting layer) was formed. 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 is formed on the first organic layer by spin coating. Then, an electron transport layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen 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 595 nm was observed. Light emission at 470 nm and 495 nm was light emission derived from the metal complex B1, and light emission at 595 nm was light emission derived from the polymer compound EML-1. The external quantum efficiency at 100 cd / m ² was 18.6 [%], and the chromaticity coordinates (x, y) were (0.45, 0.38).

<Example D2> Production and Evaluation of Light-Emitting Element D2 In place of "polymer compound EML-1" in (formation of second organic layer) in example D1, "polymer compound HTL-1 and metal complex R1" A light emitting device D2 was produced in the same manner as in Example D1, except that (polymer compound HTL-1 / metal complex R1 = 65 mass% / 35 mass%) was used.

By applying a voltage to the light emitting element D2, EL light emission having a maximum light emission wavelength of an emission spectrum at 465 nm, 495 nm, and 595 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 595 nm was light emission derived from the metal complex R1. The external quantum efficiency at 100 cd / m ² was 11.8 [%], and the chromaticity coordinates (x, y) were (0.31, 0.34).

<Example D3> Production and Evaluation of Light-Emitting Element D3 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) In the same manner as in Example D1, except that “compound HM-1 and metal complex B3 (compound HM-1 / metal complex B3 = 75 mass% / 25 mass%)” was used instead of “25 mass%)”. A light-emitting element D3 was manufactured.

By applying a voltage to the light emitting element D3, EL light emission having a maximum emission wavelength of an emission spectrum at 470 nm, 495 nm, and 595 nm was observed. Light emission at 470 nm and 495 nm was light emission derived from the metal complex B3, and light emission at 595 nm was light emission derived from the polymer compound EML-1. The external quantum efficiency at 100 cd / m ² was 10.4 [%], and the chromaticity coordinates (x, y) were (0.57, 0.39).

<Example D4> Production and Evaluation of Light-Emitting Element D4 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) In the same manner as in Example D1, except that “compound HM-1 and metal complex B5 (compound HM-1 / metal complex B5 = 75 mass% / 25 mass%)” was used instead of “25 mass%)”. A light-emitting element D4 was manufactured.

By applying a voltage to the light-emitting element D4, EL light emission having a maximum emission wavelength of the emission spectrum at 465 nm, 495 nm, and 595 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 595 nm was light emission derived from the polymer compound EML-1. The external quantum efficiency at 100 cd / m ² was 18.1 [%], and the chromaticity coordinates (x, y) were (0.42, 0.36).

<Example D5> Production and Evaluation of Light-Emitting Element D5 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) In the same manner as in Example D1, except that “compound HM-1 and metal complex B6 (compound HM-1 / metal complex B6 = 75 mass% / 25 mass%)” was used instead of “25 mass%)”. A light-emitting element D5 was manufactured.

By applying a voltage to the light emitting element D5, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 595 nm was observed. The light emission at 480 nm and 510 nm was light emission derived from the metal complex B6, and the light emission at 595 nm was light emission derived from the polymer compound EML-1. The external quantum efficiency at 100 cd / m ² was 20.7 [%], and the chromaticity coordinates (x, y) were (0.41, 0.40).

<Example D6> Production and Evaluation of Light-Emitting Element D6 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) In the same manner as in Example D1, except that “Compound HM-1 and Metal Complex B7 (Compound HM-1 / Metal Complex B7 = 75 mass% / 25 mass%)” was used instead of “25 mass%)”. A light-emitting element D6 was manufactured.

By applying a voltage to the light emitting element D6, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 595 nm was observed. The light emission at 480 nm and 510 nm was light emission derived from the metal complex B7, and the light emission at 595 nm was light emission derived from the polymer compound EML-1. The external quantum efficiency at 100 cd / m ² was 20.1 [%], and the chromaticity coordinates (x, y) were (0.43, 0.40).

<Example D7> Production and Evaluation of Light-Emitting Element D7 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) In the same manner as in Example D1, except that “compound HM-1 and metal complex B8 (compound HM-1 / metal complex B8 = 75 mass% / 25 mass%)” was used instead of “25 mass%)”. A light emitting device D7 was manufactured.

By applying a voltage to the light emitting element D7, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 510 nm, and 595 nm was observed. Light emission at 480 nm and 510 nm was light emission derived from the metal complex B8, and light emission at 595 nm was light emission derived from the polymer compound EML-1. The external quantum efficiency at 100 cd / m ² was 20.6 [%], and the chromaticity coordinates (x, y) were (0.42, 0.40).

<Comparative Example CD1> Production and Evaluation of Light-Emitting Element CD1 (Formation of second organic layer) in Example D1 was changed to the following (Formation of second organic layer-CD1), and further in Example D1 ( A light emitting device CD1 was produced in the same manner as in Example D1, except that (Formation of the first organic layer) was changed to the following (Formation of the first organic layer-CD1).

(Formation of second organic layer-CD1)
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 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 organic layer (hole transport layer) was formed.

(Formation of first organic layer-CD1)
Compound HM-1, metal complex B1 and metal complex R1 (compound HM-1 / metal complex B1 / metal complex R1 = 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 organic layer by spin coating, and the first organic layer was heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. (Light emitting layer) was formed.

(Evaluation of light emitting element)
By applying a voltage to the light emitting element CD1, EL light emission having a maximum light emission wavelength of an emission spectrum at 465 nm, 495 nm, and 590 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 590 nm was light emission derived from the metal complex R1. The external quantum efficiency at 100 cd / m ² was 2.6 [%], and the chromaticity coordinates (x, y) were (0.53, 0.40).

<Example D8> Production and Evaluation of Light-Emitting Element D8 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) "Compound HM-1, Metal Complex B5 and Metal Complex G1 (Compound HM-1, Metal Complex B5 / Metal Complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device D8 was produced in the same manner as in Example D1 except that it 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 595 nm was observed. These luminescences were luminescences derived from the metal complex B5, the metal complex G1, and the polymer compound EML-1. The external quantum efficiency at ²⁰ cd / m ² was 17.0 [%], and the chromaticity coordinates (x, y) were (0.43, 0.43).

<Example D9> Production and Evaluation of Light-Emitting Element D9 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) "Compound HM-1, Metal Complex B2 and Metal Complex G1 (Compound HM-1, Metal Complex B2 / Metal Complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device D9 was produced in the same manner as in Example D1 except that it was used.

By applying a voltage to the light emitting element D9, EL light emission having a maximum light emission wavelength of 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 G1, and the polymer compound EML-1. The external quantum efficiency at ²⁰ cd / m ² was 12.7 [%], and the chromaticity coordinates (x, y) were (0.45, 0.43).

<Example D10> Production and Evaluation of Light-Emitting Element D10 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) "Compound HM-1, Metal Complex B1 and Metal Complex G1 (Compound HM-1 / Metal Complex B1 / Metal Complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device D10 was produced in the same manner as in Example D1 except that it was used.

By applying a voltage to the light emitting element D10, EL light emission having a maximum 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 B1, the metal complex G1, and the polymer compound EML-1. The external quantum efficiency at ²⁰ cd / m ² was 15.7 [%], and the chromaticity coordinates (x, y) were (0.47, 0.44).

<Example D11> Production and Evaluation of Light-Emitting Element D11 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) "Compound HM-1, metal complex B6 and metal complex G1 (compound HM-1 / metal complex B6 / metal complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device D11 was produced in the same manner as in Example D1 except that it was used.

By applying a voltage to the light emitting element D11, EL light emission having a maximum light emission wavelength of an emission spectrum at 480 nm, 515 nm, and 600 nm was observed. These luminescences were luminescences derived from the metal complex B6, the metal complex G1, and the polymer compound EML-1.
The external quantum efficiency at ²⁰ cd / m ² was 17.6 [%], and the chromaticity coordinates (x, y) were (0.46, 0.46).

<Example D12> Production and Evaluation of Light-Emitting Element D12 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) "Compound HM-1, Metal Complex B7 and Metal Complex G1 (Compound HM-1 / Metal Complex B7 / Metal Complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device D12 was produced in the same manner as in Example D1 except that it 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 595 nm was observed. These luminescences were luminescence derived from the metal complex B7, the metal complex G1, and the polymer compound EML-1.
The external quantum efficiency at 20 cd / m ² was 20.8 [%], and the chromaticity coordinates (x, y) were (0.47, 0.44).

<Example D13> Production and Evaluation of Light-Emitting Element D13 "Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75 mass% /" in Example D1 (Formation of First Organic Layer)) "Compound HM-1, Metal Complex B8 and Metal Complex G1 (Compound HM-1 / Metal Complex B8 / Metal Complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device D13 was produced in the same manner as in Example D1 except that it 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 595 nm was observed. These luminescences were luminescences derived from the metal complex B8, the metal complex G1, and the polymer compound EML-1.
The external quantum efficiency at ²⁰ cd / m ² was 19.2 [%], and the chromaticity coordinates (x, y) were (0.45, 0.45).

<Comparative Example CD2> Production and Evaluation of Light-Emitting Element CD2 “Compound HM-1 and Metal Complex B1 (Compound HM-1 / Metal Complex B1 = 75% by mass / in Example 1) (Formation of First Organic Layer)” "Compound HM-1, metal complex B4 and metal complex G1 (compound HM-1 / metal complex B4 / metal complex G1 = 74 mass% / 25 mass% / 1 mass%)" instead of "25 mass%)" A light emitting device CD2 was produced in the same manner as in Example D1 except that it was used.

By applying a voltage to the light emitting element CD2, EL light emission having a maximum light 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 G1, and the polymer compound EML-1. The external quantum efficiency at ²⁰ cd / m ² was 10.6 [%], and the chromaticity coordinates (x, y) were (0.47, 0.44).

Claims (15)

An anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer A containing a metal complex represented by the formula (1),
The second organic layer is
Layer B containing at least one of a polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (2), and a crosslinked product of the polymer compound Or
The light emitting element which is layer C 'containing the crosslinked body of the compound which has a metal complex represented by Formula (2), and a crosslinking group.

[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 a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, or an alkyl group having 2 to 30 carbon atoms, This group 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.
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. ] The light emitting element of Claim 1 whose metal complex represented by said Formula (1) is a metal complex represented by 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. ] An anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer and the second organic layer are light emitting layers;
The light emitting element whose said 1st organic layer is layer A 'containing the metal complex represented by Formula (1').

[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 the group 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. ] The second organic layer is
Layer B containing at least one of a polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (2), and a crosslinked product of the polymer compound Or
The light emitting element of Claim 3 which is the layer C containing the metal complex represented by Formula (2).

[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.
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. ] An anode, a cathode, and a first organic layer and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer A ′ containing a metal complex represented by the formula (1 ′),
The second organic layer is
Layer B containing at least one of a polymer compound containing a structural unit having a group obtained by removing one or more hydrogen atoms from the metal complex represented by formula (2), and a crosslinked product of the polymer compound Or
Layer C containing a metal complex represented by the formula (2)
A light emitting element.

[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 the group 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.
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. ] The second organic layer is the layer B;
The light emitting device according to claim 1, wherein the polymer compound further includes a structural unit having a crosslinking group. The second organic layer is the layer B;
The structural unit is a structural unit represented by formula (2-1B), a structural unit represented by formula (2-2B), a structural unit represented by formula (2-3B), or formula (2-4B). The light emitting element as described in any one of Claims 1, 2, and 4-6 which is a structural unit represented by these.

[Where:
M ^1B represents a group obtained by removing one hydrogen atom from the metal complex represented by the formula (2).
L ^C represents an oxygen atom, a sulfur atom, —N (R ^A ) —, —C (R ^B ) ₂ —, —C (R ^B ) ═C (R ^B ) —, —C≡C—, an arylene group or It represents a divalent heterocyclic group, and these groups may have a substituent. R ^A 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. R ^B 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 ^RBs may be the same or different and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. When a plurality of ^LC are present, they may be the same or different.
n ^c1 represents an integer of 0 or more. ]

[Where:
M ^1B represents the same meaning as described above.
L ^d and ^{L e} each independently represent an oxygen atom, a sulfur _{^{atom, -N (R A) -,}} - C (R B) 2 -, - C (R B) = C (R B) -, - C Represents ≡C—, an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. R ^A and R ^B represent the same meaning as described above. When a plurality of L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent. ]

[Where:
L ^d and n ^d1 represent the same meaning as described above.
M ^2B represents a group obtained by removing two hydrogen atoms from the metal complex represented by the formula (2). ]

[Where:
L ^d and n ^d1 represent the same meaning as described above.
M ^3B represents a group obtained by removing three hydrogen atoms from the metal complex represented by the formula (2). ] The second organic layer is the layer B or the layer C ′;
The light-emitting element according to claim 1, wherein the cross-linking group is a cross-linking group selected from the cross-linking group A group.
(Crosslinking group A group)

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different. A plurality of n ^XL may be the same or different. * 1 represents a binding position. These crosslinking groups may have a substituent. ] The light emitting element according to any one of claims 1 to 8, 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 light emitting element as described in any one of Claims 1-9 whose metal complex represented by said Formula (2) is a metal complex represented by 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 are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent. 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. ] 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 light-emitting element according to claim 10, 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 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 ^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. ] The first organic layer further contains a compound represented by the formula (H-1) and / or a polymer compound containing a structural unit represented by the formula (Y). The light emitting element as described in any one.

[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. ]

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which an arylene group and a divalent heterocyclic group are directly bonded, and these groups have a substituent. It may be. ]   The first organic layer further contains at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, and an antioxidant. 13. The light emitting device according to any one of items 12.   The light emitting element according to claim 1, wherein the first organic layer and the second organic layer are adjacent to each other.   The light emitting element according to claim 1, wherein the second organic layer is a layer provided between the anode and the first organic layer.