JP6851189B2 - Light emitting element and metal complex - Google Patents

Description

The present invention relates to a light emitting element and a metal complex used for the light emitting element.

Organic electroluminescent devices (hereinafter, also referred to as "light emitting devices") can be suitably used for display and lighting applications, and research and development are being actively carried out.
This light emitting element has an organic layer such as a light emitting layer and a charge transport layer.

Patent Document 1 describes a light emitting device using a metal complex 1 represented by the following formula as a light emitting layer.

International Publication No. 2014/156922

However, the light emitting device described in Patent Document 1 above does not always have sufficient external quantum efficiency.

Therefore, an object of the present invention is to provide a light emitting device having excellent external quantum efficiency. Another object of the present invention is to provide a metal complex useful for producing a light emitting device having excellent external quantum efficiency.

The present invention provides the following [1] to [11].

［式中、
Ｍ^１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^１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^１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。
環Ｒ^１Ａは、窒素原子、Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ及び炭素原子で構成されるトリアゾール環又はジアゾール環を表す。
環Ｒ^２Ａは、２つの炭素原子、Ｅ^２１Ａ、Ｅ^２２Ａ、Ｅ^２３Ａ及びＥ^２４Ａで構成されるベンゼン環、ピリジン環又はピリミジン環を表す。
Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｅ^２１Ａ、Ｅ^２２Ａ、Ｅ^２３Ａ及びＥ^２４Ａは、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｅ^２１Ａ、Ｅ^２２Ａ、Ｅ^２３Ａ及びＥ^２４Ａが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。Ｅ^１１Ａが窒素原子の場合、Ｒ^１１Ａは存在しても存在しなくてもよい。Ｅ^１２Ａが窒素原子の場合、Ｒ^１２Ａは存在しても存在しなくてもよい。Ｅ^２１Ａが窒素原子の場合、Ｒ^２１Ａは存在しない。Ｅ^２２Ａが窒素原子の場合、Ｒ^２２Ａは存在しない。Ｅ^２３Ａが窒素原子の場合、Ｒ^２３Ａは存在しない。Ｅ^２４Ａが窒素原子の場合、Ｒ^２４Ａは存在しない。
Ｒ^１３Ａは、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）で表される基である。Ｒ^１３Ａが複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａは、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、ハロゲン原子、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）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。Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。但し、Ｒ^１１Ａ及びＲ^１２Ａのうち、少なくとも１つは式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）で表される基であり、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａのうち、少なくとも１つは式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）で表される基であり、且つ、Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａのうち、少なくとも１つは、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基又は式（Ｄ−Ｃ）で表される基である。
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、
ｍ^ＤＡ１、ｍ^ＤＡ２及びｍ^ＤＡ３は、それぞれ独立に、０以上の整数を表す。
Ｇ^ＤＡは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^ＤＡ１、Ａｒ^ＤＡ２及びＡｒ^ＤＡ３は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^ＤＡ１、Ａｒ^ＤＡ２及びＡｒ^ＤＡ３が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^ＤＡは、同一でも異なっていてもよい。］

［式中、
ｍ^ＤＡ１、ｍ^ＤＡ２、ｍ^ＤＡ３、ｍ^ＤＡ４、ｍ^ＤＡ５、ｍ^ＤＡ６及びｍ^ＤＡ７は、それぞれ独立に、０以上の整数を表す。
Ｇ^ＤＡは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。複数あるＧ^ＤＡは、同一でも異なっていてもよい。
Ａｒ^ＤＡ１、Ａｒ^ＤＡ２、Ａｒ^ＤＡ３、Ａｒ^ＤＡ４、Ａｒ^ＤＡ５、Ａｒ^ＤＡ６及びＡｒ^ＤＡ７は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^ＤＡ１、Ａｒ^ＤＡ２、Ａｒ^ＤＡ３、Ａｒ^ＤＡ４、Ａｒ^ＤＡ５、Ａｒ^ＤＡ６及びＡｒ^ＤＡ７が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^ＤＡは、同一でも異なっていてもよい。］

［式中、
ｍ^ＤＡ１’は、１以上の整数を表す。
Ａｒ^ＤＡ１は、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^ＤＡ１が複数ある場合、それらは同一でも異なっていてもよい。
Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

［式中、Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］ [1] A light emitting device having an anode, a cathode, and a light emitting layer provided between the anode and the cathode, and the light emitting layer contains a metal complex represented by the formula (1-A). ..

[During the ceremony,
M ¹ 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 ¹ is a rhodium atom or an iridium atom, n ¹ + n ² is 3, and when M ¹ is a palladium atom or a platinum atom, n ¹ + n ² is 2.
Ring R ^1A represents a triazole ring or a diazole ring composed of a nitrogen atom, E ¹ , E ^11A , E ^{12A and a carbon atom.}
Ring R ^2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21A , E ^22A , E ^23A and E ^24A.
E ¹ , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A each independently represent a nitrogen atom or a carbon atom. When a ^{plurality of E 1} , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A exist, they may be the same or different from each other. When E ^11A is a nitrogen atom, R ^11A may or may not be present. When E ^12A is a nitrogen atom, R ^12A may or may not be present. If E ^21A is a nitrogen atom, then R ^21A does not exist. If E ^22A is a nitrogen atom, then R ^22A does not exist. If E ^23A is a nitrogen atom, then R ^23A does not exist. If E ^24A is a nitrogen atom, then R ^24A does not exist.
R ^13A is represented by a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). It is the basis. When a ^{plurality of R 13A} exist, they may be the same or different.
R ^11A , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryloxy group, halogen atom and formula (D). It represents a group represented by −A), a group represented by the formula (DB), a group represented by the formula (DC) or a group represented by the formula (DD), and these groups. May have a substituent. When a ^{plurality of R 11A} , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A exist, they may be the same or different from each other. However, ^{at least one of R 11A} and R ^12A is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DC). A group represented by the formula (DD), ^{and at least one of R 21A} , R ^22A , R ^23A and R ^24A is a group represented by the formula (DA), the formula (DB). A group represented by, a group represented by the formula (DC) or a group represented by the formula (DD), and R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R. ^At least one of 23A and R ^24A is a group represented by the formula (DA), a group represented by the formula (DB), or a group represented by the formula (DC).
A ^1- G ^1- A ² represents an anionic bidentate ligand. A ¹ and A ² 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 ^{there are a plurality of A 1-} G ^1- A ² , they may be the same or different. ]

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

[During the ceremony,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6, and m ^DA7 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. The plurality of G ^DAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, even if these groups have a substituent. Good. When ^{there are a plurality of Ar DA1} , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6, and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. The plurality of ^TDAs may be the same or different. ]

[During the ceremony,
m DA1'represents an integer greater than or ^{equal to 1.}
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. If there are multiple Ar ^DA1 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[In the formula, T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[2] ^{The light emitting device according to [1], wherein the R 13A} is a group represented by the formula (DC) or a group represented by the formula (DD).

[3] At ^{least one of the R 11A} and the R ^12A is a group represented by the formula (DC) or a group represented by the formula (DD), [1] or [ 2] The light emitting element.

[4] The R ^22A is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or the above formula ( The light emitting device according to any one of [1] to [3], which is a group represented by DD).

［式中、
Ｒ^ｐ１、Ｒ^ｐ２、Ｒ^ｐ３及びＲ^ｐ４は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はフッ素原子を表す。Ｒ^ｐ１、Ｒ^ｐ２及びＲ^ｐ４が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
ｎｐ１は、０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０又は１を表し、ｎｐ４は０〜４の整数を表す。複数あるｎｐ１は、同一でも異なっていてもよい。］ [5] At least one of the R ^11A , the R ^12A , the R ^13A , the R ^21A , the R ^22A , the R ^23A and the R ^24A is a group represented by the formula (DA1). The group according to any one of [1] to [4], which is a group represented by (DA2), a group represented by the formula (DA3), or a group represented by the formula (DA4). Light emitting element.

[During the ceremony,
R ^p1 , R ^p2 , R ^p3 and R ^p4 independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom. When ^{there are a plurality of R p1} , R ^p2 and R ^p4 , they may be the same or different from each other.
np1 represents an integer from 0 to 5, np2 represents an integer from 0 to 3, np3 represents 0 or 1, and np4 represents an integer from 0 to 4. The plurality of np1s may be the same or different. ]

［式中、
Ｒ^ｐ１、Ｒ^ｐ２及びＲ^ｐ３は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はフッ素原子を表す。Ｒ^ｐ１及びＲ^ｐ２が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
ｎｐ１は０〜５の整数を表し、ｎｐ２は０〜３の整数を表し、ｎｐ３は０又は１を表す。ｎｐ１及びｎｐ２が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。］ [6] At least one of the R ^11A , the R ^12A , the R ^13A , the R ^21A , the R ^22A , the R ^23A and the R ^24A is a group represented by the formula (DB1). The light emitting device according to any one of [1] to [4], which is a group represented by (DB2) or a group represented by the formula (DB3).

[During the ceremony,
R ^p1 , R ^p2 and R ^p3 independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom. When ^{there are a plurality of R p1} and R ^p2 , they may be the same or different from each other.
np1 represents an integer from 0 to 5, np2 represents an integer from 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 from each other. ]

［式中、
Ｒ^ｐ４及びＲ^ｐ５は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はハロゲン原子を表す。Ｒ^ｐ４及びＲ^ｐ５が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
ｎｐ４は、０〜４の整数を表し、ｎｐ５は０〜５の整数を表す。］ [7] At least one of the R ^11A , the R ^12A , the R ^13A , the R ^21A , the R ^22A , the R ^23A and the R ^24A is a group represented by the formula (DC1). The light emitting device according to any one of [1] to [4], which is a group represented by (DC2) or a group represented by the formula (DC3).

[During the ceremony,
R ^p4 and R ^p5 independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom, respectively. When ^{there are a plurality of R p4} and R ^p5 , they may be the same or different from each other.
np4 represents an integer of 0 to 4, and np5 represents an integer of 0 to 5. ]

［式中、
Ｒ^ｐ６は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はハロゲン原子を表す。Ｒ^ｐ６が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
ｎｐ６は０〜５の整数を表す。］ [8] The light emitting device according to any one of [1] to [4], wherein the group represented by the formula (DD) is a group represented by the formula (DD1).

[During the ceremony,
R ^p6 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When ^{there are a plurality of R p6s} , they may be the same or different from each other.
np6 represents an integer from 0 to 5. ]

［式中、Ｍ^１、ｎ^１、ｎ^２、Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ、Ｒ^２４Ａ及びＡ^１−Ｇ^１−Ａ^２は、前記と同じ意味を表す。］ [9] The metal complex represented by the formula (1-A) is a metal complex represented by the formula (1-A1), a metal complex represented by the formula (1-A2), and a metal complex represented by the formula (1-A3). The light emitting element according to any one of [1] to [8], which is a metal complex represented by (1) or a metal complex represented by the formula (1-A4).

[In the formula, M ¹ , n ¹ , n ² , R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A , R ^24A and A ^1- G ^1- A ² have the same meanings as described above. .. ]

［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以上の整数を表す。
Ｌ^Ｈ１は、アリーレン基、２価の複素環基、又は、−［Ｃ（Ｒ^Ｈ１１）_２］ｎ^Ｈ１１−で表される基を表し、これらの基は置換基を有していてもよい。Ｌ^Ｈ１が複数存在する場合、それらは同一でも異なっていてもよい。ｎ^Ｈ１１は、１以上１０以下の整数を表す。
Ｒ^Ｈ１１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。
複数存在するＲ^Ｈ１１は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｌ^Ｈ２は、−Ｎ（−Ｌ^Ｈ２１−Ｒ^Ｈ２１）−で表される基を表す。Ｌ^Ｈ２が複数存在する場合、それらは同一でも異なっていてもよい。Ｌ^Ｈ２１は、単結合、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Ｈ２１は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］ [10] The light emitting device according to any one of [1] to [9], wherein the light emitting layer further contains a compound represented by the formula (H-1).

[During the ceremony,
Ar ^H1 and Ar ^H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
n ^H1 and n ^H2 independently represent 0 or 1, respectively. When a ^{plurality of n H1s} are present, they may be the same or different. A plurality of n ^H2s may be the same or different.
^{n H3} represents an integer greater than or equal to 0.
L ^H1 represents an arylene group, a divalent heterocyclic group, or ^{a group represented by − [C (RH11} ) ₂ ] n ^H11 −, and these groups may have a substituent. When a ^{plurality of L H1s} exist, they may be the same or different. n ^H11 represents an integer of 1 or more and 10 or less.
^RH11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
The plurality of ^RH11s present may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which each is bonded.
L ^H2 represents a group represented by −N (−L ^{H21 −RH21) −.} When ^{there are a plurality of L H2s} , 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. ^RH21 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. ]

［式中、
Ｍ^１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^１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^１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。
環Ｒ^１Ａは、窒素原子、Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ及び炭素原子で構成されるトリアゾール環又はジアゾール環を表す。
環Ｒ^２Ａは、２つの炭素原子、Ｅ^２１Ａ、Ｅ^２２Ａ、Ｅ^２３Ａ及びＥ^２４Ａで構成されるベンゼン環、ピリジン環又はピリミジン環を表す。
Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｅ^２１Ａ、Ｅ^２２Ａ、Ｅ^２３Ａ及びＥ^２４Ａは、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｅ^２１Ａ、Ｅ^２２Ａ、Ｅ^２３Ａ及びＥ^２４Ａが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。Ｅ^１１Ａが窒素原子の場合、Ｒ^１１Ａは存在しても存在しなくてもよい。Ｅ^１２Ａが窒素原子の場合、Ｒ^１２Ａは存在しても存在しなくてもよい。Ｅ^２１Ａが窒素原子の場合、Ｒ^２１Ａは存在しない。Ｅ^２２Ａが窒素原子の場合、Ｒ^２２Ａは存在しない。Ｅ^２３Ａが窒素原子の場合、Ｒ^２３Ａは存在しない。Ｅ^２４Ａが窒素原子の場合、Ｒ^２４Ａは存在しない。
Ｒ^１３Ａは、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）で表される基である。Ｒ^１３Ａが複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａは、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリールオキシ基、ハロゲン原子、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）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。Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。但し、Ｒ^１１Ａ及びＲ^１２Ａのうち、少なくとも１つは式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）で表される基であり、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａのうち、少なくとも１つは式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基、式（Ｄ−Ｃ）で表される基又は式（Ｄ−Ｄ）で表される基であり、且つ、Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ及びＲ^２４Ａのうち、少なくとも１つは、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基又は式（Ｄ−Ｃ）で表される基である。
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、
ｍ^ＤＡ１、ｍ^ＤＡ２及びｍ^ＤＡ３は、それぞれ独立に、０以上の整数を表す。
Ｇ^ＤＡは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^ＤＡ１、Ａｒ^ＤＡ２及びＡｒ^ＤＡ３は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^ＤＡ１、Ａｒ^ＤＡ２及びＡｒ^ＤＡ３が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^ＤＡは、同一でも異なっていてもよい。］

［式中、
ｍ^ＤＡ１、ｍ^ＤＡ２、ｍ^ＤＡ３、ｍ^ＤＡ４、ｍ^ＤＡ５、ｍ^ＤＡ６及びｍ^ＤＡ７は、それぞれ独立に、０以上の整数を表す。
Ｇ^ＤＡは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。複数あるＧ^ＤＡは、同一でも異なっていてもよい。
Ａｒ^ＤＡ１、Ａｒ^ＤＡ２、Ａｒ^ＤＡ３、Ａｒ^ＤＡ４、Ａｒ^ＤＡ５、Ａｒ^ＤＡ６及びＡｒ^ＤＡ７は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^ＤＡ１、Ａｒ^ＤＡ２、Ａｒ^ＤＡ３、Ａｒ^ＤＡ４、Ａｒ^ＤＡ５、Ａｒ^ＤＡ６及びＡｒ^ＤＡ７が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^ＤＡは、同一でも異なっていてもよい。］

［式中、
ｍ^ＤＡ１’は、１以上の整数を表す。
Ａｒ^ＤＡ１は、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^ＤＡ１が複数ある場合、それらは同一でも異なっていてもよい。
Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

［式中、Ｔ^ＤＡは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］ [11] A metal complex represented by the formula (1-A).

[During the ceremony,
M ¹ 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 ¹ is a rhodium atom or an iridium atom, n ¹ + n ² is 3, and when M ¹ is a palladium atom or a platinum atom, n ¹ + n ² is 2.
Ring R ^1A represents a triazole ring or a diazole ring composed of a nitrogen atom, E ¹ , E ^11A , E ^{12A and a carbon atom.}
Ring R ^2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21A , E ^22A , E ^23A and E ^24A.
E ¹ , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A each independently represent a nitrogen atom or a carbon atom. When a ^{plurality of E 1} , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A exist, they may be the same or different from each other. When E ^11A is a nitrogen atom, R ^11A may or may not be present. When E ^12A is a nitrogen atom, R ^12A may or may not be present. If E ^21A is a nitrogen atom, then R ^21A does not exist. If E ^22A is a nitrogen atom, then R ^22A does not exist. If E ^23A is a nitrogen atom, then R ^23A does not exist. If E ^24A is a nitrogen atom, then R ^24A does not exist.
R ^13A is represented by a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). It is the basis. When a ^{plurality of R 13A} exist, they may be the same or different.
R ^11A , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryloxy group, halogen atom and formula (D). It represents a group represented by −A), a group represented by the formula (DB), a group represented by the formula (DC) or a group represented by the formula (DD), and these groups. May have a substituent. When a ^{plurality of R 11A} , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A exist, they may be the same or different from each other. However, ^{at least one of R 11A} and R ^12A is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DC). A group represented by the formula (DD), ^{and at least one of R 21A} , R ^22A , R ^23A and R ^24A is a group represented by the formula (DA), the formula (DB). A group represented by, a group represented by the formula (DC) or a group represented by the formula (DD), and R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R. ^At least one of 23A and R ^24A is a group represented by the formula (DA), a group represented by the formula (DB), or a group represented by the formula (DC).
A ^1- G ^1- A ² represents an anionic bidentate ligand. A ¹ and A ² 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 ^{there are a plurality of A 1-} G ^1- A ² , they may be the same or different. ]

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

[During the ceremony,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6, and m ^DA7 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. The plurality of G ^DAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, even if these groups have a substituent. Good. When ^{there are a plurality of Ar DA1} , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6, and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. The plurality of ^TDAs may be the same or different. ]

[During the ceremony,
m DA1'represents an integer greater than or ^{equal to 1.}
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. If there are multiple Ar ^DA1 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[In the formula, T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

According to the present invention, it is possible to provide a light emitting device having excellent external quantum efficiency. Further, according to the present invention, it is possible to provide a metal complex useful for producing a light emitting device having excellent external quantum efficiency.

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

<Explanation of common terms>
Unless otherwise specified, the terms commonly used in the present specification have the following meanings.

Me 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 coordination bond.

The "polymer compound" has a molecular weight distribution, the number average molecular weight in terms of polystyrene means a polymer which is ^{1 × 10 3 ~1 × 10 8} .

The polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or any other embodiment.

The terminal group of the polymer compound is preferably a stable group because if the polymerization active group remains as it is, the light emitting characteristics may deteriorate when the polymer compound is used for producing a light emitting element. The terminal group is preferably a group conjugated to the main chain, and examples thereof include a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.

By "low molecular compound" does not have a molecular weight distribution, molecular weight means a 1 × 10 ⁴ or less of the compound.

The “constituent unit” means a unit existing in one or more in a polymer compound.

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

"Aryl group" means the remaining atomic group excluding one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the aryl group is usually 6 to 60, preferably 6 to 20, and more preferably 6 to 10 without including the number of carbon atoms of the substituent.
The aryl group may have a substituent, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthrasenyl group, a 2-anthrasenyl group, a 9-anthrasenyl group, a 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, and the hydrogen atom in these groups is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom. Examples thereof include groups substituted with such as.

The "alkoxy group" may be either linear or branched. The number of carbon atoms of the linear alkoxy group is usually 1 to 40, preferably 4 to 10 without including the number of carbon atoms of the substituent. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10 without including the number of carbon atoms of the substituent.
The alkoxy group may have a substituent, for example, a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a tert-butyloxy group, a pentyloxy group, a hexyloxy group, and the like. Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, Examples thereof include a cycloalkoxy group, an aryl group, a group substituted with a fluorine atom and the like.
The number of carbon atoms of the "cycloalkoxy group" is usually 3 to 40, preferably 4 to 10 without including the number of carbon atoms of the substituent.
The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

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

A "p-valent heterocyclic group" (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. It means the remaining atomic group excluding the hydrogen atom of. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A "p-valent aromatic heterocyclic group" is preferred.
The "aromatic heterocyclic compound" is a heterocyclic compound such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphor, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, and dibenzophosphol. Even if the compound whose ring itself exhibits aromaticity and the heterocycle itself such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran do not exhibit aromaticity, the aromatic ring is fused to the heterocycle. Means a compound.

The number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, excluding the number of carbon atoms of the substituent.
The monovalent heterocyclic group may have a substituent, for example, a thienyl group, a pyrrolyl group, a furyl group, a pyridinyl group, a piperidinyl group, a quinolinyl group, an isoquinolinyl group, a pyrimidinyl group, a triazinyl group, and these. Examples thereof include a group in which the hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or the like.

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

The "amino group" may have a substituent, and a substituted amino group is preferable. As the substituent contained in the amino group, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group is preferable.
Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group and a diarylamino group.
Examples of the amino group include a dimethylamino group, a diethylamino group, a diphenylamino group, a bis (4-methylphenyl) amino group, a bis (4-tert-butylphenyl) amino group, and a bis (3,5-di-tert-). Butylphenyl) amino groups can be mentioned.

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

The "alkynyl group" may be either linear or branched. The number of carbon atoms of the alkynyl group is usually 2 to 20, preferably 3 to 20, not including the carbon atom of the substituent. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, 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, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, a 4- Examples thereof include a pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and a group in which these groups have a substituent.

The "arylene group" means the remaining atomic group excluding the two hydrogen atoms directly bonded to the carbon atoms constituting the ring from the aromatic hydrocarbon. The number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18, not including the number of carbon atoms of the substituent.
The arylene group may have a substituent, for example, a phenylene group, a naphthalenediyl group, an anthracendiyl group, a phenanthrenidyl group, a dihydrophenantrenidyl group, a naphthacendyl group, a full orangeyl group, a pyrenyl group, a perylenediyl group, Examples thereof include a chrysendiyl group and a group in which these groups have a substituent, and preferred groups are represented by the formulas (A-1) to (A-9) and (A-11) to (A-20). Is. The arylene group includes a group in which a plurality of these groups are bonded.

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

[Wherein, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. R and R ^a there are a plurality, each may be the same or different, bonded R ^a each other to each other, they may form a ring together with the atoms bonded thereto. ]

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

［式中、Ｒ及びＲ^ａは、前記と同じ意味を表す。］

[In the formula, R and ^Ra have the same meanings as described above. ]

The "crosslinked group" is a group capable of forming a new bond by subjecting it to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. It is a radical represented by any of B-1) to (B-17). These groups may have substituents.

The "substituent" is a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, a substituted amino group and an alkenyl group. , Cycloalkenyl group, alkynyl group or cycloalkynyl group. The substituent may be a cross-linking group.

<Light emitting element>
Next, the light emitting element according to this embodiment will be described.

The light emitting element according to the present embodiment has an anode, a cathode, and a light emitting layer provided between the anode and the cathode. The light emitting layer is a layer containing a metal complex represented by the formula (1-A).

<Light emitting layer>
The light emitting layer is a layer containing a metal complex represented by the formula (1-A). The light emitting layer may contain one kind of metal complex represented by the formula (1-A) alone or two or more kinds.

The content of the metal complex represented by the formula (1-A) in the light emitting layer may be within a range that functions as a light emitting layer. For example, the content of the metal complex represented by the formula (1-A) may be 0.1 to 50% by mass, preferably 1 to 40% by mass, based on the total amount of the light emitting layer, and is preferably 10 to 40% by mass. More preferably, it is 30% by mass.

Examples of the method for forming the light emitting layer include a vacuum vapor deposition method and a coating method typified by a spin coating method and an inkjet printing method, and the coating method is preferable. When the light emitting layer is formed by the coating method, it is preferable to use the ink of the light emitting layer described later.

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

The metal complex represented by the formula (1-A) is defined by the central metal M ¹ , the ligand whose number is defined by the subscript n ¹ , and the number of which is defined by the subscript n ^2. It is a metal complex composed of a ligand.

Since the external quantum efficiency of the light emitting element according to the present embodiment is more excellent, ^{M 1 is preferably an iridium atom or a platinum atom, and more preferably an iridium atom.}

When M ¹ is a rhodium atom or an iridium atom, n ¹ is preferably 2 or 3, and more preferably 3.

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

E ¹ is preferably a carbon atom.

When the ring R ^1A is a diazole ring, an ^{imidazole ring in which E 11A} is a nitrogen atom or an imidazole ring in which E ^12A is a nitrogen atom is preferable, and an imidazole ring in which E ^11A is a nitrogen atom is more preferable.

When ring R ^1A is a triazole ring, a triazole ring in which E ^11A and E ^12A are nitrogen atoms is preferable.

When the ring R ^2A is a pyridine ring, the pyridine ring in which E ^21A is a nitrogen atom, the pyridine ring in which E ^22A is a nitrogen atom, or the pyridine ring in which E ^23A is a nitrogen atom is preferable, and E ^22A is a nitrogen atom. Certain pyridine rings are more preferred.

When ring R ^2A is a pyrimidine ring, a pyrimidine ring in which E ^21A and E ^23A are nitrogen atoms, or a pyrimidine ring in which E ^22A and E ^24A are nitrogen atoms is preferable, and E ^22A and E ^24A are nitrogen atoms. A pyrimidine ring is more preferred.

Ring R ^2A is preferably a benzene ring.

Since ^{the external quantum efficiency of the light emitting device according to the present embodiment is more excellent in R 13A} , the group represented by the formula (DA), the group represented by the formula (DC) or the formula (DD). It is preferably a group represented by the formula (DC), more preferably a group represented by the formula (DC) or a group represented by the formula (DD), and is represented by the formula (DD). It is more preferable that it is a group.

When E ^11A is a nitrogen atom and R ^11A is present, R ^11A is an alkyl group, a cycloalkyl group, a group represented by the formula (DA), or a group represented by the formula (DB). , The group represented by the formula (DC) or the group represented by the formula (DD) is preferable, and the group represented by the formula (DA) is represented by the formula (DB). The group to be represented, the group represented by the formula (DC) or the group represented by the formula (DD) is more preferable, and the group represented by the formula (DA), the group represented by the formula (D-D). It is more preferably a group represented by C) or a group represented by the formula (DD), and a group represented by the formula (DC) or a group represented by the formula (DD). These groups may have substituents.

When E ^11A is a carbon atom, R ^11A is a hydrogen atom, an alkyl group, a cycloalkyl group, a group represented by the formula (DA), a group represented by the formula (DB), and a formula (D-). It is preferably a group represented by C) or a group represented by the formula (DD), a hydrogen atom, an alkyl group, a cycloalkyl group, a group represented by the formula (DC) or a group represented by the formula (D). It is more preferably a group represented by −D), further preferably a hydrogen atom, an alkyl group or a cycloalkyl group, particularly preferably a hydrogen atom, and these groups have a substituent. You may.

When E ^12A is a nitrogen atom and R ^12A is present, R ^12A is an alkyl group, a cycloalkyl group, a group represented by the formula (DA), or a group represented by the formula (DB). , The group represented by the formula (DC) or the group represented by the formula (DD) is preferable, and the group represented by the formula (DA) is represented by the formula (DB). The group to be represented, the group represented by the formula (DC) or the group represented by the formula (DD) is more preferable, and the group represented by the formula (DA), the group represented by the formula (D-D). It is more preferably a group represented by C) or a group represented by the formula (DD), and a group represented by the formula (DC) or a group represented by the formula (DD). These groups may have substituents.

When E ^12A is a carbon atom, R ^12A is a hydrogen atom, an alkyl group, a cycloalkyl group, a group represented by the formula (DA), a group represented by the formula (DB), and a formula (D-). It is preferably a group represented by C) or a group represented by the formula (DD), a hydrogen atom, an alkyl group, a cycloalkyl group, a group represented by the formula (DC) or a group represented by the formula (D). It is more preferably a group represented by −D), further preferably a hydrogen atom, an alkyl group or a cycloalkyl group, particularly preferably a hydrogen atom, and these groups have a substituent. You may.

^{When a plurality of R 11A} and R ^12A are present in the metal complex represented by the formula (1-A) (that is, when n ¹ is 2 or 3), at least among the ^{plurality of R 11A} and R ^12A. One is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). However, all of the plurality of R ^11A and / or all of the plurality of R ^12A are represented by the formula (DA), the group represented by the formula (DB), and the like. It is preferably a group represented by the formula (DC) or a group represented by the formula (DD).

Of R ^11A and R ^12A , at least one is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC) or a formula ( Although it is a group represented by DD), since the external quantum efficiency of the light emitting device according to the present embodiment is more excellent, R ^11A is a group represented by the formula (DA), the formula (DB). It is preferable that the group is represented by, the group represented by the formula (DC), or the group represented by the formula (DD).

Of R ^11A and R ^12A , at least one is preferably a group represented by the formula (DC) or a group represented by the formula (DD), and R ^11A is the group represented by the formula (DC). It is more preferable that it is a group represented by or a group represented by the formula (DD).

In the metal complex represented by the formula (1-A), ^{when a plurality of R 21A} , R ^22A , R ^23A and R ^24A are present (that is, when n ¹ is 2 or 3), a plurality of R ^21A are present. Of R ^22A , R ^23A and R ^24A , at least one is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DC). It may be a group represented by the formula (DD), but ^{all of the plurality of R 21A} , all of the plurality of R ^22A , all of the plurality of R ^23A , and / or a plurality of R ^24A. Are all represented by a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). It is preferably a group.

R ^21A , R ^22A , R ^23A and R ^24A are a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, a group represented by the formula (DA), and a group represented by the formula (DA), the formula (DB). ), The group represented by the formula (DC) or the group represented by the formula (DD) is preferable, and a hydrogen atom, an alkyl group, a cycloalkyl group and a formula (D-) are preferable. More preferably, it is a group represented by A), a group represented by the formula (DB), a group represented by the formula (DC) or a group represented by the formula (DD). Hydrogen atom, group represented by formula (DA), group represented by formula (DB), group represented by formula (DC) or group represented by formula (DD) It is more preferable that the group is a hydrogen atom, a group represented by the formula (DA), a group represented by the formula (DC) or a group represented by the formula (DD). Preferably, it is a hydrogen atom, a group represented by the formula (DA) or a group represented by the formula (DD), and these groups may have a substituent.

At ^{least one of R 21A} , R ^22A , R ^23A and R ^24A is represented by a group represented by the formula (DA), a group represented by the formula (DB), and a group represented by the formula (DC). However, since the external quantum efficiency of the light emitting device according to the present embodiment is more excellent, at least one of ^{R 22A} and R ^{23A is of the formula (D-D).} It is preferably a group represented by A), a group represented by the formula (DB), a group represented by the formula (DC) or a group represented by the formula (DD), and R ^22A is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). It is more preferable that R ^22A is a group represented by the formula (DA) or a group represented by the formula (DD).

In the metal complex represented by the formula (1-A), when a plurality of R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A are present (that is, n ¹ is 2 or 3). Case), a group ^{in which at least one of a plurality of R 11A} , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A is represented by the formula (DA), the formula (DB). It may be a group represented by or a group represented by the formula (DC), but ^{all of a plurality of R 11A} existing, all of a plurality of existing R ^12A , all of a plurality of existing R ^21A , and a plurality of existing R 21A exist. All of R ^22A , all of the plurality of R ^23A , and / or all of the plurality of R ^24A are represented by the formula (DA), the group represented by the formula (DB), or the group represented by the formula (DB). It is preferably a group represented by the formula (DC).

[Groups represented by formulas (DA), (DB), (DC) or (DD)]
Next, the groups represented by the formulas (DA), (DB), (DC) or (DD) will be described.

m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually integers of 10 or less, preferably 5 or less, more preferably 2 or less, and further. It is preferably 0 or 1. It is preferable that m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are the same integer, and m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are It is more preferable that they are the same integer.

m ^DA1'is usually an integer of 1 or more and 10 or less, preferably an integer of 1 or more and 5 or less, more preferably 1 or 2, and even more preferably 1.

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

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

[During the ceremony,
* 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).
** represents a combination with Ar ^{DA2 in} the formula ( ^{DA), Ar DA2 in} the formula ( ^DB ), Ar DA4 in the formula ( ^{DB), or Ar DA6 in the formula (DB).} ..
*** is a combination with Ar ^{DA3 in} the formula ( ^{DA), Ar DA3 in} the formula ( ^DB ), Ar DA5 in the formula ( ^{DB), or Ar DA7 in the formula (DB).} Represent.
^RDA 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. If there are multiple R ^DAs , they may be the same or different. ]

The 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. You may.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably a phenylene group, a fluorinatedyl group or a carbazolediyl group, and more preferably formulas (A-1) to ( It is a group represented by A-3), (A-8), (A-9), (AA-10), (AA-11), (AA-33) or (AA-34), and is more preferable. Is a group represented by the formulas (ArDA-1) to (ArDA-5), particularly preferably a group represented by the formulas (ArDA-1) to (ArDA-3), and particularly preferably a group represented by the formula (ArDA-3). It is a group represented by -1)

［式中、
Ｒ^ＤＡは前記と同じ意味を表す。
Ｒ^ＤＢは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^ＤＢが複数ある場合、それらは同一でも異なっていてもよい。］

[During the ceremony,
R ^DA has the same meaning as described above.
^RDB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When ^{there are a plurality of R DBs} , they may be the same or different. ]

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

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

［式中、Ｒ^ＤＡ及びＲ^ＤＢは、前記と同じ意味を表す。］

[In the formula, R ^DA and R ^DB have the same meanings as described above. ]

The group represented by the formula (DA) is preferably a group represented by the formulas (DA1) to (DA4), and more preferably the group represented by the formula (DA1) or (DA4). It is a group represented by, and more preferably a group represented by the formula (DA1).

The group represented by the formula (DB) is preferably a group represented by the formulas (DB1) to (DB3), and more preferably a group represented by the formula (DB1). is there.

The groups represented by the formula (DC) are preferably the groups represented by the formulas (DC1) to (DC3), and more preferably the groups represented by the formulas (DC1) to (DC2). It is a group represented by, and more preferably a group represented by the formula (DC1).

The group represented by the formula (DD) is preferably the group represented by the formula (DD1).

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, more preferably 1 or 2, and even more preferably 2. np5 is preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. np6 is preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and even more preferably 2 or 3.

R ^p1 , R ^p2 , R ^p3 , R ^p4 , R ^p5 and R ^p6 are preferably alkyl or cycloalkyl groups, more preferably methyl groups, ethyl groups, isopropyl groups, tert-butyl groups, hexyl groups, 2-Ethylhexyl group, cyclohexyl group, methoxy group, 2-ethylhexyloxy group, tert-octyl group or cyclohexyloxy group, more preferably methyl group, ethyl group, isopropyl group, tert-butyl group, hexyl group, 2 -Ethylhexyl group or tert-octyl group.

Examples of the group represented by the formula (DA) include groups represented by the formulas (DA-1) to (DA-12).

［式中、Ｒ^Ｄは、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、ヘキシル基、２−エチルヘキシル基、ｔｅｒｔ−オクチル基、シクロヘキシル基、メトキシ基、２−エチルヘキシルオキシ基又はシクロへキシルオキシ基を表す。Ｒ^Ｄが複数存在する場合、それらは同一でも異なっていてもよい。］

[In the formula, ^RD is 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 a group. If R ^D is plurally present, they may be the same or different. ]

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

［式中、Ｒ^Ｄは前記と同じ意味を表す。］

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

Examples of the group represented by the formula (DC) include groups represented by the formulas (DC-9) to (DC-17).

［式中、Ｒ^Ｄは前記と同じ意味を表す。］

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

Examples of the group represented by the formula (DD) include the groups represented by the formulas (DD-1) to (DD-8).

［式中、Ｒ^Ｄは前記と同じ意味を表す。］

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

The ^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.

[Anionic bidentate ligand]
Examples of the anionic bidentate ligand represented by A ^1- G ^1- A ^{2 include the ligand represented by the following.}

［式中、＊は、Ｍ^１と結合する部位を示す。］

[In the formula, * indicates a site that binds to ^{M 1.} ]

The ^{anionic bidentate ligand represented by A 1-} G ^1- A ² may be a ligand represented by the following. 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.}

［式中、
＊は、Ｍ^１と結合する部位を表す。
Ｒ^Ｌ１は、水素原子、アルキル基、シクロアルキル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。複数存在するＲ^Ｌ１は、同一でも異なっていてもよい。
Ｒ^Ｌ２は、アルキル基、シクロアルキル基、アリール基、１価の複素環基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。］

[During the ceremony,
* Represents a site that binds to ^{M 1.
RL1} represents a hydrogen atom, an alkyl group, a cycloalkyl group or a halogen atom, and these groups may have a substituent. A plurality of ^RL1s may be the same or different.
^RL2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. ]

^RL1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or a fluorine atom, more preferably a hydrogen atom or an alkyl group, and these groups may have a substituent.

^RL2 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 further preferably an aryl group. The group of may have a substituent.

Since the metal complex represented by the formula (1-A) is more excellent in the external quantum efficiency of the light emitting element according to the present embodiment, the metal complex represented by the formula (1-A1) is represented by the formula (1-A2). The metal complex represented by the formula (1-A3) or the metal complex represented by the formula (1-A4) is preferable, and the metal complex represented by the formula (1-A1) or the metal complex represented by the formula (1-A1) or It is more preferably a metal complex represented by the formula (1-A3), and further preferably a metal complex represented by the formula (1-A1).

Examples of the metal complex represented by the formula (1-A) include a metal complex represented by the following formula. In the formula, ^{E A} represents a group represented by the group or -N represented by -CH = =.

<Method for producing a metal complex represented by the formula (1-A)>
The metal complex represented by the formula (1-A) was obtained in, for example, a step of reacting a compound serving as a ligand with a metal compound (hereinafter, also referred to as “step 1”) and a step 1. It can be produced by a method including a step of carrying out a functional group conversion reaction of a ligand of a metal complex (hereinafter, also referred to as “step 2”).

First, step 1 will be described.

In step 1, for example, step A in which the compound represented by the formula (M-1) is reacted with the metal compound or its hydrate, and the compound obtained in step A (hereinafter, “metal complex intermediate”). (1 ') "and also referred to.) and includes a step B, the reaction of a precursor of the ligand represented by the compound or ^a 1 ^-G 1 -A ² formula (M-1) A metal complex (1 ″) is produced by the method.

［式中、Ｍ^１、ｎ^１、ｎ^２、環Ｒ^１Ａ、Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ及びＡ^１−Ｇ^１−Ａ^２は、前記と同じ意味を表す。環Ｒ^２はベンゼン環、ピリジン環又はピリミジン環を表し、これらの環は、Ｒ^２１Ａ、Ｒ^２２Ａ、Ｒ^２３Ａ又はＲ^２４Ａを有していてもよい。］

[In the formula, M ¹ , n ¹ , n ² , ring R ^1A , E ¹ , E ^11A , E ^12A , R ^11A , R ^12A , R ^13A and A ^1- G ^1- A ² have the same meaning as described above. Represent. Ring R ² represents a benzene ring, a pyridine ring or a pyrimidine ring, which rings may have R ^21A , R ^22A , R ^23A or R ^24A . ]

In step A, examples of the metal compound include iridium compounds such as iridium chloride, tris (acetylacetonato) iridium (III), chloro (cyclooctadiene) iridium (I) dimer, and iridium (III) acetate; Examples thereof include platinum compounds such as potassium; palladium compounds such as palladium chloride and palladium acetate; and rhodium compounds such as rhodium chloride. Examples of the hydrate of the metal compound include iridium chloride / trihydrate and rhodium chloride / trihydrate.

Examples of the metal complex intermediate (1') include a metal complex represented by the formula (M-2).

［式中、Ｍ^１、ｎ^１、ｎ^２、環Ｒ^１Ａ、環Ｒ^２、Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｒ^１１Ａ、Ｒ^１２Ａ及びＲ^１３Ａは、前記と同じ意味を表す。
ｎ^１’は、１又は２を表す。Ｍ^１がロジウム原子又はイリジウム原子の場合、ｎ^１’は２であり、Ｍ^１がパラジウム原子又は白金原子の場合、ｎ^１’は１である。］

[In the formula, M ¹ , n ¹ , n ² , ring R ^1A , ring R ² , E ¹ , E ^11A , E ^12A , R ^11A , R ^12A and R ^13A have the same meanings as described above.
n ^1'represents 1 or 2. If M ¹ is rhodium atom or an iridium atom, n 1 ^'is 2, when M ¹ is a palladium atom or a platinum atom, n ^1' is 1. ]

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

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 based on 1 mol of the metal complex intermediate (1'). Usually, it is 1 to 100 mol.

In step B, the reaction is preferably carried out in the presence of a silver compound such as silver trifluoromethanesulfonate. When a silver compound is used, the amount is usually 2 to 20 mol per 1 mol of the metal complex intermediate (1').

Next, step 2 will be described.

In step 2, examples of the functional group conversion reaction include known coupling reactions using transition metal catalysts such as Suzuki reaction, Buchwald reaction, Stille reaction, Negishi reaction and Kumada reaction.

In step 2, for example, step C in which the metal complex represented by the formula (1 ″) is reacted with the halogenating agent to synthesize the metal complex represented by the formula (M-3), and the step C and the formula (M). The metal complex represented by -3), the compound represented by the formula (M-4), the compound represented by the formula (M-5), the compound represented by the formula (M-6), and the compound represented by the formula (M-6). The metal complex represented by the formula (1-A) can be synthesized by a method including step D in which a coupling reaction is carried out with at least one compound selected from the group consisting of the compounds represented by -7). ..

［式中、
Ｍ^１、ｎ^１、ｎ^２、環Ｒ^１Ａ、環Ｒ^２、Ｅ^１、Ｅ^１１Ａ、Ｅ^１２Ａ、Ｒ^１１Ａ、Ｒ^１２Ａ、Ｒ^１３Ａ及びＡ^１−Ｇ^１−Ａ^２は、前記と同じ意味を表す。
Ｗ^１は、塩素原子、臭素原子又はヨウ素原子を表す。Ｗ^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。
ｎ^Ｗ１は、１以上１０以下の整数を表す。
Ｚ^１は、式（Ｄ−Ａ）で表される基を表す。Ｚ^２は、式（Ｄ−Ｂ）で表される基を表す。Ｚ^３は、式（Ｄ−Ｃ）で表される基を表す。Ｚ^４は、式（Ｄ−Ｄ）で表される基を表す。
Ｗ^２、Ｗ^３、Ｗ^４及びＷ^５は、置換基Ｂ群からなる群から選ばれる基を表す。］

[During the ceremony,
M ¹ , n ¹ , n ² , ring R ^1A , ring R ² , E ¹ , E ^11A , E ^12A , R ^11A , R ^12A , R ^13A and A ^1- G ^1- A ² have the same meaning as above. Represent.
W ¹ represents a chlorine atom, a bromine atom or an iodine atom. If W ¹ is plurally present, they may be the same or different.
n ^W1 represents an integer of 1 or more and 10 or less.
Z ¹ represents a group represented by the formula (DA). Z ² represents a group represented by the formula (DB). Z ³ represents a group represented by the formula (DC). Z ⁴ represents a group represented by the formula (DD).
W ² , W ³ , W ⁴ and W ⁵ represent a group selected from the group consisting of the substituent B group. ]

<Substituent B group>
-B (OR ^C2 ) ₂ (In the formula, ^RC2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. A plurality of ^{RC2s present may be present.} The groups may be the same or different, and may be linked to each other to form a ring structure together with the oxygen atoms to which they are bonded.)
_{-BF 3} A group represented by Q'(where Q'in the formula represents Li, Na, K, Rb or Cs);
-A group represented by MgY'(in the formula, Y'represents a chlorine atom, a bromine atom or an iodine atom);
A group represented by −ZnY'' (wherein Y'' represents a chlorine atom, a bromine atom or an iodine atom; and
-Sn ^(R _{C3) 3} ^{(wherein, R C3} represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. More existing ^{R C3} is A group represented by (), which may be the same or different, and may be linked to each other to form a ring structure together with the tin atoms to which they are bonded.

Examples of the group represented by −B (OR ^C2 ) ₂ include groups represented by the formulas (W-1) to (W-10).

W ¹ is preferably a bromine atom or an iodine atom because the coupling reaction easily proceeds.

n ^W1 is preferably an integer of 1 to 5, more preferably 1 or 2, and even more preferably 1.

W ² , W ³ , W ⁴ and W ⁵ are preferably a group represented by −B (OR ^C2 ) ₂ , and more preferably a group represented by the formula (W-7).

In the coupling reaction, a catalyst such as a palladium catalyst may be used to accelerate the reaction. Examples of the palladium catalyst include palladium acetate, bis (triphenylphosphine) palladium (II) dichloride, tetrakis (triphenylphosphine) palladium (0), and [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium ( II), tris (dibenzylideneacetone) dipalladium (0) can be mentioned.

The palladium catalyst may be used in combination with a phosphorus compound such as triphenylphosphine, tri (o-tolyl) phosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, 1,1'-bis (diphenylphosphine) ferrocene. ..

When a palladium catalyst is used in the coupling reaction, the amount thereof is usually an effective amount, preferably 0.00001 in terms of palladium element, with respect to 1 mol of the compound represented by the formula (M-3). It is 10 mol.

In the coupling reaction, a palladium catalyst and a base may be used in combination, if necessary.

In step C, examples of the halogenating agent include N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide and the like.

In step C, the amount of the halogenating agent is usually 1 to 50 mol with respect to 1 mol of the metal complex represented by the formula (1 ″).

Step A, step B, step C and step D are usually carried out 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, cyclopentylmethyl ether and diglime. Halogen solvents such as methylene chloride and chloroform; nitrile solvents such as acetonitrile and benzonitrile; hydrocarbon solvents such as hexane, decalin, toluene, xylene and mesitylen; N, N-dimethylformamide, N, N-dimethylacetamide And the like; amide-based solvents such as acetone, dimethyl sulfoxide, water and the like.

In Step A, Step B, Step C and Step D, the reaction time is usually between 30 minutes and 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 each reaction described in <Method for producing a metal complex represented by the formula (1-A)> may be used alone or in combination of two or more.

[Host material]
Since the external quantum efficiency of the light emitting device according to the present embodiment is more excellent, the light emitting layer has the metal complex represented by the formula (1-A) and the hole injecting property, the hole transporting property, the electron injecting property and the electron transporting property. It preferably contains a host material having at least one function selected from the group consisting of sexes. When the light emitting layer is a layer containing the metal complex represented by the formula (1-A) and the host material, the host material may be contained alone or in combination of two or more. Good.

When the light emitting layer is a layer containing the metal complex represented by the formula (1-A) and the host material, the content of the metal complex represented by the formula (1-A) is determined by the formula (1-A). ), When the total of the metal complex represented by) and the host material is 100 parts by mass, it is usually 0.1 to 50 parts by mass, preferably 1 to 40 parts by mass, and more preferably 10 to 30 parts by mass. It is a department.

When the light emitting layer is a layer containing the metal complex represented by the formula (1-A) and the host material, the lowest excited triplet state (T ₁ ) of the host material is the light emitting element according to the present embodiment. Since the external quantum efficiency of the above is more excellent, it is preferable that the energy level is equivalent to or higher than _{T 1 of the metal complex represented by the formula (1-A).}

As the host material, since the light emitting element according to the present embodiment can be produced by the solution coating process, it is possible to dissolve the metal complex represented by the formula (1-A) contained in the light emitting layer with respect to the solvent. It is preferable that it exhibits solubility.

The host material is classified into a low molecular weight compound and a high molecular weight compound, and a low molecular weight compound is preferable.

[Small molecule host]
A low molecular weight compound (hereinafter referred to as “low molecular weight host”) preferable as a host material will be described.

The small molecule 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, frill group, benzofuryl. Group, dibenzofuryl group, pyrrolyl group, indolyl group, azaindrill group, carbazolyl group, azacarbazolyl group, diazacarbazolyl group, phenoxadinyl group or phenothiazinyl group is preferable, and phenyl group, spirobifluorenyl group, A pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzothienyl group, a dibenzofuryl group, a carbazolyl group or an azacarbazolyl group is more preferable, and a phenyl group, a pyridyl group, a carbazolyl group or a azacarbazolyl group is more preferable, and the formula (TDA). It is particularly preferable that it is a group represented by -1) or (TDA-3), and it is particularly preferable that it is a group represented by the formula (TDA-3), and these groups have a substituent. May be good.

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 and a cyclo An alkoxy group, an alkoxy group or a cycloalkoxy group is more preferable, an alkyl group or a cycloalkoxy group is further preferable, and these groups may further have a substituent.

n ^H1 is preferably 1. n ^H2 is preferably 0.

n ^H3 is usually 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 further preferably 1.

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

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

L ^H1 has the formulas (A-1) to (A-3), (A-8) to (A-10), (AA-1) to (AA-6), (AA-10) to (AA-). 21) or a group represented by (AA-24) to (AA-34) is preferable, and formulas (A-1), (A-2), (A-8), (A-9), and so on. More preferably, it is a group represented by (AA-1) to (AA-4), (AA-10) to (AA-15) or (AA-29) to (AA-34), and the formula (A). -1), (A-2), (A-8), (A-9), (AA-2), (AA-4), groups represented by (AA-10) to (AA-15) More preferably, the formulas (A-1), (A-2), (A-8), (AA-2), (AA-4), (AA-10), (AA-12) or It is particularly preferable that the group is represented by (AA-14), and is represented by the formulas (A-1), (A-2), (AA-2), (AA-4) or (AA-14). It is particularly preferable that it is a base.

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 and an aryl group are preferable. A group or a monovalent heterocyclic group is more preferable, an alkyl group, an aryl group or a monovalent heterocyclic group is further preferable, and these groups may further have a substituent.

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

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

^RH21 is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

^{The definitions and examples of the aryl group represented by RH21} and the monovalent heterocyclic group are the same as the definitions and examples of the ^{aryl group represented by Ar H1} and Ar ^H2 and the monovalent heterocyclic group.

^{The definitions and examples of substituents that RH21} may have are the same as the definitions and examples of substituents 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).

［式中、Ａｒ^Ｈ１、Ａｒ^Ｈ２、ｎ^Ｈ３及びＬ^Ｈ１は、前記と同じ意味を表す。］

[In the formula, Ar ^H1 , Ar ^H2 , n ^H3 and L ^H1 have the same meanings as described above. ]

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

[Polymer host]
Examples of the polymer compound used as the host material include a polymer compound which is a hole transporting material described later and a polymer compound which is an electron transporting material described later.

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

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

Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these groups are substituted. It may have a group.

The ^{arylene group represented by Ar Y1} is more preferably the formulas (A-1), (A-2), (A-6) to (A-10), (A-19) or (A-20). It is a group represented by, more preferably a group represented by the formulas (A-1), (A-2), (A-7), (A-9) or (A-19). These groups may have substituents.

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

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

Examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" include a group represented by the following formula, which have a substituent. You may be doing it.

［式中、Ｒ^ＸＸは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, ^RXX 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. ]

^RXX is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may 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 the structural units represented by the formulas (Y-1) to (Y-10), which are more excellent in the external quantum efficiency of the light emitting device according to the present embodiment. From the viewpoint, the structural units are preferably represented by the formulas (Y-1) to (Y-3), and from the viewpoint of being more excellent in electron transportability, the formulas (Y-4) to (Y-7) are preferable. It is a structural unit represented by, and from the viewpoint of being more excellent in hole transportability, it is preferably a structural unit represented by the formulas (Y-8) to (Y-10).

［式中、Ｒ^Ｙ１は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ１は、同一でも異なっていてもよく、隣接するＲ^Ｙ１同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[In the formula, ^RY1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. .. A plurality of ^RY1s existing may be the same or different, and adjacent ^RY1s may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

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

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

［式中、Ｒ^Ｙ１１は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ１１は、同一でも異なっていてもよい。］

[In the formula, ^RY11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY11s may be the same or different. ]

^RY11 is preferably an alkyl group, a cycloalkyl group or an aryl group, more preferably an alkyl group or a cycloalkyl group, and these groups may have a substituent.

［式中、Ｒ^Ｙ１は前記と同じ意味を表す。Ｘ^Ｙ１は、−Ｃ（Ｒ^Ｙ２）_２−、−Ｃ（Ｒ^Ｙ２）＝Ｃ（Ｒ^Ｙ２）−又はＣ（Ｒ^Ｙ２）_２−Ｃ（Ｒ^Ｙ２）_２−で表される基を表す。Ｒ^Ｙ２は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Ｙ２は、同一でも異なっていてもよく、Ｒ^Ｙ２同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[In the formula, ^RY1 has the same meaning as described above. X ^{Y1 _{is, -C (R Y2) 2 -}} , - represents a group represented by - C (R Y2) = C (R Y2) - , or _{^{C (R Y2) 2 -C (}} R Y2) 2. ^RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of ^RY2s existing may be the same or different, and the ^RY2s may be bonded to each other to form a ring together with the carbon atoms to which the RY2s are bonded. ]

^RY2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. You may be doing it.

In _{^{X Y1, -C (R Y2)}} 2 - 2 pieces of combinations of ^{R Y2} in the group represented by is preferably both an alkyl group or a cycloalkyl group, both an aryl group, both monovalent heterocyclic A ring group, or one of which is an alkyl or cycloalkyl group and the other of which is an aryl or monovalent heterocyclic group, more preferably one of which is an alkyl or cycloalkyl group and the other of which is an aryl group. May have a substituent. The two existing ^RY2s may be bonded to each other to form a ring with the atoms to which they are bonded, and when ^RY2 forms a ring, as a group represented by ^{−C (RY2} ) _2−. Is preferably a group represented by the formulas (Y-A1) to (Y-A5), more preferably a group represented by the formula (Y-A4), and these groups have a substituent. May be.

In ^{X Y1, -C (R Y2)} = C (R Y2) - 2 pieces of combinations of ^{R Y2} in the group represented by is preferably both an alkyl group or a cycloalkyl group, or, one is an alkyl group Alternatively, it may be a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

In _{^{X Y1, -C (R Y2)}} 2 -C (R Y2) 2 - 4 pieces of ^{R Y2} in the group represented by is preferably an optionally substituted alkyl group or a cycloalkyl group Is. Plural ^{R Y2,} taken together, each may form a ring together with the binding ^{atoms, if R Y2} form a ^{_{ring, -C (R Y2) 2 -C}} (R Y2) 2 - with The group represented is preferably a group represented by the formulas (Y-B1) to (Y-B5), more preferably a group represented by the formula (Y-B3), and these groups are substituted. It may have a group.

［式中、Ｒ^Ｙ２は前記と同じ意味を表す。］

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

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

［式中、Ｒ^Ｙ１及びＸ^Ｙ１は前記と同じ意味を表す。］

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

［式中、Ｒ^Ｙ１及びＸ^Ｙ１は前記と同じ意味を表す。］

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

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

［式中、Ｒ^Ｙ１１及びＸ^Ｙ１は前記と同じ意味を表す。］

[In the formula, ^RY11 and ^XY1 have the same meanings as described above. ]

［式中、Ｒ^Ｙ１は前記と同じ意味を表す。Ｒ^Ｙ３は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, ^RY1 has the same meaning as described above. ^RY3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

^RY3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. You may.

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

［式中、Ｒ^Ｙ１及びＲ^Ｙ３は前記と同じ意味を表す。］

[In the formula, ^RY1 and ^RY3 have the same meanings as described above. ]

［式中、Ｒ^Ｙ１は前記を同じ意味を表す。Ｒ^Ｙ４は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[In the formula, ^RY1 has the same meaning as described above. ^RY4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

^RY4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. You may.

The structural unit represented by the formula (Y) is, for example, a structural unit composed of an arylene group represented by the formulas (Y-101) to (Y-121), and formulas (Y-201) to (Y-206). A structural unit composed of a divalent heterocyclic group represented by, at least one arylene group represented by the formulas (Y-300) to (Y-304) and at least one divalent heterocyclic group. Examples thereof include a structural unit composed of directly bonded divalent groups.

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

A structural unit represented by the formula (Y), in which Ar ^Y1 is a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. The structural unit which is the basis of the above is preferably 0.5 to 40 mol% with respect to the total amount of the structural units contained in the polymer host because the light emitting element according to the present embodiment has excellent charge transportability. More preferably, it is 3 to 30 mol%.

The structural unit represented by the formula (Y) may contain only one type or two or more types in the polymer host.

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

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

[During the ceremony,
a ^X1 and a ^X2 each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^X2 and Ar ^X4 independently form an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. Representing, these groups may have substituents. When ^{there are a plurality of Ar X2} and Ar ^X4 , they may be the same or different.
^RX1 , ^RX2 and ^RX3 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 RX2} and ^RX3 exist, they may be the same or different. ]

Since the external quantum efficiency of the light emitting device according to the present embodiment is more excellent, ^{a X1 is preferably 2 or less, and more preferably 1.}

Since the external quantum efficiency of the light emitting device according to the present embodiment is more excellent, ^{a X2 is preferably 2 or less, and more preferably 0.}

^RX1 , ^RX2 and ^RX3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be good.

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

The ^{divalent heterocyclic groups represented by Ar X1} and Ar ^X3 are more preferably groups represented by the formulas (AA-1), (AA-2) or (AA-7) to (AA-26). Yes, these groups may have substituents.

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

The ^{arylene group represented by Ar X2} and Ar ^X4 is more preferably the formulas (A-1), (A-6), (A-7), (A-9) to (A-11) or (A). It is a group represented by -19), and these groups may have a substituent.

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

A more preferable range of an arylene group and a divalent heterocyclic group in a divalent group in which at least one arylene group represented by Ar ^X2 and Ar ^{X4 and at least one divalent heterocyclic group are directly bonded.} The more preferable range is the same as the more preferable range of the arylene group represented by ^{Ar X1} and Ar ^X3 and the divalent heterocyclic group, respectively, and the further preferable range.

The divalent group in which at least one arylene group represented by ^{Ar X2} and Ar ^X4 and at least one divalent heterocyclic group are directly bonded is at least represented by ^{Ar Y1 of the formula (Y).} Examples thereof include those similar to a divalent group in which one arylene group and at least one divalent heterocyclic group are directly bonded.

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

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

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

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

[In the formula, ^RX4 and ^RX5 are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, halogen atom, monovalent heterocyclic group or cyano. Representing groups, these groups may have substituents. A plurality of ^RX4s may be the same or different. A plurality of ^RX5s existing may be the same or different, and adjacent ^RX5s may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

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

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

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

Examples of the polymer host include the polymer compounds (P-1) to (P-6) in Table 1.

［表中、ｐ、ｑ、ｒ、ｓ及びｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝１００であり、かつ、１００≧ｐ＋ｑ＋ｒ＋ｓ≧７０である。その他の構成単位とは、式（Ｙ）で表される構成単位、式（Ｘ）で表される構成単位以外の構成単位を意味する。］

[In the table, p, q, r, s and t indicate the molar ratio of each structural unit. p + q + r + s + t = 100, and 100 ≧ p + q + r + s ≧ 70. 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, a graft copolymer, and other embodiments, but a plurality of kinds of raw material monomers are used together. It is preferably a copolymer obtained by polymerizing.

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

In the above-mentioned polymerization method, as a method of charging the monomer, a method of charging the entire amount of the monomer in a batch, a method of charging a part of the monomer and reacting, and then collectively charging the remaining monomer. Examples thereof include a method of continuously or separately charging, a method of continuously or separately charging a monomer, and the like.

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

The post-treatment of the polymerization reaction is carried out by a known method, for example, a method of removing water-soluble impurities by liquid separation, a reaction solution after the polymerization reaction is added to a lower alcohol such as methanol, the precipitated precipitate is filtered, and then dried. The method of making the mixture is used alone or in combination. When the purity of the polymer host is low, it can be purified by a usual method such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, or column chromatography.

[Composition of light emitting layer]
The light emitting layer includes a metal complex represented by the formula (1-A), and the above-mentioned host material, hole transport material, hole injection material, electron transport material, electron injection material, and light emitting material (formula (1-A)). A layer containing a composition (hereinafter, also referred to as “light emitting layer composition”) containing at least one material selected from the group consisting of an antioxidant (which is different from the metal complex represented by). There may be.

[Hole transport material]
The hole transporting material is classified into a low molecular weight compound and a high molecular weight compound, and is preferably a high molecular weight compound. The hole transport material may have a cross-linking group.

Examples of low molecular weight compounds include triphenylamine and its derivatives, N, N'-di-1-naphthyl-N, N'-diphenylbenzidine (α-NPD), and N, N'-diphenyl-N, Aromatic amine compounds such as N'-di (m-tolyl) benzidine (TPD) can be mentioned.

Examples of the polymer compound include polyvinylcarbazole and its derivatives; polyarylene having an aromatic amine structure in its side chain or main chain and its derivatives. The polymer compound may be a compound to which an electron accepting site is bound. Examples of the electron-accepting site include fullerenes, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, trinitrofluorenone and the like, and fullerenes are preferable.

When the composition of the light emitting layer contains a hole transporting material, the blending amount of the hole transporting material is usually 1 to 400 mass by mass when the metal complex represented by the formula (1-A) is 100 parts by mass. Parts, preferably 5 to 150 parts by mass.

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

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

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

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

When the composition of the light emitting layer contains an electron transporting material, the blending amount of the electron transporting material is usually 1 to 400 parts by mass when the metal complex represented by the formula (1-A) is 100 parts by mass. Yes, preferably 5 to 150 parts by mass.

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

[Hole injection material and electron injection material]
Hole injection materials and electron injection materials are classified into low molecular weight compounds and high molecular weight compounds, respectively. The hole injection material and the electron injection material may have a cross-linking group.

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

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

When the composition of the light emitting layer contains the hole injection material and the electron injection material, the blending amount of the hole injection material and the electron injection material is 100 parts by mass of the metal complex represented by the formula (1-A), respectively. In the case of, it is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

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

[Ion dope]
When the hole injection material or the electron injection material contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × ^10-5 S / cm to 1 × 10 ^{3 S / cm.} In order to keep the electric conductivity of the conductive polymer within such a range, an appropriate amount of ions can be doped into the conductive polymer.

The type of ion to be doped is an anion in the case of a hole injection material and a cation in the case of an electron injection material. Examples of the anion include polystyrene sulfonate ion, alkylbenzene sulfonate ion, and cerebral sulfonic acid ion. Examples of the cation include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.

The type of ion to be doped may be used alone or in combination of two or more.

[Luminescent material]
Luminescent materials (different from metal complexes represented by formula (1-A)) are classified into low molecular weight compounds and high molecular weight compounds. The luminescent material may have a cross-linking group.

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

Examples of the polymer compound include a phenylene group, a naphthalenediyl group, an anthracendiyl group, a fluorinatedyl group, a phenanthrendiyl group, a dihydrophenanthrenyl group, a group represented by the formula (X), a carbazolediyl group and a phenoxazidinediyl. Examples thereof include high molecular compounds containing a group, a phenothiazinediyl group, a pyrenedyl group and the like.

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

In the composition of the light emitting layer, the blending amount of the light emitting material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, when the metal complex represented by the formula (1-A) is 100 parts by mass. It is a department.

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

[Antioxidant]
The antioxidant may be a compound that is soluble in the same solvent as the metal complex and does not inhibit light emission and charge transport, and examples thereof include phenolic antioxidants and phosphorus-based antioxidants.

When the composition of the light emitting layer contains an antioxidant, the blending amount of the antioxidant is usually 0.001 to 10 mass by mass when the metal complex represented by the formula (1-A) is 100 parts by mass. It is a department.

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

[Ink in the light emitting layer]
The composition containing the metal complex represented by the formula (1-A) and the solvent (hereinafter, also referred to as “ink of the light emitting layer”) includes a spin coating method, a casting method, a micro gravure coating method, and a gravure coating method. Application of method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexo printing method, offset printing method, inkjet printing method, capillary coating method, nozzle coating method, etc. It can be suitably used according to the method.

The viscosity of the ink in the light emitting layer may be adjusted according to the type of coating method, but when a solution such as an inkjet printing method is applied to a printing method via an ejection device, clogging and flight bending occur during ejection. Since it is difficult, it is preferably 1 to 30 mPa · s at 25 ° C.

The solvent contained in the ink of the light emitting layer is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of the solvent include chlorine-based solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; toluene, Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptan, n-octane, n-nonane, n- Aliper hydrocarbon solvents such as decane, n-dodecane and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cell solve acetate, methyl benzoate and phenyl acetate System solvent; Polyhydric alcohol solvent such as ethylene glycol, glycerin, 1,2-hexanediol; Alcohol solvent such as isopropyl alcohol and cyclohexanol; Sulfoxide solvent such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N , N-Dimethylformamide and other amide-based solvents can be mentioned. The solvent may be used alone or in combination of two or more.

In the light emitting layer ink, the amount of the solvent blended is usually 1000 to 100,000 parts by mass, preferably 2000 to 20000 parts by mass, when the metal complex represented by the formula (1-A) is 100 parts by mass. is there.

<Metal complex>
The metal complex according to this embodiment is a metal complex represented by the formula (1-A).

<Membrane>
The membrane contains the metal complex according to this embodiment.

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

The film uses the ink of the light emitting layer, for example, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, It can be produced by a screen printing method, a flexographic printing method, an offset printing method, an inkjet printing method, a capillary coating method, or a nozzle coating method.

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

<Layer structure of light emitting element>
The light emitting element according to the present embodiment has an anode, a cathode, and a light emitting layer provided between the anode and the cathode. The light emitting element according to the present embodiment may further have a substrate.

The light emitting device according to the present embodiment may have layers other than the anode, cathode and light emitting layer (for example, a hole transport layer, an electron transport layer, a hole injection layer, an electron injection layer, etc.).

A preferred embodiment of the light emitting device according to the present embodiment is a light emitting device in which an anode is provided on a substrate, a light emitting layer is laminated on the upper layer thereof, and a cathode is further laminated on the upper layer thereof. Further, another preferable aspect of the light emitting device according to the present embodiment is a light emitting device in which a cathode is provided on a substrate, a light emitting layer is laminated on the upper layer thereof, and an anode is further laminated on the upper layer thereof. In these aspects, a layer having other functions such as a protective layer, a buffer layer, a reflective layer, and a sealing layer (sealing film, sealing substrate, etc.) may be further provided.

The light emitting element according to the present embodiment may be any of a bottom emission type, a top emission type, and a double-sided lighting type.

From the viewpoint of hole injection property and hole transport property, the light emitting device according to the present embodiment preferably has at least one layer of a hole injection layer and a hole transport layer between the anode and the light emitting layer. ..

From the viewpoint of electron injection and electron transportability, the light emitting device according to the present embodiment preferably has at least one layer of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.

Preferred layer configurations of the light emitting device according to the present embodiment include, for example, the following configurations.
(A) Electrono-hole transport layer-light emitting layer-cathode (b) anode-light emitting layer-electron transport layer-cathode (c) anode-hole injection layer-hole transport layer-light emitting layer-cathode (d) anode -Light emitting layer-Electronic transport layer-Electronic injection layer-Catode (e) Anodic-Hole transport layer-Light emitting layer-Electronic injection layer-Conate (f) Anodic-Hole injection layer-Light emitting layer-Electronic transport layer-Conate ( g) anode-hole injection layer-hole transport layer-light emitting layer-electron injection layer-cathode (h) anode-hole injection layer-light emitting layer-electron transport layer-electron injection layer-cathode (i) anode-positive Hole injection layer-hole transport layer-light emitting layer-electron transport layer-electron injection layer-cathode (j) anode-hole transport layer-light emitting layer-electron transport layer-cathode (k) anode-hole injection layer-positive Hole transport layer-Light emitting layer-Electronic transport layer-Catode (l) Electron hole transport layer-Light emitting layer-Electronic transport layer-Electronic injection layer-Conate

The light emitting device according to the present embodiment may be provided with an insulating layer adjacent to the electrode in order to improve the adhesion between the electrode and another layer and improve the charge injection from the electrode. Further, in the light emitting device according to the present embodiment, a thin buffer layer may be inserted at the interface of each layer in order to improve the adhesion of the interface and prevent the components of the two adjacent layers from being mixed. The order and number of layers to be laminated and the thickness of each layer may be adjusted in consideration of external quantum efficiency, device life, and the like.

Next, the configuration of the light emitting element according to the present embodiment will be described in detail.

[substrate]
The light emitting element according to the present embodiment may have a substrate on the side opposite to the light emitting layer side of the anode or on the side opposite to the light emitting layer side of the cathode. The substrate may be one that does not chemically change when an electrode is formed and an organic layer (for example, a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer, etc.) is formed. For example, a substrate made of glass, plastic, a polymer film, a metal film, silicon or the like, and a substrate obtained by laminating these are used.

In the light emitting device according to the present embodiment, the anode, the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron injection layer, and the cathode may be provided with two or more layers, if necessary. Good.

When a plurality of anodes, hole injection layers, hole transport layers, light emitting layers, electron transport layers, electron injection layers and cathodes are present, they may be the same or different from each other.

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

The material used for forming the hole injection layer, the material used for forming the light emitting layer, the material used for forming the hole transport layer, the material used for forming the electron transport layer, and the material used for forming the electron transport layer are the light emitting elements. In the production, when it is dissolved in the solvent used at the time of forming the hole injection layer, the light emitting layer, the hole transport layer, the electron transport layer and the layer adjacent to the electron injection layer, the material is dissolved in the solvent. Is preferably avoided. As a method for avoiding dissolution of the material, i) a method using a material having a cross-linking group, or ii) a method of providing a difference in the solubility of adjacent layers is preferable. In the method of i) above, the layer can be insolubilized by forming a layer using a material having a cross-linking group and then cross-linking the cross-linking group.

[Hole injection layer and electron injection layer]
The hole injection layer is a layer containing a hole injection material. Examples of the hole injection material include the hole injection material that may be contained in the light emitting layer described above. The hole injection material may be contained alone or in combination of two or more.

The electron injection layer is a layer containing an electron injection material. Examples of the electron-injected material include an electron-injected material that may be contained in the above-mentioned light emitting layer. The electron injection material may be contained alone or in combination of two or more.

[Hole transport layer]
The hole transport layer is a layer containing a hole transport material. Examples of the hole transporting material include the hole transporting material that may be contained in the light emitting layer described above. The hole transport material may be contained alone or in combination of two or more.

[Electron transport layer]
The electron transport layer is a layer containing an electron transport material. Examples of the electron transporting material include an electron transporting material that may be contained in the light emitting layer described above. The electron transport material may be contained alone or in combination of two or more.

[electrode]
Examples of the material of the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide and the like. Conductive compounds; composites of silver, palladium and copper (APC); NESA, gold, platinum, silver, copper.

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

In the light emitting device according to the present embodiment, at least one of the anode and the cathode is usually transparent or translucent, but it is preferable that the anode is transparent or translucent.

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

[Manufacturing method of light emitting element]
In the light emitting device according to the present embodiment, as methods for forming each layer such as a light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer, for example, a vacuum vapor deposition method, a spin coating method, and the like. Examples thereof include a coating method typified by an inkjet printing method, and the coating method is preferable. When a low molecular weight compound is used, for example, a vacuum vapor deposition method from powder and a method by forming a film from a solution or a molten state can be mentioned, and when a high molecular compound is used, for example, a film forming from a solution or a molten state is used. The method can be mentioned.

The light emitting layer uses the ink of the light emitting layer, and the hole transport layer, the electron transport layer, the hole injection layer and the electron injection layer are the hole transport material, the electron transport material, the hole injection material and the electron injection material described above. Each of the contained inks can be used for formation by a coating method typified by a spin coating method and an inkjet printing method.

The light emitting element according to the present embodiment can be manufactured, for example, by sequentially laminating each layer on a substrate. Specifically, for example, an anode is provided on the substrate, a layer such as a hole injection layer and a hole transport layer is provided on the substrate, a light emitting layer is provided on the anode, and an electron transport layer and an electron injection layer are provided on the light emitting layer. A light emitting element can be manufactured by providing a layer such as, etc., and further laminating a cathode on the layer. As another manufacturing method, for example, a cathode is provided on a substrate, a layer such as an electron injection layer, an electron transport layer, a light emitting layer, a hole transport layer, and a hole injection layer is provided on the cathode, and further, a layer such as a hole transport layer and a hole injection layer is provided on the cathode. A light emitting element can be manufactured by stacking anodes. As yet another manufacturing method, for example, the anode-side base material in which each layer is laminated on the anode or the anode and the cathode-side base material in which each layer is laminated on the cathode or the cathode are joined to face each other. be able to.

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

Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

In the examples, the polystyrene-equivalent number average molecular weight (Mn) and the polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound are one of the following size exclusion chromatography (SEC) using tetrahydrofuran as the moving layer. Obtained by. The measurement conditions of SEC are as follows.

The polymer compound to be measured was dissolved in tetrahydrofuran at a concentration of about 0.05% by mass, and 10 μL was injected into SEC. The mobile phase was flowed at a flow rate of 0.6 mL / min. As a column, one each of TSKguardvolume SuperAW-H, TSKgel SuperAWM-H, and TSKgel SuperAW3000 (all manufactured by Tosoh) was connected in series and used. A UV-VIS detector (manufactured by Tosoh, trade name: UV-8320GPC) was used as the detector.

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

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

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

A value of high performance liquid chromatography (HPLC) area percentage was used as an index of the purity of the compound. Unless otherwise specified, this value is a value at UV = 254 nm by HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so as to have a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL was injected into HPLC depending on the concentration. For the mobile phase of HPLC, the ratio of acetonitrile / tetrahydrofuran was changed from 100/0 to 0/100 (volume ratio), and the flow 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 Example 1> Compounds CM1 to CM4 and Compound HM-1
Compound CM1 was synthesized according to the method described in JP-A-2010-189630.
Compound CM2 was synthesized according to the method described in JP-A-2008-106241.
Compound CM3 was synthesized according to the method described in JP-A-2010-215886.
Compound CM4 was synthesized according to the method described in International Publication No. 2002/045184.
Compound HM-1 was purchased from Luminescence Technology.

<Synthesis Example 2> Synthesis of polymer compound HTL-1 (Step 1) After the inside of the reaction vessel is made into an inert gas atmosphere, compound CM1 (0.995 g), compound CM2 (0.106 g), and compound CM3 (0. 0924 g), compound CM4 (0.736 g), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) and toluene (50 ml) were added and heated to 105 ° C.
(Step 2) A 20 mass% tetraethylammonium hydroxide aqueous solution (6.6 ml) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 5.5 hours.
(Step 3) Then, phenylboronic acid (24.4 mg), a 20 mass% tetraethylammonium hydroxide aqueous solution (6.6 ml) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (1.8 mg) were added thereto. In addition, it was refluxed for 14 hours.
(Step 4) Then, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling the obtained reaction solution, it was washed twice with water, twice with a 3 mass% acetic acid aqueous solution, and twice with water, and the obtained solution was added dropwise to methanol to cause precipitation. The obtained precipitate was dissolved in toluene and purified by passing the solution in the order of an alumina column and a silica gel column. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred.
The obtained precipitate was collected by filtration and dried to obtain 0.91 g of the polymer compound HTL-1. Mn of the polymer compound HTL-1 is 5.2 × 10 ^4, Mw is of 2.5 × 10 ^5.

In the theoretical value obtained from the amount of the charged raw material, the polymer compound HTL-1 has a structural unit derived from the compound CM1, a structural unit derived from the compound CM2, a structural unit derived from the compound CM3, and a compound. The structural unit derived from CM4 is a copolymer composed of a molar ratio of 50: 5: 5: 40.

<Synthesis Example 3> Synthesis of Polymer Compound ETL-1 (Step 1) Compound M4 (9.23 g) synthesized according to the method described in JP-A-2012-33845 after creating an inert gas atmosphere in the reaction vessel. , Compound CM1 (4.58 g), Dichlorobis (tris-o-methoxyphenylphosphine) palladium (8.6 mg), Methyltrioctyl ammonium chloride (manufactured by Sigma Aldrich, trade name Aliquat 336 (registered trademark)) (0.098 g) And toluene (175 mL) were added and heated to 105 ° C.

(Step 2) Then, a 12 mass% sodium carbonate aqueous solution (40.3 mL) was added dropwise thereto, and the mixture was refluxed for 29 hours.
(Step 3) Then, phenylboronic acid (0.47 g) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (8.7 mg) were added thereto, and the mixture was refluxed for 14 hours.
(Step 4) Then, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. When the obtained reaction solution was cooled and then added dropwise to methanol, precipitation occurred. The precipitate was collected by filtration, washed with methanol and water, and then dried to dissolve the solid in chloroform, which was then passed through an alumina column and a silica gel column which had been previously passed with chloroform for purification. When the obtained purified liquid was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain a polymer compound ETL-1a (7.15 g). The Mn of the polymer compound ETL-1a was 3.2 × 10 ⁴ , and the Mw was 6.0 × 10 ⁴ .
According to the theoretical value obtained from the amount of the charged raw material, the polymer compound ETL-1a is composed of a structural unit derived from the compound M4 and a structural unit derived from the compound CM1 in a molar ratio of 50:50. It is a copolymer.
(Step 5) After setting the inside of the reaction vessel under an argon gas atmosphere, the polymer compounds ETL-1a (3.1 g), tetrahydrofuran (130 mL), methanol (66 mL), and cesium hydroxide monohydrate (2.1 g). And water (12.5 mL) were added, and the mixture was stirred at 60 ° C. for 3 hours.
(Step 6) Then, methanol (220 mL) was added thereto, and the mixture was stirred for 2 hours. After concentrating the obtained reaction mixture, the mixture was added dropwise to isopropyl alcohol and stirred, and a precipitate was formed. The precipitate was collected by filtration and dried to obtain a polymer compound ETL-1 (3.5 g). ¹ H-NMR analysis of the polymer compound ETL-1 confirmed that the signal at the ethyl ester site in the polymer compound ETL-1 disappeared and the reaction was completed.
In the theoretical value obtained from the amount of the raw material charged in the polymer compound ETL-1a, the polymer compound ETL-1 has a structural unit represented by the following formula and a structural unit derived from the compound CM1 at 50:50. It is a copolymer composed of the molar ratio of.

Elemental analysis of the polymer compound ETL-1 was carried out by a combustion method and an atomic absorption method.
The elemental analysis value of the polymer compound ETL-1 is C, 54.1% by mass; H, 5.6% by mass; N, <0.3% by mass; Cs, 22.7% by mass (theoretical value: C, 57.29% by mass; H, 5.70% by mass; Cs, 21.49% by mass; O, 15.52% by mass).

<Comparative Example 1> Synthesis of metal complex MC1

After setting the inside of the reaction vessel to an argon gas atmosphere, the compound MC1-a (33.7 g) and dichloromethane (400 mL) were added, and the reaction vessel was placed in an ice bath and cooled. Then, a 25 mass% aqueous ammonia solution (40.8 g) was added thereto, and the reaction vessel was stirred for 1 hour while cooling in an ice bath. Then, ion-exchanged water (200 mL) and dichloromethane (150 mL) were added thereto, and the organic layer was extracted. The obtained organic layer was dried over anhydrous magnesium sulfate, heptane (400 mL) was added, and dichloromethane was concentrated under reduced pressure to obtain a solution containing a white solid. After filtering the solution containing the obtained white solid, the obtained white solid was dried under reduced pressure to obtain compound MC1-b (27.8 g, yield 93%) as a white solid. The HPLC area percentage value of compound MC1-b was 99.3%. By repeating this operation, the required amount of compound MC1-b was obtained.

TLC / MS (DART, positive): m / z = 150 [M + H] ⁺

After creating an argon gas atmosphere in the reaction vessel, compound MC1-b (34.3 g) and dichloromethane (1.38 L) were added. Then, a dichloromethane solution (1 mol / L, 276 mL) of triethyloxonium tetrafluoroborate was added thereto, and the mixture was stirred at room temperature for 34 hours. Then, an aqueous sodium hydrogen carbonate solution (1 mol / L, 352 mL) was added thereto, and the mixture was stirred at room temperature for 30 minutes. After extracting the organic layer of the obtained reaction solution, the obtained organic layer was washed with saturated brine (300 mL) to obtain an organic layer. After adding heptane (200 mL) to the obtained organic layer, dichloromethane was concentrated under reduced pressure to obtain a solution containing a white solid. After filtering the solution containing the obtained white solid, the obtained filtrate was concentrated to obtain compound MC1-c (33.6 g, yield 82%) as a yellow oil. The HPLC area percentage value of compound MC1-c was 98.0%.

TLC / MS (DART, positive): m / z = 178 [M + H] ⁺

After setting the inside of the reaction vessel to an argon gas atmosphere, the compound MC1-c (33.5 g), benzoyl chloride (26.6 g) and chloroform (570 mL) were added, and then triethylamine (26.4 mL) was added, and 66 at room temperature. Stirred for hours. The obtained reaction solution was concentrated under reduced pressure, ion-exchanged water (210 mL) and chloroform (210 mL) were added to the obtained residue, and the organic layer was extracted. The obtained organic layer was washed with saturated brine (150 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give compound MC1-d (54.2 g, yield 88%) as an orange oil. Obtained. The HPLC area percentage value of compound MC1-d was 86.0%.

TLC / MS (DART, positive): m / z = 282 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CDCl _3- d ₁ ): δ (ppm) = 8.01-7.98 (m, 2H), 7.56-7.51 (m, 1H), 7.46-7 .41 (m, 2H), 7.19 (s, 2H), 7.03 (s, 1H), 4.48-4.41 (m, 2H), 2.23 (s, 6H), 1. 48 (t, 3H).

After setting the inside of the reaction vessel to an argon gas atmosphere, the compound MC1-e (55.8 g) and toluene (925 mL) were added, and the reaction vessel was placed in an ice bath and cooled. Then, an aqueous sodium hydroxide solution (1 mol / L, 222 mL) was added thereto, and the reaction vessel was stirred for 30 minutes while cooling in an ice bath. The organic layer of the obtained reaction solution was extracted to obtain a toluene solution which is an organic layer.
After creating an argon gas atmosphere in the reaction vessel prepared separately, the compounds MC1-d (52.0 g) and chloroform (925 mL) were added, and the reaction vessel was placed in an ice bath and cooled. Then, the toluene solution obtained above was added thereto. Then, the reaction vessel was stirred for 7 hours while cooling in an ice bath, and then stirred at room temperature for 100 hours. Ion-exchanged water (500 mL) was added to the obtained reaction solution, the organic layer was extracted, and the obtained organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (mixed solvent of chloroform and hexane) and then recrystallized using a mixed solvent of chloroform and heptane. Then, the compound MC1-f (17.6 g, yield 22%) was obtained as a white solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of compound MC1-f was 99.5% or more. By repeating this operation, the required amount of compound MC1-f was obtained.

TLC / MS (DART, positive): m / z = 432 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ): δ (ppm) = 7.84 (s, 2H), 7.56-7.54 (m, 2H), 7.43-7.32 (M, 5H), 7.09 (s, 1H), 2.40 (s, 6H), 1.99 (s, 6H).

After setting the inside of the reaction vessel to an argon gas atmosphere, the compound MC1-f (17.3 g), cyclopentyl methyl ether (240 mL) and [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride (98 mg) Was added, and the temperature was raised to 50 ° C. Then, a diethyl ether solution of hexylmagnesium bromide (2 mol / L, 40 mL) was added thereto, and the mixture was stirred at 50 ° C. for 2 hours. Then, an aqueous hydrochloric acid solution (1 mol / L, 80 mL) was added thereto, and the organic layer was extracted. The obtained organic layer was washed twice with ion-exchanged water (100 mL), dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain an oil. Toluene and activated carbon were added to the obtained oil, and the mixture was stirred at 50 ° C. for 30 minutes. Then, it was filtered through a filter covered with silica gel and Celite, and 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 hexane and ethyl acetate) and then recrystallized using methanol. Then, it was dried under reduced pressure at 50 ° C. to obtain 1-g (12.1 g, yield 69%) of compound MC as a white solid. The HPLC area percentage value of compound MC1-g was 99.5% or more.

TLC / MS (DART, positive): m / z = 438 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 7.92 (s, 2H), 7.65-7.62 (m, 2H), 7.48-7.35 ( m, 3H), 7.15 (s, 1H), 7.09 (s, 2H), 2.70 (t, 2H), 2.46 (s, 6H), 2.03 (s, 6H), 1.77-1.67 (m, 2H), 1.46-1.36 (m, 6H), 1.00-0.95 (m, 3H).

After creating an argon gas atmosphere in the reaction vessel, iridium chloride n hydrate (2.50 g), compound MC1-g (6.43 g), ion-exchanged water (28 mL) and 2-ethoxyethanol (112 mL) were added. The mixture was stirred under heating and reflux for 25 hours. Then, toluene was added thereto, and it was washed with ion-exchanged water. The organic layer of the obtained washing liquid was extracted, and 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 toluene and methanol) to obtain a solid (4.82 g).
After setting the inside of the separately prepared reaction vessel to an argon gas atmosphere, the solid (4.81 g), silver trifluoromethanesulfonate (1.43 g), compound MC1-g (4.81 g) and tridecane (1) obtained above were used. .1 mL) was added, and the mixture was heated and stirred at 150 ° C. for 15 hours. Then, toluene was added thereto, and the mixture was filtered through a filter covered with silica gel and Celite, and the obtained filtrate was washed with ion-exchanged water to obtain an organic layer. 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 hexane and toluene) and then recrystallized using a mixed solvent of ethyl acetate and ethanol.
Then, the metal complex MC1 (2.32 g, yield 35%) was obtained as a yellow solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of the metal complex MC1 was 99.5% or more.

LC-MS (APCI, positive): m / z = 1502.8 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 7.96 (s, 6H), 7.07 (s, 6H), 6.91 (s, 3H), 6.60 (T, 3H), 6.51 (t, 3H), 6.41 (d, 3H), 6.29 (d, 3H), 2.70 (t, 6H), 2.09 (s, 18H) , 1.85 (s, 9H), 1.76-1.67 (m, 6H), 1.60 (s, 9H), 1.44-1.35 (m, 18H), 1.00-0 .95 (m, 9H).

<Example 1> Synthesis of metal complex MC2

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC1 (0.50 g), dichloromethane (25 mL) and N-bromosuccinimide (203 mg) were added, and the mixture was stirred at room temperature for 27.5 hours. Then, a 10 mass% sodium sulfite aqueous solution (4.20 g) was added thereto, then ion-exchanged water (8.40 mL) was added, and the mixture was stirred at room temperature for 30 minutes. An organic layer was extracted from the obtained reaction solution, and the obtained organic layer was filtered through a filter laid with silica gel. A precipitate was precipitated by adding methanol to the obtained filtrate. The obtained precipitate was filtered and then vacuum dried at 50 ° C. to obtain a metal complex MC1TBR (0.55 g, yield 95%) as a yellow solid. The HPLC area percentage value of the metal complex MC1TBR was 99.5% or more.

LC-MS (APCI, positive): m / z = 1736.5 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 7.94 (s, 6H), 7.71 (d, 6H), 6.94 (s, 3H), 6.73 -6.70 (m, 3H), 6.29 (d, 3H), 6.25 (d, 3H), 2.72 (t, 6H), 2.10 (s, 18H), 1.84 ( s, 9H), 1.77-1.67 (m, 6H), 1.57 (s, 9H), 1.45-1.34 (m, 18H), 0.99-0.94 (m, 9H).

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC1TBR (0.50 g), the compound MC2-a (0.44 g), toluene (30 mL), tris (dibenzylideneacetone) dipalladium (0) (7.9 mg). ) And 2-dicyclohexylphosphino-2', 6'-dimethoxybiphenyl (8.5 mg) were added, and the temperature was raised to 80 ° C. Then, a 20 mass% tetraethylammonium hydroxide aqueous solution (4.2 mL) was added thereto, and the mixture was stirred under heating under reflux for 6 hours. Then, toluene was added thereto, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter lined with silica gel and Celite, and 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 hexane and toluene) to obtain a metal complex MC2 (0.54 g, yield 74%) as a yellow solid. The HPLC area percentage value of the metal complex MC2 was 99.5% or more.

LC-MS (APCI, positive): m / z = 2523.5 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 8.05 (s (br), 6H), 7.70-7.50 (m, 27H), 7.38 (s) (Br), 6H), 7.13-7.01 (m, 9H), 6.95 (s, 3H), 6.82 (s (br), 3H), 6.65 (s (br), 3H), 2.25 (t, 6H), 2.11 (s, 18H), 2.02 (s, 9H) 1.71-1.64 (m, 9H), 1.48-1.20 ( m, 78H), 0.96-0.86 (m, 9H).

<Example 2> Synthesis of metal complex MC5 (Synthesis Example 2-1) Synthesis of metal complex MC4

After setting the inside of the reaction vessel to an argon gas atmosphere, the compound MC4-a (13.1 g) and tert-butyl methyl ether (110 mL) were added, and the reaction vessel was placed in an ice bath and cooled. Then, an aqueous sodium hydroxide solution (1 mol / L, 125 mL) was added thereto, and the reaction vessel was stirred for 30 minutes while cooling in an ice bath. The organic layer of the obtained reaction solution was extracted to obtain a tert-butyl methyl ether solution.
After creating an argon gas atmosphere in the reaction vessel prepared separately, the compounds MC1-d (11.0 g) and chloroform (220 mL) were added, and the reaction vessel was placed in an ice bath and cooled. Then, the tert-butyl methyl ether solution obtained above was added thereto. Then, the reaction vessel was stirred for 7 hours while cooling in an ice bath, and then stirred at room temperature for 110 hours. Ion-exchanged water (330 mL) was added to the obtained reaction solution, the organic layer was extracted, and the obtained organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (mixed solvent of chloroform and hexane) and then recrystallized using a mixed solvent of chloroform and heptane. Then, the compound MC4-b (10.2 g, yield 55%) was obtained as a white solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of compound MC4-b was 99.5% or more. By repeating this operation, the required amount of compound MC4-b was obtained.

LC-MS (ESI, positive): m / z = 488.2 [M + H] ⁺

^{1 1} H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.92 (s, 2H), 7.66-7.62 (m, 2H), 7.52 (s, 2H), 7 .52-7.36 (m, 3H), 7.16 (s, 1H), 2.57-2.46 (m, 8H), 1.20 (d, 6H), 0.97 (d, 6H) ).

After setting the inside of the reaction vessel to an argon gas atmosphere, compound MC4-b (10.2 g), compound MC2-a (2.8 g), bis [tri (2-methoxyphenyl) phosphine] palladium (II) dichloride (92. 1 mg), toluene (102 mL) and a 20 mass% tetraethylammonium hydroxide aqueous solution (36.9 g) were added, and the mixture was stirred under heating under reflux for 4 hours. Then, toluene was added thereto, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was dried over anhydrous sodium sulfate, silica gel (10 g) was added and filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a solid.
The obtained solid was recrystallized using a mixed solvent of heptane and chloroform. Then, the compound MC4-c (8.55 g, yield 84%) was obtained as a white solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of compound MC4-c was 99.5% or more.

LC-MS (ESI, positive): m / z = 486.3 [M + H] ⁺

^{1 1} H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.96 (s, 2H), 7.75 (t, 4H), 7.60-7.55 (m, 4H), 7 .51-7.41 (m, 4H), 7.17 (s, 1H), 2.63-2.58 (m, 2H), 2.47 (d, 6H), 1.27 (d, 6H) ), 1.05 (d, 6H).

After setting the inside of the reaction vessel to an argon gas atmosphere, add iridium chloride n hydrate (1.96 g), compound MC4-c (5.61 g), ion-exchanged water (20 mL) and jiglime (80 mL) at 150 ° C. The mixture was heated and stirred for 18 hours. Then, toluene was added thereto, and it was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was concentrated under reduced pressure to obtain a solid.
The obtained solid was purified by silica gel chromatography (mixed solvent of toluene and methanol). Then, it was dried under reduced pressure at 50 ° C. to obtain a solid (5.16 g).
After setting the inside of the separately prepared reaction vessel to an argon gas atmosphere, the solid (4.5 g), silver trifluoromethanesulfonate (1.93 g), compound MC4-c (2.78 g), and jiglime (4) obtained above were used. .5 mL), decan (4.5 mL) and 2,6-lutidine (1.1 mL) were added, and the mixture was heated and stirred at 160 ° C. for 31 hours. Then, dichloromethane was added thereto, and the mixture was filtered through a filter lined with Celite, and the obtained filtrate was washed with ion-exchanged water to obtain an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, silica gel (18.6 g) was added and filtered, and 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 cyclohexane and dichloromethane) and then recrystallized using a mixed solvent of toluene and acetonitrile. Then, the metal complex MC4 (1.9 g, yield 24%) was obtained as a yellow solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of the metal complex MC4 was 98.9%.

LC-MS (APCI, positive): m / z = 1646.8 [M + H] ⁺

^{1 1} H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 9.12-7.10 (m, 27H), 7.00 (s, 3H), 6.72 (t, 3H), 6 .62-6.33 (m, 9H), 2.74-1.67 (m, 24H), 1.25 (d, 9H), 1.15-1.00 (m, 18H), 0.84 (D, 9H).

(Synthesis Example 2-2) Synthesis of metal complex MC5

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC4 (0.70 g), dichloromethane (35 mL) and N-bromosuccinimide (825 mg) were added, and the mixture was stirred at room temperature for 40 hours. Then, a 10 mass% sodium sulfite aqueous solution (7.7 g) was added thereto, then ion-exchanged water (15 mL) was added, and the mixture was stirred at room temperature for 30 minutes. An organic layer was extracted from the obtained reaction solution, and the obtained organic layer was filtered through a filter laid with silica gel. A precipitate was precipitated by adding ethanol to the obtained filtrate. The obtained precipitate was filtered and then vacuum dried at 50 ° C. to obtain a metal complex MC4TBR (0.73 g, yield 91%) as a yellow solid. The HPLC area percentage value of the metal complex MC4TBR was 96%. By repeating this operation, the required amount of the metal complex MC4TBR was obtained.

LC-MS (APCI, positive): m / z = 1880.5 [M + H] ⁺

^{1 1} H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 8.25-7.83 (m, 6H), 7.76 (d, 6H), 7.76-7.46 (m, 15H), 7.04 (s, 3H), 6.83 (d, 3H), 6.50 (s, 3H), 6.31 (d, 3H), 2.33-1.85 (m, 24H) ), 1.25 (d, 9H), 1.12-1.07 (m, 18H), 0.84 (d, 9H).

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC4TBR (0.60 g), the compound MC5-a (0.52 g), toluene (18 mL) and bis (di-tert-butyl (4-dimethylaminophenyl) phosphine) ) Dichloropalladium (II) (6.8 mg) was added, and the temperature was raised to 90 ° C. Then, a 20 mass% tetraethylammonium hydroxide aqueous solution (9.1 mL) was added thereto, and the mixture was stirred under heating under reflux for 19 hours. Then, toluene was added thereto, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter laid with silica gel, and 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 cyclohexane and dichloromethane) and then recrystallized using a mixed solvent of toluene and acetonitrile. Then, the metal complex MC5 (0.30 g, yield 47%) was obtained as a yellow solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of the metal complex MC5 was 97.5%.

LC-MS (APCI, positive): m / z = 2001.1 [M + H] ⁺

^{1 1} H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.70-7.40 (m, 27H), 7.04 (s, 3H), 6.78 (s, 9H), 6 .56-6.52 (m, 3H), 6.21 (s, 3H), 2.43-1.88 (m, 42H), 1.75 (s, 9H), 1.23 (d, 9H) ), 1.07-1.01 (m, 18H), 0.85 (d, 9H).

<Example 3> Synthesis of metal complex MC3

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC4TBR (0.31 g), the compound MC2-a (0.31 g), toluene (9.3 mL) and bis (di-tert-butyl (4-dimethylaminophenyl)) ) Phosphine) Dichloropalladium (II) (3.5 mg) was added, and the temperature was raised to 90 ° C. Then, a 20 mass% tetraethylammonium hydroxide aqueous solution (2.7 mL) was added thereto, and the mixture was stirred under heating under reflux for 5 hours. Then, toluene was added thereto, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter laid with silica gel, and 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 cyclohexane and dichloromethane) and then recrystallized using a mixed solvent of dichloromethane and hexane. Then, the metal complex MC3 (0.26 g, yield 60%) was obtained as a yellow solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of the metal complex MC3 was 99.5% or more.

LC-MS (APCI, positive): m / z = 2667.5 [M + H] ⁺

^{1 1} H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 8.40-7.32 (m, 60H), 7.15 (d, 3H), 7.05-7.03 (m, 6H), 6.76 (s, 3H), 2.54-2.50 (m, 3H), 2.18-2.13 (m, 18H), 1.38 (s, 54H), 1.31 -1.13 (m, 30H), 0.90 (d, 9H).

<Comparative Example 2> Synthesis of metal complex MC6

After setting the inside of the reaction vessel to an argon gas atmosphere, the compound MC4-b (17.0 g), cyclopentyl methyl ether (150 mL) and [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride (172 mg) Was added, and the temperature was raised to 50 ° C. Then, a diethyl ether solution of hexylmagnesium bromide (2 mol / L, 35 mL) was added thereto, and the mixture was stirred at 50 ° C. for 5 hours. Then, an aqueous hydrochloric acid solution (1 mol / L, 35 mL) was added thereto, and the organic layer was extracted. The obtained organic layer was washed twice with ion-exchanged water (85 mL), dried over anhydrous magnesium sulfate, filtered, and the obtained filtrate was concentrated under reduced pressure to obtain an oil. Toluene and silica gel were added to the obtained oil, and the mixture was stirred at room temperature for 30 minutes. Then, the mixture was filtered through a filter covered with Celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was recrystallized using acetonitrile. Then, the compound MC6-a (13.7 g, yield 80%) was obtained as a white solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of compound MC6-a was 99.5% or more.

TLC / MS (DART, positive): m / z = 494 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 7.92 (s, 2H), 7.67-7.63 (m, 2H), 7.46-7.33 ( m, 3H), 7.18 (s, 2H), 7.14 (s, 1H), 2.76 (t, 2H), 2.57-2.46 (m, 8H), 1.77-1 .70 (m, 2H), 1.48-1.42 (m, 6H), 1.21-1.19 (m, 6H), 0.98-0.96 (m, 9H).

After creating an argon gas atmosphere in the reaction vessel, iridium chloride trihydrate (2.96 g), compound MC6-a (8.65 g), ion-exchanged water (30 mL) and jiglime (74 mL) were added, and the mixture was heated under reflux. Was stirred for 18 hours. Then, the mixture was cooled to room temperature, toluene was added, and the mixture was washed with ion-exchanged water. The organic layer of the obtained washing liquid was extracted, and 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 toluene and ethanol) to obtain solid MC6-b'(7.51 g).
After setting the inside of the separately prepared reaction vessel to an argon gas atmosphere, the solid MC6-b'(7.40 g), silver trifluoromethanesulfonate (3.19 g), and compound MC6-a (4.59 g) obtained above were obtained. , 2,6-Lutidine (1.66 g) and Decane (15 mL) were added, and the mixture was heated and stirred at 150 ° C. for 20 hours. Then, the mixture was cooled to room temperature, toluene was added, and the mixture was filtered through a filter covered with silica gel and Celite, and the obtained filtrate was washed with ion-exchanged water to obtain an organic layer. 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 dichloromethane and cyclohexane) and then recrystallized using a mixed solvent of toluene and methanol. Then, it was dried under reduced pressure at 50 ° C. to obtain a metal complex MC6-b (1.47 g, yield 14%) as a yellow solid. The HPLC area percentage value of the metal complex MC6-b was 99.4%.

LC-MS (APCI, positive): m / z = 1671.0 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 8.03 (br, 6H), 7.17 (s, 6H), 6.96 (s, 3H), 6.66 (T, 3H), 6.51-6.41 (m, 6H), 6.32 (d, 3H), 2.76 (t, 6H), 2.23-1.92 (m, 21H), 1.76-1.69 (m, 6H), 1.58 (s, 3H), 1.53-1.42 (m, 18H), 1.16 (d, 9H), 1.01-0. 96 (m, 27H), 0.73 (d, 9H).

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC6-b (1.36 g), dichloromethane (68 mL) and N-bromosuccinimide (1.23 g) were added, and the mixture was stirred at room temperature for 32 hours. Then, a 10 mass% sodium sulfite aqueous solution (8.71 g) was added thereto, then ion-exchanged water (70 mL) was added, and the mixture was stirred at room temperature for 30 minutes. An organic layer was extracted from the obtained reaction solution, and the obtained organic layer was filtered through a filter laid with silica gel. The obtained filtrate was concentrated under reduced pressure to give a solid. The obtained solid was dissolved in toluene, and then methanol was added to precipitate a precipitate. The obtained precipitate was filtered and then vacuum dried at 50 ° C. to obtain a metal complex MC6-c (1.47 g, yield 95%) as a yellow solid. The HPLC area percentage value of the metal complex MC6-c was 99.5% or more.

LC-MS (APCI, positive): m / z = 1903.7 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 8.00 (br, 6H), 7.20 (s, 6H), 6.99 (s, 3H), 6.67 (D, 3H), 6.36 (d, 3H), 6.25 (d, 3H), 2.78 (t, 6H), 2.06-1.69 (m, 30H), 1.46- 1.41 (m, 18H), 1.16 (d, 9H), 1.03-0.94 (m, 27H), 0.74 (d, 9H).

After setting the inside of the reaction vessel to an argon gas atmosphere, the metal complex MC6-c (1.30 g), the compound MC6-d (0.44 g), toluene (65 mL) and (di-tert-butyl (4-dimethylaminophenyl)). Phosphine) Dichloropalladium (II) (16 mg) was added, and the temperature was raised to 80 ° C. Then, a 20 mass% tetrabutylammonium hydroxide aqueous solution (23 mL) was added thereto, and the mixture was stirred under heating under reflux for 36 hours. Then, the mixture was cooled to room temperature, toluene was added, and the organic layer was extracted. The obtained organic layer was washed with ion-exchanged water, dried over anhydrous magnesium sulfate, filtered through a filter lined with silica gel and Celite, and 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 dichloromethane and cyclohexane) and then recrystallized using a mixed solvent of ethyl acetate and acetonitrile. Then, the metal complex MC6 (0.93 g, yield 72%) was obtained as a yellow solid by drying under reduced pressure at 50 ° C. The HPLC area percentage value of the metal complex MC6 was 99.5% or more.

LC-MS (APCI, positive): m / z = 20673 [M + H] ⁺

^{1 1} H-NMR (300 MHz, CD ₂ Cl _2- d ₂ ) δ (ppm) = 8.04 (br, 6H), 7.30-7.26 (m, 12H), 7.06-6.98 ( m, 12H), 6.70 (s, 3H), 6.54 (d, 3H), 2.82 (t, 6H), 2.32-1.78 (m, 27H), 1.59-1 .42 (m, 21H), 1.34 (s, 27H), 1.20 (d, 9H), 1.10 (d, 9H), 1.04-0.98 (m, 18H), 0. 73 (d, 9H).

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

(Formation of hole transport layer)
The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.7% by mass. Using the obtained xylene solution, a hole was formed on the hole injection layer by a spin coating method to a thickness of 20 nm, and the holes were heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Compound HM-1 and metal complex MC5 (Compound HM-1 / metal complex MC5 = 75% by mass / 25% by mass) were dissolved in toluene at a concentration of 2% by mass. Using the obtained toluene solution, a film was formed on the hole transport layer to a thickness of 75 nm by a spin coating method, and a light emitting layer was formed by heating at 130 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of electron transport layer)
The polymer compound ETL-P1 was dissolved in 2,2,3,3,4,5,5-octafluoro-1-pentanol at a concentration of 0.25% by mass. Using the obtained 2,2,3,3,4,5,5-octafluoro-1-pentanol solution, a film was formed on the light emitting layer by a spin coating method to a thickness of 10 nm, and nitrogen was formed. An electron transport layer was formed by heating at 130 ° C. for 10 minutes in a gas atmosphere.

(Cathode formation)
After reducing the pressure of the substrate on which the electron transport layer was formed to 1.0 × 10 ^-4 Pa or less in the vapor deposition machine, sodium fluoride was placed on the electron transport layer at about 4 nm as a cathode, and then the sodium fluoride layer was formed. Aluminum was deposited on top by about 80 nm. After the vapor deposition, the light emitting element D1 was manufactured by sealing with a glass substrate.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D1. The external quantum efficiency at 1000 cd / m ² was 8.1% and the CIE chromaticity coordinates (x, y) = (0.15, 0.26). The external quantum efficiency at 5000 cd / m ² was 7.9% and the CIE chromaticity coordinates (x, y) = (0.15, 0.26). The results are shown in Table 2.

<Example D2> Fabrication and evaluation of light emitting element D2 (manufacturing of light emitting element D2)
A light emitting device D2 was produced in the same manner as in Example D1 except that the metal complex MC2 was used instead of the metal complex MC5 in (formation of the light emitting layer) in Example D1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D2. The external quantum efficiency at 1000 cd / m ² was 7.9% and the CIE chromaticity coordinates (x, y) = (0.15, 0.34). The external quantum efficiency at 5000 cd / m ² was 6.6% and the CIE chromaticity coordinates (x, y) = (0.16, 0.34). The results are shown in Table 2.

<Example D3> Fabrication and evaluation of light emitting element D3 (manufacture of light emitting element D3)
A light emitting device D3 was produced in the same manner as in Example D1 except that the metal complex MC3 was used instead of the metal complex MC5 in (formation of the light emitting layer) in Example D1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element D3. The external quantum efficiency at 1000 cd / m ² was 10.7% and the CIE chromaticity coordinates (x, y) = (0.16, 0.37). The external quantum efficiency at 5000 cd / m ² was 9.7% and the CIE chromaticity coordinates (x, y) = (0.16, 0.36). The results are shown in Table 2.

<Comparative Example CD1> Fabrication and evaluation of light emitting element CD1 (manufacture of light emitting element CD1)
A light emitting device CD1 was produced in the same manner as in Example D1 except that the metal complex MC1 was used instead of the metal complex MC5 in (formation of the light emitting layer) in Example D1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element CD1. The external quantum efficiency at 1000 cd / m ² was 2.4% and the CIE chromaticity coordinates (x, y) = (0.16, 0.26). The external quantum efficiency at 5000 cd / m ² was 1.8% and the CIE chromaticity coordinates (x, y) = (0.17, 0.26). The results are shown in Table 2.

<Comparative Example CD2> Fabrication and evaluation of light emitting element CD2 (manufacture of light emitting element CD2)
A light emitting device CD2 was produced in the same manner as in Example D1 except that the metal complex MC6 was used instead of the metal complex MC5 in (formation of the light emitting layer) in Example D1.

(Evaluation of light emitting element)
EL light emission was observed by applying a voltage to the light emitting element CD2. The external quantum efficiency at 1000 cd / m ² was 6.6% and the CIE chromaticity coordinates (x, y) = (0.16, 0.35). The external quantum efficiency at 5000 cd / m ² was 5.5% and the CIE chromaticity coordinates (x, y) = (0.16, 0.35). The results are shown in Table 2.

Claims (11)

With the anode
With the cathode
It has a light emitting layer provided between the anode and the cathode, and has.
A light emitting device in which the light emitting layer contains a metal complex represented by the formula (1-A).

[During the ceremony,
M ¹ 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 ¹ is a rhodium atom or an iridium atom, n ¹ + n ² is 3, and when M ¹ is a palladium atom or a platinum atom, n ¹ + n ² is 2.
Ring R ^1A represents a triazole ring composed of a nitrogen atom, E ¹ , E ^11A , E ^12A and a carbon atom.
Ring R ^2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21A , E ^22A , E ^23A and E ^24A.
E ¹ , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A each independently represent a nitrogen atom or a carbon atom. When a ^{plurality of E 1} , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A exist, they may be the same or different from each other. When E ^11A is a nitrogen atom, R ^11A may or may not be present. When E ^12A is a nitrogen atom, R ^12A may or may not be present. If E ^21A is a nitrogen atom, then R ^21A does not exist. If E ^22A is a nitrogen atom, then R ^22A does not exist. If E ^23A is a nitrogen atom, then R ^23A does not exist. If E ^24A is a nitrogen atom, then R ^24A does not exist.
R ^13A is represented by a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). It is the basis. When a ^{plurality of R 13A} exist, they may be the same or different.
R ^11A , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryloxy group, halogen atom and formula (D). It represents a group represented by −A), a group represented by the formula (DB), a group represented by the formula (DC) or a group represented by the formula (DD), and these groups. May have a substituent. When a ^{plurality of R 11A} , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A exist, they may be the same or different from each other.
However,
Of R ^11A and R ^12A , at least one is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC) or a formula ( It is a group represented by DD) and
At ^{least one of R 21A} , R ^22A , R ^23A and R ^24A is represented by a group represented by the formula (DA), a group represented by the formula (DB), and a group represented by the formula (DC). Is a group or a group represented by the formula (DD) .
At least one of R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A is represented by the group represented by the formula (DA) and the formula (DB). Ri Oh a group represented by the group or the formula (D-C), and,
E ^11A is a nitrogen ^atom, there is ^{R 11A,} when ^{R 11A} is a group represented by the formula (D-D), ^{T DA} in formula (D-D) is an aryl group or a monovalent The substituent which these groups may have is an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent.
A ^1- G ^1- A ² represents an anionic bidentate ligand. A ¹ and A ² 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 ^{there are a plurality of A 1-} G ^1- A ² , they may be the same or different. ]

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

[During the ceremony,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6, and m ^DA7 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. The plurality of G ^DAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, even if these groups have a substituent. Good. When ^{there are a plurality of Ar DA1} , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6, and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. The plurality of ^TDAs may be the same or different. ]

[During the ceremony,
m DA1'represents an integer greater than or ^{equal to 1.}
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. If there are multiple Ar ^DA1 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[In the formula, T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ] The light emitting device according to claim 1, wherein the R ^13A is a group represented by the formula (DC) or a group represented by the formula (DD). The ^{first or second claim, wherein at least one of the R 11A} and the R ^12A is a group represented by the formula (DC) or a group represented by the formula (DD). Light emitting element. The R ^22A is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). The light emitting device according to any one of claims 1 to 3, which is a group represented by). At least one of the R ^11A , the R ^12A , the R ^13A , the R ^21A , the R ^22A , the R ^23A and the R ^24A is a group represented by the formula (DA1), the formula (D-). The light emitting device according to any one of claims 1 to 4, which is a group represented by A2), a group represented by the formula (DA3), or a group represented by the formula (DA4).

[During the ceremony,
R ^p1 , R ^p2 , R ^p3 and R ^p4 independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom. When ^{there are a plurality of R p1} , R ^p2 and R ^p4 , they may be the same or different from each other.
np1 represents an integer from 0 to 5, np2 represents an integer from 0 to 3, np3 represents 0 or 1, and np4 represents an integer from 0 to 4. The plurality of np1s may be the same or different. ] At least one of the R ^11A , the R ^12A , the R ^13A , the R ^21A , the R ^22A , the R ^23A and the R ^24A is a group represented by the formula (D-B1), the formula (D-). The light emitting device according to any one of claims 1 to 4, which is a group represented by B2) or a group represented by the formula (DB3).

[During the ceremony,
R ^p1 , R ^p2 and R ^p3 independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a fluorine atom. When ^{there are a plurality of R p1} and R ^p2 , they may be the same or different from each other.
np1 represents an integer from 0 to 5, np2 represents an integer from 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 from each other. ] At least one of the R ^11A , the R ^12A , the R ^13A , the R ^21A , the R ^22A , the R ^23A and the R ^24A is a group represented by the formula (D-C1), the formula (D-). The light emitting device according to any one of claims 1 to 4, which is a group represented by C2) or a group represented by the formula (D-C3).

[During the ceremony,
R ^p4 and R ^p5 independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom, respectively. When ^{there are a plurality of R p4} and R ^p5 , they may be the same or different from each other.
np4 represents an integer of 0 to 4, and np5 represents an integer of 0 to 5. ] The light emitting device according to any one of claims 1 to 4, wherein the group represented by the formula (DD) is a group represented by the formula (DD1).

[During the ceremony,
R ^p6 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When ^{there are a plurality of R p6s} , they may be the same or different from each other.
np6 represents an integer from 0 to 5. ] Formula metal complex represented by (1-A) is a metal complex body represented by the formula metal complex or the formula represented by (1-A1) (1- A2), of the preceding claims The light emitting element according to any one item.

[In the formula, M ¹ , n ¹ , n ² , R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A , R ^24A and A ^1- G ^1- A ² have the same meanings as described above. .. ] The light emitting device according to any one of claims 1 to 9, wherein the light emitting layer further contains a compound represented by the formula (H-1).

[During the ceremony,
Ar ^H1 and Ar ^H2 each independently represent an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
n ^H1 and n ^H2 independently represent 0 or 1, respectively. When a ^{plurality of n H1s} are present, they may be the same or different. A plurality of n ^H2s may be the same or different.
^{n H3} represents an integer greater than or equal to 0.
L ^H1 represents an arylene group, a divalent heterocyclic group, or ^{a group represented by − [C (RH11} ) ₂ ] n ^H11 −, and these groups may have a substituent. When a ^{plurality of L H1s} exist, they may be the same or different. n ^H11 represents an integer of 1 or more and 10 or less.
^RH11 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
The plurality of ^RH11s present may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which each is bonded.
L ^H2 represents a group represented by −N (−L ^{H21 −RH21) −.} When ^{there are a plurality of L H2s} , 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. ^RH21 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. ] A metal complex represented by the formula (1-A).

[During the ceremony,
M ¹ 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 ¹ is a rhodium atom or an iridium atom, n ¹ + n ² is 3, and when M ¹ is a palladium atom or a platinum atom, n ¹ + n ² is 2.
Ring R ^1A represents a triazole ring composed of a nitrogen atom, E ¹ , E ^11A , E ^12A and a carbon atom.
Ring R ^2A represents a benzene ring, a pyridine ring or a pyrimidine ring composed of two carbon atoms, E ^21A , E ^22A , E ^23A and E ^24A.
E ¹ , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A each independently represent a nitrogen atom or a carbon atom. When a ^{plurality of E 1} , E ^11A , E ^12A , E ^21A , E ^22A , E ^23A and E ^24A exist, they may be the same or different from each other. When E ^11A is a nitrogen atom, R ^11A may or may not be present. When E ^12A is a nitrogen atom, R ^12A may or may not be present. If E ^21A is a nitrogen atom, then R ^21A does not exist. If E ^22A is a nitrogen atom, then R ^22A does not exist. If E ^23A is a nitrogen atom, then R ^23A does not exist. If E ^24A is a nitrogen atom, then R ^24A does not exist.
R ^13A is represented by a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC), or a group represented by the formula (DD). It is the basis. When a ^{plurality of R 13A} exist, they may be the same or different.
R ^11A , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A are independently hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryloxy group, halogen atom and formula (D). It represents a group represented by −A), a group represented by the formula (DB), a group represented by the formula (DC) or a group represented by the formula (DD), and these groups. May have a substituent. When a ^{plurality of R 11A} , R ^12A , R ^21A , R ^22A , R ^23A and R ^24A exist, they may be the same or different from each other.
However,
Of R ^11A and R ^12A , at least one is a group represented by the formula (DA), a group represented by the formula (DB), a group represented by the formula (DC) or a formula ( It is a group represented by DD) and
At ^{least one of R 21A} , R ^22A , R ^23A and R ^24A is represented by a group represented by the formula (DA), a group represented by the formula (DB), and a group represented by the formula (DC). Is a group or a group represented by the formula (DD) .
At least one of R ^11A , R ^12A , R ^13A , R ^21A , R ^22A , R ^23A and R ^24A is represented by the group represented by the formula (DA) and the formula (DB). Ri Oh a group represented by the group or the formula (D-C), and,
E ^11A is a nitrogen ^atom, there is ^{R 11A,} when ^{R 11A} is a group represented by the formula (D-D), ^{T DA} in formula (D-D) is an aryl group or a monovalent The substituent which these groups may have is an alkyl group which may have a substituent or a cycloalkyl group which may have a substituent.
A ^1- G ^1- A ² represents an anionic bidentate ligand. A ¹ and A ² 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 ^{there are a plurality of A 1-} G ^1- A ² , they may be the same or different. ]

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

[During the ceremony,
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6, and m ^DA7 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. The plurality of G ^DAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, even if these groups have a substituent. Good. When ^{there are a plurality of Ar DA1} , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6, and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. The plurality of ^TDAs may be the same or different. ]

[During the ceremony,
m DA1'represents an integer greater than or ^{equal to 1.}
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. If there are multiple Ar ^DA1 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

[In the formula, T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]