JP2017155180A - Polymer compound and light emitting element prepared therewith - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide polymer compounds and compositions useful for the production of light emitting elements having excellent brightness life.SOLUTION: A polymer compound comprises at least one constitutional unit selected from formula (3G), formula (1G), formula (2G), and formula (4G) [M-Mare a group of a metal complex; L-Lindependently represent O, S, an arylene group, a divalent heterocyclic group or the like; Aris an aromatic hydrocarbon group or a heterocyclic group; n, n, and nare an integer of 0 or more].SELECTED DRAWING: None

Description

  The present invention relates to a polymer compound and a light emitting device using the same.

  Light-emitting elements such as organic electroluminescence elements (organic EL elements) can be suitably used for display and illumination applications because of their characteristics such as high luminous efficiency and low-voltage driving, and have recently attracted attention. . As compounds useful for the production of such a light emitting device, Patent Documents 1 and 2 disclose a polymer compound containing a phosphorescent structural unit having a structure of a green phosphorescent compound (for example, a metal complex represented by the following formula). Is described.

International Publication No. 2013/108037 International Publication No. 2013/021180

  However, the light-emitting elements using the polymer compounds described in Patent Documents 1 and 2 for the light-emitting layer have not always had a sufficient luminance life.

  Then, an object of this invention is to provide the high molecular compound etc. which are useful for manufacture of the light emitting element which is excellent in a brightness lifetime.

The present invention provides the following [1] to [13].
[1]
At least selected from the group consisting of a structural unit represented by formula (3G), a structural unit represented by formula (1G), a structural unit represented by formula (2G), and a structural unit represented by formula (4G). A polymer compound containing one type of structural unit.

［式中、
Ｍ^1Gは、式（１）、式（２）又は式（３）で表される基であって、ｎ₁個存在する環Ａ、ｎ₃個存在する環Ｂ¹及びｎ₃個存在する環Ｂ²が有していてもよい結合手、並びに、ｎ₁個ずつ存在するＲ⁵、Ｒ⁶、Ｒ⁷及びＲ⁸が有していてもよい結合手が、合計１つである基を表す。
Ｍ^2Gは、式（１）、式（２）又は式（３）で表される基であって、ｎ₁個存在する環Ａ、ｎ₃個存在する環Ｂ¹及びｎ₃個存在する環Ｂ²が有していてもよい結合手、並びに、ｎ₁個ずつ存在するＲ⁵、Ｒ⁶、Ｒ⁷及びＲ⁸が有していてもよい結合手が、合計２つである基を表す。
Ｍ^3Gは、式（１）、式（２）又は式（３）で表される基であって、ｎ₁個存在する環Ａ、ｎ₃個存在する環Ｂ¹及びｎ₃個存在する環Ｂ²が有していてもよい結合手、並びに、ｎ₁個ずつ存在するＲ⁵、Ｒ⁶、Ｒ⁷及びＲ⁸が有していてもよい結合手が、合計３つである基を表す。
Ｌ¹、Ｌ²及びＬ³は、それぞれ独立に、酸素原子、硫黄原子、−Ｎ（Ｒ^A）−で表される基、−Ｃ（Ｒ^B）₂−で表される基、−Ｃ（Ｒ^B）＝Ｃ（Ｒ^B）−で表される基、−Ｃ≡Ｃ−で表される基、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Aは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Bは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Bは、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。Ｌ¹、Ｌ²及びＬ³が各々複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ^1Mは、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
ｎ^a1、ｎ^b1及びｎ^c1は、それぞれ独立に、０以上の整数を表す。］

[Where:
M ^1G is a group represented by formula (1), formula (2) or formula (3), wherein n ₁ ring A, n ₃ ring B ¹ and n ₃ ring are present. The bond which B ² may have and the bond which R ⁵ , R ⁶ , R ⁷ and R ⁸ each having n ₁ may have represent a group having a total of one bond. .
M ^2G is a group represented by formula (1), formula (2) or formula (3), wherein n ₁ ring A, n ₃ ring B ¹ and n ₃ ring are present. B ² represents a bond which B ² may have, and a bond which R ⁵ , R ⁶ , R ⁷ and R ⁸ each having n ₁ may have have a total of two bonds. .
M ^3G is a group represented by formula (1), formula (2) or formula (3), wherein n ₁ ring A, n ₃ ring B ¹ and n ₃ ring are present. B ² represents a bond that may have and a bond that n ₁ each of R ⁵ , R ⁶ , R ⁷ and R ⁸ may have a total of three bonds. .
L ¹ , L ² and L ³ are each independently an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, —C ( R ^B ) ═C (R ^B ) —, a group represented by —C≡C—, an arylene group or a divalent heterocyclic group, and these groups have a substituent. Also good. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. R ^B represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^B may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. When a plurality of L ¹ , L ² and L ³ are present, they may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
n ^a1 , n ^b1 and n ^c1 each independently represent an integer of 0 or more. ]

［式中、
Ｍは、イリジウム原子又は白金原子を表す。
ｎ₁は、１、２又は３を表す。ｎ₂及びｎ₃は、それぞれ独立に、０、１又は２を表す。Ｍがイリジウム原子の場合、ｎ₁＋ｎ₂＋ｎ₃は３であり、Ｍが白金原子の場合、ｎ₁＋ｎ₂＋ｎ₃は２である。
Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷及びＸ⁸は、それぞれ独立に、窒素原子又は炭素原子を表す。但し、Ｘ⁵、Ｘ⁶、Ｘ⁷及びＸ⁸のうちの少なくとも２つは、炭素原子である。Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷及びＸ⁸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、Ｘ¹が窒素原子の場合、Ｒ¹は存在せず、Ｘ²が窒素原子の場合、Ｒ²は存在せず、Ｘ³が窒素原子の場合、Ｒ³は存在せず、Ｘ⁴が窒素原子の場合、Ｒ⁴は存在せず、Ｘ⁵が窒素原子の場合、Ｒ⁵は存在せず、Ｘ⁶が窒素原子の場合、Ｒ⁶は存在せず、Ｘ⁷が窒素原子の場合、Ｒ⁷は存在せず、Ｘ⁸が窒素原子の場合、Ｒ⁸は存在しない。
Ｒ¹、Ｒ²、Ｒ³及びＲ⁴は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基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。Ｒ¹とＲ²、Ｒ³とＲ⁴は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。Ｒ¹、Ｒ²、Ｒ³及びＲ⁴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。
Ｒ⁵、Ｒ⁶、Ｒ⁷及びＲ⁸は、それぞれ独立に、結合手、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基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。Ｒ⁵とＲ⁶、Ｒ⁶とＲ⁷、Ｒ⁷とＲ⁸は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。Ｒ⁵、Ｒ⁶、Ｒ⁷及びＲ⁸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。
Ｘ^a及びＸ^bの一方は単結合を表し、他方は−ＣＲ¹¹Ｒ¹²−ＣＲ¹³Ｒ¹⁴−で表される基を表す。Ｒ¹¹、Ｒ¹²、Ｒ¹³及びＲ¹⁴は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。但し、Ｒ¹¹、Ｒ¹²、Ｒ¹³及びＲ¹⁴からなる群から選ばれる少なくとも１つは、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基又はハロゲン原子である。Ｒ¹¹とＲ¹²、Ｒ¹³とＲ¹⁴、Ｒ¹¹とＲ¹³、Ｒ¹²とＲ¹⁴は、それぞれ結合して、それぞれが結合する原子とともに環を形成していてもよい。Ｘ^a及びＸ^bが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
環Ａは、それぞれ独立に、５員又は６員の芳香族複素環を表し、該環は結合手を有していてもよく、置換基を有していてもよい。環Ａが複数存在する場合、それらは同一でも異なっていてもよい。
環Ｂ¹は、５員又は６員の芳香族複素環を表し、該環は結合手を有していてもよく、置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｂ¹が複数存在する場合、それらは同一でも異なっていてもよい。
環Ｂ²は、５員又は６員の、芳香族炭化水素環又は芳香族複素環を表し、該環は結合手を有していてもよく、置換基を有していてもよい。該置換基が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。環Ｂ²が複数存在する場合、それらは同一でも異なっていてもよい。
環Ｂ¹が有していてもよい置換基と環Ｂ²が有していてもよい置換基とは、互いに結合して、それぞれが結合する原子とともに環を形成していてもよい。
Ｅ¹及びＥ²は、それぞれ独立に、窒素原子又は炭素原子を表す。Ｅ¹及びＥ²が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。但し、Ｅ¹及びＥ²のうち、少なくとも一方は炭素原子である。
Ａ¹−Ｇ¹−Ａ²は、アニオン性の２座配位子を表す。Ａ¹及びＡ²は、それぞれ独立に、炭素原子、酸素原子又は窒素原子を表し、これらの原子は環を構成する原子であってもよい。Ｇ¹は、単結合、又は、Ａ¹及びＡ²とともに２座配位子を構成する原子団を表す。Ａ¹−Ｇ¹−Ａ²が複数存在する場合、それらは同一でも異なっていてもよい。］
［２］
前記式（１）で表される基が、下記式（１−３）又は式（１−４）で表される基である、［１］に記載の高分子化合物。

[Where:
M represents an iridium atom or a platinum atom.
n ₁ represents ₁ , 2 or 3. n ₂ and n ₃ each independently represents 0, 1 or 2. When M is an iridium atom, n ₁ + n ₂ + n ₃ is 3, and when M is a platinum atom, n ₁ + n ₂ + n ₃ is 2.
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ each independently represent a nitrogen atom or a carbon atom. However, at least two of X ⁵ , X ⁶ , X ⁷ and X ⁸ are carbon atoms. When there are a plurality of X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ , they may be the same or different. However, when X ¹ is a nitrogen atom, R ¹ does not exist, when X ² is a nitrogen atom, R ² does not exist, and when X ³ is a nitrogen atom, R ³ does not exist and X ⁴ is In the case of a nitrogen atom, R ⁴ does not exist, when X ⁵ is a nitrogen atom, R ⁵ does not exist, when X ⁶ is a nitrogen atom, R ⁶ does not exist, and when X ⁷ is a nitrogen atom, R ⁷ does not exist, and when X ⁸ is a nitrogen atom, R ⁸ does not exist.
R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. These groups may have a substituent. R ¹ and R ² , R ³ and R ⁴ may be bonded to each other to form a ring together with the atoms to which they are bonded. When there are a plurality of R ¹ , R ² , R ³ and R ⁴ , they may be the same or different.
R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently a bond, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent heterocyclic group. Or, it represents a halogen atom, and these groups may have a substituent. R ⁵ and R ⁶ , R ⁶ and R ⁷ , and R ⁷ and R ⁸ may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of R ⁵ , R ⁶ , R ⁷ and R ⁸ are present, they may be the same or different.
One of X ^a and X ^b represents a single bond and the other is ^{-CR 11 R 12 -CR 13 R 14} - represents a group represented by. R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. These groups may have a substituent. However, at least one selected from the group consisting of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent heterocyclic ring. A group or a halogen atom. R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , R ¹¹ and R ¹³ , and R ¹² and R ¹⁴ may be bonded to each other to form a ring together with the atoms to which they are bonded. When ^a plurality of X ^a and X ^b are present, they may be the same or different.
Each of the rings A independently represents a 5-membered or 6-membered aromatic heterocyclic ring, and the ring may have a bond or may have a substituent. When a plurality of rings A are present, they may be the same or different.
Ring B ¹ represents a 5-membered or 6-membered aromatic heterocyclic ring, and the ring may have a bond or may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings B ¹ are present, they may be the same or different.
Ring B ² represents a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle, and the ring may have a bond or may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings B ² are present, they may be the same or different.
The substituent that ring B ¹ may have and the substituent that ring B ² may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
E ¹ and E ² each independently represent a nitrogen atom or a carbon atom. When a plurality of E ¹ and E ² are present, they may be the same or different. However, at least one of E ¹ and E ² is a carbon atom.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ]
[2]
The polymer compound according to [1], wherein the group represented by the formula (1) is a group represented by the following formula (1-3) or the formula (1-4).

［式中、
Ｍ、ｎ₁、ｎ₂、ｎ₃、Ｘ¹、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷、Ｘ⁸、Ｒ¹、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＡ¹−Ｇ¹−Ａ²は、前記と同じ意味を表す。
ｍ₁及びｍ₂は、それぞれ独立に、１〜５の整数を表す。ｍ₁及びｍ₂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。
Ｒ¹⁵、Ｒ¹⁶、Ｒ¹⁷及びＲ¹⁸は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基また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。Ｒ¹⁵、Ｒ¹⁶、Ｒ¹⁷及びＲ¹⁸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。］
［３］
前記Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷及びＸ⁸が、炭素原子である、［１］又は［２］に記載の高分子化合物。
［４］
前記環Ａが、置換基を有していてもよいピリジン環、置換基を有していてもよいピリミジン環、置換基を有していてもよいキノリン環、置換基を有していてもよいイソキノリン環、置換基を有していてもよいイミダゾール環又は置換基を有していてもよいトリアゾール環である、［１］〜［３］のいずれかに記載の高分子化合物。
［５］
前記環Ｂ¹が、置換基を有していてもよいピリジン環であり、かつ、前記環Ｂ²が、置換基を有していてもよいベンゼン環である、［１］〜［４］のいずれかに記載の高分子化合物。
［６］
前記式（３Ｇ）で表される構成単位及び前記式（１Ｇ）で表される構成単位からなる群より選ばれる少なくとも１種の構成単位を含む、［１］〜［５］のいずれかに記載の高分子化合物。
［７］
ｎ₃＝０である、［１］〜［６］のいずれかに記載の高分子化合物。
［８］
式（Ｙ）で表される構成単位を更に含む、［１］〜［７］のいずれかに記載の高分子化合物。

[Where:
_{M, n 1, n 2,} n 3, X 1, X 4, X 5, X 6, X 7, X 8, R 1, R 4, R 5, R 6, R 7, R 8, ring A, Ring B ¹ , ring B ² , E ¹ , E ² and A ¹ -G ¹ -A ² represent the same meaning as described above.
m ₁ and m ₂ each independently represents an integer of 1 to 5. When a plurality of m ₁ and m ₂ are present, they may be the same or different.
R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. These groups may have a substituent. When a plurality of R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are present, they may be the same or different. ]
[3]
The polymer compound according to [1] or [2], wherein X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ are carbon atoms.
[4]
The ring A may have a pyridine ring which may have a substituent, a pyrimidine ring which may have a substituent, a quinoline ring which may have a substituent, or a substituent. The polymer compound according to any one of [1] to [3], which is an isoquinoline ring, an imidazole ring which may have a substituent, or a triazole ring which may have a substituent.
[5]
[1] to [4], wherein the ring B ¹ is an optionally substituted pyridine ring, and the ring B ² is an optionally substituted benzene ring. The high molecular compound in any one.
[6]
In any one of [1] to [5], including at least one structural unit selected from the group consisting of the structural unit represented by the formula (3G) and the structural unit represented by the formula (1G). High molecular compound.
[7]
The polymer compound according to any one of [1] to [6], wherein n ₃ = 0.
[8]
The polymer compound according to any one of [1] to [7], further comprising a structural unit represented by the formula (Y).

［式中、Ａｒ^Y1は、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。］
［９］
架橋基Ａ群から選ばれる少なくとも１つの架橋基を有する構成単位を更に含む、［１］〜［８］のいずれかに記載の高分子化合物。
（架橋基Ａ群）

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ]
[9]
The polymer compound according to any one of [1] to [8], further comprising a structural unit having at least one crosslinking group selected from the crosslinking group A group.
(Crosslinking group A group)

［式中、Ｒ^XLは、メチレン基、酸素原子又は硫黄原子を表す。ｎ^XLは、０〜５の整数を表す。Ｒ^XLが複数存在する場合、それらは同一でも異なっていてもよく、ｎ^XLが複数存在する場合、それらは同一でも異なっていてもよい。＊１は結合位置を表す。これらの架橋基は置換基を有していてもよい。］
［１０］
前記架橋基を有する構成単位が、前記式（ＸＬ−１７）で表される架橋基を有する構成単位である、［９］に記載の高分子化合物。
［１１］
［１］〜［１０］のいずれかに記載の高分子化合物と、
正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料、酸化防止剤及び溶媒からなる群より選ばれる少なくとも１種の材料とを含有する組成物。
［１２］
［１］〜［１０］のいずれかに記載の高分子化合物又はその架橋体を含む発光素子。

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom. n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * 1 represents a binding position. These crosslinking groups may have a substituent. ]
[10]
[9] The polymer compound according to [9], wherein the structural unit having a crosslinking group is a structural unit having a crosslinking group represented by the formula (XL-17).
[11]
[1] to the polymer compound according to any one of [10],
A composition comprising a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and at least one material selected from the group consisting of a solvent.
[12]
The light emitting element containing the high molecular compound in any one of [1]-[10], or its crosslinked body.

ADVANTAGE OF THE INVENTION According to this invention, the polymer compound etc. which are useful for manufacture of the light emitting element which is excellent in the brightness lifetime can be provided. Furthermore, the polymer compound according to a preferred embodiment of the present invention is excellent in color purity.
When a light emitting device containing a polymer compound or the like according to a preferred embodiment of the present invention is used in combination with a color filter, or when the cavity of a light emitting device containing the polymer compound or the like is adjusted, the external quantum efficiency or luminance lifetime is further increased. It will be excellent.

FIG. 11 shows emission spectra at 100 cd / m ² of the light-emitting element D1, the light-emitting element D2, the light-emitting element D3, and the light-emitting element CD1.

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

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

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

  In the present specification, the hydrogen atom may be a deuterium atom.

  In this specification, a solid line representing a bond with a central metal in a structural formula representing a metal complex means a covalent bond or a coordinate bond.

“Polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ to 1 × 10 ⁸ . The structural unit contained in the polymer compound is 100 mol% in total.

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

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

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

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

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

“Aryl group” means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The carbon atom number of an aryl group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-20, More preferably, it is 6-10.
The aryl group may have a substituent, for example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a 2-anthracenyl group, a 9-anthracenyl group, a 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups Are groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

The “alkoxy group” may be linear or branched. The carbon atom number of a linear alkoxy group is 1-40 normally without including the carbon atom number of a substituent, Preferably it is 4-10. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The alkoxy group and the cycloalkoxy 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, Examples include hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, 3,7-dimethyloctyloxy, and lauryloxy.

The number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 7 to 48, not including the number of carbon atoms of the substituent.
The aryloxy group may have a substituent, for example, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples 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.

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

The number of carbon atoms of the monovalent heterocyclic group is usually 2 to 60, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these And 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.

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

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

The “alkenyl group” may be linear or branched. The carbon atom number of a linear alkenyl group is 2-30 normally without including the carbon atom number of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkenyl group and the cycloalkenyl group may have a substituent, for example, vinyl group, 1-propenyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 3-pentenyl group, 4- Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.

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

The “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The carbon atom number of an arylene group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-30, More preferably, it is 6-18.
The arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formula (A-1) to formula (A-20) are preferable. The arylene group includes a group in which a plurality of these groups are bonded.

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

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

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

［式中、Ｒ及びＲ^aは、前記と同じ意味を表す。］

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

  The “crosslinking group” is a group capable of generating a new bond by being subjected to heat treatment, ultraviolet irradiation treatment, radical reaction, or the like, and is preferably a group represented by formulas (B-1) and (B-2). ), (B-3), (B-4), (B-5), (B-6), (B-7), (B-8), (B-9), (B-10), It is a group represented by (B-11), (B-12), (B-13), (B-14), (B-15), (B-16) or (B-17).

［式中、これらの基は置換基を有していてもよい。］

[In the formula, these groups may have a substituent. ]

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

  “Dendron” means a group having a regular dendritic branch structure (ie, a dendrimer structure) having an atom or ring as a branch point. Examples of the compound having dendron (hereinafter referred to as “dendrimer”) include, for example, International Publication No. 2002/066733, Japanese Patent Application Laid-Open No. 2003-231692, International Publication No. 2003/079736, International Publication No. 2006/097717. And the structure described in the literature.

  The dendron is preferably a group represented by the formula (DA) or (DB).

［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。］

[Where:
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 optionally have a substituent. When there are a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

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

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

m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably 0 or 1. m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are preferably the same integer.

G ^DA is preferably a group represented by the formula (GDA-11) ~ (GDA -15), these groups may have a substituent.

［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。］

[Where:
* Is, Ar ^DA1 in the formula (D-A), formula (D-B) in Ar ^DA1, formula (D-B) Ar in ^DA2, or represents a bond between Ar ^DA3 in the formula (D-B).
** is, Ar ^DA2 in Formula (D-A), Ar ^DA2 in the formula (D-B), Ar in the formula (D-B) ^DA4, or represents a bond between Ar ^DA6 in the formula (D-B) .
*** is, Ar ^DA3 in the formula (D-A), Ar ^DA3 in the formula (D-B), Ar ^DA5 in the formula (D-B), or, the bond between Ar ^DA7 in the formula (D-B) Represent.
R ^DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of ^RDA , they may be the same or different. ]

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

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably groups represented by the formulas (ArDA-1) to (ArDA-3).

［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。］

[Where:
R ^DA represents the same meaning as described above.
R ^DB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are a plurality of ^RDBs , they may be the same or different. ]

R ^DB is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, and still more preferably an aryl group.

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

［式中、Ｒ^DA及びＲ^DBは前記と同じ意味を表す。］

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

  The group represented by the formula (DA) is preferably a group represented by the formulas (D-A1) to (D-A3).

［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ハロゲン原子を表す。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を表す。複数あるｎｐ１は、同一でも異なっていてもよい。］

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

  The group represented by the formula (D-B) is preferably a group represented by the formulas (D-B1) to (D-B3).

［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ハロゲン原子を表す。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。］

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

  np1 is preferably an integer of 0 to 3, more preferably an integer of 1 to 3, and even more preferably 1. np2 is preferably 0 or 1, more preferably 0. np3 is preferably 0.

R ^p1 , R ^p2 and R ^p3 are preferably an alkyl group or a cycloalkyl group.

<Polymer compound>
The polymer compound of the present invention includes a structural unit represented by the formula (3G), a structural unit represented by the formula (1G), a structural unit represented by the formula (2G), and a structure represented by the formula (4G). It includes at least one structural unit selected from the group consisting of units (that is, a structural unit having the structure of a phosphorescent compound).

  Since the polymer compound of the present invention has excellent luminance life of a light emitting device using the polymer compound of the present invention, the group consisting of the structural unit represented by the formula (3G) and the structural unit represented by the formula (1G) It is preferable to include at least one structural unit selected from the above, and it is more preferable to include a structural unit represented by the formula (3G).

-Phosphorescent compound "Phosphorescent compound" means a compound that exhibits phosphorescence, and is preferably a metal complex that emits light from a triplet excited state. This metal complex that emits light from a triplet excited state has a central metal atom and a ligand.

  As the central metal atom, a metal atom having an atomic number of 40 or more and having a spin-orbit interaction in the complex and capable of causing an intersystem crossing between a singlet state and a triplet state is exemplified. Examples of the metal atom include a ruthenium atom, a rhodium atom, a palladium atom, an iridium atom, and a platinum atom.

  As the ligand, a neutral or anionic monodentate ligand that forms at least one bond selected from the group consisting of a coordination bond and a covalent bond with the central metal atom, or neutral Or an anionic polydentate ligand is illustrated. Examples of the bond between the central metal atom and the ligand include a metal-nitrogen bond, a metal-carbon bond, a metal-oxygen bond, a metal-phosphorus bond, a metal-sulfur bond, and a metal-halogen bond. The multidentate ligand usually means a bidentate to hexadentate ligand.

Phosphorescent compounds are available from Aldrich, Luminescence Technology Corp. Available from the American Dye Source.
In addition to the methods described above, “Journal of the American Chemical Society, Vol. 107, 1431-1432 (1985)”, “Journal of the American Chemical Society, Vol. 106, 6664, 66, 664”. It can also be produced by a known method described in documents such as Japanese Patent Publication No. 2011/024761, International Publication No. 2002/44189, and Japanese Patent Application Laid-Open No. 2006-188673.

The maximum peak wavelength of the emission spectrum of the phosphorescent compound is obtained by dissolving the phosphorescent compound in an organic solvent such as xylene, toluene, chloroform, tetrahydrofuran, etc. to prepare a dilute solution (1 × 10 ⁻⁶ to 1 × 10 ^{− 3} % by weight) and can be evaluated by measuring the PL spectrum of the diluted solution at room temperature. Xylene is preferred as the organic solvent for dissolving the phosphorescent compound.

  -The structural unit represented by the formula (3G)

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

n ^b1 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably 0. .

M ^2G is preferably a group represented by the formula (1).

  In the polymer compound of the present invention, the structural unit represented by the formula (3G) may be contained singly or in combination of two or more, but is preferably contained alone. .

  The content of the structural unit represented by the formula (3G) is usually 0.01 to 99 with respect to the total amount of the structural units contained in the polymer compound because the luminance life of the light emitting device of the present invention is more excellent. It is mol%, Preferably it is 0.1-70 mol%, More preferably, it is 1-50 mol%, More preferably, it is 5-30 mol%, Most preferably, it is 7-10 mol%.

  -The structural unit represented by the formula (1G)

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

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

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

Definitions and examples of the substituent that R ^A , R ^B, and L ¹ may have are the same as the definitions and examples of the substituent that the ring R ^1B and ring R ^2B may have.

^na1 is usually an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably 0. .

M ^1G is preferably a group represented by the formula (1).

  In the polymer compound of the present invention, the structural unit represented by the formula (1G) may be contained singly or in combination of two or more, but is preferably contained alone. .

  The content of the structural unit represented by the formula (1G) is usually 0.005 to 7 with respect to the total amount of the structural units contained in the polymer compound because the luminance life of the light emitting device of the present invention is more excellent. It is mol%, Preferably it is 0.01-5 mol%, More preferably, it is 0.05-3 mol%, More preferably, it is 0.1-2 mol%.

  <Structural Unit Represented by Formula (2G)>

The preferred range of M ^1G is the same as the preferred range of M ^1G in formula (1G) described above, examples and preferable range of L ² and n ^b1 are examples of L ² and n ^b1 in the preceding formulas (3G) And the same as the preferred range.

L ³ is preferably —C (R ^B ) ₂ —, an arylene group or a divalent heterocyclic group, more preferably —C (R ^B ) ₂ — or an arylene group, and an arylene group. It is further more preferable, and it is especially preferable that it is group represented by a formula (A-1) or (A-2), and these groups may have a substituent.

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

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

  In the polymer compound of the present invention, the structural unit represented by the formula (2G) may be contained singly or in combination of two or more, but is preferably contained alone. .

  The content of the structural unit represented by the formula (2G) is usually 0.01 to 99 with respect to the total amount of the structural units contained in the polymer compound because the luminance life of the light emitting device of the present invention is more excellent. It is mol%, Preferably it is 0.1-70 mol%, More preferably, it is 1-50 mol%, More preferably, it is 5-30 mol%.

  -The structural unit represented by the formula (4G)

Examples and preferred ranges of L ² and n ^b1 are the same as examples and preferred ranges of L ² and n ^b1 in the preceding formulas (3G).

M ^3G is preferably a group represented by the formula (1).

  In the polymer compound of the present invention, the structural unit represented by the formula (4G) may be contained singly or in combination of two or more, but is preferably contained alone. .

  The content of the structural unit represented by the formula (4G) is usually 0.01 to 99 with respect to the total amount of the structural units contained in the polymer compound because the luminance life of the light emitting device of the present invention is more excellent. It is mol%, Preferably it is 0.1-70 mol%, More preferably, it is 1-50 mol%, More preferably, it is 5-30 mol%.

· M ^1G, group M ^1G represented by M ^2G and M ^3G, the group represented by M ^2G and M ^3G is a group formed by removing one to three hydrogen atoms from the phosphorescent compound is a metal complex And is a group represented by formula (1), formula (2) or formula (3).

  In Formula (1), Formula (2), and Formula (3), M is preferably an iridium atom because the luminance life of the light emitting device of the present invention is excellent.

In formula (1), formula (2) and formula (3), E ¹ and E ² are preferably carbon atoms because the luminance life of the light emitting device of the present invention is excellent.

In Formula (1), Formula (2), and Formula (3), n ₂ is preferably 0 because the luminance life of the light emitting device of the present invention is more excellent.

In Formula (1), Formula (2), and Formula (3), n ₃ is preferably 1 or 2, and more preferably 2, because the luminance life of the light emitting device of the present invention is more excellent.

In the formula (1), formula (2) and formula (3), examples of the anionic bidentate ligand represented by A ¹ -G ¹ -A ² include ligands represented by the following formula: Is mentioned.

［式中、＊は、イリジウム原子又は白金原子と結合する部位を表す。］

[In formula, * represents the site | part couple | bonded with an iridium atom or a platinum atom. ]

In formula (1), formula (2) and formula (3), the anionic bidentate ligand represented by A ¹ -G ¹ -A ² may be a ligand represented by Good.

［式中、
＊は、イリジウム原子又は白金原子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、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。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。Ｒ^L2が複数存在する場合、それらは同一でも異なっていてもよい。］

[Where:
* Represents the site | part couple | bonded with an iridium atom or a platinum atom.
R ^L1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent. A plurality of R ^L1 may be the same or different.
R ^L2 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, or a halogen atom, and these groups optionally have a substituent. When a plurality of R ^L2 are present, they may be the same or different. ]

Examples of the group represented by M ^2G are represented by the following formulas (Ir-2G-1) to (Ir-2G-6) or (Pt-2G-1) to (Pt-2G-3). Groups. Among these, since the luminance lifetime of the light emitting device of the present invention is excellent, groups represented by formulas (Ir-2G-1) to (Ir-2G-6) are preferable, and formulas (Ir-2G-1) to ( Groups represented by Ir-2G-4) are more preferred, groups represented by formulas (Ir-2G-1) to (Ir-2G-2) are more preferred, and represented by formula (Ir-2G-1) Particularly preferred are the groups

［式中、Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷、Ｘ⁸、Ｘ^a、Ｘ^b、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹及びＥ²は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ^a , X ^b , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R] ⁶ , R ⁷ , R ⁸ , Ring A, Ring B ¹ , Ring B ² , E ¹ and E ² represent the same meaning as described above. ]

Examples of the group represented by M ^1G are represented by the following formulas (Ir-1G-1) to (Ir-1G-6) or (Pt-1G-1) to (Pt-1G-3). Groups. Among these, since the luminance lifetime of the light emitting device of the present invention is excellent, groups represented by the formulas (Ir-1G-1) to (Ir-1G-6) are preferable, and the formulas (Ir-1G-1) to ( A group represented by formula (Ir-1G-1) to (Ir-1G-2) is more preferred, and a group represented by formula (Ir-1G-1) is more preferred. Particularly preferred are the groups

［式中、Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷、Ｘ⁸、Ｘ^a、Ｘ^b、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹及びＥ²は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ^a , X ^b , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R] ⁶ , R ⁷ , R ⁸ , Ring A, Ring B ¹ , Ring B ² , E ¹ and E ² represent the same meaning as described above. ]

Examples of the group represented by M ^3G include groups represented by the following formulas (Ir-3G-1) to (Ir-3G-6). Among these, since the luminance lifetime of the light emitting device of the present invention is excellent, groups represented by the formulas (Ir-3G-4) to (Ir-3G-6) are more preferable, and in the formula (Ir-3G-4) The group represented is more preferred.

［式中、Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷、Ｘ⁸、Ｘ^a、Ｘ^b、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹及びＥ²は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ , X ^a , X ^b , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R] ⁶ , R ⁷ , R ⁸ , Ring A, Ring B ¹ , Ring B ² , E ¹ and E ² represent the same meaning as described above. ]

M ^1G , M ^2G, and M ^3G (particularly M ^1G and M ^2G ) are excellent in luminance lifetime of the light-emitting element of the present invention, and thus have formulas (Ir-2G-1) to (Ir-2G-6) or formulas The groups represented by (Ir-1G-1) to (Ir-1G-6) are more preferred, and are represented by the formulas (Ir-2G-1) to (Ir-2G-4) or the formula (Ir-1G- It is more preferable that it is group represented by 1)-(Ir-1G-4), Formula (Ir-2G-1)-(Ir-2G-2) or Formula (Ir-1G-1)-(Ir Is particularly preferably a group represented by the formula (Ir-2G-1) or the formula (Ir-1G-1).

In the formula (1), formula (2) and formula (3), X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ represent the synthesis of the polymer compound of the present invention. Since it becomes easy, it is preferable that it is a carbon atom.

In the formula (1), formula (2) and formula (3), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ represent the synthesis of the polymer compound of the present invention. In order to facilitate, it is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, An atom or an alkyl group is more preferable, and a hydrogen atom is particularly preferable.

In formula (1), formula (2) and formula (3), the luminance life of the light emitting device of the present invention is excellent,
R ¹ and R ⁸ are preferably a hydrogen atom or an alkyl group,
R ¹ , R ² and R ⁸ are a hydrogen atom or an alkyl group, R ¹ , R ⁶ and R ⁸ are a hydrogen atom or an alkyl group, or R ¹ , R ⁷ and R ⁸ are a hydrogen atom or More preferably an alkyl group,
More preferably, R ¹ , R ² , R ⁶ and R ⁸ are hydrogen atoms or alkyl groups, or R ¹ , R ² , R ⁷ and R ⁸ are hydrogen atoms or alkyl groups,
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are particularly preferably a hydrogen atom or an alkyl group.

Equation (1), wherein (2) and (3), R ^5, if R ^6, R ⁷ or R ⁸ is a bond, because the synthesis of the polymer compound of the present invention is facilitated, R ⁶ Alternatively, R ⁷ is preferably a bond, and R ⁷ is more preferably a bond.

In formula (1), formula (2) and formula (3), ring A and ring B ¹ are preferably 6-membered aromatic heterocycles having 1 to 4 nitrogen atoms as constituent atoms. More preferably, it is a 6-membered aromatic heterocyclic ring having 1 or more and 2 or less nitrogen atoms as constituent atoms, and these rings may have a substituent.

In formula (1), formula (2) and formula (3), ring B ² is preferably a 6-membered aromatic hydrocarbon ring or a 6-membered aromatic heterocycle, and is a 6-membered aromatic hydrocarbon. More preferably, they are rings, and these rings may have a substituent.

In the formula (1), the formula (2) and the formula (3), the aromatic heterocyclic ring represented by the ring A, the ring B ¹ and the ring B ² is excellent in the luminance life of the light-emitting element of the present invention. Ring, pyrimidine ring, quinoline ring, isoquinoline ring, imidazole ring or triazole ring is preferred, pyridine ring, pyrimidine ring, imidazole ring or triazole ring is more preferred, pyridine ring, pyrimidine ring or triazole ring is more preferred, and pyridine ring is particularly preferred Preferably, these rings may have a substituent. When ring A has a plurality of substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded. When ring B ¹ or ring B ² has a plurality of substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.

In the formula (1), the formula (2) and the formula (3), the aromatic hydrocarbon ring represented by the ring B ² is excellent in the luminance life of the light emitting device of the present invention, so that a benzene ring, a naphthalene ring, a fluorene Ring, phenanthrene ring, indene ring, pyridine ring, diazabenzene ring, pyrrole ring, furan ring and thiophene ring are preferred, benzene ring, naphthalene ring, fluorene ring, pyridine ring or pyrimidine ring are more preferred, benzene ring, pyridine ring or pyrimidine ring Rings are more preferable, benzene rings are particularly preferable, and these rings may have a substituent. When ring B ² has a plurality of substituents, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which they are bonded.

In formula (1), formula (2) and formula (3), ring B ¹ may be a pyridine ring which may have a substituent, and ring B ² may have a substituent. A good benzene ring is particularly preferred.

In formula (1), formula (2) and formula (3), when ring A, ring B ¹ or ring B ² has a substituent, the substituent is soluble in the solvent of the polymer compound of the present invention. And an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is preferable, and an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable. Are more preferable, an alkyl group, a cycloalkyl group or an aryl group is more preferable, an alkyl group or an aryl group is particularly preferable, and an aryl group is particularly preferable.

In the formula (1), formula (2) and formula (3), when the substituent of the ring A, ring B ¹ or ring B ² is dendron, the luminance lifetime of the light-emitting element of the present invention is excellent. D-A) or a group represented by the formula (D-B) is preferred, a group represented by the formula (D-A1) or the formula (D-B1) is preferred, and the formula (D- A group represented by A1) is more preferable.

  In the formula (1), formula (2) and formula (3), examples of the aromatic heterocycle represented by the ring A include the following formulas (E-1) to (E-15) and the following formula (F- Examples include rings represented by 1) to (F-15). Among these, since the synthesis | combination of the high molecular compound of this invention becomes easy, the ring represented by Formula (E-1)-(E-4) or Formula (F-1)-(F-13) is preferable. Since the luminance life of the light emitting device of the present invention is excellent, the rings represented by formulas (E-1) to (E-3) or formulas (F-2) to (F-6) are more preferable. -2), a ring represented by formula (E-3) or formula (F-6) is more preferred, and a ring represented by formula (E-2) is particularly preferred.

［式中、
＊は、イリジウム原子又は白金原子と結合する部位を表す。
＊＊は、Ｘ¹及びＸ⁴を構成原子に有する芳香環、Ｘ³及びＸ⁴を構成原子に有する芳香環、又は、Ｘ¹及びＸ²を構成原子に有する芳香環と結合する部位を表す。
Ｒ^L3は、結合手、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、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。Ｒ^L3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^L4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、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。］

[Where:
* Represents the site | part couple | bonded with an iridium atom or a platinum atom.
** represents an aromatic ring having X ¹ and X ⁴ as constituent atoms, an aromatic ring having X ³ and X ⁴ as constituent atoms, or a site bonded to an aromatic ring having X ¹ and X ² as constituent atoms. .
R ^L3 represents a bond, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups optionally have a substituent. When a plurality of R ^L3 are present, they may be the same or different.
R ^L4 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. ]

In formulas (E-1) to (E-15) and formulas (F-1) to (F-15), R ^L3 represents an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group. Are preferred, more preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, and even more preferably an aryl group.

In formulas (E-1) to (E-15) and formulas (F-1) to (F-15), R ^L4 is preferably an alkyl group, a cycloalkyl group, an aryl group or a substituted amino group, More preferably, it is an alkyl group or an aryl group.

When ring A has a bond, in formulas (E-1) to (E-15) and formulas (F-1) to (F-15), R ^L3 has a bond, or R ^L3 is A bond is preferable, and R ^L3 is more preferably a bond.

In the formula (1), formula (2) and formula (3), examples of the ligand constituted by the ring B ¹ and the ring B ² include the following formulas (J-1) to (J-16). The ligand represented is mentioned. Among these, since the luminance lifetime of the light emitting device of the present invention is excellent, the ligands represented by the formulas (J-1) to (J-8) are preferable, and the formulas (J-1) to (J-3) are preferable. A ligand represented by formula (J-1) or a formula (J-2) is more preferred, and a ligand represented by formula (J-1) is particularly preferred. preferable.

［式中、
＊は、イリジウム原子又は白金原子と結合する部位を表す。
Ｒ^L5及びＲ^L6は、結合手、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、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。Ｒ^L5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^L7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、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。］

[Where:
* Represents the site | part couple | bonded with an iridium atom or a platinum atom.
R ^L5 and R ^{L6 each} represent a bond, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups may have a substituent. When a plurality of R ^L5 are present, they may be the same or different.
R ^L7 represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups optionally have a substituent. ]

In formulas (J-1) to (J-16), R ^L5 and R ^L6 are preferably an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group. It is more preferably a cyclic group or a substituted amino group, and further preferably an aryl group.

In formulas (J-1) to (J-16), R ^L7 is preferably an alkyl group, a cycloalkyl group, an aryl group, or a substituted amino group, and more preferably an alkyl group or an aryl group.

The ligand composed of ring B ¹ and ring B ² preferably has a bond. If the ligand constituted by the ring B ¹ and ring B ² has a bond, it is preferable that the ring B ² has a bond.

When the ligand composed of ring B ¹ and ring B ² has a bond, in formulas (J-1) to (J-16), R ^L5 is a bond, or R ^L6 is A bond is preferable, and R ^L5 is more preferably a bond.

In formula (1), formula (2) and formula (3), one of X ^a and X ^b is a single bond, and the other is a group represented by —CR ¹¹ R ¹² —CR ¹³ R ¹⁴ —. The group represented by Formula (1) is the group represented by Formula (1-1) or Formula (1-2), and the metal complex represented by Formula (2) is represented by Formula (2-1). ) Or a group represented by formula (2-2), and the metal complex represented by formula (3) is a group represented by formula (3-1) or formula (3-2).

［式中、Ｍ、ｎ₁、ｎ₂、ｎ₃、Ｘ¹、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷、Ｘ⁸、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ¹¹、Ｒ¹²、Ｒ¹³、Ｒ¹⁴、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＡ¹−Ｇ¹−Ａ²は、前記と同じ意味を表す。］

_{Wherein, M, n 1, n 2} , n 3, X 1, X 3, X 4, X 5, X 6, X 7, X 8, R 1, R 2, R 3, R 4, R 5 , R ⁶ , R ⁷ , R ⁸ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and A ¹ -G ¹ -A ² are Means the same. ]

  Among the groups represented by formula (1-1), formula (1-2), formula (2-1), formula (2-2), formula (3-1), and formula (3-2), Since the synthesis of the polymer compound of the invention is facilitated, a group represented by the formula (1-1), the formula (1-2), the formula (2-1) or the formula (3-2) is preferable. 1-1), a group represented by formula (1-2) or formula (2-1) is more preferred, a group represented by formula (1-1) or formula (1-2) is more preferred, The group represented by (1-1) is particularly preferable.

In formula (1-1), formula (1-2), formula (2-1), formula (2-2), formula (3-1), and formula (3-2), R ¹¹ , R ¹² , R ^At least one selected from the group consisting of ¹³ and R ¹⁴ is an alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. In order to facilitate the synthesis of the polymer compound of the invention, an alkyl group or an alkoxy group is more preferable, an alkyl group is further preferable, and these groups preferably have a substituent.

In formula (1-1), formula (1-2), formula (2-1), formula (2-2), formula (3-1) and formula (3-2), R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , R ¹¹ and R ¹³ , and R ¹² and R ¹⁴ may be bonded to each other to form a ring together with the atoms to which they are bonded. The formed ring structure may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent heterocyclic ring. Groups and halogen atoms.

In formula (1-1), formula (1-2), formula (2-1), formula (2-2), formula (3-1), and formula (3-2), the luminance of the light-emitting element of the present invention Since the lifetime is excellent, R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are preferably alkyl groups which may have a substituent, and R ¹¹ , R ¹² , R ¹³ and R ¹⁴ have a substituent. R ¹¹ and R ¹³ are bonded to form a ring with each bonded atom, and R ¹² and R ¹⁴ are bonded to form a ring with each bonded atom. It is preferable.

  The group represented by formula (1-1) is preferably a group represented by formula (1-3), and the group represented by formula (1-2) is represented by formula (1-4). The group represented by Formula (2-1) is preferably a group represented by Formula (2-3), and represented by Formula (2-2). The group is preferably a group represented by formula (2-4), and the group represented by formula (3-1) is preferably a group represented by formula (3-3). The group represented by formula (3-2) is preferably a group represented by formula (3-4).

［式中、Ｍ、ｎ₁、ｎ₂、ｎ₃、ｍ₁、ｍ₂、Ｘ¹、Ｘ²、Ｘ³、Ｘ⁴、Ｘ⁵、Ｘ⁶、Ｘ⁷、Ｘ⁸、Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ¹⁵、Ｒ¹⁶、Ｒ¹⁷、Ｒ¹⁸、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＡ¹−Ｇ¹−Ａ²は、前記と同じ意味を表す。］

_{Wherein, M, n 1, n 2} , n 3, m 1, m 2, X 1, X 2, X 3, X 4, X 5, X 6, X 7, X 8, R 1, R 2 , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and A ¹ -G ¹ -A ² represents the same meaning as described above. ]

  Among the groups represented by formula (1-3), formula (1-4), formula (2-3), formula (2-4), formula (3-3) and formula (3-4), In order to facilitate the synthesis of the polymer compound of the invention, a group represented by the formula (1-3), formula (1-4), formula (2-3) or formula (3-4) is preferred, 1-3), a group represented by formula (1-4) or formula (2-3) is more preferred, a group represented by formula (1-3) or formula (1-4) is more preferred, The group represented by (1-3) is particularly preferable.

In formula (1-3), formula (1-4), formula (2-3), formula (2-4), formula (3-3), and formula (3-4), the luminance of the light-emitting element of the present invention Since the lifetime is excellent, m ₁ and m ₂ are preferably integers of 3 to 5, more preferably 3 or 4, and still more preferably 3.

In Formula (1-3), Formula (1-4), Formula (2-3), Formula (2-4), Formula (3-3), and Formula (3-4), m ₁ and m ₂ are Although they may be the same or different, m ₁ and m ₂ are preferably the same as each other in order to facilitate the synthesis of the polymer compound of the present invention.

In formula (1-3), formula (1-4), formula (2-3), formula (2-4), formula (3-3), and formula (3-4), R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom, because the luminance lifetime of the light emitting device of the present invention is excellent. Further preferred.

In the groups represented by Formula (1-3), Formula (1-4), Formula (2-3), Formula (2-4), Formula (3-3), and Formula (3-4), for example, When at least one of R ¹⁵ and R ¹⁶ is a group other than a hydrogen atom and at least one of R ¹⁷ and R ¹⁸ is a hydrogen atom, when R ¹⁵ and R ¹⁶ are different from each other, R ¹⁷ and R ¹⁸ are When different, stereoisomers can occur. The groups represented by formula (1-3), formula (1-4), formula (2-3), formula (2-4), formula (3-3) and formula (3-4) are the same. It may be a group having only a stereoisomer or a group having a plurality of different stereoisomers. Stereoisomers include diastereomers and enantiomers.

  When the group represented by formula (1-3) has the ligand represented by formula (1-3-Z), the stereoisomer of the ligand represented by formula (1-3-Z) Is represented by, for example, formula (1-3-a), formula (1-3-b), formula (1-3-c), and formula (1-3-d).

［式中、＊は、イリジウム原子又は白金原子と結合する部位を表す。Ｒ^a及びＲ^bは、それぞれ独立に、アルキル基又はシクロアルキル基を表し、これらの基は置換基を有していてもよい。］

[In formula, * represents the site | part couple | bonded with an iridium atom or a platinum atom. R ^a and R ^b each independently represents an alkyl group or a cycloalkyl group, and these groups optionally have a substituent. ]

  The ligands represented by formula (1-3-a), formula (1-3-b), formula (1-3-c) and formula (1-3-d) are in a diastereomeric relationship with each other. It is in.

  A plurality of stereoisomers may exist in the groups represented by the formulas (1) to (3). Examples include a group having a ligand that is an enantiomer, a group having a ligand that is a diastereomer, and a group that becomes a diastereomer as a whole when a plurality of ligands are enantiomers.

Specific examples of the group represented by M ^1G include groups represented by the following formulas (Ir-101) to (Ir-105).

Specific examples of the group represented by M ^2G include groups represented by the following formulas (Ir-201) to (Ir-205) and (Pt-201) to (Pt-203).

Specific examples of the group represented by M ^3G include groups represented by the following formulas (Ir-301) to (Ir-305).

・ Bridged structural unit (XL)
The polymer compound of the present invention preferably has a structural unit having at least one crosslinking group selected from the crosslinking group A group (hereinafter referred to as a crosslinked structural unit (XL)).

  As the cross-linking group selected from the cross-linking group A group, since the cross-linking property of the polymer compound of the present invention is excellent, the formulas (XL-1), (XL-3), (XL-5), (XL-7), A crosslinking group represented by (XL-16) or (XL-17) is preferred, a crosslinking group represented by formula (XL-1) or formula (XL-17) is more preferred, and a formula (XL-17) Even more preferred are the crosslinking groups represented. The cross-linking structural unit (XL) is preferably a structural unit represented by the following formula (4) or a structural unit represented by the formula (5), and is a structural unit represented by the following formula (4). Is more preferable, but may be a structural unit represented by the following formula.

  [Structural Unit Represented by Formula (4)]

［式中、
ｎＡは０〜５の整数を表し、ｎは１又は２を表す。
Ａｒ¹は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^Aは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^Aが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘは、架橋基Ａ群から選ばれる架橋基を表す。Ｘが複数存在する場合、それらは同一でも異なっていてもよい。］

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

  nA is preferably 0 or 1, more preferably 0, since the luminance lifetime of the light emitting device of the present invention is more excellent.

  n is preferably 2 because the luminance lifetime of the light emitting device of the present invention is more excellent.

Ar ¹ is preferably an aromatic hydrocarbon group which may have a substituent since the luminance lifetime of the light emitting device of the present invention is more excellent.

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

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

The aromatic hydrocarbon group and heterocyclic group represented by Ar ¹ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, and an aryloxy group. Group, halogen atom, monovalent heterocyclic group and cyano group.

Alkylene group represented by L ^A is not including the carbon atom number of substituent is usually 1 to 10, preferably 1 to 5, more preferably 1 to 3. Cycloalkylene group represented by L ^A is not including the carbon atom number of substituent is usually 3 to 10.
The alkylene group and the cycloalkylene group may have a substituent, and examples thereof include a methylene group, an ethylene group, a propylene group, a butylene group, a hexylene group, a cyclohexylene group, and an octylene group.

Alkylene group and cycloalkylene group represented by L ^A may have a substituent. Examples of the substituent that the alkylene group and the cycloalkylene group may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, and a cyano group.

The arylene group represented by L ^A may have a substituent. Examples of the arylene group include o-phenylene, m-phenylene, and p-phenylene. Examples of the substituent that the aryl group may have include, for example, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a halogen atom, a cyano group, and a bridge. Examples thereof include a crosslinking group selected from the group A.

L ^A is preferably a phenylene group or an alkylene group because the production of the polymer compound of the present invention is facilitated, and these groups may have a substituent.

  As the cross-linking group represented by X, since the cross-linking property of the polymer compound of the present invention is excellent, preferably the formula (XL-1), (XL-3), (XL-5), (XL-7), A group represented by (XL-16) or (XL-17), more preferably a group represented by Formula (XL-1) or Formula (XL-17), and still more preferably a group represented by Formula (XL-). 17).

  [Structural Unit Represented by Formula (5)]

［式中、
ｍＡは０〜５の整数を表し、ｍは１〜４の整数を表し、ｃは０又は１の整数を表す。ｍＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ³は、芳香族炭化水素基、複素環基、又は、少なくとも１種の芳香族炭化水素環と少なくとも１種の複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ａｒ²及びＡｒ⁴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。
Ａｒ²、Ａｒ³及びＡｒ⁴はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と、直接又は酸素原子もしくは硫黄原子を介して結合して、環を形成していてもよい。
Ｋ^Aは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、−ＮＲ’−で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｋ^Aが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘ’は、架橋基Ａ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。但し、少なくとも１つのＸ’は、架橋基Ａ群から選ばれる架橋基である。］

[Where:
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents an integer of 0 or 1. When a plurality of mA are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded, and these groups have a substituent. It may be.
Ar ² and Ar ⁴ each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ² , Ar ³ and Ar ⁴ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or via an oxygen atom or a sulfur atom to form a ring. It may be.
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, the group represented by -NR'-, an oxygen atom or a sulfur atom, these groups have a substituent Also good. R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. When a plurality of K ^A are present, they may be the same or different.
X ′ represents a bridging group selected from the bridging group A group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. However, at least one X ′ is a crosslinking group selected from the crosslinking group A group. ]

  mA is preferably 0 or 1, more preferably 0, because the luminance lifetime of the light emitting device of the present invention is excellent.

  m is preferably 2 because the luminance lifetime of the light emitting device of the present invention is excellent.

  c is preferably 0 because the polymer compound of the present invention can be easily produced and the luminance life of the light emitting device of the present invention is excellent.

Ar ³ is preferably an aromatic hydrocarbon group which may have a substituent since the luminance lifetime of the light emitting device of the present invention is excellent.

The definition and example of the arylene group part excluding m substituents of the aromatic hydrocarbon group represented by Ar ³ are the same as the definition and example of the arylene group represented by Ar ^X2 in formula (X) described later. It is.

The definition and examples of the divalent heterocyclic group part excluding m substituents of the heterocyclic group represented by Ar ³ are the divalent heterocyclic group represented by Ar ^X2 in formula (X) described later. Same as definition and example of part.

Definitions and examples of divalent groups excluding m substituents of a group in which at least one aromatic hydrocarbon ring represented by Ar ³ and at least one heterocyclic ring are directly bonded are shown in the formula ( The definition and examples of the divalent group in which at least one arylene group represented by Ar ^X2 in X) and at least one divalent heterocyclic group are directly bonded are the same.

Ar ² and Ar ⁴ are preferably an arylene group which may have a substituent since the luminance lifetime of the light emitting device of the present invention is excellent.

The definitions and examples of the arylene groups represented by Ar ² and Ar ⁴ are the same as the definitions and examples of the arylene groups represented by Ar ^X1 and Ar ^X3 in formula (X) described later.

The definitions and examples of the divalent heterocyclic group represented by Ar ² and Ar ⁴ are the same as the definitions and examples of the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 in formula (X) described later. is there.

The groups represented by Ar ² , Ar ³ and Ar ⁴ may have a substituent, and examples of the substituent include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, Examples thereof include a halogen atom, a monovalent heterocyclic group, and a cyano group.

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

K ^A, since production of the polymer compound of the present invention is facilitated, it is preferable that a phenylene group or a methylene group.

  As the cross-linking group represented by X ′, since the cross-linking property of the polymer compound of the present invention is excellent, preferably the formula (XL-1), (XL-3), (XL-5), (XL-7) , (XL-16) or (XL-17), more preferably a group represented by Formula (XL-1) or Formula (XL-17), and still more preferably a group represented by Formula (XL). -17).

[Preferred Aspect of Structural Unit Represented by Formula (4) or (5)]
As a structural unit represented by Formula (4), the structural unit represented by Formula (4-1)-Formula (4-30) is mentioned, for example, As a structural unit represented by Formula (5), For example, the structural unit represented by Formula (5-1)-Formula (5-9) is mentioned. Among these, since the crosslinkability of the polymer compound of the present invention is excellent, preferably the formula (4-1) to the formula (4-30), the formula (5-3), the formula (5-7), or the formula (5) -9), more preferably the formula (4-1) to the formula (4-15), the formula (4-19), the formula (4-20), the formula (4-23), A structural unit represented by formula (4-25), formula (4-30), formula (5-3), or formula (5-9), and more preferably formula (4-1) to formula (4- 9) is a structural unit represented by formula (4-30) or formula (5-3).

The content of the cross-linking structural unit (XL) is 0.5 to 70 mol% with respect to the total amount of the structural units contained in the polymer compound because the polymer compound of the present invention has excellent stability and crosslinkability. Preferably, it is 3 to 50 mol%, more preferably 3 to 30 mol%.
In the polymer compound of the present invention, the crosslinking structural unit (XL) may be contained singly or in combination of two or more.

<Structural Unit Represented by Formula (Y)>
The polymer compound of the present invention preferably further contains a structural unit represented by the formula (Y).

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

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

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, and further preferable. The ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar ^Y1 described above.

  Examples of the “divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded” include groups represented by the following formulas, which have a substituent. You may do 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。］

[Wherein R ^XX represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]

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

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

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formulas (Y-1) to (Y-10). From the viewpoint of the luminance life of the light emitting device of the present invention, Preferably, it is a structural unit represented by the formula (Y-1), (Y-2) or (Y-3). From the viewpoint of electron transport properties, the formulas (Y-4) to (Y-7) are preferred. ), And from the viewpoint of hole transportability, it is preferably a structural unit represented by 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。］

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

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

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

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

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

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

［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。］

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

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

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

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

In X ^Y1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded. When R ^Y2 forms a ring, —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — The group represented is preferably a group represented by formulas (Y-B1) to (Y-B5), more preferably a group represented by 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。］

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

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

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

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

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

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

  The structural unit represented by the formula (Y-3) is preferably a 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。］

[Wherein, R ^Y11 and X ^Y1 represent the same meaning as described above. ]

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

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

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

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

［式中、Ｒ^Y1及びＲ^Y3は前記と同じ意味を表す。］

[Wherein, R ^Y1 and R ^Y3 represent the same meaning 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。］

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

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

  Examples of the structural unit represented by the formula (Y) include structural units composed of an arylene group represented by the formulas (Y-101) to (Y-121), and the formulas (Y-201) to (Y-206). A structural unit consisting of a divalent heterocyclic group represented by the formula: at least one arylene group represented by formulas (Y-301) to (Y-304) and at least one divalent heterocyclic group. Examples thereof include a structural unit composed of a divalent group directly bonded.

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, has a higher luminance life of the light-emitting element of the present invention, so that the total amount of the structural units contained in the polymer compound is On the other hand, it is preferably 0.5 to 95 mol%, more preferably 20 to 90 mol%, still more preferably 40 to 80 mol%.

A structural unit represented by the formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group directly bonded to each other. The structural unit that is a group is preferably 0.1 to 50 mol%, more preferably based on the total amount of the structural units contained in the polymer compound, because the charge transport property of the light emitting device of the present invention is excellent. Is 1 to 40 mol%, more preferably 5 to 30 mol%, and particularly preferably 7 to 15 mol%.

  As for the structural unit represented by the formula (Y), only one kind may be contained in the polymer compound of the present invention, or two or more kinds may be contained.

<Structural Unit Represented by Formula (X)>
The polymer compound of the present invention may further contain a structural unit represented by the following 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。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。］

[ ^Wherein , a ^X1 and a ^X2 each independently represent an integer of 0 or more. Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. And these groups may have a substituent. R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. ]

a ^X1 is preferably 2 or less, more preferably 1, because the luminance life of the light emitting device of the present invention is excellent.

a ^X2 is preferably 2 or less, more preferably 0, because the luminance life of the light emitting device of the present invention is excellent.

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

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

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

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

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

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

More preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one kind of arylene group represented by Ar ^X2 and Ar ^X4 and at least one kind of divalent heterocyclic group are directly bonded. Further preferable ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 , respectively.

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 in the formula (Y). Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.

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

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

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

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

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

  The polymer compound of the present invention may further contain a structural unit represented by the formula (X). However, since the driving voltage of the light emitting device of the present invention is more excellent, the structural unit represented by the formula (X) It is preferable that it is further included.

  When the polymer compound of the present invention further contains a structural unit represented by the formula (X), it is preferably 0.01 to 50 mol relative to the total amount of the structural units contained in the polymer compound of the present invention. %, More preferably 0.1 to 20 mol%, and still more preferably 0.1 to 5 mol%.

  The structural unit represented by the formula (X) may be included in the polymer compound of the present invention alone or in combination of two or more.

  Examples of the polymer compound of the present invention include polymer compounds PA to PI in Table 1. Here, the “other” structural unit is a structural unit represented by the formula (3G), a structural unit represented by the formula (1G), a structural unit represented by the formula (2G), or a formula (4G). Meaning a structural unit other than the structural unit represented by the structural unit represented, the structural unit represented by the crosslinked structural unit (XL), the structural unit represented by the formula (Y), and the formula (X).

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

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

  The polymer compound of the present invention may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other embodiments, but a plurality of types of raw materials A copolymer obtained by copolymerizing monomers is preferred.

<Method for producing polymer compound>
Next, a method for producing the polymer compound of the present invention will be described.

The polymer compound of the present invention may be produced by any method. For example, the compound represented by the formula (M-1G), the compound represented by the formula (M-2G), and the formula (M-3G) And at least one compound selected from the group consisting of the compound represented by formula (M-4G) can be produced by condensation polymerization.
The polymer compound according to a preferred embodiment of the present invention is, for example,
A compound represented by the formula (M-Y1);
At least one compound selected from the group consisting of a compound represented by the formula (MY2) and a compound represented by the formula (MX);
A group consisting of a compound represented by formula (M-1G), a compound represented by formula (M-2G), a compound represented by formula (M-3G) and a compound represented by formula (M-4G) At least one compound selected from:
It can be produced by subjecting at least one compound selected from the group consisting of a compound represented by the formula (M-1) and a compound represented by the formula (M-2) to condensation polymerization.

  In the present specification, the compounds used for the production of the polymer compound of the present invention are sometimes collectively referred to as “raw material monomers”.

［式中、
Ａｒ^Y1、Ａｒ^X1〜Ａｒ^X4、Ｒ^X1〜Ｒ^X3、ａ^X1、ａ^X2、Ｌ¹〜Ｌ³、Ｍ^1G〜Ｍ^3G、Ａｒ^1M、ｎ^a1、ｎ^b1、ｎ^c1、Ａｒ¹、Ｌ^A、Ｘ、ｎＡ、ｎ、Ａｒ²〜Ａｒ⁴、Ｋ^A、Ｘ’、ｍＡ、ｍ及びｃは、前記と同じ意味を表す。
Ｚ^C1〜Ｚ^C18は、それぞれ独立に、置換基Ａ群及び置換基Ｂ群からなる群から選ばれる基を示す。］

[Where:
^{Ar Y1, Ar X1 ~Ar X4,} R X1 ~R X3, a X1, a X2, L 1 ~L 3, M 1G ~M 3G, Ar 1M, n a1, n b1, n c1, Ar 1, L A , X, nA, n, Ar ^{2 to} Ar ⁴ , K ^A , X ′, mA, m and c have the same meaning as described above.
Z ^{C1 to} Z ^C18 each independently represent a group selected from the group consisting of the substituent group A and the substituent group B. ]

For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group A, Z ^{C3 to} Z ^C18 select groups selected from the substituent group B.
For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group B, Z ^{C3 to} Z ^C18 select groups selected from the substituent group A.
For example, when Z ^C1 , Z ^C2 and Z ^{C7 to} Z ^C14 are groups selected from the substituent group A, Z ^{C3 to} Z ^C6 and Z ^{C15 to} Z ^C18 select groups selected from the substituent group B.

· Substituent Group A chlorine atom, a bromine atom, an iodine atom, -O-S (= O) groups represented by ₂ R ^C1.
(In the formula, R ^C1 represents an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.)
-Substituent group B -B (OR ^C2 ) ₂ (wherein R ^C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups optionally have a substituent. R ^C2 present may be the same or different and may be linked to each other to form a ring structure together with the oxygen atom to which they are bonded.
A group represented by —BF ₃ Q ′ (wherein Q ′ represents Li, Na, K, Rb or Cs);
A group represented by —MgY ′ (wherein 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 The groups 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 following formulas (W-1) to (W-10).

  A compound having a group selected from Substituent Group A and a compound having a group selected from Substituent Group B are subjected to condensation polymerization by a known coupling reaction, and a group selected from Substituent Group A and Substituent Group B Carbon atoms bonded to a group selected from are bonded to each other. Therefore, if a compound having one or more groups selected from Substituent Group A and a compound having one or more groups selected from Substituent Group B are subjected to a known coupling reaction, these compounds are obtained by condensation polymerization. The condensation polymer can be obtained.

  The condensation polymerization is usually performed in the presence of a catalyst, a base and a solvent, and may be performed in the presence of a phase transfer catalyst, if necessary.

  Examples of the catalyst include dichlorobis (triphenylphosphine) palladium, dichlorobis (tris-o-methoxyphenylphosphine) palladium, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium acetate, and the like. Transition of nickel complexes such as palladium complexes of nickel, nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel Metal complexes; these transition metal complexes may be triphenylphosphine, tri-o-tolylphosphine, tri (tert-butylphosphine), tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl, etc. Complex having a ligand, and the like. A catalyst may be used individually by 1 type, or may use 2 or more types together.

  The usage-amount of a catalyst is 0.000001-3 molar equivalent normally as a quantity of the transition metal with respect to the sum total number of moles of a raw material monomer.

  Examples of the base include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organic bases such as tetrabutylammonium fluoride and tetrabutylammonium hydroxide. . A base may be used individually by 1 type, or may use 2 or more types together.

  Examples of the phase transfer catalyst include tetrabutylammonium chloride and tetrabutylammonium bromide. A phase transfer catalyst may be used individually by 1 type, or may use 2 or more types together.

  The usage-amount of a base is 0.001-100 molar equivalent normally with respect to the total number of moles of a raw material monomer.

  The amount of the phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of raw material monomers.

  Examples of the solvent include organic solvents such as toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide, and water. A solvent may be used individually by 1 type, or may use 2 or more types together.

  The usage-amount of a solvent is 10-100,000 weight part normally with respect to a total of 100 weight part of a raw material monomer.

  The reaction temperature of the condensation polymerization is usually −100 to 200 ° C. The reaction time of the condensation polymerization is usually 1 hour or more.

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

· The compound M-1G~M-4G manufacturing process process for the preparation of a compound M-3G, for example, metal complexes obtained by substituting two bonds having a group represented by M ^2G with a substituent X ¹⁰⁰ (hereinafter, And a compound represented by the following formula (Y-X301) and a compound represented by the following formula (Y-X302). The substituent X ¹⁰⁰ is a group selected from the substituent group A and the substituent group B.

［式中、
ｎ^b1、Ｌ²、Ｚ^C7及びＺ^C8は、前記と同じ意味を表す。
Ｘ¹⁰¹は、置換基Ａ群及び置換基Ｂ群から選ばれる基であり、Ｘ¹⁰⁰とは互いに異なる基である。］

[Where:
n ^b1 , L ² , Z ^C7 and Z ^C8 represent the same meaning as described above.
X ¹⁰¹ is a group selected from the substituent group A and the substituent group B, and is a group different from X ¹⁰⁰ . ]

As a method for producing compound M-1G, for example, a metal complex in which one bond of a group represented by M ^1G is substituted with substituent X ¹⁰⁰ (hereinafter referred to as “MC-1G”), and the following: A method of condensation polymerization with a compound represented by the formula (Y-X101) can be given. The substituent X ¹⁰⁰ has the same meaning as described above.

［式中、ｎ^a1、Ｌ¹、Ｘ¹⁰¹及びＺ^C9は、前記と同じ意味を表す。］

[Wherein, n ^a1 , L ¹ , X ¹⁰¹ and Z ^C9 represent the same meaning as described above. ]

As a manufacturing method of compound M-2G, the method of condensation-polymerizing metal complex MC-1G and the compound represented by a following formula (Y-X201) is mentioned, for example. The substituent X ¹⁰⁰ has the same meaning as described above.

［式中、ｎ^b1、ｎ^c1、Ａｒ^1M、Ｌ²、Ｌ³、Ｘ¹⁰¹、Ｚ^C10及びＺ^C11は、前記と同じ意味を表す。］

[Wherein, n ^b1 , n ^c1 , Ar ^1M , L ² , L ³ , X ¹⁰¹ , Z ^C10 and Z ^C11 represent the same meaning as described above. ]

As a method for producing the compound M-4G, for example, a metal complex in which three bonds of the group represented by M ^3G are substituted with a substituent X ¹⁰⁰ (hereinafter referred to as “MC-3G”), and the following: Examples thereof include a method of subjecting a compound represented by the formula (Y-X401), a compound represented by the following formula (Y-X402), and a compound represented by the following formula (Y-X403) to condensation polymerization. The substituent X ¹⁰⁰ has the same meaning as described above.

［式中、ｎ^b1、Ｌ²、Ｘ¹⁰¹、Ｚ^C12、Ｚ^C13及びＺ^C14は、前記と同じ意味を表す。］

[Wherein, n ^b1 , L ² , X ¹⁰¹ , Z ^C12 , Z ^C13 and Z ^C14 represent the same meaning as described above. ]

And manufacturing method the metal complex MC-2G of the metal complex MC-2G may be produced by any method, but here, the two bonds having a group represented by the formula (1) with a substituent X ¹⁰⁰ Among the substituted metal complexes, a method for producing a metal complex MC-2G in which M is an iridium atom, n1 is 1, and n3 is 2 will be described.

The metal complex MC-2G can be produced by a method of reacting a compound serving as a ligand with a metal compound. For example, after producing a metal complex represented by the following formula (J4), the substituent X ¹⁰⁰ may be introduced.

  The metal complex represented by the formula (J4) is obtained by reacting, for example, a compound represented by the formula (J1) with an iridium compound or a hydrate thereof to convert the metal complex represented by the formula (J2). It can be produced by a method including the step A1 to be synthesized and the step B1 in which the metal complex represented by the formula (J2) and the compound represented by the formula (J3) are reacted.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹及びＥ²は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ and E ² have the same meaning as described above. Represents. ]

  In Step A1, examples of the iridium compound include iridium chloride, iridium bromide, tris (acetylacetonato) iridium (III), chloro (cyclooctadiene) iridium (I) dimer, and iridium acetate (III). Examples of the hydrate of the iridium compound include iridium chloride trihydrate.

  Process A1 and process B1 are normally performed in a solvent. Examples of the solvent include methanol, ethanol, propanol, ethylene glycol, propylene glycol, glycerin, 2-methoxyethanol, 2-ethoxyethanol, 2- (2-ethoxyethoxy) ethanol, 2- (i-propoxy) ethanol, 2 Alcohol solvents such as-(n-butoxy) ethanol and 2- (t-butoxy) ethanol; ether solvents such as diethyl ether, tetrahydrofuran, dioxane, cyclopentylmethyl ether and diglyme; halogen solvents such as methylene chloride and chloroform; Nitrile solvents such as acetonitrile and benzonitrile; hydrocarbon solvents such as hexane, decalin, toluene, xylene and mesitylene; amide systems such as N, N-dimethylformamide and N, N-dimethylacetamide Medium; acetone, organic solvents such as dimethyl sulfoxide and water. These may be used as a mixture.

  In step A1 and step B1, the reaction time is usually 30 minutes to 150 hours, and the reaction temperature is usually between the melting point and boiling point of the solvent present in the reaction system.

  In step A1, the amount of the compound represented by the formula (J1) is usually 2 to 20 mol with respect to 1 mol of the iridium compound or its hydrate, and from the viewpoint of yield and purity of the product. 2 to 10 moles are preferred.

  In Step B1, the amount of the compound represented by the formula (J3) is usually 1 to 100 mol with respect to 1 mol of the metal complex represented by the formula (J2), and the yield and purity of the product From this viewpoint, 1 to 30 mol is preferable.

  In step B1, the reaction is preferably performed in the presence of a silver compound such as silver trifluoromethanesulfonate. When using a silver compound, the quantity is 2-20 mol normally with respect to 1 mol of metal complexes represented by a formula (J2).

As a method of introducing a substituent X ¹⁰⁰ to a metal complex represented by formula (J4) is, for example, the production method of the metal complex represented by the following formula (J5). The metal complex represented by the formula (J5) is a suitable example of the metal complex MC-2G.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹及びＥ²は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ and E ² have the same meaning as described above. Represents. ]

More specifically, among the metal complexes represented by the formula (J5), the metal complex represented by the formula (J6) in which X ¹⁰⁰ is a chlorine atom, a bromine atom, or an iodine atom is represented by, for example, the formula ( It can be synthesized by the step C1 in which the metal complex represented by J4) is reacted with the halogenating agent. The metal complex represented by the formula (J6) is a suitable example of the metal complex MC-2G.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹及びＥ²は、前記と同じ意味を表す。
Ｘ¹⁰²は、塩素原子、臭素原子又はヨウ素原子を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ and E ² have the same meaning as described above. Represents.
^X102 represents a chlorine atom, a bromine atom or an iodine atom. ]

  Step C1 is usually performed in a solvent. A solvent, reaction time, and reaction temperature are the same as what was demonstrated about the said process A1 and process B1.

  In step C1, as halogenating agents, chlorinating agents such as N-chlorosuccinimide, chlorine molecules, and benzyltrimethylammonium tetrachloroiodate, N-bromosuccinimide, dibromoisocyanuric acid, bromine molecules, and benzyltrimethylammonium tribromide Brominating agents such as N-iodosuccinimide, iodine molecules, and Barluenga reagent, and the like, and a catalyst may be allowed to coexist if necessary. The halogenating agent is preferably a brominating agent and an iodinating agent from the viewpoints of yield and product reactivity.

  In Step C1, the amount of the halogenating agent is usually 0.1 to 50 mol with respect to 1 mol of the compound represented by the formula (J4).

Among the metal complexes represented by the formula (J5), the metal complex represented by the formula (J7) in which X ¹⁰⁰ is —B (OR ^W1 ) ₂ is represented by the formula (J6) in Step D1 in a solvent, for example. ). The metal complex represented by the formula (J7) is a suitable example of the metal complex MC-2G.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰²は、前記と同じ意味を表す。

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰² are Means the same.

R ^W1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an amino group, and these groups may have a substituent. A plurality of R ^W1 may be the same or different, and may be bonded to each other to form a ring structure together with the atoms to which they are bonded. ]

  Examples of the step D1 include Ishiyama-Miyaura-Hartwig borylation reaction.

  When ring A has a substituent, the compound represented by the formula (J3) is obtained by, for example, combining a compound represented by the formula (J8) and a compound represented by the formula (J9) with a Suzuki reaction or a Kumada reaction. , Can be synthesized by a coupling reaction such as a Stille reaction.

［式中、
Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a及びＸ^bは、前記と同じ意味を表す。
環Ａ¹⁰¹は、Ｗ¹¹で表される基を有する芳香族複素環を表し、該環はＷ¹¹で表される基以外の置換基を有していてもよい。Ｗ¹¹は、−Ｂ（ＯＲ^W1）₂で表される基、アルキルスルホニルオキシ基、シクロアルキルスルホニルオキシ基、アリールスルホニルオキシ基、塩素原子、臭素原子又はヨウ素原子を表し、これらの基は置換基を有していてもよい。Ｒ^W1は前記と同じ意味を表す。
Ｚ¹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、置換アミノ基、ハロゲン原子、式（Ｄ−Ａ）又は式（Ｄ−Ｂ）で表される基を表す。
Ｗ¹は、−Ｂ（ＯＲ^W1）₂で表される基、アルキルスルホニルオキシ基、シクロアルキルスルホニルオキシ基、アリールスルホニルオキシ基、塩素原子、臭素原子又はヨウ素原子を表し、これらの基は置換基を有していてもよい。］

[Where:
X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a and X ^b represent the same meaning as described above.
Ring A ¹⁰¹ represents an aromatic heterocyclic ring having a group represented by W ¹¹ , and the ring may have a substituent other than the group represented by W ¹¹ . W ¹¹ represents a group represented by —B (OR ^W1 ) ₂ , an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom, and these groups are substituents. You may have. R ^W1 represents the same meaning as described above.
Z ¹ represents an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, a group represented by the formula (DA) or the formula (D-B).
W ¹ represents a group represented by —B (OR ^W1 ) ₂ , an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom, and these groups are substituents. You may have. ]

Examples of the group represented by —B (OR ^W1 ) ₂ are the same as the examples of the group represented by —B (OR ^C2 ) ₂ in the substituent group B.

Examples of the alkylsulfonyloxy group represented by W ¹ include a methanesulfonyloxy group, an ethanesulfonyloxy group, and a trifluoromethanesulfonyloxy group.

Examples of the arylsulfonyloxy group represented by W ¹ include a p-toluenesulfonyloxy group.

W ¹ is a group represented by —B (OR ^W1 ) ₂ , trifluoromethane, because the coupling reaction of the compound represented by formula (J8) and the compound represented by formula (J9) proceeds easily. A sulfonyloxy group, a chlorine atom, a bromine atom, or an iodine atom is preferable. Among these, since the synthesis of the compound represented by the formula (J9) is easy, the chlorine atom, the bromine atom, or the formula (W-7) is used. More preferred are the groups

The alkylsulfonyloxy group, cycloalkylsulfonyloxy group and arylsulfonyloxy group represented by W ¹¹ have the same meanings as the alkylsulfonyloxy group, cycloalkylsulfonyloxy group and arylsulfonyloxy group represented by W ¹ , respectively. Represent.

W ¹¹ is preferably a bromine atom, an iodine atom or a group represented by the formula (W-7).

Z ¹ is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, a group represented by the formula (D-A1) or the formula (D-B1), an alkyl group, a cycloalkyl group, An aryl group or a group represented by the formula (D-A1) is more preferable, an alkyl group or an aryl group is further preferable, and an aryl group is particularly preferable.

  The coupling reaction between the compound represented by the formula (J8) and the compound represented by the formula (J9) is usually performed in a solvent. The solvent used, the reaction time, and the reaction temperature are the same as those described for Step A1 and Step B1.

  In the coupling reaction between the compound represented by the formula (J8) and the compound represented by the formula (J9), the amount of the compound represented by the formula (J9) is 1 mol of the compound represented by the formula (J8). The amount is usually 0.05 to 20 mol.

Examples of the compound represented by the formula (J9) include a group in which Z ¹ is an aryl group and W ¹ is represented by —B (OR ^W1 ) ₂ , a trifluoromethanesulfonyloxy group, a bromine atom, or iodine. The compound which is an atom is mentioned.

  The compound represented by the formula (J8) can be produced, for example, by subjecting a compound represented by the formula (J10) and a compound represented by the formula (J11) to a coupling reaction. This coupling reaction is the same as that described for the compound represented by formula (J3).

［式中、
Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ¹⁰¹及びＷ¹¹は、前記と同じ意味を表す。
Ｗ³及びＷ⁴は、それぞれ独立に、−Ｂ（ＯＲ^W1）₂で表される基、アルキルスルホニルオキシ基、シクロアルキルスルホニルオキシ基、アリールスルホニルオキシ基、塩素原子、臭素原子又はヨウ素原子を表し、これらの基は置換基を有していてもよい。Ｒ^W1は前記と同じ意味を表す。］

[Where:
X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A ¹⁰¹ and W ¹¹ represent the same meaning as described above.
W ³ and W ⁴ each independently represent a group represented by —B (OR ^W1 ) ₂ , an alkylsulfonyloxy group, a cycloalkylsulfonyloxy group, an arylsulfonyloxy group, a chlorine atom, a bromine atom or an iodine atom. These groups may have a substituent. R ^W1 represents the same meaning as described above. ]

  The compound represented by the formula (J1) can be produced, for example, by subjecting a compound represented by the formula (J12) and a compound represented by the formula (J13) to a coupling reaction. This coupling reaction is the same as that described for the compound represented by formula (J3).

［式中、Ｗ³、Ｗ⁴、Ｅ¹、Ｅ²、環Ｂ¹及び環Ｂ²は、前記と同じ意味を表す。］

[Wherein, W ³ , W ⁴ , E ¹ , E ² , ring B ¹ and ring B ² represent the same meaning as described above. ]

Metal complex MC-2G, the formula (J3) or by introducing a pre-substituent X ¹⁰⁰ in the formula (J1), can also be prepared in the same manner as the metal complex represented by the formula (J4). For example, the metal complex represented by the formula (J5) can be produced from the compound represented by the formula (J14).

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰⁰ are Means the same. ]

  Step A2 for obtaining a metal complex represented by formula (J15) from an iridium compound and a compound represented by formula (J14), and a metal complex represented by formula (J15) and a compound represented by formula (J3) Step B2 for obtaining a metal complex represented by the formula (J5) from the above can be carried out in the same manner as in Step A1 and Step B1.

  The compound represented by formula (J14) is produced from the compound represented by formula (J16) and the compound represented by formula (J13) in the same manner as the compound represented by formula (J1). be able to.

［式中、Ｗ³、Ｗ⁴、Ｅ¹、Ｅ²、環Ｂ¹、環Ｂ²及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, W ³ , W ⁴ , E ¹ , E ² , ring B ¹ , ring B ² and X ¹⁰⁰ represent the same meaning as described above. ]

  A metal complex represented by the following formula (J19), which is one of suitable examples of the metal complex MC-2G, can be produced from the formula (J17).

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰⁰は、前記と同じ意味を表す。ただし、Ｘ⁵〜Ｘ⁸のうちＸ¹⁰⁰が結合するＸ⁵〜Ｘ⁸は炭素原子であり、Ｘ¹⁰⁰が結合したＸ⁵〜Ｘ⁸には対応するＲ⁵〜Ｒ⁸は存在しない。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰⁰ are Means the same. However, X ⁵ to X ⁸ which X ¹⁰⁰ is attached out of X ⁵ to X ⁸ is a carbon atom, R ⁵ to R ⁸ corresponding to X ⁵ to X ⁸ which X ¹⁰⁰ is attached is absent. ]

  Step A4 for obtaining a metal complex represented by formula (J18) from an iridium compound and a compound represented by formula (J17), and a compound represented by formula (J18) and a compound represented by formula (J1) Step B4 for obtaining a metal complex represented by the formula (J19) can be carried out in the same manner as in Step A1 and Step B1.

  The compound represented by the formula (J17) is produced from the compound represented by the formula (J20) and the compound represented by the formula (J21) by the same method as the metal complex represented by the formula (J5). can do.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、Ｗ³、Ｗ⁴、及びＸ¹⁰⁰は、前記と同じ意味を表す。ただし、Ｘ⁵〜Ｘ⁸のうちＸ¹⁰⁰が結合するＸ⁵〜Ｘ⁸は炭素原子であり、Ｘ¹⁰⁰が結合したＸ⁵〜Ｘ⁸には対応するＲ⁵〜Ｒ⁸は存在しない。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , ring A, W ³ , W ⁴ , and X ¹⁰⁰ represent the same meaning as described above. However, X ⁵ to X ⁸ which X ¹⁰⁰ is attached out of X ⁵ to X ⁸ is a carbon atom, R ⁵ to R ⁸ corresponding to X ⁵ to X ⁸ which X ¹⁰⁰ is attached is absent. ]

And manufacturing method the metal complex MC-1G of the metal complex MC-1G may be prepared by any method, but here, one bond having a group represented by the formula (1) with a substituent X ¹⁰⁰ Among the substituted metal complexes, a method for producing a metal complex MC-1G in which M is an iridium atom, n1 is 2, and n3 is 1 will be described.

  As represented by the following formula, the ligand exchange reaction may proceed in the process of producing the metal complex represented by the formula (J5), and the metal complex represented by the formula (J22) is produced. be able to.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰⁰ are Means the same. ]

  Moreover, the metal complex represented by the formula (J22) can also be produced from the compound represented by the formula (J3).

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰⁰ are Means the same. ]

  When producing the metal complex represented by the formula (J22), the metal complex represented by the formula (J5) generated by the exchange reaction of the ligand can also be produced.

- metal complex MC-2G 'of the production method (2) of the substituted metal complex two bonds with a substituent X ¹⁰⁰ having a group represented by, M is an iridium atom, n1 is 1, n3 The metal complex MC-2G ′ in which is 2 will be described.

  For example, the metal complex represented by the following formula (J5-2), which is one of suitable examples of the metal complex MC-2G ′, is used in the production of the metal complex represented by the formula (J5). Instead of the compound represented by (J3), the compound represented by the following formula (J3-2) can be used to produce the compound by the same method as that for the metal complex represented by the above formula (J5). it can.

［式中、Ｘ³〜Ｘ⁸、Ｒ³〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ^{3 to} X ⁸ , R ^{3 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰⁰ represent the same meaning as described above. ]

［式中、Ｘ³〜Ｘ⁸、Ｒ³〜Ｒ⁸、Ｘ^a、Ｘ^b及び環Ａは、前記と同じ意味を表す。］

[Wherein, X ^{3 to} X ⁸ , R ^{3 to} R ⁸ , X ^a , X ^b and ring A represent the same meaning as described above. ]

  When ring A has a substituent, the compound represented by the formula (J3-2) uses the compound represented by the following formula (J10-2) instead of the compound represented by the formula (J10). Except this, it can be produced by the same method as that for the compound represented by formula (J3).

［式中、Ｘ³〜Ｘ⁸、Ｒ³〜Ｒ⁸、Ｘ^a、Ｘ^b及びＷ³は、前記と同じ意味を表す。］

[Wherein, X ^{3 to} X ⁸ , R ^{3 to} R ⁸ , X ^a , X ^b and W ³ represent the same meaning as described above. ]

- metal complex MC-2G '' of the production method (3) of the substituted metal complex two bonds with a substituent X ¹⁰⁰ having a group represented by, M is an iridium atom, n1 is 1, The metal complex MC-2G ″ in which n3 is 2 will be described.

  For example, a metal complex represented by the following formula (J5-3), which is one of preferred examples of the metal complex represented by the formula (MC-2G ″), is represented by the formula (J5). The metal complex represented by the formula (J5) except that the compound represented by the following formula (J3-3) is used instead of the compound represented by the formula (J3) used for the production of the metal complex. It can be manufactured by the same method.

［式中、Ｘ¹、Ｘ²、Ｘ⁵〜Ｘ⁸、Ｒ¹、Ｒ²、Ｒ⁵〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、環Ｂ¹、環Ｂ²、Ｅ¹、Ｅ²及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ² , X ^{5 to} X ⁸ , R ¹ , R ² , R ^{5 to} R ⁸ , X ^a , X ^b , Ring A, Ring B ¹ , Ring B ² , E ¹ , E ² and X ¹⁰⁰ is the same as defined above. ]

［式中、Ｘ¹、Ｘ²、Ｘ⁵〜Ｘ⁸、Ｒ¹、Ｒ²、Ｒ⁵〜Ｒ⁸、Ｘ^a、Ｘ^b及び環Ａは、前記と同じ意味を表す。］

[Wherein, X ¹ , X ² , X ^{5 to} X ⁸ , R ¹ , R ² , R ^{5 to} R ⁸ , X ^a , X ^b and ring A represent the same meaning as described above. ]

  When ring A has a substituent, the compound represented by the formula (J3-3) uses the compound represented by the following formula (J10-3) instead of the compound represented by the formula (J10). Except this, it can be produced by the same method as that for the compound represented by formula (J3).

［式中、Ｘ¹、Ｘ²、Ｘ⁵〜Ｘ⁸、Ｒ¹、Ｒ²、Ｒ⁵〜Ｒ⁸、Ｘ^a、Ｘ^b及びＷ³は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ² , X ^{5 to} X ⁸ , R ¹ , R ² , R ^{5 to} R ⁸ , X ^a , X ^b and W ³ represent the same meaning as described above. ]

And manufacturing method the metal complex MC-3G of the metal complex MC-3G may be produced by any method, but here, the three bonds having a group represented by the formula (1) with a substituent X ¹⁰⁰ Among the substituted metal complexes, a method for producing a metal complex MC-3G in which M is an iridium atom and n1 is 3 will be described.

For example, a metal complex represented by the following formula (J25) having a substituent X ¹⁰⁰ on ring A can be produced from a compound represented by the formula (J23). The metal complex represented by the formula (J25) is one suitable example of the metal complex MC-3G.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , ring A and X ¹⁰⁰ represent the same meaning as described above. ]

  Step A5 for obtaining a metal complex represented by formula (J24) from an iridium compound and a compound represented by formula (J23), and a metal complex represented by formula (J24) and a compound represented by formula (J23) Step B5 for obtaining a metal complex represented by the formula (J25) can be carried out in the same manner as in Step A1 and Step B1.

  The compound represented by the formula (J23) is produced from the compound represented by the formula (J10) and the compound represented by the formula (J26) by the same method as the compound represented by the formula (J8). Can do.

［式中、Ｘ¹、Ｘ⁴〜Ｘ⁸、Ｒ¹、Ｒ⁴〜Ｒ⁸、Ｘ^a、Ｘ^b、環Ａ、Ｗ³、Ｗ⁴、及びＸ¹⁰⁰は、前記と同じ意味を表す。］

[Wherein, X ¹ , X ^{4 to} X ⁸ , R ¹ , R ^{4 to} R ⁸ , X ^a , X ^b , ring A, W ³ , W ⁴ , and X ¹⁰⁰ represent the same meaning as described above. ]

<Composition>
The composition of the present invention is selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (different from the polymer compound of the present invention), an antioxidant and a solvent. At least one kind of material and the polymer compound of the present invention.

  In the composition of the present invention, the polymer compound of the present invention may be contained singly or in combination of two or more.

  The composition containing the polymer compound and the solvent of the present invention (hereinafter sometimes referred to as “ink”) is suitable for production of a light-emitting element using a printing method such as an inkjet printing method or a nozzle printing method.

  The viscosity of the ink may be adjusted according to the type of printing method, but when applying a printing method such as an inkjet printing method to a printing method that passes through a discharge device, in order to prevent clogging and flight bending at the time of discharge. The pressure is preferably 1 to 20 mPa · s at 25 ° C.

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

  In the ink, the blending amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

[Hole transport material]
The hole transport material is classified into a low molecular compound and a high molecular compound, and a high molecular compound is preferable, and a high molecular compound having a crosslinking group is more preferable.

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

  In the composition of the present invention, the compounding amount of the hole transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

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

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

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

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

  In the composition of the present invention, the compounding amount of the electron transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

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

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

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

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

  In the composition of the present invention, the compounding amounts of the hole injection material and the electron injection material are each usually 1 to 400 parts by weight, preferably 5 to 150 parts, per 100 parts by weight of the polymer compound of the present invention. Parts by weight.

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

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

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

  Only one kind or two or more kinds of ions may be doped.

[Light emitting material]
Luminescent materials (different from the polymer compound of the present invention) are classified into low-molecular compounds and polymer compounds. The light emitting material may have a crosslinking group.

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

  Examples of the polymer compound include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthenediyl group, a group represented by the formula (X), a carbazole diyl group, and a phenoxazine diyl. And a polymer compound containing a group, a phenothiazinediyl group, an anthracenediyl group, a pyrenediyl group, and the like.

  The light emitting material may contain a low molecular compound and a high molecular compound, and preferably contains a triplet light emitting complex and a high molecular compound.

  In the composition of the present invention, the content of the light emitting material is usually 0.1 to 400 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the polymer compound of the present invention and does not inhibit light emission and charge transport. Examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

  In the composition of the present invention, the blending amount of the antioxidant is usually 0.001 to 10 parts by weight with respect to 100 parts by weight of the polymer compound of the present invention.

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

<Membrane>
The membrane contains the polymer compound of the present invention.

  The membrane includes an insolubilized membrane obtained by insolubilizing the polymer compound of the present invention in a solvent by crosslinking. The insolubilized film is a film obtained by crosslinking the polymer compound of the present invention by an external stimulus such as heating or light irradiation. Since the insolubilized film is substantially insoluble in a solvent, the insolubilized film can be suitably used for stacking light emitting elements.

  The heating temperature for crosslinking the film is usually 25 to 300 ° C., and the luminance life of the light-emitting element including the film of the present invention is preferably improved, and is preferably 50 to 250 ° C., more preferably 150. ~ 200 ° C.

  Types of light used for light irradiation for crosslinking the film are, for example, ultraviolet light, near ultraviolet light, and visible light.

  The film is suitable as a hole transport layer, a hole injection layer, or a light emitting layer in a light emitting element, and more preferably as a light emitting layer.

  The film is made of an ink, for example, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method. , Flexographic printing, offset printing, ink jet printing, capillary coating, and nozzle coating.

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

<Light emitting element>
The light-emitting device of the present invention is a light-emitting device containing the polymer compound of the present invention, and a light-emitting device containing a polymer compound of the present invention crosslinked within a molecule or between molecules (crosslinked product).
As a structure of the light emitting element of this invention, it has an electrode which consists of an anode and a cathode, and a layer obtained using the polymer compound of this invention provided between this electrode, for example.

[Layer structure]
The layer obtained by using the polymer compound of the present invention is usually one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, preferably a light emitting layer. It is. Each of these layers includes a light emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material. Each of these layers is the same as the above-described film production, in which a light-emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material are dissolved in the above-described solvent and ink is prepared and used. It can be formed using a method.

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

  As materials for the hole transport layer, electron transport layer, light emitting layer, hole injection layer, and electron injection layer, in addition to the polymer compound of the present invention, the above-described hole transport material, electron transport material, light emitting material, respectively. Examples include hole injection materials and electron injection materials.

  The material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer are used as solvents used in forming the layer adjacent to the hole transport layer, the electron transport layer, and the light emitting layer, respectively, in the production of the light emitting element. When dissolved, the material preferably has a cross-linking group in order to avoid dissolution of the material in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

  In the light emitting device of the present invention, as a method 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, when using a low molecular compound, for example, vacuum deposition from powder For example, a method using film formation from a solution or a molten state may be used.

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

[Substrate / Electrode]
The substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed. For example, the substrate is made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, the electrode farthest from the substrate is preferably transparent or translucent.

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

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

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

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

The number average molecular weight (Mn) in terms of polystyrene and the weight average molecular weight (Mw) in terms of polystyrene of the polymer compound were measured by the following methods.
The measurement sample was dissolved in tetrahydrofuran at a concentration of about 0.05% by weight, and 10 μL was injected into size exclusion chromatography (SEC). The mobile phase was run at a flow rate of 1.0 mL / min. As a column, PLgel MIXED-B (manufactured by Polymer Laboratories) was used. A UV-VIS detector (trade name: UV-8320GPC, manufactured by Tosoh Corporation) was used as the detector.

LC-MS was measured by the following method.
The measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and 1 to 10 μL was injected into LC-MS (manufactured by Agilent, trade name: 1100LCMSD) depending on the concentration. The LC-MS mobile phase was used while changing the ratio of acetonitrile and tetrahydrofuran and was allowed to flow at a flow rate of 1.0 mL / min. The column used was SUMPAX ODS Z-CLUE (manufactured by Sumika Chemical Analysis Center, inner diameter: 4.6 mm, length: 250 mm, particle size 3 μm).

TLC-MS was measured by the following method.
A measurement sample is dissolved in any solvent of toluene, tetrahydrofuran, or chloroform at an arbitrary concentration, and coated on a TART plate for DART (manufactured by Techno Applications, trade name: YSK5-100), and TLC-MS (JEOL Ltd.) Product name: JMS-T100TD (The AccuTOF TLC)). 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 5 to 10 mg of a measurement sample, about 0.5 mL of deuterated chloroform, deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N, N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol or methylene chloride. And measured using an NMR apparatus (trade name: INOVA300 or MERCURY 400VX manufactured by Agilent, or product name: ECZ400S manufactured by JEOL Ltd.).

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

  <Synthesis Example 1> Synthesis of Compound L1

(Synthesis of Compound L1b)
Compound L1a was synthesized according to the method described in International Publication No. 2012/088660.
After making the inside of reaction container nitrogen atmosphere, Compound L1a (90 g) and tetrahydrofuran (dehydrated product, 1.6 L) were added and cooled to −68 ° C. with stirring. Then, the n-hexane solution (2.65 mol / L, 90 mL) of n-butyllithium was dripped there, and it stirred for 30 minutes at -68 degreeC. Then, ion-exchange water (8 mL) was dripped there, and it heated up to room temperature over 2 hours, stirring. Thereafter, toluene was added thereto, and the resulting solution was washed with ion-exchanged water and dried over anhydrous sodium sulfate. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was dissolved in a mixed solvent of n-hexane / toluene = 1/1 (volume ratio). Thereafter, activated carbon was added thereto and stirred at 65 ° C. for 1 hour. The obtained mixture was filtered using silica gel, and the obtained filtrate was concentrated under reduced pressure to obtain a white solid (71.4 g) containing Compound L1b. The HPLC area percentage value of the obtained compound L1b was 87.8%.

TLC-MS (DART positive): m / z = 339 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.86 (dd, 1H), 7.79 (d, 1H), 7.54 (d, 1H), 7.41-7 .20 (m, 4H), 2.22-2.12 (m, 4H), 2.01-1.90 (m, 4H), 1.73-1.58 (m, 2H), 1.52 -1.39 (m, 2H).

(Synthesis of Compound L1c)
The reaction vessel was filled with a nitrogen gas atmosphere, then compound L1b (71.4 g), bis (pinacolato) diboron (80.2 g), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane An adduct (10.3 g), potassium acetate (62.0 g) and 1,2-dimethoxyethane (631 mL) were added, and the mixture was stirred at 80 ° C. for 4 hours. After cooling the obtained reaction liquid to room temperature, toluene (950 mL) was added, it filtered with the filter which spread | overlaid Celite, and the obtained filtrate was concentrate | evaporated under reduced pressure. Thereafter, a mixed solvent (630 mL) of hexane / toluene = 1/1 (volume ratio) and activated carbon were added thereto, and the mixture was stirred at 70 ° C. for 1 hour. The obtained mixture was filtered with a filter covered with celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was crystallized using a mixed solvent of toluene and acetonitrile to obtain Compound L1c (52.1 g) as a white solid. The HPLC area percentage value of the obtained compound L1c was 98.1%.

TLC-MS (DART positive): m / z = 387 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 7.94-7.88 (m, 2H), 7.77 (d, 1H), 7.59 (dd, 1H), 7 .39 (dd, 1H), 7.28 (dt, 1H), 7.21 (dt, 1H), 2.24-2.12 (m, 4H), 2.02-1.90 (m, 4H) ), 1.72-1.57 (m, 2H), 1.48-1.33 (m, 14H).

(Synthesis of Compound L1d)
The reaction vessel was filled with a nitrogen gas atmosphere, and then compound L1c (47.1 g), 2,5-dibromopyridine (30.6 g), tetrakis (triphenylphosphine) palladium (0) (2.82 g), toluene (731 mL) ), Tetrahydrofuran (366 mL), tert-butanol (488 mL), ion-exchanged water (244 mL) and 40 wt% tetrabutylammonium hydroxide aqueous solution (316 g) were added, and the mixture was stirred at 50 ° C. for 21 hours. After cooling the obtained reaction liquid to room temperature, toluene was added and the obtained organic layer was washed with ion-exchanged water and dried over anhydrous magnesium sulfate. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid is dissolved in a mixed solvent of toluene / chloroform = 1/2 (volume ratio), stirred at 60 ° C., filtered through a filter with silica gel, and the obtained filtrate is concentrated under reduced pressure. Gave a solid. The obtained solid was crystallized using a mixed solvent of chloroform and methanol to obtain Compound L1d (44.1 g) as a white solid. The obtained HPLC area percentage value of the compound L1d was 97.8%.

TLC-MS (DART positive): m / z = 416 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 8.72 (dd, 1H), 8.03 (d, 1H), 7.99 (d, 1H), 7.93 (dd , 1H), 7.88 (dd, 1H), 7.81 (dd, 1H), 7.68 (dd, 1H), 7.40 (dd, 1H), 7.29 (dt, 1H), 7 .23 (dt, 1H), 2.28-2.14 (m, 4H), 2.07-1.93 (m, 4H), 1.74-1.62 (m, 2H), 1.51 -1.39 (m, 2H).

(Synthesis of Compound L1e)
After making the inside of the reaction vessel a nitrogen gas atmosphere, compound L1d (41.1 g), bis (pinacolato) diboron (37.6 g), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane An adduct (4.8 g), potassium acetate (29.0 g) and 1,2-dimethoxyethane (296 mL) were added, and the mixture was stirred at 80 ° C. for 3.5 hours. After cooling the obtained reaction liquid to room temperature, toluene (593 mL) was added, it filtered with the filter which spread | overlaid Celite, and the obtained filtrate was concentrate | evaporated under reduced pressure. Thereafter, a mixed solvent of hexane / toluene = 1/2 (volume ratio) and activated carbon were added thereto, and the mixture was stirred at 70 ° C. for 2 hours. The obtained mixture was filtered with a filter covered with celite, and the obtained filtrate was concentrated under reduced pressure to obtain a solid. The obtained solid was crystallized using a mixed solvent of toluene and acetonitrile to obtain Compound L1e (32.6 g) as a white solid. The HPLC area percentage value of the obtained compound L1e was 99.5%.

TLC-MS (DART positive): m / z = 464 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 8.94 (dd, 1H), 8.10-8.07 (m, 2H), 8.00 (d, 1H), 7 .94 (dd, 1H), 7.89 (dd, 1H), 7.73 (dd, 1H), 7.40 (dd, 1H), 7.32-7.20 (m, 2H), 2. 30-2.15 (m, 4H), 2.09-1.94 (m, 4H), 1.75-1.60 (m, 2H), 1.51-1.39 (m, 2H), 1.35 (s, 12H).

(Synthesis of Compound L1)
Compound L1f was synthesized according to the method described in JP2011-174062.
After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, compound L1e (3.70 g), compound L1f (2.60 g), tetrakis (triphenylphosphine) palladium (0) (0.09 g), toluene (46.9 g) ) And 20 wt% tetraethylammonium hydroxide aqueous solution (23.6 g) were added, and the mixture was stirred at 70 ° C for 6 hours. The reaction solution L1-1 was obtained by cooling the obtained reaction solution to room temperature.
After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, compound L1e (0.92 g), compound L1f (0.66 g), tetrakis (triphenylphosphine) palladium (0) (0.02 g), toluene (11.8 g) ) And 20 wt% tetraethylammonium hydroxide aqueous solution (5.9 g) were added, and the mixture was stirred at 70 ° C. for 5 hours. The reaction solution L1-2 was obtained by cooling the obtained reaction solution to room temperature.
The reaction solution L1-1 and the reaction solution L1-2 obtained above were mixed, washed with ion-exchanged water, and then dried over anhydrous sodium sulfate. The obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure to obtain a liquid. The obtained liquid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene), and the solvent was removed under reduced pressure to obtain a liquid. The obtained liquid was dried at 50 ° C. under reduced pressure to obtain Compound L1 (4.56 g) as a colorless liquid. The HPLC area percentage value of the obtained compound L1 was 99.5%.

TLC-MS (DART positive): m / z = 582 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 300 MHz): δ (ppm) = 8.94 (d, 1H), 8.15 (d, 1H), 8.08-7.85 (m, 5H), 7 .44 (dd, 1H), 7.36-7.22 (m, 4H), 7.08 (s, 1H), 2.75-2.64 (m, 4H), 2.35-2.17 (M, 4H), 2.16-1.96 (m, 4H), 1.80-1.61 (m, 6H), 1.59-1.26 (m, 14H), 0.97-0 .85 (m, 6H).

  <Synthesis Example 2> Synthesis of metal complexes M1 and M2

Compound M1a was synthesized according to the method described in International Publication No. 2002/066652.
After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, Compound M1a (8.31 g) and 2-ethoxyethanol (429.0 g) were added and heated to 85 ° C. Thereafter, iridium (III) chloride n hydrate (5.00 g) dissolved in ion-exchanged water (150.1 g) was added dropwise thereto, followed by stirring at 100 ° C. for 26 hours. After cooling the obtained reaction liquid to room temperature, the obtained mixture is filtered, the obtained solid is washed with ion-exchanged water and methanol, and the obtained solid is dried at 50 ° C. under reduced pressure to give a yellow solid. (8.46 g) was obtained.
After the light-shielded reaction vessel was filled with a nitrogen gas atmosphere, the yellow solid (5.60 g) obtained above, silver trifluoromethanesulfonate (2.62 g), compound L1 (4.71 g) and diethylene glycol dimethyl ether (45. 1 g) was added and stirred at 70 ° C. for 65 hours 30 minutes. After cooling the obtained reaction liquid to room temperature, methanol was added, it cooled and stirred at 0 degreeC, and the obtained mixture was filtered. Toluene was added to the obtained solid, the obtained mixture was filtered, and the obtained filtrate was concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography (a mixed solvent of toluene and hexane) to obtain a fraction M1-1 and a fraction M2-1.
The solvent of the obtained fraction M1-1 was removed under reduced pressure to obtain a solid. Methanol was added to the obtained solid, the obtained mixture was filtered, and the obtained solid was dried at 50 ° C. under reduced pressure to obtain a metal complex M1 (2.70 g) as an orange solid. The HPLC area percentage value of the obtained metal complex M1 was 99.5% or more.
The solvent of the obtained fraction M2-1 was removed under reduced pressure to obtain a solid. Methanol was added to the obtained solid, the obtained mixture was filtered, and the obtained solid was dried at 50 ° C. under reduced pressure to obtain a metal complex M2 (0.30 g) as an orange solid. The HPLC area percentage value of the obtained metal complex M2 was 98.3%.

(Metal complex M1)
LC-MS (APCI positive): m / z = 1238 [M + H] ^+
1 H-NMR (CD ₂ Cl ₂ , 400 MHz): δ (ppm) = 7.98-7.84 (m, 4H), 7.81 (d, 1H), 7.76 (d, 1H), 7 72-7.62 (m, 5H), 7.59 (dd, 1H), 7.32-7.25 (m, 3H), 7.14 (t, 1H), 7.05-6.92 (M, 5H), 6.89-6.85 (m, 3H), 6.83-6.75 (m, 2H), 2.52 (t, 4H), 2.25-1.81 (m , 8H), 1.71-1.42 (m, 8H), 1.41-1.22 (m, 12H), 0.88 (t, 6H).

(Metal complex M2)
LC-MS (APCI positive): m / z = 1586 [M + H] ⁺
1H-NMR (CD ₂ Cl ₂ , 400 MHz): δ (ppm) = 8.05-7.82 (m, 9H), 7.79 (s, 1H), 7.75-7.65 (m, 2H) ), 7.49 (s, 1H), 7.40-7.31 (m, 3H), 7.27-7.22 (m, 1H), 7.20-7.13 (m, 2H), 7.08-6.89 (m, 11H), 6.73 (t, 1H), 2.61-2.39 (m, 8H), 2.28-1.18 (m, 56H),. 94-0.84 (m, 12H).

<Synthesis Example 3> Synthesis of Metal Complex CM1 and Compounds PM1 to PM9 Metal Complex CM1 was synthesized according to the method described in International Publication No. 2013/021180.
Compound PM1 was synthesized according to the method described in JP 2010-189630 A.
Compound PM2 was synthesized according to the method described in International Publication No. 2009/131255.
Compound PM3 was synthesized according to the method described in JP-T-2007-511636.
Compound PM4 was synthesized according to the method described in JP-A-2008-106241.
Compound PM5 was synthesized according to the method described in JP2012-144722A and JP2012-214732A.
Compound PM6 was synthesized according to the method described in JP 2010-189630 A.
Compound PM7 was synthesized according to the methods described in JP2011-174062A and International Publication No. 2011-093428.
Compound PM8 was synthesized according to the method described in International Publication No. 2005/049546.
Compound PM9 was synthesized according to the method described in International Publication No. 2002/045184.

<Example 1> Synthesis of polymer compound P1 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound PM1 (0.98412 g), Compound PM2 (0.44111 g), Compound PM3 (0.17301 g) , Compound PM4 (0.21409 g), metal complex M1 (0.30538 g), compound PM5 (0.10066 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (5.28 mg) and toluene (31 mL), Heated to 90 ° C.
(Step 2) A 16 wt% tetraethylammonium hydroxide aqueous solution (20.3 g) was added dropwise to the reaction solution, and the mixture was refluxed for 7 hours.
(Step 3) After the reaction, phenylboronic acid (97.5 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.76 mg) were added thereto and refluxed for 14.5.
(Step 4) Then, after cooling, the obtained reaction solution was washed twice with a 10 wt% aqueous hydrochloric acid solution, twice with a 3 wt% aqueous ammonia solution and twice with water, and the obtained solution was added dropwise to methanol. However, precipitation occurred. The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 0.82 g of the polymer compound P1. The polymer compound P2 had a polystyrene-equivalent number average molecular weight of 3.9 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 9.6 × 10 ⁴ .

  The theoretical value obtained from the amount of the raw material used for the polymer compound P1 is that the structural unit derived from the compound PM1, the structural unit derived from the compound PM2, the structural unit derived from the compound PM3, and the compound PM4 The structural unit derived, the structural unit derived from the metal complex M1, and the structural unit derived from the compound PM5 are configured in a molar ratio of 50: 20: 10: 10: 6.11: 3.89. Is a copolymer.

<Example 2> Synthesis of polymer compound P2 (Step 1) in the synthesis of polymer compound P1 was made as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound PM1 (0.15984 g), compound PM6 (0. 25523 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (0.35 mg) and toluene (29 mL) were added and heated to 90 ° C. ”, (Step 2) An aqueous tetraethylammonium oxide solution (14.5 g) was added dropwise and refluxed for 2.5 hours, and then compound PM1 (0.83493 g), compound PM5 (0.77674 g), metal complex M1 (0.49986 g), dichlorobis (tris) -O-methoxyphenylphosphine) palladium (4.94 mg) and toluene (10 mL) were added, and 6 During refluxed. ", Except that the, by the same manner as in the synthesis of the polymer compound P1, to give 0.49g of the polymer compound P2. The polymer compound P2 had a polystyrene-equivalent number average molecular weight of 4.3 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 1.1 × 10 ⁵ .

  The theoretical value obtained from the amount of raw materials used for the polymer compound P2 is that the structural unit derived from the compound PM1, the structural unit derived from the compound PM6, the structural unit derived from the metal complex M1, and the compound PM5 Is a copolymer composed of a molar unit of 50: 10: 10: 30.

Example 3 Synthesis of Polymer Compound P3 (Step 1) After making the inside of the reaction vessel an inert gas atmosphere, Compound PM1 (1.09028 g), Compound PM5 (1.13609 g), Compound PM6 (0.28714 g) , Metal complex M2 (0.05316 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.99 mg) and toluene (34 mL) were added and heated to 90 ° C.
(Step 2) A 10 wt% tetraethylammonium hydroxide aqueous solution (22.4 g) was added dropwise to the reaction solution, and the mixture was refluxed for 4.5 hours.
(Step 3) After the reaction, phenylboronic acid (109.8 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.99 mg) were added thereto and refluxed for 14.5.
(Step 4) Then, after cooling, the obtained reaction solution was washed twice with a 10 wt% aqueous hydrochloric acid solution, twice with a 3 wt% aqueous ammonia solution and twice with water, and the obtained solution was added dropwise to methanol. However, precipitation occurred. The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.35 g of polymer compound P3. The polymer compound P3 had a polystyrene-equivalent number average molecular weight of 5.3 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 1.3 × 10 ⁵ .

  The theoretical value obtained from the amount of charged raw materials for the polymer compound P3 is that the structural unit derived from the compound PM1, the structural unit derived from the compound PM5, the structural unit derived from the compound PM6, and the metal complex M2 Is a copolymer having a molar ratio of 50: 39: 10: 1.

<Comparative Example 1> Synthesis of polymer compound CP1 (Step 1) in the synthesis of polymer compound P1 was made as follows: "After the inside of the reaction vessel was set to an inert gas atmosphere, compound PM1 (0.99420 g), compound PM2 (0. 44108 g), compound PM3 (0.17306 g), compound PM4 (0.21408 g), metal complex CM1 (0.28180 g), compound PM5 (0.10077 g), dichlorobis (tris-o-methoxyphenylphosphine) palladium (5. 28 mg) and toluene (30 mL) were added and heated to 90 ° C. ”(Step 2) was added,“ 20 wt% tetraethylammonium hydroxide aqueous solution (20.1 g) was added dropwise to the reaction solution for 2.5 hours. The polymer compound CP1 was changed to 0.0 by the same method as the synthesis of the polymer compound P1 except that the polymer compound CP1 was refluxed. It was obtained g. The polymer compound CP1 had a polystyrene-equivalent number average molecular weight of 5.0 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 1.2 × 10 ⁵ .

  The high molecular compound CP1 has a theoretical value determined from the amount of raw materials charged. From the structural unit derived from the compound PM1, the structural unit derived from the compound PM2, the structural unit derived from the compound PM3, and the compound PM4. The structural unit derived, the structural unit derived from the metal complex CM1, and the structural unit derived from the compound PM5 are configured in a molar ratio of 50: 20: 10: 10: 6.11: 3.89. Is a copolymer.

<Synthesis Example 4> Synthesis of Polymer Compound IP1 The polymer compound IP1 is prepared by using the compound PM7, the compound PM8, the compound PM9, and the compound PM4 and the Suzuki reaction according to the method described in JP2012-144722A. Was synthesized.

  The polymer compound IP1 has a theoretical value obtained from the amount of the charged raw materials, a structural unit derived from the compound PM7, a structural unit derived from the compound PM8, a structural unit derived from the compound PM9, and the compound PM4. The derived structural unit is a copolymer composed of a molar ratio of 50: 30: 12.5: 7.5.

<Example D1> Fabrication and evaluation of light-emitting element D1 (production of light-emitting element D1)
(Formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. On the anode, ND-3202 (manufactured by Nissan Chemical Industries), which is a hole injection material, was formed into a film with a thickness of 65 nm by spin coating. In an air atmosphere, a hole injection layer was formed by heating on a hot plate at 50 ° C. for 3 minutes and further heating at 230 ° C. for 15 minutes.

(Formation of hole transport layer)
Polymer compound IP1 was dissolved in xylene at a concentration of 0.70% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
Polymer compound P1 was dissolved in xylene at a concentration of 2.0% by weight. Using the obtained xylene solution, a film having a thickness of 80 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 150 ° C. for 10 minutes in a nitrogen gas atmosphere. .

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

(Evaluation of light emitting element D1)
EL light emission was observed by applying a voltage to the light emitting element D1. The external quantum efficiency at 100 cd / m ² was 11.2%, and the CIE chromaticity coordinates were (x, y) = (0.53, 0.47). When the light emitting element D1 is driven at a constant current (0.1 mA), the time required for the emission luminance to decrease to 80% with respect to the emission luminance immediately after the start of driving (hereinafter referred to as “luminance lifetime LT80”). 9.8 hours. These results are shown in Table 2. In addition, an emission spectrum of the light-emitting element D1 at 100 cd / m ² is shown in FIG.

<Example D2> Production and Evaluation of Light-Emitting Element D2 A light-emitting element D2 was produced in the same manner as in Example D1, except that the polymer compound P2 was used instead of the polymer compound P1 in Example D1.
EL light emission was observed by applying a voltage to the light emitting element D2. The external quantum efficiency at 100 cd / m ² was 10.1%, and the CIE chromaticity coordinates were (x, y) = (0.53, 0.47). When the light-emitting element D2 was driven at a constant current (0.1 mA), the luminance life LT80 was 21 hours. These results are shown in Table 2. In addition, an emission spectrum of the light-emitting element D2 at 100 cd / m ² is shown in FIG.

<Example D3> Production and Evaluation of Light-Emitting Element D3 A light-emitting element D3 was produced in the same manner as in Example D1, except that the polymer compound P3 was used instead of the polymer compound P1 in Example D1.
EL light emission was observed by applying a voltage to the light emitting element D3. The external quantum efficiency at 100 cd / m ² was 5.05%, and the CIE chromaticity coordinates were (x, y) = (0.51, 0.46). When the light-emitting element D3 was driven at a constant current (0.1 mA), the luminance life LT80 was 9.2 hours. These results are shown in Table 2. In addition, an emission spectrum of the light-emitting element D3 at 100 cd / m ² is shown in FIG.

<Comparative Example CD1> Production and Evaluation of Light Emitting Element CD1 A light emitting element CD1 was produced in the same manner as in Example D1, except that the polymer compound CP1 was used instead of the polymer compound P1 in Example D1.
EL light emission was observed by applying a voltage to the light emitting device CD1. The external quantum efficiency at 100 cd / m ² was 6.82%, and the CIE chromaticity coordinates were (x, y) = (0.31, 0.64). When the light-emitting element CD1 was driven at a constant current (0.1 mA), the luminance life LT80 was 2.7 hours. These results are shown in Table 2. In addition, an emission spectrum of the light-emitting element CD1 at 100 cd / m ² is shown in FIG.

  From these results, the light emitting device obtained using the polymer compounds P1, P2 and P3 of the present invention is superior in luminance life and color purity as compared with the light emitting device obtained using the polymer compound CP1. Recognize.

  ADVANTAGE OF THE INVENTION According to this invention, the polymer compound etc. which are useful for manufacture of the light emitting element which is excellent in the brightness lifetime can be provided.

Claims (12)

At least selected from the group consisting of a structural unit represented by formula (3G), a structural unit represented by formula (1G), a structural unit represented by formula (2G), and a structural unit represented by formula (4G). A polymer compound containing one type of structural unit.

[Where:
M ^1G is a group represented by formula (1), formula (2) or formula (3), wherein n ₁ ring A, n ₃ ring B ¹ and n ₃ ring are present. The bond which B ² may have and the bond which R ⁵ , R ⁶ , R ⁷ and R ⁸ each having n ₁ may have represent a group having a total of one bond. .
M ^2G is a group represented by formula (1), formula (2) or formula (3), wherein n ₁ ring A, n ₃ ring B ¹ and n ₃ ring are present. B ² represents a bond which B ² may have, and a bond which R ⁵ , R ⁶ , R ⁷ and R ⁸ each having n ₁ may have have a total of two bonds. .
M ^3G is a group represented by formula (1), formula (2) or formula (3), wherein n ₁ ring A, n ₃ ring B ¹ and n ₃ ring are present. B ² represents a bond that may have and a bond that n ₁ each of R ⁵ , R ⁶ , R ⁷ and R ⁸ may have a total of three bonds. .
L ¹ , L ² and L ³ are each independently an oxygen atom, a sulfur atom, a group represented by —N (R ^A ) —, a group represented by —C (R ^B ) ₂ —, —C ( R ^B ) ═C (R ^B ) —, a group represented by —C≡C—, an arylene group or a divalent heterocyclic group, and these groups have a substituent. Also good. R ^A represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. R ^B represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^B may be the same or different, and may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. When a plurality of L ¹ , L ² and L ³ are present, they may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups optionally have a substituent.
n ^a1 , n ^b1 and n ^c1 each independently represent an integer of 0 or more. ]

[Where:
M represents an iridium atom or a platinum atom.
n ₁ represents ₁ , 2 or 3. n ₂ and n ₃ each independently represents 0, 1 or 2. When M is an iridium atom, n ₁ + n ₂ + n ₃ is 3, and when M is a platinum atom, n ₁ + n ₂ + n ₃ is 2.
X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ each independently represent a nitrogen atom or a carbon atom. However, at least two of X ⁵ , X ⁶ , X ⁷ and X ⁸ are carbon atoms. When there are a plurality of X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ , they may be the same or different. However, when X ¹ is a nitrogen atom, R ¹ does not exist, when X ² is a nitrogen atom, R ² does not exist, and when X ³ is a nitrogen atom, R ³ does not exist and X ⁴ is In the case of a nitrogen atom, R ⁴ does not exist, when X ⁵ is a nitrogen atom, R ⁵ does not exist, when X ⁶ is a nitrogen atom, R ⁶ does not exist, and when X ⁷ is a nitrogen atom, R ⁷ does not exist, and when X ⁸ is a nitrogen atom, R ⁸ does not exist.
R ¹ , R ² , R ³ and R ⁴ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. These groups may have a substituent. R ¹ and R ² , R ³ and R ⁴ may be bonded to each other to form a ring together with the atoms to which they are bonded. When there are a plurality of R ¹ , R ² , R ³ and R ⁴ , they may be the same or different.
R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently a bond, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent heterocyclic group. Or, it represents a halogen atom, and these groups may have a substituent. R ⁵ and R ⁶ , R ⁶ and R ⁷ , and R ⁷ and R ⁸ may be bonded to each other to form a ring together with the atoms to which they are bonded. When a plurality of R ⁵ , R ⁶ , R ⁷ and R ⁸ are present, they may be the same or different.
One of X ^a and X ^b represents a single bond and the other is ^{-CR 11 R 12 -CR 13 R 14} - represents a group represented by. R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. These groups may have a substituent. However, at least one selected from the group consisting of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ is an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent heterocyclic ring. A group or a halogen atom. R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , R ¹¹ and R ¹³ , and R ¹² and R ¹⁴ may be bonded to each other to form a ring together with the atoms to which they are bonded. When ^a plurality of X ^a and X ^b are present, they may be the same or different.
Each of the rings A independently represents a 5-membered or 6-membered aromatic heterocyclic ring, and the ring may have a bond or may have a substituent. When a plurality of rings A are present, they may be the same or different.
Ring B ¹ represents a 5-membered or 6-membered aromatic heterocyclic ring, and the ring may have a bond or may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings B ¹ are present, they may be the same or different.
Ring B ² represents a 5-membered or 6-membered aromatic hydrocarbon ring or aromatic heterocycle, and the ring may have a bond or may have a substituent. When a plurality of such substituents are present, they may be the same or different, and may be bonded to each other to form a ring together with the atoms to which each is bonded. When a plurality of rings B ² are present, they may be the same or different.
The substituent that ring B ¹ may have and the substituent that ring B ² may have may be bonded to each other to form a ring together with the atoms to which they are bonded.
E ¹ and E ² each independently represent a nitrogen atom or a carbon atom. When a plurality of E ¹ and E ² are present, they may be the same or different. However, at least one of E ¹ and E ² is a carbon atom.
A ¹ -G ¹ -A ² represents an anionic bidentate ligand. A ¹ and A ² each independently represents a carbon atom, an oxygen atom or a nitrogen atom, and these atoms may be atoms constituting a ring. G ¹ represents a single bond or an atomic group constituting a bidentate ligand together with A ¹ and A ² . When a plurality of A ¹ -G ¹ -A ² are present, they may be the same or different. ] The polymer compound according to claim 1, wherein the group represented by the formula (1) is a group represented by the following formula (1-3) or the formula (1-4).

[Where:
_{M, n 1, n 2,} n 3, X 1, X 4, X 5, X 6, X 7, X 8, R 1, R 4, R 5, R 6, R 7, R 8, ring A, Ring B ¹ , ring B ² , E ¹ , E ² and A ¹ -G ¹ -A ² represent the same meaning as described above.
m ₁ and m ₂ each independently represents an integer of 1 to 5. When a plurality of m ₁ and m ₂ are present, they may be the same or different.
R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group or halogen atom. These groups may have a substituent. When a plurality of R ¹⁵ , R ¹⁶ , R ¹⁷ and R ¹⁸ are present, they may be the same or different. ] The polymer compound according to claim 1 or 2, wherein X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ are carbon atoms.   The ring A may have a pyridine ring which may have a substituent, a pyrimidine ring which may have a substituent, a quinoline ring which may have a substituent, or a substituent. The polymer compound according to any one of claims 1 to 3, which is an isoquinoline ring, an imidazole ring which may have a substituent, or a triazole ring which may have a substituent. The ring B ¹ is a pyridine ring which may have a substituent, and the ring B ² is a benzene ring which may have a substituent. The polymer compound according to one item.   6. The composition according to claim 1, comprising at least one structural unit selected from the group consisting of the structural unit represented by the formula (3G) and the structural unit represented by the formula (1G). High molecular compound. The polymer compound according to claim 1, wherein n ₃ = 0. The high molecular compound as described in any one of Claims 1-7 which further contains the structural unit represented by a formula (Y).

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ] The polymer compound according to any one of claims 1 to 8, further comprising a structural unit having at least one crosslinking group selected from the group A of crosslinking groups.
(Crosslinking group A group)

[Wherein, R ^XL represents a methylene group, an oxygen atom or a sulfur atom. n ^XL represents an integer of 0 to 5. When a plurality of R ^XL are present, they may be the same or different, and when a plurality of n ^XL are present, they may be the same or different. * 1 represents a binding position. These crosslinking groups may have a substituent. ]   The polymer compound according to claim 9, wherein the structural unit having a crosslinking group is a structural unit having a crosslinking group represented by the formula (XL-17). The polymer compound according to any one of claims 1 to 10,
A composition comprising a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and at least one material selected from the group consisting of a solvent.   The light emitting element containing the high molecular compound as described in any one of Claims 1-10, or its crosslinked body.

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