JP7213181B2 - Polymer compound useful for light-emitting device and its manufacture - Google Patents

Description

TECHNICAL FIELD The present invention relates to a light-emitting device and a polymer compound useful for manufacturing the device.

Light-emitting elements such as organic electroluminescence elements can be suitably used for display and lighting applications, and are being researched and developed. For example, Patent Document 1 discloses a light-emitting device having an organic layer containing a polymer compound (HT-1) and a light-emitting layer containing a polymer compound containing a structural unit represented by formula (C-1). is described.

JP 2010-196040 A

However, the light-emitting device described above does not necessarily have a sufficient external quantum efficiency.
Accordingly, an object of the present invention is to provide a light-emitting device with excellent external quantum efficiency.

The present invention provides the following [1] to [14].

［式中、Ｒ^XLは、メチレン基、酸素原子又は硫黄原子を表し、ｎ^XLは、０～５の整数を表す。Ｒ^XLが複数存在する場合、それらは同一でも異なっていてもよく、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。］
［２］前記架橋材料が、前記架橋基Ａ群から選ばれる少なくとも１種の架橋基を有する架橋構成単位を含む高分子化合物であり、且つ、前記架橋構成単位が、式（２）で表される構成単位又は式（２’）で表される構成単位である、［１］に記載の発光素子。

［式中、
ｎＡは０～５の整数を表し、ｎは１又は２を表す。ｎＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ³は、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^Aは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、－Ｎ(Ｒ’)－で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^Aが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘは、前記架橋基Ａ群から選ばれる架橋基を表す。Ｘが複数存在する場合、それらは同一でも異なっていてもよい。］

［式中、
ｍＡは０～５の整数を表し、ｍは１～４の整数を表し、ｃは０又は１を表す。ｍＡが複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ⁵は、芳香族炭化水素基、複素環基、又は、芳香族炭化水素環と複素環とが直接結合した基を表し、これらの基は置換基を有していてもよい。
Ａｒ⁴及びＡｒ⁶は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ⁴、Ａｒ⁵及びＡｒ⁶はそれぞれ、該基が結合している窒素原子に結合している該基以外の基と、直接結合又は酸素原子若しくは硫黄原子を介して結合して、環を形成していてもよい。
Ｋ^Aは、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、－Ｎ(Ｒ’)－で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ’は、前記と同じ意味を表す。Ｋ^Aが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘ’は、前記架橋基Ａ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｘ’が複数存在する場合、それらは同一でも異なっていてもよい。但し、少なくとも１つのＸ’は、前記架橋基Ａ群から選ばれる架橋基である。］
［３］前記架橋材料が、前記架橋基Ａ群から選ばれる少なくとも１種の架橋基を有する低分子化合物であり、且つ、前記低分子化合物が式（３）で表される低分子化合物である、［１］に記載の発光素子。

［式中、
ｍ^B1及びｍ^B2は、それぞれ独立に、０以上１０以下の整数を表す。ｍ^B3は、０以上５以下の整数を表す。複数存在するｍ^B1は、同一でも異なっていてもよい。ｍ^B3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。
Ａｒ⁷は、芳香族炭化水素基、複素環基、又は、芳香族炭化水素環と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。Ａｒ⁷が複数存在する場合、それらは同一でも異なっていてもよい。
Ｌ^B1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、－Ｎ(Ｒ''')－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^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。
Ｘ''は、前記架橋基Ａ群から選ばれる架橋基、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＸ''は、同一でも異なっていてもよい。但し、複数存在するＸ''のうち、少なくとも１つは、前記架橋基Ａ群から選ばれる架橋基である。］
［４］前記低分子化合物（Ｔ）から１個以上の水素原子を除いてなる基を含む構成単位が、式（１Ｃ）で表される構成単位、式（２Ｃ）で表される構成単位、式（３Ｃ）で表される構成単位又は式（４Ｃ）で表される構成単位である、［１］～［３］のいずれかに記載の発光素子。

［式中、
Ｔ^1Cは、前記低分子化合物（Ｔ）から１個の水素原子を除いてなる基を表す。
Ｌ^Cは、酸素原子、硫黄原子、－Ｎ（Ｒ^A）－、－Ｃ（Ｒ^B）₂－、－Ｃ（Ｒ^B）＝Ｃ（Ｒ^B）－、－Ｃ≡Ｃ－、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Aは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Bは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Bは、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。Ｌ^Cが複数存在する場合、それらは同一でも異なっていてもよい。
ｎ^c1は０以上１０以下の整数を表す。］

［式中、
Ｔ^1Cは、前記と同じ意味を表す。
Ｌ^d及びＬ^eは、それぞれ独立に、酸素原子、硫黄原子、－Ｎ（Ｒ^A）－、－Ｃ（Ｒ^B）₂－、－Ｃ（Ｒ^B）＝Ｃ（Ｒ^B）－、－Ｃ≡Ｃ－、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^A及びＲ^Bは、前記と同じ意味を表す。Ｌ^d及びＬ^eが複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
ｎ^d1及びｎ^e1は、それぞれ独立に、０以上１０以下の整数を表す。複数存在するｎ^d1は、同一でも異なっていてもよい。
Ａｒ^1Mは、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。］

［式中、
Ｌ^d及びｎ^d1は、前記と同じ意味を表す。
Ｔ^2Cは、前記低分子化合物（Ｔ）から２個の水素原子を除いてなる基を表す。］

［式中、
Ｌ^d及びｎ^d1は、前記と同じ意味を表す。
Ｔ^3Cは、前記低分子化合物（Ｔ）から３個の水素原子を除いてなる基を表す。］
［５］前記高分子化合物（ＴＰ）が、式(Ｙ)で表される構成単位を更に含む、［１］～［４］のいずれかに記載の発光素子。

［式中、Ａｒ^Y1は、置換基を有していてもよいアリーレン基を表す。］
［６］前記式(Ｙ)で表される構成単位が、式(Y-1)、式(Y-2)又は式(Y-3)で表される構成単位である、［５］に記載の発光素子。

［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又はアリール基を表し、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。
但し、少なくとも１つのＲ^Y1は水素原子ではない。］

［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又はアリール基を表し、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。
但し、少なくとも１つのＲ^Y1は水素原子ではない。］

［式中、
Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。
但し、少なくとも１つのＲ^Y1は水素原子ではない。］
［７］前記低分子化合物（Ｔ）の振動子強度が０．０００１以上１以下である、［１］～［６］のいずれかに記載の発光素子。
［８］前記低分子化合物（Ｔ）が式（Ｔ－１）で表される低分子化合物である、［１］～［７］のいずれかに記載の発光素子。

［式中、
ｎ^T1は、０以上５以下の整数を表す。ｎ^T1が複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ^T1は、置換アミノ基、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。Ａｒ^T1が複数存在する場合、それらは同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。但し、Ａｒ^T1の少なくとも１つは、置換アミノ基であるか、或いは、二重結合を有さない窒素原子を環内に含み、且つ、＝Ｎ－で表される基、ホウ素原子、－Ｃ（＝Ｚ^T1）－で表される基、－Ｓ（＝Ｏ）－で表される基、－Ｓ（＝Ｏ）₂－で表される基、及び、式（Ｐ）：

で表される基を環内に含まない、１価の複素環基である。Ｚ^T1は、酸素原子、硫黄原子又は＝ＮＲ^ZT1で表される基を表す。Ｒ^ZT1は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。
Ｌ^T1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、－Ｎ(Ｒ^T1')－で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ^T1'は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^T1が複数存在する場合、それらは同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。
Ａｒ^T2は、ホウ素原子、－Ｃ（＝Ｚ^T1）－で表される基、－Ｓ（＝Ｏ）－で表される基、－Ｓ（＝Ｏ）₂－で表される基、前記式（Ｐ）で表される基、電子求引性基を有する芳香族炭化水素基、ホウ素原子を環内に含む複素環基、又は、＝Ｎ－で表される基を環内に含む複素環基であり、これらの基は置換基を有していてもよい。
ｎ^T2は、１以上１５以下の整数を表す。但し、Ａｒ^T2がホウ素原子又は前記式（Ｐ）で表される基である場合、ｎ^T2は３である。Ａｒ^T2が－Ｃ（＝Ｚ^T1）－で表される基、－Ｓ（＝Ｏ）－で表される基、又は、－Ｓ（＝Ｏ）₂－で表される基である場合、ｎ^T2は２である。
Ａｒ^T1とＬ^T1とは直接結合して、又は、２価の基を介して結合して、環を形成してもよい。Ａｒ^T2とＬ^T1とは直接結合して、又は、２価の基を介して結合して、環を形成してもよい。Ａｒ^T1とＡｒ^T2とは直接結合して、又は、２価の基を介して結合して、環を形成してもよい。］
［９］前記第１の有機層が、ホスト材料、正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料及び酸化防止剤からなる群より選ばれる少なくとも１種を更に含有する、［１］～［８］のいずれかに記載の発光素子。
［１０］前記第１の有機層が、前記発光材料として、式Ir-1で表される燐光発光性化合物を含有する、［９］に記載の発光素子。

［式中、
Ｒ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7及びＲ^D8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。Ｒ^D1、Ｒ^D2、Ｒ^D3、Ｒ^D4、Ｒ^D5、Ｒ^D6、Ｒ^D7及びＲ^D8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。
－Ａ^D1---Ａ^D2－は、アニオン性の２座配位子を表し、Ａ^D1及びＡ^D2は、それぞれ独立に、イリジウム原子と結合する炭素原子、酸素原子または窒素原子を表し、これらの原子は環を構成する原子であってもよい。－Ａ^D1---Ａ^D2－が複数存在する場合、それらは同一でも異なっていてもよい。
ｎ_D1は、１、２又は３を表す。
ｎ_D2は、１又は２を表す。］
［１１］前記第１の有機層が、前記発光材料として、蛍光発光性化合物を含有する、［９］に記載の発光素子。
［１２］前記第１の有機層と前記第２の有機層とが隣接している、［１］～［１１］のいずれかに記載の発光素子。
［１３］前記第２の有機層が、前記陽極及び前記第１の有機層との間に設けられた層である、［１］～［１２］のいずれかに記載の発光素子。
［１４］式（Ｓ２－１’）で表される構成連鎖を含み、且つ、
前記構成連鎖が、最低三重項励起状態のエネルギー準位と最低一重項励起状態のエネルギー準位との差の絶対値が０．５ｅＶ以下である低分子化合物（Ｔ）から１個以上の水素原子を除いてなる基を含む構成単位を含む、高分子化合物（以下、「高分子化合物Ａ」と言う）。

［式中、
ｋは、０又は１を表す。複数存在するｋは、同一でも異なっていてもよい。
ｍ^DA1は、０以上１０以下の整数を表す。ｍ^DA1が複数存在する場合、それらは同一でも異なっていてもよい。
ｎ^d1は、０以上１０以下の整数を表す。複数存在するｎ^d1は、同一でも異なっていてもよい。
ｎ^T1は、１又は２を表す。
Ａｒ^DA1は、置換基を有していてもよいアリーレン基を表す。Ａｒ^DA1が複数存在する場合、それらは同一でも異なっていてもよい。
Ａｒ^L1は、Ｔ^DAで表される基から１個の水素原子を除いてなる基を表す。Ａｒ^L1が複数存在する場合、それらは同一でも異なっていてもよい。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。
Ａｒ^TWは、前記式(Y-1)、前記式(Y-2)又は前記式(Y-3)で表される構成単位を表す。複数存在するＡｒ^TWは、同一でも異なっていてもよい。
Ｌ^dは、酸素原子、硫黄原子、－Ｎ（Ｒ^A）－、－Ｃ（Ｒ^B）₂－、－Ｃ（Ｒ^B）＝Ｃ（Ｒ^B）－、－Ｃ≡Ｃ－、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^dが複数存在する場合、それらは同一でも異なっていてもよい。Ｒ^Aは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^Bは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Bは、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｌ^T1は、アルキレン基、シクロアルキレン基、アリーレン基、２価の複素環基、－Ｎ(Ｒ^T1')－で表される基、酸素原子又は硫黄原子を表し、これらの基は置換基を有していてもよい。Ｒ^T1'は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｌ^T1が複数存在する場合、それらは同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。
環Ｒ^T1及び環Ｒ^T2は、それぞれ独立に、－Ｃ（＝Ｚ^T1）－で表される基を環内に含まない芳香族炭化水素環、又は、＝Ｎ－で表される基、ホウ素原子、－Ｃ（＝Ｚ^T1）－で表される基、－Ｓ（＝Ｏ）－で表される基、－Ｓ（＝Ｏ）₂－で表される基、及び、前記式（Ｐ）で表される基を環内に含まない複素環を表し、これらの環は置換基を有していてもよい。
Ｚ^T1は、酸素原子、硫黄原子又は＝ＮＲ^ZT1で表される基を表す。Ｒ^ZT1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。
Ｘ^T1は、単結合、酸素原子、硫黄原子、－Ｎ(Ｒ^XT1)－で表される基、又は、－Ｃ(Ｒ^XT1')₂－で表される基を表す。Ｒ^XT1及びＲ^XT1'は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^XT1'は、同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｒ^XT1と環Ｒ^T1が有していてもよい置換基、Ｒ^XT1と環Ｒ^T2が有していてもよい置換基、Ｒ^XT1'と環Ｒ^T1が有していてもよい置換基、及び、Ｒ^XT1'と環Ｒ^T2が有していてもよい置換基は、それぞれ直接結合して、又は、２価の基を介して結合して、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。
Ｚ³は、－Ｎ＝で表される基、又は－ＣＨ＝で表される基を表す。複数存在するＺ³は、同一でも異なっていてもよい。但し、少なくとも１つのＺ³は、－Ｎ＝で表される基を表す。[1] A light-emitting element having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode. hand,
the first organic layer is a layer containing a polymer compound (TP),
the second organic layer is a layer containing a crosslinked body of a crosslinkable material,
One low-molecular compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less as the polymer compound (TP) Including a structural unit containing a group excluding the above hydrogen atoms,
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from Group A, or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from Group A. The above-mentioned light-emitting device.

<Crosslinking group A group>

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When multiple R ^XL are present, they may be the same or different, and when multiple n ^XL are present, they may be the same or different. *1 represents the binding position. These cross-linking groups may have substituents. ]
[2] The cross-linking material is a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A, and the cross-linking structural unit is represented by formula (2). or a structural unit represented by formula (2′), the light-emitting device according to [1].

[In the formula,
nA represents an integer of 0 to 5, n represents 1 or 2; When multiple nAs are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R')-, an oxygen atom or a sulfur atom, and these groups have substituents. You may have R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^A are present, they may be the same or different.
X represents a cross-linking group selected from the cross-linking group A group. When there are multiple X's, they may be the same or different. ]

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When multiple mA are present, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or through an oxygen atom or a sulfur atom to form a ring. You may have
K ^A represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R')-, an oxygen atom or a sulfur atom, and these groups have substituents. You may have R' has the same meaning as above. When multiple K ^A are present, they may be the same or different.
X' represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group selected from the bridging group A group, and these groups may have a substituent. . When multiple X' are present, they may be the same or different. However, at least one X' is a cross-linking group selected from the cross-linking group A. ]
[3] The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from the cross-linking group A, and the low-molecular-weight compound is a low-molecular-weight compound represented by formula (3). , the light-emitting device according to [1].

[In the formula,
m ^B1 and m ^B2 each independently represent an integer of 0 or more and 10 or less. m ^B3 represents an integer of 0 or more and 5 or less. A plurality of m ^B1 may be the same or different. When multiple m ^B3 are present, they may be the same or different.
Ar ⁷ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent. When multiple Ar ⁷ are present, they may be the same or different.
L ^B1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R''')-, an oxygen atom or a sulfur atom, and these groups are substituents may have R''' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^B1 are present, they may be the same or different.
X'' represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group selected from the bridging group A group, and these groups may have a substituent. good. Multiple X'' may be the same or different. However, at least one of the plurality of X'' is a cross-linking group selected from the cross-linking group A. ]
[4] A structural unit containing a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (T) is a structural unit represented by formula (1C), a structural unit represented by formula (2C), The light-emitting device according to any one of [1] to [3], which is a structural unit represented by formula (3C) or a structural unit represented by formula (4C).

[In the formula,
T ^1C represents a group obtained by removing one hydrogen atom from the low-molecular-weight compound (T).
L ^C is an oxygen atom, a sulfur atom, -N(R ^A )-, -C(R ^B ) ₂ -, -C(R ^B )=C(R ^B )-, -C≡C-, an arylene group or It represents a divalent heterocyclic group, and these groups may have a substituent. ^RA 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. ^RB 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 RB's 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 multiple L ^C are present, they may be the same or different.
n ^c1 represents an integer of 0 or more and 10 or less. ]

[In the formula,
T ^1C has the same meaning as above.
L ^d and L ^e each independently represent an oxygen atom, a sulfur atom, —N(R ^A )—, —C(R ^B ) ₂ —, —C(R ^B )=C(R ^B )—, —C ≡C— represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. ^RA and ^RB have the same meaning as above. When multiple L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more and 10 or less. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T ^2C represents a group obtained by removing two hydrogen atoms from the low-molecular-weight compound (T). ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T ^3C represents a group obtained by removing three hydrogen atoms from the low-molecular-weight compound (T). ]
[5] The light-emitting device according to any one of [1] to [4], wherein the polymer compound (TP) further contains a structural unit represented by formula (Y).

[In the formula, Ar ^Y1 represents an arylene group which may have a substituent. ]
[6] Described in [5], wherein the structural unit represented by formula (Y) is a structural unit represented by formula (Y-1), formula (Y-2) or formula (Y-3) light-emitting element.

[In the formula,
R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent. A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
However, at least one R ^Y1 is not a hydrogen atom. ]

[In the formula,
R ^Y1 has the same meaning as above.
X ^Y1 represents a group represented by -C(R ^Y2 ) ₂ -, -C(R ^Y2 )=C(R ^Y2 )- or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -. R ^Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent. A plurality of R ^Y2 may be the same or different, and R ^Y2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
However, at least one R ^Y1 is not a hydrogen atom. ]

[In the formula,
R ^Y1 and X ^Y1 have the same meaning as above.
However, at least one R ^Y1 is not a hydrogen atom. ]
[7] The light-emitting device according to any one of [1] to [6], wherein the low-molecular-weight compound (T) has an oscillator strength of 0.0001 or more and 1 or less.
[8] The light-emitting device according to any one of [1] to [7], wherein the low-molecular-weight compound (T) is a low-molecular-weight compound represented by formula (T-1).

[In the formula,
n ^T1 represents an integer of 0 or more and 5 or less. When multiple n ^T1 are present, they may be the same or different.
Ar ^T1 represents a substituted amino group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple Ar ^T1 are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. provided that at least one of Ar ^T1 is a substituted amino group or a group containing a nitrogen atom having no double bond in the ring and represented by =N-, a boron atom, -C A group represented by (=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, and formula (P):

It is a monovalent heterocyclic group that does not contain a group represented by in the ring. Z ^T1 represents an oxygen atom, a sulfur atom or a group represented by =NR ^ZT1 . R ^ZT1 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.
L ^T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^T1 ')-, an oxygen atom or a sulfur atom, and these groups are substituents; may have. R ^T1 ' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^T1 are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring.
Ar ^T2 is a boron atom, a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, the above formula A group represented by (P), an aromatic hydrocarbon group having an electron-withdrawing group, a heterocyclic group containing a boron atom in the ring, or a heterocyclic ring containing a group represented by =N- in the ring groups, and these groups may have a substituent.
n ^T2 represents an integer of 1 or more and 15 or less. However, n ^T2 is 3 when Ar ^T2 is a boron atom or a group represented by the formula (P). When Ar ^T2 is a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, or a group represented by -S(=O) ₂ -, n ^T2 is two.
Ar ^T1 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T2 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T1 and Ar ^T2 may be directly bonded or bonded via a divalent group to form a ring. ]
[9] The first organic layer further contains at least one selected from the group consisting of a host material, a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, and an antioxidant. The light-emitting device according to any one of [1] to [8].
[10] The light-emitting device according to [9], wherein the first organic layer contains a phosphorescent compound represented by Formula Ir-1 as the light-emitting material.

[In the formula,
R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 and R ^D8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryl It represents an oxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When there are a plurality of R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 and R ^D8 , they may be the same or different.
-A ^D1 ---A ^D2 - represents an anionic bidentate ligand, and A ^D1 and A ^D2 each independently represent a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom, may be atoms constituting a ring. When there are a plurality of -A ^D1 ---A ^D2 -, they may be the same or different.
n _D1 represents 1, 2 or 3;
n _D2 represents 1 or 2; ]
[11] The light-emitting device according to [9], wherein the first organic layer contains a fluorescent compound as the light-emitting material.
[12] The light emitting device according to any one of [1] to [11], wherein the first organic layer and the second organic layer are adjacent to each other.
[13] The light emitting device according to any one of [1] to [12], wherein the second organic layer is a layer provided between the anode and the first organic layer.
[14] including a constituent chain represented by formula (S2-1′), and
one or more hydrogen atoms from a low-molecular-weight compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state of the constituent chain is 0.5 eV or less A polymer compound (hereinafter referred to as "polymer compound A") containing a structural unit containing a group excluding

[In the formula,
k represents 0 or 1; Multiple k may be the same or different.
^mDA1 represents an integer of 0 or more and 10 or less. When multiple ^mDA1 are present, they may be the same or different.
^nd1 represents an integer of 0 or more and 10 or less. A plurality of n ^d1 may be the same or different.
n ^T1 represents 1 or 2;
Ar ^DA1 represents an optionally substituted arylene group. When multiple Ar ^DA1 are present, they may be the same or different.
Ar ^L1 represents a group obtained by removing one hydrogen atom from the group represented by ^TDA . When multiple Ar ^L1 are present, they may be the same or different. ^TDA represents an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.
Ar ^TW represents a structural unit represented by the formula (Y-1), the formula (Y-2) or the formula (Y-3). A plurality of Ar ^TWs may be the same or different.
L ^d is an oxygen atom, a sulfur atom, -N(R ^A )-, -C(R ^B ) ₂ -, -C(R ^B )=C(R ^B )-, -C≡C-, an arylene group or It represents a divalent heterocyclic group, and these groups may have a substituent. When multiple L ^d are present, they may be the same or different. ^RA 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. ^RB 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 RB's 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.
L ^T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^T1 ')-, an oxygen atom or a sulfur atom, and these groups are substituents; may have. R ^T1 ' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^T1 are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring.
Ring R ^T1 and ring R ^T2 are each independently an aromatic hydrocarbon ring that does not contain a group represented by -C(=Z ^T1 )- in the ring, or a group represented by =N-, boron an atom, a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, and the formula (P) represents a heterocyclic ring that does not contain a group represented by in the ring, and these rings may have a substituent.
Z ^T1 represents an oxygen atom, a sulfur atom or a group represented by =NR ^ZT1 . R ^ZT1 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.
X ^T1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by -N(R ^XT1 )-, or a group represented by -C(R ^XT1 ') ₂ -. R ^XT1 and R ^XT1 ' each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or It represents a cyano group, and these groups may have a substituent. A plurality of R ^XT1 ' 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.
a substituent that R ^XT1 and ring R ^T1 may have, a substituent that R ^XT1 and ring R ^T2 may have, a substituent that R ^XT1 ' and ring R ^T1 may have, and , R ^XT1 ' and the substituents that the ring R ^T2 may have are directly bonded or bonded via a divalent group to form a ring together with the atoms to which they are bonded good too.
Z ³ represents a group represented by -N= or a group represented by -CH=. A plurality of Z ³ may be the same or different. However, at least one Z ³ represents a group represented by -N=.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a light-emitting device with excellent external quantum efficiency and a polymer compound useful for the production thereof.

Preferred embodiments of the present invention are described in detail below.

<Description of common terms>
Terms commonly used in this specification have the following meanings unless otherwise specified.

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

A hydrogen atom may be a deuterium atom or a protium atom.
In the formulas representing the metal complexes, solid lines representing bonds with the central metal mean covalent bonds or coordinate bonds.

A "polymer compound" means a polymer having a molecular weight distribution and a polystyrene-equivalent number average molecular weight of 1×10 ³ to 1×10 ⁸ .
The polymer compound may be a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or other forms.
The terminal group of the polymer compound is preferably a stable group, because if the polymerization active group remains as it is, the luminescent property or luminance life may decrease when the polymer compound is used in the production of a light-emitting device. is. This terminal group includes, for example, a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.

A "low-molecular weight compound" means a compound having no molecular weight distribution and a molecular weight of 1×10 ⁴ or less.

A "structural unit" means a unit that exists at least one in a polymer compound.

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

An "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 number of carbon atoms in the aryl group is usually 6-60, preferably 6-20, more preferably 6-10, not including the number of carbon atoms in the substituents.
The aryl group may have a substituent, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2 -pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups includes groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

An "alkoxy group" may be either linear or branched. The straight-chain alkoxy group usually has 1 to 40 carbon atoms, preferably 4 to 10 carbon atoms, not including the carbon atoms of the substituents. The number of carbon atoms in the branched alkoxy group is usually 3-40, preferably 4-10, not including the number of carbon atoms in the substituents.
The alkoxy group may have a substituent group, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and hydrogen atoms in these groups are cycloalkyl groups, alkoxy groups, A cycloalkoxy group, an aryl group, a group substituted with a fluorine atom or the like can be mentioned.
The number of carbon atoms in the "cycloalkoxy group" is usually 3-40, preferably 4-10, not including the number of carbon atoms in the substituents.
A cycloalkoxy group may have a substituent, such as a cyclohexyloxy group.

The number of carbon atoms in the "aryloxy group" is usually 6-60, preferably 6-48, not including the number of carbon atoms in the substituents.
The aryloxy group may have a substituent, for example, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Pyrenyloxy groups and groups in which hydrogen atoms in these groups are substituted with alkyl groups, cycloalkyl groups, alkoxy groups, cycloalkoxy groups, fluorine atoms and the like are included.

A "p-valent heterocyclic group" (p represents an integer of 1 or more) refers to, from a heterocyclic compound, p hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring. means the remaining atomic groups excluding the hydrogen atoms of Among p-valent heterocyclic groups, it is an atomic group remaining after removing p hydrogen atoms among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A "p-valent aromatic heterocyclic group" is preferred.
“Aromatic heterocyclic compounds” include heterocyclic compounds such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, and dibenzophosphole. Compounds in which the ring itself exhibits aromaticity, and heterocyclic rings such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilole, and benzopyran that do not themselves exhibit aromaticity, and aromatic hydrocarbon rings are condensed with heterocyclic rings. means a compound containing

The number of carbon atoms in the monovalent heterocyclic group is usually 2-60, preferably 4-20, not including the number of carbon atoms in the substituents.
The monovalent heterocyclic group may have a substituent, for example, thienyl group, pyrrolyl group, furyl group, pyridinyl group, piperidinyl group, quinolinyl group, isoquinolinyl group, pyrimidinyl group, triazinyl group, and these and a group in which a hydrogen atom in the group is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or the like.

A "halogen atom" means a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

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

An "arylene group" means an atomic group remaining after removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon. The number of carbon atoms in the arylene group is generally 6-60, preferably 6-30, more preferably 6-18, not including the number of carbon atoms in the substituents.
The arylene group may have a substituent, for example, a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a naphthenediyl group, a fluorenediyl group, a pyrenediyl group, a perylenediyl group, Examples include chrysenediyl groups and groups having substituents on these groups, preferably groups represented by formulas (A-1) to (A-20). The arylene group includes groups in which multiple of these groups are bonded.

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

[In the formula, R and R ^a each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. Multiple 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 number of carbon atoms in the divalent heterocyclic group is usually 2-60, preferably 3-20, more preferably 4-15, not including the number of carbon atoms in the substituents.
The divalent heterocyclic group may have a substituent, such as pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilole, phenoxazine, phenothiazine, acridine, dihydroacridine, furan, thiophene, azole, diazole, and triazole, preferably a divalent group excluding two hydrogen atoms among the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring. is a group represented by formulas (AA-1) to (AA-34). Divalent heterocyclic groups include groups in which multiple of these groups are bonded.

［式中、Ｒ及びＲ^aは、前記と同じ意味を表す。］

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

The "crosslinking group" is a group capable of forming a new bond by subjecting it to heating, ultraviolet irradiation, near-ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc., preferably a cross-linking group. It is a cross-linking group represented by Formulas (XL-1) to (XL-17) of Group A.

A "substituent" represents a halogen atom, a cyano group, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, an amino group, or a substituted amino group.

<Light emitting element>
A light-emitting device of the present invention is a light-emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode. hand,
the first organic layer is a layer containing a polymer compound (TP),
the second organic layer is a layer containing a crosslinked body of a crosslinkable material,
The polymer compound (TP) has an absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state (hereinafter also referred to as “ΔE _ST ”) of 0.5 eV or less. a structural unit (hereinafter also referred to as “structural unit (C)”) containing a group obtained by removing one or more hydrogen atoms from the low-molecular compound (T),
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from Group A, or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from Group A. The above light-emitting device.

Methods for forming the first organic layer and the second organic layer include, for example, a dry method such as a vacuum deposition method, and a wet method such as a spin coating method and an inkjet method, with the wet method being preferred.

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

When the second organic layer is formed by a wet method, it is preferable to use the second ink described later. After forming the second organic layer, the cross-linking material contained in the second organic layer can be cross-linked by heating or irradiating with light, and the cross-linking material contained in the second organic layer can be cross-linked by heating. It is preferred to crosslink the material. When the cross-linking material is contained in the second organic layer in a cross-linked state (a cross-linked body of the cross-linking material), the second organic layer is substantially insoluble in the solvent. Therefore, the second organic layer can be suitably used for stacking light-emitting elements.

The heating temperature for crosslinking is usually 25°C to 300°C, preferably 50°C to 260°C, more preferably 130°C to 230°C, still more preferably 180°C to 210°C. .
The heating time is usually 0.1 to 1000 minutes.

Types of light used for light irradiation are, for example, ultraviolet light, near-ultraviolet light, and visible light.

Methods for analyzing the components contained in the first organic layer or the second organic layer include, for example, chemical separation analysis methods such as extraction, infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), Instrumental analysis methods such as mass spectrometry (MS), and analytical methods combining chemical separation analysis methods and instrumental analysis methods are included.

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

<First organic layer>
The polymer compound ( _TP ) contained in the first organic layer is a structural unit (C )including.
The low-molecular-weight compound (T) is preferably a thermally activated delayed fluorescence (TADF) material.

ΔE _ST of the low-molecular-weight compound (T) is preferably 0.0001 eV or more and 0.45 eV or less, more preferably 0.001 eV or more and 0.20 eV or less, because the light-emitting device of the present invention has excellent external quantum efficiency. and more preferably 0.01 eV or more and 0.11 eV or less.

The oscillator strength of the low-molecular-weight compound (T) is preferably 0.005 or more and 1 or less, more preferably 0.01 or more and 0.3 or less, because the external quantum efficiency of the light-emitting device of the present invention is excellent.

Gaussian09, which is a quantum chemical calculation program, can be used to calculate ΔE _ST and oscillator strength of a compound. For example, after structural optimization of the ground state of a compound using the B3LYP-level density functional theory, ΔE _ST and oscillator strength can be calculated using the B3LYP-level time-dependent density functional theory. . As a basis function, 6-31G* is usually used, but if the compound contains an atom that cannot use 6-31G*, LANL2DZ can be used for that atom.

The low-molecular-weight compound (T) is preferably a low-molecular-weight compound represented by formula (T-1), since the light-emitting device of the present invention has excellent external quantum efficiency.

n ^T1 is preferably 1 or 2, more preferably 1, because the light-emitting device of the present invention has excellent external quantum efficiency.

n ^T2 is preferably an integer of 1 or more and 3 or less, more preferably 1, because the light emitting device of the present invention has excellent external quantum efficiency.

The monovalent heterocyclic group represented by Ar ^T1 includes, for example, a monovalent heterocyclic group other than the below-described monovalent donor-type heterocyclic group and the below-described monovalent donor-type heterocyclic group, A carbazolyl group, a 1,2,3,4-tetrahydrocarbazolyl group, a dibenzofuryl group or a dibenzothienyl group is preferred, and a carbazolyl group is more preferred. good too.

In the substituted amino group represented by Ar ^T1 , the substituent of the amino group is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group. It may have a substituent. Examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituents of the amino group are the examples and preferred ranges of the aryl group and monovalent heterocyclic group in the substituents Ar ^T1 may have later. Same as range.

A "nitrogen atom having no double bonds" means a nitrogen atom having only single bonds between the nitrogen atom and all atoms bonded to the nitrogen atom.
The phrase "containing a nitrogen atom having no double bond in the ring" means -N(-R ^N )- (wherein R ^N represents a hydrogen atom or a substituent), or the formula:

で表される基を環内に含むことを意味する。

It means that the group represented by is included in the ring.

a group containing a nitrogen atom having no double bond in the ring and represented by =N-, a boron atom, a group represented by -C(=Z ^T1 )-, -S(=O)- a group represented by —S(=O) ₂ — and a monovalent heterocyclic group (hereinafter referred to as “1 Also referred to as a "valence donor-type heterocyclic group".), the number of nitrogen atoms having no double bond constituting the ring is usually 1-10.

The number of carbon atoms in the monovalent donor-type heterocyclic group is usually 2 to 60 not including the number of carbon atoms in the substituents.

Examples of monovalent donor-type heterocyclic groups include pyrrolyl, indolyl, isoindolyl, carbazolyl, 1,2,3,4-tetrahydrocarbazolyl, 9,10-dihydroacridinyl, 5 ,10-dihydrophenazinyl group, acridonyl group, phenoxazinyl group or phenothiazinyl group, preferably pyrrolyl group, indolyl group, carbazolyl group, 1,2,3,4-tetrahydrocarbazolyl group, 9, 10-dihydroacridinyl group, phenoxazinyl group or phenothiazinyl group, and these groups may have a substituent.

The number of carbon atoms in the monovalent heterocyclic group other than the monovalent donor-type heterocyclic group is usually 2 to 60, not including the number of carbon atoms in the substituent.

Examples of monovalent heterocyclic groups other than monovalent donor-type heterocyclic groups include diazolyl, triazolyl, furyl, thienyl, oxadiazolyl, thiadiazolyl, pyridinyl, diazaphenyl, triazinyl, and azanaphthyl groups. , diazanaphthyl group, triazanaphthyl group, azaanthracenyl group, diazaanthracenyl group, triazaanthracenyl group, azaphenanthrenyl group, diazaphenanthrenyl group, triazaphenanthrenyl group, dibenzofuryl group, dibenzothienyl group, dibenzosilyl group, azacarbazolyl group and diazacarbazolyl group, and these groups may have a substituent.

The monovalent donor-type heterocyclic group and the monovalent heterocyclic group other than the donor-type heterocyclic group are preferably groups in which one hydrogen atom directly bonded to a heteroatom constituting the heterocyclic ring is removed.

The substituents Ar ^T1 may have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom, or a cyano is preferred, an alkyl group, an aryl group, a substituted amino group or a monovalent heterocyclic group is more preferred, an aryl group or a monovalent heterocyclic group is even more preferred, and these groups may further have a substituent good.

Examples of the aryl group which is a substituent that Ar ^T1 may have include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a naphthacenyl group, a fluorenyl group, a spirobifluorenyl group, an indenyl group, and a pyrenyl group. , a perylenyl group, a chrysenyl group, or a group in which these groups are condensed, preferably a phenyl group, and these groups may have a substituent.

Examples and preferred ranges of the monovalent heterocyclic group and the substituted amino group, which are the substituents that Ar ^T1 may have, are the examples of the monovalent heterocyclic group and the substituted amino group represented by Ar ^T1 , respectively. and the same as the preferred range.

Ar ^T1 preferably has a monovalent heterocyclic group as a substituent because the light-emitting device of the present invention has excellent external quantum efficiency.

Preferred substituents that the substituent Ar ^T1 may further have include an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, and a monovalent A heterocyclic group, a substituted amino group, a halogen atom or a cyano group, more preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, still more preferably an alkyl group or an aryl group, and these groups may further have a substituent.

Examples and preferred ranges of the aryl group, the monovalent heterocyclic group and the substituted amino group, which are the substituents which the substituents which Ar ^T1 may further have, are those which Ar ^T1 has The examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group, which are optional substituents, are the same.

At least one of Ar ^T1 is preferably a group represented by formula (T1-1) described later, since the light-emitting device of the present invention has excellent external quantum efficiency, and these groups have a substituent. may

Ar ^T1 is preferably a monovalent donor-type heterocyclic group, more preferably a group represented by formula (T1-1) described later, since the light-emitting device of the present invention has excellent external quantum efficiency. , these groups may have a substituent.

When multiple Ar ^T1 are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring.

The "divalent group" includes, for example, an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^ArT1 )-, a group represented by -B(R ^ArT1 )- a group represented by -P(R ^ArT1 )-, a group represented by -(O=)P(R ^ArT1 )-, a group represented by -Si(R ^ArT1 ') ₂ -, - A group represented by S(=O)-, a group represented by -S(=O) ₂ , a group represented by -C(=Z ^T1 )-, an oxygen atom or a sulfur atom, and these The group may have a substituent.

R ^ArT1 and R ^ArT1 ' each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or It represents a cyano group, and these groups may have a substituent.

Examples and preferred ranges of the divalent alkylene group and cycloalkylene group are the same as the examples and preferred range of the alkylene group and cycloalkylene group represented by L ^A described below.

Examples and preferred ranges of the divalent arylene group and divalent heterocyclic group are the same as the examples and preferred range of the arylene group and divalent heterocyclic group represented by L ^T1 described later.

Examples and preferred ranges of R ^ArT1 and R ^ArT1 ' are the same as examples and preferred ranges of R ^XT1 and R ^XT1 ', respectively, described later.

Examples and preferred ranges of the substituent that the divalent group may have and the substituent that the substituent may further have are the substituent that Ar ^T1 may have and the substituent that the substituent may have It is the same as the examples and preferred range of the substituent which may be further contained.

・Group represented by formula (T1-1)

［式中、
環Ｒ^T1及び環Ｒ^T2は、それぞれ独立に、－Ｃ（＝Ｚ^T1）－で表される基を環内に含まない芳香族炭化水素環、又は、＝Ｎ－で表される基、ホウ素原子、－Ｃ（＝Ｚ^T1）－で表される基、－Ｓ（＝Ｏ）－で表される基、－Ｓ（＝Ｏ）₂－で表される基、及び、前記式（Ｐ）で表される基を環内に含まない複素環を表し、これらの環は置換基を有していてもよい。Ｚ^T1は前記と同じ意味を表す。
Ｘ^T1は、単結合、酸素原子、硫黄原子、－Ｎ(Ｒ^XT1)－で表される基、又は、－Ｃ(Ｒ^XT1')₂－で表される基を表す。Ｒ^XT1及びＲ^XT1'は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^XT1'は、同一でも異なっていてもよい。］

[In the formula,
Ring R ^T1 and ring R ^T2 are each independently an aromatic hydrocarbon ring that does not contain a group represented by -C(=Z ^T1 )- in the ring, or a group represented by =N-, boron an atom, a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, and the formula (P) represents a heterocyclic ring that does not contain a group represented by in the ring, and these rings may have a substituent. Z ^T1 has the same meaning as above.
X ^T1 represents a single bond, an oxygen atom, a sulfur atom, a group represented by -N(R ^XT1 )-, or a group represented by -C(R ^XT1 ') ₂ -. R ^XT1 and R ^XT1 ' each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or It represents a cyano group, and these groups may have a substituent. Multiple R ^XT1 ' may be the same or different. ]

The number of carbon atoms in the "aromatic hydrocarbon ring not containing a group represented by -C(=Z ^T1 )-" is usually 6 to 60, not including the number of carbon atoms in the substituents, Preferably 6-18.

Examples of the aromatic hydrocarbon ring containing no group represented by -C(=Z ^T1 )- in the ring include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, naphthacene ring, pyrene ring, perylene ring, A chrysene ring and a ring in which these rings are condensed are included, preferably a benzene ring, and these rings may have a substituent.

"Group represented by =N-, boron atom, group represented by -C (=Z ^T1 )-, group represented by -S (=O)-, represented by -S (=O) ₂ - and the heterocyclic ring which does not contain a group represented by the above formula (P) in its ring” usually has 2 to 60 carbon atoms, not including the carbon atoms of the substituents.

a group represented by =N-, a boron atom, a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ - and the heterocyclic ring that does not contain a group represented by the formula (P) in the ring include, for example, pyrrole ring, furan ring, thiophene ring, silole ring, and phosphole ring, and these rings may have a substituent.

Since the external quantum efficiency of the light-emitting device of the present invention is excellent, the ring R ^T1 has a monovalent heterocyclic group or a substituted amino group as a substituent, or the ring R ^T2 has a monovalent heterocyclic group or a substituted amino group as a substituent. It is preferable to have a substituted amino group, more preferably the ring R ^T1 has a monovalent heterocyclic group as a substituent, or the ring R ^T2 has a monovalent heterocyclic group as a substituent, and the ring R More preferably, only one of ^T1 and ring R ^T2 has a monovalent heterocyclic group as a substituent.

Examples and preferred ranges of the substituents that ring R ^T1 and ring R ^T2 may have and the substituents that these substituents may further have are the substituents that Ar ^T1 may have and the It is the same as the example and preferred range of the substituent that the substituent may further have.

At least one of ring R ^T1 and ring R ^T2 is preferably an aromatic hydrocarbon ring that does not contain a group represented by -C(=Z ^T1 )- in the ring, and is a benzene ring. is more preferable, and these rings may have a substituent.

Both ring R ^T1 and ring R ^T2 are preferably aromatic hydrocarbon rings not containing a group represented by —C(=Z ^T1 )—, more preferably benzene rings. ring may have a substituent.

X ^T1 is preferably a single bond, an oxygen atom or a group represented by -C(R ^XT1 ') ₂ -, more preferably a single bond.

R ^XT1 is preferably an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may have a substituent.

R ^XT1 ' is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

A plurality of R ^XT1 ' 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.

Examples and preferred ranges of the aryl group, ^monovalent heterocyclic group and substituted amino group represented by R ^XT1 and R ^XT1 ' are, respectively, the aryl group and the monovalent are the same as the examples and preferred ranges of the heterocyclic group and the substituted amino group.

Examples and preferred ranges of substituents that R ^XT1 and R ^XT1 ' may have are the same as examples and preferred ranges of substituents that Ar ^T1 may further have. is.

The group represented by formula (T1-1) is preferably a group represented by formula (T1-1A).

［式中、
Ｘ^T1は、前記と同じ意味を表す。
Ｒ^T1、Ｒ^T2、Ｒ^T3、Ｒ^T4、Ｒ^T5、Ｒ^T6、Ｒ^T7及びＲ^T8は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基を表し、これらの基は置換基を有していてもよい。］

[In the formula,
X ^T1 has the same meaning as above.
R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 , R ^T7 and R ^T8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryl It represents an oxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may have a substituent. ]

R ^T1 to R ^T8 are preferably a hydrogen atom, an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, and these groups may further have a substituent.

R ^T1 , R ^T2 , R ^T4 , R ^T5 , R ^T7 and R ^T8 are preferably hydrogen atoms or alkyl groups, more preferably hydrogen atoms, and these groups further have substituents. may

At least one of R ^T3 and R ^T6 is preferably an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group, since the light-emitting device of the present invention has excellent external quantum efficiency. , a monovalent heterocyclic group or a substituted amino group, more preferably a monovalent heterocyclic group, and these groups may further have a substituent.

Since the external quantum efficiency of the light-emitting device of the present invention is excellent, only one of R ^T3 and R ^T6 is preferably an alkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group. It is more preferably a monovalent heterocyclic group or a substituted amino group, more preferably a monovalent heterocyclic group, and these groups may further have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by R ^T1 to R ^T8 are, respectively, the aryl group and the monovalent heterocyclic group in the substituents Ar ^T1 may have. It is the same as the examples and preferred ranges of the cyclic group and the substituted amino group.

Examples and preferred ranges of substituents that R ^T1 to R ^T8 may have are the same as examples and preferred ranges of substituents that Ar ^T1 may further have. be.

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

The arylene group represented by L ^T1 is preferably a phenylene group, a naphthalene diyl group, a fluorenediyl group, a phenanthenediyl group or a dihydrophenanthenediyl group, and more preferably a group of formulas (A-1) to ( It is a group represented by A-3), more preferably a group represented by formula (A-1), and these groups may have a substituent.

The divalent heterocyclic group represented by L ^T1 is preferably a group represented by formulas (AA-1) to (AA-34).

Examples and preferred ranges of the substituent that L ^T1 may have and the substituent that the substituent may further have are, respectively, the substituent that Ar ^T1 may have and the substituent that the substituent may have It is the same as the examples and preferred range of the substituent which may be further contained.

R ^T1 ' is preferably an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituent represented by R ^T1 ' are, respectively, ^the aryl group, monovalent heterocyclic group and It is the same as the example and preferred range of the substituent.

Ar ^T2 is preferably a boron atom, a group represented by —C(=Z ^T1 )—, a group represented by —S(=O) ₂ , or A group represented by the formula (P), an aromatic hydrocarbon group having an electron-withdrawing group, a heterocyclic group containing a boron atom in the ring, or a group represented by =N- in the ring A heterocyclic group, more preferably a heterocyclic group containing a boron atom in the ring, or a heterocyclic group containing a group represented by =N- in the ring, more preferably represented by =N- is a heterocyclic group containing a group in the ring, and these groups may have a substituent.

Z ^T1 is preferably an oxygen atom.
R ^ZT1 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituent represented by R ^ZT1 are the aryl group, monovalent heterocyclic group and substituent in the substituent Ar ^T1 may have, respectively. It is the same as the example and preferred range of the group.

In the aromatic hydrocarbon group having an electron-withdrawing group, the number of carbon atoms in the aromatic hydrocarbon group is usually 6 to 60, preferably 6 to 18, not including the number of carbon atoms in the substituents. .

Examples of the aromatic hydrocarbon group in the aromatic hydrocarbon group having an electron-withdrawing group include benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, dihydrophenanthrene ring, naphthacene ring, fluorene ring, spirobifluorene ring, Indene ring, pyrene ring, perylene ring, chrysene ring, and a group formed by removing some or all of the hydrogen atoms from the ring formed by direct bonding of these rings, preferably part or all of the benzene ring These groups may have a substituent.

The electron-withdrawing group includes, for example, an alkyl group having a fluorine atom as a substituent, a fluorine atom, a cyano group and a nitro group.

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

In the aromatic hydrocarbon group having an electron-withdrawing group, the number of electron-withdrawing groups possessed by the aromatic hydrocarbon group is usually 1 to 10, preferably 1 or 2.

In the heterocyclic group containing a boron atom in the ring, the number of carbon atoms constituting the ring is usually 1-60, preferably 12-18.

Heterocyclic groups containing a boron atom in the ring include, for example, borole ring, benzoborole ring, dibenzoborole ring group, borine ring, benzoborine ring, dibenzoborine ring, phenazaborine ring, phenoxaborine ring, phenothiaborine ring, phenoselena Borine ring, formula (DB):

で表される環、又は、これらの環が縮合してなる環から一部又は全部の水素原子を除いてなる基が挙げられ、好ましくは、フェナザボリン環又は式（ＤＢ）で表される環から一部又は全部の水素原子を除いてなる基であり、これらの基は置換基を有していてもよい。

or a group obtained by removing some or all of the hydrogen atoms from a ring formed by condensing these rings, preferably a phenazaborine ring or a ring represented by the formula (DB) It is a group from which some or all hydrogen atoms are removed, and these groups may have a substituent.

In the heterocyclic group containing a group represented by =N- in the ring, the number of nitrogen atoms having double bonds constituting the ring is usually 1 to 10, preferably 3.

In the heterocyclic group containing a group represented by =N- in the ring, the number of carbon atoms constituting the ring is usually 1-60, preferably 3-5.

Examples of the heterocyclic group containing a group represented by =N- in the ring include diazole ring, triazole ring, oxadiazole ring, thiadiazole ring, thiazole ring, oxazole ring, isothiazole ring, isoxazole ring, benzo diazole ring, benzotriazole ring, benzoxadiazole ring, benzothiadiazole ring, benzothiazole ring, benzoxazole ring, azacarbazole ring, diazacarbazole ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, acridine ring, benzoquinoline ring, phenanthroline ring, or a group obtained by removing some or all of the hydrogen atoms from a ring formed by condensing these rings, preferably a pyridine ring, A group obtained by removing some or all of hydrogen atoms from a pyrimidine ring or a triazine ring, and these groups may have a substituent.

Ar ^T2 has at least one group represented by formula (1T′) as a substituent.

［式中、Ｌ^T1、ｎ^T1及びＡｒ^T1は、前記と同じ意味を表す。］

[In the formula, L ^T1 , n ^T1 and Ar ^T1 have the same meanings as described above. ]

Ar ^T2 may have n ^T3 groups represented by formula (DC) as substituents, and preferably has at least one group represented by formula (DC).

n ^T3 represents an integer of 0 or more and 15 or less, preferably 0 or more and 5 or less, more preferably 1 or 2;

［式中、
ｍ^DA1は、０以上１０以下の整数を表す。
Ａｒ^DA1は、置換基を有していてもよいアリーレン基を表す。Ａｒ^DA1が複数存在する場合、それらは同一でも異なっていてもよい。
Ｔ^DAは、置換基を有していてもよいアリール基を表す。］

[In the formula,
^mDA1 represents an integer of 0 or more and 10 or less.
Ar ^DA1 represents an optionally substituted arylene group. When multiple Ar ^DA1 are present, they may be the same or different.
^TDA represents an optionally substituted aryl group. ]

^mDA1 is preferably 0 or 1, more preferably 0.

Ar ^DA1 is preferably a phenylene group or a fluorenediyl group, more preferably groups represented by formulas (ArDA-1) to (ArDA-4), and these groups have substituents. may When multiple Ar ^DA1 are present, they are preferably the same.

［式中、
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又はアリール基を表し、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。
Ｒ^DBは、水素原子、アルキル基、シクロアルキル基又はアリール基を表し、これらの基は置換基を有していてもよい。Ｒ^DBが複数ある場合、それらは同一でも異なっていてもよい。］

[In the formula,
^RDA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may further have a substituent. When there are multiple ^RDAs , they may be the same or different.
^RDB represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. When there are multiple ^RDBs , 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 substituents. may

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

The substituent that Ar ^DA1 may have is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, more preferably an alkyl group or a cycloalkyl group. The group may have a substituent.

^TDA is preferably a group represented by formula (TDA-1) or formula (TDA-2), more preferably a group represented by formula (TDA-1).

［式中、Ｒ^DA及びＲ^DBは、前記と同じ意味を表す。］

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

The group represented by formula (D-C) is preferably a group represented by formulas (D-C1) to (D-C4), more preferably a group represented by formula (D-C1). .

［式中、
Ｒ^p4、Ｒ^p5及びＲ^p6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し、これらの基は置換基を有していてもよい。Ｒ^p4、Ｒ^p5及びＲ^p6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。
ｎｐ４は、０～４の整数を表す。
ｎｐ５及びｎｐ６は、それぞれ独立に、は０～５の整数を表す。］

[In the formula,
R ^p4 , R ^p5 and R ^p6 each independently represent an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom, and these groups may have a substituent. When multiple R ^p4 , R ^p5 and R ^p6 are present, they may be the same or different.
np4 represents an integer of 0-4.
np5 and np6 each independently represent an integer of 0 to 5; ]

np4 is preferably an integer from 0 to 2, more preferably 0. np5 is preferably an integer from 0 to 3, more preferably 0. np6 is preferably an integer from 0 to 2, more preferably 0.

R ^p4 to R ^p6 are preferably an optionally substituted alkyl group, more preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group or It is a tert-octyl group.

The substituent that Ar ^T2 may have (which is different from the group represented by formula (1T′) and the group represented by formula (DC); the same shall apply hereinafter) includes an alkyl group, cyclo An alkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom or a cyano group is preferable, an alkyl group or a cycloalkyl group is more preferable, and these groups may have a substituent.

Examples and preferred ranges of the substituents which the substituents which Ar ^T2 may further have are those of the substituents which the substituents which Ar ^T1 may further have Same as examples and preferred ranges.

In the compound represented by formula (T-1), when Ar ^T2 is a heterocyclic group containing a group represented by =N- in the ring, the compound represented by formula (T-1) is the present Since the external quantum efficiency of the light-emitting device of the invention is excellent, compounds represented by formulas (T'-1) to (T'-14) described later are preferable, and more preferably formula (T'-4 ) is a compound represented by

In the compound represented by formula (T-1), when Ar ^T2 is an aromatic hydrocarbon group having an electron-withdrawing group, the compound represented by formula (T-1) is the light-emitting device of the present invention. Since the external quantum efficiency of is excellent, it is preferably a compound represented by the following formula (T'-15) to formula (T'-18), more preferably a compound represented by formula (T'-15) It is a compound that

In the compound represented by the formula (T-1), Ar ^T2 is a boron atom, a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, -S(= O) In the case of a group represented by _2- or a group represented by the above formula (P), the compound represented by the formula (T-1) is excellent in external quantum efficiency of the light-emitting device of the present invention. Compounds represented by formulas (T'-19) to (T'-22) described below are preferred, and compounds represented by formula (T'-21) are more preferred.

In the compound represented by formula (T-1), when Ar ^T2 is a heterocyclic group containing a boron atom in the ring, the compound represented by formula (T-1) is external to the light-emitting device of the present invention. Since the quantum efficiency is excellent, it is preferably a compound represented by the following formula (T'-23) or (T'-24), more preferably a compound represented by the formula (T'-24) is.

The compound represented by formula (T-1) has excellent external quantum efficiency of the light-emitting device of the present invention, and therefore is preferably represented by formulas (T'-1) to (T'-4), formula (T'- 12) ~ formula (T'-14), formula (T'-15), formula (T'-17), formula (T'-18), formula (T'-20), formula (T'-21) , a compound represented by formula (T'-23) or formula (T'-24), more preferably a compound represented by formula (T'-4) or formula (T'-24), More preferred is a compound represented by formula (T'-4).

［式中、
Ｒ^1T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、ハロゲン原子、シアノ基、式（１T’）で表される基又は式（D-C）で表される基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^1Tは、同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。但し、複数存在するＲ^1Tのうち、少なくとも１個は式（１T’）で表される基である。
Ｒ^1T'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、電子求引性基、式（１T’）で表される基又は式（D-C）で表される基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^1T'は、同一でも異なっていてもよく、直接結合して、又は、２価の基を介して結合して、環を形成してもよい。但し、複数存在するＲ^1T'のうち、少なくとも１個は式（１T’）で表される基であり、且つ、少なくとも１個は電子求引性基である。］

[In the formula,
R ^1T represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom, a cyano group, a group represented by the formula (1T'), or a group represented by the formula (DC); These groups may have a substituent. A plurality of R ^1T may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. However, at least one of the plurality of R ^1T is a group represented by the formula (1T').
R ^1T ' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron-withdrawing group, a group represented by formula (1T'), or a group represented by formula (DC); , these groups may have a substituent. A plurality of R ^1T ' may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring. However, among a plurality of R ^1T ', at least one is a group represented by formula (1T') and at least one is an electron-withdrawing group. ]

Of the plurality of R ^1T and R ^1T ', each of n ^T3 is preferably a group represented by formula (DC), and at least one is a group represented by formula (DC). more preferred.

Of the plurality of R ^1T 's, 1 to 5 are preferably electron-withdrawing groups, and 1 or 2 are more preferably electron-withdrawing groups.

R ^1T is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, a cyano group, a group represented by the formula (1T') or a group represented by the formula (DC) and more preferably a hydrogen atom, a group represented by formula (1T′) or a group represented by formula (DC), and these groups may have a substituent.

R ^1T ' is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an electron-withdrawing group, a group represented by formula (1T'), or represented by formula (DC) group, more preferably a hydrogen atom, an electron-withdrawing group, a group represented by formula (1T') or a group represented by formula (DC), and these groups have a substituent may

When R ^1T and R ^1T ' are not respectively a group represented by formula (1T') or a group represented by formula (DC), the substituents R ^1T and R ^1T ' may have Examples and preferred ranges are the same as the examples and preferred ranges of the substituents that Ar ^T2 may further have.

Examples of low-molecular-weight compounds (T) include compounds represented by the following formulas.

［式中、
Ｚ¹は、－Ｎ＝で表される基、又は、－ＣＨ＝で表される基を表す。
Ｚ²は、酸素原子又は硫黄原子を表す。
複数存在するＺ¹及びＺ²は、各々、同一でも異なっていてもよい。］

[In the formula,
Z ¹ represents a group represented by -N= or a group represented by -CH=.
^Z2 represents an oxygen atom or a sulfur atom.
A plurality of Z ¹ and Z ² may be the same or different. ]

Z ¹ is preferably a group represented by -N=. Z ² is preferably an oxygen atom.

Low molecular compounds (T) are available from Aldrich, Luminescence Technology Corp. and the like. In addition, for example, WO 2007/063754, WO 2008/056746, WO 2011/032686, WO 2012/096263, JP 2009-227663, JP 2010- No. 275255, Advanced Materials, Vol. 26, pp. 7931-7958, 2014, can be synthesized according to the method described.

[Polymer compound (TP)]
In the first organic layer, one type of polymer compound (TP) may be contained alone, or two or more types may be contained.

The structural unit (C) contained in the polymer compound (TP) is preferably a low-molecular compound because the light-emitting device of the present invention has excellent external quantum efficiency and the polymer compound (TP) can be easily produced. A structural unit containing a group obtained by removing 1 or more and 5 or less hydrogen atoms from (T), more preferably a structural unit represented by formulas (1C) to (4C), still more preferably It is a structural unit represented by formula (3C).

Structural unit represented by formula (1C) Examples and preferred ranges of the arylene group and the divalent heterocyclic group represented by L ^C are respectively the arylene group and the divalent heterocyclic group represented by Ar ^Y1 described later. It is the same as the example and preferred range of the cyclic group.

L ^C is preferably an oxygen atom, -C(R ^B ) ₂ - or an arylene group.

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

n ^c1 is preferably an integer of 1 or more and 4 or less.

Structural Units Represented by Formula (2C) Examples and preferred ranges of the arylene group and divalent heterocyclic group represented by L ^d and L ^e are respectively the arylene group represented by Ar ^Y1 and 2 It is the same as the example and preferred range of the valent heterocyclic group.

L ^d and L ^e are preferably an oxygen atom, —C(R ^B ) ₂ — or an arylene group, more preferably an arylene group.

n ^d1 is preferably 0 because the light emitting device of the present invention has excellent external quantum efficiency.

n ^e1 is preferably an integer of 1 or more and 4 or less.

Ar ^1M is a benzene ring, naphthalene ring, fluorene ring, phenanthrene ring, dihydrophenanthrene ring, pyridine ring, diazabenzene ring, triazine ring, carbazole ring, phenoxazine ring or phenothiazine ring to carbon atoms or hetero atoms constituting the ring; A group having three directly bonded hydrogen atoms removed is preferable, and these groups may have a substituent.

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

· The structural unit T ^2C represented by formula (3C) is preferably a group represented by formula (T-2C-1) to formula (T-2C-5), and formula (T-2C-2 ) or a group represented by formula (T-2C-5), more preferably a group represented by formula (T-2C-2).

［式中、
ｍ^DA1、ｎ^T1、ｎ^T2、ｎ^T3、Ａｒ^DA1、Ａｒ^T1、Ｌ^T1及びＴ^DAは前記と同じ意味を表す。ｍ^DA1、ｎ^T1、Ａｒ^DA1、Ａｒ^T1、Ｌ^T1及びＴ^DA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。
Ａｒ^T2'は、Ａｒ^T2から１個の水素原子を除いてなる基を表す。
Ａｒ^T2''は、Ａｒ^T2から２個の水素原子を除いてなる基を表す。
Ａｒ^T3は、－Ｃ（＝Ｚ^T1）－で表される基、－Ｓ（＝Ｏ）－で表される基、－Ｓ（＝Ｏ）₂－で表される基、電子求引性基を有する芳香族炭化水素基、ホウ素原子を環内に含む複素環基、又は、＝Ｎ－で表される基を環内に含む複素環基であり、これらの基は置換基を有していてもよい。Ｚ^T1は前記と同じ意味を表す。
Ａｒ^T3'は、Ａｒ^T3で表される電子求引性基を有する芳香族炭化水素基、ホウ素原子を環内に含む複素環基、又は、＝Ｎ－で表される基を環内に含む複素環基から、１個の水素原子を除いてなる基を表す。
Ａｒ^L1は、Ｔ^DAから１個の水素原子を除いてなる基を表す。複数存在するＡｒ^L1は、同一でも異なっていてもよい。
Ａｒ^L2は、Ｔ^DAから２個の水素原子を除いてなる基を表す。
Ａｒ^K1は、Ａｒ^T1から１個の水素原子を除いてなる基を表す。複数存在するＡｒ^K1は、同一でも異なっていてもよい。
Ａｒ^K2は、Ａｒ^T1から２個の水素原子を除いてなる基を表す。］

[In the formula,
m ^DA1 , n ^T1 , n ^T2 , n ^T3 , Ar ^DA1 , Ar ^T1 , L ^T1 and T ^DA have the same meanings as above. When multiple m ^DA1 , n ^T1 , Ar ^DA1 , Ar ^T1 , L ^T1 and T ^DA are present, they may be the same or different.
Ar ^T2 ' represents a group obtained by removing one hydrogen atom from Ar ^T2 .
Ar ^T2 ″ represents a group obtained by removing two hydrogen atoms from Ar ^T2 .
Ar ^T3 is a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, an electron-withdrawing group , a heterocyclic group containing a boron atom in the ring, or a heterocyclic group containing a group represented by =N- in the ring, and these groups have a substituent may Z ^T1 has the same meaning as above.
Ar ^T3 ' contains an aromatic hydrocarbon group having an electron-withdrawing group represented by Ar ^T3 , a heterocyclic group containing a boron atom in the ring, or a group represented by =N- in the ring It represents a group obtained by removing one hydrogen atom from a heterocyclic group.
Ar ^L1 represents a group obtained by removing one hydrogen atom from ^TDA . A plurality of Ar ^L1 may be the same or different.
Ar ^L2 represents a group obtained by removing two hydrogen atoms from ^TDA .
Ar ^K1 represents a group obtained by removing one hydrogen atom from Ar ^T1 . A plurality of Ar ^K1 may be the same or different.
Ar ^K2 represents a group obtained by removing two hydrogen atoms from Ar ^T1 . ]

A group represented by -C(=Z ^T1 )- represented by Ar ^T3 , a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, an electron withdrawing Examples and preferred ranges of the aromatic hydrocarbon group having a polar group, the heterocyclic group containing a boron atom in the ring, and the heterocyclic group containing a group represented by =N- in the ring are Ar ^T2 A group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, an electron-withdrawing group is the same as the examples and preferred ranges of the aromatic hydrocarbon group having , the heterocyclic group containing a boron atom in the ring, and the heterocyclic group containing a group represented by =N- in the ring.

Examples and preferred ranges of m ^DA1 , n ^T1 , n ^T2 , n ^T3 , Ar ^DA1 and L ^T1 in formulas (T-2C-1) to (T-2C-5) are the low-molecular-weight compounds (T ) are similar to the examples and preferred ranges of m ^DA1 , n ^T1 , n ^T2 , n ^T3 , Ar ^DA1 and L ^T1 in ).

In formulas (T-2C-1) to (T-2C-5), when there are multiple m ^DA1 , n ^T1 , Ar ^DA1 , Ar ^T1 , L ^T1 and T ^DA , they are each the same. preferable.

· Structural unit represented by formula (4C) In the structural units represented by formulas (1C) to (4C), the groups represented by T ^1C , T ^2C and T ^3C are low-molecular compounds (T-1 ) is preferably a group obtained by removing one or more hydrogen atoms from Ar ^T1 , Ar ^T2 or T ^DA , more preferably a group obtained by removing one or more hydrogen atoms from Ar ^T1 or T ^DA A group obtained by removing one or more hydrogen atoms from ^TDA is more preferred.

The structural units represented by formula (3C) are preferably structural units represented by formulas (3C-1) to (3C-3).

［式中、
環Ｒ^T1、環Ｒ^T2、ｍ^DA1、ｎ^d1、ｎ^T1、Ａｒ^DA1、Ａｒ^L1、Ｌ^d、Ｌ^T1、Ｒ^1T及びＸ^T1は前記と同じ意味を表す。環Ｒ^T1、環Ｒ^T2、ｍ^DA1、ｎ^d1、ｎ^T1、Ａｒ^DA1、Ａｒ^L1、Ｌ^d、Ｌ^T1、Ｒ^1T及びＸ^T1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。
ｋは、０又は１を表す。ｋ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。
Ｚ³は、－Ｎ＝で表される基、－ＣＨ＝で表される基、又は－ＣＲ^1T＝で表される基を表す。複数存在するＺ³は、同一でも異なっていてもよい。但し、少なくとも１つのＺ³は、－Ｎ＝で表される基を表す。］

[In the formula,
Ring R ^T1 , ring R ^T2 , m ^DA1 , n ^d1 , n ^T1 , Ar ^DA1 , Ar ^L1 , L ^d , L ^T1 , R ^1T and X ^T1 have the same meanings as described above. When multiple rings R ^T1 , R ^T2 , m ^DA1 , n ^d1 , n ^T1 , Ar ^DA1 , Ar ^L1 , L ^d , L ^T1 , R ^1T and X ^T1 are present, they may be the same or different. .
k represents 0 or 1; When there are multiple k's, they may be the same or different.
Z ³ represents a group represented by -N=, a group represented by -CH=, or a group represented by -CR ^1T =. A plurality of Z ³ may be the same or different. However, at least one Z ³ represents a group represented by -N=. ]

In the structural unit represented by formula (3C-1), the definition, examples and preferred ranges of ring R ^T1 or ring R ^T2 are the same as the definition, examples and preferred ranges of ring R ^T1 or ring R ^T2 in the low-molecular-weight compound (T). Similar to range.

In the structural unit represented by formula (3C-2) or formula (3C-3), the definition, examples and preferred ranges of the moieties excluding -(L ^d )n ^d1 - possessed by ring R ^T1 or ring R ^T2 are , the definition, examples and preferred ranges of the ring R ^T1 or ring R ^T2 in the low-molecular-weight compound (T).

Examples and preferred ranges of m ^DA1 , n ^T1 , Ar ^DA1 , L ^T1 , R ^1T and X ^T1 in structural units represented by formulas (3C-1) to (3C-3) are low molecular compounds ( The same examples and preferred ranges for m ^DA1 , n ^T1 , Ar ^DA1 , L ^T1 , R ^1T and X ^T1 in T).

Examples and preferred ranges of n ^d1 and L ^d in the structural units represented by formulas (3C- ¹ ) to (3C-3) are respectively Same as examples and preferred ranges.

In structural units represented by formulas (3C-1) to (3C-3), ring R ^T1 , ring R ^T2 , m ^DA1 , n ^d1 , n ^T1 , Ar ^DA1 , Ar ^L1 , L ^d , L ^T1 , When there are multiple occurrences of R ^1T and X ^T1 , each of them is preferably the same.

Z ³ is preferably a group represented by -N=, and plural Z ³ are preferably the same.

k is preferably 1, and if there is more than one k, they are preferably the same.

Examples of structural units (C) include structural units represented by the following formulas.

［式中、
ｋ、ｎ^c1、ｎ^e1、Ｌ^c、Ｌ^e、Ｒ^1T、Ｒ^Y2、Ｚ¹、Ｚ²及びＺ³は前記と同じ意味を表す。
ｊは、０又は１を表す。ｊ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^TSは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基、ハロゲン原子又はシアノ基であり、これらの基は更に置換基を有していてもよい。複数存在するＲ^TSは、同一でも異なっていてもよい。］

[In the formula,
k, n ^c1 , n ^e1 , L ^c , L ^e , R ^1T , R ^Y2 , Z ¹ , Z ² and Z ³ have the same meanings as above.
j represents 0 or 1; When there are multiple j's, they may be the same or different.
R ^TS is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, a halogen atom or a cyano group, and these groups may further have a substituent. A plurality of R ^TS may be the same or different. ]

Preferably, j is 0, and if there are multiple j's, they are preferably the same.

R ^TS is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a monovalent heterocyclic group, a substituted amino group or a cyano group; A valent heterocyclic group is more preferred.

Examples and preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by ^{R TS} are, respectively, the aryl group, monovalent heterocyclic group and It is the same as the example and preferred range of the substituted amino group.

Examples and preferred ranges of the substituents that R ^TS may have are the same as the examples and preferred ranges of the substituents that the substituents that Ar ^T1 may further have, respectively. .

In the polymer compound (TP), the total amount of the structural units (C) is preferably from 0.01 to 0.01 with respect to the total amount of the structural units contained in the polymer compound (TP), because the external quantum efficiency of the present invention is excellent. It is 50 mol %, more preferably 0.1 to 30 mol %, still more preferably 1 to 20 mol %, particularly preferably 6 to 15 mol %.

The polymer compound (TP) preferably further contains a structural unit represented by the above formula (Y) because the light-emitting device of the present invention has excellent external quantum efficiency.

Ar ^Y1 is preferably represented by formula (A-1), formula (A-2), formula (A-6) - formula (A-10), formula (A-19) or formula (A-20) These groups may have a substituent.

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

The structural unit represented by formula (Y) is represented by formula (Y-1), formula (Y-2) or formula (Y-3) because the light-emitting device of the present invention has excellent external quantum efficiency. It is preferably a structural unit, more preferably a structural unit represented by formula (Y-1) or formula (Y-2), and preferably a structural unit represented by formula (Y-1). More preferred.

In formula (Y-1), R ^Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

The structural unit represented by formula (Y-1) is preferably a structural unit represented by 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又はアリール基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y11は、同一でも異なっていてもよい。］

[In the formula, R ^Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent. Multiple R ^Y11 may be the same or different. ]

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

In formula (Y-2), R ^Y2 is preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent.

In X ^Y1 , the combination of two R ^Y2 in the group represented by —C(R ^Y2 ) ₂ — is preferably both alkyl groups or cycloalkyl groups, both aryl groups, or one alkyl group Alternatively, it is a cycloalkyl group and the other is an aryl group, and these groups may have a substituent. Two R ^Y2 may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y2 forms a ring, the group represented by -C(R ^Y2 ) ₂ - is preferably a group represented by Formula (Y-A1)-Formula (Y-A5), and these groups may have a substituent.

In X ^Y1 , the combination of two R ^Y2 in the group represented by -C(R ^Y2 )=C(R ^Y2 )- is preferably both alkyl groups or cycloalkyl groups, or one of them is an alkyl group Alternatively, it is 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 optionally substituted alkyl groups or cycloalkyl groups 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, and when R ^Y2 forms a ring, -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ - The represented group is preferably a group represented by the formula (Y-B1)-(Y-B5), and these groups may have a substituent.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

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

The structural unit represented by formula (Y-2) is preferably a structural unit represented by formula (Y-2'), and is a structural unit represented by formula (Y-2''). is more preferred.

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

[In the formula, R ^Y1 and X ^Y1 have the same meanings as described above. ]

［式中、Ｒ^Y2及びＲ^Y11は前記と同じ意味を表す。］

[In the formula, R ^Y2 and R ^Y11 have the same meanings as described above. ]

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

［式中、Ｒ^Y11及びＸ^Y1は前記と同じ意味を表す。］

[In the formula, R ^Y11 and X ^Y1 have the same meanings as described above. ]

Examples of structural units represented by formula (Y) include structural units represented by formulas (Y-101) to (Y-108).

The total amount of structural units represented by formula (Y) is preferably 0.5 to 0.5 to 80 mol %, more preferably 30 to 60 mol %.

The polymer compound (TP) may further contain a structural unit represented by formula (X) described below. Examples and preferred ranges of structural units represented by the formula (X) that the polymer compound (TP) may contain are represented by the formula (X ) is the same as the example and preferred range of the structural unit represented by ).

In the polymer compound (TP), the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) may each contain one type or two or more types. good.

Constituent chains represented by formulas (S-1) to (S-3) The polymer compound (TP) is a constitutive chain represented by any one of formulas (S-1) to (S-3) and more preferably a structural chain represented by formula (S-2).

［式中、
Ａｒ^TWは、前記式(Y-1)～式(Y-3)で表される構成単位からなる群から選ばれる少なくとも１つの構成単位である。Ａｒ^TWが複数存在する場合、それらは同一でも異なっていてもよい。
Ｌ^S1は、前記式（１Ｃ）で表される構成単位である。
Ｌ^S2は、前記式（２Ｃ）で表される構成単位又は前記式（３Ｃ）で表される構成単位である。
Ｌ^S3は、前記式（４Ｃ）で表される構成単位である。］

[In the formula,
Ar ^TW is at least one structural unit selected from the group consisting of structural units represented by formulas (Y-1) to (Y-3). When multiple Ar ^TWs are present, they may be the same or different.
L ^S1 is a structural unit represented by the formula (1C).
L ^S2 is a structural unit represented by the formula (2C) or a structural unit represented by the formula (3C).
L ^S3 is a structural unit represented by the formula (4C). ]

In the constituent chains represented by formulas (S-1) to (S-3), when there are multiple Ar ^TWs , they may be the same or different, but are preferably the same. Examples and preferred ranges of Ar ^TW in formulas (S-1) to (S-3) are examples and preferred ranges of structural units represented by formulas (Y-1) to (Y-3) above, respectively. is the same as

Examples and preferred ranges of the structural unit represented by L ^S1 are respectively the same as examples and preferred ranges of the structural unit represented by formula (1C), and examples and preferred ranges of the structural unit represented by L ^S2 are the same as the examples and preferred ranges of the structural unit represented by formula (2C) and the structural unit represented by formula (3C), respectively, and the examples and preferred range of the structural unit represented by ^L are Each is the same as the example and preferred range of the structural unit represented by formula (4C).

In the structural chain represented by formula (S-2), the structural unit represented by L ^S2 is preferably a structural unit represented by formula (3C).

The constituent chain represented by formula (S-2) is preferably a constituent chain represented by formulas (S2-1) to (S2-3), and the configuration represented by formula (S2-1) Chains are more preferred.

［式中、
環Ｒ^T1、環Ｒ^T2、ｋ、ｍ^DA1、ｎ^d1、ｎ^T1、Ａｒ^DA1、Ａｒ^L1、Ａｒ^TW、Ｌ^d、Ｌ^T1、Ｒ^1T、Ｘ^T1及びＺ³は前記と同じ意味を表す。環Ｒ^T1、環Ｒ^T2、ｋ、ｍ^DA1、ｎ^T1、Ａｒ^DA1、Ａｒ^L1、Ｌ^d、Ｌ^T1、Ｒ^1T、Ｘ^T1及びＺ³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。複数存在するｎ^d1及びＡｒ^TWは、それぞれ同一でも異なっていてもよい。］

[In the formula,
Ring R ^T1 , ring R ^T2 , k, m ^DA1 , n ^d1 , n ^T1 , Ar ^DA1 , Ar ^L1 , Ar ^TW , L ^d , L ^T1 , R ^1T , X ^T1 and Z ³ have the same meanings as above. When a plurality of rings R ^T1 , R ^T2 , k, m ^DA1 , n ^T1 , Ar ^DA1 , Ar ^L1 , L ^d , L ^T1 , R ^1T , X ^T1 and Z ³ are present, they may be the same or different. good too. A plurality of n ^d1 and Ar ^TW may be the same or different. ]

Examples and preferred examples of ring R ^T1 , ring R ^T2 , m ^DA1 , n ^T1 , Ar ^DA1 , L ^T1 , R ^1T and X ^T1 in the constituent chains represented by formulas (S2-1) to (S2-3) The ranges are the same as the examples and preferred ranges of ring R ^T1 , ring R ^T2 , m ^DA1 , n ^T1 , Ar ^DA1 , L ^T1 , R ^1T and X ^T1 in the low molecular compound (T). When there are multiple rings R ^T1 , R ^T2 , m ^DA1 , n ^T1 , Ar ^DA1 , L ^T1 , R ^1T and X ^T1 , they are preferably the same.

Examples and preferred ranges of k, n ^d1 , Ar ^L1 , L ^d and Z ³ in the constituent chains represented by formulas (S2-1) to (S2-3) are represented by formula (3C) respectively. The same as the examples and preferred ranges of k, n ^d1 , Ar ^L1 , L ^d and Z ³ in the structural units. When there are multiple occurrences of k, Ar ^L1 , L ^d and Z ³ , each of them is preferably the same. A plurality of ^nd1 's are preferably the same.

Examples and preferred ranges of Ar ^TW in the constituent chains represented by formulas (S2-1) to (S2-3) are examples and preferred ranges of Ar ^TW in the constituent chain represented by formula (S-2) is the same as If there are multiple Ar ^TWs , they are preferably the same.

Examples of structural chains represented by formulas (S-1) to (S-3) include structural chains represented by the following formulas. In the formula, the definitions, examples and preferred ranges of k, n ^e1 , L ^e , R ^1T , R ^TS , R ^Y2 , R ^Y4 , R ^Y11 , Z ² and Z ³ are the same as above; When present, each may be the same or different.

In the constitutive chains represented by formulas (S-1) to (S-3), the bond between the group represented by Ar ^TW and the group represented by L ^S1 , the group represented by Ar ^TW and L ^S2 The bond between the group represented by and the bond between the group represented by Ar ^TW and the group represented by L ^S3 are each preferably a carbon-carbon bond.

In the constitutive chains represented by formulas (S-1) to (S-3), the dihedral angle between the group represented by Ar ^TW and the group represented by L ^S1 is θ ¹ , and Ar ^TW Among the dihedral angles between the group represented by L ^S2 and the group represented by L S2 , the minimum dihedral angle is θ ² , and the dihedral angle between the group represented by Ar ^TW and the group represented by L ^S3 is When θ3 is the smallest dihedral angle among the ^dihedral angles, θ1 ^, θ2 and θ3 ^{are each} preferably 45° or more, more preferably 50° or more, and 55°. ° or more is more preferable.

Gaussian09, a quantum chemical calculation program, can be used to calculate θ ¹ , θ ² and θ ³ . For example, for compounds in which the bonds in the constituent chains represented by formulas (S-1) to (S-3) are each replaced with a hydrogen atom, AM1, which is a semi-empirical molecular orbital method, is used to determine the θ ¹ , θ ² and θ ³ can be calculated by structurally optimizing the ground state of the compound.

In the polymer compound (TP), each of the structural chains represented by formulas (S-1) to (S-3) may contain only one type, or may contain two or more types. , is preferably included.

The total amount of the structural chains represented by formulas (S-1) to (S-3) is the structural unit (C ), preferably 20 to 100 mol%, more preferably 50 to 100 mol%, still more preferably 80 to 100 mol%, particularly preferably 100 mol%.

Examples of polymer compounds (TP) include polymer compound A and polymer compounds TP-A to TP-G. Here, the “other” structural unit means a structural unit other than the structural unit (C), the structural unit represented by formula (X), and the structural unit represented by formula (Y).

［表中、ｐ''、ｑ''、ｒ''、ｓ''、ｔ''及びｕ''は、各構成単位のモル比率を表す。ｐ''＋ｑ''＋ｒ''＋ｓ''＋ｔ''＝100であり、且つ、70≦ｐ''＋ｑ''＋ｒ''＋ｓ''＋ｔ''＋ｕ''≦100である。］

[In the table, p'', q'', r'', s'', t'' and u'' represent the molar ratio of each structural unit. p''+q''+r''+s''+t''=100 and 70≤p''+q''+r''+s''+t''+u''≤100. ]

The polymer compound (TP) may be any of a block copolymer, a random copolymer, an alternating copolymer, a graft copolymer, or may be in other forms. A copolymer obtained by copolymerizing monomers is preferable.

The polystyrene equivalent number average molecular weight of the polymer compound (TP) is preferably 5×10 ³ to 1×10 ⁶ , more preferably 1.5×10 ⁴ to 1×10 ⁵ .

[Method for producing polymer compound (TP)]
Next, a method for producing the polymer compound (TP) will be described.

The polymer compound (TP) includes, for example, a compound represented by formula (M-1), compounds represented by formulas (MT-1) to (MT-4), and other compounds (e.g., formula (M-2) to compounds represented by formulas (M-4)) can be produced by condensation polymerization. In this specification, the compounds used for producing the polymer compound (TP) of the present invention may be collectively referred to as "raw material monomer".

［式中、
ｃ、ｍ、ｍＡ、ｎ、ｎＡ、ｎ^c1、ｎ^d1、ｎ^e1、Ａｒ¹、Ａｒ²、Ａｒ³、Ａｒ⁴、Ａｒ^1M、Ａｒ^Y1、Ｋ^A、Ｌ^c、Ｌ^d、Ｌ^e、Ｔ^1C、Ｔ^2C、Ｔ^3C、Ｘ及びＸ’は、前記と同じ意味を表す。
Ｚ^C1～Ｚ^C16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表す。］

[In the formula,
^c , m, mA, n, nA, ^nc1 , ^nd1 , ^ne1 , ^{Ar1 ,} Ar2, ^Ar3 , ^Ar4 , ^Ar1M , ^ArY1 , ^KA , ^Lc , Ld, ^Le , T ^1C , T ^2C , T ^3C , X and X' have the same meanings as above.
Z ^C1 to Z ^C16 each independently represent a group selected from the group consisting of substituent group A and substituent group B. ]

For example, when Z ^C1 and Z ^C2 are groups selected from Substituent Group A, Z ^C3 to Z ^C16 are each selected from Substituent Group B.

For example, when Z ^C1 and Z ^C2 are groups selected from Substituent Group B, Z ^C3 to Z ^C16 are each selected from Substituent Group A.

<Substituent Group A>
chlorine atom, bromine atom, iodine atom, —OS(=O) ₂ R ^C1 (wherein R ^C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups have substituents; may be used.).

<Substituent Group B>
—B(OR ^C2 ) ₂ (In the formula, R ^C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. Multiple R ^C2 are may be the same or different, and may be linked to each other to form a ring structure together with the oxygen atoms to which they are attached.);
- A group represented by BF ₃ Q' (wherein Q' represents Li, Na, K, Rb or Cs);
-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 (In the formula, R ^C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, and these groups may have a substituent. Multiple R ^C3 may be the same or different, and may be linked to each other to form a ring structure together with the tin atom to which each is attached.).

The group represented by -B(OR ^C2 ) ₂ is exemplified by groups represented by the following formulae.

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 to form a group selected from substituent group A and substituent group B. The carbon atoms bonded to the group selected from are bonded to each other. Therefore, if a compound having two groups selected from the substituent group A and a compound having two groups selected from the substituent group B are subjected to a known coupling reaction, condensation polymerization of these compounds can be performed. A polymer can be obtained.

Condensation polymerization is usually carried out in the presence of a catalyst, a base and a solvent, but if necessary, it may be carried out in the presence of a phase transfer catalyst.

Examples of catalysts include bis(triphenylphosphine)palladium(II) dichloride, bis(tris-o-methoxyphenylphosphine)palladium(II) dichloride, tetrakis(triphenylphosphine)palladium(0), tris(dibenzylideneacetone ) dipalladium(0), palladium complexes such as palladium acetate, tetrakis(triphenylphosphine)nickel(0), [1,3-bis(diphenylphosphino)propane)nickel(II) dichloride, bis(1,4- transition metal complexes such as nickel complexes such as cyclooctadiene)nickel(0); Complexes having ligands such as 1,3-bis(diphenylphosphino)propane and bipyridyl can be mentioned. A catalyst may be used individually by 1 type, or may use 2 or more types together.

The amount of the catalyst to be used is usually 0.00001 to 3 molar equivalents as the amount of the transition metal with respect to the total number of moles of the raw material monomers.

Examples of bases and phase transfer catalysts include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, and tripotassium phosphate; organic bases such as butylammonium; and phase transfer catalysts such as tetrabutylammonium chloride and tetrabutylammonium bromide. Each of the base and the phase transfer catalyst may be used alone or in combination of two or more.

The amount of the base and the phase transfer catalyst used is usually 0.001 to 100 molar equivalents relative to the total number of moles of the 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 amount of solvent used is usually 10 to 100,000 parts by mass with respect to 100 parts by mass of the raw material monomers.

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

The post-treatment of the polymerization reaction is performed by a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and drying it. method, etc., shall be used singly or in combination. When the purity of the polymer compound is low, it can be purified by conventional methods such as crystallization, reprecipitation, continuous extraction using a Soxhlet extractor, and column chromatography.

[First composition]
The first organic layer comprises a polymer compound (TP) and at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material and an antioxidant. It may be a layer containing a composition containing and (hereinafter also referred to as a “first composition”). However, the hole transport material, the hole injection material, the electron transport material, the electron injection material and the light emitting material are different from the polymer compound (TP).

When the first composition contains a hole-transporting material, a hole-injecting material, an electron-transporting material, or an electron-injecting material, the external quantum efficiency of the light-emitting device of the present invention is excellent. , the electron-transporting material and the electron-injecting material each have an energy level higher than the lowest excited triplet state of the polymer compound (TP) and higher than the lowest excited singlet state of the polymer compound (TP) Having a high energy level is preferred.

[Hole transport material]
Hole-transporting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds.

Polymer compounds include, for example, polyvinylcarbazole and derivatives thereof; polyarylenes and derivatives thereof having aromatic amine structures in side chains or main chains. A polymer compound may be a compound having an electron-accepting site attached thereto. Examples of electron-accepting moieties include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, preferably fullerene.

In the first composition, the compounding amount of the hole transport material is usually 1 to 400 parts by mass, preferably 5 to 150 parts by mass, based on 100 parts by mass of the polymer compound (TP).
The hole transport materials may be used singly or in combination of two or more.

[Electron transport material]
Electron transport materials are classified into low-molecular-weight compounds and high-molecular-weight compounds.

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 derivatives thereof.

Polymer compounds include, for example, polyphenylene, polyfluorene, and derivatives thereof. The polymeric compounds may be doped with metals.

In the first composition, the amount of the electron-transporting material is usually 1-400 parts by mass, preferably 5-150 parts by mass, per 100 parts by mass of the polymer compound (TP).
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]
Hole-injecting materials and electron-injecting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds, respectively.

Examples of low-molecular compounds 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.

Polymer compounds include, for example, polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain; and a flexible polymer.

In the first composition, the compounding amount of the hole injection material and the electron injection material is usually 1 to 400 parts by mass, preferably 5 to 400 parts by mass, based on 100 parts by mass of the polymer compound (TP). 150 parts by mass.
Each of the electron injection material and the hole injection material may be used alone or in combination of two or more.

When the hole-injecting material or electron-injecting material comprises a conductive polymer, the electrical conductivity of the conductive polymer is preferably between 1×10 ⁻⁵ S/cm and 1×10 ³ S/cm. The conductive polymer can be doped with an appropriate amount of ions in order to set the electrical conductivity of the conductive polymer within this range.

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 anions include polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphor sulfonate ions. Examples of cations include lithium ion, sodium ion, potassium ion, and tetrabutylammonium ion.
The ions to be doped may be used singly or in combination of two or more.

[Light emitting material]
Light-emitting materials are classified into low-molecular-weight compounds and high-molecular-weight compounds. Low-molecular-weight compounds are preferable because the light-emitting device of the present invention has excellent external quantum efficiency.

Examples of low-molecular-weight compounds include fluorescent compounds represented by naphthalene and its derivatives, anthracene and its derivatives, perylene and its derivatives, and phosphorescent compounds having iridium, platinum or europium as a central metal. .

Examples of the polymer compound include a phenylene group, a naphthalene diyl group, a fluorenediyl group, a phenanthenediyl group, a dihydrophenanthenediyl group, a group represented by the formula (X) described later, a carbazoldiyl group, a phenoxazinediyl group, Polymer compounds containing phenothiazinediyl groups, anthracenediyl groups, pyrenediyl groups and the like can be mentioned.

As the light-emitting material, the phosphorescent compounds represented by formulas Ir-1 to Ir-5 are preferable, and the phosphorescent compounds represented by formula Ir-1 are preferred because the light-emitting device of the present invention has excellent external quantum efficiency. more preferred.

［式中、
Ｒ^D11～Ｒ^D20、Ｒ^D21～Ｒ^D26及びＲ^D31～Ｒ^D37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。Ｒ^D11～Ｒ^D20、Ｒ^D21～Ｒ^D26及びＲ^D31～Ｒ^D37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。
－Ａ^D1---Ａ^D2－、ｎ_D1、ｎ_D2及びＲ^D1～Ｒ^D8は、前記と同じ意味を表す。］

[In the formula,
R ^D11 to R ^D20 , R ^D21 to R ^D26 and R ^D31 to R ^D37 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, or a monovalent It represents a heterocyclic group or a halogen atom, and these groups may have a substituent. When a plurality of R ^D11 to R ^D20 , R ^D21 to R ^D26 and R ^D31 to R ^D37 are present, they may be the same or different.
-A ^D1 ---A ^D2 -, n _D1 , n _D2 and R ^D1 to R ^D8 have the same meanings as above. ]

Examples of the anionic bidentate ligand represented by -A ^D1 --A ^D2 - include ligands represented by the following formulae.

［式中、＊は、Ｉｒと結合する部位を表す。］

[In the formula, * represents a site that binds to Ir. ]

Examples of the phosphorescent compound include the following phosphorescent compounds.

When the first composition contains a light-emitting material, the light-emitting device of the present invention has excellent external quantum efficiency, so the polymer compound (TP) has an energy level higher than the lowest excited triplet state of the light-emitting material. and preferably have an energy level higher than the lowest excited singlet state of the light-emitting material.

In the first composition, the content of the luminescent material is usually 0.1 to 50 parts by mass when the total of the polymer compound (TP) and the luminescent material is 100 parts by mass.
A luminescent material may be used individually by 1 type, or may use 2 or more types together.

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the polymer compound (TP) and does not inhibit light emission and charge transport. Examples thereof include phenolic antioxidants and phosphorus antioxidants.

In the first composition, the blending amount of the antioxidant is usually 0.001 to 10 parts by mass based on 100 parts by mass of the polymer compound (TP).
An antioxidant may be used individually by 1 type, or may use 2 or more types together.

[First ink]
A composition containing a polymer compound (TP) and a solvent (hereinafter also referred to as "first ink") can be suitably used in wet processes such as spin coating and inkjet.

The viscosity of the first ink may be adjusted depending on the type of wet method, but when applied to a printing method such as an inkjet method in which a solution passes through an ejection device, clogging and flight deflection during ejection are less likely to occur. Therefore, it is preferably 1 to 20 mPa·s at 25°C.

The solvent contained in the first ink is preferably a solvent capable of dissolving or uniformly dispersing the solid content in the ink. Examples of solvents 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; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate. Ethylene glycol, glycerin, polyhydric alcohol solvents such as 1,2-hexanediol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; N-methyl-2-pyrrolidone, N , and N-dimethylformamide. A solvent may be used individually by 1 type, or may use 2 or more types together.

In the first ink, the blending amount of the solvent is usually 1,000 to 100,000 parts by mass based on 100 parts by mass of the polymer compound (TP).

<Second organic layer>
A crosslinked body of the crosslinkable material can be obtained by making the crosslinked material crosslinked by the above-described method, conditions, and the like.

The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from Group A of cross-linking groups (hereinafter also referred to as "low-molecular-weight compound of the second organic layer"), or selected from Group A of cross-linking groups. It is a polymer compound containing a cross-linked structural unit having at least one cross-linking group (hereinafter also referred to as "a polymer compound of the second organic layer"), and the light-emitting device of the present invention has excellent external quantum efficiency. It is preferably a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from Group A of cross-linking groups.

As the cross-linking group selected from the cross-linking group A, the light-emitting device of the present invention has excellent external quantum efficiency, and therefore, preferably, the groups represented by the formulas (XL-1) to (XL-4) and the formulas (XL-7) to the formula (XL-10) or a cross-linking group represented by formulas (XL-14) to (XL-17), more preferably a cross-linking represented by formula (XL-1) or (XL-17) group, more preferably a cross-linking group represented by formula (XL-17).

[Polymer Compound for Second Organic Layer]
The structural unit having at least one cross-linking group selected from cross-linking group A contained in the polymer compound of the second organic layer is a structural unit represented by formula (2) or represented by formula (2′) However, it may be a structural unit represented by the following formula.

When the polymer compound of the second organic layer contains two or more structural units having at least one cross-linking group selected from Group A, it has at least one cross-linking group selected from Group A. At least two of the structural units preferably have different cross-linking groups. Combinations of cross-linking groups different from each other include formula (XL-1), formula (XL-2), formula (XL-5) to formula (XL-8), or formula (XL-14) to formula (XL-16). A combination of a cross-linking group represented by formula (XL-3), formula (XL-4), formula (XL-13) or formula (XL-17) is preferred, and formula (XL -1) or a combination of a cross-linking group represented by formula (XL-16) and a cross-linking group represented by formula (XL-17) is more preferable, and a cross-linking group represented by formula (XL-1) and , and a cross-linking group represented by formula (XL-17) are more preferred.

Structural Unit Represented by Formula (2) nA is preferably an integer of 0 to 3, more preferably 1, since the light-emitting device of the present invention has excellent external quantum efficiency.

n is preferably 2 because the light-emitting device of the present invention has excellent external quantum efficiency.

Ar ³ is preferably an aromatic hydrocarbon group optionally having a substituent, since the light-emitting device of the present invention has excellent external quantum efficiency.

The number of carbon atoms in the aromatic hydrocarbon group represented by Ar ³ is usually 6 to 60, preferably 6 to 30, more preferably 6 to 18, not including the number of carbon atoms in the substituents. be.
The arylene group portion excluding n substituents of the aromatic hydrocarbon group represented by Ar ³ is preferably a group represented by formulas (A-1) to (A-20), More preferably, it is a group represented by formula (A-1), formula (A-2), formula (A-7), formula (A-9) or formula (A-19), and these groups are It may have a substituent.

The number of carbon atoms in the heterocyclic group represented by Ar ³ is usually 2 to 60, preferably 3 to 30, more preferably 4 to 18, not including the number of carbon atoms in the substituents.
The divalent heterocyclic group portion excluding n substituents of the heterocyclic group represented by Ar ³ is preferably a group represented by formulas (AA-1) to (AA-34). be.

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

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

The alkylene group and cycloalkylene group represented by ^LA may have a substituent. Preferred substituents that the alkylene group and the cycloalkylene group may have are an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a halogen atom and a cyano group, and these groups further have a substituent. may be

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

The divalent heterocyclic group represented by L ^A is preferably a group represented by formulas (AA-1) to (AA-34).

^LA is preferably an arylene group or an alkylene group, more preferably a phenylene group, a fluorenediyl group or an alkylene group, since it facilitates the production of the polymer compound of the second organic layer. The group may have a substituent.

As the cross-linking group represented by X, since the light-emitting device of the present invention has excellent external quantum efficiency, the cross-linking groups of formulas (XL-1) to (XL-4) and formulas (XL-7) to (XL -10) or a cross-linking group represented by formulas (XL-14) to (XL-17), more preferably a cross-linking group represented by formula (XL-1) or formula (XL-17) and more preferably a cross-linking group represented by formula (XL-17).

The total amount of structural units represented by formula (2) is the total amount of structural units contained in the polymer compound of the second organic layer, since the polymer compound of the second organic layer has excellent stability and crosslinkability. It is preferably 0.5 to 80 mol %, more preferably 3 to 65 mol %, still more preferably 5 to 50 mol % based on the amount.
The structural unit represented by the formula (2) may be contained in one type or two or more types in the polymer compound of the second organic layer.

When the polymer compound of the second organic layer contains two or more structural units represented by formula (2), at least two of the structural units represented by formula (2) are crosslinked represented by X. Preferably the groups are different from each other. The preferred range of the combination of the different cross-linking groups represented by X is the same as the above-described preferred range of the combination of the different cross-linking groups.

Structural Unit Represented by Formula (2′) mA is preferably an integer of 0 to 3, more preferably 0, since the light-emitting device of the present invention has excellent external quantum efficiency.

m is preferably 1 or 2, more preferably 2, since the light-emitting device of the present invention has excellent external quantum efficiency.

c is preferably 0 because it facilitates the production of the polymer compound of the second organic layer and the external quantum efficiency of the light-emitting device of the present invention is excellent.

Ar ⁵ is preferably an aromatic hydrocarbon group optionally having a substituent, since the light-emitting device of the present invention has excellent external quantum efficiency.

The definition and examples of the arylene group portion of the aromatic hydrocarbon group represented by Ar ⁵ excluding m substituents are the same as the definition and examples of the arylene group represented by Ar ^x2 in formula (X) described later. is.

Definitions and examples of the divalent heterocyclic group portion excluding the m substituents of the heterocyclic group represented by Ar ⁵ refer to the divalent heterocyclic group represented by Ar ^X2 in formula (X) described later. Same as part definitions and examples.

Definitions and examples of the divalent group excluding m substituents in the "group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded" represented by Ar ⁵ are defined in Ar ^X2 in formula (X) described later. is the same as the definition and examples of the divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded to each other.

Ar ⁴ and Ar ⁶ are preferably optionally substituted arylene groups, since the light-emitting device of the present invention has excellent external quantum efficiency.

Definitions and examples of the arylene group and the divalent heterocyclic group represented by Ar ⁴ and Ar ⁶ refer to the arylene group and the divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 in formula (X) below. Same as definitions and examples.

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

Definitions and examples of the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by K ^A respectively refer to the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by ^LA . It is the same as the definition and examples of the ring group.

^KA is preferably a phenylene group or a methylene group, since this facilitates the production of the polymer compound of the second organic layer.

The definition and examples of the cross-linking group represented by X' are the same as the definition and examples of the cross-linking group represented by X above.

The total amount of the structural units represented by the formula (2′) is the second It is preferably 0.5 to 50 mol%, more preferably 3 to 30 mol%, still more preferably 5 to 20 mol%, relative to the total amount of structural units contained in the polymer compound of the organic layer 2. be.
The structural unit represented by the formula (2') may be contained in one type or two or more types in the polymer compound of the second organic layer.

When the polymer compound of the second organic layer contains two or more structural units represented by formula (2′), at least two of the structural units represented by formula (2′) are represented by X′. It is preferred that the cross-linking groups used are different from each other. The preferred range of the combination of cross-linking groups represented by X', which are different from each other, is the same as the preferred range of the combination of cross-linking groups that are different from each other.

- Preferred embodiment of structural unit represented by formula (2) or (2') Examples of structural units represented by formula (2) include formulas (2-1) to (2-13). structural unit. Examples of structural units represented by formula (2') include structural units represented by formulas (2'-1) to (2'-4). Among these, structural units represented by formulas (2-1) to (2-13) are preferred, and more preferably formula (2 -1) to structural units represented by formulas (2-6) or (2-13).

• Other Structural Units Since the polymer compound of the second organic layer has excellent hole-transporting properties, it is preferable that the polymer compound further includes a structural unit represented by the formula (X). Moreover, the polymer compound of the second organic layer preferably further contains a structural unit represented by the above formula (Y), since the light-emitting device of the present invention has excellent external quantum efficiency.

［式中、
ａ^X1及びａ^X2は、それぞれ独立に、０以上１０以下の整数を表す。
Ａｒ^X1及びＡｒ^X3は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^X2及びＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2及びＡｒ^X4が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。
Ｒ^X1、Ｒ^X2及びＲ^X3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^X2及びＲ^X3が複数存在する場合、それらはそれぞれ同一でも異なっていてもよい。］

[In the formula,
a ^X1 and a ^X2 each independently represent an integer of 0 or more and 10 or less.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ^X2 and Ar ^X4 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. When multiple Ar ^X2 and Ar ^X4 are present, they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple R ^X2 and R ^X3 are present, they may be the same or different. ]

a ^X1 is preferably an integer of 2 or less, more preferably 1, because the light-emitting device of the present invention has excellent external quantum efficiency.
a ^X2 is preferably an integer of 2 or less, more preferably 0, since the light-emitting device of the present invention has excellent external quantum efficiency.

R ^X1 , R ^X2 and R ^X3 are preferably alkyl groups, cycloalkyl groups, aryl groups or monovalent heterocyclic groups, and these groups may have substituents.

Arylene groups represented by Ar ^X1 and Ar ^X3 are more preferably groups represented by formula (A-1) or formula (A-9), and 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)-Formula (AA-26). These groups may have a substituent.

Ar ^X1 and Ar ^X3 are preferably optionally substituted arylene groups.

Arylene groups represented by Ar ^X2 and Ar ^X4 are more preferably represented by formulas (A-1), (A-6), (A-7), (A-9) to (A-11 ) or a group represented by formula (A-19), and these groups may have a substituent.

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

Examples of the "divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded" represented by Ar ^X2 and Ar ^X4 include groups represented by the following formulae. and these may have a substituent.

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

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

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

Ar ^X2 and Ar ^X4 are preferably optionally substituted arylene groups.

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 substituents. may have.

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

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

[In the formula, R ^X4 and R ^X5 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group, or a cyano represents a group, and these groups may have a substituent. Multiple 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 atoms to which they are bonded. ]

Examples of structural units represented by formula (X) include structural units represented by formulas (X1-1)-(X1-11).

Since the polymer compound of the second organic layer has excellent hole-transporting property and excellent external quantum efficiency of the light-emitting device of the present invention, the structural unit represented by the formula (X) and the structural unit represented by the formula (Y) It is preferable to include a structural unit represented by

The definition and examples of the structural unit represented by the formula (Y) that the polymer compound of the second organic layer may contain are the formula (Y) that the polymer compound (TP) may contain. Same as definitions and examples of represented units.

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

When the polymer compound of the second organic layer contains the structural unit represented by the formula (X), the total amount of the structural unit represented by the formula (X) is excellent in the hole-transport property. It is preferably 0.1 to 90 mol %, more preferably 35 to 70 mol %, still more preferably 45 to 50 mol %, relative to the total amount of structural units contained in the polymer compound in the organic layer.

When the polymer compound of the second organic layer contains the structural unit represented by formula (Y), the total amount of the structural unit represented by formula (Y) is such that the light-emitting device of the present invention has excellent external quantum efficiency. Therefore, it is preferably 0.5 to 90 mol %, more preferably 30 to 60 mol %, based on the total amount of structural units contained in the polymer compound of the second organic layer.

Examples of the polymer compound for the second organic layer include polymer compounds IP-A to IP-H. Here, "other structural units" mean structural units other than the structural units represented by formula (2), formula (2'), formula (X) and formula (Y).

［表中、ｐ’、ｑ’、ｒ’、ｓ’及びｔ’は、各構成単位のモル比率を表す。ｐ’＋ｑ’＋ｒ’＋ｓ’＋ｔ’＝100であり、かつ、70≦ｐ’＋ｑ’＋ｒ’＋ｓ’≦100である。］

[In the table, p', q', r', s' and t' represent the molar ratio of each structural unit. p'+q'+r'+s'+t'=100 and 70≤p'+q'+r'+s'≤100. ]

The polymer compound of the second organic layer may be a block copolymer, a random copolymer, an alternating copolymer, or a graft copolymer. It is preferably a copolymer obtained by copolymerizing the seed raw material monomers.

The polystyrene equivalent number average molecular weight of the polymer compound of the second organic layer is preferably 5×10 ³ to 1×10 ⁶ , more preferably 1.5×10 ⁴ to 1×10 ⁵ .

[Method for producing polymer compound for second organic layer]
The polymer compound of the second organic layer can be produced by the same method as the production method of the polymer compound (TP) described above.

[Low-molecular-weight compound for second organic layer]
The low-molecular-weight compound of the second organic layer is preferably a low-molecular-weight compound represented by formula (3).

m ^B1 is preferably an integer of 0 to 5, more preferably 0, because it facilitates synthesis of the crosslinked material.

m ^B2 is preferably an integer of 0 to 5, more preferably 1, because it facilitates the synthesis of the cross-linking material and the external quantum efficiency of the light-emitting device of the present invention is excellent.

m ^B3 is preferably an integer of 0 to 4, more preferably 0, because it facilitates the synthesis of the crosslinked material.

Definitions and examples of the arylene group moiety excluding m ^B3 substituents of the aromatic hydrocarbon group represented by Ar ⁷ are the same as definitions and examples of the arylene group represented by Ar ^X2 in the above formula (X). are the same.

Definitions and examples of the divalent heterocyclic group moiety excluding m ^B3 substituents of the heterocyclic group represented by Ar ⁷ refer to the divalent heterocyclic ring represented by Ar ^X2 in the above formula (X). Same as definitions and examples of base moieties.

Definitions and examples of the divalent group excluding m ^B3 substituents of the group in which at least one aromatic hydrocarbon ring and at least one heterocyclic ring are directly bonded represented by ^Ar are represented by the above formula The definition and examples of the divalent group in (X) in which at least one arylene group represented by Ar ^X2 and at least one divalent heterocyclic group are directly bonded are the same.

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

Ar ⁷ is preferably an aromatic hydrocarbon group, and this aromatic hydrocarbon group may have a substituent, since the light-emitting device of the present invention has excellent external quantum efficiency.

Definitions and examples of the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by L ^B1 are, respectively, the alkylene group, cycloalkylene group, arylene group, and divalent heterocyclic group represented by L ^A described above. are the same as the definition and examples of the heterocyclic group of

L ^B1 is preferably an alkylene group, an arylene group or an oxygen atom, more preferably a phenylene group or an alkylene group, since it facilitates the synthesis of the cross-linking material, and these groups have a substituent. good too.

X'' is preferably a bridging group, an aryl group or a monovalent heterocyclic group represented by any one of formulas (XL-1) to (XL-17), more preferably formula (XL -16) or a naphthyl group, and these groups may have a substituent.

Examples of low-molecular-weight compounds for the second organic layer include low-molecular-weight compounds represented by formulas (3-1) to (3-16).

Low-molecular-weight compounds for the second organic layer are available from, for example, Aldrich, Luminescence Technology Corp., American Dye Source, and the like. In addition, the low-molecular compound of the second organic layer may be synthesized according to the methods described in, for example, WO 1997/033193, WO 2005/035221, and WO 2005/049548. can be done.

In the second organic layer, one type of crosslinked body of the crosslinkable material may be contained alone, or two or more types may be contained.

[Second composition]
The second organic layer comprises a crosslinked material of a crosslinkable material and at least one material selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material and an antioxidant. It may be a layer containing a composition containing (hereinafter also referred to as "second composition").

Examples and preferred ranges of the hole-transporting material, electron-transporting material, hole-injecting material and electron-injecting material contained in the second composition are the hole-transporting material and electron-transporting material contained in the first composition. , are the same as the examples and preferred ranges of the hole-injecting material and the electron-injecting material.

The luminescent material contained in the second composition includes, for example, a fluorescent compound which may be contained in the first composition, and a phosphorescent compound having iridium, platinum or europium as a central metal. mentioned. A luminescent material may be used individually by 1 type, or may use 2 or more types together.

In the second composition, the compounding amounts of the hole transport material, the electron transport material, the hole injection material, the electron injection material, and the light-emitting material are usually 1 when the crosslinked product of the crosslink material is 100 parts by mass. ~400 parts by mass.

The example and preferred range of the antioxidant contained in the second composition are the same as the example and preferred range of the antioxidant contained in the first composition. In the second composition, the amount of the antioxidant compounded is usually 0.001 to 10 parts by mass when the crosslinked product of the crosslinkable material is taken as 100 parts by mass.

[Second ink]
A composition containing a cross-linking material and a solvent (hereinafter also referred to as "second ink") can be suitably used in the wet method described in the section on the first ink. The preferred range of viscosity for the second ink is the same as the preferred range for the viscosity of the first ink. The example and preferred range of the solvent contained in the second ink are the same as the example and preferred range of the solvent contained in the first ink.

In the second ink, the blending amount of the solvent is usually 1,000 to 100,000 parts by mass when the cross-linking material is 100 parts by mass.

<Layer structure of light-emitting element>
The light emitting device of the present invention may have layers other than the anode, cathode, first organic layer and second organic layer.

In the light-emitting device of the present invention, the first organic layer is usually a light-emitting layer (hereinafter also referred to as "first light-emitting layer").

In the light-emitting device of the present invention, the second organic layer is usually a hole-transporting layer, a second light-emitting layer or an electron-transporting layer, preferably a hole-transporting layer or a second light-emitting layer, more preferably is the hole transport layer.

In the light-emitting device of the present invention, the first organic layer and the second organic layer are preferably adjacent to each other because the external quantum efficiency of the light-emitting device of the present invention is excellent.
In the light-emitting device of the present invention, the second organic layer is preferably a layer provided between the anode and the first organic layer because the light-emitting device of the present invention has excellent external quantum efficiency. It is more preferably a hole-transporting layer or a second light-emitting layer provided between one organic layer, and more preferably a hole-transporting layer provided between the anode and the first organic layer. .

In the first organic layer of the light-emitting device of the present invention, one type of polymer compound (TP) may be contained alone, or two or more types thereof may be contained. In the second organic layer of the light emitting device of the present invention, the crosslinked body of the crosslinkable material may be contained singly or in combination of two or more.

In the light emitting device of the present invention, when the second organic layer is a hole transport layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferable to further have a hole injection layer between the two organic layers. When the second organic layer is a hole-transporting layer provided between the anode and the first organic layer, the external quantum efficiency of the light-emitting device of the present invention is excellent. Furthermore, it is preferable to further have at least one layer of an electron injection layer and an electron transport layer.

In the light-emitting device of the present invention, when the second organic layer is provided between the anode and the first organic layer, the external quantum efficiency of the light-emitting device of the present invention is excellent. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the second organic layer. When the second organic layer is the second light emitting layer provided between the anode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferred to further have at least one layer of an electron injection layer and an electron transport layer in between.

In the light-emitting device of the present invention, when the second organic layer is provided between the cathode and the first organic layer, the external quantum efficiency of the light-emitting device of the present invention is excellent. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the first organic layer. When the second organic layer is the second light emitting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light emitting device of the present invention is excellent. It is preferred to further have at least one layer of an electron injection layer and an electron transport layer in between.

In the light-emitting device of the present invention, when the second organic layer is an electron transport layer provided between the cathode and the first organic layer, the external quantum efficiency of the light-emitting device of the present invention is excellent. It is preferable to further have at least one layer of a hole injection layer and a hole transport layer between the organic layers of the above. When the second organic layer is an electron-transporting layer provided between the cathode and the first organic layer, the external quantum efficiency of the light-emitting device of the present invention is excellent. , preferably further includes an electron injection layer.

Specific layer structures of the light-emitting device of the present invention include, for example, layer structures represented by (D1) to (D15). The light-emitting device of the present invention usually has a substrate, but may be laminated on the substrate from the anode, or may be laminated on the substrate from the cathode.

(D1) anode/second light-emitting layer (second organic layer)/first light-emitting layer (first organic layer)/cathode (D2) anode/hole transport layer (second organic layer)/second 1 light-emitting layer (first organic layer)/cathode (D3) anode/hole injection layer/second light-emitting layer (second organic layer)/first light-emitting layer (first organic layer)/cathode (D4) anode/hole injection layer/second emitting layer (second organic layer)/first emitting layer (first organic layer)/electron transport layer/cathode (D5) anode/hole injection layer / second light emitting layer (second organic layer) / first light emitting layer (first organic layer) / electron injection layer / cathode (D6) anode / hole injection layer / second light emitting layer (second organic layer)/first emitting layer (first organic layer)/electron transport layer/electron injection layer/cathode (D7) anode/hole injection layer/hole transport layer (second organic layer)/second 1 light emitting layer (first organic layer)/cathode (D8) anode/hole injection layer/hole transport layer (second organic layer)/first light emitting layer (first organic layer)/electron transport Layer/cathode (D9) anode/hole injection layer/hole transport layer (second organic layer)/first emitting layer (first organic layer)/electron injection layer/cathode (D10) anode/holes injection layer/hole transport layer (second organic layer)/first emitting layer (first organic layer)/electron transport layer/electron injection layer/cathode (D11) anode/hole injection layer/hole transport Layer/Second Emissive Layer (Second Organic Layer)/First Emissive Layer (First Organic Layer)/Electron Transport Layer/Electron Injection Layer/Cathode (D12) Anode/Hole Injection Layer/Hole Transport Layer (second organic layer)/first emitting layer (first organic layer)/second emitting layer/electron transport layer/electron injection layer/cathode (D13) anode/hole injection layer/hole transport Layer/First Emissive Layer (First Organic Layer)/Second Emissive Layer (Second Organic Layer)/Electron Transport Layer/Electron Injection Layer/Cathode (D14) Anode/Hole Injection Layer/Hole Transport layer/first light emitting layer (first organic layer)/electron transport layer (second organic layer)/electron injection layer/cathode (D15) anode/hole injection layer/hole transport layer (second organic layer)/second light-emitting layer/first light-emitting layer (first organic layer)/electron transport layer/electron injection layer/cathode

In (D1) to (D15), "/" means that the layers before and after it are laminated adjacently. Specifically, “second light emitting layer (second organic layer)/first light emitting layer (first organic layer)” means the second light emitting layer (second organic layer) and the first light emitting layer (second organic layer). is laminated adjacent to the light emitting layer (first organic layer).

In the light emitting device of the present invention, each of the anode, the hole injection layer, the hole transport layer, the second light emitting layer, the electron transport layer, the electron injection layer and the cathode is provided with two or more layers, if necessary. good too.
When there are multiple anodes, hole-injection layers, hole-transport layers, second light-emitting layers, electron-transport layers, electron-injection layers, and cathodes, they may be the same or different.

The thicknesses of the anode, hole-injection layer, hole-transport layer, first light-emitting layer, second light-emitting layer, electron-transport layer, electron-injection layer and cathode are usually 1 nm to 1 μm.

In the light-emitting device of the present invention, the order, number and thickness of the layers to be laminated may be adjusted in consideration of the external quantum efficiency, driving voltage and luminance lifetime of the light-emitting device.

[Second light-emitting layer]
The second light-emitting layer is usually a second organic layer or a layer containing a light-emitting material, preferably a layer containing a light-emitting material. When the second light-emitting layer is a layer containing a light-emitting material, the light-emitting material contained in the second light-emitting layer includes, for example, the light-emitting material that the second composition may contain. be done. The light-emitting material contained in the second light-emitting layer may be contained singly or in combination of two or more.
When the light-emitting device of the present invention has a second light-emitting layer and the hole-transporting layer and the electron-transporting layer described later are not the second organic layer, the second light-emitting layer is the second organic layer. is preferably

[Hole transport layer]
The hole-transporting layer is usually a second organic layer or a layer containing a hole-transporting material, preferably a second organic layer. When the hole-transporting layer is a layer containing a hole-transporting material, the hole-transporting material includes, for example, the hole-transporting material that the first composition may contain. The hole-transporting material contained in the hole-transporting layer may be contained alone or in combination of two or more.
When the light-emitting device of the present invention has a hole-transporting layer and the second light-emitting layer described above and the electron-transporting layer described later are not the second organic layer, the hole-transporting layer is the second organic layer. Preferably.

[Electron transport layer]
The electron-transporting layer is usually a second organic layer or a layer containing an electron-transporting material, preferably a layer containing an electron-transporting material. When the electron-transporting layer is a layer containing an electron-transporting material, the electron-transporting material contained in the electron-transporting layer includes, for example, the electron-transporting material that the first composition may contain. . The electron-transporting material contained in the electron-transporting layer may be contained alone or in combination of two or more.
When the light-emitting device of the present invention has an electron-transporting layer and the second light-emitting layer and the hole-transporting layer are not the second organic layer, the electron-transporting layer is the second organic layer. is preferred.

[Hole Injection Layer and Electron Injection Layer]
A hole injection layer is a layer containing a hole injection material. The hole injection material contained in the hole injection layer includes, for example, the hole injection material that the first composition may contain. The hole injection material contained in the hole injection layer may be contained singly or in combination of two or more.
An electron injection layer is a layer containing an electron injection material. The electron injection material contained in the electron injection layer includes, for example, the electron injection material that the first composition may contain. The electron injection material contained in the electron injection layer may be contained singly or in combination of two or more.

[Substrate/electrode]
The substrate in the light emitting device may be a substrate on which an electrode can be formed and which does not change chemically when the organic layer is formed.

Examples of materials 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. conductive compounds of; silver-palladium-copper complex (APC); NESA, gold, platinum, silver and copper.

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

In the light-emitting device of the present invention, at least one of the anode and cathode is usually transparent or translucent.
Examples of methods for forming the anode and cathode include dry methods such as vacuum deposition.

[Method for manufacturing light-emitting element]
In the light-emitting device of the present invention, a low-molecular-weight compound is used as a method for forming each layer such as the first light-emitting layer, the second light-emitting layer, the hole transport layer, the electron transport layer, the hole injection layer, and the electron injection layer. For example, a dry method and a wet method can be mentioned, and when a polymer compound is used, for example, a wet method can be mentioned.
The first light-emitting layer, the second light-emitting layer, the hole-transporting layer, the electron-transporting layer, the hole-injecting layer, and the electron-injecting layer are composed of the first ink, the second ink, the light-emitting material described above, the hole It can be formed by a wet method using inks each containing a transport material, an electron transport material, a hole injection material and an electron injection material.

[Use of light-emitting element]
In order to obtain planar light emission using a light-emitting element, a planar anode and a planar cathode may be arranged so as to overlap each other. In order to obtain patterned light emission, there are methods such as placing a mask with patterned windows on the surface of a planar light emitting element, and forming a layer that is desired to be a non-light-emitting portion to be substantially non-light-emitting. There are methods for patterning the anode or cathode, or both electrodes. By forming a pattern by any of these methods and arranging some 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 form a dot matrix display device, both the anode and the cathode should be formed in stripes and arranged so as to be perpendicular to each other. Partial color display and multicolor display are possible by a method of separately coating a plurality of kinds of polymer compounds having different emission colors and a method of using a color filter or a fluorescence conversion filter. A dot-matrix display device can be passively driven, or can be actively driven in combination with a TFT or the like. These display devices can be used as displays for computers, televisions, mobile terminals, and the like. A planar light-emitting element can be suitably used as a planar light source for backlighting a liquid crystal display device or as a planar light source for illumination. If a flexible substrate is used, it can also be used as a curved light source and display device.

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

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

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

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

NMR was measured by the following method.
Approximately 0.5 mL of 5 to 10 mg of a measurement sample is added to about 0.5 mL of heavy chloroform (CDCl ₃ ), heavy tetrahydrofuran, heavy dimethylsulfoxide, heavy acetone, heavy N,N-dimethylformamide, heavy toluene, heavy methanol, heavy ethanol, heavy 2-propanol, or It was dissolved in methylene dichloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).

High performance liquid chromatography (HPLC) area percentage values were used as an index of compound purity. Unless otherwise specified, this value is the 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 to a concentration of 0.01 to 0.2% by mass, and 1 to 10 μL was injected into the HPLC depending on the concentration. Acetonitrile/tetrahydrofuran was used as the mobile phase for HPLC while changing the ratio from 100/0 to 0/100 (volume ratio), and flowed at a flow rate of 1.0 mL/min. Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column with equivalent performance was used as the column. A photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used as a detector.

Gaussian09, a quantum chemical calculation program, was used to calculate ΔE _ST , oscillator strength, θ ¹ , θ ² and θ ³ of the compound. After structural optimization of the ground state of the compound using the B3LYP-level density functional theory, ΔE _ST and oscillator strength were calculated using the B3LYP-level time-dependent density functional theory. When the polymer compound contains the constituent chains represented by the above formulas (S-1) to (S-3), semi-empirical molecules are obtained for compounds in which the bonds in the constituent chains are each replaced with a hydrogen atom. After optimizing the ground state of the compound using the orbital method AM1, θ ¹ , θ ² and θ ³ were calculated.

<Synthesis Example 1> Synthesis of Compound T1 Compound T1 was synthesized according to the method described in JP-A-2010-196040.

<Synthesis Example 2> Synthesis of compound T2 (synthesis of compound T2-1)

After replacing the gas in the flask equipped with a stirrer with argon gas, 1-bromo-3-hexylbenzene (60.0 g), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane Adduct (PdCl ₂ (dppf).CH ₂ Cl ₂ ) (10.2 g), bispinacolato diboron (75.8 g), potassium acetate (35.9 g) and 1,2-dimethoxyethane (510 mL) were added and the mixture was heated to reflux temperature. and stirred for 24 hours. After cooling the resulting mixture to room temperature, heptane (510 mL) and Celite 545 (Aldrich, 72 g) were added. The resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using a silica gel column (developing solvent: hexane/toluene) to obtain 56.4 g of compound T2-1 as a pale yellow oil. The HPLC area percentage value (UV=220 nm) was 97.6%.

(Synthesis of compound T2-2)

After replacing the gas in the flask equipped with a stirrer with argon gas, 3,6-dibromocarbazole (13.0 g), compound T2-1 (25.4 g), toluene (390 mL) and ethanol (130 mL) were added. After bubbling argon gas into the resulting mixture for 5 minutes while stirring, tetrakis(triphenylphosphine)palladium(0) (2.3 g) was added followed by potassium carbonate (33.2 g) and water (130 mL). An aqueous potassium carbonate solution was added thereto, and the mixture was heated under reflux for 7 hours. After cooling the obtained mixture to room temperature, the aqueous layer was separated, and the obtained organic layer was further washed with water. Magnesium sulfate was added to the obtained organic layer. The resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using a silica gel column (developing solvent: hexane/toluene) to obtain 12.8 g of compound T2-2 as a pale yellow solid. The HPLC area percentage value was 96.1%.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 8.35-8.30 (m, 2H), 8.07 (brs, 1H), 7.75-7.30 (m, 10H), 7.18-7.16 (m, 2H), 2.72 (t,4H),1.76-1.64(m,4H),1.48-1.20(m,12H),0.98-0.84(m,6H).

(Synthesis of compound T2-4)

After replacing the gas in the flask equipped with a stirrer with argon gas, compound T2-3 (synthesized according to the method described in Eur. J. Org. Chem. 2013, 6619; 4.6 g), compound T2-2. (8.6 g), copper (I) iodide (1.5 g), trans-1,2-cyclohexanediamine (1.1 g) and xylene (106 mL) were added. After bubbling the resulting mixture with argon gas for 5 minutes, potassium phosphate (6.8 g) was added, the temperature was raised to 130°C, and the mixture was stirred at 130°C for 8 hours. After cooling the resulting mixture to room temperature, heptane (70 mL) was added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using Wakogel 50C18 (manufactured by Wako Pure Chemical Industries, Ltd., developing solvent: acetonitrile/ethyl acetate) to obtain 8.8 g of compound T2-4 as a white solid. The HPLC area percentage value was 99.3%.
¹ H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 8.50 (d, 2H), 8.39 (d, 4H), 8.17 (d, 2H), 7.96 (d, 2H), 7.81 (dd, 2H), 7.68-7.63(m,4H),7.55-7.50(m,8H),7.48-7.43(m,4H),7.40-7.31(m,6H),7.19-7.13(m,4H),2.70(t,8H) ), 2.41(s,3H), 1.74-1.63(m,8H), 1.45-1.23(m,24H), 0.94-0.84(m,12H).

(Synthesis of compound T2-5)

After replacing the gas in the flask equipped with a stirrer with argon gas, compound T2-4 (8.8 g), tetrahydrofuran (70 mL), dimethyl sulfoxide (42 mL) and 33% by mass potassium hydroxide aqueous solution (11.6 g) were added. , and heated to reflux for 2 hours. After cooling the resulting mixture to room temperature, water (141 mL) and toluene (211 mL) were added, the aqueous layer was separated, and the resulting organic layer was further washed with water. Magnesium sulfate was added to the obtained organic layer, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using a silica gel column (developing solvent: hexane/toluene) to obtain 7.2 g of compound T2-5 as a white solid. The HPLC area percentage value was 98.9%. By repeating this operation, the required amount of compound T2-5 was obtained.

(Synthesis of compound T2-6)

After replacing the gas in the flask equipped with a stirrer with argon gas, compound T2-5 (8.3 g), 1-bromo-4-iodobenzene (6.2 g), copper (I) iodide (1.4 g), Trans-1,2-cyclohexanediamine (1.0 g) and xylene (83 mL) were added. After bubbling the resulting mixture with argon gas for 5 minutes, potassium phosphate (6.2 g) was added, the temperature was raised to 80°C, and the mixture was stirred at 80°C for 8 hours. After cooling the resulting mixture to room temperature, heptane (83 mL) was added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using a silica gel column (developing solvent: hexane/toluene) to obtain 8.8 g of compound T2-6 as a white solid. The HPLC area percentage value was 94.9%.

(Synthesis of compound T2-7)

After replacing the gas in the flask equipped with a stirrer with argon gas, compound T2-6 (8.5 g), 1,1'-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane adduct (PdCl ₂ (dppf).CH ₂ Cl ₂ ) (0.5 g), bispinacolato diboron (3.4 g), potassium acetate (1.3 g) and 1,2-dimethoxyethane (85 mL) were added and the temperature was raised to reflux temperature, Stir at reflux temperature for 17 hours. After cooling the resulting mixture to room temperature, toluene (85 mL) and Celite 545 (manufactured by Aldrich, 7 g) were added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. . The resulting crude product was purified using a silica gel column (developing solvent: hexane/toluene) to obtain 6.1 g of compound T2-7 as a white solid. The HPLC area percentage value was 99.0%.

(Synthesis of compound T2)

After replacing the gas in the flask equipped with a stirrer with argon gas, compound T2-7 (6.1 g) and compound T2-8 (synthesized according to the method described in JP-A-2010-260879; 2.9 g). , toluene (109 mL) and ethanol (22 mL) were added. After bubbling argon gas into the resulting mixture for 5 minutes while stirring, tetrakis(triphenylphosphine)palladium(0) (0.5 g) was added, followed by 20 wt% tetraethylammonium hydroxide (15.1 g) and water ( 38 mL) was added, the temperature was raised to 50°C, and the mixture was stirred at 50°C for 1 hour. After cooling the obtained mixture to room temperature, the aqueous layer was separated, and the obtained organic layer was further washed with water. Magnesium sulfate was added to the resulting organic layer, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using an alumina column (developing solvent: hexane/toluene) and then purified using a silica gel column (developing solvent: hexane/toluene) to give compound T2 as a pale yellow solid at 4.6 got g. The HPLC area percentage value was above 99.5%.
LC-MS (ESI, positive): 1602[M+H] ^+
1 H-NMR (CDCl ₃ , 300 MHz) δ (ppm): 9.09 (d, 2H), 8.70-8.65 (m, 4H), 8.44-8.37 (m, 6H), 8.00 (d, 2H), 7.84 (d ,2H),7.77-7.65(m,10H),7.57-7.46(m,12H),7.41-7.35(m,4H),7.18-7.15(m,4H),2.70(t,8H),1.75-1.64 (m,8H),1.44-1.26(m,24H),0.95-0.84(m,12H).

<Synthesis Example 3> Synthesis of compound T3 (synthesis of compound T3-1)

After making the inside of the reaction vessel a nitrogen gas atmosphere, 4-hexylaniline (19.2 g), 3-bromotriphenylamine (28.0 g), Pd ₂ (dba) ₃ (dba) _0.73 (1.45 g), t-Bu ₃ PHBF ₄ (0.75 g), t-BuONa (16.6 g) and toluene (350 mL) were added and stirred at 50° C. for 2.5 hours. After cooling the resulting mixture to room temperature, it was filtered through a silica gel short column. The obtained filtrate was concentrated under reduced pressure to obtain a brown oil. The resulting oil was purified using silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain compound T3-1 (29.6 g, colorless oil). The HPLC area percentage value of compound T3-1 was 99.2%.

(Synthesis of compound T3-2)

After making the inside of the reaction vessel a nitrogen gas atmosphere, 3-bromo-4,5-dichlorotoluene (8.2 g), compound T3-1 (14.8 g), Pd ₂ (dba) ₃ (dba) _0.73 (0.56 g), t-Bu ₃ PHBF ₄ (0.30 g), t-BuONa (6.6 g) and o-xylene (130 g) were added and stirred at 50° C. for 2.5 hours. The resulting mixture was cooled to room temperature and then filtered through a short column laminated with silica gel/Celite. The obtained filtrate was concentrated under reduced pressure to obtain a brown oil. The resulting oil was purified using silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain compound T3-2 (14.9 g, colorless oil). The HPLC area percentage value of compound T3-2 was 99.0%.

(Synthesis of compound T3-3)

After making the inside of the reaction vessel a nitrogen gas atmosphere, bis(4-tert-butylphenyl)amine (7.0 g), compound T3-2 (12.5 g), Pd ₂ (dba) ₃ (dba) _0.73 (0.42 g), t-Bu ₃ PHBF ₄ (0.23 g), t-BuONa (3.7 g) and o-xylene (42 g) were added and stirred at 50° C. for 10 hours and then at 70° C. for 1 hour. The resulting mixture was cooled to room temperature and then filtered through a short column laminated with silica gel/Celite. The obtained filtrate was concentrated under reduced pressure to obtain a brown oil. The obtained oil was purified by silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain compound T3-3 (9.2 g, colorless oil). The HPLC area percentage value of compound T3-3 was 92.2%.

(Synthesis of compound T3-H)

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound T3-3 (7.5 g) and tert-butylbenzene (56 mL) were added, and after cooling to 0 ° C., a t-BuLi / pentane solution ( 1.5M, 9.6 mL) was slowly added. After the resulting mixture was stirred at 60° C. for 3 hours, pentane was distilled off under reduced pressure. After the resulting mixture was cooled to -50°C, BBr ₃ (4.5 g) was added and stirred at -50°C for 0.5 hours. The resulting mixture was heated to 120°C and reacted at 120°C for 3 hours. After cooling the resulting mixture to room temperature, an aqueous sodium acetate solution and ethyl acetate were added, and the resulting organic layer was washed with ion-exchanged water. The resulting organic layer was concentrated under reduced pressure to obtain a yellow oil. The obtained oil was purified by silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain a yellow solid. The resulting solid was dispersed in acetonitrile and filtered to obtain compound T3-H (1.1 g, yellow solid). The HPLC area percentage value of compound T3-H was 99.4%.
LC-MS (APCI, positive): m/z=798.5 [M+H]+
¹ H-NMR (CD ₂ Cl ₂ , 400 MHz) δ (ppm): 0.92 (m, 3H), 1.36 (m, 6H), 1.39 (s, 9H), 1.44 (s, 9H), 1.58 (m, 2H ),2.08(s,3H),2.61(dd,2H),5.92(d,2H),6.19(d,1H),6.61(d,1H),6.87(dd,1H),7.02(t,2H) ,7.07(m,6H),7.2-7.3(m,8H),7.42(dd,1H),7.68(d,2H),8.67(d,1H),8.79(d,1H).

(Synthesis of compound T3)

After making the inside of the reaction vessel a nitrogen gas atmosphere, compound T3-H (0.91 g), bis(pinacolato)diboron (B ₂ pin ₂ ; 0.58 g), 4,4'-di-tert-butyl-2,2' -bipyridyl (dtbpy; 0.013 g), (1,5-cyclooctadiene)(methoxy)iridium(I) dimer ([Ir(cod)(OMe)] ₂ ; 0.0155 g) and cyclohexane (23 mL) were added and C. for 2 hours. After cooling the obtained mixture to room temperature, the obtained organic layer was washed with ion-exchanged water. The obtained organic layer was liquid-separated, the solid insoluble in the organic layer was removed by filtration, and the obtained filtrate was concentrated under reduced pressure to obtain a yellow oil. The obtained oil was purified by silica gel column chromatography (mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain compound T3 (0.21 g, yellow oil). The HPLC area percentage value of compound T3 was 97.4%. Compound T3 was obtained as a mixture of four isomers in a molar ratio of compound T3-a: compound T3-b: compound T3-c: compound T3-d=7.5:37.1:43.0:12.4.
¹ H-NMR (CD ₂ Cl ₂ , 400 MHz) δ (ppm): 0.92 (m, 3H), 1.30, 1.32, 1.38, 1.39, 1.44 (s, total 33H), 1.3-1.4 (m, (6H)) , 1.44 (s, 9H), 1.58 (m, 2H), 2.08 (m, 3H), 2.59 (t, 2H), 5.92 (m, 2H), 6.09 (d, 0.12H: compound T3-d), 6.11 (d, 0.43H: compound T3-c), 6.20 (d, 0.37H: compound T3-b), 6.26 (d, 0.08H: compound T3-a), 6.60 (d, 0.6H), 6.61 (d, 0.4H), 6.80(m, 0.6H), 6.86(m, 0.4H), 7.0-7.1(m, 4.3H), 7.1-7.2(m, 1.2H), 7.2-7.3(m, 5.5H), 7.4-7.5 (m, 2.6H), 7.51 (m, 0.27H: compound T3-d), 7.59 (m, 1H), 7.68 (d, 2H), 7.83 (m, 0.13H: compound T3-d), 8.6-8.7(m,1H),8.79(m,1H).

<Synthesis Example 4> Synthesis of compound T4 (synthesis of compound T4-1)

After making the inside of the reaction vessel an argon gas atmosphere, 3-methyl-9H-carbazole (6.05 g), 1-chloro-4-iodobenzene (9.95 g), Pd ₂ (dba) ₃ (dba) _0.75 (0.55 g) , t-Bu ₃ PHBF ₄ (0.30 g), t-BuONa (4.18 g) and xylene (121 mL) were added and stirred at 50° C. for 2 hours. After adding toluene (121 mL) to the obtained mixture, it was cooled to room temperature, and the obtained mixture was filtered through a silica gel short column. The obtained filtrate was concentrated under reduced pressure to obtain a brown oil. The resulting oil was purified by silica gel column chromatography (developing solvent: mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain compound T4-1 (5.4 g, pale yellow solid). The HPLC area percentage value of compound T4-1 was 96.1%.

(Synthesis of compound T4-2)

After creating an argon gas atmosphere in the reaction vessel, compound T4-1 (4.44 g), chloroform (58 mL) and trifluoroacetic acid (8.9 mL) were charged and ice-cooled. After adding N-iodosuccinimide (3.39 g) in two portions to the resulting mixture, the mixture was stirred for 1 hour while being heated. A 10 wt% sodium sulfite aqueous solution (20 mL) was added to the resulting mixture, then water (58 mL) and hexane (115 mL) were added, and then the layers were separated, and the resulting organic layer was washed with water (58 mL). . After magnesium sulfate was added to the obtained organic layer, it was filtered through a silica gel short column. The obtained filtrate was concentrated under reduced pressure to obtain a yellowish brown solid. The obtained solid was recrystallized with a mixture of toluene and ethanol.
These operations were repeated to obtain compound T4-2 (6.3 g, white solid). The HPLC area percentage value of compound T4-2 was 98.8%.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm): 8.39 (d, 1H), 7.85 (s, 1H), 7.61 (dd, 1H), 7.58-7.52 (m, 2H), 7.47-7.41 (m , 2H), 7.25-7.22 (m, 2H), 7.10 (d, 1H), 2.50 (s, 3H).

(Synthesis of compound T4-3)

After making the inside of the reaction vessel an argon gas atmosphere, compound T4-2 (5.50 g), 3,6-dimethyl-9H-carbazole (3.09 g), copper (I) iodide (1.25 g), trans-1,2 -Cyclohexanediamine (0.90 g) and xylene (110 mL) were added. After bubbling the resulting mixture with argon gas for 5 minutes, potassium phosphate (11.18 g) was added, the temperature was raised to 130°C, and the mixture was stirred at 130°C for 2 hours. After cooling the resulting mixture to room temperature, heptane (220 mL) was added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel column chromatography (developing solvent: mixed solvent of hexane and toluene), concentrated under reduced pressure and dried to obtain compound T4-3 (6.3 g, white solid). The HPLC area percentage value was 99.5%.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm): 8.22-8.19 (m, 1H), 7.94-7.91 (m, 2H), 7.90-7,87 (m, 1H), 7.64-7.55 (m, 4H), 7.52-7.49 (m, 2H), 7.33-7.17 (m, 6H), 2.56 (s, 6H), 2.53 (s, 3H).

(Synthesis of compound T4-4)

After the reaction vessel was filled with an argon gas atmosphere, compound T4-3 (4.00 g), a palladium catalyst ((2-Dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-( 2'-amino-1,1'-biphenyl)]palladium(II) methanesulfonate, Xphos Pd G3, Aldrich) (0.21 g), bispinacolato diboron (6.28 g), potassium acetate (3.17 g) and cyclopentylmethyl Ether (48 mL) was added, the temperature was raised to the reflux temperature, and the mixture was stirred at the reflux temperature for 1 hour. After cooling the resulting mixture to room temperature, heptane (34 mL) and celite (Celite 545, manufactured by Aldrich) (5 g) were added, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to give a crude product. got The resulting crude product was purified using a silica gel column (developing solvent: hexane/toluene).
These operations were repeated to obtain compound T4-4 (5.5 g, pale yellow solid) as a white solid. The HPLC area percentage value was 99.4%.

(Synthesis of compound T4)

反応容器内をアルゴンガス雰囲気とした後、化合物Ｔ４－４(4.33g)、化合物Ｔ２－８（4.79g）、トルエン(153mL)及びエタノール(31mL)を加えた。得られた混合物を攪拌しながらアルゴンガスで５分間バブリングした後、テトラキス（トリフェニルホスフィン）パラジウム（０）(0.87g)を加え、次いで、20質量％水酸化テトラエチルアンモニウム(24.9g)と水(53mL)との混合液を加えた後、50℃に昇温して50℃で１時間攪拌した。得られた混合物を室温まで冷却した後、トルエンで希釈し、水層を分離し、得られた有機層を水で洗浄した。得られた有機層に硫酸マグネシウムを加え、得られた混合液をろ過し、得られたろ液を減圧濃縮して粗生成物を得た。得られた粗生成物をアルミナカラム（展開溶媒：ヘキサン／トルエン）を用いて精製し、次いで、シリカゲルカラム（展開溶媒：ヘキサン／トルエン）を用いて精製して、薄黄色固体として化合物Ｔ４(4.0g、薄黄色固体)得た。HPLC面積百分率値は99.5％以上であった。
¹H-NMR(CDCl₃,400MHz)δ(ppm)：9.92-8.97 (m, 2H), 8.67-8.63 (m, 4H), 8.24 (d, 1H), 7.96-7.85 (m, 5H), 7.75-7.68 (m, 5H), 7.56-7.48 (m, 2H), 7.33-7.27 (m, 3H), 7.23-7.19 (m, 2H), 2.57-2.54 (m, 9H).

After the inside of the reaction vessel was replaced with an argon gas atmosphere, compound T4-4 (4.33 g), compound T2-8 (4.79 g), toluene (153 mL) and ethanol (31 mL) were added. After bubbling argon gas into the resulting mixture for 5 minutes while stirring, tetrakis(triphenylphosphine)palladium(0) (0.87 g) was added, followed by 20 wt% tetraethylammonium hydroxide (24.9 g) and water ( 53 mL) was added, the temperature was raised to 50°C, and the mixture was stirred at 50°C for 1 hour. After the resulting mixture was cooled to room temperature, it was diluted with toluene, the aqueous layer was separated, and the resulting organic layer was washed with water. Magnesium sulfate was added to the resulting organic layer, the resulting mixture was filtered, and the resulting filtrate was concentrated under reduced pressure to obtain a crude product. The resulting crude product was purified using an alumina column (developing solvent: hexane/toluene) and then purified using a silica gel column (developing solvent: hexane/toluene) to obtain compound T4 (4.0%) as a pale yellow solid. g, pale yellow solid). The HPLC area percentage value was above 99.5%.
¹ H-NMR (CDCl ₃ , 400 MHz) δ (ppm): 9.92-8.97 (m, 2H), 8.67-8.63 (m, 4H), 8.24 (d, 1H), 7.96-7.85 (m, 5H), 7.75 -7.68 (m, 5H), 7.56-7.48 (m, 2H), 7.33-7.27 (m, 3H), 7.23-7.19 (m, 2H), 2.57-2.54 (m, 9H).

<Synthesis Examples MC1 and MC2> Synthesis of Phosphorescent Compounds MC-1 and MC-2 The phosphorescent compound MC-1 was synthesized according to the method described in WO2009/131255.
Phosphorescent compound MC-2 was synthesized according to the method described in JP-A-2008-179617.

<Synthesis Example E1> Synthesis of Fluorescent Compound E1 Fluorescent compound E1 was synthesized according to the method described in International Publication No. 2007/058368.

<Synthesis Examples M1 to M15> Synthesis and Obtainment of Compounds M1 to M15 Compounds M1, M2 and M6 were synthesized according to the method described in WO2002/045184.
Compound M3 was synthesized according to the method described in WO2011/049241.
Compound M4 was synthesized according to the method described in JP-A-2011-174062.
Compound M5 was synthesized according to the method described in WO2005/049546.
Compound M7 was synthesized according to the method described in JP-A-2008-106241.
Compounds M8, M9 and M15 were synthesized according to the method described in WO2013/146806.
Compound M10 was synthesized according to the method described in WO2015/145871.
Compound M11 was synthesized according to the method described in JP-A-2010-189630.
A commercially available product was used as compound M12.
Compound M13 was synthesized according to the method described in WO2012/086671.
Compound M14 was synthesized according to the method described in WO2013/191086.

<Synthesis Example TP1> Synthesis of polymer compound TP-1 Polymer compound TP-1 was synthesized using compound M11, compound M6 and compound T1 according to the method described in JP-A-2010-196040. The polymer compound TP-1 had an Mn of 1.2×10 ⁵ and an Mw of 4.0×10 ⁵ .

In the polymer compound TP-1, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M11, the structural unit derived from the compound M6, and the structural unit derived from the compound T1 It is a copolymer composed of a molar ratio of 50:40:10. The ΔE _ST and oscillator strength of compound T1-H were 0.16 eV and 0.0001, respectively.

Polymer compound TP-1 contained a structural chain represented by the following formula, and θ ² of the structural chain was 57°.

<Example TP2> Synthesis of polymer compound TP-2 After making the inside of the reaction vessel an inert gas atmosphere, compound M11 (825 mg), compound M6 (772 mg), compound T2 (547 mg), dichlorobis(tris-o-methoxy Phenylphosphine)palladium (1.5 mg) and toluene (35 mL) were added and heated to 105°C. A 20% by mass tetraethylammonium hydroxide aqueous solution (26 mL) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 5.5 hours. After that, phenylboronic acid (83 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (1.5 mg) were added thereto and refluxed for 17 hours. After cooling the obtained reaction solution, it was washed once with water, twice with 10% by mass dilute aqueous hydrochloric acid, twice with 3% by mass aqueous ammonia solution, and twice with water. After magnesium sulfate was added to the obtained solution, purification was performed by passing through an alumina column and a silica gel column in that order. The obtained solution was added dropwise to methanol, and after stirring, the resulting precipitate was collected by filtration and dried to obtain 1.1 g of polymer compound TP-2. The polymer compound TP-2 had an Mn of 5.7×10 ⁴ and an Mw of 1.2×10 ⁵ .

In the polymer compound TP-2, the theoretical values obtained from the amounts of the raw materials charged are the structural units derived from the compound M11, the structural units derived from the compound M6, and the structural units derived from the compound T2. It is a copolymer composed of a molar ratio of 50:40:10. The ΔE _ST and oscillator strength of compound T2-H were 0.06 eV and 0.0922, respectively.

Polymer compound TP-2 contained a structural chain represented by the following formula, and θ ² of the structural chain was 57°.

<Example TP3> Synthesis of polymer compound TP-3 Compound T3 (0.104 g), compound M12 (0.502 g), compound M13 (0.628 g), dichlorobis(tris-o-methoxyphenylphosphine) palladium (0.86 mg) and Toluene (27 mL) was mixed and heated to 105°C. Thereafter, a 10% by mass tetraethylammonium hydroxide aqueous solution (18 mL) was added dropwise thereto, and the mixture was refluxed for 4 hours. After that, phenylboronic acid (48.8 mg) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (0.9 mg) were added thereto and refluxed for 6 hours. After cooling the resulting reaction mixture, it was washed twice with water, twice with a 10% by mass aqueous solution of hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with water. The resulting solution was added dropwise to methanol and stirred to cause precipitation. The resulting precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in that order. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The resulting precipitate was collected by filtration and dried to obtain 0.68 g of polymer compound TP-3. The Mn of the polymer compound TP-3 was 4.5×10 ⁴ and the Mw was 1.1×10 ⁵ .

In the polymer compound TP-3, the theoretical value obtained from the amount of the raw material charged is that the structural units derived from the compound M12, the structural units derived from the compound T3 and the structural units derived from the compound M13 It is a copolymer composed of a molar ratio of 45:5:50. The ΔE _ST and oscillator strength of compound T3-H were 0.44 eV and 0.3782, respectively.

<Example TP4> Synthesis of polymer compound TP-4 Compound M11 (0.643 g), compound M14 (0.613 g), compound T2 (0.427 g), dichlorobis(tri-o-methoxyphenylphosphine)palladium (1.22 mg) and Toluene (24.2 g) was mixed and heated to 80°C. Thereafter, a 10% by mass tetraethylammonium hydroxide aqueous solution (20 mL) was added dropwise thereto, and the mixture was refluxed for 12 hours. After that, phenylboronic acid (64.7 mg) and dichlorobis(tri-o-methoxyphenylphosphine)palladium (0.12 mg) were added thereto and refluxed for 11 hours. After cooling the resulting reaction mixture, it was washed once with water, twice with a 10% by mass hydrochloric acid aqueous solution, twice with a 3% by mass aqueous ammonia solution, and twice with water. Water was removed from the resulting mixture by distillation under reduced pressure. The resulting solution was purified by passing through a column packed with a mixture of alumina and silica gel. The obtained solution was added dropwise to methanol, and after stirring, the resulting precipitate was collected by filtration and dried to obtain 0.76 g of polymer compound TP-4. The polymer compound TP-4 had an Mn of 5.3×10 ⁴ and an Mw of 1.1×10 ⁵ .

In the polymer compound TP-4, the theoretical values obtained from the amounts of the raw materials charged are the structural units derived from the compound M11, the structural units derived from the compound M14, and the structural units derived from the compound T2. It is a copolymer composed of a molar ratio of 50:40:10. Polymeric compound TP-4 contains the same constituent chains as polymeric compound TP-2.

<Example TP5> Synthesis of polymer compound TP-5 Compound M11 (0.626 g), compound M15 (0.629 g), compound T2 (0.414 g), dichlorobis(tri-o-methoxyphenylphosphine)palladium (1.28 mg) and Toluene (24.5 g) was mixed and heated to 80°C. Thereafter, a 10% by mass tetraethylammonium hydroxide aqueous solution (20 mL) was added dropwise thereto, and the mixture was refluxed for 7 hours. After that, phenylboronic acid (62.9 mg) and dichlorobis(tri-o-methoxyphenylphosphine)palladium (0.12 mg) were added thereto and refluxed for 10 hours. After cooling the resulting reaction mixture, it was washed once with water, twice with a 10% by mass hydrochloric acid aqueous solution, twice with a 3% by mass aqueous ammonia solution, and twice with water. Water was removed from the resulting mixture by distillation under reduced pressure. The resulting solution was purified by passing through a column packed with a mixture of alumina and silica gel. The obtained solution was added dropwise to methanol, and after stirring, the resulting precipitate was collected by filtration and dried to obtain 0.98 g of polymer compound TP-5. The polymer compound TP-5 had Mn of 5.2×10 ⁴ and Mw of 1.1×10 ⁵ .

In the polymer compound TP-5, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M11, the structural unit derived from the compound M15, and the structural unit derived from the compound T2 It is a copolymer composed of a molar ratio of 50:40:10. Polymeric compound TP-5 contains the same constituent chains as polymeric compound TP-2.

<Example TP6> Synthesis of polymer compound TP-6 Compound M11 (0.798 g), compound M6 (0.730 g), compound T4 (0.280 g), dichlorobis(tri-o-methoxyphenylphosphine)palladium (1.48 mg) and Toluene (24.2 g) was mixed and heated to 80°C. Thereafter, a 20% by mass tetraethylammonium hydroxide aqueous solution (20 mL) was added dropwise thereto, and refluxed for 2.5 hours. After that, phenylboronic acid (81.2 mg) and dichlorobis(tri-o-methoxyphenylphosphine)palladium (1.47 mg) were added thereto and refluxed for 6 hours. After cooling the resulting reaction mixture, it was washed once with water, twice with a 10% by mass hydrochloric acid aqueous solution, twice with a 3% by mass aqueous ammonia solution, and twice with water. Water was removed from the resulting mixture by distillation under reduced pressure. The resulting solution was purified by passing through a column packed with a mixture of alumina and silica gel. The obtained solution was added dropwise to methanol, and after stirring, the resulting precipitate was collected by filtration and dried to obtain 0.71 g of polymer compound TP-6. The Mn of the polymer compound TP-6 was 9.5×10 ⁴ and the Mw was 2.2×10 ⁵ .

In the polymer compound TP-6, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M11, the structural unit derived from the compound M6, and the structural unit derived from the compound T4 are It is a copolymer composed of a molar ratio of 50:40:10. The ΔE _ST and oscillator strength of compound T4-H were 0.06 eV and 0.0781, respectively.

Polymer compound TP-6 contained a structural chain represented by the following formula, and θ ² of the structural chain was 57°.

<Synthesis Example IP1> Synthesis of polymer compound IP-1 Polymer compound IP-1 was synthesized using compound M1 and compound M2 according to the method described in JP-A-2012-36381. The Mn of the polymer compound IP-1 was 8.1×10 ⁴ and the Mw was 3.4×10 ⁵ .
In the polymer compound IP-1, the theoretical value obtained from the amount of the raw material charged was that the structural units derived from the compound M1 and the structural units derived from the compound M2 were composed at a molar ratio of 50:50. It is a copolymer.

<Synthesis Example IP2> Synthesis of polymer compound IP-2 Polymer compound IP-2 was synthesized using compound M1, compound M2 and compound M3 according to the method described in WO2011/049241. The polymer compound IP-2 had Mn of 8.9×10 ⁴ and Mw of 4.2×10 ⁵ .
In the polymer compound IP-2, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M1, the structural unit derived from the compound M2, and the structural unit derived from the compound M3 are It is a copolymer composed of a molar ratio of 50:42.5:7.5.

<Synthesis Example IP3> Synthesis of polymer compound IP-3 Polymer compound IP-3 was prepared using compound M4, compound M5, compound M6 and compound M7 according to the method described in JP-A-2012-144722. Synthesized. The polymer compound IP-3 had Mn of 5.0×10 ⁴ and Mw of 2.5×10 ⁵ .
The theoretical values obtained from the amounts of the raw materials used in the polymer compound IP-3 are the structural units derived from the compound M4, the structural units derived from the compound M5, the structural units derived from the compound M6, and the compound A copolymer composed of structural units derived from M7 in a molar ratio of 50:30:12.5:7.5.

<Synthesis example IP4> Synthesis of polymer compound IP-4 After the reaction vessel was filled with an inert gas atmosphere, compound M8 (1.07 g), compound M9 (0.198 g), compound M2 (0.919 g), dichlorobis [tris ( 2-Methoxyphenyl)phosphine]palladium (1.8 mg) and toluene (50 mL) were added and heated to 100°C. A 20% by mass tetraethylammonium hydroxide aqueous solution (8.7 mL) was added dropwise to the obtained reaction solution, and the mixture was refluxed for 6 hours. After that, 2-ethylphenylboronic acid (60.0 mg), 20% by mass tetraethylammonium hydroxide aqueous solution (8.7 mL) and dichlorobis[tris(2-methoxyphenyl)phosphine]palladium (1.8 mg) were added thereto, and the mixture was stirred for 16 hours. Refluxed. After that, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80°C for 2 hours. After cooling the resulting reaction solution, it was washed twice with 3.6% by mass hydrochloric acid, twice with 2.5% by mass aqueous ammonia solution, and 6 times with water. When the resulting solution was added dropwise to methanol, precipitation occurred. The resulting precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in that order. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The resulting precipitate was collected by filtration and dried to obtain 1.14 g of polymer compound IP-4. The Mn of the polymer compound IP-4 was 3.6×10 ⁴ and the Mw was 2.0×10 ⁵ .
In the polymer compound IP-4, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M8, the structural unit derived from the compound M9, and the structural unit derived from the compound M2 are It is a copolymer with a molar ratio of 40:10:50.

<Synthesis Example IP5> Synthesis of polymer compound IP-5 Polymer compound IP-5 was synthesized using compound M10, compound M9 and compound M5 according to the method described in WO2015/145871. The polymer compound IP-5 had Mn of 2.3×10 ⁴ and Mw of 1.2×10 ⁵ .
In the polymer compound IP-5, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M10, the structural unit derived from the compound M9, and the structural unit derived from the compound M5 are It is a copolymer with a molar ratio of 45:5:50.

<Synthesis example IP6> Synthesis of polymer compound IP-6 After making the inside of the reaction vessel an inert gas atmosphere, compound M11 (1.74 g), compound M5 (3.19 g), dichlorobis(triphenylphosphine) palladium (2.5 mg). and toluene (40 mL) were added and heated to 80°C. A 20% by mass tetraethylammonium hydroxide aqueous solution (12 mL) was added dropwise to the reaction solution, and the mixture was refluxed for 8 hours. After the reaction, phenylboronic acid (0.427 g) and dichlorobis(triphenylphosphine)palladium (2.5 mg) were added thereto and refluxed for 17 hours. After that, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80°C for 2 hours. After cooling the resulting reaction solution, it was washed twice with water, twice with a 3% by mass aqueous acetic acid solution, and twice with water. When the resulting solution was added dropwise to methanol, precipitation occurred. The resulting precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in that order. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The resulting precipitate was collected by filtration and dried to obtain 3.00 g of polymer compound IP-6. The polymer compound IP-6 had an Mn of 4.5×10 ⁴ and an Mw of 1.5×10 ⁵ .
According to the theoretical value obtained from the amount of the starting material, the polymer compound IP-6 is composed of structural units derived from the compound M11 and structural units derived from the compound M5 at a molar ratio of 50:50. It is a copolymer.

<Synthesis Example IP7> Synthesis of polymer compound IP-7 After the reaction vessel was filled with an inert gas atmosphere, compound M11 (3.995 g), compound M5 (6.237 g), compound M7 (0.519 g), dichlorobis(tris- o-Methoxyphenylphosphine)palladium (7.1 mg) and toluene (190 mL) were added and heated to 105°C. Thereafter, a 20% by mass tetraethylammonium hydroxide aqueous solution (28 mL) was added dropwise thereto, and the mixture was refluxed for 4 hours. Thereafter, phenylboronic acid (97.5 mg), 20% by mass tetraethylammonium hydroxide aqueous solution (28 mL) and dichlorobis(tris-o-methoxyphenylphosphine)palladium (7.1 mg) were added thereto and refluxed for 6 hours. After cooling the resulting reaction mixture, it was washed twice with water, twice with a 10% by mass aqueous solution of hydrochloric acid, twice with 3% by mass aqueous ammonia, and twice with water. The resulting solution was added dropwise to methanol and stirred to cause precipitation. The resulting precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in that order. The resulting solution was added dropwise to methanol and stirred to produce a precipitate. The resulting precipitate was collected by filtration and dried to obtain 6.65 g of polymer compound IP-7. The polymer compound IP-7 had an Mn of 2.6×10 ⁴ and an Mw of 1.4×10 ⁵ .
In the polymer compound IP-7, the theoretical value obtained from the amount of the raw material charged is that the structural unit derived from the compound M11, the structural unit derived from the compound M5, and the structural unit derived from the compound M7 are A copolymer with a molar ratio of 50:42.5:7.5.

<Comparative Example CD1> Production and Evaluation of Light-Emitting Element CD1 (Formation of Anode and Hole-Injection Layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. A film of AQ-1200 (manufactured by Plectronics), which is a hole injection material, was formed to a thickness of 65 nm on the anode by a spin coating method. A hole injection layer was formed by heating on a hot plate at 170° C. for 15 minutes in an air atmosphere.

(Formation of second organic layer)
Polymer compound IP-1 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method, and a second layer was formed by heating on a hot plate at 180° C. for 60 minutes in a nitrogen gas atmosphere. to form an organic layer of

(Formation of first organic layer)
Polymer compound TP-1 and phosphorescent compound MC-1 (polymer compound TP-1/phosphorescent compound MC-1=70% by mass/30% by mass) are dissolved in xylene at a concentration of 1.6% by mass. rice field. Using the obtained xylene solution, a film having a thickness of 80 nm was formed on the second organic layer by spin coating, and the first organic layer was formed by heating at 150° C. for 10 minutes in a nitrogen gas atmosphere. formed.

(Formation of cathode)
After reducing the pressure of the substrate on which the first organic layer was formed to 1.0×10 ⁻⁴ Pa or less in a vapor deposition machine, as a cathode, about 4 nm of sodium fluoride was deposited on the first organic layer, followed by sodium fluoride. About 80 nm of aluminum was evaporated on top of the layer. After vapor deposition, the light-emitting element CD1 was produced by sealing with a glass substrate.

(Evaluation of Light Emitting Element)
EL light emission was observed by applying a voltage to the light emitting element CD1. The external quantum efficiency (EQE) at 1000cd/ ^m2 was measured. Table 3 shows the results.

<Example D1> Production and evaluation of light emitting device D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to a glass substrate by a sputtering method. A film of AQ-1200 (manufactured by Plectronics), which is a hole injection material, was formed to a thickness of 65 nm on the anode by a spin coating method. A hole injection layer was formed by heating on a hot plate at 170° C. for 15 minutes in an air atmosphere.

(Formation of second organic layer)
Polymer compound IP-2 was dissolved in xylene at a concentration of 0.6% by mass. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by a spin coating method, and a second layer was formed by heating on a hot plate at 180° C. for 60 minutes in a nitrogen gas atmosphere. to form an organic layer of By this heating, the polymer compound IP-2 became a crosslinked product.

(Formation of first organic layer)
Polymer compound TP-1 and phosphorescent compound MC-1 (polymer compound TP-1/phosphorescent compound MC-1=70% by mass/30% by mass) are dissolved in xylene at a concentration of 1.6% by mass. rice field. Using the obtained xylene solution, a film having a thickness of 80 nm was formed on the second organic layer by spin coating, and the first organic layer was formed by heating at 150° C. for 10 minutes in a nitrogen gas atmosphere. formed.

(Formation of cathode)
After reducing the pressure of the substrate on which the first organic layer was formed to 1.0×10 ⁻⁴ Pa or less in a vapor deposition machine, as a cathode, about 4 nm of sodium fluoride was deposited on the first organic layer, followed by sodium fluoride. About 80 nm of aluminum was evaporated on top of the layer. After vapor deposition, the light-emitting device D1 was produced by sealing with a glass substrate.

(Evaluation of Light Emitting Element)
EL light emission was observed by applying a voltage to the light emitting element D1. EQE at 1000cd/ ^m2 was measured. Table 3 shows the results.

<Examples D2 to D16, D4', D14', D15' and Comparative Example CD2> Production and Evaluation of Light Emitting Elements D2 to D16, D4', D14', D15' and CD2 In Example D1, the first organic layer Light-emitting devices D2 to D16, D4', D14' and D15' were produced in the same manner as in Example D1 except that the second organic layer and the second organic layer were as shown in Table 3, and EQE was measured. A light-emitting device CD2 was fabricated in the same manner as in Comparative Example CD1, except that the first organic layer and the second organic layer in Comparative Example CD1 were as shown in Table 3, and EQE was measured. Table 3 shows the results.

INDUSTRIAL APPLICABILITY According to the present invention, it is possible to provide a light-emitting device with excellent external quantum efficiency and a polymer compound useful for the production thereof.

Claims (13)

A light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
the first organic layer is a light- emitting layer containing a polymer compound (TP),
The second organic layer is a layer containing a crosslinked material of a crosslinkable material and provided between the anode and the first organic layer,
One low-molecular compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less as the polymer compound (TP) Including a structural unit containing a group excluding the above hydrogen atoms,
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from the group represented by formula (XL-1) and the group represented by formula (XL-17), or formula (XL-1 ) and a group represented by the formula (XL-17), a polymer compound comprising a crosslinked structural unit having at least one crosslinked group ,
The structural unit containing a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (T) is a structural unit represented by formula (2C), a structural unit represented by formula (3C), or a structural unit represented by formula (4C) ) is a structural unit represented by the light-emitting element.

[In the formula, *1 represents a binding position. These cross-linking groups may have substituents. ]

[In the formula,
T ^1C represents a group obtained by removing one hydrogen atom from the low molecular weight compound (T).
L ^d and L ^e each independently represent an oxygen atom, a sulfur atom, —N(R ^A )—, —C(R ^B ) ₂ —, —C(R ^B )=C(R ^B )—, —C ≡C— represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. RA ^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. RB ^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 RB 's 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 multiple L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more and 10 or less. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T2C represents a group obtained by removing two hydrogen ^atoms from the low-molecular-weight compound (T). ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T3C represents a group obtained by removing three hydrogen ^atoms from the low-molecular-weight compound (T). ] A light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
the first organic layer is a light- emitting layer containing a polymer compound (TP),
The second organic layer is a layer containing a crosslinked material of a crosslinkable material and provided between the anode and the first organic layer,
One low-molecular compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less as the polymer compound (TP) Including a structural unit containing a group excluding the above hydrogen atoms,
The cross-linking material is a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from the cross-linking group A, and the cross-linking structural unit is a structural unit represented by formula (2). or a structural unit represented by formula (2′) ,
The structural unit containing a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (T) is a structural unit represented by formula (2C), a structural unit represented by formula (3C), or a structural unit represented by formula (4C) ) is a structural unit represented by the light-emitting element.
<Crosslinking group A group>

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When multiple R ^XL are present, they may be the same or different, and when multiple n ^XL are present, they may be the same or different. *1 represents the binding position. These cross-linking groups may have substituents. ]

[In the formula,
nA represents an integer of 0 to 5, n represents 1 or 2; When multiple nAs are present, they may be the same or different.
Ar ³ represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.
L ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(
R′)—represents a group, an oxygen atom or a sulfur atom, and these groups may have a substituent. R' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^A are present, they may be the same or different.
X represents a cross-linking group selected from the cross-linking group A group. When there are multiple X's, they may be the same or different. ]

[In the formula,
mA represents an integer of 0 to 5, m represents an integer of 1 to 4, and c represents 0 or 1. When multiple mA are present, they may be the same or different.
Ar ⁵ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent.
Ar ⁴ and Ar ⁶ each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent.
Ar ⁴ , Ar ⁵ and Ar ⁶ are each bonded to a group other than the group bonded to the nitrogen atom to which the group is bonded, directly or through an oxygen atom or a sulfur atom to form a ring You may have
K ^A is an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, -N(
R′)—represents a group, an oxygen atom or a sulfur atom, and these groups may have a substituent. R' has the same meaning as above. When multiple K ^A are present, they may be the same or different.
X' represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group selected from the bridging group A group, and these groups may have a substituent. . When multiple X' are present, they may be the same or different. However, at least one X' is a cross-linking group selected from the cross-linking group A. ]

[In the formula,
T ^1C represents a group obtained by removing one hydrogen atom from the low molecular weight compound (T).
L ^d and L ^e each independently represent an oxygen atom, a sulfur atom, —N(R ^A )—, —C(R ^B ) ₂ —, —C(R ^B )=C(R ^B )—, —C ≡C— represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. RA ^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. RB ^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 RB 's 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 multiple L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more and 10 or less. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T2C represents a group obtained by removing two hydrogen ^atoms from the low-molecular-weight compound (T). ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T3C represents a group obtained by removing three hydrogen ^atoms from the low-molecular-weight compound (T). ] A light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
the first organic layer is a light- emitting layer containing a polymer compound (TP),
The second organic layer is a layer containing a crosslinked material of a crosslinkable material and provided between the anode and the first organic layer,
One low-molecular compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less as the polymer compound (TP) Including a structural unit containing a group excluding the above hydrogen atoms,
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from the cross-linking group A, and the low-molecular-weight compound is a low-molecular-weight compound represented by formula (3) ,
The structural unit containing a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (T) is a structural unit represented by formula (2C), a structural unit represented by formula (3C), or a structural unit represented by formula (4C) ) is a structural unit represented by the light-emitting element.
<Crosslinking group A group>

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When multiple R ^XL are present, they may be the same or different, and when multiple n ^XL are present, they may be the same or different. *1 represents the binding position. These cross-linking groups may have substituents. ]

[In the formula,
m ^B1 and m ^B2 each independently represent an integer of 0 or more and 10 or less. m ^B3 represents an integer of 0 or more and 5 or less. A plurality of m ^B1 may be the same or different. When multiple ^mB3 are present, they may be the same or different.
Ar ⁷ represents an aromatic hydrocarbon group, a heterocyclic group, or a group in which an aromatic hydrocarbon ring and a heterocyclic ring are directly bonded, and these groups may have a substituent. When multiple Ar ⁷ are present, they may be the same or different.
L ^B1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R''')-, an oxygen atom or a sulfur atom, and these groups are substituents may have R''' represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple L ^B1 are present, they may be the same or different.
X'' represents a bridging group, a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group selected from the bridging group A group, and these groups may have a substituent. good. Multiple X'' may be the same or different. However, at least one of the plurality of X'' is a cross-linking group selected from the cross-linking group A. ]

[In the formula,
T ^1C represents a group obtained by removing one hydrogen atom from the low molecular weight compound (T).
L ^d and L ^e each independently represent an oxygen atom, a sulfur atom, —N(R ^A )—, —C(R ^B ) ₂ —, —C(R ^B )=C(R ^B )—, —C ≡C— represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. RA ^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. RB ^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 RB 's 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 multiple L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more and 10 or less. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T2C represents a group obtained by removing two hydrogen ^atoms from the low-molecular-weight compound (T). ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
T3C represents a group obtained by removing three hydrogen ^atoms from the low-molecular-weight compound (T). ] A light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
the first organic layer is a light- emitting layer containing a polymer compound (TP),
The second organic layer is a layer containing a crosslinked material of a crosslinkable material and provided between the anode and the first organic layer,
One low-molecular compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less as the polymer compound (TP) Including a structural unit containing a group excluding the above hydrogen atoms and a structural unit represented by formula (Y),
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from Group A, or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from Group A. The above-mentioned light-emitting device.
<Crosslinking group A group>

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When multiple R ^XL are present, they may be the same or different, and when multiple n ^XL are present, they may be the same or different. *1 represents the binding position. These cross-linking groups may have substituents. ]

[In the formula, Ar ^Y1 represents an arylene group which may have a substituent. ] A light emitting device having an anode, a cathode, a first organic layer provided between the anode and the cathode, and a second organic layer provided between the anode and the cathode,
The first organic layer is a layer containing a polymer compound (TP) and a fluorescent compound as a light-emitting material,
The second organic layer is a layer containing a crosslinked material of a crosslinkable material and provided between the anode and the first organic layer,
One low-molecular compound (T) in which the absolute value of the difference between the energy level of the lowest triplet excited state and the energy level of the lowest singlet excited state is 0.5 eV or less as the polymer compound (TP) Including a structural unit containing a group excluding the above hydrogen atoms,
The cross-linking material is a low-molecular-weight compound having at least one cross-linking group selected from Group A, or a polymer compound containing a cross-linking structural unit having at least one cross-linking group selected from Group A. The above-mentioned light-emitting device.
<Crosslinking group A group>

[In the formula, R ^XL represents a methylene group, an oxygen atom or a sulfur atom, and n ^XL represents an integer of 0 to 5. When multiple R ^XL are present, they may be the same or different, and when multiple n ^XL are present, they may be the same or different. *1 represents the binding position. These cross-linking groups may have substituents. ] The structural unit containing a group obtained by removing one or more hydrogen atoms from the low-molecular-weight compound (T) is a structural unit represented by formula (1C), a structural unit represented by formula (2C), or a structural unit represented by formula (3C). ) or a structural unit represented by formula (4C), the light-emitting device according to claim 4 or 5 .

[In the formula,
T ^1C represents a group obtained by removing one hydrogen atom from the low molecular weight compound (T).
L ^C is an oxygen atom, a sulfur atom, -N(R ^A )-, -C(R ^B ) ₂ -, -C(R ^B )=C(R ^B )-, -C≡C-, an arylene group or It represents a divalent heterocyclic group, and these groups may have a substituent. ^RA 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. ^RB 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 RB's 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 multiple L ^C are present, they may be the same or different.
n ^c1 represents an integer of 0 or more and 10 or less. ]

[In the formula,
T ^1C has the same meaning as above.
L ^d and L ^e each independently represent an oxygen atom, a sulfur atom, —N(R ^A )—, —C(R ^B ) ₂ —, —C(R ^B )=C(R ^B )—, —C ≡C— represents an arylene group or a divalent heterocyclic group, and these groups may have a substituent. ^RA and ^RB have the same meaning as above. When multiple L ^d and L ^e are present, they may be the same or different.
n ^d1 and n ^e1 each independently represent an integer of 0 or more and 10 or less. A plurality of n ^d1 may be the same or different.
Ar ^1M represents an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent. ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
^T2C represents a group obtained by removing two hydrogen atoms from the low-molecular-weight compound (T). ]

[In the formula,
L ^d and n ^d1 have the same meanings as above.
^T3C represents a group obtained by removing three hydrogen atoms from the low-molecular-weight compound (T). ] The light-emitting device according to claim 4, wherein the structural unit represented by the formula (Y) is a structural unit represented by the formula (Y-1), the formula (Y-2), or the formula (Y-3). .

[In the formula,
R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent. A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
However, at least one R ^Y1 is not a hydrogen atom. ]

[In the formula,
^RY1 has the same meaning as above.
X ^Y1 represents a group represented by -C(R ^Y2 ) ₂ -, -C(R ^Y2 )=C(R ^Y2 )- or -C(R ^Y2 ) ₂ -C(R ^Y2 ) ₂ -. ^RY2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or an aryl group, and these groups may have a substituent. A plurality of ^RY2 may be the same or different, and the ^RY2 may be bonded to each other to form a ring together with the carbon atoms to which they are bonded.
However, at least one R ^Y1 is not a hydrogen atom. ]

[In the formula,
R ^Y1 and X ^Y1 have the same meaning as above.
However, at least one R ^Y1 is not a hydrogen atom. ] 8. The light-emitting device according to claim 1, wherein the low-molecular-weight compound (T) has an oscillator strength of 0.0001 or more and 1 or less. The light-emitting device according to any one of claims 1 to 8, wherein the low-molecular compound (T) is a low-molecular compound represented by formula (T-1).

[In the formula,
n ^T1 represents an integer of 0 or more and 5 or less. When multiple ^nT1 are present, they may be the same or different.
Ar ^T1 represents a substituted amino group or a monovalent heterocyclic group, and these groups may have a substituent. When Ar 2 ^T1 is present in plurality, they may be the same or different and may be directly bonded or bonded via a divalent group to form a ring. provided that at least one of Ar ^{1 T1} is a substituted amino group or a group containing a nitrogen atom having no double bond in the ring and represented by =N-, a boron atom, -C A group represented by (=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, and formula (P):

It is a monovalent heterocyclic group that does not contain a group represented by in the ring. Z ^T1 represents an oxygen atom, a sulfur atom or a group represented by =NR ^ZT1 . R ^ZT1 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.
L ^T1 represents an alkylene group, a cycloalkylene group, an arylene group, a divalent heterocyclic group, a group represented by -N(R ^T1 ')-, an oxygen atom or a sulfur atom, and these groups are substituents. may have. R ^T1 ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When multiple ^LT1 are present, they may be the same or different, and may be directly bonded or bonded via a divalent group to form a ring.
Ar ^T2 is a boron atom, a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, a group represented by -S(=O) ₂ -, the above formula A group represented by (P), an aromatic hydrocarbon group having an electron-withdrawing group, a heterocyclic group containing a boron atom in the ring, or a heterocyclic ring containing a group represented by =N- in the ring groups, and these groups may have a substituent.
n ^T2 represents an integer of 1 or more and 15 or less. provided that n ^T2 is 3 when Ar 2 ^T2 is a boron atom or a group represented by the formula (P). When Ar ^T2 is a group represented by -C(=Z ^T1 )-, a group represented by -S(=O)-, or a group represented by -S(=O) ₂ -, n ^T2 is two.
Ar ^T1 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T2 and L ^T1 may be directly bonded or bonded via a divalent group to form a ring. Ar ^T1 and Ar ^T2 may be directly bonded or bonded via a divalent group to form a ring. ] 6. The method according to claim 5, wherein the first organic layer further contains at least one selected from the group consisting of a host material, a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, and an antioxidant. The described light-emitting device. wherein the first organic layer further contains at least one selected from the group consisting of a host material, a hole-transporting material, a hole-injecting material, an electron-transporting material, an electron-injecting material, a light-emitting material, and an antioxidant; Item 5. The light emitting device according to any one of Items 1 to 4. 12. The light-emitting device according to claim 11, wherein the first organic layer contains a phosphorescent compound represented by formula Ir-1 as the light-emitting material.

[In the formula,
R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 and R ^D8 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryl It represents an oxy group, a monovalent heterocyclic group or a halogen atom, and these groups may have a substituent. When a plurality of R ^D1 , R ^D2 , R ^D3 , R ^D4 , R ^D5 , R ^D6 , R ^D7 and R ^D8 are present, they may be the same or different.
-A ^D1 ---A ^D2 - represents an anionic bidentate ligand, A ^D1 and A ^D2 each independently represents a carbon atom, an oxygen atom or a nitrogen atom bonded to an iridium atom; may be atoms constituting a ring. When there are a plurality of -A ^D1 ---A ^D2 -, they may be the same or different.
n _D1 represents 1, 2 or 3;
n _D2 represents 1 or 2; ] 13. The light-emitting device according to claim 1, wherein said first organic layer and said second organic layer are adjacent to each other.