JP2013241579A - Polymer compound and light-emitting element using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymer compound useful for producing a light-emitting element having an excellent brightness life.SOLUTION: A polymer compound includes a structural unit of formula (1-1) and a structural unit of a hydrocarbon with a particular structure (wherein R-R, Rand Rare hydrogen atoms or the like; Rand Rare aryl groups or the like; Arand Arare arylene groups or the like, ring A is an aromatic hydrocarbon ring or the like; Y is -C(R)- or the like; and Ris an alkyl group or the like).

Description

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

  As a light-emitting material for use in a light-emitting element, for example, a polymer compound containing a structural unit represented by the following formula derived from arylamine (Patent Document 1) and a structural unit represented by the following formula derived from fluorene A high molecular compound (Patent Document 2) containing benzene has been studied.

JP 2004-143419 A JP-T-2004-527628

  However, when the above polymer compound is used for manufacturing a light emitting device, the luminance life of the obtained light emitting device is not sufficient.

  Then, an object of this invention is to provide a high molecular compound useful for manufacture of the light emitting element which is excellent in a luminance lifetime. Another object of the present invention is to provide a composition, an organic thin film, an insolubilized organic thin film, and a light emitting device containing the polymer compound. Another object of the present invention is to provide a raw material compound for a polymer compound.

  The present invention provides the following polymer compound, a composition containing the polymer compound, an organic thin film, an insolubilized organic thin film and a light emitting device, and a raw material compound of the polymer compound.

[1] At least one selected from the group consisting of a structural unit represented by the following formula (1-1), a structural unit represented by the following formula (1-2), and a structural unit represented by the following formula (1-3) A structural unit of
At least one structural unit selected from the group consisting of a structural unit represented by the following formula (2), a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4);
A polymer compound containing

［式中、
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^ｘ１、Ｒ^ｘ２、Ｒ^ｙ１およびＲ^ｙ２は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。
Ｒ^ＡおよびＲ^Bは、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ａｒ^１およびＡｒ^２は、それぞれ独立に、非置換もしくは置換のアリーレン基または非置換もしくは置換の２価の複素環基を示す。
Ａｒ^１とＲ^Ａは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよく、Ａｒ^２とＲ^Bは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよい。
環Aは、非置換もしくは置換の芳香族炭化水素環または非置換もしくは置換の芳香族複素環を示す。
Xは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Yは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Ｒ^aは、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。Ｒ^aが複数存在するとき、それらは同一でも異なっていてもよく、互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。]

［式中、
aおよびbは、それぞれ独立に、０〜３の整数を示す。
Ｒ⁴およびＲ⁵は、それぞれ独立に、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。
Ｒ^６は、水素原子、非置換もしくは置換のアルキル基または非置換もしくは置換のアルコキシ基を示す。
Ｒ^７は、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。]

［式中、
cおよびdは、それぞれ独立に、０〜３の整数を示す。
Ｒ^８およびＲ^９は、それぞれ独立に、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。
Ｒ^１０、Ｒ^１１、Ｒ^１２およびＲ^１３は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。但し、Ｒ^１０およびＲ^１２、Ｒ^１１およびＲ^１３、Ｒ^１０およびＲ^１１、並びに、Ｒ^１２およびＲ^１３からなる群から選ばれる少なくとも一組は、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構造を形成する。]

［式中、
Ｒ^１４およびＲ^１５は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。但し、Ｒ^１４およびＲ^１５からなる群から選ばれる少なくとも一方は、水素原子以外の基を示す］［２］ 前記式（１−１）で示される構成単位、前記式（１−２）で示される構成単位および前記式（１−３）で示される構成単位が、それぞれ、下記式（１−１−Ａ）で示される構成単位、下記式（１−２−Ａ）で示される構成単位および下記式（１−３−Ａ）で示される構成単位である、［１］に記載の高分子化合物。

［式中、
Ｘ、Ｙ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^ｘ１、Ｒ^ｘ２、Ｒ^ｙ１、Ｒ^ｙ２、Ｒ^Ａ、Ｒ^Ｂ、Ａｒ^１およびＡｒ^２は、前記と同義である。
Ｒ^２３、Ｒ^２４およびＲ^２５は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示し、Ｒ^２４とＲ^２５は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。］
［３］ 前記式（１−１−Ａ）で示される構成単位および前記式（１−２−Ａ）で示される構成単位が、それぞれ、下記式（１−１−Ｂ）で示される構成単位および下記式（１−２−Ｂ）で示される構成単位である、［２］に記載の高分子化合物。

［式中、
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^ｘ１、Ｒ^ｘ２、Ｒ^ｙ１、Ｒ^ｙ２、Ｒ^２３、Ｒ^２４、^２５、Ｒ^Ａ、Ｒ^Ｂ、Ａｒ^１およびＡｒ^２は、前記と同義である。
Ｒ^２６、Ｒ^２７、Ｒ^２８およびＲ^２９は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の複素環基を示し、Ｒ^２６とＲ^２７は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよく、Ｒ^２８とＲ^２９は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。］
［４］ 前記式（３）で示される構成単位が、下記式（３-Ａ）で示される構成単位である、［１］〜［３］のいずれか一つに記載の高分子化合物。

［式中、
c、d、Ｒ^８およびＲ^９は、前記と同義である。
ｎ^１およびｎ^２は、それぞれ独立に、１〜５の整数を示す。
Ｒ^３０、Ｒ^３１、Ｒ^３２およびＲ^３３は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。Ｒ^３０、Ｒ^３１、Ｒ^３２およびＲ^３３がそれぞれ複数存在するとき、複数存在するＲ^３０、Ｒ^３１、Ｒ^３２およびＲ^３３は互いに同一でも異なっていてもよく、Ｒ^３０、Ｒ^３１、Ｒ^３２およびＲ^３３のうち隣接する基同士は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。]
［５］ 前記式（１−１）で示される構成単位、前記式（１−２）で示される構成単位および前記式（１−３）で示される構成単位からなる群から選ばれる少なくとも１種の構成単位と、
前記式（２）で示される構成単位と、前記式（４）で示される構成単位と、
を含む、［１］〜［３］のいずれか一つに記載の高分子化合物。
［６］ 更に、下記式（５）で示される構成単位（前記式（２）で示される構成単位、前記式（３）で示される構成単位および前記式（４）で示される構成単位とは異なる。）を含む、［１］〜［５］のいずれか一つに記載の高分子化合物。

［式中、
Ａｒ^３は非置換もしくは置換のアリーレン基または非置換もしくは置換の２価の複素環基を示す。］
［７］ 前記式（５）で示される構成単位が、非置換もしくは置換のフルオレンジイル基である、［６］に記載の高分子化合物。
［８］ 更に、下記式（６）で示される構成単位（前記式（１−１）で示される構成単位、前記式（１−２）で示される構成単位、前記式（１−３）で示される構成単位および前記式（５）で示される構成単位とは異なる。）を含む、［１］〜［７］のいずれか一つに記載の高分子化合物

［式中、
a^１およびa^２は、それぞれ独立に、０または１を示す。
Ａｒ^４およびＡｒ^６は、それぞれ独立に、非置換もしくは置換のアリーレン基または非置換もしくは置換の２価の複素環基を示す。
Ａｒ^５およびＡｒ^７は、それぞれ独立に、非置換もしくは置換のアリーレン基、非置換もしくは置換の２価の複素環基、または、アリーレン基および２価の複素環基から選ばれる同一もしくは異なる２以上の基が連結した２価の基（当該２価の基は、置換基を有していてもよい。）を示す。
Ｒ^C、Ｒ^DおよびＲ^Eは、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ａｒ^４、Ａｒ^５、Ａｒ^６およびＡｒ^７はそれぞれ、当該基が結合している窒素原子に結合している当該基以外の基と互いに連結して環構造を形成していてもよい。］
［９］ 前記式（６）で示される構成単位が、下記式（７）で示される構成単位である、［８］に記載の高分子化合物。

［式中、
Ｒ^Fは、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ｚは、単結合、酸素原子、硫黄原子または−Ｃ（Ｒ^b）_２−を示す。Ｒ^bは、水素原子、非置換もしくは置換のアルキル基または非置換もしくは置換のアリール基を示す。２個存在するＲ^ｂは、同一でも異なっていてもよく、互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。］
［１０］ 高分子化合物に含まれる全構成単位に対する、前記式（１−１）で示される構成単位、前記式（１−２）で示される構成単位および前記式（１−３）で示される構成単位の合計の割合が、０．１〜７０モル％である、［１］〜［９］のいずれか一つに記載の高分子化合物。
［１１］ 下記式（１−１）で示される構成単位、下記式（１−２）で示される構成単位および下記式（１−３）で示される構成単位からなる群から選ばれる少なくとも１種の構成単位と、下記式（８）で示される構成単位と、を含む高分子化合物。

［式中、
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^ｘ１、Ｒ^ｘ２、Ｒ^ｙ１およびＲ^ｙ２は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。
Ｒ^ＡおよびＲ^Bは、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ａｒ^１およびＡｒ^２は、それぞれ独立に、非置換もしくは置換のアリーレン基または非置換もしくは置換の２価の複素環基を示す。
Ａｒ^１とＲ^Ａは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよく、Ａｒ^２とＲ^Bは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよい。
環Aは、非置換もしくは置換の芳香族炭化水素環または非置換もしくは置換の芳香族複素環を示す。
Xは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Yは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Ｒ^aは、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。Ｒ^aが複数存在するとき、それらは同一でも異なっていてもよく、互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。]

［式中、
ｎａは０〜３の整数を示し、ｎｂは０〜１２の整数を示し、ｎＡは０または１であり、ｎは１または２を示す。
Ａｒ^８は、非置換もしくは置換のアリーレン基、非置換もしくは置換の２価の芳香族アミンまたは非置換もしくは置換の２価の複素環基を示す。
Ｌ^ａおよびＬ^ｂは、それぞれ独立に、直接結合、非置換もしくは置換のアルキレン基または非置換もしくは置換のフェニレン基を示す。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。Ｌ^ｂが複数存在する場合、それらは同一でも異なっていてもよい。
Ｌ^Ａは酸素原子または硫黄原子を示す。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１価の架橋性基を示す。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。］
［１２］ 下記式（１−１−Ｍ）、（１−２−Ｍ）または（１−３−Ｍ）で示される化合物。

［式中、
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^ｘ１、Ｒ^ｘ２、Ｒ^ｙ１およびＲ^ｙ２は、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。
Ｒ^ＡおよびＲ^Bは、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ａｒ^１およびＡｒ^２は、それぞれ独立に、非置換もしくは置換のアリーレン基または非置換もしくは置換の２価の複素環基を示す。
Ａｒ^１とＲ^Ａは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよく、Ａｒ^２とＲ^Bは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよい。
環Aは、非置換もしくは置換の芳香族炭化水素環または非置換もしくは置換の芳香族複素環を示す。
Xは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Yは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Ｒ^aは、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。Ｒ^aが複数存在するとき、それらは同一でも異なっていてもよく、互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。
Ｚ^１およびＺ^２は、それぞれ独立に、下記置換基群から選ばれる基を示す。
＜置換基群＞
水素原子、塩素原子、臭素原子、ヨウ素原子、
−Ｏ−Ｓ（＝Ｏ）_２Ｒ^４１（Ｒ^４１は、非置換もしくは置換のアルキル基または非置換もしくは置換のアリール基を示す。）で示される基、
−Ｂ（ＯＲ^４２）_２（Ｒ^４２は水素原子または非置換もしくは置換のアルキル基を示し、複数存在するＲ^４２は互いに同一でも異なっていてもよく、互いに連結して、それぞれが結合する酸素原子とともに環構造を形成していてもよい。）で示される基、
−ＢＦ_４Ｑ^１（Ｑ^１は、Ｌｉ^＋、Ｎａ^＋、Ｋ^＋、Ｒｂ^＋およびＣｓ^＋からなる群より選ばれる１価の陽イオンを示す。）で示される基、
−ＭｇＹ^１（Ｙ^１は、塩素原子、臭素原子またはヨウ素原子を示す。）で示される基、 −ＺｎＹ^２（Ｙ^２は、塩素原子、臭素原子またはヨウ素原子を示す。）で示される基、および、
−Ｓｎ（Ｒ^４３）_３（Ｒ^４３は水素原子または非置換もしくは置換のアルキル基を示し、複数存在するＲ^４３は互いに同一でも異なっていてもよく、互いに連結して、それぞれが結合するスズ原子とともに環構造を形成していてもよい。）で示される基。］
［１３］ ［１］〜［１１］のいずれか一つに記載の高分子化合物と、
正孔輸送材料、電子輸送材料および発光材料からなる群より選ばれる少なくとも一種の材料と、を含有する組成物。
［１４］ ［１］〜［１１］のいずれか一つに記載の高分子化合物を含有する有機薄膜。
［１５］ ［１１］に記載の高分子化合物を含有する有機薄膜を、加熱することで溶媒に対して不溶化させた、不溶化有機薄膜。
［１６］ ［１４］に記載の有機薄膜または［１５］に記載の不溶化有機薄膜を備える発光素子。

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted An aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocycle.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]

[Where:
a and b each independently represent an integer of 0 to 3.
R ⁴ and R ⁵ are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted 1 A valent heterocyclic group is shown.
R ⁶ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group.
R ⁷ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group. ]

[Where:
c and d each independently represent an integer of 0 to 3.
R ⁸ and R ⁹ are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted 1 A valent heterocyclic group is shown.
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown. Provided that at least one pair selected from the group consisting of R ¹⁰ and R ¹² , R ¹¹ and R ¹³ , R ¹⁰ and R ¹¹ , and R ¹² and R ¹³ is bonded to each other, together with the carbon atom to which each is bonded. Form a ring structure. ]

[Where:
R ¹⁴ and R ¹⁵ each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or A substituted monovalent heterocyclic group is shown. However, at least one selected from the group consisting of R ¹⁴ and R ¹⁵ represents a group other than a hydrogen atom.] [2] A structural unit represented by the formula (1-1), represented by the formula (1-2) The structural unit represented by the following formula (1-1-A), the structural unit represented by the following formula (1-2-A), and the structural unit represented by the formula (1-3) The polymer compound according to [1], which is a structural unit represented by the following formula (1-3-A).

[Where:
X, Y, R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.
R ²³ , R ²⁴ and R ²⁵ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group or R represents an unsubstituted or substituted monovalent heterocyclic group, and R ²⁴ and R ²⁵ may be connected to each other to form a ring structure together with the carbon atom to which each is bonded. ]
[3] The structural unit represented by the formula (1-1-A) and the structural unit represented by the formula (1-2-A) are each a structural unit represented by the following formula (1-1-B). And the polymer compound according to [2], which is a structural unit represented by the following formula (1-2-B):

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ²³ , R ²⁴ , ²⁵ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl Represents an oxy group or an unsubstituted or substituted heterocyclic group, R ²⁶ and R ²⁷ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded, and R ²⁸ and R ²⁹ are linked to each other; In addition, a ring structure may be formed together with the carbon atoms to which each is bonded. ]
[4] The polymer compound according to any one of [1] to [3], wherein the structural unit represented by the formula (3) is a structural unit represented by the following formula (3-A).

[Where:
c, d, R ⁸ and R ⁹ are as defined above.
n ¹ and ^{n 2} each independently represent an integer of 1 to 5.
R ³⁰ , R ³¹ , R ³² and R ³³ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown. When there are a plurality of R ³⁰ , R ³¹ , R ³² and R ³³ , the plurality of R ³⁰ , R ³¹ , R ³² and R ³³ may be the same as or different from each other. R ³⁰ , R ³¹ , R ³² And adjacent groups of R ³³ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded. ]
[5] At least one selected from the group consisting of the structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3). A structural unit of
A structural unit represented by the formula (2), a structural unit represented by the formula (4), and
The polymer compound according to any one of [1] to [3].
[6] Further, the structural unit represented by the following formula (5) (the structural unit represented by the formula (2), the structural unit represented by the formula (3), and the structural unit represented by the formula (4) The polymer compound according to any one of [1] to [5].

[Where:
Ar ³ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group. ]
[7] The polymer compound according to [6], wherein the structural unit represented by the formula (5) is an unsubstituted or substituted fluorenediyl group.
[8] Furthermore, the structural unit represented by the following formula (6) (the structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the formula (1-3) And a polymer compound according to any one of [1] to [7], which is different from the structural unit represented by formula (5).

[Where:
a ¹ and a ² each independently represent 0 or 1.
Ar ⁴ and Ar ⁶ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ⁵ and Ar ⁷ are each independently an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or the same or different two or more selected from an arylene group and a divalent heterocyclic group The bivalent group which this group connected (The said bivalent group may have a substituent.) Is shown.
R ^C , R ^D and R ^E each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ may each be linked to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring structure. ]
[9] The polymer compound according to [8], wherein the structural unit represented by the formula (6) is a structural unit represented by the following formula (7).

[Where:
R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^{b s} may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]
[10] The structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural formula (1-3) with respect to all the structural units contained in the polymer compound. The polymer compound according to any one of [1] to [9], wherein the total proportion of the structural units is 0.1 to 70 mol%.
[11] At least one selected from the group consisting of a structural unit represented by the following formula (1-1), a structural unit represented by the following formula (1-2), and a structural unit represented by the following formula (1-3). And a polymer compound comprising the structural unit represented by the following formula (8).

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted An aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocycle.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]

[Where:
na represents an integer of 0 to 3, nb represents an integer of 0 to 12, nA represents 0 or 1, and n represents 1 or 2.
Ar ⁸ represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent aromatic amine, or an unsubstituted or substituted divalent heterocyclic group.
L ^a and L ^b each independently represent a direct bond, an unsubstituted or substituted alkylene group, or an unsubstituted or substituted phenylene group. When ^a plurality of ^La are present, they may be the same or different. When a plurality of ^Lb are present, they may be the same or different.
L ^A represents an oxygen atom or a sulfur atom. When a plurality of ^LA are present, they may be the same or different.
X ′ represents a monovalent crosslinkable group. When a plurality of X ′ are present, they may be the same or different. ]
[12] A compound represented by the following formula (1-1-M), (1-2-M) or (1-3-M).

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted An aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocycle.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.
Z ¹ and Z ² each independently represent a group selected from the following substituent group.
<Substituent group>
Hydrogen atom, chlorine atom, bromine atom, iodine atom,
A group represented by —O—S (═O) ₂ R ⁴¹ (wherein R ⁴¹ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group),
—B (OR ⁴² ) ₂ (R ⁴² represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ⁴² may be the same as or different from each other, and are bonded to each other to bind to each other. And may form a ring structure together with the group
A group represented by -BF ₄ Q ¹ (Q ¹ represents a monovalent cation selected from the group consisting of Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ and Cs ⁺ );
A group represented by —MgY ¹ (Y ¹ represents a chlorine atom, a bromine atom or an iodine atom); a group represented by —ZnY ² (Y ² represents a chlorine atom, a bromine atom or an iodine atom); and,
—Sn (R ⁴³ ) ₃ (R ⁴³ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ⁴³ may be the same as or different from each other, and are linked to each other, and are bonded to each other. And may form a ring structure together with the above group). ]
[13] The polymer compound according to any one of [1] to [11],
A composition containing at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.
[14] An organic thin film containing the polymer compound according to any one of [1] to [11].
[15] An insolubilized organic thin film obtained by heating the organic thin film containing the polymer compound according to [11] to a solvent by heating.
[16] A light emitting device comprising the organic thin film according to [14] or the insolubilized organic thin film according to [15].

  ADVANTAGE OF THE INVENTION According to this invention, the high molecular compound useful for manufacture of the light emitting element which is excellent in a luminance lifetime can be provided. The present invention can also provide a composition, an organic thin film, an insolubilized organic thin film, and a light-emitting element containing the polymer compound. The present invention can further provide a raw material compound of a polymer compound.

  Hereinafter, terms commonly used in this specification will be described with examples as necessary.

  “Me” represents a methyl group, “Et” represents an ethyl group, “Ph” represents a phenyl group, and “t-Bu” and “tBu” represent a tert-butyl group.

  The “structural unit” means a unit structure existing in one or more polymer compounds. The “structural unit” is preferably contained in the polymer compound as a “repeating unit” (that is, a unit structure existing two or more in the polymer compound).

  The term “unsubstituted or substituted” means that the functional group described immediately after this term may have a substituent. For example, “an unsubstituted or substituted alkyl group” means “an unsubstituted alkyl group or an alkyl group having a substituent”.

  The “n-valent heterocyclic group” (n is an integer of 1 or more) constitutes a ring of a heterocyclic compound (preferably an aromatic heterocyclic compound having aromaticity). It means the remaining atomic group obtained by removing n hydrogen atoms from the carbon atom to be formed. “Heterocyclic compound” is an organic compound having a cyclic structure in which not only carbon atoms but also heteroatoms such as oxygen atoms, sulfur atoms, nitrogen atoms, phosphorus atoms and boron atoms are included in the ring. This means a compound contained in the ring. The “arylene group” means an atomic group remaining after removing two hydrogen atoms from a carbon atom constituting an aromatic hydrocarbon ring, and includes a group having a condensed ring. In addition, a group in which two or more rings selected from independent benzene rings and condensed rings are directly bonded is not included. “Aryl group” means a remaining atomic group obtained by removing one hydrogen atom from a carbon atom constituting an aromatic hydrocarbon ring, and is selected from a group having a condensed ring, an independent benzene ring and a condensed ring. Includes groups in which two or more are directly bonded.

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

[Polymer compound]
Hereinafter, the polymer compound of the present invention will be described.

  The polymer compound of the present invention is a group consisting of a structural unit represented by the following formula (1-1), a structural unit represented by the following formula (1-2), and a structural unit represented by the following formula (1-3). 1 selected from the group consisting of at least one structural unit selected from: a structural unit represented by the following formula (2), a structural unit represented by the following formula (3), and a structural unit represented by the following formula (4): And more than one species of structural unit.

(Structural Unit Represented by Formula (1-1), Structural Unit Represented by Formula (1-2), and Structural Unit Represented by Formula (1-3))

In formula (1-1) to formula (1-3), R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, unsubstituted or substituted alkyl A group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group;

R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are more excellent in luminance life of the light-emitting element obtained when the polymer compound of this embodiment is used in the production of a light-emitting element. Therefore, a hydrogen atom, an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group is preferable, a hydrogen atom or an unsubstituted or substituted alkyl group is more preferable, and a hydrogen atom is more preferable.

The unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 may be linear, branched or cyclic, and linear alkyl The number of carbon atoms of the group does not include the number of carbon atoms of the substituent, and is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20. The number of carbon atoms of the branched alkyl group and the cyclic alkyl group is usually 3-50, preferably 3-30, more preferably 4-20, not including the number of carbon atoms of the substituent. .
Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isoamyl group, n-hexyl group, cyclohexyl group, Examples include n-heptyl group, cyclohexylmethyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, and 2-n-hexyl-decyl group.

The number of carbon atoms of the unsubstituted or substituted aryl group represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 does not include the number of carbon atoms of the substituent, and is usually 6 to 60 Preferably, it is 6-48, More preferably, it is 6-30.
As the aryl group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, Examples include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, and 4-phenylphenyl group.

The number of carbon atoms of the unsubstituted or substituted monovalent heterocyclic group represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 does not include the number of carbon atoms of the substituent. Usually, it is 2-60, Preferably it is 3-20.
Examples of the monovalent heterocyclic group include thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidyl group, quinolyl group, isoquinolyl group, pyrimidyl group, triazinyl group, and a hydrogen atom in these groups is an alkyl group, Examples thereof include a group substituted with an alkoxy group or the like. Of these, a thienyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a pyrimidyl group, and a triazinyl group are preferable.

The unsubstituted or substituted alkoxy group represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 may be linear, branched or cyclic. The number of carbon atoms of the linear alkoxy group does not include the number of carbon atoms of the substituent, and is usually 1 to 40, preferably 3 to 20, and more preferably 4 to 10. The number of carbon atoms of the branched alkoxy group and the cyclic alkoxy group does not include the number of carbon atoms of the substituent, and is usually 3 to 40, preferably 3 to 20, and more preferably 4 to 10. .
Examples of the alkoxy group include methoxy group, ethoxy group, n-propyloxy group, isopropyloxy group, n-butyloxy group, isobutyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, and cyclohexyl. Examples thereof include an oxy group, an n-heptyloxy group, an n-octyloxy group, a 2-ethylhexyloxy group, an n-nonyloxy group, an n-decyloxy group, a 3,7-dimethyloctyloxy group, and a lauryloxy group.

The number of carbon atoms of the unsubstituted or substituted aryloxy group represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6-48.
Examples of the aryloxy group include a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, and 1-pyrenyloxy group.

In formula (1), R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.

R ^A and R ^B are excellent in the stability of the polymer compound of the present embodiment, and when the polymer compound of the present embodiment is used for manufacturing a light emitting device, the luminance life obtained is more excellent. An unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group, preferably an unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent group. It is more preferably a heterocyclic group, and further preferably an unsubstituted or substituted aryl group.

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group represented by R ^A and R ^B are respectively R ¹ , R ² , R ^3. , R ^x1 , R ^x2 , R ^y1 and R ^y2 have the same definitions and examples as the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group.

As the unsubstituted or substituted aryl group represented by R ^A and R ^B , the solubility of the polymer compound of the present embodiment in an organic solvent and the heat resistance are improved in a well-balanced manner. A phenyl group).
Examples of the phenyl group substituted with an alkyl group include a 2,6-dimethyl-4-n-butylphenyl group, a 2,6-dimethyl-4-tert-butylphenyl group, and a 2,4,6-trimethylphenyl group. 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-n-butylphenyl group, 4-n-butylphenyl group, 4-tert-butylphenyl group, 3-n-hexylphenyl group 4-n-hexylphenyl group, 4-n-octylphenyl group, 3,5-dimethylphenyl group, 3-n-hexyl-5-methylphenyl group, 3,5-di-n-hexylphenyl group, etc. Can be mentioned.

In formula (1), Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ¹ and Ar ² does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 30, and more preferably 6 ~ 18.
Examples of the arylene group represented by Ar ¹ and Ar ² include a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 1,4-naphthalenediyl group, and a 1,5-naphthalenediyl group. 2,6-naphthalenediyl group, 2,7-naphthalenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group, 2,7-dihydrophenanthenediyl group, 5,12-naphthacenediyl group, 2,7-fluorenediyl group, 3,6-fluorenediyl group, 1,6-pyrenediyl group, 2,7-pyrenediyl group, 3,9-perylenediyl group, 3,10-perylenediyl group Group, 6,12-chrysenediyl group, 2,8-chrysenediyl group, 1,4-phenylene group, 2,7-fluorenediyl group, , 6-anthracene-diyl group, 9,10-anthracene-diyl group, 2,7-phenanthrenediyl group, 2,7-dihydro-phenanthrenediyl group, 1,6-pyrenediyl group.

The number of carbon atoms of the unsubstituted or substituted divalent heterocyclic group represented by Ar ¹ and Ar ² does not include the number of carbon atoms of the substituent, and is usually 2 to 60, preferably 3 to 30. More preferably, it is 3-15.
Examples of the divalent heterocyclic group represented by Ar ¹ and Ar ² include 2,5-thiophenediyl group, 2,5-pyrrolediyl group, 2,5-furandiyl group, 2,5-pyridinediyl group, 2 , 6-pyridinediyl group, 2,6-quinolinediyl group, 1,4-isoquinolinediyl group, 1,5-isoquinolinediyl group, 5,8-quinoxalinediyl group, 2,7-carbazolediyl group, 3,6- Carbazolediyl group, 3,7-phenoxazinediyl group, 3,7-phenothiazinediyl group, 2,8-phenothiazinediyl group, 4,6-phenothiazinediyl group, 2,1,3-benzothiadiazole-4,7- Examples thereof include a diyl group, a 2,7-dibenzofurandiyl group, a 2,7-dibenzothiophenediyl group, and a 2,7-dibenzosilolediyl group.

The groups represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ^A , R ^B , Ar ¹ and Ar ² may have a substituent. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. Examples thereof include a cyclic group and a cyano group, and an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferred.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

In formula (1), Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other and are bonded to each other. A ring structure may be formed together with the atoms.

“Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. “Optionally formed” means that Ar ¹ and R ^A (or Ar ² and R ^B ) are a single bond, or —O—, —S—, —C (═O) —, —C ( ═O) —O—, —N (R ²⁹ ) —, —C (═O) —N (R ²⁹ ) — or C (R ²⁹ ) ₂ — is bonded via a group (R ²⁹ is An unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group, and when there are a plurality of R ^{29 s} , they may be the same or different from each other), indicating that they may form a ring structure.

The definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ²⁹ are respectively R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2. The definition and examples are the same as those of the substituted or substituted alkyl group and the unsubstituted or substituted aryl group.

The formed ring structure may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or Examples thereof include a substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

  In formula (1), ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocyclic ring, and is preferably an unsubstituted or substituted aromatic hydrocarbon ring.

  Examples of the aromatic hydrocarbon ring represented by ring A include a benzene ring, a naphthalene ring, an anthracene ring, a pyrene ring, a phenanthrene ring, and a condensed form of these rings, and a benzene ring and a naphthalene ring are preferable. Is more preferable.

  Examples of the aromatic heterocyclic ring represented by the ring A include a thiophene ring, a furan ring, a pyrrole ring, a pyridine ring, and those obtained by condensing these rings.

Ring A may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted aryloxy group. , A halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

In the formula (1), X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S— or —OC (R ^a ) ₂ — is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.

^Ra is a hydrogen atom since the stability of the polymer compound of the present embodiment is improved and the obtained luminance lifetime is more excellent when the polymer compound of the present embodiment is used in the production of a light-emitting device. An unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group or an unsubstituted or substituted aryl group, preferably a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group It is more preferable.

Definition of an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted monovalent heterocyclic group represented by R ^a And examples are unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryls represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 , respectively. The definition and examples are the same as the group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group.

  The structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3) are used for manufacturing the light-emitting device. When used, the luminance life obtained is more excellent, and preferably, the structural unit represented by the following formula (1-1-A), the structural unit represented by the following formula (1-2-A), and the following formula, respectively. It is a structural unit represented by (1-3-A).

In the formula (2), X, Y, R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.

In formula (2), R ²³ , R ²⁴ and R ²⁵ each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or A substituted aryloxy group or an unsubstituted or substituted monovalent heterocyclic group, wherein R ²⁴ and R ²⁵ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded;

R ²³ , R ^24, and R ²⁵ are each a hydrogen atom, an unsubstituted or substituted alkyl group, because when the polymer compound of this embodiment is used for the production of a light-emitting device, the resulting light-emitting device has better luminance life. An unsubstituted or substituted aryl group is preferred, a hydrogen atom, an unsubstituted or substituted alkyl group is more preferred, and a hydrogen atom is still more preferred.

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group represented by R ²³ , R ^24, and R ²⁵ are R ¹ , R ² , respectively. , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are the same as the definition or examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted aryl group, unsubstituted or substituted monovalent heterocyclic group It is.

R ²⁴ and R ²⁵ are linked to each other, and the ring structure formed together with the carbon atoms to which they are bonded may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or Examples thereof include a substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

  The structural unit represented by the formula (1-1-A) and the structural unit represented by the formula (1-2-A) are luminance obtained when the polymer compound of the present embodiment is used for manufacturing a light emitting device. Since the lifetime is more excellent, each of them is preferably a structural unit represented by the following formula (1-1-B) or a structural unit represented by the following formula (1-2-B).

In formula (1-1-B) and formula (1-2-B), R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ²³ , R ²⁴ , R ²⁵ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.

In formula (1-1-B) and formula (1-2-B), R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, unsubstituted or A substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group or an unsubstituted or substituted monovalent heterocyclic group, wherein R ²⁶ and R ²⁷ are linked to each other and bonded to each other A ring structure may be formed with the carbon atoms to be bonded, and R ²⁸ and R ²⁹ may be linked to each other to form a ring structure with the carbon atoms to which they are bonded.

R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are the light emission obtained when the polymer compound of this embodiment is easy to produce and the polymer compound of this embodiment is used for the production of a light-emitting device. Since the luminance lifetime of the device is more excellent, a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted aryl group is preferable. It is more preferably a group or an unsubstituted or substituted aryl group, and further preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group.

The unsubstituted or substituted alkyl group represented by R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ may be linear, branched or cyclic, and the linear alkyl group usually has 1 to 1 carbon atoms. About 50, preferably 1-30, more preferably 1-20. The number of carbon atoms of the branched alkyl group and the cyclic alkyl group is usually about 3 to 50, preferably 3 to 30, and more preferably 4 to 20.
Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isoamyl group, n-hexyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyl-decyl group, and these And a group in which the hydrogen atom is substituted with an alkyl group, an aryl group, an alkoxy group, a fluorine atom, or the like, and a light-emitting device obtained when the polymer compound of this embodiment is used for the production of a light-emitting device In this case, an unsubstituted alkyl group is preferable, and a methyl group, an ethyl group, an n-propyl group, an n-butyl group, and an isobutyl group are preferable. N-pentyl group, isoamyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2- n-hexyl-decyl group is more preferable, methyl group, n-butyl group, isobutyl group, n-pentyl group, isoamyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n A -decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, and a 2-n-hexyl-decyl group are more preferable.

The number of carbon atoms of the unsubstituted or substituted aryl group represented by R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ does not include the number of carbon atoms of the substituent, and is preferably 6 to 60, more preferably 6 to 48, more preferably 6-30.
As the aryl group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups are alkyl groups, aryl groups, alkoxy Group, a group substituted with a fluorine atom, etc., and the solubility of the polymer compound of this embodiment in an organic solvent and the heat resistance are improved in a well-balanced manner, so that a phenyl group substituted with a phenyl group or an alkyl group It is preferable that

Examples of the phenyl group substituted with the alkyl group represented by R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ include 2,6-dimethyl-4-n-butylphenyl group, 2,6-dimethyl-4-tert- Butylphenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-n-butylphenyl group, 4-n-butylphenyl group, 4-tert-butylphenyl group, 3-n- Hexylphenyl group, 4-n-hexylphenyl group, 3-n-octylphenyl group, 4-n-octylphenyl group, 3,5-dimethylphenyl group, 3-n-hexyl-5-methylphenyl group, 3, 5-di-n-butylphenyl group, 3,5-di-tert-butylphenyl group, 3,5-di-n-hexylphenyl group, 3-n-hexylphenyl group, -n- hexyl phenyl group, 3-n-hexyl-5-methylphenyl group, 3,5-di -n- hexyl phenyl group is preferred.

Definitions and examples of the unsubstituted or substituted alkoxy group, unsubstituted or substituted aryloxy group and unsubstituted or substituted monovalent heterocyclic group represented by R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are respectively R ^a represents an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryloxy group, the same as the definitions and examples of the monovalent heterocyclic group unsubstituted or substituted.

R ²⁶ and R ²⁷ are connected to each other to form a ring structure formed with the carbon atoms to which they are bonded, and R ²⁸ and R ²⁹ are connected to each other to form a ring structure formed with the carbon atoms to which each is bonded. The substituent may have an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom. , Unsubstituted or substituted monovalent heterocyclic group, and cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

  A structural unit represented by formula (1-1) (may be a structural unit represented by formula (1-1-A) or formula (1-1-B)), represented by formula (1-2) Ratio of the structural unit (which may be the structural unit represented by formula (1-2A) or formula (1-2B)) and the structural unit represented by formula (1-3) Is more excellent in the stability of the polymer compound of the present embodiment, so that it is preferably 0.1 to 70 mol%, preferably 1 to 60 mol% with respect to all structural units contained in the polymer compound. It is more preferable, it is more preferable that it is 2-50 mol%, and it is especially preferable that it is 3-40 mol%.

  Structural unit represented by formula (1-1) (including structural units represented by formula (1-1-A) and formula (1-1-B)), structural unit represented by formula (1-2) Examples of the structural unit represented by Formula (1-3) include structural units represented by the following Formula (1-1) to Formula (1-35), and are represented by Formula (1-1) to Formula (1). -24) is preferable, the structural units represented by Formula (1-1) to Formula (1-17) are more preferable, and the structures represented by Formula (1-1) to Formula (1-11) are preferable. Units are even more preferred.

  A structural unit represented by formula (1-1) (may be a structural unit represented by formula (1-1-A) or formula (1-1-B)), represented by formula (1-2) Structural units (may be structural units represented by formula (1-2-A) or formula (1-2-B)) and structural units represented by formula (1-3) (formula (1- Each of the structural units represented by 3-A) may be included in the polymer compound, and may be included in two or more types.

(Structural unit represented by Formula (2))

  In the formula (2), a and b each independently represent an integer of 0 to 3, preferably 0 or 1, and more preferably 0.

R ⁴ and R ⁵ are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted 1 A valent heterocyclic group is shown.

R ⁴ and R ⁵ are an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkyl group, because when the polymer compound of this embodiment is used for the production of a light emitting device, the resulting light emitting device has a better luminance life. Aryl groups are preferred.

Unsubstituted or substituted alkyl group represented by R ⁴ and R ⁵ , unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic ring The definitions and examples of the groups are respectively unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted, represented by R ¹ , R ² , R ³ R ^x1 , R ^x2 , R ^y1 and R ^y2. The definition and examples are the same as those of the aryl group, unsubstituted or substituted aryloxy group, and unsubstituted or substituted monovalent heterocyclic group.

R ⁶ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group.
R ⁷ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group.

R ⁶ is easy to produce the polymer compound of this embodiment, and when the polymer compound of this embodiment is used for the production of a light-emitting device, the luminance life of the resulting light-emitting device is more excellent, An unsubstituted or substituted alkyl group or an unsubstituted or substituted alkoxy group is preferred, and an unsubstituted or substituted alkyl group is more preferred.

R ⁷ is easy to produce the polymer compound of this embodiment, and when the polymer compound of this embodiment is used for the production of a light-emitting device, the luminance life of the resulting light-emitting device is more excellent, An unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent heterocyclic group is preferred, and an unsubstituted or substituted aryl group is more preferred.

When the polymer compound of this embodiment is used for the production of a light-emitting device, the combination of R ⁶ and R ⁷ is that the resulting light-emitting device has a better luminance life, so one of them is an unsubstituted or substituted alkyl group. The other is preferably an unsubstituted or substituted aryl group, more preferably one is an unsubstituted or substituted alkyl group, and the other is a phenyl group or a phenyl group substituted with an alkyl group, and one is More preferably, it is an unsubstituted alkyl group, and the other is a phenyl group substituted with an alkyl group.

Definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted alkoxy group represented by R ⁶ are the unsubstituted or substituted alkyl group and unsubstituted represented by R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ , respectively. Or it is the same as the definition and example of a substituted alkoxy group.

Definitions and examples of the unsubstituted or substituted aryl group, the unsubstituted or substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group represented by R ⁷ are R ²⁶ , R ²⁷ , R ²⁸ and R, respectively. ²⁹ is the same as the definition and examples of the unsubstituted or substituted aryl group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group represented by ²⁹ .

  The proportion of the structural unit represented by the formula (2) is 0.1 to 99.9 mol% with respect to all the structural units contained in the polymer compound because the stability of the polymer compound of the present embodiment is more excellent. It is preferable that it is, it is more preferable that it is 5-70 mol%, and it is further more preferable that it is 10-60 mol%.

  Examples of the structural unit represented by the formula (2) include structural units represented by the following formulas (2-1) to (2-18), and the polymer compound of this embodiment is used for the production of a light emitting device. When used, since the luminance life of the light-emitting element to be obtained is more excellent, Formula (2-1) to Formula (2-15) are preferable, and Formula (2-1) to Formula (2-14) are more preferable.

  As for the structural unit represented by the formula (2), only one type may be contained in the polymer compound, or two or more types may be contained.

(Structural unit represented by Formula (3))

  In formula (3), c and d each independently represent an integer of 0 to 3, preferably 0 or 1, and more preferably 0.

In formula (3), R ⁸ and R ⁹ are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or An unsubstituted or substituted monovalent heterocyclic group is shown.

R ⁸ and R ⁹ are each an unsubstituted or substituted alkyl group or an unsubstituted or substituted alkyl group, because when the polymer compound of this embodiment is used for the production of a light-emitting device, the luminance life of the obtained light-emitting device is more excellent. Aryl groups are preferred.

R ⁸ and R ⁹ represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted monovalent heterocyclic ring The definition and examples of the group are respectively R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 , an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, unsubstituted or The definition and example are the same as those of the substituted aryl group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group.

In formula (3), R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, An unsubstituted or substituted aryloxy group or an unsubstituted or substituted monovalent heterocyclic group is shown.

R ¹⁰ , R ¹¹ , R ^12, and R ¹³ are hydrogen atoms, unsubstituted or substituted, because when the polymer compound of this embodiment is used for the production of a light emitting device, the resulting light emitting device has a better luminance life. Are preferably an alkyl group, an unsubstituted or substituted alkoxy group.

R ¹⁰ and R ¹² may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹¹ and R ¹³ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹⁰ and R ¹¹ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹² and R ¹³ are connected to each other to bond to each other. A ring structure may be formed together with the atoms. Provided that at least one pair selected from the group consisting of R ¹⁰ and R ¹² , R ¹¹ and R ¹³ , R ¹⁰ and R ¹¹ , and R ¹² and R ¹³ is bonded to each other, together with the carbon atom to which each is bonded. Form a ring structure.

Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy represented by R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ The definition and examples of the group and the unsubstituted or substituted monovalent heterocyclic group are the unsubstituted or substituted alkyl groups represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 , respectively. The definition and examples are the same as those for the unsubstituted or substituted alkoxy group, the unsubstituted or substituted aryl group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group.

  The structural unit represented by the formula (3) is a structural unit represented by the following formula (3-A) because the obtained luminance life is more excellent when the polymer compound of the present embodiment is used for the production of a light emitting device. Is preferred.

In formula (3-A), c, d, R ⁸ and R ⁹ are as defined above.

In formula (3-A), n ¹ and n ² each independently represent an integer of 1 to 5.

In formula (3-A), R ³⁰ , R ³¹ , R ³² and R ³³ each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl A group, an unsubstituted or substituted aryloxy group or an unsubstituted or substituted monovalent heterocyclic group; When there are a plurality of R ³⁰ , R ³¹ , R ³² and R ³³ , the plurality of R ³⁰ , R ³¹ , R ³² and R ³³ may be the same as or different from each other. R ³⁰ , R ³¹ , R ³² And adjacent groups of R ³³ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded.

R ³⁰ , R ³¹ , R ^32, and R ³³ are hydrogen atoms, unsubstituted or substituted, because when the polymer compound of this embodiment is used for the production of a light emitting device, the resulting light emitting device has a better luminance life. Are preferably an alkyl group or an unsubstituted or substituted aryl group, more preferably a hydrogen atom or an unsubstituted or substituted alkyl group.

Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group and unsubstituted or substituted represented by R ³⁰ , R ³¹ , R ³² and R ³³ The definition and examples of the monovalent heterocyclic group of R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are the unsubstituted or substituted alkyl groups, unsubstituted or substituted, respectively. The definition and examples are the same as those for the alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, and unsubstituted or substituted monovalent heterocyclic group.

In Formula (3-A), when n ¹ is an integer of 2 to 5, a plurality of R ³⁰ may be the same or different from each other, and a plurality of R ³¹ may be the same or different from each other. When n ² is an integer of ² to 5, a plurality of R ³² may be the same or different, and a plurality of R ³³ may be the same or different. Moreover, adjacent groups among R ³⁰ , R ³¹ , R ³² and R ³³ may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.

In the structural unit represented by the formula (3-A), for example, when n ¹ and / or n ² is 2 or more and has a substituent, R ³⁰ and R ³¹ are different from each other, R ³² and Stereoisomerism can occur when R ³³ is different from each other. The polymer compound of this embodiment may have only a structural unit having the same stereoisomer as the structural unit represented by the formula (3-A), and a plurality of structural units having different stereoisomerism from each other. You may have. Examples of stereoisomerism include diastereomers and enantiomers.

When the structural unit represented by the formula (3-A) includes, for example, a skeleton portion represented by the following formula (3-A1), examples of the stereoisomerism include the following formula (3-a1), (3-b1), Formula (3-c1), and Formula (3-d1). In the following formulae, R ^m and R ⁿ each independently represents an unsubstituted or substituted alkyl group.

  The skeleton part represented by the formula (3-a1), the skeleton part represented by the formula (3-b1), the skeleton part represented by the formula (3-c1) and the skeleton part represented by the formula (3-d1) It is in a diastereomeric relationship.

In the formula (3-A), “adjacent groups of R ³⁰ , R ³¹ , R ³² and R ³³ may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.
”Means, for example, that groups bonded to the same carbon atom among R ³⁰ , R ³¹ , R ³² and R ³³ may be linked to each other to form a ring structure together with the carbon atom to which each is bonded, When n ¹ and / or n ² is 2 or more, it means that groups bonded to adjacent carbon atoms may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded.

The formed ring structure may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or Examples thereof include a substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

In formula (3-A), when the polymer compound of the present embodiment is used for the production of a light emitting device, the obtained luminance life is more excellent, and therefore n ¹ and are preferably integers of 3 to 5. 3 or 4 is more preferable, and 3 is more preferable.

In formula (3-A), n ¹ and n ² may be the same as or different from each other, but since the production of the polymer compound of the present embodiment is facilitated, n ¹ and n ² are the same as each other. Is preferred.

  The proportion of the structural unit represented by the formula (3) (which may be the structural unit represented by the formula (3-A)) is superior in the stability of the polymer compound of the present embodiment. It is preferable that it is 0.1-99.9 mol% with respect to all the structural units contained in, It is more preferable that it is 5-70 mol%, It is further more preferable that it is 10-60 mol%.

  Examples of the structural unit represented by the formula (3) (including the structural unit represented by the formula (3-A)) include structural units represented by the following formulas (3-1) to (3-16). And structural units represented by formulas (3-1) to (3-14) are preferable, and structural units represented by formulas (3-1) to (3-9) are more preferable.

  The structural unit represented by the formula (3) (may be the structural unit represented by the formula (3-A)) may be included in the polymer compound alone or in combination of two or more. It may be.

(Structural unit represented by Formula (4))

In the formula (4), R ¹⁴ and R ¹⁵ each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown. However, at least one selected from the group consisting of R ¹⁴ and R ¹⁵ represents a group other than a hydrogen atom.

R ¹⁴ and R ¹⁵ are each an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkyl group, because when the polymer compound of this embodiment is used for the production of a light emitting device, the luminance life of the obtained light emitting device is more excellent. An aryl group is preferred, and an unsubstituted or substituted alkyl group is more preferred.

The unsubstituted or substituted alkyl group represented by R ¹⁴ and R ¹⁵ may be linear, branched or cyclic. The number of carbon atoms of the linear alkyl group does not include the number of carbon atoms of the substituent, and is usually 1 to 50, preferably 3 to 30, and more preferably 4 to 20. The number of carbon atoms of the branched alkyl group and the cyclic alkyl group is usually 3-50, preferably 3-30, more preferably 4-20, not including the number of carbon atoms of the substituent. .
Examples of the unsubstituted or substituted alkyl group represented by R ¹⁴ and R ¹⁵ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, and an n-pentyl group. , Isoamyl group, 2-ethylbutyl group, n-hexyl group, cyclohexyl group, n-heptyl group, cyclohexylmethyl group, cyclohexylethyl group, n-octyl group, 2-ethylhexyl group, 3-n-propylheptyl group, n- A decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, a 2-n-hexyl-decyl group, and a group in which a hydrogen atom in these groups is substituted with an aryl group, an alkoxy group, a fluorine atom, or the like. Methyl group, ethyl group, n-propyl group, n-butyl group, isobutyl group, n-pentyl group, isoa Group, 2-ethylbutyl group, n-hexyl group, n-heptyl group, cyclohexylethyl group, n-octyl group, 2-ethylhexyl group, 3-n-propylheptyl group, n-decyl group, 3,7-dimethyl Octyl group, 2-ethyloctyl group, 2-n-hexyl-decyl group are more preferable, n-butyl group, isobutyl group, n-pentyl group, isoamyl group, 2-ethylbutyl group, n-hexyl group, n-heptyl group. Group, cyclohexylethyl group, n-octyl group, 2-ethylhexyl group, 3-n-propylheptyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyl-decyl group More preferably a cyclohexylethyl group, an n-octyl group, a 2-ethylhexyl group, a 3-n-propylheptyl group, an n-decyl group, A 3,7-dimethyloctyl group and a 2-ethyloctyl group are particularly preferred.

Definitions and examples of the unsubstituted or substituted aryl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryloxy group and unsubstituted or substituted monovalent heterocyclic group represented by R ¹⁴ and R ¹⁵ are respectively R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted aryl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryloxy group, an unsubstituted group Or it is the same as the definition and example of a substituted monovalent heterocyclic group.

  The proportion of the structural unit represented by formula (4) is 0.1 to 99.9 mol% with respect to the total structural units contained in the polymer compound because the stability of the polymer compound of this embodiment is more excellent. It is preferably 5 to 95 mol%, more preferably 10 to 60 mol%.

  As a structural unit shown by Formula (4), the structural unit shown by following formula (4-1)-Formula (4-14) is mentioned, for example, Formula (4-1)-Formula (4-12) The structural unit shown by Formula (4-1)-Formula (4-7) is more preferable.

  As for the structural unit represented by the formula (4), only one kind may be contained in the polymer compound, or two or more kinds may be contained.

  When the polymer compound of this embodiment is used for the production of a light emitting device, the luminance life of the obtained light emitting device is more excellent. Therefore, in the structural unit represented by the formula (1-1), the formula (1-2) A polymer compound comprising at least one structural unit selected from the group consisting of a structural unit represented by formula (1-3) and a structural unit represented by formula (2); ), At least one structural unit selected from the group consisting of the structural unit represented by formula (1-2) and the structural unit represented by formula (1-3) and the formula (4). Or from a group consisting of a structural unit represented by formula (1-1), a structural unit represented by formula (1-2), and a structural unit represented by formula (1-3) At least one selected structural unit and the structure represented by formula (2) It is preferable that it is a high molecular compound containing a unit and the structural unit shown by Formula (4), the structural unit shown by Formula (1-1), the structural unit shown by Formula (1-2), and Formula (1) 3) a polymer compound including at least one structural unit selected from the group consisting of structural units represented by formula (3), a structural unit represented by formula (2), and a structural unit represented by formula (4). More preferred.

  The polymer compound of the present embodiment is represented by the structural unit represented by the following formula (5) (the structural unit represented by the formula (2), the structural unit represented by the formula (3), and the formula (4). It may be further included.

In Formula (5), Ar ³ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ³ does not include the number of carbon atoms of the substituent, and is preferably 6 to 60, more preferably 6 to 30, and still more preferably 6 to 18.
Examples of the arylene group represented by Ar ³ include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthalenediyl group, 1,5-naphthalenediyl group, 2 , 6-Naphthalenediyl group, 2,7-phenanthenediyl group, 5,12-naphthacenediyl group, 2,7-fluorenediyl group, 3,6-fluorenediyl group, 2,6-anthracenediyl group, 9, Examples include 10-anthracenediyl group, 1,6-pyrenediyl group, 2,7-pyrenediyl group, 3,9-perylenediyl group, 3,10-perylenediyl group, 6,12-chrysenediyl group, and 2,8-chrysenediyl group. .

As the arylene group represented by Ar ^3, when the polymer compound of this embodiment is used for the production of a light-emitting device, the resulting light-emitting device has a superior luminance life, and thus a 1,4-phenylene group, 2,7- Full orangeyl is preferred.

The number of carbon atoms of the unsubstituted or substituted divalent heterocyclic group represented by Ar ³ does not include the number of carbon atoms of the substituent, is preferably 4 to 60, more preferably 4 to 30, Preferably it is 4-15.
Examples of the divalent heterocyclic group represented by Ar ³ include 2,5-thiophenediyl group, 2,5-pyrroldiyl group, 2,5-furandiyl group, 2,5-pyridinediyl group, 2,6- Pyridinediyl group, 2,6-quinolinediyl group, 1,4-isoquinolinediyl group, 1,5-isoquinolinediyl group, 5,8-quinoxalinediyl group, 2,1,3-benzothiadiazole-4,7-diyl group 2,7-dibenzofurandiyl group, 2,7-dibenzothiophenediyl group, 2,7-dibenzosilolediyl group.

The group represented by Ar ³ may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted group, Examples thereof include an aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group and a cyano group, and an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferred.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

  The proportion of the structural unit represented by the formula (5) is 0.1 to 70 mol% with respect to all the structural units contained in the polymer compound because the stability of the polymer compound of this embodiment is more excellent. It is preferable that it is 1 to 50 mol%.

  Examples of the structural unit represented by the formula (5) include structural units represented by the following formulas (5-1) to (5-35).

  The polymer compound of this embodiment includes a structural unit represented by the following formula (6) (a structural unit represented by the formula (1-1), a structural unit represented by the formula (1-2), and the formula (1). 3) and the structural unit represented by the formula (5) are preferably further included.

In formula (6), a ¹ and a ² each independently represent 0 or 1.
Ar ⁴ and Ar ⁶ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ⁵ and Ar ⁷ each independently represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or the same or different two or more selected from an arylene group and a divalent heterocyclic group The bivalent group which this group connected (The said bivalent group may have a substituent.) Is shown.
R ^C , R ^D and R ^E each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ may each be linked to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring structure.

In formula (6), a ¹ is more preferably 1 because the obtained luminance life is more excellent when the polymer compound of the present embodiment is used for the production of a light emitting device.

Wherein (6), a ² is easy to manufacture the polymer compound of this embodiment, and, in the case where the polymer compound of this embodiment is used in the manufacture of the light emitting device, resulting luminance lifetime more Since it is excellent, 0 is preferable.

In the formula (6), the group represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ is an unsubstituted or substituted arylene group, which improves the stability of the polymer compound of the present embodiment, And when the polymer compound of this embodiment is used for manufacture of a light emitting element, since the luminance life of the obtained light emitting element is more excellent, it is preferable.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 30 Yes, more preferably 6-18.
Examples of the arylene group represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ include a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 1,4-naphthalenediyl group, 1 , 5-naphthalenediyl group, 2,6-naphthalenediyl group, 2,7-naphthalenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group, 2,7 -Dihydrophenanthrene diyl group, 5,12-naphthacene diyl group, 2,7-fluorenediyl group, 3,6-fluorenediyl group, 1,6-pyrene diyl group, 2,7-pyrene diyl group, 3,9-perylene diyl group 3,10-perylenediyl group, 6,12-chrysenediyl group, 2,8-chrysenediyl group, 1,4-phenylene group, 2,6- Phthalenediyl group, 2,7-fluorenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group, 2,7-dihydrophenanthenediyl group, 1,6-pyrenediyl group 1,4-phenylene group and 2,7-fluorenediyl are more preferable.

The number of carbon atoms of the unsubstituted or substituted divalent heterocyclic group represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ does not include the number of carbon atoms of the substituent, preferably 4 to 60, more preferably It is 4-30, More preferably, it is 4-15.
Examples of the divalent heterocyclic group represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ include 2,5-thiophenediyl group, 2,5-pyrrolediyl group, 2,5-furandiyl group, 2,5 -Pyridinediyl group, 2,6-pyridinediyl group, 2,6-quinolinediyl group, 1,4-isoquinolinediyl group, 1,5-isoquinolinediyl group, 5,8-quinoxalinediyl group, 2,7-carbazolediyl Group, 3,6-carbazolediyl group, 3,7-phenoxazinediyl group, 3,7-phenothiazinediyl group, 2,8-phenothiazinediyl group, 4,6-phenothiazinediyl group, 2,1,3-benzo Thiadiazole-4,7-diyl group, 2,7-dibenzofurandiyl group, 2,7-dibenzothiophenediyl group, 2,7-dibenzosiloldiyl group, etc. It is below.

Examples of the divalent group in which two or more identical or different groups selected from the arylene group and the divalent heterocyclic group represented by Ar ⁵ and Ar ⁷ are linked include the following formulas (1a-1) and (1a- 2), a group represented by the formula (1a-3), the formula (1a-4), the formula (1a-5), the formula (1a-6) or the formula (1a-7) can be selected. The group represented by (1a-1) is preferred.

The groups represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ may have a substituent. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. Examples thereof include a cyclic group and a cyano group, and an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferred.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

In the formula (6), R ^C , R ^D and R ^E are obtained when the stability of the polymer compound of this embodiment is improved and the polymer compound of this embodiment is used for the production of a light emitting device. In order to obtain better luminance lifetime, it is preferably a substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group, and preferably an unsubstituted or substituted aryl group. Is more preferable.

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group represented by R ^C , R ^D, and R ^E are R ^A and R ^B , respectively. Are the same as the definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group.

  The proportion of the structural unit represented by the formula (6) is 0.1 to 40 mol% with respect to all the structural units contained in the polymer compound because the stability of the polymer compound of this embodiment is more excellent. It is preferably 0.5 to 30 mol%, more preferably 1 to 20 mol%.

  As a structural unit shown by Formula (6), the structural unit shown by following formula (6-1)-Formula (6-6) is mentioned, for example, Formula (6-1), Formula (6-2) Or the structural unit shown by Formula (6-3) is preferable, and the structural unit shown by Formula (6-1) or Formula (6-2) is more preferable.

  The structural unit represented by the formula (6) is preferably a structural unit represented by the following formula (7).

In Formula (7), R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^{b s} may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.

In Formula (7), R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.

^RF has better stability of the polymer compound of the present embodiment, and when the polymer compound of the present embodiment is used in the production of a light-emitting device, the luminance life of the obtained light-emitting device is more excellent. Therefore, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group is preferable, and an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group is preferable. It is more preferable that it is an unsubstituted or substituted aryl group.

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group represented by R ^F are the same as those represented by R ^C , R ^D, and R ^E , respectively. The definition and examples are the same as those of the substituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group.

In formula (7), Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^b may be the same or different.

  Z is preferably a single bond or an oxygen atom, and is preferably an oxygen atom, since the luminance life of the obtained light-emitting device is more excellent when the polymer compound of this embodiment is used in the production of a light-emitting device. More preferred.

The definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ^b are respectively R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2. The definition and examples of the substituted or substituted alkyl group and the unsubstituted or substituted aryl group are the same.

  Examples of the structural unit represented by the formula (7) include structural units represented by the following formulas (7-1) to (7-7). The polymer compound of the present embodiment is used for the production of a light emitting device. When used, the luminance life obtained is more excellent, and thus the structural units represented by the formulas (7-1) to (7-5) are preferable.

  The polymer compound of the present invention is at least selected from the group consisting of a structural unit represented by formula (1-1), a structural unit represented by formula (1-2), and a structural unit represented by formula (1-3). One type of structural unit, a structural unit represented by the following formula (8) (a structural unit represented by the formula (1-1), a structural unit represented by the formula (1-2), and the formula (1-3) ), A structural unit represented by the formula (2), a structural unit represented by the formula (3), a structural unit represented by the formula (4), and a structural unit represented by the formula (5). And different from the structural unit represented by the formula (6).

In formula (8), na represents an integer of 0 to 3, nb represents an integer of 0 to 12, nA represents 0 or 1, and n represents 1 or 2.
Ar ⁸ represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent aromatic amine group, or an unsubstituted or substituted divalent heterocyclic group.
L ^a and L ^b each independently represent a direct bond, an unsubstituted or substituted alkylene group, or an unsubstituted or substituted phenylene group. When ^a plurality of ^La are present, they may be the same or different. When a plurality of ^Lb are present, they may be the same or different.
L ^A represents an oxygen atom or a sulfur atom. When a plurality of ^LA are present, they may be the same or different.
X ′ represents a monovalent crosslinkable group. When a plurality of X ′ are present, they may be the same or different.

  na is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0, because the production of the polymer compound of the present embodiment becomes easier.

  nb is preferably 0 to 10 and more preferably 0 to 8 because the production of the polymer compound of the present embodiment becomes easier.

  nA is preferably 0 because the luminance lifetime of the light emitting device produced using the polymer compound of the present embodiment is more excellent.

  n is preferably 2 because the luminance lifetime of the light emitting device produced using the polymer compound of the present embodiment is more excellent.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ⁸ does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 30, and more preferably 6 to 18. is there.
Examples of the arylene group represented by Ar ⁸ include 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthalenediyl group, 1,5-naphthalenediyl group, 2,6-naphthalenediyl group, 2 , 7-naphthalenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group, 2,7-dihydrophenanthenediyl group, 5,12-naphthacenediyl group, 2,7 -Full orangeyl, 3,6-fluorenediyl group, 1,6-pyrene diyl group, 2,7-pyrene diyl group, 3,9-perylene diyl group, 3,10-perylene diyl group, 6,12-chrysenediyl group, 2 , 8-chrysenediyl group, 2,6-naphthalenediyl group, 2,7-fluorenediyl group, 2,6-anthracenediyl group 9,10-anthracenediyl group, 2,7-phenanthrenediyl group, 2,7-dihydrophenanthrenediyl group, 1,6-pyrenediyl group are preferable, 2,6-naphthalenediyl group, 2,7-fluorenediyl group Is more preferable.

Examples of the divalent aromatic amine group represented by Ar ⁸ include divalent groups represented by the following formulas (8-a) to (8-e).

The definition and examples of the divalent heterocyclic group represented by Ar ⁸ are the same as the definitions and examples of the divalent heterocyclic group represented by Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ .

The group represented by Ar ⁸ may have a substituent. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted group, and the like. Examples thereof include an aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

The alkylene group represented by L ^a and L ^b may be linear, branched or cyclic, and may have a substituent. Since production of the polymer compound of this embodiment becomes easier, a linear alkylene group is preferable. The carbon number of a linear alkylene group is 1-20 normally, Preferably it is 1-10, More preferably, it is 1-6. The number of carbon atoms of the branched alkylene group and the cyclic alkylene group is usually 3 to 20, preferably 3 to 10, and more preferably 3 to 6.
Examples of the alkylene group include a methylene group, 1,2-ethylene group, 1,3-propylene group, 1,3-butylene group, 1,3-pentylene group, 1,4-pentylene group, and 1,5-pentylene. Group, 1,4-hexylene group, 1,6-hexylene group, 1,7-heptylene group, 1,6-octylene group, 1,8-octylene group.

The phenylene group represented by L ^a and L ^b may have a substituent. Examples of the phenylene group include o-phenylene, m-phenylene, and p-phenylene. Examples of the substituent that the phenylene group may have include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, a halogen atom, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups and unsubstituted or substituted alkoxy groups are defined by the unsubstituted or substituted groups represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 , respectively. The definitions and examples of the alkyl group and the unsubstituted or substituted alkoxy group are the same.

L ^a, since the production of the polymer compound of the present embodiment is easier, it is preferably a direct bond or a phenylene group.

L ^b is preferably a direct bond or an alkylene group, because the production of the polymer compound of the present embodiment becomes easier.

L ^A, since the production of the polymer compound of the present embodiment is easier, is preferably an oxygen atom.

  Examples of the monovalent crosslinkable group represented by X ′ include aziridinyl group, azetidinyl group, azide group, epoxy group, oxetanyl group, alkenyl group, alkynyl group, and group having cyclobutene. For easier production of the compound, an aziridinyl group, an azide group, an epoxy group, an oxetanyl group, an alkenyl group, an alkynyl group, an aryl group having a cyclobutene, and a monovalent heterocyclic group having a cyclobutene are preferable. An aryl group having a monovalent heterocyclic group having cyclobutene is more preferable.

The monovalent crosslinkable group represented by X ′ may have a substituent. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. A cyclic group and a cyano group are mentioned.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, and an unsubstituted group, respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

  The proportion of the structural unit represented by the formula (8) is more excellent in the stability of the polymer compound of the present embodiment and the crosslinkability of the present embodiment. On the other hand, it is preferably 0.5 to 40 mol%, more preferably 3 to 30 mol%, and further preferably 3 to 20 mol%.

  As a structural unit shown by Formula (8), the structural unit shown by following formula (8-1)-(8-30) is mentioned, for example. In addition, the compound which has a double bond in which a wavy line exists means that any of E-form, Z-form, or a mixture of E-form and Z-form may be used.

  Examples of preferable combinations of the structural units in the polymer compound of the present embodiment are shown below. In addition, Q1-Q124 represents the molar ratio of the structural unit in a parenthesis with respect to all the structural units of a high molecular compound.

（式中、
Ｑ１は３〜２０の数を示し、Ｑ２は２０〜５０の数を示し、Ｑ３は４０〜６０の数を示す。但し、Ｑ１＋Ｑ２＋Ｑ３＝１００である。
Ｑ４は３〜２０の数を示し、Ｑ５は２０〜５０の数を示し、Ｑ６は１０〜５０の数を示し、Ｑ７は２０〜５０の数を示す。但し、Ｑ４＋Ｑ５＋Ｑ６＋Ｑ７＝１００である。
Ｑ８は３〜２０の数を示し、Ｑ９は１０〜５０の数を示し、Ｑ１０は２０〜５０の数を示し、Ｑ１１は２０〜５０の数を示す。但し、Ｑ８＋Ｑ９＋Ｑ１０＋Ｑ１１＝１００である。
Ｑ１２は３〜２０の数を示し、Ｑ１３は１０〜５０の数を示し、Ｑ１４は４０〜８０の数を示す。但し、Ｑ１２＋Ｑ１３＋Ｑ１４＝１００である。）

(Where
Q1 represents a number from 3 to 20, Q2 represents a number from 20 to 50, and Q3 represents a number from 40 to 60. However, Q1 + Q2 + Q3 = 100.
Q4 represents a number from 3 to 20, Q5 represents a number from 20 to 50, Q6 represents a number from 10 to 50, and Q7 represents a number from 20 to 50. However, Q4 + Q5 + Q6 + Q7 = 100.
Q8 represents a number from 3 to 20, Q9 represents a number from 10 to 50, Q10 represents a number from 20 to 50, and Q11 represents a number from 20 to 50. However, Q8 + Q9 + Q10 + Q11 = 100.
Q12 represents a number of 3 to 20, Q13 represents a number of 10 to 50, and Q14 represents a number of 40 to 80. However, Q12 + Q13 + Q14 = 100. )

（式中、
Ｑ１５は３〜２０の数を示し、Ｑ１６は２０〜５０の数を示し、Ｑ１７は２０〜５０の数を示し、Ｑ１８は２０〜５０の数を示す。但し、Ｑ１５＋Ｑ１６＋Ｑ１７＋Ｑ１８＝１００である。
Ｑ１９は３〜２０の数を示し、Ｑ２０は２０〜５０の数を示し、Ｑ２１は１０〜５０の数を示し、Ｑ２２は５〜５０の数を示す。但し、Ｑ１９＋Ｑ２０＋Ｑ２１＋Ｑ２２＝１００である。）

(Where
Q15 represents a number from 3 to 20, Q16 represents a number from 20 to 50, Q17 represents a number from 20 to 50, and Q18 represents a number from 20 to 50. However, Q15 + Q16 + Q17 + Q18 = 100.
Q19 represents a number from 3 to 20, Q20 represents a number from 20 to 50, Q21 represents a number from 10 to 50, and Q22 represents a number from 5 to 50. However, Q19 + Q20 + Q21 + Q22 = 100. )

（式中、
Ｑ２３は３〜２０の数を示し、Ｑ２４は１０〜５０の数を示し、Ｑ２５は２０〜５０の数を示す。但し、Ｑ２３＋Ｑ２４＋Ｑ２５＝１００である。
Ｑ２６は３〜２０の数を示し、Ｑ２７は２０〜５０の数を示し、Ｑ２８は４０〜６０の数を示す。但し、Ｑ２６＋Ｑ２７＋Ｑ２８＝１００である。
Ｑ２９は３〜２０の数を示し、Ｑ３０は１０〜５０の数を示し、Ｑ３１は１０〜５０の数を示し、Ｑ３２は２０〜５０の数を示す。但し、Ｑ２９＋Ｑ３０＋Ｑ３１＋Ｑ３２＝１００である）

(Where
Q23 represents a number from 3 to 20, Q24 represents a number from 10 to 50, and Q25 represents a number from 20 to 50. However, Q23 + Q24 + Q25 = 100.
Q26 represents a number from 3 to 20, Q27 represents a number from 20 to 50, and Q28 represents a number from 40 to 60. However, Q26 + Q27 + Q28 = 100.
Q29 shows the number of 3-20, Q30 shows the number of 10-50, Q31 shows the number of 10-50, Q32 shows the number of 20-50. (However, Q29 + Q30 + Q31 + Q32 = 100)

（式中、
Ｑ３３は３〜２０の数を示し、Ｑ３４は４０〜６０の数を示し、Ｑ３５は３０〜５０の数を示し、Ｑ３６は１．５〜１０の数を示す。但し、Ｑ３３＋Ｑ３４＋Ｑ３５＋Ｑ３６＝１００である。
Ｑ３７は３〜２０の数を示し、Ｑ３８は１０〜５０の数を示し、Ｑ３９は４０〜６０の数を示し、Ｑ４０は１．５〜１０の数を示す。但し、Ｑ３７＋Ｑ３８＋Ｑ３９＋Ｑ４０＝１００である。）

(Where
Q33 represents a number of 3 to 20, Q34 represents a number of 40 to 60, Q35 represents a number of 30 to 50, and Q36 represents a number of 1.5 to 10. However, Q33 + Q34 + Q35 + Q36 = 100.
Q37 represents a number of 3 to 20, Q38 represents a number of 10 to 50, Q39 represents a number of 40 to 60, and Q40 represents a number of 1.5 to 10. However, Q37 + Q38 + Q39 + Q40 = 100. )

（式中、
Ｑ４１は２０〜４０の数を示し、Ｑ４２は３〜２０の数を示し、Ｑ４３は１．５〜１０の数を示し、Ｑ４４は４０〜６０の数を示す。但し、Ｑ４１＋Ｑ４２＋Ｑ４３＋Ｑ４４＝１００である。
Ｑ４５は３〜２０の数を示し、Ｑ４６は２０〜５０の数を示し、Ｑ４７は２０〜５０の数を示し、Ｑ４８は１．５〜１０の数を示し、Ｑ４９は１．５〜１０の数を示す。但し、Ｑ４５＋Ｑ４６＋Ｑ４７＋Ｑ４８＋Ｑ４９＝１００である。
Ｑ５０は３〜２０の数を示し、Ｑ５１は４０〜６０の数を示し、Ｑ５２は１０〜５０の数を示し、Ｑ５３は１．５〜１０の数を示す。但し、Ｑ５０＋Ｑ５１＋Ｑ５２＋Ｑ５３＝１００である。
Ｑ５４は３〜２０の数を示し、Ｑ５５は４０〜６０の数を示し、Ｑ５６は１０〜５０の数を示し、Ｑ５７は１．５〜１０の数を示す。但し、Ｑ５４＋Ｑ５５＋Ｑ５６＋Ｑ５７＝１００である。）

(Where
Q41 represents a number of 20 to 40, Q42 represents a number of 3 to 20, Q43 represents a number of 1.5 to 10, and Q44 represents a number of 40 to 60. However, Q41 + Q42 + Q43 + Q44 = 100.
Q45 represents a number of 3 to 20, Q46 represents a number of 20 to 50, Q47 represents a number of 20 to 50, Q48 represents a number of 1.5 to 10, Q49 represents a number of 1.5 to 10 Indicates a number. However, Q45 + Q46 + Q47 + Q48 + Q49 = 100.
Q50 represents a number from 3 to 20, Q51 represents a number from 40 to 60, Q52 represents a number from 10 to 50, and Q53 represents a number from 1.5 to 10. However, Q50 + Q51 + Q52 + Q53 = 100.
Q54 represents a number of 3 to 20, Q55 represents a number of 40 to 60, Q56 represents a number of 10 to 50, and Q57 represents a number of 1.5 to 10. However, Q54 + Q55 + Q56 + Q57 = 100. )

（式中、
Ｑ５８は３〜２０の数を示し、Ｑ５９は２０〜５０の数を示し、Ｑ６０は４０〜６０の数を示す。但し、Ｑ５８＋Ｑ５９＋Ｑ６０＝１００である。）

(Where
Q58 represents a number from 3 to 20, Q59 represents a number from 20 to 50, and Q60 represents a number from 40 to 60. However, Q58 + Q59 + Q60 = 100. )

（式中、
Ｑ６１は３〜２０の数を示し、Ｑ６２は４０〜６０の数を示し、Ｑ６３は１０〜５０の数を示し、Ｑ６４は１０〜５０の数を示す。但し、Ｑ６１＋Ｑ６２＋Ｑ６３＋Ｑ６４＝１００である。
Ｑ６５は３〜２０の数を示し、Ｑ６６は４０〜６０の数を示し、Ｑ６７は３０〜５０の数を示し、Ｑ６８は１.５〜１０の数を示す。但し、Ｑ６５＋Ｑ６６＋Ｑ６７＋Ｑ６８＝１００である。
Ｑ６９は２０〜４０の数を示し、Ｑ７０は１０〜５０の数を示し、Ｑ７１は４０〜６０の数を示し、Ｑ７２は３〜２０の数を示す。但し、Ｑ６９＋Ｑ７０＋Ｑ７１＋Ｑ７２＝１００である。）

(Where
Q61 represents a number from 3 to 20, Q62 represents a number from 40 to 60, Q63 represents a number from 10 to 50, and Q64 represents a number from 10 to 50. However, Q61 + Q62 + Q63 + Q64 = 100.
Q65 represents a number of 3 to 20, Q66 represents a number of 40 to 60, Q67 represents a number of 30 to 50, and Q68 represents a number of 1.5 to 10. However, Q65 + Q66 + Q67 + Q68 = 100.
Q69 shows the number of 20-40, Q70 shows the number of 10-50, Q71 shows the number of 40-60, Q72 shows the number of 3-20. However, Q69 + Q70 + Q71 + Q72 = 100. )

（式中、
Ｑ７３は３〜２０の数を示し、Ｑ７４は４０〜６０の数を示し、Ｑ７５は１０〜５０の数を示し、Ｑ７６は１.５〜１０の数を示し、Ｑ７７は１.５〜１０の数を示す。但し、Ｑ７３＋Ｑ７４＋Ｑ７５＋Ｑ７６＋Ｑ７７＝１００である。
Ｑ７８は３〜２０の数を示し、Ｑ７９は４０〜６０の数を示し、Ｑ８０は２０〜５０の数を示し、Ｑ８１は１.５〜１０の数を示す。但し、Ｑ６５＋Ｑ６６＋Ｑ６７＋Ｑ６８＝１００である。）

(Where
Q73 represents a number from 3 to 20, Q74 represents a number from 40 to 60, Q75 represents a number from 10 to 50, Q76 represents a number from 1.5 to 10, Q77 represents a number from 1.5 to 10 Indicates a number. However, Q73 + Q74 + Q75 + Q76 + Q77 = 100.
Q78 represents a number from 3 to 20, Q79 represents a number from 40 to 60, Q80 represents a number from 20 to 50, and Q81 represents a number from 1.5 to 10. However, Q65 + Q66 + Q67 + Q68 = 100. )

（式中、
Ｑ８２は２０〜４０の数を示し、Ｑ８３は３〜２０の数を示し、Ｑ８４は１.５〜１０の数を示し、Ｑ８５は４０〜６０の数を示す。但し、Ｑ８２＋Ｑ８３＋Ｑ８４＋Ｑ８５＝１００である。
Ｑ８６は３〜２０の数を示し、Ｑ８７は２０〜５０の数を示し、Ｑ８８は２０〜５０の数を示し、Ｑ８９は１０〜５０の数を示す。但し、Ｑ８６＋Ｑ８７＋Ｑ８８＋Ｑ８９＝１００である。）

(Where
Q82 represents a number of 20 to 40, Q83 represents a number of 3 to 20, Q84 represents a number of 1.5 to 10, and Q85 represents a number of 40 to 60. However, Q82 + Q83 + Q84 + Q85 = 100.
Q86 represents a number from 3 to 20, Q87 represents a number from 20 to 50, Q88 represents a number from 20 to 50, and Q89 represents a number from 10 to 50. However, Q86 + Q87 + Q88 + Q89 = 100. )

（式中、
Ｑ９０は３〜２０の数を示し、Ｑ９１は２０〜６０の数を示し、Ｑ９２は２０〜６０の数を示す。但し、Ｑ９０＋Ｑ９１＋Ｑ９２＝１００である。）
Ｑ９３は３〜２０の数を示し、Ｑ９４は４０〜９０の数を示し、Ｑ９５は１.５〜１０の数を示す。但し、Ｑ９３＋Ｑ９４＋Ｑ９５＝１００である。
Ｑ９６は３〜２０の数を示し、Ｑ９７は４０〜６０の数を示し、Ｑ９８は１０〜５０の数を示し、Ｑ９９は１０〜５０の数を示す。但し、Ｑ９６＋Ｑ９７＋Ｑ９８＋Ｑ９９＝１００である。
Ｑ１００は２０〜４０の数を示し、Ｑ１０１は３〜２０の数を示し、Ｑ１０２は３〜２０の数を示し、Ｑ１０３は１.５〜１０の数を示し、Ｑ１０４は４０〜６０の数を示す。
但し、Ｑ１００＋Ｑ１０１＋Ｑ１０２＋Ｑ１０３＋Ｑ１０４＝１００である。）

(Where
Q90 represents a number from 3 to 20, Q91 represents a number from 20 to 60, and Q92 represents a number from 20 to 60. However, Q90 + Q91 + Q92 = 100. )
Q93 represents a number from 3 to 20, Q94 represents a number from 40 to 90, and Q95 represents a number from 1.5 to 10. However, Q93 + Q94 + Q95 = 100.
Q96 represents a number of 3 to 20, Q97 represents a number of 40 to 60, Q98 represents a number of 10 to 50, and Q99 represents a number of 10 to 50. However, Q96 + Q97 + Q98 + Q99 = 100.
Q100 represents a number of 20 to 40, Q101 represents a number of 3 to 20, Q102 represents a number of 3 to 20, Q103 represents a number of 1.5 to 10, and Q104 represents a number of 40 to 60. Show.
However, Q100 + Q101 + Q102 + Q103 + Q104 = 100. )

（式中、
Ｑ１０５は３〜２０の数を示し、Ｑ１０６は４０〜６０の数を示し、Ｑ１０７は２０〜５０の数を示す。但し、Ｑ１０５＋Ｑ１０６＋Ｑ１０７＝１００である。
Ｑ１０８は３〜２０の数を示し、Ｑ１０９は２０〜５０の数を示し、Ｑ１１０は４０〜６０の数を示し、Ｑ１１１は１.５〜１０の数を示す。但し、Ｑ１０８＋Ｑ１０９＋Ｑ１１０＋Ｑ１１１＝１００である。
Ｑ１１２は３〜２０の数を示し、Ｑ１１３は８０〜９７の数を示す。但し、Ｑ１１２＋Ｑ１１３＝１００である。
Ｑ１１４は３〜２０の数を示し、Ｑ１１５は４０〜６０の数を示し、Ｑ１１６は２０〜５０の数を示し、Ｑ１１７は１.５〜１０の数を示す。但し、Ｑ１１４＋Ｑ１１５＋Ｑ１１６＋Ｑ１１７＝１００である。
Ｑ１１８は２０〜４０の数を示し、Ｑ１１９は３〜２０の数を示し、Ｑ１２０は４０〜６０の数を示し、Ｑ１２１は１.５〜１０の数を示す。但し、Ｑ１１８＋Ｑ１１９＋Ｑ１２０＋Ｑ１２１＝１００である。
Ｑ１２２は３〜２０の数を示し、Ｑ１２３は２０〜５０の数を示し、Ｑ１２４は２０〜６０の数を示す。但し、Ｑ１２２＋Ｑ１２３＋Ｑ１２４＝１００である。）

(Where
Q105 represents a number of 3 to 20, Q106 represents a number of 40 to 60, and Q107 represents a number of 20 to 50. However, Q105 + Q106 + Q107 = 100.
Q108 represents a number of 3 to 20, Q109 represents a number of 20 to 50, Q110 represents a number of 40 to 60, and Q111 represents a number of 1.5 to 10. However, Q108 + Q109 + Q110 + Q111 = 100.
Q112 represents a number from 3 to 20, and Q113 represents a number from 80 to 97. However, Q112 + Q113 = 100.
Q114 represents a number from 3 to 20, Q115 represents a number from 40 to 60, Q116 represents a number from 20 to 50, and Q117 represents a number from 1.5 to 10. However, Q114 + Q115 + Q116 + Q117 = 100.
Q118 represents a number of 20 to 40, Q119 represents a number of 3 to 20, Q120 represents a number of 40 to 60, and Q121 represents a number of 1.5 to 10. However, Q118 + Q119 + Q120 + Q121 = 100.
Q122 represents a number from 3 to 20, Q123 represents a number from 20 to 50, and Q124 represents a number from 20 to 60. However, Q122 + Q123 + Q124 = 100. )

The number average molecular weight (Mn) in terms of polystyrene by gel permeation chromatography (hereinafter referred to as “GPC”) of the polymer compound of the present embodiment is usually 1 × 10 ³ to 1 × 10 ⁸ , preferably Is 1 × 10 ⁴ to 1 × 10 ⁶ . In addition, the weight average molecular weight (Mw) in terms of polystyrene of the polymer compound of the present embodiment is usually 2 × 10 ³ to 2 × 10 ⁸ , and the film formability is improved, and preferably 2 × 10 ^4. It is -2 * 10 < ⁶ >, More preferably, it is 3 * 10 < ⁴ > -1 * 10 < ⁶ >, More preferably, it is 5 * 10 < ⁴ > -5 * 10 < ⁵ >.

  If the polymerization active group remains as it is in the terminal group of the polymer compound of this embodiment, when the polymer compound of this embodiment is used for the production of a light emitting device, the light emission characteristics and the luminance life may be reduced. Therefore, a stable group is preferable. The terminal group is preferably a group conjugated to the main chain, and a group bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond (specifically, JP-A-9- No. 45478, etc.).

  The polymer compound of this embodiment may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be in other modes.

[Method for producing polymer compound]
Next, the preferable manufacturing method of the high molecular compound of this invention is demonstrated.

  In the production of the polymer compound of the present embodiment, for example, a compound represented by the formula (1-1-M), a compound represented by the formula (1-2-M), and a formula (1-3-M) From at least one compound selected from the group consisting of compounds represented by formula (2M), a compound represented by formula (3M), a compound represented by formula (4M), and a compound represented by formula (8M) It can be produced by subjecting at least one compound selected from the group to condensation polymerization. In addition, when the other compound is subjected to condensation polymerization of at least one compound selected from the group consisting of a compound represented by the formula (5M), a compound represented by the formula (6M), and a compound represented by the formula (7M). Further, it may be used.

In formula (1-1-M) to formula (1-3-M), R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ^A , R ^B , Ar ¹ , Ar ² , Rings A, X and Y are as defined above. Z ¹ and Z ² each independently represent a group selected from the following substituent group (the following substituent group A or the following substituent group B).

In the formula (2M), a, b, R ⁴ , R ⁵ , R ⁶ and R ⁷ are as defined above. Z ³ and Z ⁴ each independently represent a group selected from the following substituent group (the following substituent group A or the following substituent group B).

In formula (3M), c, d, R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are as defined above. Z ⁵ and Z ⁶ each independently represent a group selected from the following substituent group (the following substituent group A or the following substituent group B).

In formula (4M), R ¹⁴ and R ¹⁵ are as defined above. Z ⁷ and Z ⁸ each independently represent a group selected from the following substituent group (the following substituent group A or the following substituent group B).

In the formula (5M), Ar ³ has the same meaning as described above. Z ¹⁵ and Z ¹⁶ represent a group selected from the following substituent group A or the following substituent group B.

In the formula (6M), a ¹ , a ² , Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , R ^C , R ^D and R ^E are as defined above. Z ¹⁷ and Z ¹⁸ represent a group selected from the following substituent group A or the following substituent group B.

In formula (7M), R ^F and Z are as defined above. Z ¹⁹ and Z ²⁰ represent a group selected from the following substituent group A or the following substituent group B.

Wherein (8M), na, nb, nA, n, Ar 8, L a, L b, L A and X 'are as defined ^{above, Z 13} and ^{Z 14} are the following substituent group A or Substituent A group selected from group B is shown.

<Substituent group A>
Hydrogen atom, chlorine atom, bromine atom, iodine atom,
A group represented by —O—S (═O) ₂ R ⁴¹ (R ⁴¹ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group). The group selected from the substituent group A is preferably a group other than a hydrogen atom.

<Substituent group B>
-B (OR ⁴² ) ₂ (R ⁴² represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ⁴² may be the same or different from each other and are linked to each other to form a ring structure. Or a group represented by
A group represented by -BF ₄ Q ¹ (Q ¹ represents a monovalent cation selected from the group consisting of Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ and Cs ⁺ );
A group represented by —MgY ¹ (Y ¹ represents a chlorine atom, a bromine atom or an iodine atom); a group represented by —ZnY ² (Y ² represents a chlorine atom, a bromine atom or an iodine atom); and,
—Sn (R ⁴³ ) ₃ (R ⁴³ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ⁴³ may be the same as or different from each other, and are linked to each other to form a ring structure. Or a group represented by

The definition and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ⁴¹ are R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2. This is the same as the definition and examples of the substituted alkyl group and the unsubstituted or substituted aryl group.

Definitions and examples of unsubstituted or substituted alkyl groups represented by R ⁴² include definitions and examples of unsubstituted or substituted alkyl groups represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2. Is the same.

Definitions and examples of unsubstituted or substituted alkyl groups represented by R ⁴³ include definitions and examples of unsubstituted or substituted alkyl groups represented by R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2. Is the same.

  A compound having a group selected from Substituent Group A and a compound having a group selected from Substituent Group B are subjected to condensation polymerization by a known coupling reaction, and a group selected from Substituent Group A and Substituent Group B It is known that carbon atoms bonded to a group selected from: are bonded to each other. Therefore, if the compound A having two groups selected from the substituent group A and the compound B having two groups selected from the substituent group B are subjected to a known coupling reaction, the compound is obtained by condensation polymerization. A condensation polymer of A and compound B can be obtained.

For example, when Z ¹ and Z ² in the compound represented by the formula (1-1-M) and Z ³ and Z ⁴ in the compound represented by the formula (2M) are groups selected from the substituent group A, As the Z ⁵ and Z ⁶ (or Z ⁷ and Z ⁸ ) in the compound represented by 3M) (or the compound represented by the formula (4M)), a group selected from the substituent group B can be selected. .
In addition, when Z ¹ and Z ² in the compound represented by the formula (1-1-M) and Z ³ and Z ⁴ in the compound represented by the formula (2M) are groups selected from the substituent B group, As the Z ⁵ and Z ⁶ (or Z ⁷ and Z ⁸ ) in the compound represented by 3M) (or the compound represented by the formula (4M)), a group selected from the substituent group A can be selected. .

  The compounds represented by formula (1-1-M), formula (1-2-M), formula (1-3-M) and formula (2M) to formula (8M) are synthesized and isolated in advance. They may be used or prepared in a reaction system and used as they are, but it is preferable to use those synthesized and isolated in advance.

  As a method of condensation polymerization, a compound represented by formula (1-1-M), formula (1-2-M), formula (1-3-M) and formula (2M) to formula (8M) is appropriately used. And a reaction method using a suitable catalyst or a suitable base.

  Catalysts include palladium such as dichlorobis (triphenylphosphine) palladium, dichlorobis (tris-o-methoxyphenylphosphine) palladium, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, and palladium acetate. Transition metal complexes such as nickel complexes such as nickel [tetrakis (triphenylphosphine)], [1,3-bis (diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel And a catalyst comprising a ligand such as triphenylphosphine, tri (tert-butylphosphine), tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl, etc., if necessary. A catalyst synthesized in advance can be used, or a catalyst prepared in a reaction system can be used as it is. These catalysts may be used alone or in combination of two or more.

  When a catalyst is used, the amount used is represented by formula (1-1-M), formula (1-2-M), formula (1-3-M) and formula (2M) to formula (8M). The amount of transition metal relative to the total number of moles of the compound to be obtained is preferably 0.00001 to 3 molar equivalents, more preferably 0.00005 to 0.5 molar equivalents, and still more preferably 0.0001 to 0.2 molar equivalents.

  Bases include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide, tetrahydroxide hydroxide An organic base such as butylammonium may be mentioned. These bases may be used alone or in combination of two or more.

  When a base is used, the amount used is shown by the formula (1-1-M), the formula (1-2-M), the formula (1-3-M) and the formula (2M) to the formula (8M). 0.5-20 molar equivalent is preferable with respect to the total number of moles of the compound to be obtained, and 1-10 molar equivalent is more preferable.

  The condensation polymerization can usually be performed in the presence of a solvent such as an organic solvent.

  The organic solvent varies depending on the type and reaction of the compound represented by formula (1-1-M), formula (1-2-M), formula (1-3-M), and formula (2M) to formula (8M). Are, for example, toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, N, N-dimethylformamide. In order to suppress side reactions, it is desirable to perform deoxygenation treatment on these solvents. These organic solvents may be used alone or in combination of two or more.

  The amount of the organic solvent used is the total concentration of the compounds represented by formula (1-1-M), formula (1-2-M), formula (1-3-M) and formula (2M) to formula (8M). However, the amount is usually 0.1 to 90% by weight, preferably 1 to 50% by weight, more preferably 2 to 30% by weight.

  The reaction temperature of the condensation polymerization is preferably -100 to 200 ° C, more preferably -80 to 150 ° C, and further preferably 0 to 120 ° C. The reaction time depends on conditions such as reaction temperature, but is usually 1 hour or longer, preferably 2 to 500 hours.

In the polymerization reaction, a compound represented by the following formula (1T) is used as a polymerization terminator to avoid leaving a polymerizable group (for example, Z ¹ or Z ² ) at the terminal of the polymer compound of the present embodiment. It may be used. As a result, a polymer compound whose terminal is an aryl group or a monovalent heterocyclic group (particularly a monovalent aromatic heterocyclic group) can be obtained.
Z ^T -Ar ^T (1T)

In formula (1T), Ar ^T represents an unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent heterocyclic group (particularly, an unsubstituted or substituted monovalent aromatic heterocyclic group);
Z ^T represents a group selected from the group consisting of the substituent group A and the substituent group B.
As the unsubstituted or substituted aryl group and the unsubstituted or substituted monovalent heterocyclic group (particularly, the unsubstituted or substituted monovalent aromatic heterocyclic group) in Ar ^T , the above-mentioned R ¹ and R ^{2 can be used.} , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 , and unsubstituted or substituted aryl groups and unsubstituted or substituted monovalent heterocyclic groups (particularly, unsubstituted or substituted monovalent aromatic groups) Group heterocyclic group).

  The post-treatment of the polymerization reaction can be carried out by a known method, for example, a method of removing water-soluble impurities by liquid separation, or a precipitate precipitated by adding the reaction solution after the polymerization reaction to a lower alcohol such as methanol. The method of filtering and drying can be performed alone or in combination.

  When the purity of the polymer compound of this embodiment is low, the polymer compound of this embodiment may be purified by ordinary methods such as recrystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, etc. When a compound is used for a light-emitting element, the purity affects the characteristics of the light-emitting element such as luminous efficiency and luminance life, and therefore, it is preferable to perform purification treatment such as reprecipitation purification and fractionation by chromatography after condensation polymerization.

  Examples of the condensation polymerization include polymerization by Suzuki reaction (Chem. Rev., Vol. 95, p. 2457 (1995)), polymerization by Grignard reaction (Kyoritsu Shuppan, polymer function). Material Series Volume 2, Polymer Synthesis and Reaction (2), pages 432-433), Method of Polymerization by Yamamoto Polymerization (Prog. Polym. Sci.), Volume 17, 1153-1205 Page, 1992).

[Compound]
The compound of the present invention is a compound represented by the following formula (1-1-M), (1-2-M) or (1-3-M), and is suitable as a raw material compound of the polymer compound of the present invention. Can be used.

In formula (1-1-M) to formula (1-3-M), R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ^A , R ^B , Ar ¹ , Ar ² , Rings A, X and Y are as defined above. Z ¹ and Z ² each independently represent a group selected from the above substituent group (the above substituent group A or the above substituent group B).

  The compound represented by the formula (1-1-M), the compound represented by the formula (1-2-M), and the compound represented by the formula (1-3-M) are a polymer compound of the present embodiment. Since the luminance lifetime of the light-emitting device produced using is more excellent, a compound represented by the following formula (1-1-AM), a compound represented by the following formula (1-2-AM), and A compound represented by the following formula (1-3-AM) is preferred. Among the compounds represented by the following formula (1-1-AM), compounds represented by the following formula (1-1-BM) are preferable, and are represented by the following formula (1-2-AM). Among these compounds, compounds represented by the following formula (1-2B-M) are preferable.

In formula (1-1-AM) to formula (1-3-AM), X, Y, R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ²³ , R ²⁴ , R ²⁵ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above, and Z ¹ and Z ² are each independently the above substituent group (the above substituent group A or the following substituent group). A group selected from group B);

In formula (1-1-BM), R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ²³ , R ²⁴ , R ²⁵ , R ²⁶ , R ²⁷ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above, and Z ¹ and Z ² each independently represent a group selected from the above substituent group (the above substituent group A or the following substituent group B). .

In formula (1-2-B-M), R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ²³ , R ²⁴ , R ²⁵ , R ²⁸ , R ²⁹ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above, and Z ¹ and Z ² each independently represent a group selected from the above substituent group (the above substituent group A or the following substituent group B).

  Here, the production method of the compound represented by the formula (1-1-BM) will be specifically described. The compound represented by the formula (1-1-BM) can be produced, for example, by the method described in Scheme 1 below.

スキーム１

Scheme 1

In Scheme 1, R ^1a represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group. A plurality of R ^1a may be the same or different.
R ^2a and R ^3a each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or A substituted monovalent heterocyclic group is shown.
R ^4a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ^1a represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Y ^1a and Y ^2a each independently represent a chlorine atom, a bromine atom or an iodine atom. However, Y ^1a and Y ^2a are different from each other, and Y ^2a represents an atom having a larger atomic number than Y ^1a .

The definition and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ^1a are the same as the definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ^41. It is.

R ^2a and R ^3a represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, and an unsubstituted or substituted monovalent heterocyclic ring The definition and examples of the group include an unsubstituted or substituted alkyl group represented by R ²⁶ and R ²⁷ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, and an unsubstituted or substituted group. The definition and examples of the substituted monovalent heterocyclic group are the same.

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group represented by R ^4a are the substituted alkyl group represented by R ^A and R ^B , The definition and examples are the same as those of the substituted or substituted aryl group and the unsubstituted or substituted monovalent heterocyclic group.

The definition and examples of the unsubstituted or substituted arylene group represented by Ar ^1a and the unsubstituted or substituted divalent heterocyclic group include the unsubstituted or substituted arylene group represented by Ar ¹ and Ar ² and the unsubstituted or substituted 2 The definition and example of the valent heterocyclic group are the same.

Y ^1a is preferably a chlorine atom or a bromine atom, and more preferably a bromine atom.

Y ^2a is preferably a bromine atom or an iodine atom, and more preferably an iodine atom.

  In Scheme 1, first, a compound represented by the formula (1-1-B-1) (hereinafter referred to as “compound (1-1-B-1)”, the same shall apply hereinafter), for example, It can be synthesized according to the method described in Japanese Patent No. 169265.

  Next, compound (1-1-B-2) is obtained by subjecting compound (1-1-B-1) and a predetermined amine compound to a known coupling reaction.

  Next, compound (1-1-B-3) is obtained by subjecting compound (1-1-B-2) and a predetermined amine compound to a known coupling reaction. In addition, compound (1-1-B-3) can also be converted to a group selected from substituent group B using a known reaction.

[Composition]
The composition of the present invention is a composition containing the polymer compound of the present invention and at least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material. This composition can be used, for example, as a light emitting material or a charge transport material (meaning a hole transport material and an electron transport material).

  Examples of the hole transport material, the electron transport material, and the light emitting material include a hole transport material, an electron transport material, and a light emitting material that can be included in an organic layer included in a light emitting element described later.

  The composition of the present invention may be a composition containing the polymer compound of the present invention and a solvent. This composition may be called a solution, an ink, or an ink composition, and is hereinafter referred to as “the solution of the present invention”.

  The solution of the present invention is useful for production of a light-emitting element by application of a printing method typified by an ink jet printing method. In addition to the polymer compound and the solvent, the solution of the present invention includes a hole transport material, an electron transport material, a light emitting material, a stabilizer, a thickener (a high molecular weight compound or a poor solvent for increasing viscosity), a viscosity. May contain a low molecular weight compound, a surfactant (for lowering the surface tension), an antioxidant and the like.

  The content ratio of the solvent in the solution of the present invention is usually 0.1 to 100,000 mass%, preferably 100 to 100,000 mass%, more preferably 1500 to 100 mass% of the polymer compound of the present invention. It is 50000 mass%, More preferably, it is 2000-20000 mass%.

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

  The high molecular weight compound used as the thickener may be any compound that is soluble in the same solvent as the high molecular compound and does not inhibit light emission or charge transport. For example, high molecular weight polystyrene or high molecular weight polymethyl methacrylate can be used. These high molecular weight compounds preferably have a polystyrene equivalent weight average molecular weight of 500,000 or more, more preferably 1,000,000 or more.

  A poor solvent can also be used as a thickener. By adding a small amount of a poor solvent for the solid content in the solution of the present invention, the viscosity can be increased. When a poor solvent is added for this purpose, the type and addition amount of the solvent may be selected as long as the solid content in the solution does not precipitate. Considering the stability during storage, the amount of the poor solvent is preferably 50% by mass or less, more preferably 30% by mass or less, with respect to 100% by mass of the whole solution.

  The antioxidant is for improving the storage stability of the solution of the present invention. The antioxidant is not particularly limited as long as it is soluble in the same solvent as the polymer compound and does not inhibit light emission or charge transport. Examples thereof include phenolic antioxidants and phosphorus antioxidants.

  The solvent of the solution of the present invention is preferably one that can dissolve or uniformly disperse the solid components in the solution. Examples of the solvent include chlorine solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, and ether solvents such as tetrahydrofuran, dioxane, anisole and 4-methylanisole. , Toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene and other aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane Aliphatic hydrocarbon solvents such as n-decane, ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, benzophenone, acetophenone, ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, phenyl acetate Ester solvents such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol Polyhydric alcohols and derivatives thereof, alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol, sulfoxide solvents such as dimethyl sulfoxide, amides such as N-methyl-2-pyrrolidone and N, N-dimethylformamide And system solvents. These solvents may be used alone or in combination of two or more.

  Among these, the solubility of polymer compounds, uniformity during film formation, viscosity characteristics, etc. can be improved, so aromatic hydrocarbon solvents, ether solvents, aliphatic hydrocarbon solvents, ester solvents, ketones Preferred solvents are toluene, xylene, ethylbenzene, diethylbenzene, trimethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzene, isobutylbenzene, sec-butylbenzene, n-hexylbenzene, cyclohexylbenzene, 1-methylnaphthalene, Tetralin, anisole, 4-methylanisole, ethoxybenzene, cyclohexane, bicyclohexyl, cyclohexenylcyclohexanone, n-heptylcyclohexane, n-hexylcyclohexane, decalin, methyl benzoate, cyclohexanone, - propyl cyclohexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, 2-nonanone, 2-decanone, dicyclohexyl ketone, acetophenone, benzophenone more preferable.

  Since a film formability etc. become favorable, it is preferable to use 2 or more types in combination, more preferable to use 2 to 3 types in combination, and particularly preferable to use 2 types in combination.

When two kinds of solvents are contained in the solution of the present invention, one of the solvents may be in a solid state at 25 ° C. Since the film formability and the like are improved, the one kind of solvent is preferably a solvent having a boiling point of 180 ° C. or higher, more preferably 200 ° C. or higher. Moreover, since favorable viscosity is obtained, it is preferable that the polymer compound is dissolved at a concentration of 1% by mass or more at 60 ° C. in either of the two solvents. It is preferable that the polymer compound dissolves at a concentration of 1% by mass or more at 25 ° C.
When two or more kinds of solvents are contained in the solution of the present invention, the solvent having the highest boiling point is 40 to 90% by mass of 100% by mass of the total solvent in the solution in order to obtain good viscosity and film formability. %, More preferably 50 to 90% by mass, and still more preferably 65 to 85% by mass.

  The polymer compound of the present invention contained in the solution of the present invention may be one type or two or more types. Moreover, high molecular weight compounds other than the high molecular compound of this invention may be included.

  The solution of the present invention may contain water, metal and a salt thereof in the range of 1 to 1000 ppm by weight. Examples of the metal include lithium, sodium, calcium, potassium, iron, copper, nickel, aluminum, zinc, chromium, manganese, cobalt, platinum, iridium and the like. The solution of the present invention may contain silicon, phosphorus, fluorine, chlorine, bromine and the like in a range of 1 to 1000 ppm on a weight basis.

[Organic thin film]
The organic thin film of the present invention contains the polymer compound of the present invention, and may contain the composition of the present invention. The organic thin film of this embodiment is a light emitting thin film, a conductive thin film, or an organic semiconductor thin film, for example.

The organic thin film of the present embodiment can be easily produced from the solution of the present embodiment.
The second organic thin film of the present embodiment is an insolubilized organic thin film obtained by insolubilizing the polymer compound of the present embodiment by crosslinking, and is usually crosslinked and cured by external stimulation such as heating or light irradiation. It is. Since the insolubilized organic thin film is hardly soluble in a solvent, it is advantageous for stacking light emitting elements.

  The heating for crosslinking the organic thin film is not particularly limited, but is generally in the range of room temperature to 300 ° C., and the upper limit is preferably 250 ° C. from the viewpoint of luminous efficiency, and 200 ° C. More preferably, it is particularly preferably 180 ° C. Further, the lower limit is preferably 50 ° C., more preferably 70 ° C., and particularly preferably 100 ° C. from the viewpoint of easy formation of the insolubilized organic thin film.

  The light irradiation for crosslinking the organic thin film is not particularly limited, but generally, ultraviolet light, near ultraviolet light, and visible light are used, but ultraviolet light and near ultraviolet light are preferable.

  The organic thin film and insolubilized organic thin film of the present embodiment can be suitably used as a light emitting layer, a hole transport layer, a hole injection layer, or an interlayer layer in a light emitting device to be described later. Moreover, it can be used conveniently also for organic semiconductor elements, such as an organic transistor and an organic solar cell.

  The thin film of the present invention is, for example, a spin coating method, a casting method, a micro gravure coating method, a gravure coating method, a bar coating method, a roll coating method, a wire bar coating method, a dip coating method, a spray coating method, a screen printing method, a flexographic method. It can be produced by a printing method, an offset printing method, an ink jet printing method, a capillary coating method, or a nozzle coating method. Preferably, it can be produced by a screen printing method, a flexographic printing method, an offset printing method, an ink jet printing method, more preferably an ink jet printing method.

  When the organic thin film of the present invention is produced using the above-described solution of the present invention, the polymer compound of the present invention contained in the solution has a high glass transition temperature, so that it can be heated at a temperature of 100 ° C. or higher. Even when heated at a temperature of 130 ° C., the degradation of device characteristics is small. Further, depending on the type of the polymer compound, heating can be performed at a temperature of 160 ° C. or higher.

  Since the light emitting thin film has a good driving voltage of the light emitting element, the emission quantum yield is preferably 30% or more, more preferably 50% or more, and further preferably 60% or more, It is especially preferable that it is 70% or more.

  The conductive thin film preferably has a surface resistance of 1 KΩ / □ or less, more preferably 100Ω / □ or less, and even more preferably 10Ω / □ or less. The electrical conductivity can be increased by doping the conductive thin film with a Lewis acid, an ionic compound or the like.

The organic semiconductor thin film preferably has a higher electron mobility or hole mobility of 1 × 10 ⁻⁵ cm ² / V · s or more, preferably 1 × 10 ⁻³ cm ² / V · s or more. It is more preferable that it is 1 × 10 ⁻¹ cm ² / V · s or more. An organic transistor can be obtained by forming an organic semiconductor thin film on a Si substrate on which an insulating film such as SiO ₂ and a gate electrode are formed, and forming a source electrode and a drain electrode with Au or the like.

[Light emitting element]
Next, the light emitting device of the present invention will be described.

  The light emitting device of the present invention is a light emitting device having an electrode comprising an anode and a cathode and a layer containing the polymer compound of the present invention provided between the electrodes, and a layer containing the composition of the present invention. It may be. Here, the layer containing the polymer compound is preferably a layer made of the organic thin film or the insolubilized organic thin film of the present invention.

The layer containing the polymer compound of the present invention is preferably one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, an electron injection layer and an interlayer layer. More preferably, it is one or more layers of a hole transport layer, a hole injection layer and an interlayer layer, and more preferably one or more layers of a light emitting layer, a hole transport layer and an interlayer layer. Particularly preferred is one or more of a light emitting layer and an interlayer layer.
In addition, when the layer containing the polymer compound of the present invention functions as a hole transport layer, a hole injection layer, or an interlayer layer, the layer is preferably a layer made of the insolubilized organic thin film of the present invention.

  The light emitting layer means a layer having a function of emitting light. The hole transport layer means a layer having a function of transporting holes. The electron transport layer means a layer having a function of transporting electrons. The interlayer layer is adjacent to the light emitting layer between the light emitting layer and the anode, and is a layer that plays a role of separating the light emitting layer and the anode or the light emitting layer from the hole injection layer or the hole transport layer. That is. The electron transport layer and the hole transport layer are collectively referred to as a charge transport layer, and the electron injection layer and the hole injection layer are collectively referred to as a charge injection layer. Each of the light emitting layer, the hole transport layer, the hole injection layer, the electron transport layer, the electron injection layer and the interlayer layer may be composed of only one layer or two or more layers.

  When the layer containing a polymer compound is a light emitting layer, the light emitting layer may further contain at least one material selected from the group consisting of a hole transport material, an electron transport material and a light emitting material. Here, the light emitting material means a material exhibiting fluorescence and / or phosphorescence (however, different from the polymer compound of the present invention).

  When the layer containing the polymer compound contains the polymer compound of the present invention and the hole transport material, the content ratio of the hole transport material with respect to 100 parts by mass of the polymer compound of the present invention is: Usually, it is 1-400 mass parts, Preferably it is 5-150 mass parts.

  When the layer containing the polymer compound contains the polymer compound of the present invention and the electron transport material, the content ratio of the electron transport material is usually 100 parts by mass of the polymer compound of the present invention. 1 to 400 parts by mass, preferably 5 to 150 parts by mass.

  When the layer containing the polymer compound contains the polymer compound of the present invention and the light emitting material, the content ratio of the light emitting material is usually 1 to 100 parts by mass of the polymer compound of the present invention. 400 parts by mass, preferably 5 to 150 parts by mass.

  As the hole transport material, the electron transport material, and the light emitting material, known low molecular weight compounds, triplet light emitting complexes, and high molecular weight compounds can be used.

  High molecular weight compounds include WO99 / 13692, WO99 / 48160, GB2340304A, WO00 / 53656, WO01 / 19834, WO00 / 55927, GB2348316, WO00 / 46321, WO00 / 06665, WO99 / 54943, WO99 / 54385, US5777070, WO98. / 06773, WO97 / 05184, WO00 / 35987, WO00 / 53655, WO01 / 34722, WO99 / 24526, WO00 / 22027, WO00 / 22026, WO98 / 27136, US573636, WO98 / 21262, US5741921, WO97 / 09394, WO96 / 29356 , WO 96/10617, EP 0707020, WO 95/07955, JP-A-2001-2001. 81618, JP 2001-123156, JP 2001-3045, JP 2000-351967, JP 2000-303066, JP 2000-299189, JP 2000-252065. JP, 2000-136379, JP 2000-104057, JP 2000-80167, JP 10-324870, JP 10-114891, JP 9-111233, Polymers and copolymers having a fluorenediyl group as a constituent unit described in JP-A-9-45478 (hereinafter referred to as “(co) polymer”). ), (Co) polymer having an arylene group as a structural unit, (co) polymer having an arylene vinylene group as a structural unit The divalent aromatic amine group as a constituent unit (co) polymer and the like.

  Examples of the low molecular weight compounds include naphthalene derivatives, anthracene and derivatives thereof, perylene and derivatives thereof, polymethine-based, xanthene-based, coumarin-based, cyanine-based pigments, 8-hydroxyquinoline and its metal complexes, aromatic amines , Tetraphenylcyclopentadiene and derivatives thereof, and tetraphenylbutadiene and derivatives thereof. Specific examples include compounds described in JP-A-57-51781 and JP-A-59-194393.

As the triplet light-emitting complex, Ir (ppy) ₃ having iridium as a central metal, Btp ₂ Ir (acac), FIrpic, ADS066GE commercially available from American Dye Source, Inc., platinum as a central metal PtOEP and Eu (TTA) ₃ phen with europium as the central metal. Specifically, Nature, (1998), 395, 151, Appl. Phys. Lett. (1999), 75 (1), 4, Proc. SPIE-Int. Soc. Opt. Eng. (2001), 4105 (Organic Light-Emitting Materials and Devices IV), 119, J. MoI. Am. Chem. Soc. , (2001), 123, 4304, Appl. Phys. Lett. , (1997), 71 (18), 2596, Syn. Met. (1998), 94 (1), 103, Syn. Met. (1999), 99 (2), 1361, Adv. Mater. (1999), 11 (10), 852, Jpn. J. et al. Appl. Phys. , 34, 1883 (1995).

  The triplet light-emitting complex can also be used by bonding to the main chain, side chain, and terminal of the polymer compound of the present invention.

  The thickness of the light emitting layer has an optimum value depending on the material used, and may be selected so that the driving voltage and the light emission efficiency are appropriate. Usually, it is 1 nm-1 micrometer, Preferably it is 2 nm-500 nm, More preferably, it is 5 nm-200 nm, More preferably, it is 50 nm-150 nm.

  Examples of the method for forming the light emitting layer include a method by film formation from a solution. For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used. Among these, a printing method such as a screen printing method, a flexographic printing method, an offset printing method, and an ink jet printing method is preferable because pattern formation and multi-color coating can be easily performed.

  Solvents used for film formation from solution include chlorine solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene, and ether solvents such as tetrahydrofuran and dioxane. , Toluene, xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene, anisole, 4-methylanisole and other aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, Aliphatic hydrocarbon solvents such as n-octane, n-nonane and n-decane, ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol Polyhydric alcohols and derivatives thereof such as ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, Examples include alcohol solvents such as methanol, ethanol, propanol, isopropanol and cyclohexanol, sulfoxide solvents such as dimethyl sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  As a light emitting element, a light emitting element in which an electron transport layer is provided between the cathode and the light emitting layer, a light emitting element in which a hole transport layer is provided between the anode and the light emitting layer, and an electron transport between the cathode and the light emitting layer. A light emitting element in which a layer is provided and a hole transport layer is provided between the anode and the light emitting layer can be given.

Examples of the structure of such a light emitting device include the following structures a) to d).
a) Anode / light emitting layer / cathode b) Anode / hole transport layer / light emitting layer / cathode c) Anode / light emitting layer / electron transport layer / cathode d) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (Here, / indicates that each layer is laminated adjacently. The same shall apply hereinafter.)

For each of these structures, an interlayer layer may be provided adjacent to the light emitting layer between the light emitting layer and the anode. Examples of the structure of such a light emitting device include the following structures a ′) to d ′).
a ′) Anode / interlayer layer / light emitting layer / cathode b ′) Anode / hole transport layer / interlayer layer / light emitting layer / cathode c ′) Anode / interlayer layer / light emitting layer / electron transport layer / cathode d ′ ) Anode / hole transport layer / interlayer layer / light emitting layer / electron transport layer / cathode

  When the light emitting element has a hole transport layer, the hole transport layer usually contains a hole transport material (a high molecular weight compound, a low molecular weight compound). Examples of hole transport materials include polyvinylcarbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having aromatic amines in the side chain or main chain, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, polyanilines and Derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, and JP-A 63-70257, 63 Examples described in JP-A-175860, JP-A-2-135359, JP-A-2-135361, JP-A-2-209988, JP-A-3-37992, and JP-A-3-152184 are exemplified. .

  Among these, high molecular weight compounds include polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane derivatives having an aromatic amine compound group in the side chain or main chain, polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (P-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof are preferred, polyvinyl carbazole and derivatives thereof, polysilane and derivatives thereof, polysiloxane having an aromatic amine in the side chain or main chain Derivatives are more preferred.

  Moreover, as a low molecular weight compound, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, and a triphenyldiamine derivative are preferable. These low molecular weight compounds are preferably used by being dispersed in a polymer binder.

  As the polymer binder, a compound that does not extremely inhibit charge transport and does not strongly absorb visible light is preferable. For example, poly (N-vinylcarbazole), polyaniline and derivatives thereof, polythiophene and derivatives thereof, poly (p-phenylene vinylene) and derivatives thereof, poly (2,5-thienylene vinylene) and derivatives thereof, polycarbonate, polyacrylate, Examples include polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, and polysiloxane.

  Polyvinylcarbazole and derivatives thereof can be obtained, for example, by cationic polymerization or radical polymerization of a vinyl monomer.

  Examples of the polysilane and derivatives thereof include the compounds described in Chem. Rev. 89, 1359 (1989), GB 2300196 published specification. As the synthesis method, methods described in these can be used, but the Kipping method is particularly preferably used.

  As the polysiloxane and derivatives thereof, since the structure derived from siloxane has almost no hole transporting property, a compound having a structure of a low molecular weight hole transporting material in the side chain or main chain is preferable, and the hole transporting property is preferable. A compound having a structure derived from an aromatic amine in the side chain or main chain is more preferred.

  As a method of forming the hole transport layer, when a low molecular weight compound is used, a method of forming a film from a mixed solution with a polymer binder is exemplified. In the case of using a high molecular weight compound, a method by film formation from a solution is exemplified.

  As a solvent used for film formation from a solution, a solvent capable of dissolving or uniformly dispersing the hole transport material is preferable. Solvents include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene, mesitylene, Aromatic hydrocarbon solvents such as ethylbenzene, n-hexylbenzene, cyclohexylbenzene, anisole, 4-methylanisole, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane Aliphatic hydrocarbon solvents such as n-decane, ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol Polyhydric alcohols such as butyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol and derivatives thereof, methanol, ethanol And alcohol solvents such as propanol, isopropanol and cyclohexanol, sulfoxide solvents such as dimethyl sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used.

  The thickness of the hole transport layer differs depending on the material used and may be selected so that the drive voltage and luminous efficiency are appropriate. However, the thickness should be such that pinholes do not occur. Usually, it is 1 nm to 1 μm, preferably 2 to 500 nm, more preferably 5 to 200 nm.

  When the light emitting element has an electron transport layer, the electron transport layer usually contains an electron transport material (a high molecular weight compound, a low molecular weight compound). A well-known thing can be used as an electron transport material. For example, oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, Diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof, JP-A 63-70257, JP-A 63-175860, As described in JP-A-2-135359, JP-A-2-135361, JP-A-2-209998, JP-A-3-37992, and JP-A-3-152184. That compounds. Of these, oxadiazole derivatives, benzoquinone and derivatives thereof, anthraquinone and derivatives thereof, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof are preferable. More preferred are (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8-quinolinol) aluminum, and polyquinoline.

  Examples of the film forming method for the electron transport layer include a vacuum deposition method from a powder or a film forming method from a solution or a molten state when a low molecular weight compound is used. In the case of using a high molecular weight compound, a method of film formation from a solution or a molten state is exemplified. In the method by film formation from a solution or a molten state, the above polymer binder may be used in combination.

  The solvent used for film formation from a solution is preferably a solvent that can dissolve or uniformly disperse the electron transport material and / or the polymer binder. Solvents include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene, mesitylene, Aromatic hydrocarbon solvents such as ethylbenzene, n-hexylbenzene, cyclohexylbenzene, anisole, 4-methylanisole, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane Aliphatic hydrocarbon solvents such as n-decane, ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol Polyhydric alcohols such as butyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol and derivatives thereof, methanol, ethanol And alcohol solvents such as propanol, isopropanol and cyclohexanol, sulfoxide solvents such as dimethyl sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  For film formation from solution or molten state, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing A coating method such as a method, a flexographic printing method, an offset printing method, an ink jet printing method, a capillary coating method, or a nozzle coating method can be used.

  The thickness of the electron transport layer varies depending on the material used and may be selected so that the drive voltage and the light emission efficiency are appropriate values. Usually, it is 1 nm-1 micrometer, Preferably it is 2-500 nm, More preferably, it is 5-200 nm.

  The hole injection layer and the electron injection layer have a function of improving the charge injection efficiency from the electrode among the charge transport layers provided adjacent to the electrode, and have the effect of lowering the driving voltage of the light emitting element. .

  In order to improve adhesion with the electrode and charge injection from the electrode, a charge injection layer or an insulating layer adjacent to the electrode (usually 0.5 to 4.0 nm in average thickness, hereinafter the same) May be provided). In addition, a thin buffer layer may be inserted at the interface between the charge transport layer and the light emitting layer in order to improve adhesion at the interface and prevent mixing.

  The order and number of layers to be stacked and the thickness of each layer may be adjusted in consideration of light emission efficiency and element lifetime.

In this embodiment, examples of the light emitting element provided with the charge injection layer include a light emitting element provided with the charge injection layer adjacent to the cathode and a light emitting element provided with the charge injection layer adjacent to the anode. Examples of the structure of such a light emitting device include the following structures e) to p).
e) Anode / charge injection layer / light emitting layer / cathode f) Anode / light emitting layer / charge injection layer / cathode g) Anode / charge injection layer / light emitting layer / charge injection layer / cathode h) Anode / charge injection layer / hole Transport layer / light emitting layer / cathode i) anode / hole transport layer / light emitting layer / charge injection layer / cathode j) anode / charge injection layer / hole transport layer / light emitting layer / charge injection layer / cathode k) anode / charge Injection layer / light emitting layer / electron transport layer / cathode l) anode / light emitting layer / electron transport layer / charge injection layer / cathode m) anode / charge injection layer / light emitting layer / electron transport layer / charge injection layer / cathode n) anode / Charge injection layer / hole transport layer / light emitting layer / electron transport layer / cathode o) anode / hole transport layer / light emitting layer / electron transport layer / charge injection layer / cathode p) anode / charge injection layer / hole transport Layer / light emitting layer / electron transport layer / charge injection layer / cathode

  For each of these structures, a structure in which an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode is also exemplified. In this case, the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.

  The charge injection layer is a layer containing a conductive polymer, provided between the anode and the hole transport layer, and has an ionization potential of an intermediate value between the anode material and the hole transport material contained in the hole transport layer. Examples thereof include a layer including a material having a material, a layer including a material provided between the cathode and the electron transport layer, and having a material having an intermediate electron affinity between the cathode material and the electron transport material included in the electron transport layer.

When the charge injection layer is a layer containing a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × 10 ⁻⁵ to 1 × 10 ³ S / cm, and further a leakage current between the light emitting pixels. 1 × 10 ⁻⁵ to 1 × 10 ² S / cm is more preferable, and 1 × 10 ⁻⁵ to 1 × 10 ¹ S / cm is even more preferable. Usually, in order to make the electric conductivity of the conductive polymer within such a range, the conductive polymer is doped with an appropriate amount of ions.

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

  The material used for the charge injection layer may be selected in relation to the electrode and the material of the adjacent layer. Examples of materials used for the charge injection layer include polyaniline and derivatives thereof, polythiophene and derivatives thereof, polypyrrole and derivatives thereof, polyphenylene vinylene and derivatives thereof, polythienylene vinylene and derivatives thereof, polyquinoline and derivatives thereof, and polyquinoxaline and derivatives thereof. Examples thereof include conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain, metal phthalocyanines (such as copper phthalocyanine), and carbon.

  Examples of the material for the insulating layer include metal fluorides, metal oxides, and organic insulating materials. Examples of the light emitting element provided with an insulating layer include a light emitting element provided with an insulating layer adjacent to the cathode and a light emitting element provided with an insulating layer adjacent to the anode.

Examples of the structure of such a light emitting element include the following structures q) to ab).
q) anode / insulating layer / light emitting layer / cathode r) anode / light emitting layer / insulating layer / cathode s) anode / insulating layer / light emitting layer / insulating layer / cathode t) anode / insulating layer / hole transport layer / light emitting layer / Cathode u) anode / hole transport layer / light emitting layer / insulating layer / cathode v) anode / insulating layer / hole transport layer / light emitting layer / insulating layer / cathode w) anode / insulating layer / light emitting layer / electron transport layer / Cathode x) anode / light emitting layer / electron transport layer / insulating layer / cathode y) anode / insulating layer / light emitting layer / electron transport layer / insulating layer / cathode z) anode / insulating layer / hole transport layer / light emitting layer / Electron transport layer / cathode aa) anode / hole transport layer / light emitting layer / electron transport layer / insulating layer / cathode ab) anode / insulating layer / hole transport layer / light emitting layer / electron transport layer / insulating layer / cathode

  For each of these structures, a structure in which an interlayer layer is provided adjacent to the light emitting layer between the light emitting layer and the anode is also exemplified. In this case, the interlayer layer may also serve as a hole injection layer and / or a hole transport layer.

  When the interlayer layer is applied to the structures a) to ab) described above, the interlayer layer is provided between the anode and the light emitting layer, and constitutes the light emitting layer with the anode or the hole injection layer or the hole transport layer. It is preferably made of a material having an ionization potential intermediate to that of the polymer compound.

  Materials used for the interlayer layer include aromatic compounds such as the polymer compound of the present invention, polyvinylcarbazole and derivatives thereof, polyarylene derivatives having aromatic amines in the side chain or main chain, arylamine derivatives, and triphenyldiamine derivatives. Are exemplified. When the polymer compound of the present invention is used for an interlayer layer, it is preferably a layer composed of the above-described organic thin film or insolubilized organic thin film of the present invention, and more preferably a layer composed of the insolubilized organic thin film of the present invention.

  As a method for forming the interlayer layer, when a high molecular weight material is used, a method of forming a film from a solution can be used.

  As a solvent used for film formation from a solution, a solvent capable of dissolving or uniformly dispersing a material used for an interlayer layer is preferable. Solvents include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorinated solvents such as chlorobenzene and o-dichlorobenzene, ether solvents such as tetrahydrofuran and dioxane, toluene, xylene, mesitylene, Aromatic hydrocarbon solvents such as ethylbenzene, n-hexylbenzene, cyclohexylbenzene, anisole, 4-methylanisole, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane Aliphatic hydrocarbon solvents such as n-decane, ketone solvents such as acetone, methyl ethyl ketone and cyclohexanone, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol Polyhydric alcohols such as butyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol and derivatives thereof, methanol, ethanol And alcohol solvents such as propanol, isopropanol and cyclohexanol, sulfoxide solvents such as dimethyl sulfoxide, and amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. These solvents may be used alone or in combination of two or more.

  For film formation from solution, spin coating method, casting method, micro gravure coating method, gravure coating method, bar coating method, roll coating method, wire bar coating method, dip coating method, spray coating method, screen printing method, flexographic method Coating methods such as a printing method, an offset printing method, an ink jet printing method, a capillary coating method, and a nozzle coating method can be used.

  The thickness of the interlayer layer varies depending on the material used, and may be selected so that the drive voltage and the light emission efficiency are appropriate values. Usually, it is 1 nm-1 micrometer, Preferably it is 2-500 nm, More preferably, it is 5-200 nm.

  When the interlayer is provided adjacent to the light-emitting layer, particularly when both layers are formed by a coating method, the two layers of materials may be mixed to adversely affect the characteristics of the device. . When the light emitting layer is formed by the coating method after the interlayer layer is formed by the coating method, as a method of reducing the mixing of the two layers of materials, the interlayer layer is formed by the coating method, and this interlayer layer is heated. A method of forming a light emitting layer after insolubilization in an organic solvent used for preparing the light emitting layer is mentioned. The heating temperature is usually 150 to 300 ° C. The heating time is usually 1 minute to 1 hour. In this case, in order to remove components that have not been insolubilized by heating, the interlayer layer may be rinsed with a solvent used for forming the light emitting layer after heating and before forming the light emitting layer. When the solvent is insolubilized sufficiently by heating, rinsing can be omitted. In order to sufficiently insolubilize the solvent by heating, it is preferable to use a compound having a polymerizable group in the molecule as the high molecular weight compound used in the interlayer layer. More preferably, the polymer compound is in the form. Furthermore, the number of polymerizable groups is preferably 5 mol% or more based on the number of structural units in the molecule.

  The substrate in the light-emitting element may be any substrate that can form an electrode and does not change when an organic layer is formed. For example, what consists of materials, such as glass, a plastics, a polymer film, a silicon | silicone, is illustrated. In the case of an opaque substrate, the opposite electrode is preferably transparent or translucent.

  At least one of the anode and the cathode of the light emitting element is usually transparent or translucent, but the anode side is preferably transparent or translucent.

  Examples of the material for the anode include a conductive metal oxide film and a translucent metal thin film. Specifically, indium oxide, zinc oxide, tin oxide, and their composites, indium-tin-oxide (ITO), a film made using a conductive compound made of indium-zinc-oxide, etc., NESA, gold, platinum, silver, copper and the like are used. Of these, ITO, indium / zinc / oxide, and tin oxide are preferable. Examples of the production method include a vacuum deposition method, a sputtering method, an ion plating method, a plating method, and the like. As the anode, an organic transparent conductive film such as polyaniline and a derivative thereof, polythiophene and a derivative thereof may be used. Further, the anode may have a laminated structure of two or more layers.

  The thickness of the anode can be selected in consideration of light transmittance and electric conductivity. For example, it is 10 nm to 10 μm, preferably 20 nm to 1 μm, and more preferably 40 to 500 nm.

  In order to facilitate charge injection, a layer made of a phthalocyanine derivative, a conductive polymer, carbon, or the like, or an insulating layer made of a metal oxide, a metal fluoride, an organic insulating material, or the like may be provided on the anode.

  As a material for the cathode, a material having a small work function is preferable, lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, Europium, terbium, ytterbium and other metals, or two or more of them, or one or more of them, and one of gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten, tin Alloys with more than seeds, and graphite and graphite intercalation compounds are used. Examples of the alloy include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, and calcium-aluminum alloy. The cathode may have a laminated structure of two or more layers.

  The thickness of the cathode may be adjusted in consideration of electric conductivity and durability. Usually, the thickness is 10 nm to 10 μm, preferably 20 nm to 1 μm, more preferably 50 to 500 nm.

  As a method for producing the cathode, a vacuum deposition method, a sputtering method, a laminating method in which a metal thin film is thermocompression-bonded, or the like is used. Further, a layer made of a conductive polymer, or a metal oxide, a metal fluoride, an organic insulating material, or the like between the cathode and the organic layer (that is, any layer containing the polymer compound of the present invention). A layer having an average thickness of 2 nm or less may be provided, and a protective layer for protecting the light-emitting element may be attached after the cathode is manufactured. In order to use the light emitting element stably for a long period of time, it is preferable to attach a protective layer and / or a protective cover in order to protect the element from the outside.

  As the protective layer, high molecular weight compounds, metal oxides, metal fluorides, metal borides and the like can be used. As the protective cover, a metal plate, a glass plate, a plastic plate having a surface subjected to low water permeability treatment, or the like can be used. For example, a method in which the protective cover is bonded to the element substrate with a thermosetting resin or a photocurable resin and sealed is preferably used. If a space is maintained using a spacer, it is easy to prevent damage to the element. If an inert gas such as nitrogen or argon is sealed in this space, the oxidation of the cathode can be prevented. Furthermore, by installing a desiccant such as barium oxide in this space, it becomes easy to suppress the moisture absorbed in the manufacturing process or the minute amount of moisture entering through the cured resin from damaging the device. . Among these, it is preferable to take one or more measures.

  The light-emitting element is useful for a planar light source, a segment display device, a dot matrix display device, a backlight of a liquid crystal display device, and the like.

  In order to obtain planar light emission using the light emitting element, the planar anode and the cathode may be arranged so as to overlap each other. In addition, in order to obtain patterned light emission, a method of installing a mask having a patterned window on the surface of a planar light emitting element, a layer that is desired to be a non-light emitting portion is formed extremely thick and substantially non-light emitting And a method of forming an anode or a cathode, or both electrodes in a pattern. By forming a pattern by any of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display device capable of displaying numbers, letters, simple symbols, and the like can be obtained. Furthermore, in order to obtain a dot matrix display device, both the anode and the cathode may be formed in stripes and arranged so as to be orthogonal to each other. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors or a method using a color filter or a fluorescence conversion filter. The dot matrix display device can be driven passively or may be driven actively in combination with a TFT or the like. These display devices can be used in computers, televisions, mobile terminals, mobile phones, car navigation systems, video camera viewfinders, and the like.

  Further, the planar light-emitting element is a self-luminous thin type, and can be suitably used as a planar light source for a backlight of a liquid crystal display device or a planar illumination light source. If a flexible substrate is used, it can be used as a curved light source or display device.

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

[Method for measuring number average molecular weight and weight average molecular weight]
In this example, the polystyrene-equivalent number average molecular weight and weight average molecular weight were determined by gel permeation chromatography (hereinafter referred to as “GPC”) (manufactured by Shimadzu Corporation, trade name: LC-10Avp). The polymer compound to be measured was dissolved in tetrahydrofuran (hereinafter sometimes referred to as “THF”) to a concentration of about 0.5% by weight, and 30 μL was injected into GPC. Tetrahydrofuran was used for the mobile phase of GPC, and flowed at a flow rate of 0.6 mL / min. As for the column, two TSKgel SuperHM-H (manufactured by Tosoh) and one TSKgel SuperH2000 (manufactured by Tosoh) were connected in series. A differential refractive index detector (manufactured by Shimadzu Corporation, trade name: RID-10A) was used as the detector.

[Measurement method of LC-MS]
In this example, the LC-MS measurement was performed by the following method. The measurement sample was dissolved in chloroform or tetrahydrofuran to a concentration of about 2 mg / mL, and about 1 μL was injected into LC-MS (manufactured by Agilent Technologies, trade name: 1100LCMSD).
For the mobile phase of LC-MS, unless otherwise specified, acetonitrile and tetrahydrofuran were used 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 Chemicals Evaluation and Research Institute, inner diameter: 2.1 mm, length: 100 mm, particle size: 3 μm).

[Measurement method of NMR]
In this example, NMR measurement was performed by the following method. 5-10 mg of a measurement sample is dissolved in about 0.5 mL of deuterated chloroform or deuterated tetrahydrofuran, and NMR (manufactured by Varian, trade name: MERCURY 300, or Bruker, trade name: AVANCE 600 TCI cryoprobe) And measured.

<Synthesis Example 1: Synthesis of Compound 2>

  Compound 1 was synthesized according to the method described in JP-A No. 2006-169265.

  After making the inside of the reaction vessel a nitrogen gas atmosphere, 2,6-dimethyl-4-tert-butylaniline (8.5 g) was dissolved in toluene (135 ml), sodium tert-butoxide (4.6 g), tris Benzylideneacetone) dipalladium (0) (0.73 g) and 2-dicyclohexylphosphino-2 ′-(N, N-dimethylamino) biphenyl (1.26 g) were sequentially added. Then, the obtained reaction liquid was heated to 95 ° C., Compound 1 (10.44 g) was added, and the mixture was heated to reflux (3 hours). Then, it cooled to room temperature, toluene (100 ml) and water (150 ml) were added and stirred, and then the precoat process was performed and liquid-separated. Activated carbon (1.5 g) was added to the obtained organic layer, and the mixture was stirred at 60 ° C. for 30 minutes, then pre-coated, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: toluene / hexane = 1/2), and further crystallized from methanol (20 ml) to obtain 6.5 g of compound 2.

LC-MS (APCI, positive): [M + H] ⁺ 706

Example 1 Synthesis of Compound 3

  After the inside of the reaction vessel was filled with nitrogen gas, Compound 2 (5.99 g) was dissolved in xylene (72 ml), sodium tert-butoxide (3.26 g), tris (dibenzylideneacetone) dipalladium (0) (0 .16 g) and 1,1′-bis (diphenylphosphino) ferrocene (0.38 g) were sequentially added, and the temperature was raised to 100 ° C. Thereafter, iodobromobenzene (14.4 g) was added thereto, followed by stirring at 135 ° C. for 5 hours. Thereafter, the mixture was cooled to room temperature, toluene (100 ml) and water (150 ml) were added and stirred, followed by pre-coating treatment and liquid separation, followed by silica gel column chromatography (developing solvent: hexane / toluene mixed solution). The product solution was concentrated. The obtained residue was crystallized from isopropyl alcohol to obtain 4.5 g of a crude product. Furthermore, the crude product was dissolved in a mixed solvent of tetrahydrofuran and methanol, activated carbon (3.5 g) was added, and the mixture was stirred at room temperature for 1 hour. The resulting mixture was then filtered and concentrated. The obtained residue was crystallized twice with a mixed solvent of tetrahydrofuran and methanol to obtain 1.8 g of Compound 3.

LC-MS (APCI, positive): [M + H] ⁺ 1014
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.35-0.46 (m, 4H), 0.62 (d, 6H), 0.67 (d, 6H), 1 .25 (m, 2H), 1.37 (s, 9H), 1.38 (s, 9H), 2.09 (s, 12H), 2.14 (m, 2H), 2.42 (m, 2H), 6.87 (d, 2H), 6.87 (d, 1H), 6.94 (d, 2H), 7.22 (s, 2H), 7.25 (s, 2H), 7. 28 (d, 2H), 7.29 (s, 1H), 7.31 (d, 1H), 7.34 (d, 2H), 7.40 (d, 1H), 7.57 (d, 1H) ), 7.58 (d, 1H), 7.73 (d, 1H), 8.09 (d, 1H).

<Synthesis Example 2: Synthesis of Compound 5>

反応容器内を窒素ガス雰囲気とした後、１，５−ナフチルビス（トリフルオロメタンスルフォネート）（化合物４、２５．０ｇ）、[１，１'−ビス（ジフェニルホスフィノ）フェロセン]ジクロロパラジウム（ＩＩ）ジクロロメチレン付加体（０．２４ｇ）およびｔｅｒｔ−ブチルメチルエーテル（４１０ｍｌ）を混合し、次いで、１０℃以下で２−エチルヘキシルマグネシウムブロマイド（１ｍｏｌ／Ｌジエチルエーテル溶液）（１７３ｍｌ）を滴下し、室温にて４時間攪拌した。その後、、水（５００ｍｌ）と２Ｎ塩酸（１００ｍｌ）の混合液に対して、上記で得られた反応液を全量注加し、酢酸エチルにより抽出し、塩化ナトリウム水溶液で洗浄し、有機層を硫酸マグネシウで乾燥後、減圧下において溶媒を留去した。得られた残留物をシリカゲルカラムクロマトグラフィー（展開溶媒：ヘキサン）にて精製し、化合物５を淡黄色油状物として２１．３ｇ得た。

After making the inside of the reaction vessel a nitrogen gas atmosphere, 1,5-naphthylbis (trifluoromethanesulfonate) (compound 4, 25.0 g), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II ) Dichloromethylene adduct (0.24 g) and tert-butyl methyl ether (410 ml) were mixed, and then 2-ethylhexylmagnesium bromide (1 mol / L diethyl ether solution) (173 ml) was added dropwise at 10 ° C. or lower at room temperature. For 4 hours. Thereafter, the entire amount of the reaction solution obtained above was poured into a mixture of water (500 ml) and 2N hydrochloric acid (100 ml), extracted with ethyl acetate, washed with an aqueous sodium chloride solution, and the organic layer was sulfated. After drying with magnesium, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: hexane) to obtain 21.3 g of Compound 5 as a pale yellow oil.

MS (ESI, positive): [M + H] ⁺ 353
¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 0.75-1.00 (12H, m), 1.10-1.50 (16H, m), 1.69-1.85 ( 2H, m), 2.90-3.05 (4H, m), 7.24-7.38 (2H, m), 7.35-7.44 (2H, m), 7.90-7. 95 (2H, m).

<Synthesis Example 3: Synthesis of Compound 6>

反応容器内を窒素ガス雰囲気とした後、化合物５（２１．３ｇ）、ビス（ピナコラート）ジボロン（４，４，４'，４'，５，５，５'，５'−オクタメチル−２，２'−ビ−１，３，２−ジオキサボロラン）（４６．０ｇ）、ビス(１，５−シクロオクタジエン)ジ−μ−メトキシジイリジウム（Ｉ）（０．２４ｇ）（アルドリッチ社製。合成方法は、例えば、Ｊｏｕｒｎａｌ ｏｆ Ｍｏｌｅｃｕｌａｒ Ｃａｔａｌｙｓｉｓ Ａ：Ｃｈｅｍｉｃａｌ １８７ (２００２) １６９に記載されている。）、４，４'−ジｔｅｒｔ−ブチル−２，２'−ジピリジル（０．１９ｇ）およびジオキサン（１４０ｍｌ）を混合し、１００℃で３時間攪拌した。その後、室温まで冷却し、ジオキサンを減圧下において留去し、得られた残留物にメタノール（２００ｍｌ）を加えることで析出した固体をろ取し、乾燥させた。得られた固体をトルエン（２５０ｍｌ）に溶解させ、活性白土（２０ｇ）を加え、６０℃で３０分撹拌後、シリカゲルをプレコートした濾過機にて熱時ろ過し、得られたろ液を減圧下で濃縮した。得られた残渣にメタノール（２５０ｍｌ）を加えることで析出した固体をろ取し、乾燥して、化合物６を白色粉末固体として２８．０ｇ得た。

The reaction vessel was filled with a nitrogen gas atmosphere, and then compound 5 (21.3 g), bis (pinacolato) diboron (4,4,4 ′, 4 ′, 5,5,5 ′, 5′-octamethyl-2,2 '-Bi-1,3,2-dioxaborolane) (46.0 g), bis (1,5-cyclooctadiene) di-μ-methoxydiiridium (I) (0.24 g) (manufactured by Aldrich, synthesis method). Are described, for example, in Journal of Molecular Catalysis A: Chemical 187 (2002) 169), 4,4′-ditert-butyl-2,2′-dipyridyl (0.19 g) and dioxane (140 ml). Were mixed and stirred at 100 ° C. for 3 hours. Then, it cooled to room temperature, the dioxane was distilled off under reduced pressure, the solid which precipitated by adding methanol (200 ml) to the obtained residue was filtered and dried. The obtained solid was dissolved in toluene (250 ml), activated clay (20 g) was added, and the mixture was stirred at 60 ° C. for 30 minutes, followed by hot filtration with a filter pre-coated with silica gel. The obtained filtrate was reduced under reduced pressure. Concentrated. Methanol (250 ml) was added to the resulting residue, and the precipitated solid was collected by filtration and dried to obtain 28.0 g of Compound 6 as a white powder solid.

LC-MS (ESI, positive): [M + H] ⁺ 605
¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 0.85-0.95 (12H, m), 1.24-1.50 (40H, m), 1.6-1.85 ( 2H, m), 2.90-3.18 (4H, m), 7.60 (2H, s), 8.47 (2H, s).

<Synthesis Example 4> (Synthesis of Compound 7)

反応容器内を窒素ガス雰囲気とした後、化合物６（２８．０ｇ）、ジオキサン（４２０ｍＬ）、Ｎ，Ｎ−ジメチルホルムアミド（４２０ｍＬ）および水（２１０ｍＬ）を混合し、臭化銅（II）（６２．７ｇ）を加え、９５℃で２時間攪拌した。その後、同温度で臭化銅（II）（３１．４ｇ）を加え、１．５時間撹拌した後、臭化銅（II）（３１．４ｇ）を追加し、１．５時間撹拌した。その後、得られた反応液を室温まで冷却し、そこにヘキサンを加え１時間攪拌した。その後、得られた有機層を分液し、硫酸マグネシウムで乾燥させた後、減圧下にてジオキサンを留去した。得られた残留物をシリカゲルカラムクロマトグラフィー（展開溶媒：ヘキサン）により精製し、濃縮しることで固体（２１．０ｇ）を得た。得られた固体をトルエンに溶解させ、活性炭を加え、６０℃で３０分撹拌した。その後、得られた混合物を、セライトをプレコートした濾過機にて熱時ろ過し、得られたろ液を減圧下にて濃縮した。得られた残渣をトルエンとメタノールの混合液より再結晶し、化合物７を白色固体として１３．２ｇ得た。

The reaction vessel was filled with a nitrogen gas atmosphere, and then compound 6 (28.0 g), dioxane (420 mL), N, N-dimethylformamide (420 mL) and water (210 mL) were mixed to obtain copper (II) bromide (62 0.7 g) was added and stirred at 95 ° C. for 2 hours. Thereafter, copper (II) bromide (31.4 g) was added at the same temperature and stirred for 1.5 hours, and then copper (II) bromide (31.4 g) was added and stirred for 1.5 hours. Then, the obtained reaction liquid was cooled to room temperature, hexane was added there, and it stirred for 1 hour. Thereafter, the obtained organic layer was separated and dried over magnesium sulfate, and then dioxane was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (developing solvent: hexane) and concentrated to obtain a solid (21.0 g). The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred at 60 ° C. for 30 minutes. Thereafter, the obtained mixture was filtered while hot with a filter pre-coated with Celite, and the obtained filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from a mixed solution of toluene and methanol to obtain 13.2 g of Compound 7 as a white solid.

MS (ESI, positive) [M ⁺ ] 511
¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 0.80-0.98 (12H, m), 1.20-1.44 (16H, m), 1.64-1.80 ( 2H, m), 2.77-2.95 (4H, m), 7.37 (2H, s), 8.00 (2H, s).

<Synthesis Example 5> (Synthesis of Compound 8)

反応容器内をアルゴンガス雰囲気とした後、１−ブロモ−３，５−ジ−ｎ−ヘキシルベンゼン（５８．４ｇ）およびテトラヒドロフランを加え、均一溶液を調製し、−７５℃まで冷却した。得られた溶液に、２．５Ｍのｎ−ブチルリチウム／ヘキサン溶液（１−ブロモ−３，５−ジ−ｎ−ヘキシルベンゼンに対して１モル当量）（７１．２ｍｌ）を−７５℃で１．５時間かけて滴下し、得られた溶液をさらに−７０℃で１．５時間撹拌した。その後、２，７−ジブロモフルオレノン（５５．２ｇ）およびテトラヒドロフランからなる溶液を−７５℃で１時間かけて滴下し、得られた反応溶液を室温まで昇温させた後、４時間撹拌した。その後、得られた溶液を０℃まで冷却し、アセトンおよび２ｍｏｌ％塩酸水をゆっくり加え撹拌した後、室温まで昇温し、室温にて静置した。その後、得られた反応混合物をろ過し、得られたろ液を濃縮し、ヘキサンおよび水を加え撹拌し、分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮し、化合物８を３０．２ｇ得た。

After making the inside of the reaction vessel an argon gas atmosphere, 1-bromo-3,5-di-n-hexylbenzene (58.4 g) and tetrahydrofuran were added to prepare a homogeneous solution and cooled to -75 ° C. To the resulting solution was added 2.5M n-butyllithium / hexane solution (1 molar equivalent to 1-bromo-3,5-di-n-hexylbenzene) (71.2 ml) at -75 ° C. The solution was added dropwise over 5 hours, and the resulting solution was further stirred at -70 ° C for 1.5 hours. Thereafter, a solution consisting of 2,7-dibromofluorenone (55.2 g) and tetrahydrofuran was added dropwise at −75 ° C. over 1 hour, and the resulting reaction solution was warmed to room temperature and stirred for 4 hours. Thereafter, the resulting solution was cooled to 0 ° C., slowly added with acetone and 2 mol% aqueous hydrochloric acid and stirred, then warmed to room temperature and allowed to stand at room temperature. Then, the obtained reaction mixture was filtered, the obtained filtrate was concentrated, hexane and water were added and stirred, and liquid separation was performed. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated to obtain 30.2 g of Compound 8.

<Synthesis Example 6: Synthesis of Compound 9>

反応容器内をアルゴンガス気流下とし、化合物８（２７．７ｇ）およびトリフルオロ酢酸（３６ｍｌ）を加えた。得られた溶液に対して、トリメチルシラン（８．４ｍｌ）およびヘキサン（２５ｍｌ）の混合溶液を３０分間かけて滴下し、室温にて一晩撹拌した。その後、、得られた反応溶液を１０℃に冷却し、ヘキサンと蒸留水を加え、１時間撹拌した後、分液を行った。その後、水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、濃縮することで溶媒を除去した。その後、得られた残渣メタノールで洗浄することにより、目的とする化合物９を１２．１ｇ得た。

The inside of the reaction vessel was under an argon gas stream, and compound 8 (27.7 g) and trifluoroacetic acid (36 ml) were added. To the resulting solution, a mixed solution of trimethylsilane (8.4 ml) and hexane (25 ml) was added dropwise over 30 minutes and stirred overnight at room temperature. Thereafter, the obtained reaction solution was cooled to 10 ° C., hexane and distilled water were added, and the mixture was stirred for 1 hour, followed by liquid separation. Then, water was added and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent, and concentrated to remove the solvent. Then, 12.1g of target compounds 9 were obtained by wash | cleaning with the obtained residual methanol.

<Synthesis Example 7: Synthesis of Compound 10>

反応容器内をアルゴンガス気流下とし、化合物９（１２．０ｇ）、ジメチルスルホキシド（６０ｍｌ）、水（２ｍｌ）および水酸化カリウム（４．８５ｇ）を加えた。得られた溶液にヨウ化メチル（４．１ｍｌ）を滴下し、室温にて一晩撹拌した。その後、得られた反応溶液に対して、室温においてヘキサンおよび蒸留水を加え、１時間撹拌した後、分液を行った。その後、得られた油層に水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、得られた残渣をメタノールおよび酢酸ブチルを用いて再結晶することにより、目的とする化合物１０を４．３ｇ得た。

The reaction vessel was placed under an argon gas stream, and compound 9 (12.0 g), dimethyl sulfoxide (60 ml), water (2 ml) and potassium hydroxide (4.85 g) were added. Methyl iodide (4.1 ml) was added dropwise to the resulting solution and stirred overnight at room temperature. Thereafter, hexane and distilled water were added to the obtained reaction solution at room temperature, and the mixture was stirred for 1 hour, followed by liquid separation. Then, water was added to the obtained oil layer and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Then, 4.3 g of the target compound 10 was obtained by recrystallizing the obtained residue using methanol and butyl acetate.

<Synthesis Example 8: Synthesis of Compound 11>

反応容器内をアルゴンガス雰囲気とし、化合物１０（４．２ｇ）、ビス（ピナコラート）ジボロン（４，４，４'，４'，５，５，５'，５'−オクタメチル−２，２'−ビ−１，３，２−ジオキサボロラン）（４．０ｇ）、１，４−ジオキサン（４５ｍｌ）、酢酸カリウム（４．２ｇ）、１，１'−ビス（ジフェニルホスフィノ）フェロセン（ｄｐｐｆ、５９ｍｇ）および１，１'−ビス（ジフェニルホスフィノ）フェロセンジクロロパラジウム（ＩＩ）塩化メチレン錯体（ＰｄＣｌ_２（ｄｐｐｆ）・ＣＨ_２Ｃｌ_２、８８ｍｇ）を加え、１００℃で２０時間撹拌した。その後、得られた反応液を室温まで冷却した後、セライトおよびシリカゲルを敷き詰めたろ過器でろ過し、得られたろ液を濃縮してジオキサンを除去した。その後、ヘキサンを加えて調製した溶液に、活性炭を加え、ヘキサンが還流する温度にて１時間撹拌した。得られた反応液を室温まで冷却後、セライトを敷き詰めたろ過器でろ過し、得られたろ液を濃縮してヘキサンを除去した。その後、得られた残渣をトルエンおよびメタノールを用いて再結晶することにより、目的とする化合物１１を３．９ｇ得た。

The reaction vessel was filled with an argon gas atmosphere, and compound 10 (4.2 g), bis (pinacolato) diboron (4,4,4 ′, 4 ′, 5,5,5 ′, 5′-octamethyl-2,2′- Bi-1,3,2-dioxaborolane) (4.0 g), 1,4-dioxane (45 ml), potassium acetate (4.2 g), 1,1′-bis (diphenylphosphino) ferrocene (dppf, 59 mg) Then, 1,1′-bis (diphenylphosphino) ferrocenedichloropalladium (II) methylene chloride complex (PdCl ₂ (dppf) · CH ₂ Cl ₂ , 88 mg) was added, and the mixture was stirred at 100 ° C. for 20 hours. Then, after cooling the obtained reaction liquid to room temperature, it filtered with the filter which spread celite and the silica gel, and the obtained filtrate was concentrated and the dioxane was removed. Thereafter, activated carbon was added to the solution prepared by adding hexane, and the mixture was stirred at a temperature at which hexane was refluxed for 1 hour. The obtained reaction solution was cooled to room temperature, filtered through a filter packed with celite, and the obtained filtrate was concentrated to remove hexane. Then, 3.9g of target compounds 11 were obtained by recrystallizing the obtained residue using toluene and methanol.

<Synthesis Example 9: Synthesis of Compound 12>

反応容器内をアルゴンガス雰囲気とし、３−ｎ−ヘキシルブロモベンゼン（１１１．１ｇ）およびテトラヒドロフランを加え、均一溶液を調製し、−７５℃まで冷却した。得られた溶液に２．５Ｍのｎ−ブチルリチウム／ヘキサン溶液（３−ｎ−ヘキシルブロモベンゼンに対して１モル当量）（１７６ｍｌ）を−７５℃で１．５時間かけて滴下し、得られた溶液をさらに−７０℃で１．５時間撹拌した。その後、２，７−ジブロモフルオレノン（１４２ｇ）およびテトラヒドロフランからなる溶液を−７５℃で１時間かけて滴下し、得られた反応溶液を室温まで昇温させた後、４時間撹拌した。その後、得られた溶液を０℃まで冷却し、アセトンおよび２ｍｏｌ％塩酸水をゆっくり加え撹拌した後、室温まで昇温し、室温にて静置した。その後、得られた反応液をろ過し、ろ液を濃縮し、ヘキサンおよび水を加え撹拌し、分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、化合物１２を１６２ｇ得た。

The reaction vessel was filled with an argon gas atmosphere, and 3-n-hexyl bromobenzene (111.1 g) and tetrahydrofuran were added to prepare a homogeneous solution and cooled to -75 ° C. A 2.5M n-butyllithium / hexane solution (1 molar equivalent to 3-n-hexylbromobenzene) (176 ml) was added dropwise to the obtained solution at -75 ° C over 1.5 hours. The solution was further stirred at −70 ° C. for 1.5 hours. Thereafter, a solution consisting of 2,7-dibromofluorenone (142 g) and tetrahydrofuran was added dropwise at −75 ° C. over 1 hour, and the resulting reaction solution was warmed to room temperature and stirred for 4 hours. Thereafter, the resulting solution was cooled to 0 ° C., slowly added with acetone and 2 mol% aqueous hydrochloric acid and stirred, then warmed to room temperature and allowed to stand at room temperature. Then, the obtained reaction liquid was filtered, the filtrate was concentrated, hexane and water were added and stirred, and liquid separation was performed. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent to obtain 162 g of Compound 12.

<Synthesis Example 10: Synthesis of Compound 13>

反応容器内をアルゴンガス気流下とし、化合物１２（１６２ｇ）およびトリフルオロ酢酸（２４５ｍｌ）を加えた。得られた溶液にトリメチルシラン（１１５ｍｌ）を３０分間かけて滴下し、室温にて一晩撹拌した。その後、得られた反応溶液を１０℃に冷却し、ヘキサンおよび蒸留水を加え、１時間撹拌した後、分液を行った。その後、得られた油層に水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、濃縮して溶媒を除去した。得られた残渣をメタノールで洗浄することにより、目的とする化合物１３を１３８ｇ得た。

The inside of the reaction vessel was under an argon gas stream, and Compound 12 (162 g) and trifluoroacetic acid (245 ml) were added. Trimethylsilane (115 ml) was added dropwise to the resulting solution over 30 minutes and stirred overnight at room temperature. Thereafter, the obtained reaction solution was cooled to 10 ° C., hexane and distilled water were added, and the mixture was stirred for 1 hour, followed by liquid separation. Then, water was added to the obtained oil layer and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent, and concentrated to remove the solvent. The obtained residue was washed with methanol to obtain 138 g of the intended compound 13.

<Synthesis Example 11: Synthesis of Compound 14>

反応容器内をアルゴンガス気流下とし、化合物１３（１３８ｇ）、１−ブロモオクタン（７５．４ｍｌ）、メチルトリオクチルアンモニウムクロライド（商品名：Ａｌｉｑｕａｔ（登録商標）３３６、アルドリッチ社製）（１．２ｇ）および４０％水酸化カリウム（６０ｍｌ）を加え、８５℃にて一晩撹拌した。その後、得られた反応溶液を室温まで冷却し、ジクロロメタンおよび蒸留水を加え、１時間撹拌した後、分液を行った。その後、得られた油層に水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、濃縮して溶媒を除去した。その後、得られた残渣に対して、メタノールおよびジクロロメタンを用いた再沈殿を行うことにより、目的とする化合物１４を１４５ｇ得た。

The inside of the reaction vessel was placed under an argon gas stream, and compound 13 (138 g), 1-bromooctane (75.4 ml), methyl trioctyl ammonium chloride (trade name: Aliquat (registered trademark) 336, manufactured by Aldrich) (1.2 g) ) And 40% potassium hydroxide (60 ml) were added and stirred at 85 ° C. overnight. Then, the obtained reaction solution was cooled to room temperature, dichloromethane and distilled water were added, and after stirring for 1 hour, liquid separation was performed. Then, water was added to the obtained oil layer and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent, and concentrated to remove the solvent. Then, 145g of the target compound 14 was obtained by performing reprecipitation using methanol and dichloromethane with respect to the obtained residue.

<Synthesis Example 12: Synthesis of Compound 16>

撹拌器を備えた１Ｌの四つ口フラスコに、ｎ−ヘプチルトリフェニルホスホニウムブロミド（１１５．０ｇ）を入れ、該フラスコ内の気体をアルゴンガスで置換した。このフラスコ内に、トルエン（３７５ｇ）を入れ、５℃以下に冷却した。その後、カリウムｔｅｒｔ−ブトキシド（２９．２ｇ）を入れ、室温まで昇温した後、室温で３時間保温撹拌した。得られた反応液中に生じた赤色スラリーに、化合物１５（１５．０ｇ）を加え、室温にて１２時間撹拌した。得られた反応液に酢酸（１０．０ｇ）を入れて１５分撹拌した後、ろ過し、得られた残渣をトルエンで複数回洗浄した。複数回分のろ液を合わせて濃縮した後、ヘキサンを入れたところスラリーが生じたので、このスラリーを５０℃で１時間撹拌した。得られた混合物を室温まで冷却し、ろ過した。得られた残渣をヘキサンで複数回洗浄し、複数回分のろ液を合わせて濃縮することで粗生成物が得られた。この粗生成物を、シリカゲルカラム（展開溶媒：ヘキサン）を用いて精製することで、無色透明液体として化合物１６を２１．７ｇ得た。

N-heptyltriphenylphosphonium bromide (115.0 g) was placed in a 1 L four-necked flask equipped with a stirrer, and the gas in the flask was replaced with argon gas. Toluene (375 g) was placed in the flask and cooled to 5 ° C. or lower. Thereafter, potassium tert-butoxide (29.2 g) was added, the temperature was raised to room temperature, and the mixture was stirred while keeping at room temperature for 3 hours. Compound 15 (15.0 g) was added to the red slurry produced in the resulting reaction solution, and the mixture was stirred at room temperature for 12 hours. Acetic acid (10.0 g) was added to the resulting reaction solution and stirred for 15 minutes, followed by filtration. The resulting residue was washed with toluene several times. A plurality of filtrates were combined and concentrated, and then hexane was added to form a slurry. The slurry was stirred at 50 ° C. for 1 hour. The resulting mixture was cooled to room temperature and filtered. The obtained residue was washed several times with hexane, and the crude product was obtained by combining and concentrating the filtrate for multiple times. The crude product was purified using a silica gel column (developing solvent: hexane) to obtain 21.7 g of Compound 16 as a colorless transparent liquid.

LC-MS (ESI, positive): [M + K] ⁺ 491
¹ H-NMR (CDCl ₃ , 300 MHz): δ (ppm) = 0.87 (6H, t), 1.20 to 1.36 (16H, m), 1.82 to 1.97 (4H, m) 2.57 to 2.81 (8H, m), 5.20 (2H, br), 7.23 to 7.32 (4H, m), 7.41 to 7.48 (2H, m), 7 .87-7.90 (2H, m).

<Synthesis Example 13: Synthesis of Compound 17>
In the formula, the wavy line indicates that the compound having the wavy line is a geometric isomer mixture. In the formula, * indicates that the carbon atom to which it is attached is an asymmetric carbon atom.

撹拌器を備えた１Ｌの四つ口フラスコに、化合物１６（２１．７ｇ）、酢酸エチル（１５２．４ｇ）およびエタノール（１５１．６ｇ）を入れ、フラスコ内の気体を窒素ガスで置換した。その後、５重量％Ｐｄ／Ｃ（約５０重量％含水品）（４．３ｇ）を入れ、フラスコ内の気体を水素ガスで置換し、４０℃で２７時間撹拌した。その後、室温まで冷却し、セライトをプレコートした濾過器によりろ過し、得られた残渣を酢酸エチルで複数回洗浄し、複数回分のろ液を合わせて濃縮することにより、粗生成物を得た。この粗生成物を、シリカゲルカラム（展開溶媒：ヘキサン）を用いて精製することで、無色透明液体として化合物１７を２１．７ｇ得た。

Compound 16 (21.7 g), ethyl acetate (152.4 g) and ethanol (151.6 g) were placed in a 1 L four-necked flask equipped with a stirrer, and the gas in the flask was replaced with nitrogen gas. Thereafter, 5 wt% Pd / C (about 50 wt% water-containing product) (4.3 g) was added, and the gas in the flask was replaced with hydrogen gas, followed by stirring at 40 ° C for 27 hours. Then, it cooled to room temperature, filtered with the filter which pre-coated celite, the obtained residue was wash | cleaned several times with ethyl acetate, the crude product was obtained by combining several filtrates and concentrating. The crude product was purified using a silica gel column (developing solvent: hexane) to obtain 21.7 g of Compound 17 as a colorless transparent liquid.

LC-MS (APPI, positive): [M] ⁺ 456
¹ H-NMR (CDCl ₃ , 300 MHz): δ (ppm) = 0.66 to 0.98 (6H, m), 1.00 to 2.22 (34H, m), 7.13 to 7.50 ( 6H, m), 7.80-7.98 (2H, m).

<Synthesis Example 14: Synthesis of Compound 18>
In the formula, * indicates that the carbon atom to which it is attached is an asymmetric carbon atom.

撹拌器を備えた５００ｍＬの四つ口フラスコに、化合物１７（２１．７ｇ）、クロロホルム（２６１．１ｇ）およびトリフルオロ酢酸（４４ｇ）を入れ、フラスコ内の気体をアルゴンガスで置換した。その後、四つ口フラスコ全体を遮光し、臭素（１９．０ｇ）およびクロロホルム（６５．３ｇ）の混合物を、室温で１５分間かけて滴下し、３５℃まで昇温した。その後、３５℃で７時間撹拌し、１５℃以下に冷却した。得られた反応液に１０重量％亜硫酸ナトリウム水溶液（１０９ｇ）入れ、室温まで昇温した。得られた反応液から水層を分離し、得られた有機層を水、５重量％炭酸水素ナトリウム水溶液、水の順に洗浄した。得られた有機層を硫酸マグネシウムで乾燥させ、ろ過し、得られたろ液を濃縮することにより、粗生成物を得た。この粗生成物をエタノールおよびヘキサンの混合溶媒を用いて、２回再結晶を行った。得られた固体をヘキサンに溶解させ、シリカゲルカラム（展開溶媒：ヘキサン）を用いて精製し、得られたヘキサン溶液に活性炭（２．１ｇ）を加え、４５℃で１時間撹拌した。その後、室温まで冷却し、セライトをプレコートした濾過器によりろ過し、得られた残渣をヘキサンで複数回洗浄し、複数回分のろ液を合わせて一部濃縮しヘキサン溶液を得た。このヘキサン溶液にエタノールを加え、再結晶することにより、化合物１８を白色固体として１８．８ｇ得た。

Compound 17 (21.7 g), chloroform (261.1 g) and trifluoroacetic acid (44 g) were placed in a 500 mL four-necked flask equipped with a stirrer, and the gas in the flask was replaced with argon gas. Thereafter, the entire four-necked flask was shielded from light, and a mixture of bromine (19.0 g) and chloroform (65.3 g) was added dropwise at room temperature over 15 minutes, and the temperature was raised to 35 ° C. Then, it stirred at 35 degreeC for 7 hours, and cooled to 15 degrees C or less. A 10% by weight aqueous sodium sulfite solution (109 g) was added to the resulting reaction solution, and the temperature was raised to room temperature. The aqueous layer was separated from the obtained reaction solution, and the obtained organic layer was washed with water, a 5 wt% aqueous sodium hydrogen carbonate solution and water in this order. The obtained organic layer was dried with magnesium sulfate, filtered, and the obtained filtrate was concentrated to obtain a crude product. This crude product was recrystallized twice using a mixed solvent of ethanol and hexane. The obtained solid was dissolved in hexane, purified using a silica gel column (developing solvent: hexane), activated carbon (2.1 g) was added to the obtained hexane solution, and the mixture was stirred at 45 ° C. for 1 hour. Then, it cooled to room temperature and filtered with the filter which pre-coated celite, the obtained residue was wash | cleaned several times with hexane, the filtrate for several times was combined, and it concentrated partially, and obtained the hexane solution. Ethanol was added to this hexane solution and recrystallized to obtain 18.8 g of Compound 18 as a white solid.

LC-MS (ESI, negative): [M + Cl] ⁻ 648
¹ H-NMR (CDCl ₃ , 300 MHz): δ (ppm) = 0.66 to 0.98 (6H, m), 1.00 to 2.20 (34H, m), 7.22 to 7.78 ( 6H, m).

<Synthesis Example 15: Synthesis of Polymer Compound 1>
After making the inside of the reaction vessel an inert gas atmosphere, the following formula synthesized according to the method described in JP 2011-174062 A:

で示される化合物１９（２．６８８２ｇ、２．９６ｍｍｏｌ）、下記式：

Compound 19 (2.6882 g, 2.96 mmol) represented by the following formula:

で示される化合物２０（０．４２４５ｇ、０．７７４ｍｍｏｌ）、下記式：

Compound 20 (0.4245 g, 0.774 mmol) represented by the following formula:

で示される化合物２１（１．６３９６ｇ、１．８０ｍｍｏｌ）、特開２００８−１０６２４１号公報に記載の方法に従って合成した下記式：

Compound 21 (1.6396 g, 1.80 mmol) represented by the following formula synthesized according to the method described in JP-A-2008-106241:

で示される化合物２２（０．２３７７ｇ、０．４５ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（２．１ｍｇ）およびトルエン（６２ｍｌ）を混合し、１０５℃に加熱した。

Embedded image Compound 22 (0.2377 g, 0.45 mmol), dichlorobis (triphenylphosphine) palladium (2.1 mg) and toluene (62 ml) were mixed and heated to 105 ° C.

To the resulting reaction solution, a 20 wt% tetraethylammonium hydroxide aqueous solution (10 ml) was added dropwise and refluxed for 4.5 hours. After the reaction, phenylboronic acid (36.8 mg) and dichlorobis (triphenylphosphine) palladium (2.1 mg) were added thereto, and the mixture was further refluxed for 16.5. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The obtained solution was cooled to room temperature, washed twice with water, twice with a 3% by weight acetic acid aqueous solution and twice with water, and the resulting solution was dropped into methanol and collected by filtration to obtain a precipitate. It was. This precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol and stirred, and then the precipitate was collected by filtration and dried to obtain 3.12 g of polymer compound 1. The number average molecular weight of polystyrene conversion of the high molecular compound 1 was 7.8 * 10 < ⁴ >, and the weight average molecular weight of polystyrene conversion was 2.6 * 10 < ⁵ >.

  The polymer compound 1 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、５０：１２．５：３０：７．５のモル比で構成されてなる共重合体である。

Is a copolymer composed of a molar ratio of 50: 12.5: 30: 7.5.

<Example 2: Synthesis of polymer compound 2>
After making the inside of the reaction vessel an inert gas atmosphere, compound 3 (0.2045 g, 0.2 mmol), the following formula:

で示される化合物６（１．１９６３ｇ、１．９７ｍｍｏｌ）、下記式：

Compound 6 (1.1963 g, 1.97 mmol) represented by the following formula:

で示される化合物１４（１．０７７２g、１．８０ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（１．４ｍｇ）およびトルエン（４７ｍｌ）を混合し、１０５℃に加熱した。得られた反応溶液に２０重量％水酸化テトラエチルアンモニウム水溶液（７．５ｍｌ）を滴下し、３時間還流させた。反応後、そこに、フェニルボロン酸（２５ｍｇ）、２０重量％水酸化テトラエチルアンモニウム水溶液（７．５ｍｌ）およびジクロロビス（トリフェニルホスフィン）パラジウム（１．５ｍｇ）を加え、更に１７時間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。得られた溶液を室温まで冷却後、水（２６ｍｌ）で２回、３重量％酢酸水溶液（２６ｍｌ）で２回、水（２６ｍｌ）で２回洗浄し、得られた溶液をメタノール（３１０ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（６３ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムを順番に通すことにより精製した。得られた溶液をメタノール（３１０ｍｌ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物２を１．２０ｇ得た。高分子化合物２のポリスチレン換算の数平均分子量は８．８×１０^４であり、ポリスチレン換算の重量平均分子量は２．５×１０⁵であった。

14 (1.0772 g, 1.80 mmol), dichlorobis (triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. After the reaction, phenylboronic acid (25 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) and dichlorobis (triphenylphosphine) palladium (1.5 mg) were added thereto, and the mixture was further refluxed for 17 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting solution was cooled to room temperature, washed twice with water (26 ml), twice with a 3% by weight aqueous acetic acid solution (26 ml) and twice with water (26 ml), and the resulting solution in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the obtained precipitate was collected by filtration and dried to obtain 1.20 g of polymer compound 2. The number average molecular weight in terms of polystyrene of the polymer compound 2 was 8.8 × 10 ⁴ , and the weight average molecular weight in terms of polystyrene was 2.5 × 10 ⁵ .

  The polymer compound 2 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、５０：４５：５のモル比で構成されてなる共重合体である。

Is a copolymer having a molar ratio of 50: 45: 5.

<Example 3: Synthesis of polymer compound 3>
After making the inside of the reaction vessel an inert gas atmosphere, compound 3 (0.2045 g, 0.2 mmol), compound 6 (1.2474 g, 1.97 mmol), compound 7 (0.9703 g, 1.80 mmol), dichlorobis ( Triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours.
After the reaction, phenylboronic acid (25 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) and dichlorobis (triphenylphosphine) palladium (1.5 mg) were added thereto, and the mixture was further refluxed for 17 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting solution was cooled to room temperature, washed twice with water (26 ml), twice with a 3% by weight aqueous acetic acid solution (26 ml) and twice with water (26 ml), and the resulting solution in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.31 g of polymer compound 3. The number average molecular weight in terms of polystyrene of the polymer compound 3 was 8.1 × 10 ⁴ , and the weight average molecular weight in terms of polystyrene was 2.6 × 10 ⁵ .

  The polymer compound 3 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、９５：５のモル比で構成されてなる共重合体である。

Is a copolymer having a molar ratio of 95: 5.

<Example 4: Synthesis of polymer compound 4>
After the inside of the reaction vessel was filled with an inert gas atmosphere, Compound 3 (0.2045 g, 0.2 mmol), Compound 11 (1.3382 g, 1.97 mmol), Compound 7 (0.4082 g, 0.8 mmol), Compound 18 (0.6154 g, 1.0 mmol), dichlorobis (triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. After the reaction, phenylboronic acid (25 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) and dichlorobis (triphenylphosphine) palladium (1.5 mg) were added thereto, and the mixture was further refluxed for 17 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting solution was cooled to room temperature, washed twice with water (26 ml), twice with a 3% by weight aqueous acetic acid solution (26 ml) and twice with water (26 ml), and the resulting solution in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.51 g of polymer compound 4. The polymer compound 4 had a polystyrene-equivalent number average molecular weight of 2.0 × 10 ⁵ and a polystyrene-equivalent weight average molecular weight of 3.5 × 10 ⁵ .

  The polymer compound 4 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、５０：２０：２５：５のモル比で構成されてなる共重合体である。

Is a copolymer composed of a molar ratio of 50: 20: 25: 5.

<Comparative Example 1: Synthesis of polymer compound 5>
After making the inside of the reaction vessel an inert gas atmosphere, Compound 6 (1.2474 g, 1.97 mmol), Compound 14 (1.0769 g, 1.80 mmol), the following formula:

で示される化合物２３（０．１６３１ｇ、０．２０ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（１．４ｍｇ）およびトルエン（４７ｍｌ）を混合し、１０５℃に加熱した。得られた反応溶液に２０重量％水酸化テトラエチルアンモニウム水溶液（７．５ｍｌ）を滴下し、３時間還流させた。反応後、そこに、フェニルボロン酸（２５ｍｇ）、２０重量％水酸化テトラエチルアンモニウム水溶液（７．５ｍｌ）およびジクロロビス（トリフェニルホスフィン）パラジウム（１．５ｍｇ）を加え、更に１７時間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。得られた溶液を室温まで冷却後、水（２６ｍｌ）で２回、３重量％酢酸水溶液（２６ｍｌ）で２回、水（２６ｍｌ）で２回洗浄し、得られた溶液をメタノール（３１０ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（６３ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムを順番に通すことにより精製した。得られた溶液をメタノール（３１０ｍｌ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物５を１．２３ｇ得た。高分子化合物５のポリスチレン換算の数平均分子量は６．０×１０^４であり、ポリスチレン換算の重量平均分子量は２．１×１０⁵であった。

Embedded image Compound 23 (0.1631 g, 0.20 mmol), dichlorobis (triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. After the reaction, phenylboronic acid (25 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) and dichlorobis (triphenylphosphine) palladium (1.5 mg) were added thereto, and the mixture was further refluxed for 17 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting solution was cooled to room temperature, washed twice with water (26 ml), twice with a 3% by weight aqueous acetic acid solution (26 ml) and twice with water (26 ml), and the resulting solution in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.23 g of polymer compound 5. The polymer compound 5 had a polystyrene-equivalent number average molecular weight of 6.0 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.1 × 10 ⁵ .

  The polymer compound 5 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、５０：４５：５のモル比で構成されてなる共重合体である。

Is a copolymer having a molar ratio of 50: 45: 5.

<Comparative Example 2: Synthesis of polymer compound 6>
After the inside of the reaction vessel was filled with an inert gas atmosphere, Compound 23 (0.1640 g, 0.20 mmol), Compound 6 (1.2500 g, 1.97 mmol), Compound 7 (0.9703 g, 1.80 mmol), dichlorobis ( Triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. After the reaction, phenylboronic acid (25 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) and dichlorobis (triphenylphosphine) palladium (1.5 mg) were added thereto, and the mixture was further refluxed for 17 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting solution was cooled to room temperature, washed twice with water (26 ml), twice with a 3% by weight aqueous acetic acid solution (26 ml) and twice with water (26 ml), and the resulting solution in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.16 g of polymer compound 6. The polymer compound 6 had a polystyrene-equivalent number average molecular weight of 1.3 × 10 ⁵ and a polystyrene-equivalent weight average molecular weight of 2.9 × 10 ⁵ .

  The polymer compound 6 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、９５：５のモル比で構成されてなる共重合体である。

Is a copolymer having a molar ratio of 95: 5.

<Example D1: Production and evaluation of light-emitting element D1>
Using a Plexcore OC RG-1200 (manufactured by Sigma-Aldrich), a hole injection layer is formed to a thickness of 35 nm by spin coating on a glass substrate with a 45 nm thick ITO film formed by sputtering. It was dried by heating at 170 ° C. for 15 minutes.
Next, the polymer compound 1 was dissolved in xylene to prepare a 0.7% by mass xylene solution. Using this xylene solution, a hole transport layer was formed to a thickness of 20 nm by spin coating on the hole injection layer, and heated in a nitrogen gas atmosphere on a hot plate at 180 ° C. for 60 minutes.
Next, the polymer compound 2 was dissolved in xylene to prepare a 1.3% by mass xylene solution. Using this xylene solution, a light emitting layer was formed to a thickness of 65 nm by spin coating on the hole transport layer, and heated at 150 ° C. for 10 minutes on a hot plate in a nitrogen gas atmosphere.
Next, 5 nm of sodium fluoride and then 120 nm of aluminum were vapor-deposited as a cathode on the light emitting layer, and the light emitting element D1 was produced. In addition, after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, metal deposition was started.
The obtained light emitting element D1 was driven at a constant current after setting the current value so that the initial luminance was 1000 cd / m ^2, and the change in luminance with time was measured. As a result, the luminance was reduced by half after 403 hours. The results are shown in Table 1.

<Example D2: Production and Evaluation of Light-Emitting Element D2>
A light emitting device D2 was produced in the same manner as in Example D1, except that the polymer compound 3 was used in place of the polymer compound 2 in Example D1.
The obtained light emitting element D2 was driven at a constant current after setting the current value so that the initial luminance was 1000 cd / m ^2, and the change in luminance with time was measured. As a result, the luminance was reduced by half after 245 hours. The results are shown in Table 1.

<Example CD1: Production and Evaluation of Light-Emitting Element CD1>
A light emitting device CD1 was produced in the same manner as in Example D1, except that the polymer compound 5 was used in place of the polymer compound 2 of Example D1.
The obtained light emitting element CD1 was driven at a constant current after setting the current value so that the initial luminance was 1000 cd / m ^2, and the change in luminance with time was measured. As a result, the luminance was reduced by half after 218 hours. The results are shown in Table 1.

<Example CD2: Production and Evaluation of Light-Emitting Element CD2>
A light emitting device CD2 was produced in the same manner as in Example D1, except that the polymer compound 6 was used in place of the polymer compound 2 in Example D1.
The light emitting element CD2 thus obtained was set at a current value so that the initial luminance was 1000 cd / m ^2, and then was driven with a constant current, and the change in luminance with time was measured. As a result, the luminance was reduced by half after 191 hours. The results are shown in Table 1.

  The polymer compound 2 and the polymer compound 3 correspond to the polymer compound according to the present invention. From the comparison between Example D1 and Comparative Example CD1 and the comparison between Example D2 and Comparative Example CD2, Polymer Compound 2 and Polymer Compound 3 showed excellent luminance lifetime.

Claims (16)

At least one structural unit selected from the group consisting of a structural unit represented by the following formula (1-1), a structural unit represented by the following formula (1-2), and a structural unit represented by the following formula (1-3) When,
At least one structural unit selected from the group consisting of a structural unit represented by the following formula (2), a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4);
A polymer compound containing

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted An aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocycle.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]

[Where:
a and b each independently represent an integer of 0 to 3.
R ⁴ and R ⁵ are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted 1 A valent heterocyclic group is shown.
R ⁶ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group.
R ⁷ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group. ]

[Where:
c and d each independently represent an integer of 0 to 3.
R ⁸ and R ⁹ are each independently an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted 1 A valent heterocyclic group is shown.
R ¹⁰ , R ¹¹ , R ¹² and R ¹³ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown. R ¹⁰ and R ¹² may be connected to each other to form a ring structure, R ¹¹ and R ¹³ may be connected to each other to form a ring structure, and R ¹⁰ and R ¹¹ are connected to each other. A ring structure may be formed, and R ¹² and R ¹³ may be linked to each other to form a ring structure. Provided that at least one pair selected from the group consisting of R ¹⁰ and R ¹² , R ¹¹ and R ¹³ , R ¹⁰ and R ¹¹ , and R ¹² and R ¹³ is bonded to each other, together with the carbon atom to which each is bonded. Form a ring structure. ]

[Where:
R ¹⁴ and R ¹⁵ each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or A substituted monovalent heterocyclic group is shown. However, at least one selected from the group consisting of R ¹⁴ and R ¹⁵ represents a group other than a hydrogen atom.
] The structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3) are each represented by the following formula (1-1-A 2. The polymer compound according to claim 1, which is a structural unit represented by the following formula (1-2-A) and a structural unit represented by the following formula (1-3-A).

[Where:
X, Y, R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.
R ²³ , R ²⁴ and R ²⁵ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group or R represents an unsubstituted or substituted monovalent heterocyclic group, and R ²⁴ and R ²⁵ may be connected to each other to form a ring structure together with the carbon atom to which each is bonded. ] The structural unit represented by the formula (1-1-A) and the structural unit represented by the formula (1-2-A) are the structural unit represented by the following formula (1-1-B) and the following formula, respectively. The polymer compound according to claim 2, which is a structural unit represented by (1-2-B).

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 , R ^y2 , R ²³ , R ²⁴ , ²⁵ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.
R ²⁶ , R ²⁷ , R ²⁸ and R ²⁹ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl Represents an oxy group or an unsubstituted or substituted heterocyclic group, R ²⁶ and R ²⁷ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded, and R ²⁸ and R ²⁹ are linked to each other; In addition, a ring structure may be formed together with the carbon atoms to which each is bonded. ] The polymer compound according to any one of claims 1 to 3, wherein the structural unit represented by the formula (3) is a structural unit represented by the following formula (3-A).

[Where:
c, d, R ⁸ and R ⁹ are as defined above.
n ¹ and ^{n 2} each independently represent an integer of 1 to 5.
R ³⁰ , R ³¹ , R ³² and R ³³ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown. When there are a plurality of R ³⁰ , R ³¹ , R ³² and R ³³ , the plurality of R ³⁰ , R ³¹ , R ³² and R ³³ may be the same as or different from each other. R ³⁰ , R ³¹ , R ³² And adjacent groups of R ³³ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded. ] At least one structural unit selected from the group consisting of the structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3). When,
A structural unit represented by the formula (2), a structural unit represented by the formula (4), and
The polymer compound according to claim 1, comprising: Furthermore, the structural unit represented by the following formula (5) (different from the structural unit represented by the formula (2), the structural unit represented by the formula (3), and the structural unit represented by the formula (4)). The high molecular compound as described in any one of Claims 1-5 containing this.

[Where:
Ar ³ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group. ]   The polymer compound according to claim 6, wherein the structural unit represented by the formula (5) is an unsubstituted or substituted fluorenediyl group. Furthermore, a structural unit represented by the following formula (6) (a structural unit represented by the formula (1-1), a structural unit represented by the formula (1-2), and a structure represented by the formula (1-3) The polymer compound according to claim 1, comprising a unit and a structural unit different from the structural unit represented by the formula (5).

[Where:
a ¹ and a ² each independently represent 0 or 1.
Ar ⁴ and Ar ⁶ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ⁵ and Ar ⁷ are each independently an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or the same or different two or more selected from an arylene group and a divalent heterocyclic group The bivalent group which this group connected (The said bivalent group may have a substituent.) Is shown.
R ^C , R ^D and R ^E each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ may each be linked to a group other than the group bonded to the nitrogen atom to which the group is bonded to form a ring structure. ] The polymer compound according to claim 8, wherein the structural unit represented by the formula (6) is a structural unit represented by the following formula (7).

[Where:
R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^{b s} may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]   The structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3) with respect to all the structural units contained in the polymer compound. The high molecular compound as described in any one of Claims 1-9 whose total ratio is 0.1-70 mol%. At least one structural unit selected from the group consisting of a structural unit represented by the following formula (1-1), a structural unit represented by the following formula (1-2), and a structural unit represented by the following formula (1-3) When,
A structural unit represented by the following formula (8);
A polymer compound containing

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted An aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocycle.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]

[Where:
na represents an integer of 0 to 3, nb represents an integer of 0 to 12, nA represents 0 or 1, and n represents 1 or 2.
Ar ⁸ represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent aromatic amine, or an unsubstituted or substituted divalent heterocyclic group.
L ^a and L ^b each independently represent a direct bond, an unsubstituted or substituted alkylene group, or an unsubstituted or substituted phenylene group. When ^a plurality of ^La are present, they may be the same or different. When a plurality of ^Lb are present, they may be the same or different.
L ^A represents an oxygen atom or a sulfur atom. When a plurality of ^LA are present, they may be the same or different.
X ′ represents a monovalent crosslinkable group. When a plurality of X ′ are present, they may be the same or different. ] A compound represented by the following formula (1-1-M), (1-2-M) or (1-3-M).

[Where:
R ¹ , R ² , R ³ , R ^x1 , R ^x2 , R ^y1 and R ^y2 are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted An aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Ring A represents an unsubstituted or substituted aromatic hydrocarbon ring or an unsubstituted or substituted aromatic heterocycle.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.
Z ¹ and Z ² each independently represent a group selected from the following substituent group.
<Substituent group>
Hydrogen atom, chlorine atom, bromine atom, iodine atom,
A group represented by —O—S (═O) ₂ R ⁴¹ (wherein R ⁴¹ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group),
—B (OR ⁴² ) ₂ (R ⁴² represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ⁴² may be the same as or different from each other, and are bonded to each other to bind to each other. And may form a ring structure together with the group
A group represented by -BF ₄ Q ¹ (Q ¹ represents a monovalent cation selected from the group consisting of Li ⁺ , Na ⁺ , K ⁺ , Rb ⁺ and Cs ⁺ );
A group represented by —MgY ¹ (Y ¹ represents a chlorine atom, a bromine atom or an iodine atom); a group represented by —ZnY ² (Y ² represents a chlorine atom, a bromine atom or an iodine atom); and,
—Sn (R ⁴³ ) ₃ (R ⁴³ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ⁴³ may be the same as or different from each other, and are linked to each other, and are bonded to each other. And may form a ring structure together with the above group). ] The polymer compound according to any one of claims 1 to 11,
A composition containing at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.   The organic thin film containing the high molecular compound as described in any one of Claims 1-11.   The insolubilized organic thin film which insolubilized the organic thin film containing the high molecular compound of Claim 11 with respect to the solvent by heating.   A light emitting device comprising the organic thin film according to claim 14 or the insolubilized organic thin film according to claim 15.