JP2014001328A - Polymer compound, and light emitting device using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polymer compound useful for fabrication of a light emitting device having an excellent brightness life.SOLUTION: The polymer compound contains a constitutional unit of the following formula (1), and another specific constitutional unit, where Ar, Arrepresent an arylene group or the like, R, Rrepresent an aryl group or the like, R-Rrepresent a hydrogen atom or the like, and Rrepresents 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 device, for example, a polymer compound (Patent Document 1) containing a structural unit represented by the following derived from arylamine, and a structural unit represented by the following derived from fluorene: A high molecular compound (Patent Document 2) containing benzene has been studied.

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

  However, a light-emitting element manufactured using the above polymer compound does not always have a sufficient luminance life.

  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, and a light emitting device containing the polymer compound. Another object of the present invention is to provide a raw material compound of the polymer compound.

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

［式中、
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。
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。
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５およびＲ^６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^７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。
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。］

［式中、
ａおよびｂ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^８が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよい。Ｒ^９が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよい。
Ｒ^１０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^１１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^１２、Ｒ^１３、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。
Ｒ^１６およびＲ^１７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^１６が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよい。Ｒ^１７が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよい。
Ｒ^１２とＲ^１４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^１３とＲ^１５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^１２とＲ^１３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^１４とＲ^１５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。]

[式中、
Ｒ^１8およびＲ^１9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^１8およびＲ^１9の少なくとも一方は、水素原子以外の基を示す。］
［２］ 前記Ａｒ^１およびＡｒ^２が、非置換もしくは置換のアリーレン基である、［１］に記載の高分子化合物。
［３］ 前記Ｒ^ＡおよびＲ^Ｂが、非置換もしくは置換のアリール基である、［１］または［２］に記載の高分子化合物。
［４］ 更に、下記式（５）で示される構成単位を含む、［１］〜［３］のいずれか一項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。
但し、式（５）で示される構成単位は、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。］
［５］ 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、［４］に記載の高分子化合物。
［６］ 更に、下記式（６）で示される構成単位を含む、［１］〜［５］のいずれか一項に記載の高分子化合物。

［式中、
ｐは０〜３の整数を示す。ｑは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価の複素環基からなる群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^２５、Ｒ^２６およびＲ^２７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。
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。
但し、式（６）で示される構成単位は、前記式（１）で示される構成単位とは異なる。］
［７］ 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、［６］に記載の高分子化合物。

［式中、
Ｒ^２８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^２９）_２−を示す。Ｒ^２９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を示す。２個存在するＲ^２９は、同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよい。］
［８］ 前記式（１）で示される構成単位と、
下記式（８）で示される構成単位および／または下記式（８’）で示される構成単位と、を含む高分子化合物。

［式中、
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の整数を示す。
Ａｒ⁸は、非置換もしくは置換の（２＋ｎ）価の芳香族複素環基または非置換もしくは置換の（２＋ｎ）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、それらは同一であっても異なっていてもよい。Ｌ^ｂが複数存在する場合、それらは同一であって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、それらは同一であって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。
但し、式（８）で示される構成単位は、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、前記式（４）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。］

［式中、
ｃ’は０または１を示す。
Ａｒ^２０およびＡｒ^４０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^３０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価の複素環基からなる群から選ばれる同一又は異なる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。
Ｘは、前記と同じ意味を表す。
Ｘ’は、１価の架橋性基、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。
但し、式（８’）で示される構成単位は、前記式（１）で示される構成単位および前記式（６）で示される構成単位とは異なる。］
［９］ 前記式（１）で示される構成単位と、下記式（９）で示される構成単位と、を含む高分子化合物。

［式中、
ａ１およびａ２は、それぞれ独立に、０〜４の整数を示し、ａ３は０〜５の整数を示す。
Ｒ³⁰、Ｒ³¹およびＲ³²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。Ｒ³⁰が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよく、Ｒ³¹が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよく、Ｒ³²が複数存在する場合、それらは同一でも異なっていてもよく、互いに結合してそれぞれが結合する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）で示される構成単位の割合が、０．１〜７０モル％である、［１］〜［９］のいずれか一項に記載の高分子化合物。
［１１］ ［１］〜［１０］のいずれか一項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一種以上の材料と、を含有する組成物。
［１２］ 前記発光材料が、三重項発光錯体である、請求項１１に記載の組成物。
［１３］ ［１］〜［１０］のいずれか一項に記載の高分子化合物を含有する有機薄膜。
［１４］ ［１１］または［１２］に記載の組成物を含有する有機薄膜。
［１５］ ［１３］または［１４］に記載の有機薄膜を備える発光素子。
［１６］ 下記式（１Ｍ）で表される化合物。

［式中、
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。
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。
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５およびＲ^６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^７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。
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。
Ｚ^１およびＺ^２は、それぞれ独立に、下記置換基群（下記置換基Ａ群または下記置換基Ｂ群）から選ばれる基を示す。
＜置換基Ａ群＞
塩素原子、臭素原子、ヨウ素原子、
−Ｏ−Ｓ（＝Ｏ）_２Ｒ^３３（Ｒ^３３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。
＜置換基Ｂ群＞
−Ｂ（ＯＲ^３４）_２（Ｒ^３４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^３４は互いに同一でも異なっていてもよい）で示される基、
−ＢＦ_３Ｑ^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^３５）_３（Ｒ^３５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^３５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。］ [1] A structural unit represented by the following formula (1);
A polymer comprising a structural unit represented by the following formula (2), a structural unit represented by the following formula (3), and one or more structural units selected from the group consisting of the structural unit represented by the following formula (4): Compound.

[Where:
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
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 ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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 ⁷ 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 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. ]

[Where:
a and b 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. When a plurality of R ⁸ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. When a plurality of R ⁹ are present, they may be the same or different, and may be bonded together to form a ring structure together with the carbon atoms to which they are bonded.
R ¹⁰ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group.
R ¹¹ 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 ¹² , R ¹³ , R ¹⁴ and R ¹⁵ 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 ¹⁶ and R ¹⁷ 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. When a plurality of R ¹⁶ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. When a plurality of R ¹⁷ are present, they may be the same or different and may be bonded together to form a ring structure together with the carbon atoms to which they are bonded.
R ¹² and R ¹⁴ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹³ and R ¹⁵ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹² and R ¹³ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹⁴ and R ¹⁵ are connected to each other to bond to each other. A ring structure may be formed together with the atoms. ]

[Where
R ¹⁸ and R ¹⁹ 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. However, at least one of R ¹⁸ and R ¹⁹ represents a group other than a hydrogen atom. ]
[2] The polymer compound according to [1], wherein Ar ¹ and Ar ² are an unsubstituted or substituted arylene group.
[3] The polymer compound according to [1] or [2], wherein R ^A and R ^B are an unsubstituted or substituted aryl group.
[4] The polymer compound according to any one of [1] to [3], further including a structural unit represented by the following formula (5).

[Where:
Ar ³ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
However, the structural unit represented by Formula (5) is different from the structural unit represented by Formula (2), the structural unit represented by Formula (3), and the structural unit represented by Formula (4). ]
[5] The polymer compound according to [4], wherein the structural unit represented by the formula (5) is an unsubstituted or substituted fluorenediyl group.
[6] The polymer compound according to any one of [1] to [5], further including a structural unit represented by the following formula (6).

[Where:
p shows the integer of 0-3. q represents 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 the same or selected from the group consisting of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an arylene group and a divalent heterocyclic group; A divalent group in which two or more different groups are linked (the divalent group may have a substituent).
R ²⁵ , R ²⁶ and R ²⁷ 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.
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.
However, the structural unit represented by the formula (6) is different from the structural unit represented by the formula (1). ]
[7] The polymer compound according to [6], wherein the structural unit represented by the formula (6) is a structural unit represented by the following formula (7).

[Where:
R ²⁸ 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 ²⁹ ) ₂ —. R ²⁹ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ²⁹ may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. ]
[8] The structural unit represented by the formula (1),
A polymer compound comprising a structural unit represented by the following formula (8) and / or a structural unit represented by the following formula (8 ′).

[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 an integer of 1 or 2.
Ar ⁸ represents an unsubstituted or substituted (2 + n) -valent aromatic heterocyclic group or an unsubstituted or substituted (2 + n) -valent 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 two or more X exists, they may be the same or different.
However, the structural unit represented by the formula (8) includes the structural unit represented by the formula (2), the structural unit represented by the formula (3), the structural unit represented by the formula (4), and the formula (5). ). ]

[Where:
c ′ represents 0 or 1.
Ar ²⁰ and Ar ⁴⁰ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ³⁰ is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or two or more identical or different groups selected from the group consisting of an arylene group and a divalent heterocyclic group are linked A divalent group (the divalent group may have a substituent).
X represents the same meaning as described above.
X ′ represents a monovalent crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
However, the structural unit represented by the formula (8 ′) is different from the structural unit represented by the formula (1) and the structural unit represented by the formula (6). ]
[9] A polymer compound comprising a structural unit represented by the formula (1) and a structural unit represented by the following formula (9).

[Where:
a1 and a2 each independently represent an integer of 0 to 4, and a3 represents an integer of 0 to 5.
R ³⁰ , R ³¹ and R ³² 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, A substituted monovalent heterocyclic group is shown. When a plurality of R ³⁰ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. If there are a plurality of R ³¹ , they are the same. However, they may be different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded, and when there are a plurality of R ³² , they may be the same or different and A ring structure may be formed together with the carbon atom to which each is bonded. ]
[10] Any one of [1] to [9], wherein the proportion of the structural unit represented by the formula (1) with respect to all the structural units contained in the polymer compound is 0.1 to 70 mol%. The high molecular compound as described in.
[11] The polymer compound according to any one of [1] to [10],
One or more materials selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.
[12] The composition according to claim 11, wherein the luminescent material is a triplet luminescent complex.
[13] An organic thin film containing the polymer compound according to any one of [1] to [10].
[14] An organic thin film containing the composition according to [11] or [12].
[15] A light emitting device comprising the organic thin film according to [13] or [14].
[16] A compound represented by the following formula (1M).

[Where:
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
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 ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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 ⁷ 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 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.
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).
<Substituent group A>
Chlorine atom, bromine atom, iodine atom,
A group represented by —O—S (═O) ₂ R ³³ (R ³³ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group).
<Substituent group B>
A group represented by -B (OR ³⁴ ) ₂ (R ³⁴ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ³⁴ may be the same or different from each other);
A group represented by -BF ₃ 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 ³⁵ ) ₃ (R ³⁵ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ^{35 s} may be the same or different from each other, and are linked to each other to bind to each other. And may form a ring structure together with). ]

  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, and a light-emitting element containing the polymer compound. The present invention can further provide a raw material compound of the 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) is a carbon constituting a ring of a heterocyclic compound (preferably an aromatic heterocyclic compound having aromaticity). The remaining atomic group excluding n hydrogen atoms directly bonded to the atom means a group having a condensed ring. In addition, a group in which two or more rings selected from the group consisting of independent single rings and condensed rings are directly bonded is not included. “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.

  “Aromatic heterocycle” means heteroatom such as oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole In which the heterocycle itself exhibits aromaticity, as well as heterocycles containing heteroatoms such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, and benzopyran themselves are aromatic Means that the heterocyclic ring is condensed with an aromatic ring.

  The “arylene group” means a remaining atomic group obtained by removing two hydrogen atoms directly bonded to carbon atoms constituting a ring from an aromatic hydrocarbon, 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 an atomic group obtained by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon, a group having a condensed ring, an independent benzene ring and a condensed ring A group in which two or more selected from are directly bonded.

  The “halogen atom” refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and is preferably a fluorine atom.

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

  The polymer compound of the present invention is represented by the structural unit represented by the following formula (1), the structural unit represented by the following formula (2), the structural unit represented by the following formula (3), and the following formula (4). One or more structural units selected from the group consisting of structural units.

(Structural unit represented by Formula (1))

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.
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 ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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 ⁷ 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 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.

Ar ¹ and Ar ² are preferably unsubstituted or substituted arylene groups, since the luminance lifetime obtained when the polymer compound of this embodiment is used in the production of a light-emitting device is more excellent.

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 to 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, 6,12-chrysenediyl group, 2,8-chrysenediyl group, and the polymer compound of this embodiment is used for the production of a light emitting device. In this case, since the luminance lifetime obtained is more excellent, 1,4-phenylene group, 2,7-fluorenediyl group, 2,6-naphthalenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group 2,7-phenanthrenediyl group and 2,7-dihydrophenanthrenediyl group are preferable, 1,4-phenylene group and 2,7-fluorenediyl group are preferable, and 1,4-phenylene group is more preferable.

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 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-quinoxalinediyldiyl 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 -Diyl group, 2,7-dibenzofurandiyl group, 2,7-dibenzothiophene diyl group, 2,7-dibenzosilol diyl group.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are superior in luminance lifetime obtained when the polymer compound of this embodiment is used in the production of a light-emitting device. Alternatively, a 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 further preferable.

The unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ may be linear, branched or cyclic, and carbon of the linear alkyl group The number of atoms 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 to 50, preferably 3 to 30 and more preferably 4 to 20 without including a substituted carbon atom.
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-hexyldecyl group.

The unsubstituted or substituted alkoxy group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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 aryl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ does not include the carbon atom of the substituent, and is usually 6 to 60, preferably 6 It is -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 aryloxy group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ does not include the number of carbon atoms of the substituent and is usually 6 to 60. , Preferably 6 to 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.

The number of carbon atoms of the unsubstituted or substituted monovalent heterocyclic group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ does not include the number of carbon atoms of the substituent and is usually 2 to 2. 60, preferably 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, and triazinyl group. A thienyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a pyrimidyl group, and a triazinyl group are preferable because the luminance lifetime obtained when used in the production of an element is more excellent.

R ⁷ is preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group, since the luminance lifetime obtained when the polymer compound of this embodiment is used in the production of a light emitting device is more excellent.

The unsubstituted or substituted alkyl group represented by R ⁷ may be linear, branched or cyclic, and the number of carbon atoms of the linear alkyl group does not include the number of carbon atoms of the substituent. Usually, it is 1-50, Preferably it is 1-30, More preferably, it is 1-20. The number of carbon atoms of the branched alkyl group and the cyclic alkyl group is usually 3 to 50, preferably 3 to 30 and more preferably 4 to 20 without including a substituted carbon atom.
Examples of the unsubstituted or substituted alkyl group represented by R ⁷ 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, an n-pentyl group, and an 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-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyldecyl group, and groups in which hydrogen atoms in these groups are substituted with aryl groups, alkoxy groups, fluorine atoms, etc. Since the luminance life obtained when the polymer compound of the embodiment is used in the production of a light emitting device is more excellent, methyl group, ethyl Group, n-propyl group, n-butyl group, isobutyl group, n-pentyl group, isoamyl group, 2-ethylbutyl group, n-hexyl group, n-heptyl group, cyclohexylethyl group, n-octyl group, 2-ethylhexyl group Group, 3-n-propylheptyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyldecyl group are preferable, n-butyl group, isobutyl group, n-pentyl group Group, isoamyl 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 A dimethyloctyl group, a 2-ethyloctyl group, and a 2-n-hexyldecyl group are more preferable.

Definitions and examples of the unsubstituted or substituted aryl group represented by R ^{7 and the} unsubstituted or substituted monovalent heterocyclic group are the unsubstituted represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. Or it is the same as the definition and example of a substituted aryl group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

R ^A and R ^B are excellent in the stability of the polymer compound of the present embodiment, and more excellent in the luminance life obtained when the polymer compound of the present embodiment is used for manufacturing a shipping element. An unsubstituted or substituted alkyl group, 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.

Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted aryl groups, and unsubstituted or substituted monovalent heterocyclic groups represented by R ^A and R ^B are R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same as the definition and examples of 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, 3,5-dimethylphenyl group 3-n-hexyl-5-methylphenyl group and 3,5-di-n-hexylphenyl group.

The groups represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , 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.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or The definition and examples are the same as those of the substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group.

“Ar ¹ and R ¹ may be connected to each other to form a ring structure with the nitrogen atoms to which they are bonded, and Ar ² and R ⁴ are connected to each other to form a ring structure with the nitrogen atoms to which they are bonded. "May be formed" means that Ar ¹ and R ¹ (or Ar ² and R ⁴ ) are a single bond, -O-, -S-, -C (= O)-, -C (═O) O—, —N (R) —, —C (═O) —N (R) — or —C (R) ₂ — is bonded via a group (R is unsubstituted or A substituted alkyl group or an unsubstituted or substituted aryl group, and when there are a plurality of Rs, they may be the same or different from each other, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded; May be a ring structure).
Definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R are the unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definition and examples of the unsubstituted or substituted aryl group.

“R ^A and R ⁵ may be connected to each other to form a ring structure with the nitrogen atom to which each is bonded, and R ^B and R ⁶ are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. “Optionally formed” means that R ^A and R ⁵ (or R ^B and R ⁶ ) are a single bond, or —O—, —S—, —C (═O) —, —C ( ═O) O—, —N (R) —, —C (═O) —N (R) — or —C (R) ₂ — is bonded via a group (R is as defined above). Represents a ring structure.

  The proportion of the structural unit represented by the formula (1) 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 the present embodiment is excellent. Is preferable, it is more preferable that it is 1-60 mol%, and it is further more preferable that it is 2-50 mol%.

  Examples of the structural unit represented by the formula (1) include structural units represented by the following formulas (1-1) to (1-13), and the polymer compound of the present embodiment is used for the production of a light emitting device. The structural units represented by the formulas (1-1) to (1-7) are preferable, and the structural units represented by the formulas (1-1) to (1-5) are preferable. Is more preferable.

  One type of structural unit represented by the formula (1) may be contained in the polymer compound of this embodiment, or two or more types may be contained.

(Structural unit indicated by (2))

In formula (2), a and b 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. When a plurality of R ⁸ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. When a plurality of R ⁹ are present, they may be the same or different, and may be bonded together to form a ring structure together with the carbon atoms to which they are bonded.
R ¹⁰ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group.
R ¹¹ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group.

  a and b are preferably 0 or 1 and more preferably 0 in view of the ease of synthesis of the polymer compound of the present embodiment.

R ⁸ and R ⁹ are preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group, since the luminance life obtained when the polymer compound of this embodiment is used in the production of a light emitting device is more excellent. .

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 definitions and examples of the groups are the unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , respectively. The definition and examples are the same as those of the unsubstituted or substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group.

Definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted alkoxy group represented by R ¹⁰ are the unsubstituted or substituted alkyl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definition and examples of the group, unsubstituted or substituted alkoxy group.

Unsubstituted or substituted aryl group R ¹¹ represents an unsubstituted or substituted aryloxy group, definitions and examples of the monovalent heterocyclic group unsubstituted or ^{substituted, R 1, R 2, R} 3, R 4, The definitions and examples of the unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, and unsubstituted or substituted monovalent heterocyclic group represented by R ⁵ and R ⁶ are the same.

R ¹⁰ is preferably an unsubstituted or substituted alkyl group, since the luminance life obtained when the polymer compound of this embodiment is used in the production of a light emitting device is more excellent.
R ¹¹ is more excellent in the luminance life obtained when the polymer compound of this embodiment is used in the production of a light-emitting device. Therefore, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group Preferably, an unsubstituted or substituted aryl group is more preferable.
That is, in the combination of R ¹⁰ and R ¹¹ , R ¹⁰ is preferably an unsubstituted or substituted alkyl group, and R ¹¹ is preferably an unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent heterocyclic group. ¹⁰ is an unsubstituted or substituted alkyl group, and R ¹¹ is more preferably an unsubstituted or substituted aryl group.

  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 excellent. Preferably, it is 5 to 70 mol%, more preferably 10 to 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 the present embodiment is used for manufacturing a light emitting device. Therefore, the structural units represented by the formulas (2-1) to (2-14) are preferable, and the structural units represented by the formulas (2-1) to (2-6) are more preferable. preferable.

  The structural unit represented by the formula (2) may be included in the polymer compound of this embodiment only in one kind, or in two or more kinds.

(Structural unit represented by Formula (3))

In formula (3), c and d each independently represent an integer of 0 to 3.
R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ 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 ¹⁶ and R ¹⁷ 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. When a plurality of R ¹⁶ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. When a plurality of R ¹⁷ are present, they may be the same or different and may be bonded together to form a ring structure together with the carbon atoms to which they are bonded.
R ¹² and R ¹⁴ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹³ and R ¹⁵ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹² and R ¹³ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹⁴ and R ¹⁵ are connected to each other to bond to each other. A ring structure may be formed together with the atoms.

  c and d are preferably 0 or 1, and more preferably 0, from the viewpoint of ease of synthesis of the polymer compound of the present embodiment.

R ¹⁶ and R ¹⁷ are preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group, because the luminance life obtained when the polymer compound of this embodiment is used in the production of a light emitting device is more excellent. .

R ¹⁶ and R ¹⁷ 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 include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ The definition and examples are the same as those of the unsubstituted or substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group.

R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ are more excellent in the luminance life obtained when the polymer compound of this embodiment is used in the production of a light-emitting device, so that a hydrogen atom, an unsubstituted or substituted alkyl group, An unsubstituted or substituted alkoxy group is preferred, and an unsubstituted or substituted alkyl group is more preferred.

Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted, represented by R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ The definition and examples of the monovalent heterocyclic group of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, respectively, The definition and examples are the same as those of the unsubstituted or substituted aryl group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group.

At least one selected from the group consisting of R ¹² and R ¹⁴ , R ¹³ and R ¹⁵ , R ¹² and R ¹³ , and R ¹⁴ and R ¹⁵ is linked to each other, and a ring structure together with the carbon atom to which each is bonded Is preferably formed.

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

In formula (3-A), c, d, R ¹⁶ and R ¹⁷ are as defined above.
n1 and n2 each independently represent an integer of 1 to 5.
R ²⁰ , R ²¹ , R ²² and R ²³ 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.
If R ^{20, R 21, R 22} and ^{R 23} are present in plural, each ^{R 20,} R ^{21, R 22} and ^{R 23} there are a plurality may be the same or different from each ^other, R ^{20, R 21,} Adjacent groups of R ²² and R ²³ may be linked together to form a ring structure together with the carbon atoms to which they are bonded.

R ²⁰ , R ²¹ , R ²² and R ^{23 each} have a higher luminance lifetime obtained when the polymer compound of this embodiment is used in the production of a light-emitting device, so that a hydrogen atom, an unsubstituted or substituted alkyl group, An unsubstituted or substituted aryl group is preferable, and a hydrogen atom and an unsubstituted or substituted alkyl group are more preferable.

Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted represented by R ²⁰ , R ²¹ , R ²² and R ²³ The definition and examples of the monovalent heterocyclic group of R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted Or it is the same as the definition and example of a substituted aryl group, an unsubstituted or substituted aryloxy group, and an unsubstituted or substituted monovalent heterocyclic group.

In the structural unit represented by the formula (3-A), for example, when a skeleton moiety represented by the following formula (3-A1) is included, examples of the stereoisomers include the following formula (3-a1), It is represented by formula (3-b1), formula (3-c1), and formula (3-d1). In the following formulae, R ^m and R ⁿ each independently represent 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 ²⁰ , R ²¹ , R ²² and R ²³ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded”. For example, groups bonded to the same carbon atom may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded, and when n1 and n2 are 2 or more, adjacent carbon atoms It means that the groups bonded to each other may be linked together to form a ring structure together with the carbon atoms to which they are bonded.

The formed ring structure may have a substituent, such as an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryloxy group, a halogen atom, a non-substituted group. Examples thereof include a substituted 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 aryloxy groups, halogen atoms, unsubstituted or substituted monovalent heterocyclic groups are R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, unsubstituted or The definition and examples of the substituted monovalent heterocyclic group are the same.

  n1 and n2 are preferably 3 to 5, and preferably 3 or 4, since the light emission efficiency obtained when the polymer compound of the present embodiment is used in the production of a light emitting device is more excellent. More preferably. n1 and n2 may be the same or different from each other, but it is preferable that n1 and n2 are the same because the synthesis of the polymer compound of the present embodiment is facilitated.

  The proportion of the structural unit represented by the formula (3) (which may be the structural unit represented by the formula (3-A)) is more excellent 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, It is more preferable that it is 5-70 mol%, It is further more preferable that it is 10-60 mol%.

  The structural unit represented by the formula (3) (which may be the structural unit represented by the formula (3-A)) may be included in the polymer compound of this embodiment only in one type. More than one species may be included.

  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 (3-30). And the structural unit represented by the formula (3-1) to the formula (3-14) is preferable because the luminance life obtained when the polymer compound of the present embodiment is used for the production of a light emitting device is more preferable. The structural units represented by (3-1) to formula (3-9) are more preferable.

(Structural unit represented by Formula (4))

In formula (4), R ¹⁸ and R ¹⁹ 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 of R ¹⁸ and R ¹⁹ represents a group other than a hydrogen atom.

R ¹⁸ and R ¹⁹ are preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group because the luminance life obtained when the polymer compound of the present embodiment is used in the production of a light emitting device is more excellent. An unsubstituted or substituted alkyl group is more preferred.

The unsubstituted or substituted alkyl group represented by R ¹⁸ and R ¹⁹ may be linear, branched or cyclic, and the number of carbon atoms of the linear alkyl group includes the number of carbon atoms of the substituent. It is 1-50 normally, Preferably it is 3-30, More preferably, it is 4-20. The number of carbon atoms of the branched alkyl group and the cyclic alkyl group is usually 3 to 50, preferably 3 to 30 and more preferably 4 to 20 without including a substituted carbon atom.
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, 2-ethylbutyl group, and n-hexyl. Group, cyclohexyl group, n-heptyl group, cyclohexylmethyl 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-hexyldecyl group, and groups in which hydrogen atoms in these groups are substituted with aryl groups, alkoxy groups, fluorine atoms, etc., include methyl group, ethyl group, n-propyl group , N-butyl group, isobutyl group, n-pentyl group, isoamyl group, 2-ethylbutyl group, n-hexyl group, n- Ptyl 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-hexyldecyl Group is more preferable, n-butyl group, isobutyl group, n-pentyl group, isoamyl 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-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyldecyl group are more preferable, cyclohexylethyl group, 3-n-propylheptyl group, n-decyl group, n-octyl group, 2-ethylhexyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group Preferred.

Definitions and examples of unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, unsubstituted or substituted monovalent heterocyclic groups represented by R ¹⁸ and R ¹⁹ are R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ represent an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted monovalent group This is the same as the definition and example of the heterocyclic group of.

  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 for the structural unit represented by the formula (4), only one type may be included in the polymer compound of this embodiment, or two or more types may be included.

  Examples of the structural unit represented by the formula (4) include structural units represented by the following formulas (4-1) to (4-14). The polymer compound of the present embodiment is used for the production of a light emitting device. Since the luminance lifetime obtained when used is more excellent, the structural units represented by the formulas (4-1) to (4-12) are preferable, and are represented by the formulas (4-1) to (4-7). More preferred is a structural unit.

  Since the polymer compound of this embodiment has a higher luminance lifetime obtained when used in the production of a light-emitting device, the polymer compound includes a structural unit represented by the formula (1) and a structural unit represented by the formula (2). A molecular compound or a polymer compound containing a structural unit represented by formula (1) and a structural unit represented by formula (4), or a structural unit represented by formula (1) and represented by formula (2) It is preferably a polymer compound containing a structural unit and a structural unit represented by formula (4). The structural unit represented by formula (1), the structural unit represented by formula (2), and the formula (4) It is more preferable that the polymer compound contains a structural unit.

(Structural unit represented by Formula (5))
The polymer compound of this embodiment may further contain a structural unit represented by the following formula (5).

In Formula (5), Ar ³ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
However, the structural unit represented by Formula (5) is different from the structural unit represented by Formula (2), the structural unit represented by Formula (3), and the structural unit represented by Formula (4).

Ar ³ is excellent in stability of the polymer compound according to the present embodiment, and more excellent in luminance life obtained when the polymer compound of the present embodiment is used for manufacturing a light-emitting device. Substituted arylene groups are preferred.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ³ is preferably 6 to 60, more preferably 6 to 30, and further preferably 6 to 18 without including the carbon atoms of the substituent. It is.
Examples of the arylene group include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthalenediyl group, 1,5-naphthalenediyl group, and 2,6-naphthalenediyl group. Group, 2,7-phenanthrenediyl group, 5,12-naphthacenediyl group, 2,7-fluorenediyl group, 3,6-fluorenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group 1,6-pyrenediyl group, 2,7-pyrenediyl group, 3,9-perylenediyl group, 3,10-perylenediyl group, 6,12-chrysenediyl group, 2,8-chrysenediyl group, Since the luminance life obtained when a polymer compound is used in the production of a light emitting device is more excellent, 1,4-phenylene, 2,7-fluorenediyl, 2,7 Phenanthrenediyl are 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, and is usually 2 to 60, preferably 3 to 30, more preferably 4-15.
Examples of the divalent heterocyclic group 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, 2,1,3-benzothiadiazole-4,7-diyl group, 2,7 -A dibenzofurandiyl group, a 2,7-dibenzothiophene diyl group, and a 2,7-dibenzosilol diyl group are mentioned.

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 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.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or The definition and examples are the same as those of the substituted aryloxy group and the unsubstituted or substituted monovalent 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%.

  One type of structural unit represented by the formula (5) may be contained in the polymer compound of this embodiment, or two or more types may be contained.

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

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , R ²¹ , R ²² , R ²³ , R ^A , R ^B , Ar ¹ , Ar ² and Ar ³ may have a substituent. As 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 heterocyclic group And an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferable.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or The definition and examples are the same as those of the substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group.

(Structural unit represented by Formula (6))
The polymer compound of this embodiment may further contain a structural unit represented by the following formula (6).

In formula (6), p represents an integer of 0 to 3. q represents 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 the same or selected from the group consisting of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an arylene group and a divalent heterocyclic group; A divalent group in which two or more different groups are linked (the divalent group may have a substituent).
R ²⁵ , R ²⁶ and R ²⁷ 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.
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.
However, the structural unit represented by the formula (6) is different from the structural unit represented by the formula (1).

  p is more preferably 1 because the luminance lifetime obtained when the polymer compound of the present embodiment is used in the production of a light emitting device is more excellent.

  q is 0 because it is easy to produce the polymer compound of this embodiment and the luminance life obtained when the polymer compound of this embodiment is used in the production of a light-emitting device is better. preferable.

Ar ⁴ , Ar ⁵ , Ar ⁶ and Ar ⁷ are the luminance 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. An unsubstituted or substituted arylene group is preferred because of its longer life.

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 include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthalenediyl group, 1,5-naphthalenediyl group, and 2,6-naphthalenediyl group. 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, 6,12-chrysenediyl Group, 2,8-chrysenediyl group, 1,4-phenylene group, 2,6-naphthalenediyl group, 2,7-fluorenediyl group 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthrenediyl group, 2,7-dihydrophenanthenediyl group, 1,6-pyrenediyl group are preferable, 1,4-phenylene group, 2 7-Fluorangeyl is more preferred.

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, and is usually 2 to 60, preferably 3 30, more preferably 4-15.
Examples of the divalent heterocyclic group 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, 3,7-phenoxazinediyl group, 3,7-phenothiazinediyl group, 2, 8-phenothiazinediyl group, 4,6-phenothiazinediyl group, 2,1,3-benzothiadiazole-4,7-diyl group, 2,7-dibenzofurandiyl group, 2,7-dibenzothiophenediyl group, 2,7 -A dibenzosilol diyl group is mentioned.

Examples of the divalent group in which two or more identical or different groups selected from the group consisting of an arylene group and a divalent heterocyclic group represented by Ar ⁵ and Ar ⁷ are linked include the following formulas (1a-1) to formulas: (1a-7) is mentioned, and the group represented by the formula (1a-1) is preferable.

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.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ Or it is the same as the definition and example of a substituted monovalent heterocyclic group.

Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted aryl groups, and unsubstituted or substituted monovalent heterocyclic groups represented by R ²⁵ , R ²⁶ and R ²⁷ are R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same as the definition 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 for the structural unit represented by the formula (6), only one type may be contained in the polymer compound of this embodiment, or two or more types may be contained.

  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 the formula (7), R ²⁸ 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 ²⁹ ) ₂ —. R ²⁹ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ²⁹ may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded.

R ²⁸ is more stable because the stability of the polymer compound of this embodiment is improved and the luminance life obtained when the polymer compound of this embodiment is used in the production of a light-emitting device is excellent. Or a substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group, preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group. More preferably, it is an unsubstituted or substituted aryl group.

Definitions and examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted aryl group, and unsubstituted or substituted monovalent heterocyclic group represented by R ²⁸ are R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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.

  Z is preferably a single bond or an oxygen atom, and more preferably an oxygen atom, since the luminance lifetime obtained when used for the production of the light emitting device of the polymer compound of the present embodiment is more excellent.

The definition and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ²⁹ are the unsubstituted or substituted alkyl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definitions and examples of the group, unsubstituted or substituted aryl group.

  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. Since the luminance lifetime obtained when used is more excellent, the structural units represented by the formulas (7-1) to (7-5) are preferable, and the structural unit represented by the formula (7-4) is more preferable.

  The polymer compound of the present invention includes a structural unit represented by the above formula (1), a structural unit represented by the following formula (8), and / or a structural unit represented by the following formula (8 ′).

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 an integer of 1 or 2.
Ar ⁸ represents an unsubstituted or substituted (2 + n) -valent aromatic heterocyclic group or an unsubstituted or substituted (2 + n) -valent 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 two or more X exists, they may be the same or different.
However, the structural unit represented by the formula (8) includes the structural unit represented by the formula (2), the structural unit represented by the formula (3), the structural unit represented by the formula (4), and the formula (5). ).

  na is preferably an integer of 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 an integer of 0 to 10, more preferably an integer of 0 to 8, and even more preferably 0, because the production of the polymer compound of the present embodiment becomes easier.

  n is preferably 2 because the crosslinkability of the polymer compound of the present embodiment is excellent.

  nA is preferably 0 because the production of the polymer compound of this embodiment becomes easier.

The number of carbon atoms of the unsubstituted or substituted (2 + n) -valent aromatic hydrocarbon 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. More preferably, it is 6-18.
Examples of the arylene group portion excluding n substituents of the (2 + n) -valent aromatic hydrocarbon group include a 1,4-naphthalenediyl group, a 1,5-naphthalenediyl group, and a 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 group, 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 and 1,6-pyrenediyl group are preferable, 2,6-naphthalenediyl group and 2,7-fluorenediyl group are preferable. Further preferred.

The number of carbon atoms of the unsubstituted or substituted (2 + n) -valent heterocyclic group represented by Ar ⁸ does not include the number of carbon atoms of the substituent, and is usually 2 to 60, preferably 3 to 30, more preferably 3 to 3. 15.
Examples of the divalent heterocyclic group part excluding n substituents of the (2 + n) -valent heterocyclic group represented by Ar ⁸ include a 2,5-thiophenediyl group, a 2,5-pyrrolediyl group, 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-quinoxaline Diyl 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-diyl group, 2,7-dibenzofurandiyl group, 2,7-dibenzothiophenediyl group, 2,7-dibenzoshiro And urdiyl group.

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. Aryloxy groups, halogen atoms, unsubstituted or substituted monovalent heterocyclic groups, and cyano groups.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or The definition and examples are the same as those of the substituted aryloxy group and the unsubstituted or substituted monovalent 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 the unsubstituted or substituted alkyl group and the unsubstituted or substituted alkoxy group as the substituent are unsubstituted or substituted alkyl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definition and examples of the group, unsubstituted or substituted alkoxy group.

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 an aziridinyl group, an azetidinyl group, an azide group, an epoxy group, an oxetanyl group, an alkenyl group, an alkynyl group, and a group having cyclobutane. Therefore, monovalent crosslinkable groups represented by the following formula (X-1) and the following formula (X-2) are 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.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or The definition and examples are the same as those of the substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group.

  In formula (X-1), benzocyclobutane may have a substituent.

In formula (X-2), ne and nf each independently represent 0 or 1.
L ^X1 represents an oxygen atom, a sulfur atom, a carbonyl group or a group represented by —O—CO—.
R ²⁹ , 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, unsubstituted or A substituted aryloxy group, an unsubstituted or substituted monovalent heterocyclic group, a halogen atom, a cyano group or a nitro group is shown. In addition, the 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.

  ne and nf are preferably 0 because the production of the polymer compound of this embodiment becomes easier.

R ²⁹ , R ³⁰ , R ³¹ , R ³² and R ³³ are superior in luminance lifetime obtained when the polymer compound of this embodiment is used in the production of a light-emitting device. An alkyl group and unsubstituted are preferable, and a hydrogen atom is more preferable.

R ²⁹ , R ³⁰ , R ³¹ , R ³² and R ³³ 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, Definitions and examples of the substituted or substituted monovalent heterocyclic group include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, The definition and examples are the same as those of the unsubstituted or substituted aryl group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent 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 for the structural unit represented by Formula (8), only one type may be included in the polymer compound of the present embodiment, or two or more types may be included.

In the formula (8 ′), c ′ represents 0 or 1.
Ar ²⁰ and Ar ⁴⁰ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ³⁰ is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or two or more identical or different groups selected from the group consisting of an arylene group and a divalent heterocyclic group are linked A divalent group (the divalent group may have a substituent).
X represents the same meaning as described above.
X ′ represents a monovalent crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
However, the structural unit represented by the formula (8 ′) is different from the structural unit represented by the formula (1) and the structural unit represented by the formula (6).

  c ′ is 0 because the production of the polymer compound of this embodiment becomes easier and the hole transport property and durability of the light-emitting device produced using the polymer compound of this embodiment are superior. It is preferable.

Ar ²⁰ , Ar ^30, and Ar ⁴⁰ are preferably unsubstituted or substituted arylene groups, because the hole transport property and durability of the light-emitting device produced using the polymer compound of this embodiment are excellent.

Definitions and examples of unsubstituted or substituted arylene groups represented by Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ are definitions and examples of unsubstituted or substituted arylene groups represented by Ar ⁴ , Ar ⁵ and Ar ⁶ in the above formula (6). Is the same.

The definition and examples of the unsubstituted or substituted divalent heterocyclic group represented by Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ are the unsubstituted or substituted divalent represented by Ar ⁴ , Ar ⁵ and Ar ⁶ in the above formula (6). This is the same as the definition and example of the heterocyclic group of.

The definition and example of a divalent group in which two or more identical or different groups selected from the group consisting of an arylene group represented by Ar ³⁰ and a divalent heterocyclic group are connected are as follows: Arylene represented by Ar ⁵ in the above formula (6) This is the same as the definition and examples of a divalent group in which two or more identical or different groups selected from the group consisting of a group and a divalent heterocyclic group are linked.

The groups represented by Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ 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, Examples thereof include an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definition of a substituted or unsubstituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent heterocyclic group And examples thereof include an unsubstituted or substituted alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ , an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or The definition and examples are the same as those of the substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group.

  The definition and example of the monovalent crosslinkable group represented by X and X ′ are the same as the definition and example of the monovalent crosslinkable group represented by X in Formula (8).

Definitions and examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted aryl group, and unsubstituted or substituted monovalent heterocyclic group represented by X ′ are R ¹ , R ² , R ³ , R ⁴ , R ^5. And R ⁶ are the same as the definition and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group.

  X ′ is preferably the same monovalent crosslinkable group as X because the polymer compound of the present embodiment can be produced more easily and the crosslinkability of the polymer compound of the present embodiment is excellent.

  The proportion of the structural unit represented by the formula (8 ′) is the sum of all the structural units of the polymer compound because the stability of the polymer compound of this embodiment is more excellent and the crosslinkability of this embodiment is more excellent. Is preferably 0.5 to 40 mol%, more preferably 3 to 30 mol%, and still more preferably 3 to 20 mol%.

  As for the structural unit represented by the formula (8 '), only one type of structural unit may be contained in the polymer compound of this embodiment, or two or more types may be contained.

  Examples of the structural unit represented by the formula (8) include structural units represented by the following formulas (8-1) to (8-24). Examples of the structural unit represented by the formula (8 ′) include And structural units represented by the following formulas (8′-1) to (8′-6). Among these, since the crosslinkability of the polymer compound of the present embodiment is excellent, Formula (8-1) to Formula (8-20) and Formula (8′-1) to Formula (8′-4) are preferable. Formula (8-1) to Formula (8-10) and Formula (8′-1) to Formula (8′-3) are more preferable. 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.

In formula (9),
a1 and a2 each independently represent an integer of 0 to 4, and a3 represents an integer of 0 to 5.
R ³⁰ , R ³¹ and R ³² 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, A substituted monovalent heterocyclic group is shown. When a plurality of R ³⁰ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. If there are a plurality of R ³¹ , they are the same. However, they may be different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded, and when there are a plurality of R ³² , they may be the same or different and A ring structure may be formed together with the carbon atom to which each is bonded.

  As the structural unit represented by the formula (9), a structural unit represented by the following formula (9-1) is preferable.

［式（９−１）中、
Ｒ^３２ａは、水素原子、アルキル基又はアリール基を表す。複数あるＲ^３２ａは、それぞれ同一でも異なっていてもよく、互いに結合してそれぞれが結合する炭素原子とともに環構造を形成していてもよいが、少なくとも一つのＲ^３２ａは、水素原子以外の基を表す。］

[In Formula (9-1),
R ^32a represents a hydrogen atom, an alkyl group or an aryl group. The plurality of R ^32a may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded, but at least one R ^32a represents a group other than a hydrogen atom. Represent. ]

  Examples of the structural unit represented by the formula (9-1) include structural units represented by the following formulas (9-001) to (9-008).

  Examples of preferable combinations of the structural units in the polymer compound of the present embodiment are shown below. In addition, Q1-Q116 represents the molar ratio of the structural unit in a parenthesis with respect to all the structural units of a high molecular compound.

In said formula, Q1 shows the number of 3-20, Q2 shows the number of 20-50, Q3 shows the number of 40-60. 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.
Q15 represents a number from 3 to 20, Q16 represents a number from 10 to 50, and Q17 represents a number from 20 to 50. However, Q15 + Q16 + Q17 = 100.
Q18 represents a number from 3 to 20, Q19 represents a number from 20 to 50, and Q20 represents a number from 40 to 60. However, Q18 + Q19 + Q20 = 100.
Q21 represents a number from 3 to 20, Q22 represents a number from 10 to 50, Q23 represents a number from 10 to 50, and Q24 represents a number from 20 to 50. However, Q21 + Q22 + Q23 + Q24 = 100.
Q25 represents a number of 3 to 20, Q26 represents a number of 40 to 60, Q27 represents a number of 30 to 50, and Q28 represents a number of 1.5 to 10. However, Q25 + Q26 + Q27 + Q28 = 100.
Q29 shows the number of 3-20, Q30 shows the number of 10-50, Q31 shows the number of 40-60, Q32 shows the number of 1.5-10. However, Q29 + Q30 + Q31 + Q32 = 100.
Q33 represents a number of 20 to 40, Q34 represents a number of 3 to 20, Q35 represents a number of 1.5 to 10, and Q36 represents a number of 40 to 60. However, Q33 + Q34 + Q35 + Q36 = 100.
Q37 represents a number from 3 to 20, Q38 represents a number from 20 to 50, Q39 represents a number from 20 to 50, Q40 represents a number from 1.5 to 10, Q41 represents from 1.5 to 10 Indicates a number. However, Q37 + Q38 + Q39 + Q40 + Q41 = 100.
Q42 represents a number of 3 to 20, Q43 represents a number of 40 to 60, Q44 represents a number of 10 to 50, and Q45 represents a number of 1.5 to 10. However, Q42 + Q43 + Q44 + Q45 = 100.
Q46 represents a number from 3 to 20, Q47 represents a number from 40 to 60, Q48 represents a number from 10 to 50, and Q49 represents a number from 1.5 to 10. However, Q46 + Q47 + Q48 + Q49 = 100.
Q50 represents a number from 3 to 20, Q51 represents a number from 20 to 50, and Q52 represents a number from 40 to 60. However, Q50 + Q51 + Q52 = 100.
Q53 represents a number of 3 to 20, Q54 represents a number of 40 to 60, Q55 represents a number of 10 to 50, and Q56 represents a number of 10 to 50. However, Q53 + Q54 + Q55 + Q56 = 100.
Q57 represents a number from 3 to 20, Q58 represents a number from 40 to 60, Q59 represents a number from 30 to 50, and Q60 represents a number from 1.5 to 10. However, Q57 + Q58 + Q59 + Q60 = 100.
Q61 represents a number of 20 to 40, Q62 represents a number of 10 to 50, Q63 represents a number of 40 to 60, and Q64 represents a number of 3 to 20. However, Q61 + Q62 + Q63 + Q64 = 100.
Q65 represents a number from 3 to 20, Q66 represents a number from 40 to 60, Q67 represents a number from 10 to 50, Q68 represents a number from 1.5 to 10, Q69 represents a number from 1.5 to 10 Indicates a number. However, Q65 + Q66 + Q67 + Q68 + Q69 = 100.
Q70 represents a number from 3 to 20, Q71 represents a number from 40 to 60, Q72 represents a number from 20 to 50, and Q73 represents a number from 1.5 to 10. However, Q70 + Q71 + Q72 + Q73 = 100.
Q74 represents a number of 20 to 40, Q75 represents a number of 3 to 20, Q76 represents a number of 1.5 to 10, and Q77 represents a number of 40 to 60. However, Q74 + Q75 + Q76 + Q77 = 100.
Q78 represents a number from 3 to 20, Q79 represents a number from 20 to 50, Q80 represents a number from 20 to 50, and Q81 represents a number from 10 to 50. However, Q78 + Q79 + Q80 + Q81 = 100.
Q82 represents a number from 3 to 20, Q83 represents a number from 20 to 60, and Q84 represents a number from 20 to 60. However, Q82 + Q83 + Q84 = 100.
Q85 represents a number from 3 to 20, Q86 represents a number from 40 to 90, and Q87 represents a number from 1.5 to 10. However, Q85 + Q86 + Q87 = 100.
Q88 represents a number of 3 to 20, Q89 represents a number of 40 to 60, Q90 represents a number of 10 to 50, and Q91 represents a number of 10 to 50. However, Q88 + Q89 + Q90 + Q91 = 100.
Q92 represents a number of 20 to 40, Q93 represents a number of 3 to 20, Q94 represents a number of 3 to 20, Q95 represents a number of 1.5 to 10, and Q96 represents a number of 40 to 60. Show. However, Q92 + Q93 + Q94 + Q95 + Q96 = 100.
Q97 represents a number from 3 to 20, Q98 represents a number from 40 to 60, and Q99 represents a number from 20 to 50. However, Q97 + Q98 + Q99 = 100.
Q100 represents a number from 3 to 20, Q101 represents a number from 20 to 50, Q102 represents a number from 40 to 60, and Q103 represents a number from 1.5 to 10. However, Q100 + Q101 + Q102 + Q103 = 100.
Q104 represents a number from 3 to 20, and Q105 represents a number from 80 to 97. However, Q104 + Q105 = 100.
Q106 represents a number of 3 to 20, Q107 represents a number of 40 to 60, Q108 represents a number of 20 to 50, and Q109 represents a number of 1.5 to 10. However, Q106 + Q107 + Q108 + Q109 = 100.
Q110 represents a number of 20 to 40, Q111 represents a number of 3 to 20, Q112 represents a number of 40 to 60, and Q113 represents a number of 1.5 to 10. However, Q110 + Q111 + Q112 + Q113 = 100.
Q114 represents a number from 3 to 20, Q115 represents a number from 20 to 50, and Q116 represents a number from 20 to 60. However, Q114 + Q115 + Q116 = 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 bonded to an aryl group or a monovalent heterocyclic group (particularly a monovalent aromatic heterocyclic group) via a carbon-carbon bond. Groups (specifically, substituents described in JP-A-9-45478).

  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.

  The polymer compound of the present embodiment is represented by, for example, a compound represented by the following formula (1M), a compound represented by the following formula (2M), a compound represented by the following formula (3M), and the following formula (4M). It can be produced by subjecting a compound, a compound represented by the following formula (8M), and one or more compounds selected from the group consisting of the following formula (8 ′) to condensation polymerization. In addition, when the condensation polymerization is performed, the other compound is 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). A compound may be further used.

In formula (1M), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above, and Z ¹ and Z ² independently represents a group selected from the following substituent group (the following substituent group A or the following substituent group B).
In formula (2M), R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , a and b are as defined above, and Z ³ and Z ⁴ are each independently the following substituent group (substituent group A below) Or a group selected from the following substituent group B).
In the formula (3M), R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , c and d are as defined above, and Z ⁵ and Z ⁶ are each independently the following substituent group A group selected from (the following substituent group A or the following substituent group B) is shown.
In the formula (4M), R ¹⁸ and R ¹⁹ are as defined above, and Z ⁷ and Z ⁸ are each independently selected from the following substituent group (the following substituent group A or the following substituent group B). Indicates a group.
In the formula (5M), Ar ³ is as defined above, and Z ¹¹ and Z ¹² 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 (6M), Ar ⁴ , Ar ⁵ , Ar ⁶ , Ar ⁷ , R ²⁵ , R ²⁶ , R ²⁷ , p and q are as defined above, and Z ¹³ and Z ¹⁴ are each independently the following: A group selected from a substituent group (the following substituent group A or the following substituent group B) is shown.
In formula (7M), R ²⁸ and Z are as defined above, and Z ¹⁵ and Z ¹⁶ are each independently a group selected from the following substituent group (the following substituent group A or the following substituent group B). Indicates.
In formula (8M), Ar ⁸ , L ^A , L ^a , L ^b , X, nA, na, nb and n are as defined above, and Z ⁹ and Z ¹⁰ are each independently the following substituent groups A group selected from (the following substituent group A or the following substituent group B) is shown.
In the formula (8′M), Ar ²⁰ , Ar ³⁰ , Ar ⁴⁰ , X, X ′ and c ′ have the same meanings as described above, and Z ¹⁷ and Z ¹⁸ each independently represent the following substituent group (the following substituents) Group selected from group A group or the following substituent group B).

<Substituent group A>
A group represented by a chlorine atom, a bromine atom, an iodine atom, —O—S (═O) ₂ R ³³ (R ³³ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group).

<Substituent group B>
A group represented by -B (OR ³⁴ ) ₂ (R ³⁴ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ³⁴ may be the same or different from each other);
A group represented by -BF ₃ 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 ³⁵ ) ₃ (R ³⁵ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ^{35 s} may be the same or different from each other, and are linked to each other to bind to each other. And may form a ring structure together with).

The definition and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ³³ are the unsubstituted or substituted alkyl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definition and examples of the group, unsubstituted or substituted aryl group.

The definition and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ³⁴ are the unsubstituted or substituted alkyl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definition and examples of the group, unsubstituted or substituted aryl group.

The definition and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ³⁵ are the unsubstituted or substituted alkyl represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^6. The same as the definition and examples of the group, unsubstituted or substituted aryl group.

  The compound having a group selected from the substituent group A and the compound having a group selected from the substituent group B are subjected to condensation polymerization by a known coupling reaction, and the group selected from the substituent group A and the 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 compound 1M and Z ³ and Z ⁴ in compound 2M are groups selected from the substituent group A, Z ⁵ and Z ⁶ (or Z in compound 3M (or compound 4M)) ^{As 7} and Z ⁸ ), a group selected from the substituent group B can be selected. In addition, when Z ¹ and Z ² in compound 1M and Z ³ and Z ⁴ in compound 2M are groups selected from the substituent B group, Z ⁵ and Z ⁶ (or Z in compound 3M (or compound 4M)) ^{As 7} and Z ⁸ ), a group selected from the substituent group A can be selected.

  As the compounds represented by the formula (1M) to the formula (8′M), those synthesized and isolated in advance may be used, or prepared in a reaction system and used as they are, but synthesized and isolated in advance. It is preferable to use what was done.

  Examples of the condensation polymerization method include a method in which a compound represented by the formula (1M) to the formula (8′M) is reacted using an appropriate catalyst or an appropriate 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 thereof is preferably 0.00001 to 3 molar equivalents as the amount of transition metal with respect to the total number of moles of the compounds represented by formula (1M) to formula (8′M). 0.0005-0.5 molar equivalent is more preferable, and 0.0001-0.2 molar equivalent is still more preferable.

  The organic solvent varies depending on the type and reaction of the compound represented by the formula (1M) to formula (8′M), but 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 such that the total concentration of the compounds represented by the formulas (1M) to (8′M) is usually 0.1 to 90% by weight, preferably 1 to 50% by weight, more preferably 2 to 30%. It is the amount that becomes mass%.

  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), and Z ^T Represents a group selected from the group consisting of the substituent group A and the substituent group B.

Ar ^T represents an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group (particularly, an unsubstituted or substituted monovalent aromatic heterocyclic group), R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are the same as the unsubstituted or substituted aryl group and the unsubstituted or substituted monovalent heterocyclic group (particularly, the unsubstituted or substituted monovalent aromatic heterocyclic group). The thing can be illustrated.

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

[Compound]
The compound of the present invention is a compound represented by the following formula (1M), and can be suitably used as a raw material compound of the polymer compound of the present invention.

In the formula (1M), Ar ¹ , Ar ² , R ^A , R ^B , R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ and R ⁷ represent the same meaning as described 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).
<Substituent group A>
Chlorine atom, bromine atom, iodine atom,
A group represented by —O—S (═O) ₂ R ³³ (R ³³ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group).
<Substituent group B>
A group represented by -B (OR ³⁴ ) ₂ (R ³⁴ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ³⁴ may be the same or different from each other);
A group represented by -BF ₃ 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 ³⁵ ) ₃ (R ³⁵ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ^{35 s} may be the same or different from each other, and are linked to each other and bonded to each other. And may form a ring structure together with).

  The method for producing the compound represented by the formula (1M) will be described below by taking the compound represented by the formula (1MM) as an example. The compound represented by the formula (1MM) can be produced, for example, by the method described in the following scheme 1.

In the formula (1MM), Ar ¹ , R ^A and Z ¹ represent the same meaning as described above. A plurality of Ar ¹ may be the same or different from each other, a plurality of R ^A may be the same or different from each other, and a plurality of Z ¹ may be the same or different from each other.

スキーム１

Scheme 1

In Scheme 1,
XX represents a bromine atom or an iodine atom, and more preferably an iodine atom.
Z ¹ is preferably a chlorine atom or a bromine atom, and more preferably a bromine atom.
Z ² is preferably a bromine atom or an iodine atom, and more preferably an iodine atom.

As the compound represented by the formula (1 mm ¹ ), for example, a commercial product (Tokyo Chemical Industry Co., Ltd.) can be purchased and used.
The compound represented by the formula (1 mm ² ) can be synthesized by reacting the compound represented by the formula (1 mm ¹ ) with a predetermined halide (R ⁷ -XX).
The compound represented by the formula (1 mm ³ ) can be synthesized by a coupling reaction between the compound represented by the formula (1 mm ² ) and a predetermined amine compound (R ^A —NH ₂ ).
The compound represented by the formula (1MM) can be synthesized by a coupling reaction between a compound represented by the formula (1 mm ³ ) and a predetermined compound (Z ² -Ar ¹ -Z ¹ ). In addition, the compound represented by the formula (1MM) can be converted into a group selected from the substituent group B (or a group selected from the substituent group A) by using a known reaction, if necessary. .

[Composition]
The composition of the present invention is a composition containing the polymer compound of the present invention and one or more materials 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.

  Here, the organic solvent is not particularly limited as long as the polymer compound of the present invention is dissolved or dispersed, and examples thereof include the following organic solvents (hereinafter sometimes referred to as “solvent group”).

  Aromatic hydrocarbon solvents: toluene, xylene (each isomer or a mixture thereof), 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, mesitylene (1,3,5-trimethylbenzene), Ethylbenzene, propylbenzene, isopropylbenzene, butylbenzene, isobutylbenzene, 2-phenylbutane, tert-butylbenzene, pentylbenzene, neopentylbenzene, isoamylbenzene, hexylbenzene, cyclohexylbenzene, heptylbenzene, octylbenzene, 3-propyltoluene 4-propyltoluene, 1-methyl-4-propylbenzene, 1,4-diethylbenzene, 1,4-dipropylbenzene, 1,4-di-tert-butylbenzene, indane, tetralin (1,2,3, 4 Tetrahydronaphthalene), and the like.

  Aliphatic hydrocarbon solvents: n-pentane, n-hexane, cyclohexane, methylcyclohexane, n-heptane, n-octane, n-nonane, n-decane, decalin and the like.

  Aromatic ether solvents: anisole, ethoxybenzene, propoxybenzene, butoxyoxybenzene, pentyloxybenzene, cyclopentyloxybenzene, hexyloxybenzene, cyclohexyloxybenzene, heptyloxybenzene, octyloxybenzene, 2-methylanisole, 3- Methylanisole, 4-methylanisole, 4-ethylanisole, 4-propylanisole, 4-butylanisole, 4-pentylanisole, 4-hexylanisole, diphenylether, 4-methylphenoxybenzene, 4-ethylphenoxybenzene, 4-propyl Phenoxybenzene, 4-butylphenoxybenzene, 4-pentylphenoxybenzene, 4-hexylphenoxybenzene, 4-phenoxytoluene, 3- Enokishitoruen, 1,3-dimethoxybenzene, 2,6-dimethyl anisole, 2,5-dimethyl anisole, 2,3-dimethyl anisole, 3,5- dimethyl anisole, and the like.

  Aliphatic ether solvents: tetrahydrofuran, dioxane, dioxolane and the like.

  Ketone solvents: acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, acetophenone, and the like.

  Ester solvent: ethyl acetate, butyl acetate, methyl benzoate, ethyl cellosolve acetate and the like.

  Chlorinated solvent: methylene chloride, chloroform, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene and the like.

  Alcohol solvents: methanol, ethanol, propanol, isopropanol, cyclohexanol, phenol, etc.

  Polyhydric alcohol and its derivatives: 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-hexane Diol etc.

  Aprotic polar solvents: dimethyl sulfoxide, N-methyl-2-pyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide and the like.

These organic solvents may be used alone or in combination of two or more.
In the case of using a mixed solvent, it is preferable to combine two or more of the solvents in the above solvent group, but even if a plurality of the same solvent groups in the above examples are combined, one or more from different solvent groups May be combined. The composition ratio can be determined in consideration of the physical properties of each solvent and the solubility of a polymer compound or the like.

Preferable examples in the case of selecting and combining a plurality of types from the same solvent group include a plurality of types from aromatic hydrocarbon solvents and a plurality of types from aromatic ether solvents.
Preferable examples in the case of selecting and combining one or more types from different solvent groups include the following combinations.
Aromatic hydrocarbon solvents and aliphatic hydrocarbon solvents; aromatic hydrocarbon solvents and aromatic ether solvents; aromatic hydrocarbon solvents and aliphatic ether solvents; aromatic hydrocarbon solvents and aprotic Polar solvent; aromatic ether solvent and aprotic polar solvent.
Moreover, water can also be added to a single solvent or a mixed organic solvent.

  Among these organic solvents, a single solvent or a mixed solvent containing one or more organic solvents having a structure containing a benzene ring, a melting point of 0 ° C. or less, and a boiling point of 100 ° C. or more has a viscosity and film formation. Among these, a single solvent or a mixed solvent containing at least one aromatic hydrocarbon solvent or aromatic ether solvent is particularly 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.

Examples of triplet light-emitting complexes include Ir (ppy) ₃ , Btp ₂ Ir (acac), FIrpic, COM-1, COM-2, COM-3, COM-4, COM-5, COM-, which have iridium as a central metal. 6, COM-7, COM-8, iridium complexes such as ADS066GE commercially available from American Dye Source, platinum complexes such as PtOEP with platinum as the central metal, Eu (TTA) ₃ phen with europium as the central metal, etc. The europium complex is preferred. In addition, these triplet light emission complexes are shown by the following chemical formula.

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

  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 to 10 mg of a measurement sample is dissolved in about 0.5 mL of deuterated chloroform or deuterated tetrahydrofuran, and NMR (Varian, trade name: MERCURY 300, or Bruker, trade name: AVANCE 600 TCI cryoprobe) is prepared. And measured.

<Synthesis Example 1: Synthesis of Compound 1>

  After making the gas in the reaction vessel a nitrogen gas atmosphere, 2,7-dibromocarbazole (37.54 g) was dissolved in dimethyl sulfoxide (75 mL), tetraethylammonium chloride (46.20 g), sodium hydroxide (46.2 g). ) And water (40 mL) were added sequentially. Thereafter, 2-ethylhexyl bromide (55.80 g) was slowly added dropwise and stirred at 90 ° C. for 4.5 hours. After cooling the obtained solution to room temperature, toluene (100 mL) and water (100 mL) were added and liquid-separated. Thereafter, recrystallization using trichloromethane and methanol, silica gel column chromatography (developing solvent: hexane), dissolving in tetrahydrofuran and dropping into methanol, 18 g of compound 1 having a purity of 99.9% was obtained. Obtained. The yield was 36%.

LC-MS (APCI, positive): [M + H] +438
1H-NMR (CDCl ₃ , 600 MHz): δ (ppm) = 0.85 to 0.94 (6H, m), 1.26 to 1.40 (8H, m), 2.00 (1H, m), 4.06 (2H, d), 7.35 (2H, d), 7.50 (2H, s), 7.89 (2H, d).

<Synthesis Example 2: Synthesis of Compound 2>

  After making the gas in the reaction vessel a nitrogen gas atmosphere, 4-tert-butyl-2,6-dimethylaniline (9.57 g) was dissolved in toluene (150 ml), tert-sodium butoxide (5.19 g), Tris (dibenzylideneacetone) dipalladium (0.82 g) and 2-dicyclohexylphosphino-2 ′-(N, N-dimethylamino) biphenyl (1.42 g) were sequentially added. Then, it heated up at 90 degreeC, the compound 1 (7.87g) was added, and it stirred, heating at 105 degreeC for 3 hours. The resulting solution was cooled to room temperature, filtered through celite, washed with toluene, and then the obtained solution was concentrated under reduced pressure. Crystals obtained by adding methanol (150 ml) to the obtained residue to disperse the crystals are collected by filtration, washed with methanol, and dried to obtain 6.5 g of Compound 2 having a purity of 97.6%. Obtained. The yield was 57%.

<Synthesis Example 3: Synthesis of Compound 3>

  After making the gas in the reaction vessel a nitrogen gas atmosphere, Compound 2 (9.0 g) was dissolved in o-xylene (120 ml), tert-sodium butoxide (5.49 g), tris (dibenzylideneacetone) dipalladium. (0.26 g) and diphenylphosphinoferrocene (0.63 g) were sequentially added, and the temperature was raised to 100 ° C. Thereafter, dibromobromobenzene (33.69 g) was added, and the mixture was stirred at 135 ° C. for 4 hours. The resulting solution was cooled to room temperature, filtered through celite, washed with toluene, and then the obtained solution was concentrated under reduced pressure. The obtained residue was separated by silica gel column chromatography (mixture of hexane → toluene / hexane (1/20)). The obtained residue was dissolved in a mixed solution of toluene (100 ml) and hexane (100 ml), activated carbon (10 g) was added, and the mixture was stirred at 60 ° C. for 0.5 hr, filtered and concentrated. The obtained residue was dissolved in a mixed solution of tetrahydrofuran (hereinafter sometimes referred to as “THF”) (40 ml) and methanol (15 ml), then activated carbon (5.5 g) was added, and the mixture was stirred at room temperature for 1 hour. Then filtered and concentrated. The obtained residue was washed with a mixed solution of toluene (5 ml) and methanol (50 ml) and then dried to obtain 5.21 g of Compound 3 having a purity of 99.6%. The yield was 39%.

LC-MS (ESI, positive): [M ⁺ ] 937
¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 0.68 (3H, t), 0.80 (3H, t), 1.05-1.20 (18H, m), 1.32 (8H, s), 1.54 (6H, s), 1.62 (1H, br), 2.02 (6H, s), 3.73 (2H, d), 6.75-6.95 ( 6H, m), 7.05-7.26 (10H, m), 7.70 (2H, m).

<Synthesis Example 4: Synthesis of Compound 4>

  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 4.

<Synthesis Example 5: Synthesis of Compound 5>

  The reaction vessel was placed under an argon gas stream, and compound 4 (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 5 were obtained by wash | cleaning with the obtained residual methanol.

<Synthesis Example 6: Synthesis of Compound 6>

  The reaction vessel was placed in an argon gas stream, and compound 5 (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 6 was obtained by recrystallizing the obtained residue using methanol and butyl acetate.

<Synthesis Example 7: Synthesis of Compound 7>

The reaction vessel was filled with an argon gas atmosphere, and compound 6 (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 7 were obtained by recrystallizing the obtained residue using toluene and methanol.

<Synthesis Example 8: Synthesis of Compound 8>

  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. To the resulting solution was added 2.5M n-butyllithium / hexane solution (1 molar equivalent to 1-bromo-3,5-di-n-hexylbenzene) (176 ml) at -75 ° C for 1.5 hours. The resulting 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 8.

<Synthesis Example 9: Synthesis of Compound 9>

  The inside of the reaction vessel was under an argon gas stream, and Compound 8 (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 9.

<Synthesis Example 10: Synthesis of Compound 10>

  The inside of the reaction vessel was placed in an argon gas stream, and compound 9 (138 g), 1-bromooctane (75.4 ml), methyltrioctylammonium chloride (trade name: Aliquat® 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 compounds 10 were obtained by performing reprecipitation using methanol and a dichloromethane with respect to the obtained residue.

<Synthesis Example 11: Synthesis of Compound 11>

  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 washed with magnesium sulfate. After drying, 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 11 as a pale yellow oil.

MS (ESI, positive): [M ⁺ ] 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 (3H, m), 7.35-7.44 (3H, m), 7.90-7. 95 (3H, m).

<Synthesis Example 12: Synthesis of Compound 12>

  The reaction vessel was filled with a nitrogen gas atmosphere, and then compound 11 (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 12 as a white powder solid.

LC-MS (ESI, positive): [M ⁺ ] 605
¹ H-NMR (300 MHz, CDCl ₃ ): δ (ppm) = 0.85-0.95 (12H, m), 1.24-1.50 (16H, m), 1.6-1.85 ( 2H, m), 2.90-3.18 (4H, m), 7.60 (2H, s), 8.47 (2H, s).

<Example 1: Synthesis of polymer compound 1>

After making the gas in the reaction vessel an inert gas atmosphere, Compound 12 (1.1969 g, 2.00 mmol), Compound 10 (1.0808 g, 1.80 mmol), Compound 3 (0.1894 g, 0.20 mmol), Dichlorobis (orthomethoxyphenylphosphine) palladium (1.8 mg) and toluene (50 mL) were mixed and heated to 105 ° C.
A 20 wt% tetraethylammonium hydroxide aqueous solution (7 mL) was added dropwise to the resulting reaction solution and refluxed for 4.5 hours. Thereafter, phenylboronic acid (24.4 mg) and dichlorobis (orthomethoxyphenylphosphine) palladium (1.8 mg) were added thereto, and the mixture was refluxed for 17 hours. Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 2 hours. The obtained mixture was cooled, then washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation. The precipitate was collected by filtration to obtain a precipitate.
The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol, precipitation occurred. The precipitate was collected by filtration and dried to obtain 1.26 g of polymer compound 1. The number average molecular weight of polystyrene conversion of the high molecular compound 1 was 9.1 * 10 < ⁴ >, and the weight average molecular weight of polystyrene conversion was 2.5 * 10 < ⁵ >.

  The polymer compound 1 has the following formula (J1) as a theoretical value obtained from the charged raw materials:

で示される構成単位と、下記式（Ｊ２）：

And the following formula (J2):

で示される構成単位と、下記式（Ｊ３）：

And the following formula (J3):

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 2: Synthesis of polymer compound 2>

After making the gas in the reaction vessel an inert gas atmosphere, Compound 7 (1.340 g, 2.00 mmol), Compound 10 (1.0808 g, 1.80 mmol), Compound 3 (0.1894 g, 0.2 mmol), Dichlorobis (orthomethoxyphenylphosphine) palladium (1.8 mg) and toluene (50 mL) were mixed and heated to 105 ° C.
A 20 wt% tetraethylammonium hydroxide aqueous solution (7 mL) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. Thereafter, phenylboronic acid (24.4 mg) and dichlorobis (orthomethoxyphenylphosphine) palladium (1.8 mg) were added thereto and refluxed for 16 hours. Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 2 hours. The obtained mixture was cooled, then washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation. The precipitate was collected by filtration to obtain a precipitate.
The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol, precipitation occurred. The precipitate was collected by filtration and dried to obtain 1.12 g of polymer compound 2. The number average molecular weight in terms of polystyrene of the polymer compound 2 was 1.0 × 10 ⁵ , and the weight average molecular weight in terms of polystyrene was 2.5 × 10 ⁵ .

  The polymer compound 2 is represented by the following formula (J4) in terms of theoretical values obtained from the charged raw materials:

で示される構成単位と、下記式（Ｊ２）：

And the following formula (J2):

で示される構成単位と、下記式（Ｊ３）：

And the following formula (J3):

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.

<Synthesis Example 13: Synthesis of Polymer Compound 3>

  After making the gas in the reaction vessel an inert gas atmosphere, the following formula:

で示される化合物Ｉ３（１．８４６９ｇ、２．００ｍｍｏｌ）、下記式：

Compound I3 (1.8469 g, 2.00 mmol) represented by the following formula:

で示される化合物Ｔ１（０．６４３０ｇ、２．００ｍｍｏｌ）、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（５０ｍＬ）を混合し、１０５℃に加熱した。

Embedded image Compound T1 (0.6430 g, 2.00 mmol), dichlorobistriphenylphosphine palladium (1.4 mg) and toluene (50 mL) were mixed and heated to 105 ° C.

A 20 wt% tetraethylammonium hydroxide aqueous solution (7 mL) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. Thereafter, phenylboronic acid (24.4 mg) and dichlorobistriphenylphosphine palladium (1.4 mg) were added thereto and refluxed for 3 hours. Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 16 hours. The obtained mixture was cooled, then washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation. The precipitate was collected by filtration to obtain a precipitate.
The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol, precipitation occurred. The obtained precipitate was collected by filtration and dried to obtain 1.227 g of polymer compound 3. The polymer compound 3 had a polystyrene-equivalent number average molecular weight of 1.1 × 10 ⁵ and a polystyrene-equivalent weight average molecular weight of 2.6 × 10 ⁶ .

  The polymer compound 3 is represented by the following formula (J7) in terms of theoretical values determined from the charged raw materials:

で示される構成単位と、下記式（Ｊ８）：

And the following formula (J8):

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

Is an alternating copolymer formed by a molar ratio of 50:50.

<Synthesis Example 14: Synthesis of Polymer Compound 4>

  After making the gas in the reaction vessel an inert gas atmosphere, the following formula:

で示される化合物Ｉ１（１．５４９ｇ、１．７０ｍｍｏｌ）、下記式：

Compound I1 (1.549 g, 1.70 mmol) represented by the following formula:

で示される化合物Ｉ２（０．１５８ｇ、０．３０ｍｍｏｌ）、化合物Ｉ３（１．８１４ｇ、２．００ｍｍｏｌ）、ジクロロビス（オルトメトキシフェニルホスフィン）パラジウム（１．８ｍｇ）およびトルエン（４０ｍＬ）を混合し、１０５℃に加熱した。
得られた反応液に、２０重量％水酸化テトラエチルアンモニウム水溶液（７ｍＬ）を滴下し、３時間還流させた。その後、そこに、フェニルボロン酸（２４．４ｍｇ）およびジクロロビス（オルトメトキシフェニルホスフィン）パラジウム（１．８ｍｇ）を加え、３時間還流させた。その後、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。得られた混合物を冷却後、水で２回、３重量％酢酸水溶液で２回、水で２回洗浄し、得られた溶液をメタノールに滴下したところ、沈澱が生じた。この沈澱をろ取することで沈殿物を得た。
得られた沈殿物をトルエンに溶解させ、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に滴下したところ、沈殿が生じた。この沈殿をろ取し、乾燥させることにより、高分子化合物４を２．２ｇ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５．４×１０^４であり、ポリスチレン換算の重量平均分子量は３．１×１０^５であった。

Compound I2 (0.158 g, 0.30 mmol), Compound I3 (1.814 g, 2.00 mmol), dichlorobis (orthomethoxyphenylphosphine) palladium (1.8 mg) and toluene (40 mL) represented by Heated to ° C.
A 20 wt% tetraethylammonium hydroxide aqueous solution (7 mL) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours. Thereafter, phenylboronic acid (24.4 mg) and dichlorobis (orthomethoxyphenylphosphine) palladium (1.8 mg) were added thereto and refluxed for 3 hours. Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 2 hours. The obtained mixture was cooled, then washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation. The precipitate was collected by filtration to obtain a precipitate.
The obtained precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol, precipitation occurred. The precipitate was collected by filtration and dried to obtain 2.2 g of polymer compound 4. The polymer compound 2 had a polystyrene-equivalent number average molecular weight of 5.4 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 3.1 × 10 ⁵ .

  The polymer compound 4 has the following formula (J5) as a theoretical value obtained from the charged raw materials:

で示される構成単位と、下記式（Ｊ６）：

And the following formula (J6):

で示される構成単位と、下記式（Ｊ７）：

And the following formula (J7):

で示される構成単位とが、４２．５：７．５：５０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 42.5: 7.5: 50.

<Example D1: Production and evaluation of light-emitting element D1>
A hole injection layer with a thickness of 35 nm is formed on a glass substrate with an ITO film having a thickness of 45 nm by sputtering using spin coating using Plexcore AQ-1200 (manufactured by Plextronics), which is a hole injection agent. A film was formed and dried by heating at 170 ° C. for 15 minutes on a hot plate in an air atmosphere.
Next, the polymer compound 4 was dissolved in xylene (solvent) to prepare a 0.7% by mass xylene solution. By spin coating on the hole injection layer using this xylene solution, a hole transport layer was formed to a thickness of 20 nm and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere. .
Next, the high molecular compound 1 was dissolved in chlorobenzene (solvent), and 0.9 mass% chlorobenzene solution A was prepared. Using this chlorobenzene solution A, a light emitting layer was formed to a thickness of 60 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.
When voltage was applied to the light-emitting element D1 obtained above, EL light emission having a peak at 455 nm was obtained from this element, and the maximum light-emitting efficiency was 7.6 cd / A. The current value was set so that the initial luminance of the light emitting element D1 was 5000 cd / m ² , the device was then driven at a constant current, and the change in luminance with time was measured. As a result, the luminance was reduced by half after 84 hours. The results are shown in Table 1.

<Example D2: Production and Evaluation of Light-Emitting Element D2>
Polymer compound 3 was dissolved in chlorobenzene (solvent) to prepare 0.9 mass% chlorobenzene solution B. Next, the chlorobenzene solution A used in Example D1 and the chlorobenzene solution B were mixed so that the solid content ratio of the polymer compound 1 and the polymer compound 3 was 90:10 to prepare the chlorobenzene solution C. .
A light emitting device D2 was produced in the same manner as in Example D1, except that this chlorobenzene solution C was used instead of the chlorobenzene solution A in Example D1.
When voltage was applied to the light-emitting element D2 obtained above, EL light emission having a peak at 455 nm was obtained from this element, and the maximum light-emitting efficiency was 8.6 cd / A. The current value was set so that the initial luminance of the light-emitting element D2 was 5000 cd / m ² , the device was then driven at a constant current, and the change in luminance with time was measured. As a result, the luminance was reduced by half after 207 hours. The results are shown in Table 1.

<Example D3: Light emitting element D3>
Polymer compound 2 was dissolved in chlorobenzene (solvent) to prepare 0.9 wt% chlorobenzene solution D.
A light emitting device D3 was produced in the same manner as in Example D1, except that this chlorobenzene solution D was used instead of the chlorobenzene solution A in Example D1.
When voltage was applied to the light-emitting element D3 obtained above, EL light emission having a peak at 450 nm was obtained from this element, and the maximum light-emitting efficiency was 6.7 cd / A. A current value was set so that the initial luminance of the light-emitting element D3 was 5000 cd / m ² , the device was then driven at a constant current, and a change in luminance with time was measured. As a result, the luminance was reduced by half after 48 hours. The results are shown in Table 1.

<Example D4: Light-emitting element D4>
A hole injection layer with a thickness of 65 nm is formed on a glass substrate with an ITO film having a thickness of 45 nm by sputtering using spin coating using Plexcore AQ-1200 (manufactured by Plextronics), which is a hole injection agent. A film was formed and dried by heating at 170 ° C. for 15 minutes on a hot plate in an air atmosphere.
Next, the polymer compound 4 was dissolved in xylene (solvent) to prepare a 0.7% by mass xylene solution. By spin coating on the hole injection layer using this xylene solution, a hole transport layer was formed to a thickness of 20 nm and heated on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere. .
Next, the light emitting material P shown below:

をクロロベンゼンに溶解させ、０．９質量％のクロロベンゼン溶液Ｅを調製した。次に、実施例Ｄ３で使用したクロロベンゼン溶液Ｄと、このクロロベンゼン溶液Ｅを、高分子化合物２と発光材料Ｐとの固形分比が９２．５：７．５となるように混合し、クロロベンゼン溶液Ｆを調整した。
このクロロベンゼン溶液Ｆを用いて、正孔輸送層上にスピンコートすることにより、発光層を８０ｎｍの厚さで成膜し、窒素ガス雰囲気中において、ホットプレート上で１５０℃、１０分加熱した。
次に、発光層上に、陰極としてフッ化ナトリウムを５ｎｍ、次いでアルミニウムを１２０ｎｍ蒸着して、発光素子Ｄ４を作製した。なお、真空度が、１×１０^−４Ｐａ以下に到達した後に金属の蒸着を開始した。
上記で得られた発光素子Ｄ４に電圧を印加したところ、この素子から６２５ｎｍにピークを有するＥＬ発光が得られ、最大発光効率は８．８ｃｄ／Ａであった。発光素子Ｄ４に対して、初期輝度が１００００ｃｄ／ｍ^２となるように電流値を設定後、定電流で駆動させ、輝度の時間変化を測定した。その結果、輝度は４１０時間後に半減した。結果を表１に示す。

Was dissolved in chlorobenzene to prepare 0.9 mass% chlorobenzene solution E. Next, the chlorobenzene solution D used in Example D3 and the chlorobenzene solution E were mixed so that the solid content ratio of the polymer compound 2 and the luminescent material P was 92.5: 7.5, and the chlorobenzene solution F was adjusted.
Using this chlorobenzene solution F, a light emitting layer was formed to a thickness of 80 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, thereby manufacturing a light-emitting element D4. In addition, after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, metal deposition was started.
When voltage was applied to the light-emitting element D4 obtained above, EL light emission having a peak at 625 nm was obtained from this element, and the maximum light-emitting efficiency was 8.8 cd / A. A current value was set so that the initial luminance of the light-emitting element D4 was 10,000 cd / m ² , the device was then driven at a constant current, and a change in luminance with time was measured. As a result, the luminance was reduced by half after 410 hours. The results are shown in Table 1.

Claims (16)

A structural unit represented by the following formula (1);
A polymer comprising a structural unit represented by the following formula (2), a structural unit represented by the following formula (3), and one or more structural units selected from the group consisting of the structural unit represented by the following formula (4): Compound.

[Where:
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
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 ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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 ⁷ 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 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. ]

[Where:
a and b 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. When a plurality of R ⁸ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. When a plurality of R ⁹ are present, they may be the same or different, and may be bonded together to form a ring structure together with the carbon atoms to which they are bonded.
R ¹⁰ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted alkoxy group.
R ¹¹ 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 ¹² , R ¹³ , R ¹⁴ and R ¹⁵ 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 ¹⁶ and R ¹⁷ 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. When a plurality of R ¹⁶ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. When a plurality of R ¹⁷ are present, they may be the same or different and may be bonded together to form a ring structure together with the carbon atoms to which they are bonded.
R ¹² and R ¹⁴ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹³ and R ¹⁵ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹² and R ¹³ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ¹⁴ and R ¹⁵ are connected to each other to bond to each other. A ring structure may be formed together with the atoms. ]

[Where
R ¹⁸ and R ¹⁹ 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. However, at least one of R ¹⁸ and R ¹⁹ represents a group other than a hydrogen atom. ] The polymer compound according to claim 1, wherein Ar ¹ and Ar ² are unsubstituted or substituted arylene groups. The polymer compound according to claim 1, wherein R ^A and R ^B are an unsubstituted or substituted aryl group. Furthermore, the high molecular compound as described in any one of Claims 1-3 containing the structural unit shown by following formula (5).

[Where:
Ar ³ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
However, the structural unit represented by Formula (5) is different from the structural unit represented by Formula (2), the structural unit represented by Formula (3), and the structural unit represented by Formula (4). ]   The polymer compound according to claim 4, wherein the structural unit represented by the formula (5) is an unsubstituted or substituted fluorenediyl group. Furthermore, the high molecular compound as described in any one of Claims 1-5 containing the structural unit shown by following formula (6).

[Where:
p shows the integer of 0-3. q represents 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 the same or selected from the group consisting of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an arylene group and a divalent heterocyclic group; A divalent group in which two or more different groups are linked (the divalent group may have a substituent).
R ²⁵ , R ²⁶ and R ²⁷ 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.
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.
However, the structural unit represented by the formula (6) is different from the structural unit represented by the formula (1). ] The polymer compound according to claim 6, wherein the structural unit represented by the formula (6) is a structural unit represented by the following formula (7).

[Where:
R ²⁸ 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 ²⁹ ) ₂ —. R ²⁹ represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ²⁹ may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. ] A structural unit represented by the formula (1);
A polymer compound comprising a structural unit represented by the following formula (8) and / or a structural unit represented by the following formula (8 ′).

[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 an integer of 1 or 2.
Ar ⁸ represents an unsubstituted or substituted (2 + n) -valent aromatic heterocyclic group or an unsubstituted or substituted (2 + n) -valent 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 two or more X exists, they may be the same or different.
However, the structural unit represented by the formula (8) includes the structural unit represented by the formula (2), the structural unit represented by the formula (3), the structural unit represented by the formula (4), and the formula (5). ). ]

[Where:
c ′ represents 0 or 1.
Ar ²⁰ and Ar ⁴⁰ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ³⁰ is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or two or more identical or different groups selected from the group consisting of an arylene group and a divalent heterocyclic group are linked A divalent group (the divalent group may have a substituent).
X represents the same meaning as described above.
X ′ represents a monovalent crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
However, the structural unit represented by the formula (8 ′) is different from the structural unit represented by the formula (1) and the structural unit represented by the formula (6). ] A polymer compound comprising a structural unit represented by the formula (1) and a structural unit represented by the following formula (9).

[Where:
a1 and a2 each independently represent an integer of 0 to 4, and a3 represents an integer of 0 to 5.
R ³⁰ , R ³¹ and R ³² 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, A substituted monovalent heterocyclic group is shown. When a plurality of R ³⁰ are present, they may be the same or different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded. If there are a plurality of R ³¹ , they are the same. However, they may be different, and may be bonded to each other to form a ring structure together with the carbon atoms to which they are bonded, and when there are a plurality of R ³² , they may be the same or different and A ring structure may be formed together with the carbon atom to which each is bonded. ]   The polymer according to any one of claims 1 to 9, wherein a proportion of the structural unit represented by the formula (1) with respect to all structural units contained in the polymer compound is 0.1 to 70 mol%. Compound. The polymer compound according to any one of claims 1 to 10,
One or more materials selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.   The composition according to claim 11, wherein the luminescent material is a triplet luminescent complex.   The organic thin film containing the high molecular compound as described in any one of Claims 1-10.   The organic thin film containing the composition of Claim 11 or 12.   A light emitting element provided with the organic thin film of Claim 13 or 14. A compound represented by the following formula (1M).

[Where:
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
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 ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ 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 ⁷ 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 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.
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).
<Substituent group A>
Chlorine atom, bromine atom, iodine atom,
A group represented by —O—S (═O) ₂ R ³³ (R ³³ represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group).
<Substituent group B>
A group represented by -B (OR ³⁴ ) ₂ (R ³⁴ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ³⁴ may be the same or different from each other);
A group represented by -BF ₃ 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 ³⁵ ) ₃ (R ³⁵ represents a hydrogen atom or an unsubstituted or substituted alkyl group, and a plurality of R ^{35 s} may be the same or different from each other, and are linked to each other to bind to each other. And may form a ring structure together with). ]