JP6078998B2 - Polymer compound and light emitting device using the same - Google Patents

Description

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

  As a hole transport material for use in a light-emitting element, for example, a polymer compound including the following structural unit derived from arylamine and the following structural unit derived from fluorene having a benzocyclobutane structure (Patent Document 1) ) Is being considered.

JP 2008-106241 A

  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, an insolubilized organic thin film and a light emitting device containing the polymer compound.

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

［式中、
Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８、Ｒ^９およびＲ^１０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^１とＲ^３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^２とＲ^４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^１とＲ^２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^３とＲ^４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^７、Ｒ^８およびＲ^９のうち隣接する基同士は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。
Ｒ^ＡおよびＲ^Bは、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ａｒ^１およびＡｒ^２は、それぞれ独立に、非置換もしくは置換のアリーレン基または非置換もしくは置換の２価の複素環基を示す。
Ａｒ^１とＲ^Ａは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよく、Ａｒ^２とＲ^Bは互いに連結して、それぞれが結合する窒素原子とともに環構造を形成していてもよい。
Xは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Yは、−C（Ｒ^a）₂-、−C（Ｒ^a）₂-C（Ｒ^a）₂-、−N（Ｒ^a）-、−P（Ｒ^a）−、−O−、−Ｓ−または−O-C（Ｒ^a）₂-を示す。
Ｒ^aは、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアルコキシ基、非置換もしくは置換のアリール基、非置換もしくは置換のアリールオキシ基または非置換もしくは置換の１価の複素環基を示す。Ｒ^aが複数存在する場合、それらは同一でも異なっていてもよく、互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。］

［式中、
ｎａは０〜３の整数を示し、ｎｂは０〜１２の整数を示し、ｎＡは０または１であり、ｎは１または２を示す。
Ａｒ^３は、非置換もしくは置換の（２＋ｎ）価の芳香族炭化水素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、それらは同一でも異なっていてもよい。Ｌ^ｂが複数存在する場合、それらは同一でも異なっていてもよい。
Ｌ^Ａは、酸素原子または硫黄原子を示す。Ｌ^Ａが複数存在する場合、それらは同一でも異なっていてもよい。
Ｘ’は、１価の架橋性基を示す。Ｘ’が複数存在する場合、それらは同一でも異なっていてもよい。］

［式中、
ｃは０または１を示し、
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。
Ａｒ^２０、Ａｒ^３０およびＡｒ^４０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。
Ｘ’は、前記と同義である。
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（２’）で示される構成単位は、式（１）で示される構成単位とは異なる。］
［２］ 前記式（１−１）で示される構成単位、前記式（１−２）で示される構成単位および前記式（１−３）で示される構成単位が、それぞれ、下記式（１−１−Ａ）で示される構成単位、下記式（１−２−Ａ）で示される構成単位および下記式（１−３−Ａ）で示される構成単位である、［１］に記載の高分子化合物。

［式中、
X、Y、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８、Ｒ^９、Ｒ^１０、Ｒ^Ａ、Ｒ^Ｂ、Ａｒ^１およびＡｒ^２は、前記と同義である。
ｎ^１およびｎ^２は、それぞれ独立に、１〜５の整数を示す。
Ｒ^１１、Ｒ^１２、Ｒ^１３およびＲ^１４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^１１、Ｒ^１２、Ｒ^１３およびＲ^１４がそれぞれ複数存在する場合、それらはそれぞれ同一でも異なっていてもよく、Ｒ^１１、Ｒ^１２、Ｒ^１３およびＲ^１４のうち隣接する基同士は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。］
［３］ 前記式（１−１−Ａ）で示される構成単位が、下記式（１−１−Ｂ）で示される構成単位である、［２］に記載の高分子化合物。

［式中、
ｎ^１、ｎ^２、Ｒ^５、Ｒ^６、Ｒ^７、Ｒ^８、Ｒ^９、Ｒ^１０、Ｒ^１１、Ｒ^１２、Ｒ^１３、Ｒ^１４、Ｒ^Ａ、Ｒ^Ｂ、Ａｒ^１およびＡｒ^２は、前記と同義である。
Ｒ^１５およびＲ^１６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^１５とＲ^１６は互いに連結して、それぞれが結合する炭素原子とともに環構造を形成していてもよい。］
［４］ 前記Ｘ’が、下記式（Ｘ’−１）で示される１価の架橋性基である、［１］〜［３］のいずれか一項に記載の高分子化合物。

［式中、ベンゾシクロブタンは置換基を有していてもよい。］
［５］ 前記Ｘ’が、下記式（Ｘ’−２）で示される１価の架橋性基である、［１］〜［４］のいずれか一項に記載の高分子化合物。

［式中、
ｎｅおよびｎｆは、それぞれ独立に、０または１を示す。
Ｌ^Ｘ１は、酸素原子、硫黄原子、カルボニル基または−Ｏ−ＣＯ−で表される基を示す。
Ｒ^１７、Ｒ^１８、Ｒ^１９、Ｒ^２０およびＲ^２１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、非置換もしくは置換の１価の複素環基、ハロゲン原子、シアノ基またはニトロ基を示す。
なお、波線の存在する二重結合は、Ｅ体、Ｚ体、またはＥ体およびＺ体の混合物のいずれでもよいことを意味する。］
［６］ 更に、下記式（３）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、
Ａｒ^４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（３）で示される構成単位は、前記式（２）で示される構成単位とは異なる。］
［７］ 前記式（３）で示される構成単位の少なくとも１個が、非置換もしくは置換のフェニレンジイル基からなる構成単位である、［６］に記載の高分子化合物。
［８］ 前記式（３）で示される構成単位の少なくとも１個が、非置換もしくは置換のフルオレンジイル基からなる構成単位である、［７］に記載の高分子化合物。
［９］ 更に、下記式（４）で示される構成単位を含む、［１］〜［８］のいずれか一項に記載の高分子化合物

［式中、
a^１およびa^２は、それぞれ独立に、０または１を示す。
Ａｒ^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または非置換もしくは置換の２価の複素環基を示す。
Ａｒ^６およびＡｒ^８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^C、Ｒ^DおよびＲ^Eは、それぞれ独立に、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ａｒ^５、Ａｒ^６、Ａｒ^７およびＡｒ^８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（４）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（２’）で示される構成単位とは異なる。］
［１０］ 前記式（４）で示される構成単位の少なくとも１個が、下記式（５）で示される構成単位である、［９］に記載の高分子化合物。

［式中、
Ｒ^Fは、水素原子、非置換もしくは置換のアルキル基、非置換もしくは置換のアリール基または非置換もしくは置換の１価の複素環基を示す。
Ｚは、単結合、酸素原子、硫黄原子または−Ｃ（Ｒ^b）_２−を示す。Ｒ^bは、水素原子、非置換もしくは置換のアルキル基または非置換もしくは置換のアリール基を示す。２個存在するＲ^ｂは、同一でも異なっていてもよく、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。］
［１１］ 前記式（１−１）で示される構成単位、前記式（１−２）で示される構成単位および前記式（１−３）で示される構成単位の合計含有量が、高分子化合物に含まれる構成単位の合計含有量に対して、２０〜６０モル％である、［１］〜［１１］のいずれか一項に記載の高分子化合物。
［１２］ ［１］〜［１１］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少なくとも一種の材料と、を含有する組成物。
［１３］ ［１］〜［１１］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］ ［１３］に記載の高分子化合物を含有する有機薄膜を、加熱することで不溶化させた、不溶化有機薄膜。
［１５］ ［１３］に記載の有機薄膜または［１４］に記載の不溶化有機薄膜を備える発光素子。 [1] At least one selected from the group consisting of a structural unit represented by the following formula (1-1), a structural unit represented by the following formula (1-2), and a structural unit represented by the following formula (1-3) A structural unit of
A polymer compound comprising a structural unit represented by the following formula (2) and / or a structural unit represented by the following formula (2 ′).

[Where:
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, unsubstituted or substituted An alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group.
R ¹ and R ³ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ² and R ⁴ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹ and R ² may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ³ and R ⁴ are connected to each other to bond to each other. A ring structure may be formed together with atoms, and adjacent groups among R ⁷ , R ⁸ and R ⁹ may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —, —P (R ^a ) —, —O—, —S. -Or -OC (R ^a ) ₂ -is shown.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]

[Where:
na represents an integer of 0 to 3, nb represents an integer of 0 to 12, nA represents 0 or 1, and n represents 1 or 2.
Ar ³ represents an unsubstituted or substituted (2 + n) -valent aromatic hydrocarbon 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 a plurality of X ′ are present, they may be the same or different. ]

[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).
Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ 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.
X ′ has 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 (2 ′) is different from the structural unit represented by the formula (1). ]
[2] The structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3) are each represented by the following formula (1- The polymer according to [1], which is a structural unit represented by 1-A), a structural unit represented by the following formula (1-2-A), and a structural unit represented by the following formula (1-3-A) Compound.

[Where:
X, Y, R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.
n ¹ and ^{n 2} each independently represent an integer of 1 to 5.
R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown.
When there are a plurality of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ , they may be the same or different, and adjacent groups of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are linked to each other. And may form a ring structure together with the carbon atoms to which they are bonded. ]
[3] The polymer compound according to [2], wherein the structural unit represented by the formula (1-1-A) is a structural unit represented by the following formula (1-1-B).

[Where:
n ¹ , n ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ^A , R ^B , Ar ¹ and Ar ² are It is synonymous with.
R ¹⁵ and R ¹⁶ each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or A substituted monovalent heterocyclic group is shown.
R ¹⁵ and R ¹⁶ may be connected to each other to form a ring structure together with the carbon atom to which each is bonded. ]
[4] The polymer compound according to any one of [1] to [3], wherein X ′ is a monovalent crosslinkable group represented by the following formula (X′-1).

[Wherein, benzocyclobutane may have a substituent. ]
[5] The polymer compound according to any one of [1] to [4], wherein X ′ is a monovalent crosslinkable group represented by the following formula (X′-2).

[Where:
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 ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ and R ²¹ 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. ]
[6] The polymer compound according to any one of [1] to [5], further including a structural unit represented by the following formula (3).

[Where:
Ar ⁴ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
However, the structural unit represented by the formula (3) is different from the structural unit represented by the formula (2). ]
[7] The polymer compound according to [6], wherein at least one of the structural units represented by the formula (3) is a structural unit composed of an unsubstituted or substituted phenylenediyl group.
[8] The polymer compound according to [7], wherein at least one of the structural units represented by the formula (3) is a structural unit composed of an unsubstituted or substituted fluorenediyl group.
[9] The polymer compound according to any one of [1] to [8], further comprising a structural unit represented by the following formula (4):

[Where:
a ¹ and a ² each independently represent 0 or 1.
Ar ⁵ and Ar ⁷ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ⁶ and Ar ⁸ 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 ^C , R ^D and R ^E each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ 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 (4) is different from the structural unit represented by the formula (1) and the structural unit represented by the formula (2 ′). ]
[10] The polymer compound according to [9], wherein at least one of the structural units represented by the formula (4) is a structural unit represented by the following formula (5).

[Where:
R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^{b s} may be the same or different, and may form a ring structure together with the carbon atom to which each R ^b is bonded. ]
[11] The polymer compound has a total content of the structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3). The polymer compound according to any one of [1] to [11], which is 20 to 60 mol% with respect to a total content of the structural units contained in.
[12] The polymer compound according to any one of [1] to [11],
A composition containing at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.
[13] An organic thin film containing the polymer compound according to any one of [1] to [11].
[14] An insolubilized organic thin film in which the organic thin film containing the polymer compound according to [13] is insolubilized by heating.
[15] A light emitting device comprising the organic thin film according to [13] or the insolubilized organic thin film according to [14].

  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 device containing 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 ring formed from a heterocyclic compound (preferably an aromatic heterocyclic compound having aromaticity). Means a remaining atomic group excluding n hydrogen atoms directly bonded to the carbon atom, and includes 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.
The “n-valent aromatic hydrocarbon group” (n is an integer of 1 or more) means the remaining atoms excluding n hydrogen atoms directly bonded to the carbon atoms constituting the ring from the aromatic hydrocarbon. This means a group and includes a group having a condensed ring. In addition, a group in which two or more rings selected from the group consisting of independent benzene rings and condensed rings are directly bonded is not included.
The “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon, 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 remaining after 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.

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

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

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

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

  Among the structural units represented by the formulas (1-1) to (1-3), when the polymer compound of the present embodiment is used for the production of a light emitting device, the obtained luminance life is more excellent. The structural unit represented by (1-1) is preferred.

In formulas (1-1) to (1-3), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ 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 ¹ , R ² , R ^3, and R ⁴ are each a hydrogen atom, unsubstituted or substituted, because when the polymer compound of this embodiment is used for the production of a light-emitting device, the resulting light-emitting device has a better luminance life. Are preferably an alkyl group or an unsubstituted or substituted alkoxy group.

R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ^9, and R ¹⁰ are hydrogen atoms because when the polymer compound of this embodiment is used for manufacturing a light-emitting device, the resulting light-emitting device has a higher luminance life. An atom, an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group is preferred, a hydrogen atom or an unsubstituted or substituted alkyl group is more preferred, and a hydrogen atom is more preferred.

The unsubstituted or substituted alkyl group represented by R ^{1 to} R ¹⁰ 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 and cyclic alkyl group does not include the number of carbon atoms of the substituent, and is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.
Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isoamyl group, n-hexyl group, cyclohexyl group, Examples include n-heptyl group, cyclohexylmethyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, and 2-n-hexyl-decyl group.

The number of carbon atoms of the unsubstituted or substituted aryl group represented by R ^{1 to} R ¹⁰ does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 48, more preferably 6 to 30. .
As the aryl group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, Examples include 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, and 4-phenylphenyl group.

The number of carbon atoms of the unsubstituted or substituted monovalent heterocyclic group represented by R ^{1 to} R ¹⁰ does not include the number of carbon atoms of the substituent, and is usually 2 to 60, preferably 3 to 20.
Examples of the monovalent heterocyclic group include thienyl group, pyrrolyl group, furyl group, pyridyl group, piperidyl group, quinolyl group, isoquinolyl group, pyrimidyl group, triazinyl group, and a hydrogen atom in these groups is an alkyl group, Examples thereof include a group substituted with an alkoxy group or the like. Of these, a thienyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, a pyrimidyl group, and a triazinyl group are preferable.

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

The number of carbon atoms of the unsubstituted or substituted aryloxy group represented by R ^{1 to} R ¹⁰ 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.

In formulas (1-1) to (1-3), R ^A and R ^B are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted group. A monovalent heterocyclic group is shown.

R ^A and R ^B are excellent in stability of the polymer compound of the present embodiment, and when the polymer compound is used in the production of a light emitting device, the obtained luminance life is more excellent. A substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group is preferable, and an unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent heterocyclic group is preferred. More preferably, it is an unsubstituted or substituted aryl group.

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group and the unsubstituted or substituted monovalent heterocyclic group represented by R ^A and R ^B are respectively represented by R ^{1 to} R ¹⁰ . The definition and examples of the unsubstituted or substituted alkyl group, unsubstituted or substituted aryl group and unsubstituted or substituted monovalent heterocyclic group are the same as those described above.

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

In Formula (1-1) to Formula (1-3), Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ¹ and Ar ² does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 30, and more preferably 6 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. 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, 1,4-phenylene group, 2,7-fluorenediyl group , 2,6 anthracenediyl group, 9,10-anthracene-diyl group, 2,7-phenanthrenediyl group, 2,7-dihydro-phenanthrenediyl group, 1,6-pyrenediyl group.

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

The groups represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ^A , R ^B , Ar ¹ and Ar ² have a substituent. You may do it. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. Examples thereof include a cyclic group and a cyano group, and an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferred.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group, unsubstituted or substituted monovalent represented by R ^{1 to} R ¹⁰ , respectively. This is the same as the definition and example of the heterocyclic group of.

R ¹ and R ³ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ² and R ⁴ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹ and R ² may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ³ and R ⁴ are connected to each other to bond to each other. A ring structure may be formed together with atoms, and adjacent groups among R ⁷ , R ⁸ and R ⁹ may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.

“R ⁷ , R ^8, and R ⁹ , which are adjacent to each other, may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded.” It means that they may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ⁷ and R ⁸ are connected to form a ring structure with the carbon atoms to which they are bonded. It means that R ⁸ and R ⁹ 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, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or Examples thereof include a substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group and unsubstituted or substituted monovalent represented by R ^{1 to} R ¹⁰ , respectively. This is the same as the definition and example of the heterocyclic group of.

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

Definitions 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 group and the unsubstituted or substituted aryl group represented by R ^{1 to} R ¹⁰ , respectively. The same as the definitions and examples.

The formed ring structure may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or Examples thereof include a substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group and unsubstituted or substituted monovalent represented by R ^{1 to} R ¹⁰ , respectively. This is the same as the definition and example of the heterocyclic group of.

In formulas (1-1) to (1-3), X represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —. , -P (R ^a )-, -O-, -S- or -OC (R ^a ) _2- .
In formulas (1-1) to (1-3), Y represents —C (R ^a ) ₂ —, —C (R ^a ) ₂ —C (R ^a ) ₂ —, —N (R ^a ) —. , -P (R ^a )-, -O-, -S- or -OC (R ^a ) _2- .
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.

R ^a is, stability becomes favorable of the polymer compound of the present embodiment, and, in the case of using the polymer compound in the manufacture of the light emitting device, since the resulting luminescence life more excellent hydrogen atom, an unsubstituted or A substituted alkyl group, an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted aryl group is preferable, and a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group is more preferable. .

Of the unsubstituted or substituted alkyl group, the unsubstituted or substituted alkoxy group, the unsubstituted or substituted aryl group, the unsubstituted or substituted aryloxy group and the unsubstituted or substituted monovalent heterocyclic group represented by R ^a Definitions and examples are each an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group and an unsubstituted group represented by R ^{1 to} R ^10. Or it is the same as the definition and example of a substituted monovalent heterocyclic group.

  The total content of the structural unit represented by formula (1-1), the structural unit represented by formula (1-2), and the structural unit represented by formula (1-3) is the stability of the polymer compound of the present embodiment. Therefore, it is preferably 20 to 60 mol%, more preferably 25 to 55 mol%, more preferably 30 to 50 mol%, based on the total content of the structural units contained in the polymer compound. More preferably it is.

  The structural unit represented by the formula (1-1), the structural unit represented by the formula (1-2), and the structural unit represented by the formula (1-3) When used for production, the luminance lifetime obtained is superior, so the structural unit represented by the formula (1-1-A), the structural unit represented by the formula (1-2-A), and the formula (1-3- A structural unit represented by A) is preferred, a structural unit represented by formula (1-1-A) is more preferred, and a structural unit represented by formula (1-1-B) is preferred. Further preferred.

In formula (1-1-A) to formula (1-3-A), X, Y, R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ^A , R ^B , Ar ¹ and Ar ² has the same meaning as described above.

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

In formulas (1-1-A) to (1-3-A), R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, unsubstituted or A substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group is shown.

When there are a plurality of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ , they may be the same or different, and adjacent groups of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are linked to each other. And may form a ring structure together with the carbon atoms to which they are bonded.

R ¹¹ , R ¹² , R ^13, and R ¹⁴ are hydrogen atoms, unsubstituted or substituted, because when the polymer compound of this embodiment is used for manufacturing a light-emitting device, the resulting light-emitting device has a higher luminance life. Are preferably an alkyl group or an unsubstituted or substituted aryl group, more preferably a hydrogen atom or an unsubstituted or substituted alkyl group.

Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group and unsubstituted or substituted represented by R ¹¹ , R ¹² , R ¹³ and R ¹⁴ The definition and examples of the monovalent heterocyclic group of R ^{1 to} R ¹⁰ are each an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted group represented by R ^{1 to} R ^10. The definition and examples of the aryloxy group and the unsubstituted or substituted monovalent heterocyclic group are the same.

In Formula (1-1-A), Formula (1-2-A) and Formula (1-3-A), when n ¹ is an integer of 2 to 5, a plurality of R ¹¹ are the same or different from each other. A plurality of R ¹² may be the same as or different from each other. In Formula (1-1-A), Formula (1-2-A), and Formula (1-3-A), when n ² is an integer of ² to 5, a plurality of R ¹³ are the same as each other. However, they may be different, and a plurality of R ¹⁴ may be the same or different. Moreover, adjacent groups among R ¹¹ , R ¹² , R ¹³ and R ¹⁴ may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.

In the structural unit represented by the formula (1-1-A), the structural unit represented by the formula (1-2-A), and the structural unit represented by the formula (1-3-A), for example, n ¹ and / or Alternatively, stereoisomerism can occur when n ² is 2 or more and when it has a substituent, when R ¹¹ and R ¹² are different from each other, or when R ¹³ and R ¹⁴ are different from each other. The polymer compound is the same as the structural unit represented by the formula (1-1-A), the structural unit represented by the formula (1-2-A), and the structural unit represented by the formula (1-3-A). You may have only the structural unit which has stereoisomerism, and may have the some structural unit which has mutually different stereoisomerism. Examples of stereoisomerism include diastereomers and enantiomers.

When the structural unit represented by the formula (1-1-A) includes, for example, a skeleton portion represented by the following formula (1-1-Z), examples of the stereoisomerism thereof are represented by the following formula (1-1 -A), Formula (1-1-b), Formula (1-1-c), and Formula (1-1-d). In the following formulae, R ^m and R ⁿ each independently represents an alkyl group.

  A skeleton moiety represented by formula (1-1-a), a skeleton moiety represented by formula (1-1-b), a skeleton moiety represented by formula (1-1-c), and a formula (1-1-d) Are in a diastereomeric relationship with each other.

In the formula (1-1-A), the formula (1-2-A) and the formula (1-3-A), “adjacent groups of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are connected to each other. And each of them may form a ring structure together with the carbon atoms to which they are bonded. ”Means that, for example, groups bonded to the same carbon atom among R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are linked together. To form a ring structure, and when n ¹ and / or n ² is 2 or more, groups bonded to adjacent carbon atoms are connected to each other, and the ring structure together with the carbon atoms to which they are bonded Means that it may be formed.

The formed ring structure may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted Examples thereof include an aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups represented by R ^{1 to} R ¹⁰ , respectively. Is the same.

In formula (1-1-A), formula (1-2-A), and formula (1-3-A), the luminance lifetime obtained when the polymer compound of this embodiment is used for the production of a light-emitting device. N ¹ , n ² , n ³ and n ⁴ are preferably integers of 3 to 5, more preferably 3 or 4, and still more preferably 3.

In the formula (1-1-A), the formula (1-2-A), and the formula (1-3-A), n ¹ and n ² may be the same as or different from each other. In order to facilitate the production of the compound, n ¹ and n ² are preferably the same as each other.

In formula (1-1-B), n ¹ , n ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ^A , R ^{B 1} , Ar ¹ and Ar ² are as defined above.

In formula (1-1-B), R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, or unsubstituted Or a substituted aryloxy group or an unsubstituted or substituted heterocyclic group;

In formula (1-1-B), R ¹⁵ and R ¹⁶ may be linked to each other to form a ring structure together with the carbon atoms to which they are bonded.

Since R ¹⁵ and R ¹⁶ are easy to produce the polymer compound of the present embodiment, and when the polymer compound is used in the production of a light-emitting device, the luminance life of the obtained light-emitting device is more excellent. An atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group or an unsubstituted or substituted aryl group is preferred, and a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group More preferably, it is an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group.

The unsubstituted or substituted alkyl group represented by R ¹⁵ and R ¹⁶ may be linear, branched or cyclic, and the linear alkyl group usually has 1 to 50 carbon atoms, preferably Is 1-30, more preferably 1-20. The number of carbon atoms of the branched and cyclic alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20.
Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isoamyl group, n-hexyl group, cyclohexyl group, n- Heptyl group, cyclohexylmethyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2-n-hexyl-decyl group, and these groups In which a hydrogen atom is substituted with an alkyl group, an aryl group, an alkoxy group, a fluorine atom, or the like.
Since the luminance life when the polymer compound of this embodiment is used in the production of a light emitting device is more excellent, an unsubstituted alkyl group is preferable, and a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an isobutyl group. N-pentyl group, isoamyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n-decyl group, 3,7-dimethyloctyl group, 2-ethyloctyl group, 2- n-hexyl-decyl group is more preferable, methyl group, n-butyl group, isobutyl group, n-pentyl group, isoamyl group, n-hexyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group, n A -decyl group, a 3,7-dimethyloctyl group, a 2-ethyloctyl group, and a 2-n-hexyl-decyl group are more preferable.

The number of carbon atoms of the unsubstituted or substituted aryl group represented by R ¹⁵ and R ¹⁶ does not include the number of carbon atoms of the substituent, and is usually 6 to 60, preferably 6 to 48, more preferably 6 ~ 30.
As the aryl group, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and the hydrogen atom in these groups is an alkyl group, aryl group, alkoxy group And a group substituted with a fluorine atom, etc., and the solubility of the polymer compound of this embodiment in an organic solvent and the heat resistance are improved in a well-balanced manner, so that a phenyl group (particularly, a phenyl substituted with an alkyl group) Group).

Examples of the phenyl group substituted with an alkyl group represented by R ¹⁵ and R ¹⁶ include a 2,6-dimethyl-4-n-butylphenyl group, a 2,6-dimethyl-4-tert-butylphenyl group, 2 -Methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-n-butylphenyl group, 4-n-butylphenyl group, 4-tert-butylphenyl group, 3-n-hexylphenyl group, 4 -N-hexylphenyl group, 3-n-octylphenyl group, 4-n-octylphenyl group, 3,5-dimethylphenyl group, 3-n-hexyl-5-methylphenyl group, 3,5-di-n -Butylphenyl group, 3,5-di-tert-butylphenyl group, 3,5-di-n-hexylphenyl group, 3-n-hexylphenyl group, 4-n-hexyl Phenyl group, 3-n-hexyl-5-methylphenyl group, 3,5-di -n- hexyl phenyl group is preferred.

Definitions and examples of the unsubstituted or substituted alkoxy group represented by R ¹⁵ and R ¹⁶ , the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group are each represented by R ^a . The definition and examples are the same as those of the unsubstituted or substituted alkoxy group, the unsubstituted or substituted aryloxy group, and the unsubstituted or substituted monovalent heterocyclic group.

  Formula (1-1), Formula (1-2), Formula (1-3), Formula (1-1-A), Formula (1-2-A), Formula (1-3-A) or Formula ( Examples of the structural unit represented by 1-1-B) include structural units represented by the following formulas (1-1) to (1-28), and are represented by the formulas (1-1) to (1-16). Is preferable, and the structural units represented by formulas (1-1) to (1-8) are more preferable.

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

(Structural unit represented by formula (2) and structural unit represented by formula (2 '))

In formula (2),
na represents an integer of 0 to 3, nb represents an integer of 0 to 12, nA represents 0 or 1, and n represents 1 or 2.
Ar ³ represents an unsubstituted or substituted (2 + n) -valent aromatic hydrocarbon 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 a plurality of X ′ are present, they may be the same or different.

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

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

  nA is preferably 0 because the luminance life obtained is more excellent when the polymer compound of this embodiment is used in the production of a light emitting device.

  n is preferably 2 because the luminance life obtained is more excellent when the polymer compound of the present embodiment is used in the production of a light emitting device.

The number of carbon atoms of the unsubstituted or substituted (2 + n) -valent aromatic hydrocarbon group represented by Ar ³ 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 represented by Ar ³ include a 1,3-phenylene group, a 1,4-phenylene group, and a 1,4-naphthalene group. Diyl group, 1,5-naphthalenediyl group, 2,6-naphthalenediyl group, 2,7-naphthalenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group 2,7-dihydrophenanthrenediyl group, 5,12-naphthacenediyl group, 2,7-fluorenediyl group, 3,6-fluorenediyl group, 1,6-pyrenediyl group, 2,7-pyrenediyl group, 3, Examples include 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-phenanthenediyl group, 2,7-dihydrophenanthenediyl group, 1,6 -Pyrenediyl group is preferable, 2,6-naphthalenediyl group and 2,7-fluorenediyl group are more preferable.

The number of carbon atoms of the unsubstituted or substituted (2 + n) -valent 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, and 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 ³ include a 2,5-thiophenediyl group, a 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-quinoxaline Examples include a diyl group, a 2,1,3-benzothiadiazole-4,7-diyl group, a 2,7-dibenzofurandiyl group, a 2,7-dibenzothiophenediyl group, and a 2,7-dibenzosiloldiyl group.

The group represented by Ar ³ may have a substituent, and examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted group, Examples thereof include an aryloxy group, a halogen atom, an unsubstituted or substituted monovalent heterocyclic group, and a cyano group.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ^{1 to} R ¹⁰ each represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, and an unsubstituted or substituted monovalent group. The definition and examples of the heterocyclic group are the same.

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 include definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted alkoxy group represented by R ^{1 to} R ¹⁰ , respectively. The same.

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

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

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

  Examples of the monovalent crosslinkable group represented by X ′ include 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. Since manufacture of a compound becomes easier, the monovalent | monohydric crosslinkable group shown by following formula (X'-1) and following formula (X'-2) is preferable.

The monovalent crosslinkable group represented by X ′ may have a substituent. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. A cyclic group and a cyano group are mentioned.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ^{1 to} R ¹⁰ each represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, and an unsubstituted or substituted monovalent group. The definition and examples of the heterocyclic group are the same.

  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 ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ and R ²¹ 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 ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ and R ^{21 each} have a higher luminance lifetime of the light-emitting element obtained when the polymer compound of this embodiment is used in the production of a light-emitting element. A substituted or substituted alkyl group or unsubstituted is preferable, and a hydrogen atom is more preferable.

R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ and R ²¹ 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, The definition and examples of the substituted or substituted monovalent heterocyclic group are the unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group and unsubstituted represented by R ^{1 to} R ¹⁰ , respectively. Or it is the same as the definition and example of a substituted aryloxy group and an unsubstituted or substituted monovalent | monohydric heterocyclic group.

  The structural unit represented by the formula (2) is more excellent in stability of the polymer compound of the present embodiment, and more excellent in crosslinkability of the present embodiment. Therefore, the total content of the structural units contained in the polymer compound Is preferably 0.5 to 40 mol%, more preferably 3 to 30 mol%, and still more preferably 3 to 20 mol%.

In formula (2 ′),
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).
Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ 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.
X ′ has 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 (2 ′) is different from the structural unit represented by the formula (1).

  c is 0 because the production of the polymer compound of this embodiment becomes easier and the hole transportability and durability of the light emitting device produced using the polymer compound of this embodiment are superior. Is preferred.

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 more excellent. .

The definition and examples of the unsubstituted or substituted arylene group represented by Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ are the definition of the unsubstituted or substituted arylene group represented by Ar ⁵ , Ar ⁶ and Ar ⁷ in formula (4) described below. Same as example.

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 2 represented by Ar ⁵ , Ar ⁶ and Ar ⁷ in formula (4) described later. The definition and example of the valent heterocyclic group are the same.

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 and a divalent heterocyclic group represented by Ar ³⁰ are linked are Ar ⁶ and Ar in formula (4) described later. ⁸ is the same as 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 and a divalent heterocyclic group represented by ⁸ 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.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: R ^{1 to} R ¹⁰ each represent an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, and an unsubstituted or substituted monovalent group. The definition and examples of the heterocyclic group are the same.

  The definitions and examples of monovalent crosslinkable groups represented by X ′ and X ″ are the same as the definitions and examples of monovalent crosslinkable groups represented by X ′ in Formula (2).

Definitions and examples of the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group represented by X ″ are the unsubstituted or substituted groups represented by R ^{1 to} R ¹⁰ , respectively. The definition and examples are the same as those of the alkyl group, unsubstituted or substituted aryl group, and unsubstituted or substituted monovalent heterocyclic group.

  X ″ is preferably the same monovalent crosslinkable group as X ′ because the production of the polymer compound of the present embodiment becomes easier and the crosslinkability of the polymer compound of the present embodiment is excellent. .

  Examples of the structural unit represented by the formula (2) include structural units represented by the following formulas (2-1) to (2-28). Examples of the structural unit represented by the formula (2 ′) include And structural units represented by the following formulas (2′-1) to (2′-7). Among these, since the crosslinkability of the polymer compound of this embodiment is excellent, the structural units represented by the formula (2-1) to the formula (2-28) are preferable, and the formula (2-1) to the formula (2) -16) and structural units represented by formula (2-17) to formula (2-26) are more preferred, and structural units represented by formula (2-1) to formula (2-13) are more preferred.

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

(Structural unit represented by Formula (3))

  In addition to the structural unit represented by the formula (1), the structural unit represented by the formula (2), and the structural unit represented by the formula (2 ′), the polymer compound of the present embodiment is further represented by the formula (3). It preferably includes the structural units shown.

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

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

As the arylene group represented by Ar ⁴ , when the polymer compound of this embodiment is used for the production of a light-emitting device, the resulting light-emitting device has a higher luminance life, and thus a 1,4-phenylene group, 2,7 -Full orangeyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthrenediyl group, 2,7-dihydrophenanthenediyl group, 2,6-naphthalenediyl group, 1,6 A -pyrene diyl group is preferable, and a 1,4-phenylene group and a 2,7-fluorenediyl group are more preferable.

The number of carbon atoms of the unsubstituted or substituted divalent heterocyclic group represented by Ar ⁴ does not include the number of carbon atoms of the substituent, and is preferably 3 to 30, more preferably 3 to 15, and still more preferably 4 to 15.
Examples of the divalent heterocyclic group represented by Ar ⁴ 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-dibenzofurandiyl group, 2,7-dibenzothiophenediyl group, 2,7-dibenzosiloldiyl group.

The arylene group and divalent heterocyclic group represented by Ar ⁴ may have a substituent. Examples of the substituent include an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. Examples thereof include a cyclic group and a cyano group, and an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferred.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: Unsubstituted or substituted alkyl group, unsubstituted or substituted alkoxy group, unsubstituted or substituted aryl group, unsubstituted or substituted aryloxy group and unsubstituted or substituted monovalent represented by R ^{1 to} R ¹⁰ , respectively. This is the same as the definition and example of the heterocyclic group of.

The polymer compound of this embodiment may contain only one kind of the above structural unit as the structural unit represented by the formula (3), or may contain a plurality of different structural units.
For example, the polymer compound of the present embodiment includes, as the structural unit represented by the formula (3), a structural unit composed of an unsubstituted or substituted fluorenediyl group, a structural unit composed of an unsubstituted or substituted phenylene group, May be included.

  As a structural unit shown by Formula (3), the structural unit shown by following formula (3-1)-(3-66) is mentioned, for example, In following formula (3-1)-(3-53), it is mentioned. The structural units shown are preferred. This is because when the polymer compound of the present embodiment is used for the production of a light emitting device, the obtained luminance life is more excellent.

  The structural unit represented by the formula (3) has a higher luminance life when the polymer compound of the present embodiment is used in the production of a light emitting device, and therefore the total content of the structural units contained in the polymer compound. The content is preferably 0.1 to 79.5 mol%, more preferably 20 to 70 mol%, and still more preferably 30 to 60 mol%.

(Structural unit represented by Formula (4))

  In addition to the structural unit represented by the formula (1), the structural unit represented by the formula (2), and the structural unit represented by the formula (2 ′), the polymer compound of the present embodiment is further represented by the formula (4). It preferably includes the structural units shown.

In formula (4), a ¹ and a ² each independently represent 0 or 1.
Ar ⁵ and Ar ⁷ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ⁶ and Ar ⁸ 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 ^C , R ^D and R ^E each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ 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 (4) is different from the structural unit represented by the formula (1) and the structural unit represented by the formula (2 ′).

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

a ² is preferably 0 because it is easy to produce the polymer compound of the present embodiment, and when the polymer compound is used in the production of a light-emitting device, the obtained luminance lifetime is more excellent.

R ^C , R ^D and R ^E are excellent in the stability of the polymer compound of the present embodiment, and when the polymer compound is used in the production of a light emitting device, the resulting luminance life is more excellent, A substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group is preferable, and an unsubstituted or substituted aryl group is more preferable.

Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ are unsubstituted or substituted arylene groups, the stability of the polymer compound of this embodiment is improved, and the polymer compound is produced as a light emitting device. When used for the above, it is preferable because the luminance life of the obtained light emitting element is more excellent.

The number of carbon atoms of the unsubstituted or substituted arylene group represented by Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ 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 groups represented by Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthalenediyl group, 1 , 5-naphthalenediyl group, 2,6-naphthalenediyl group, 2,7-naphthalenediyl group, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthenediyl group, 2,7 -Dihydrophenanthrene diyl group, 5,12-naphthacene diyl group, 2,7-fluorenediyl group, 3,6-fluorenediyl group, 1,6-pyrene diyl group, 2,7-pyrene diyl group, 3,9-perylene diyl group 3,10-perylenediyl group, 6,12-chrysenediyl group, 2,8-chrysenediyl group, 1,4-phenylene group, 2,7- Luorangeyl, 2,6-anthracenediyl group, 9,10-anthracenediyl group, 2,7-phenanthrenediyl group, 2,7-dihydrophenanthenediyl group, 1,6-pyrenediyl group are preferable, 1,4- A phenylene group and 2,7-fluorenediyl are more preferable.

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

Examples of the divalent group in which two or more identical or different groups selected from the group consisting of an arylene group represented by Ar ⁶ and Ar ⁸ and a divalent heterocyclic group are linked include the following formulas (1a-1), ( A group represented by 1a-2), (1a-3), (1a-4), (1a-5), (1a-6) or (1a-7) can be selected, and the group represented by the formula (1a-1) ) Is preferred.

The groups represented by Ar ⁵ , Ar ⁶ , Ar ⁷ and 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 aryloxy group, a halogen atom, an unsubstituted or substituted monovalent complex. Examples thereof include a cyclic group and a cyano group, and an unsubstituted or substituted alkyl group and an unsubstituted or substituted aryl group are preferred.
Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted alkoxy groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups are as follows: Definitions and examples of unsubstituted or substituted alkyl groups, unsubstituted or substituted aryl groups, unsubstituted or substituted aryloxy groups, and unsubstituted or substituted monovalent heterocyclic groups represented by R ^{1 to} R ¹⁰ , respectively. Is the same.

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

  Since the structural unit represented by the formula (4) is more excellent in the stability of the polymer compound of the present embodiment, it is 0.1 to 40 mol% with respect to the total content of the structural units contained in the polymer compound. Preferably, it is 0.5 to 30 mol%, more preferably 1 to 20 mol%.

  As a structural unit shown by Formula (4), the structural unit shown by following formula (4-1)-Formula (4-9) is mentioned, for example, Formula (4-1), Formula (4-2) Or the structural unit shown by Formula (4-3) is preferable, and the structural unit shown by Formula (4-2) or Formula (4-3) is more preferable.

  The structural unit represented by the formula (4) may be a structural unit represented by the following formula (5).

In Formula (5), R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
In formula (5), Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^{b s} may be the same or different, and may form a ring structure together with the carbon atom to which each R ^b is bonded.

^RF is not substituted or substituted because the stability of the polymer compound of this embodiment is improved and the luminance life of the resulting light-emitting device is better when the polymer compound is used in the production of a light-emitting device. It is preferably a substituted alkyl group, an unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent heterocyclic group, more preferably an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group. It is preferably an unsubstituted or substituted aryl group.

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

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

The definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ^b are the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ^{1 to} R ¹⁰ , respectively. Same as group definitions and examples.

  Examples of the structural unit represented by the formula (5) include structural units represented by the following formulas (5-1) to (5-7), and the polymer compound of this embodiment is used for the production of a light emitting device. In such a case, the luminance lifetime obtained is more excellent, and thus the structural units represented by the formulas (5-1) to (5-4) are preferable.

  Examples of combinations of the above structural units in the polymer compound of the present embodiment are shown below. In addition, Q1-Q133 represents the molar ratio of the structural unit in a parenthesis with respect to the total content of the structural unit contained in a high molecular compound.

（式中、
Ｑ１は２０〜５０の数を示し、Ｑ２は３〜２０の数を示し、Ｑ３は３〜２０の数を示し、Ｑ４は４０〜６０の数を示す。但し、Ｑ１＋Ｑ２＋Ｑ３＋Ｑ４＝１００である。
Ｑ５は３０〜５０の数を示し、Ｑ６は３〜２０の数を示し、Ｑ７は２０〜５０の数を示し、Ｑ８は２０〜５０の数を示す。但し、Ｑ５＋Ｑ６＋Ｑ７＋Ｑ８＝１００である。
Ｑ９は２０〜５０の数を示し、Ｑ１０は３〜２０の数を示し、Ｑ１１は３〜２０の数を示し、Ｑ１２は２０〜５０の数を示し、Ｑ１３は２０〜５０の数を示す。但し、Ｑ９＋Ｑ１０＋Ｑ１１＋Ｑ１２＋Ｑ１３＝１００である。
Ｑ１４は３０〜５０の数を示し、Ｑ１５は３〜２０の数を示し、Ｑ１６は４０〜６０の数を示し、Ｑ１７は１〜１０の数を示す。但し、Ｑ１４＋Ｑ１５＋Ｑ１６＋Ｑ１７＝１００である。）

(Where
Q1 represents a number of 20 to 50, Q2 represents a number of 3 to 20, Q3 represents a number of 3 to 20, and Q4 represents a number of 40 to 60. However, Q1 + Q2 + Q3 + Q4 = 100.
Q5 represents a number of 30 to 50, Q6 represents a number of 3 to 20, Q7 represents a number of 20 to 50, and Q8 represents a number of 20 to 50. However, Q5 + Q6 + Q7 + Q8 = 100.
Q9 represents a number of 20 to 50, Q10 represents a number of 3 to 20, Q11 represents a number of 3 to 20, Q12 represents a number of 20 to 50, and Q13 represents a number of 20 to 50. However, Q9 + Q10 + Q11 + Q12 + Q13 = 100.
Q14 represents a number of 30 to 50, Q15 represents a number of 3 to 20, Q16 represents a number of 40 to 60, and Q17 represents a number of 1 to 10. However, Q14 + Q15 + Q16 + Q17 = 100. )

（式中、
Ｑ１８は３０〜５０の数を示し、Ｑ１９は３〜２０の数を示し、Ｑ２０は２０〜５０の数を示し、Ｑ２１は２０〜５０の数を示す。但し、Ｑ１８＋Ｑ１９＋Ｑ２０＋Ｑ２１＝１００である。
Ｑ２２は２０〜５０の数を示し、Ｑ２３は３〜２０の数を示し、Ｑ２４は３〜２０の数を示し、Ｑ２５は４０〜６０の数を示す。但し、Ｑ２２＋Ｑ２３＋Ｑ２４＋Ｑ２５＝１００である。
Ｑ２６は３０〜５０の数を示し、Ｑ２７は３〜２０の数を示し、Ｑ２８は４０〜６０の数を示し、Ｑ２９は１〜１０の数を示す。但し、Ｑ２６＋Ｑ２７＋Ｑ２８＋Ｑ２９＝１００である。
Ｑ３０は２０〜５０の数を示し、Ｑ３１は３〜２０の数を示し、Ｑ３２は３〜２０の数を示し、Ｑ３３は２０〜５０の数を示し、Ｑ３４は２０〜５０の数を示す。但し、Ｑ３０＋Ｑ３１＋Ｑ３２＋Ｑ３３＋Ｑ３４＝１００である。
Ｑ３５は３０〜５０の数を示し、Ｑ３６は３〜２０の数を示し、Ｑ３７は２０〜５０の数を示し、Ｑ３８は２０〜５０の数を示す。但し、Ｑ３５＋Ｑ３６＋Ｑ３７＋Ｑ３８＝１００である。）

(Where
Q18 represents a number of 30 to 50, Q19 represents a number of 3 to 20, Q20 represents a number of 20 to 50, and Q21 represents a number of 20 to 50. However, Q18 + Q19 + Q20 + Q21 = 100.
Q22 represents a number of 20 to 50, Q23 represents a number of 3 to 20, Q24 represents a number of 3 to 20, and Q25 represents a number of 40 to 60. However, Q22 + Q23 + Q24 + Q25 = 100.
Q26 represents a number of 30 to 50, Q27 represents a number of 3 to 20, Q28 represents a number of 40 to 60, and Q29 represents a number of 1 to 10. However, Q26 + Q27 + Q28 + Q29 = 100.
Q30 represents a number from 20 to 50, Q31 represents a number from 3 to 20, Q32 represents a number from 3 to 20, Q33 represents a number from 20 to 50, and Q34 represents a number from 20 to 50. However, Q30 + Q31 + Q32 + Q33 + Q34 = 100.
Q35 represents a number of 30 to 50, Q36 represents a number of 3 to 20, Q37 represents a number of 20 to 50, and Q38 represents a number of 20 to 50. However, Q35 + Q36 + Q37 + Q38 = 100. )

（式中、
Ｑ３９は２０〜５０の数を示し、Ｑ４０は３〜２０の数を示し、Ｑ４１は３〜２０の数を示し、Ｑ４２は４０〜６０の数を示す。但し、Ｑ３９＋Ｑ４０＋Ｑ４１＋Ｑ４２＝１００である。
Ｑ４３は３０〜５０の数を示し、Ｑ４４は３〜２０の数を示し、Ｑ４５は４０〜６０の数を示し、Ｑ４６は１〜１０の数を示す。但し、Ｑ４３＋Ｑ４４＋Ｑ４５＋Ｑ４６＝１００である。
Ｑ４７は２０〜５０の数を示し、Ｑ４８は３〜２０の数を示し、Ｑ４９は３〜２０の数を示し、Ｑ５０は２０〜５０の数を示し、Ｑ５１は２０〜５０の数を示す。但し、Ｑ４７＋Ｑ４８＋Ｑ４９＋Ｑ５０＋Ｑ５１＝１００である。
Ｑ５２は３０〜５０の数を示し、Ｑ５３は３〜２０の数を示し、Ｑ５４は４０〜６０の数を示し、Ｑ５５は１〜１０の数を示す。但し、Ｑ５２＋Ｑ５３＋Ｑ５４＋Ｑ５５＝１００である。
Ｑ５６は３０〜５０の数を示し、Ｑ５７は３〜２０の数を示し、Ｑ５８は４０〜６０の数を示し、Ｑ５９は１〜１０の数を示す。但し、Ｑ５６＋Ｑ５７＋Ｑ５８＋Ｑ５９＝１００である。
Ｑ６０は２０〜５０の数を示し、Ｑ６１は３〜２０の数を示し、Ｑ６２は３〜２０の数を示し、Ｑ６３は４０〜６０の数を示す。但し、Ｑ６０＋Ｑ６１＋Ｑ６２＋Ｑ６３＝１００である。）

(Where
Q39 represents a number of 20 to 50, Q40 represents a number of 3 to 20, Q41 represents a number of 3 to 20, and Q42 represents a number of 40 to 60. However, Q39 + Q40 + Q41 + Q42 = 100.
Q43 represents a number of 30 to 50, Q44 represents a number of 3 to 20, Q45 represents a number of 40 to 60, and Q46 represents a number of 1 to 10. However, Q43 + Q44 + Q45 + Q46 = 100.
Q47 represents a number from 20 to 50, Q48 represents a number from 3 to 20, Q49 represents a number from 3 to 20, Q50 represents a number from 20 to 50, and Q51 represents a number from 20 to 50. However, Q47 + Q48 + Q49 + Q50 + Q51 = 100.
Q52 represents a number of 30 to 50, Q53 represents a number of 3 to 20, Q54 represents a number of 40 to 60, and Q55 represents a number of 1 to 10. However, Q52 + Q53 + Q54 + Q55 = 100.
Q56 represents a number of 30 to 50, Q57 represents a number of 3 to 20, Q58 represents a number of 40 to 60, and Q59 represents a number of 1 to 10. However, Q56 + Q57 + Q58 + Q59 = 100.
Q60 represents a number from 20 to 50, Q61 represents a number from 3 to 20, Q62 represents a number from 3 to 20, and Q63 represents a number from 40 to 60. However, Q60 + Q61 + Q62 + Q63 = 100. )

（式中、
Ｑ６４は３０〜５０の数を示し、Ｑ６５は３〜２０の数を示し、Ｑ６６は３０〜５０の数を示し、Ｑ６７は２０〜５０の数を示す。但し、Ｑ６４＋Ｑ６５＋Ｑ６６＋Ｑ６７＝１００である。
Ｑ６８は２０〜５０の数を示し、Ｑ６９は３〜２０の数を示し、Ｑ７０は３〜２０の数を示し、Ｑ７１は４０〜６０の数を示す。但し、Ｑ６８＋Ｑ６９＋Ｑ７０＋Ｑ７１＝１００である。
Ｑ７２は３０〜５０の数を示し、Ｑ７３は３〜２０の数を示し、Ｑ７４は２０〜５０の数を示し、Ｑ７５は２０〜５０の数を示す。但し、Ｑ７２＋Ｑ７３＋Ｑ７４＋Ｑ７５＝１００である。
Ｑ７６は３０〜５０の数を示し、Ｑ７７は３〜２０の数を示し、Ｑ７８は４０〜６０の数を示し、Ｑ７９は１〜１０の数を示す。但し、Ｑ７６＋Ｑ７７＋Ｑ７８＋Ｑ７９＝１００である。）

(Where
Q64 represents a number of 30 to 50, Q65 represents a number of 3 to 20, Q66 represents a number of 30 to 50, and Q67 represents a number of 20 to 50. However, Q64 + Q65 + Q66 + Q67 = 100.
Q68 shows the number of 20-50, Q69 shows the number of 3-20, Q70 shows the number of 3-20, Q71 shows the number of 40-60. However, Q68 + Q69 + Q70 + Q71 = 100.
Q72 shows the number of 30-50, Q73 shows the number of 3-20, Q74 shows the number of 20-50, Q75 shows the number of 20-50. However, Q72 + Q73 + Q74 + Q75 = 100.
Q76 represents a number of 30 to 50, Q77 represents a number of 3 to 20, Q78 represents a number of 40 to 60, and Q79 represents a number of 1 to 10. However, Q76 + Q77 + Q78 + Q79 = 100. )

（式中、
Ｑ８０は３０〜５０の数を示し、Ｑ８１は３〜２０の数を示し、Ｑ８２は４０〜７０の数を示す。但し、Ｑ８０＋Ｑ８１＋Ｑ８２＝１００である。
Ｑ８３は３０〜５０の数を示し、Ｑ８４は３〜２０の数を示し、Ｑ８５は４０〜６０の数を示し、Ｑ８６は１〜１０の数を示す。但し、Ｑ８３＋Ｑ８４＋Ｑ８５＋Ｑ８６＝１００である。
Ｑ８７は２０〜５０の数を示し、Ｑ８８は３〜２０の数を示し、Ｑ８９は３〜２０の数を示し、Ｑ９０は４０〜６０の数を示す。但し、Ｑ８７＋Ｑ８８＋Ｑ８９＋Ｑ９０＝１００である。
Ｑ９１は２０〜５０の数を示し、Ｑ９２は３〜２０の数を示し、Ｑ９３は３〜２０の数を示し、Ｑ９４は４０〜６０の数を示す。但し、Ｑ９１＋Ｑ９２＋Ｑ９３＋Ｑ９４＝１００である。）

(Where
Q80 shows the number of 30-50, Q81 shows the number of 3-20, Q82 shows the number of 40-70. However, Q80 + Q81 + Q82 = 100.
Q83 represents a number of 30 to 50, Q84 represents a number of 3 to 20, Q85 represents a number of 40 to 60, and Q86 represents a number of 1 to 10. However, Q83 + Q84 + Q85 + Q86 = 100.
Q87 represents a number of 20 to 50, Q88 represents a number of 3 to 20, Q89 represents a number of 3 to 20, and Q90 represents a number of 40 to 60. However, Q87 + Q88 + Q89 + Q90 = 100.
Q91 represents a number from 20 to 50, Q92 represents a number from 3 to 20, Q93 represents a number from 3 to 20, and Q94 represents a number from 40 to 60. However, Q91 + Q92 + Q93 + Q94 = 100. )

（式中、
Ｑ９５は２０〜５０の数を示し、Ｑ９６は３〜２０の数を示し、Ｑ９７は３〜２０の数を示し、Ｑ９８は４０〜６０の数を示し、Ｑ９９は１〜１０の数を示す。但し、Ｑ９５＋Ｑ９６＋Ｑ９７＋Ｑ９８＋Ｑ９９＝１００である。
Ｑ１００は３０〜５０の数を示し、Ｑ１０１は３〜２０の数を示し、Ｑ１０２は２０〜５０の数を示し、Ｑ１０３は２０〜５０の数を示す。但し、Ｑ１００＋Ｑ１０１＋Ｑ１０２＋Ｑ１０３＝１００である。
Ｑ１０４は３０〜５０の数を示し、Ｑ１０５は３〜２０の数を示し、Ｑ１０６は４０〜７０の数を示す。但し、Ｑ１０４＋Ｑ１０５＋Ｑ１０６＝１００である。
Ｑ１０７は２０〜５０の数を示し、Ｑ１０８は３〜２０の数を示し、Ｑ１０９は３〜２０の数を示し、Ｑ１１０は４０〜６０の数を示す。但し、Ｑ１０７＋Ｑ１０８＋Ｑ１０９＋Ｑ１１０＝１００である。）

(Where
Q95 represents a number of 20 to 50, Q96 represents a number of 3 to 20, Q97 represents a number of 3 to 20, Q98 represents a number of 40 to 60, and Q99 represents a number of 1 to 10. However, Q95 + Q96 + Q97 + Q98 + Q99 = 100.
Q100 represents a number of 30 to 50, Q101 represents a number of 3 to 20, Q102 represents a number of 20 to 50, and Q103 represents a number of 20 to 50. However, Q100 + Q101 + Q102 + Q103 = 100.
Q104 represents a number of 30 to 50, Q105 represents a number of 3 to 20, and Q106 represents a number of 40 to 70. However, Q104 + Q105 + Q106 = 100.
Q107 represents a number from 20 to 50, Q108 represents a number from 3 to 20, Q109 represents a number from 3 to 20, and Q110 represents a number from 40 to 60. However, Q107 + Q108 + Q109 + Q110 = 100. )

（式中、
Ｑ１１１は３０〜５０の数を示し、Ｑ１１２は３〜２０の数を示し、Ｑ１１３は４０〜６０の数を示し、Ｑ１１４は１〜１０の数を示す。但し、Ｑ１１１＋Ｑ１１２＋Ｑ１１３＋Ｑ１１４＝１００である。
Ｑ１１５は２０〜５０の数を示し、Ｑ１１６は３〜２０の数を示し、Ｑ１１７は３〜２０の数を示し、Ｑ１１８は４０〜６０の数を示す。但し、Ｑ１１５＋Ｑ１１６＋Ｑ１１７＋Ｑ１１８＝１００である。
Ｑ１１９は３０〜５０の数を示し、Ｑ１２０は３〜２０の数を示し、Ｑ１２１は４０〜６０の数を示し、Ｑ１２２は１〜１０の数を示す。但し、Ｑ１１９＋Ｑ１２０＋Ｑ１２１＋Ｑ１２２＝１００である。
Ｑ１２３は２０〜５０の数を示し、Ｑ１２４は３〜２０の数を示し、Ｑ１２５は３〜２０の数を示し、Ｑ１２６は４０〜６０の数を示す。但し、Ｑ１２３＋Ｑ１２４＋Ｑ１２５＋Ｑ１２６＝１００である。
Ｑ１２７は２０〜５０の数を示し、Ｑ１２８は３〜２０の数を示し、Ｑ１２９は４０〜６０の数を示し、Ｑ１３０は１〜１０の数を示す。但し、Ｑ１２７＋Ｑ１２８＋Ｑ１２９＋Ｑ１３０＝１００である。）

(Where
Q111 represents a number of 30 to 50, Q112 represents a number of 3 to 20, Q113 represents a number of 40 to 60, and Q114 represents a number of 1 to 10. However, Q111 + Q112 + Q113 + Q114 = 100.
Q115 represents a number of 20 to 50, Q116 represents a number of 3 to 20, Q117 represents a number of 3 to 20, and Q118 represents a number of 40 to 60. However, Q115 + Q116 + Q117 + Q118 = 100.
Q119 represents a number of 30 to 50, Q120 represents a number of 3 to 20, Q121 represents a number of 40 to 60, and Q122 represents a number of 1 to 10. However, Q119 + Q120 + Q121 + Q122 = 100.
Q123 represents a number of 20 to 50, Q124 represents a number of 3 to 20, Q125 represents a number of 3 to 20, and Q126 represents a number of 40 to 60. However, Q123 + Q124 + Q125 + Q126 = 100.
Q127 represents a number of 20 to 50, Q128 represents a number of 3 to 20, Q129 represents a number of 40 to 60, and Q130 represents a number of 1 to 10. However, Q127 + Q128 + Q129 + Q130 = 100. )

（式中、
Ｑ１３１は３０〜５０の数を示し、Ｑ１３２は３〜２０の数を示し、Ｑ１３３は４０〜７０の数を示す。但し、Ｑ１３１＋Ｑ１３２＋Ｑ１３３＝１００である。）

(Where
Q131 shows the number of 30-50, Q132 shows the number of 3-20, Q133 shows the number of 40-70. However, Q131 + Q132 + Q133 = 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 >.

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

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

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

  In the production of the polymer compound of the present embodiment, for example, a compound represented by the following formula (1-1-M) (hereinafter sometimes referred to as “compound 1-1-M”), or a compound represented by the following formula (1-2): -M) (hereinafter sometimes referred to as “compound 1-2M”) and a compound represented by the following formula (1-3-M) (hereinafter sometimes referred to as “compound 1-3-3-M”). At least one compound selected from the group consisting of: a compound represented by the following formula (2M) (hereinafter sometimes referred to as “compound 2M”) and / or a compound represented by the formula (2′M): (Hereinafter sometimes referred to as “compound 2′M”) and other monomers (for example, a compound represented by the following formula (3M) (hereinafter sometimes referred to as “compound 3M”) and / or the following formula (4M ) (Hereinafter referred to as field) By "compound 4M".)) And can be prepared by condensation polymerization of. In this specification, Compound 1-1-M, Compound 1-2-M, Compound 1-3-M, Compound 2M, Compound 2′M, Compound 3M, and Compound 4M are collectively referred to as “monomer”. is there.

In formula (1-1-M) to formula (1-3-M), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ^{A 1} , R ^B , Ar ¹ , Ar ² , X and Y are as defined above, and Z ¹ and Z ² are each independently the following substituent group (the following substituent group A and the following substituent group B). The group selected from is shown.

In formula (2M), na, nb, nA, n, Ar ³ , L ^a , L ^b , L ^A and X ′ are as defined above, and Z ³ and Z ⁴ are each independently the following substituents A group selected from the group (the following substituent group A and the following substituent group B) is shown.

In formula (2′M), c, Ar ²⁰ , Ar ³⁰ , Ar ⁴⁰ , X ′, and X ″ are as defined above, and Z ⁵ and Z ⁶ are each independently the following substituent group ( And a group selected from the following substituent group A and the following substituent group B).

In formula (3M), Ar ⁴ has the same meaning as described above, and Z ⁷ and Z ⁸ each independently represent a group selected from the following substituent group (the following substituent group A and the following substituent group B). .

In formula (4M), a ¹ , a ² , Ar ⁵ , Ar ⁶ , Ar ⁷ , Ar ⁸ , R ^C , R ^D and R ^E are as defined above, and Z ⁹ and Z ¹⁰ are each independently And a group selected from the following substituent group (the following substituent group A or the following substituent group B).

<Substituent group A>
A chlorine atom, a bromine atom, an iodine atom, —O—S (═O) ₂ R ⁴¹ (R ⁴¹ is a group represented by an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group.

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

The definitions and examples of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ⁴¹ are as follows: the unsubstituted or substituted alkyl group represented by R ^{1 to} R ¹⁰ and the unsubstituted or substituted aryl group, respectively. Same as group definitions and examples.

Definition and examples of an unsubstituted or substituted alkyl group represented by R ⁴² are respectively the same as definitions and examples of an unsubstituted or substituted alkyl group represented by R ¹ to R ^10.

The definition and examples of the unsubstituted or substituted alkyl group represented by R ⁴³ are the same as the definitions and examples of the unsubstituted or substituted alkyl group represented by R ^{1 to} R ¹⁰ , respectively.

  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, Z ¹ and Z ² in compound 1-1-M (or compound 1-2-M or compound 1-3-M) and Z ³ and Z ⁴ in compound 2M (or compound 2′M) (or , Z ⁵ and Z ⁶ ) are groups selected from the substituent group A, Z ⁷ and Z ⁸ (or Z ⁹ and Z ¹⁰ ) in the compound 3M (or compound 4M) are the substituent group B A group selected from can be selected.
Further, Z ¹ and Z ² in Compound 1-1-M (or Compound 1-2-M or Compound 1-3-M) and Z ³ and Z ⁴ in Compound 2M (or Compound 2′M) (or , Z ⁵ and Z ⁶ ) are groups selected from the substituent group B, Z ⁷ and Z ⁸ (or Z ⁹ and Z ¹⁰ ) in the compound 3M (or compound 4M) are the substituent group A. A group selected from can be selected.

  Compounds represented by the formulas (1-1-M), (1-2-M), (1-3-M), (2M), (2′M), (3M), and (4M) are synthesized in advance. The isolated product can be used, or it can be prepared in a reaction system and used as it is.

  As a method of condensation polymerization, the formulas (1-1-M), (1-2-M), (1-3-M), (2M), (2′M), (3M), (4M) Examples include a method in which the compound shown 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.

  In the case of using a catalyst, the amount used is the formula (1-1-M), (1-2-M), (1-3-M), (2M), (2′M), (3M). The amount of transition metal relative to the total number of moles of the compound represented by (4M) is preferably 0.00001 to 3 molar equivalents, more preferably 0.00005 to 2 molar equivalents, and further 0.0001 to 1 molar equivalents. preferable.

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

  When a base is used, the amount used is the formula (1-1-M), (1-2-M), (1-3-M), (2M), (2′M), (3M) The molar number of the compound represented by (4M) is preferably 0.5 to 20 molar equivalents, and more preferably 1 to 10 molar equivalents.

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

  The organic solvent is a compound of the formula (1M), (1-2-M), (1-3-M), (2M), (2′M), (3M), or (4M) For example, toluene, xylene, mesitylene, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, N, N-dimethylacetamide, and 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 that of the compound represented by the formula (1M), (1-2-M), (1-3-M), (2M), (2′M), (3M), or (4M). The total concentration is usually 0.1 to 90% by weight, preferably 1 to 50% by weight, more preferably 2 to 30% by weight.

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

In the polymerization reaction, a compound represented by the following formula (1T) is used as a polymerization terminator in order to avoid leaving a polymerizable group (for example, Z ¹ , Z ² ) at the terminal of the polymer compound of the present embodiment. May be. 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 aryl group which may have a substituent, or a monovalent heterocyclic group which may have a substituent (particularly a monovalent aromatic heterocyclic group). Z ^T represents a group selected from the group consisting of the substituent group A and the substituent group B. As the aryl group or monovalent heterocyclic group (particularly, monovalent aromatic heterocyclic group) in Ar ^T , the above-described unsubstituted or substituted aryl group, unsubstituted or substituted, exemplified as R ^{1 to} R ¹⁰ , respectively. Examples thereof are the same as the substituted monovalent heterocyclic group (particularly, a monovalent aromatic heterocyclic group).

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

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

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

(Compound)
The compound represented by the following formula (1-1-M), the compound represented by the following formula (1-2-M) and the compound represented by the following formula (1-3-M) are those of the polymer compound of the present invention. It can be suitably used for production.

In formula (1-1-M) to formula (1-3-M), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ^{A 1} , R ^B , Ar ¹ , Ar ² , X and Y are as defined above, and Z ¹ and Z ² are each independently the above substituent group (the above substituent group A and the above substituent group B). The group selected from is shown.

  The compound represented by the formula (1-1-M), the compound represented by the formula (1-2-M), and the compound represented by the formula (1-3-M) are respectively the polymer compound of the present embodiment. When used in the production of a light emitting device, the resulting luminance lifetime is more excellent, so that a compound represented by the following formula (1-1-AM), a compound represented by the formula (1-2-AM), and A compound represented by the formula (1-3-AM) is preferable, and a compound represented by the following formula (1-1-BM) is more preferable.

Wherein (1-1-A-M) ~ formula ^(1-3-A-M), n 1, n 2, X, Y, R 5, R 6, R 7, R 8, R 9, R 10 , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above, and Z ¹ and Z ² are each independently the above substituent group (the above substituent group) A group selected from the group A and the following substituent group B).

Wherein ^(1-1-B-M), n 1, n 2, 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 ^A , R ^B , Ar ¹ and Ar ² are as defined above, and Z ¹ and Z ² are each independently the above substituent group (the above substituent group A and the following substituent group B). The group selected from is shown.

  The method for producing the compound represented by the formula (1-1-M) will be described using the compound represented by the formula (1-1-BM) as an example. The compound represented by the formula (1-1-BM) can be produced, for example, by the method described in Scheme 1 below.

スキーム１

Scheme 1

In Scheme 1, Y ^1a and Y ^2a each independently represent a hydrogen atom or a group selected from the substituent group A, Y ^1b represents a group selected from the substituent group B, and Y ^3a and Y ^4a are Each independently represents a chlorine atom, a bromine atom or an iodine atom, Y ^1c represents a chlorine atom, a bromine atom or an iodine atom,
Z ^1a and Z ^2a represent a group selected from the substituent group A,
R ^1a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group; R ^2a represents a hydrogen atom or an unsubstituted or substituted alkyl group R ^3a represents an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ , Ar ² , R ^A and R ^B are as defined above.
A plurality of R ^1a may be the same as or different from each other, Y ^3a and Y ^4a are different from each other, and Y ^4a represents an atom having an atomic number larger than that of Y ^3a .

Y ^3a is preferably a chlorine atom or a bromine atom, and more preferably a bromine atom.

Y ^4a is preferably a bromine atom or an iodine atom, and more preferably an iodine atom.

The definition and examples of the unsubstituted or substituted alkyl group represented by R ^1a , the unsubstituted or substituted aryl group, or the unsubstituted or substituted monovalent heterocyclic group are the unsubstituted or substituted represented by R ^{1 to} R ^10. The definition and examples are the same as those of the alkyl group, unsubstituted or substituted aryl group, and unsubstituted or substituted monovalent heterocyclic group.

The definition and examples of the unsubstituted or substituted alkyl group represented by R ^2a are the same as the definitions and examples of the unsubstituted or substituted alkyl group represented by R ^{1 to} R ¹⁰ .

Definitions and examples of the unsubstituted or substituted alkyl group represented by R ^3a , the unsubstituted or substituted aryl group, or the unsubstituted or substituted monovalent heterocyclic group are the unsubstituted or substituted groups represented by R ¹⁵ and R ¹⁶ The definition and examples are the same as those of the alkyl group, unsubstituted or substituted aryl group, and unsubstituted or substituted monovalent heterocyclic group.

  In Scheme 1, first, a compound represented by the formula (6-1-1) (hereinafter referred to as “compound (6-1-1)”; the same shall apply hereinafter) and a predetermined amine compound are combined to form a compound. (6-1-2) is obtained.

Here, when Y ^1a and Y ^2a are hydrogen atoms, the compound (6-1-1) is subjected to a reaction such as bromination reaction, and Y ^1a and Y ^2a are groups selected from the substituent group A Convert to

  Next, the compound (6-1-2) is converted into a group selected from the substituent group B using a known reaction to obtain the compound (6-1-3).

  Subsequently, a compound (6-1-4) is obtained by a Suzuki coupling reaction between the compound (6-1-3) and a predetermined halogen compound.

  Subsequently, a compound (6-1-5) is obtained by an addition reaction using the compound (6-1-4) and a Gringard reagent. In this step, an addition reaction using an organolithium reagent can be used in addition to the addition reaction using a Gringard reagent.

  Next, a compound (6-1-6) is obtained by a cyclization reaction using the compound (6-1-5) and an acid.

  Subsequently, a compound (6-1-7) is obtained by a coupling reaction between the compound (6-1-6) and a predetermined amine compound.

Next, by subjecting the compound (6-1-7) to a reaction such as bromination reaction, the hydrogen atom directly bonded to the carbon atoms constituting Ar ¹ and Ar ² is converted into a group selected from the substituent group A. , A compound (6-1-8) is obtained. In addition, compound (6-1-8) can also be converted to a group selected from substituent group B using a known reaction.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  The organic thin film of the present invention includes, 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, It can be produced by a flexographic 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 at least one layer of a hole transport layer, a hole injection layer and an interlayer layer, and it is at least one layer of a hole transport layer, a hole injection layer and an interlayer layer. Further preferred. In addition, when the layer containing the polymer compound of the present invention functions as a hole transport layer, a hole injection layer, or an interlayer layer, the layer is preferably a layer made of the insolubilized organic thin film of the present invention.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

  When the light emitting element of this embodiment has a hole transport layer, the polymer compound of this embodiment can be suitably used for the hole transport layer. In addition, hole transport materials (high molecular weight compounds, low molecular weight compounds) can also be used for the hole transport layer. The 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, polyaniline. 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, JP-A 63-70257, Examples described in JP-A-63-175860, JP-A-2-135359, JP-A-2-135361, JP-A-2-209988, JP-A-3-37992, and JP-A-3-152184 are exemplified. The

  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 film formation method of the hole transport layer, when the polymer compound of the present embodiment is used, a method of film formation from the solution of the present embodiment is exemplified. In the case of using a low molecular weight compound, a method by film formation 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 organic thin film or the 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. As the column, 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) was used.

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

<Synthesis Example 1>
(Synthesis of Compound 2)
First, Compound 2 was synthesized using Compound 1 as follows.

  In a 1000 mL four-necked flask equipped with a stirrer, compound 1 (93.4 g), N-phenyl-N- (4-butyl) -2,6-dimethylphenylamine (28.3 g), tris ( Dibenzylideneacetone) dipalladium (0) (2.04 g), 1,1′-bis (diphenylphosphino) ferrocene (1.30 g), and sodium tert-butoxide (32.2 g) were placed in the flask. The gas was replaced with nitrogen gas. Toluene (700 mL) was added thereto, and the mixture was heated to 100 ° C. and stirred while keeping the temperature for 3 hours.

  The obtained reaction liquid was cooled to room temperature, water was added, and the mixture was filtered through a filter pre-coated with Celite, the residue was washed with toluene, the aqueous layer was separated from the filtrate, and the organic layer was washed with water. The obtained organic layer was concentrated to obtain a crude product. The crude product was recrystallized with toluene, and then purified using a silica gel column (developing solvent hexane / toluene mixture) to obtain 32.1 g of Compound 2 as a white solid.

LC-MS (APCI, positive): [M + H] ⁺ 590
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.98 (3H, t), 1.43 (4H, m), 1.66 (4H, m), 1.89 (2H M), 1.96 (2H, m), 2.00 (2H, m), 2.03 (6H, s), 2.17 (2H, m), 2.62 (2H, t), 6 .74 (1H, d), 6.88 (1H, t), 7.00 (2H, d), 7.00 (2H, s), 7.04 (1H, s), 7.20 (2H, t), 7.29 (1H, d), 7.51 (1H, s), 7.74 (1H, d), 7.74 (1H, d).

<Synthesis Example 2>
(Synthesis of Compound 3)
Using compound 2, compound 3 was synthesized as follows.

  To a 1000 mL four-necked flask equipped with a stirrer, compound 2 (30.0 g) and bis (pinacolato) diboron (4,4,4 ′, 4 ′, 5,5,5′-octamethyl- 2,2′-bi-1,3,2-dioxaborolane) (18.9 g), 1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex (0.61 g), 1,1′-bis (diphenylphosphino) ferrocene (0.42 g) and potassium acetate (14.6 g) were added, and the gas in the flask was replaced with nitrogen gas. 1,4-dioxane (540 mL) was added thereto, and then the temperature was raised to 100 ° C. and stirred while keeping the temperature for 19 hours.

  The obtained reaction liquid was cooled to room temperature, water was added, and the mixture was filtered through a filter pre-coated with Celite, the residue was washed with toluene, the aqueous layer was separated from the filtrate, and the organic layer was washed with water. The obtained organic layer was concentrated, and the crude product was dissolved in toluene (200 ml) and hexane (200 ml). The temperature was raised to 70 ° C., and activated carbon (3.0 g) was added and stirred while keeping the temperature for 30 minutes. Thereafter, the mixture was filtered through a filter precoated with silica gel, and the residue was washed with toluene. The resulting solution was concentrated to obtain a crude product. The crude product was recrystallized with a mixture of acetonitrile and toluene to obtain 24.8 g of Compound 3 as a white solid.

LC-MS (APCI, positive): [M + H] ⁺ 638
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.99 (3H, t), 1.35 (12H, s), 1.43 (2H, m), 1.44 (2H , M), 1.62 (2H, m), 1.67 (2H, m), 1.89 (2H, m), 2.00 (4H, m), 2.03 (6H, s), 2 .18 (2H, m), 2.63 (2H, t), 6.76 (1H, d), 6.87 (1H, t), 7.01 (2H, s), 7.01 (2H, d), 7.04 (2H, s), 7.20 (2H, s), 7.55 (1H, s), 7.78 (1H, s), 7.80 (2H, d), 7. 81 (2H, d).

<Synthesis Example 3>
(Synthesis of Compound 4)
Using compound 3, compound 4 was synthesized as follows.

  In a 1000 mL four-necked flask equipped with a stirrer, compound 3 (22.8 g), methyl-5-bromo-2-iodobenzoate (14.3 g), and a 20 wt% tetraethylammonium hydroxide aqueous solution (90 3 g), and the gas in the flask was replaced with nitrogen gas. Toluene (640 mL) was added thereto, and the mixture was heated to 90 ° C. and stirred for 4 hours.

  The obtained reaction liquid was cooled to room temperature, water was added, and the mixture was filtered through a filter pre-coated with Celite, the residue was washed with toluene, the aqueous layer was separated from the filtrate, and the organic layer was washed with water. The obtained organic layer was concentrated, and the crude product was dissolved in toluene (100 ml) and hexane (100 ml). The temperature was raised to 70 ° C., and activated carbon (3.0 g) was added and stirred while keeping the temperature for 30 minutes. Thereafter, the mixture was filtered through a filter precoated with silica gel, and the residue was washed with toluene. The resulting solution was concentrated to obtain a crude product. The crude product was purified using a silica gel column (developing solvent: hexane and toluene mixed solution) to obtain 18.9 g of Compound 4 as a pale yellow solid.

LC-MS (APCI, positive): [M + H] ⁺ 724
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.99 (3H, t), 1.43 (4H, m), 1.66 (4H, m), 1.92 (2H , M), 1.93 (2H, m), 2.01 (2H, m), 2.04 (6H, s), 2.17 (2H, m), 2.67 (2H, t), 3 .63 (3H, s), 6.77 (1H, d), 6.88 (1H, t), 7.00 (2H, s), 7.00 (2H, d), 7.07 (1H, s), 7.16 (1H, d), 7.19 (1H, d), 7.21 (2H, t), 7.29 (1H, s), 7.40 (1H, d), 7. 80 (1H, d), 7.87 (1H, d), 7.89 (1H, s).

<Synthesis Example 4>
(Synthesis of Compound 5)
Using compound 4, compound 5 was synthesized as follows.

  The inside of a 1000 mL four-necked flask equipped with a stirrer was replaced with nitrogen gas, compound 4 (16.4 g) and dehydrated tetrahydrofuran (450 mL) were added, and the mixture was cooled to 0 ° C. Thereto, methylmagnesium chloride (3 mol / L tetrahydrofuran solution) (84.2 ml) was slowly added dropwise over 20 minutes. After the exotherm subsided, the mixture was warmed to room temperature and stirred for 8 hours.

  The obtained reaction solution was cooled to 0 ° C., 1 mol / L aqueous hydrochloric acid was slowly added, and the mixture was stirred while being kept warm for 30 minutes. Thereafter, the mixture was filtered through a filter pre-coated with Celite, the residue was washed with toluene, the aqueous layer was separated from the filtrate, and the organic layer was washed with water. The obtained organic layer is concentrated, and the crude product is dissolved in a mixed solvent of toluene (70 ml) and hexane (70 ml). The temperature is raised to 70 ° C., and activated carbon (2.0 g) is added and stirred while keeping the temperature for 30 minutes. did. Thereafter, the mixture was filtered through a filter precoated with silica gel, and the residue was washed with toluene. The resulting solution was concentrated to obtain a crude product. The crude product was purified using a silica gel column (developing solvent: hexane and toluene mixed solution) to obtain 11.6 g of Compound 5 as a white solid.

LC-MS (APCI, positive): [M + H] ⁺ 724
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.99 (3H, t), 1.32 (6H, s), 1.43 (2H, m), 1.44 (2H M), 1.61 (2H, m), 1.67 (2H, m), 1.93 (2H, m), 2.00 (2H, m), 2.04 (2H, m), 2 .05 (6H, s), 2.15 (2H, m), 2.63 (2H, t), 4.14 (1H, s), 6.77 (1H, d), 6.88 (1H, t), 6.98 (1H, d), 7.01 (2H, s), 7.01 (2H, d), 7.06 (1H, d), 7.08 (1H, s), 7. 21 (2H, t), 7.25 (1H, s), 7.36 (1H, d), 7.80 (1H, d), 7.83 (1H, d), 8.14 (1H, s) ).

<Synthesis Example 5>
(Synthesis of Compound 6)
Using compound 5, compound 6 was synthesized as follows.

  The inside of a 500 mL four-necked flask equipped with a stirrer was replaced with nitrogen gas, Compound 5 (10.9 g) and dehydrated tedichloromethane (220 mL) were added, and the mixture was cooled to 0 ° C. A trifluoroborane-ethyl ether complex (14.7 ml) was slowly added dropwise over 10 minutes, and the mixture was stirred while keeping the temperature for 2 hours.

  Water was slowly added to the obtained reaction solution, and the mixture was stirred for 1 hour while keeping warm. Thereafter, the mixture was filtered through a filter pre-coated with Celite, the residue was washed with toluene, the aqueous layer was separated from the filtrate, and the organic layer was washed with water. The obtained organic layer was concentrated, and the crude product was dissolved in toluene (40 ml) and hexane (40 ml). The temperature was raised to 70 ° C., and activated carbon (1.0 g) was added and stirred while keeping the temperature for 30 minutes. Thereafter, the mixture was filtered through a filter precoated with silica gel, and the residue was washed with toluene. The resulting solution was concentrated to obtain a crude product. The crude product was purified using a silica gel column (developing solvent hexane / toluene mixture). The obtained solution was concentrated and recrystallized with a mixed solution of isopropanol and toluene to obtain 8.3 g of Compound 6 as a white solid.

LC-MS (APCI, positive): [M + H] ⁺ 706
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.99 (3H, t), 1.42 (3H, m), 1.47 (2H, m), 1.53 (6H) , S), 1.66 (2H, m), 1.67 (2H, m), 1.92 (2H, m), 2.03 (2H, m), 2.05 (6H, s), 2 0.09 (2H, m), 2.25 (2H, m), 2.63 (2H, t), 6.81 (1H, d), 6.88 (1H, t), 7.02 (2H, d), 7.02 (2H, s), 7.05 (1H, s), 7.21 (2H, t), 7.47 (1H, d), 7.65 (1H, s), 7. 68 (1H, d), 7.76 (1H, s), 7.89 (1H, d), 7.95 (1H, s).

<Synthesis Example 6>
(Synthesis of Compound 7)
Using compound 6, compound 7 was synthesized as follows.

  In a 500 mL four-necked flask equipped with a stirrer, compound 6 (8.14 g), N-phenyl-N- (4-butyl) -2,6-dimethylphenylamine (4.49 g), Tris ( Dibenzylideneacetone) dipalladium (0) (0.52 g), tri-tert-butylphosphonium tetrafluoroborate (0.67 g), sodium tert-butoxide (3.33 g), and tert-butanol (4.10 g) ) And the gas in the flask was replaced with nitrogen gas. Toluene (200 mL) was added thereto, and then the temperature was raised to 100 ° C. and stirred while keeping the temperature for 3 hours.

  The obtained reaction liquid was cooled to room temperature, water was added, and the mixture was filtered through a filter pre-coated with Celite, the residue was washed with toluene, the aqueous layer was separated from the filtrate, and the organic layer was washed with water. The obtained organic layer is concentrated, and the crude product is dissolved in a mixed solvent of toluene (50 ml) and hexane (50 ml). The temperature is raised to 70 ° C., and activated carbon (1.0 g) is added and stirred while keeping the temperature for 30 minutes. did. Thereafter, the mixture was filtered through a filter precoated with silica gel, and the residue was washed with toluene. The resulting solution was concentrated to obtain a crude product. The crude product was purified using a silica gel column (developing solvent: a mixture of hexane and toluene). The resulting solution was concentrated and recrystallized with a mixed solution of isopropanol and toluene to obtain 5.5 g of Compound 7 as a pale yellow solid.

LC-MS (APCI, positive): [M + H] ⁺ 879
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.99 (3H, t), 1.43 (4H, m), 1.44 (6H, s), 1.46 (2H M), 1.64 (2H, m), 1.67 (4H, m), 1.92 (2H, m), 2.02 (2H, m), 2.04 (12H, m), 2 0.08 (2H, m), 2.23 (2H, m), 2.63 (4H, t), 6.79 (1H, d), 6.84 (1H, t), 6.86 (1H, t), 6.86 (1H, t), 7.00 (2H, d), 7.00 (2H, d), 7.01 (2H, s), 7.01 (2H, s), 7. 04 (1H, s), 7.19 (2H, t), 7.19 (2H, t), 7.19 (1H, s), 7.54 (1H, d), 7.62 (1H, s) ), 7.84 (1H, d), 7.87 ( H, s).

<Synthesis Example 7>
(Synthesis of Compound 8)
Using compound 7, compound 8 was synthesized as follows.

  The gas in a 300 mL four-necked flask equipped with a stirrer was replaced with nitrogen gas, and compound 7 (4.96 g), N, N-dimethylformamide (6.8 mL) and chloroform (100 mL) were added, and at room temperature. Dissolved. Thereafter, the entire flask was shielded from light, and N-bromosuccinimide (NBS) (2.00 g) was added in portions at room temperature. After stirring for 4 hours at room temperature while stirring, water was added, and then a saturated aqueous sodium sulfite solution was added until the bromine color disappeared. After raising the temperature to room temperature, chloroform was added to the resulting solution, and the aqueous layer was separated. Thereafter, the organic layer was washed twice with water and concentrated to obtain a crude product. The crude product was dissolved in a mixed solvent of toluene (40 ml) and hexane (40 ml), heated to 70 ° C., charged with activated carbon (1.0 g), and stirred for 30 minutes. Thereafter, the mixture was filtered through a filter precoated with silica gel, and the residue was washed with toluene. The resulting solution was concentrated to obtain a crude product. The crude product was purified using a silica gel column (developing solvent: a mixture of hexane and toluene). The obtained solution was concentrated and recrystallized with a mixed solution of isopropanol and toluene to obtain 4.7 g of Compound 8 as a pale yellow solid.

LC-MS (APCI, positive): [M + H] ⁺ 1035
¹ H-NMR (THF-d ₈ , 600 MHz): δ (ppm) = 0.99 (3H, t), 1.44 (4H, m), 1.44 (6H, s), 1.46 (2H M), 1.66 (2H, m), 1.66 (4H, m), 1.92 (2H, m), 2.05 (2H, m), 2.05 (12H, m), 2 .07 (2H, m), 2.24 (2H, m), 2.63 (4H, t), 6.79 (1H, d), 6.85 (1H, t), 6.90 (4H, d), 7.02 (4H, s), 7.07 (1H, s), 7.22 (1H, s), 7.32 (4H, d), 7.58 (1H, d), 7. 65 (1H, s), 7.84 (1H, d), 7.89 (1H, s).

<Example 1>
(Synthesis of polymer compound 1)
After making the gas in reaction container into inert gas atmosphere, it synthesize | combines according to the method as described in compound 8 (1.6658g, 1.60mmol) and well-known literature (Tetrahedron Letters (2001), 42 (37), 6527-6530). The following formula:

で示される化合物９（０．９９５０ｇ、１．９９ｍｍｏｌ）、特開２００８−１０６２４１号公報に記載の方法に従って合成した下記式：

Embedded image Compound 9 (0.9950 g, 1.99 mmol) represented by the following formula synthesized according to the method described in JP-A-2008-106241:

で示される化合物１０（０．１０６４ｇ、０．２０ｍｍｏｌ）、特開２００８−２１５８８６号公報に記載の方法に従って合成した下記式：

Compound 10 (0.1064 g, 0.20 mmol) represented by the following formula synthesized according to the method described in JP-A-2008-215886:

で示される化合物１１（０．０９２４ｇ、０．２０ｍｍｏｌ）、ジクロロビス（トリス−o‐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（４７ｍｌ）を混合し、１０５℃に加熱した。

Embedded image Compound 11 (0.0924 g, 0.20 mmol), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.8 mg) and toluene (47 ml) were mixed and heated to 105 ° C.

  A 20 wt% tetraethylammonium hydroxide aqueous solution (6.6 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 6 hours. After the reaction, phenylboronic acid (24.4 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.8 mg) were added thereto, and the mixture was further refluxed for 14 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting mixture was cooled, washed twice with water (26 ml), twice with 3 wt% aqueous acetic acid (26 ml) and twice with water (26 ml), and the resulting solution was added dropwise to methanol (310 mL). A precipitate was obtained by filtration.

This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.71 g of polymer compound 1. The polymer compound 1 had a polystyrene-equivalent number average molecular weight of 2.0 × 10 ⁵ and a polystyrene-equivalent weight average molecular weight of 5.2 × 10 ⁵ .

  The polymer compound 1 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、５０：４０：５：５のモル比で構成されてなる共重合体である。

Is a copolymer composed of a molar ratio of 50: 40: 5: 5.

<Comparative Example 1>
(Synthesis of polymer compound 2)
After making the gas in the reaction vessel an inert gas atmosphere, Compound 9 (0.9950 g, 1.99 mmol), Compound 10 (0.1064 g, 0.20 mmol), Compound 11 (0.0924 g, 0.20 mmol), The following formula synthesized according to the method described in JP-T-2002-506481:

で示される化合物１２（０．７３６４ｇ、１．６０ｍｍｏｌ）、ジクロロビス（トリス−o‐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（４７ｍｌ）を混合し、１０５℃に加熱した。

Embedded image Compound 12 (0.7364 g, 1.60 mmol), dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.8 mg) and toluene (47 ml) were mixed and heated to 105 ° C.

  A 20 wt% tetraethylammonium hydroxide aqueous solution (6.6 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 5.5 hours. After the reaction, phenylboronic acid (24.4 mg) and dichlorobis (tris-o-methoxyphenylphosphine) palladium (1.8 mg) were added thereto, and the mixture was further refluxed for 14 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting mixture was cooled, washed twice with water (26 ml), twice with 3 wt% aqueous acetic acid (26 ml) and twice with water (26 ml), and the resulting solution was added dropwise to methanol (310 mL). A precipitate was obtained by filtration.

This precipitate was dissolved in toluene (63 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (310 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 0.91 g of polymer compound 2. The number average molecular weight in terms of polystyrene of the polymer compound 2 was 5.2 × 10 ⁴ , and the weight average molecular weight in terms of polystyrene was 2.5 × 10 ⁵ .

  The polymer compound 2 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位とが、５０：４０：５：５のモル比で構成されてなる共重合体である。

Is a copolymer composed of a molar ratio of 50: 40: 5: 5.

<Synthesis Example 8>
(Synthesis of polymer compound 3)
After making the gas in the reaction vessel an inert gas atmosphere, the following formula synthesized according to the method described in JP 2011-174061 A:

で示される化合物１３（２．８９６４ｇ、３．９２ｍｍｏｌ）、下記式：

Compound 13 (2.8964 g, 3.92 mmol) represented by the following formula:

で示される化合物１４（１．９７４４ｇ、３．６０ｍｍｏｌ）、特開２００４−１４３４１９号公報に記載の方法に従って合成した下記式：

Compound 14 (1.9744 g, 3.60 mmol) represented by the following formula synthesized according to the method described in JP-A No. 2004-143419:

で示される化合物１５（０．２９６３ｇ、０．４０ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（２．８ｍｇ）およびトルエン（４０ｍｌ）を混合し、１０５℃に加熱した。

Embedded image Compound 15 (0.2963 g, 0.40 mmol), dichlorobis (triphenylphosphine) palladium (2.8 mg) and toluene (40 ml) were mixed and heated to 105 ° C.

  Methyl trioctyl ammonium chloride (trade name: Aliquat (registered trademark) 336, manufactured by Aldrich) (0.517 g), 17.5 wt% aqueous sodium carbonate solution (10.9 ml) was added dropwise to the resulting reaction solution, Refluxed for 3 hours. After the reaction, phenylboronic acid (50.0 mg) and dichlorobis (triphenylphosphine) palladium (2.8 mg) were added thereto, and the mixture was further refluxed for 17 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. The resulting mixture was cooled, washed twice with water (52 ml), twice with 3 wt% aqueous acetic acid (52 ml) and twice with water (52 ml), and the resulting solution was added dropwise to methanol (620 mL). A precipitate was obtained by filtration.

This precipitate was dissolved in toluene (120 mL) and purified by passing through an alumina column and a silica gel column in this order. The obtained solution was added dropwise to methanol (620 ml) and stirred, and then the obtained precipitate was collected by filtration and dried to obtain 2.00 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 2.8 × 10 ⁵ .

  The polymer compound 3 has the following formula:

で示される構成単位と、下記式：

And the following formula:

で示される構成単位と、下記式：

And the following formula:

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

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

<Example D1: Production and evaluation of light-emitting element D1>
A glass substrate with an ITO film having a thickness of 45 nm formed by sputtering is spin-coated using AQ-1200 (manufactured by Plextronics), which is a polythiophene-sulfonic acid-based hole injection agent, as a hole injection material. A hole injection layer was formed by forming a film with a thickness and heating it at 170 ° C. for 15 minutes in an air atmosphere on a hot plate.

  Next, the polymer compound 1 was dissolved in xylene to prepare a 0.7% by mass xylene solution. A film having a thickness of 20 nm was formed by spin coating using this xylene solution, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere to form a hole transport layer.

  Next, the polymer compound 3 was dissolved in xylene to prepare a 1.3% by mass xylene solution. A film having a thickness of 60 nm was formed by spin coating using this xylene solution, and a light emitting layer was formed by heating at 150 ° C. for 10 minutes on a hot plate in a nitrogen gas atmosphere.

Next, 7 nm of sodium fluoride and then 120 nm of aluminum were vapor-deposited as a cathode, and the light emitting element D1 was produced. In addition, after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, metal deposition was started.

The light-emitting element D1 obtained above was driven with a constant current after setting the current value so that the initial luminance was 2500 cd / m ^2, and the change in light emission luminance with time was measured. As a result, the luminance was reduced by half after 92 hours. The results are shown in Table 1.

<Comparative Example CD1: Production and Evaluation of Light-Emitting Element CD1>
A light emitting device CD1 was produced in the same manner as in Example D1, except that the polymer compound 2 was used in place of the polymer compound 1 of Example D1.

The light-emitting element CD1 obtained above was set with a current value so that the initial luminance was 2500 cd / m ^2, and then was driven with a constant current, and the change in light emission luminance with time was measured. As a result, the emission luminance was reduced by half after 2.7 hours. The results are shown in Table 1.

  From the results of Table 1 above, it was found that the light-emitting device produced using the polymer compound of the present invention has an excellent luminance life.

Claims (15)

A structural unit represented by the following formula (1-1);
A polymer compound comprising a structural unit represented by the following formula (2) and / or a structural unit represented by the following formula (2 ′).

[Where:
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, unsubstituted or substituted An alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic group.
R ¹ and R ³ may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ² and R ⁴ are connected to each other to form a ring structure with the carbon atoms to which they are bonded. R ¹ and R ² may be connected to each other to form a ring structure with the carbon atoms to which they are bonded, and R ³ and R ⁴ are connected to each other to bond to each other. A ring structure may be formed together with atoms, and adjacent groups among R ⁷ , R ⁸ and R ⁹ may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded.
R ^A and R ^B each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ¹ and Ar ² each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹ and R ^A may be connected to each other to form a ring structure with the nitrogen atom to which Ar ¹ and R ^A are bonded, and Ar ² and R ^B are connected to each other to form a ring structure with the nitrogen atom to which each is bonded. You may do it.
Y represents —C (R ^a ) ₂ —, —N (R ^a ) —, —O— or —S—.
R ^a represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, or an unsubstituted or substituted monovalent heterocyclic ring. Indicates a group. When ^a plurality of R ^a are present, they may be the same or different, and may be connected to each other to form a ring structure together with the carbon atoms to which they are bonded. ]

[Where:
na represents an integer of 0 to 3, nb represents an integer of 0 to 12, nA represents 0 or 1, and n represents 1 or 2.
Ar ³ represents an unsubstituted or substituted (2 + n) -valent aromatic hydrocarbon 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 a plurality of X ′ are present, they may be the same or different. ]

[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).
Ar ²⁰ , Ar ³⁰ and Ar ⁴⁰ 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.
X ′ has 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 (2 ′) is different from the structural unit represented by the formula (1). ] The polymer compound according to claim 1, wherein the structural unit represented by the formula (1-1) is a structural unit represented by the following formula (1-1-A).

[Where:
Y, R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ^A , R ^B , Ar ¹ and Ar ² are as defined above.
n ¹ and ^{n 2} each independently represent an integer of 1 to 5.
R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each independently a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryl An oxy group or an unsubstituted or substituted monovalent heterocyclic group is shown.
When there are a plurality of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ , they may be the same or different, and adjacent groups of R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are linked to each other. And may form a ring structure together with the carbon atoms to which they are bonded. ] The polymer compound according to claim 2, wherein the structural unit represented by the formula (1-1-A) is a structural unit represented by the following formula (1-1-B).

[Where:
n ¹ , n ² , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ^A , R ^B , Ar ¹ and Ar ² are It is synonymous with.
R ¹⁵ and R ¹⁶ each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or A substituted monovalent heterocyclic group is shown.
R ¹⁵ and R ¹⁶ may be connected to each other to form a ring structure together with the carbon atom to which each is bonded. ] The high molecular compound according to any one of claims 1 to 3, wherein X 'is a monovalent crosslinkable group represented by the following formula (X'-1).

[Wherein, benzocyclobutane may have a substituent. ] The polymer compound according to claim 1, wherein X ′ is a monovalent crosslinkable group represented by the following formula (X′-2).

[Where:
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 ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ and R ²¹ 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. ] Furthermore, the high molecular compound as described in any one of Claims 1-5 containing the structural unit shown by following formula (3).

[Where:
Ar ⁴ represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
However, the structural unit represented by the formula (3) is different from the structural unit represented by the formula (2). ]   The polymer compound according to claim 6, wherein at least one of the structural units represented by the formula (3) is a structural unit composed of an unsubstituted or substituted phenylenediyl group.   The polymer compound according to claim 7, wherein at least one of the structural units represented by the formula (3) is a structural unit composed of an unsubstituted or substituted fluorenediyl group. Furthermore, the high molecular compound as described in any one of Claims 1-8 containing the structural unit shown by following formula (4).

[Where:
a ¹ and a ² each independently represent 0 or 1.
Ar ⁵ and Ar ⁷ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ⁶ and Ar ⁸ 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 ^C , R ^D and R ^E each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Ar ⁵ , Ar ⁶ , Ar ⁷ and Ar ⁸ 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 (4) is different from the structural unit represented by the formula (1) and the structural unit represented by the formula (2 ′). ] The polymer compound according to claim 9, wherein at least one of the structural units represented by the formula (4) is a structural unit represented by the following formula (5).

[Where:
R ^F represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
Z represents a single bond, an oxygen atom, a sulfur atom or —C (R ^b ) ₂ —. R ^b represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. Two R ^{b s} may be the same or different, and may form a ring structure together with the carbon atom to which each R ^b is bonded. ] The total content of the structural unit represented by the formula (1-1) is, relative to the total content of the structural units contained in the polymer compound, 20 to 60 mol%, more of claims 1 to 1 0 The polymer compound according to claim 1. The polymer compound according to any one of claims 1 to 11,
A composition containing at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.   The organic thin film containing the high molecular compound as described in any one of Claims 1-11.   An insolubilized organic thin film containing the polymer compound according to claim 13.   A light emitting device comprising the organic thin film according to claim 13 or the insolubilized material according to claim 14.