JP5958045B2 - Polymer compound and light emitting device using the same - Google Patents

Description

  The present invention relates to a polymer compound, a raw material compound of the polymer compound and a production method thereof, a composition containing the polymer compound, an organic thin film, and a light emitting device.

  As a light-emitting material used for manufacturing a light-emitting element, for example, a polymer compound containing a structural unit derived from arylamine (Patent Document 1) is known.

JP 2004-143419 A

  However, a light emitting device manufactured using the above polymer compound does not necessarily have sufficient light emission efficiency.

  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 luminous efficiency. Another object of the present invention is to provide a composition containing a polymer compound, an organic thin film, and a light emitting device. It is another object of the present invention to provide a raw material compound for a polymer compound and a method for producing the same.

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

（式（１）中、
Ar^aおよびAr^ｂは、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表し、
Ar^ｃは、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
Ar^aおよびAr^bからなる群から選ばれる少なくともひとつが無置換もしくは置換のフェナントレンジイル基を表す。
Ar^ｄは、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基または無置換もしくは置換のアルキル基を表す。２個存在するAr^ｄは、同一であっても異なっていてもよい。）
［２］ 前記式（１）で表される構成単位が、下記式（１−２）で表される構造単位である、［１］に記載の高分子化合物。

（式（１−２）中、
R^a、R^bおよびR^ｃは、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R^a、R^bおよびR^ｃが複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
Ar^ｃおよびAr^ｄは、前記と同じ意味を表す。
hおよびjは、それぞれ独立に、０〜4の整数を表し、iは、０〜２の整数を表す。２個存在するｈ、ｉおよびｊは、それぞれ、同一であっても異なっていてもよい。）
［３］ 前記式（１−２）で表される構成単位が、下記式（１−２−１）で表される構成単位である、［２］に記載の高分子化合物。

（式（１−２−１）中、
Ar^ｃ、Ar^ｄ、R^a、R^b、R^ｃおよびｉは、前記と同じ意味を表す。
kおよびlは、それぞれ独立に、０〜3の整数を表す。）
［４］ 前記Ar^ｃが、無置換もしくは置換のフェニレン基または無置換もしくは置換のビフェニルジイル基である、［１］〜［３］のいずれか一つに記載の高分子化合物。
［５］ 前記Ar^ｄが、無置換もしくは置換のフェニル基である、［１］〜［４］のいずれか一つに記載の高分子化合物。
［６］ 更に、下記式（３）で表される構成単位および下記式（４）で表される構成単位からなる群から選ばれる少なくとも一種類の構成単位を含む、［１］〜［５］のいずれか一つに記載の高分子化合物。

（式（３）中、
Ar⁵は、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基または金属錯体構造を有する二価の基を表す。）
（式（４）中、
Ar⁶は、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表し、
Ar^７およびAr⁸は、それぞれ独立に、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
２個存在するAr⁶は、同一であっても異なっていてもよい。
Ｅ_１、Ｅ_２およびＥ_３は、それぞれ独立に、水素原子、無置換もしくは置換アルキル基、無置換もしくは置換アリール基または無置換もしくは置換の一価の複素環基を表す。
aおよびｐは、それぞれ独立に、０または１を表し、０≦a＋ｐ≦１である。
Ａｒ^６、Ａｒ^７、Ａｒ^８およびＡｒ^９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、単結合、―O―、―CR¹R²―または―S―で渡環されていてもよい。R¹およびR²は、それぞれ独立に、水素原子、無置換もしくは置換アルキル基または無置換もしくは置換アリール基を表す。）
［７］ 前記式（３）で表される構成単位が、下記式(３−１)で表される構成単位または下記式（３−２）で表される構成単位である、［６］に記載の高分子化合物。

（式（３−１）中、
R³およびR⁴は、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R³およびR⁴が複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
bおよびｃは、それぞれ独立に、０〜３の整数を表す。
R⁵およびR⁶は、それぞれ独立に、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。）

（式（３−２）中、
R^７は、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R^７が複数存在する場合、それらは同一であっても異なっていてもよい。
dは、０〜４の整数を表す。）
［８］ 前記式（４）で表される構成単位が、下記式(４−１)で表される構造単位または下記式（４−２）で表される構造単位である、［６］または［７］に記載の高分子化合物。

（式（４−１）中、
Qは単結合、―O―、―C（R¹）（R²）―、―S―を表し、R¹およびR²は、前記と同じ意味を表す。
Ar¹⁴は、水素原子、無置換もしくは置換のアルキル基、無置換もしくは置換のアリールアルキル基、無置換もしくは置換のアリール基または無置換もしくは置換の一価の複素環基を表す。
R⁸およびR⁹は、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R⁸およびR⁹が複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
ｅおよびfは、それぞれ独立に、０〜３の整数である。）

（式（４−２）中、
Ａｒ^１３は、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表す。
R^１０およびR^１１は、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基、または無置換もしくは置換のアルキル基を表す。R^１０およびR^１１が複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
gは、０〜４の整数を表し、mは、０〜５の整数を表し、nは、０または１を表す。２個存在するｇおよびｍは、それぞれ同一であっても異なっていてもよい。）
［９］ 前記式（３）で表される構造単位が、下記式（９）で表される構成単位である、［６］〜［８］のいずれか一つに記載の高分子化合物。

（式（９）中、
Ar^１０およびAr^１１は、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表す。
Ar^１２は、水素原子、無置換もしくは置換のアリール基または無置換もしくは置換の一価の複素環基を表す。）
［１０］ 更に、下記式（３−３）で表される構成単位（前記式（３）で表される構成単位および前記式（３−１）で表される構成単位とは異なる。）および下記式（４−３）で表される構成単位（前記式（４）で表される構成単位および前記式（４−２）で表される構成単位とは異なる。）からなる群から選ばれる少なくとも１種類の構成単位を含む、［１］〜［９］のいずれか一項に記載の高分子化合物。

（式（３−３）中、
Ｒ^２１は、架橋性基を表す。
Ｒ^２２は、水素原子、架橋性基、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基または非置換若しくは置換の一価の複素環基を表す。）
（式（４−３）中、
Ｒ^２３は、架橋性基を表す。
Ｒ^２４は、架橋性基、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基または非置換若しくは置換の一価の複素環基を表す。
ｑは、０または１を表す。）
［１１］ 前記式（１）で表される構成単位の含有量が、
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、
０．１モル％以上５０モル％以下である、［１］〜［１０］のいずれか一つに記載の高分子化合物。
［１２］ 下記式（５）で表される化合物。

（式中、
LGは、ハロゲン原子（但し、フッ素原子は除く。）、−Ｂ（ＯＨ）_２、−ＢＦ_４ ⁻Ｑ（Ｑはリチウム、ナトリウム、カリウム、ルビジウムまたはセシウムの一価の陽イオンを示す。）で表される基、ボロン酸エステル残基、または、―O―SO₂―Zで表される基を表す。Zは、無置換もしくは置換のアルキル基またはアリール基を表す。２個存在するLGは、同一であっても異なっていてもよい。
Ar^aおよびAr^ｂは、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表し、
Ar^ｃは、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
Ar^aおよびAr^bからなる群から選ばれる少なくともひとつが無置換もしくは置換のフェナントレンジイル基を表す。
Ar^ｄは、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基または無置換もしくは置換のアルキル基を表す。２個存在するAr^ｄは、同一であっても異なっていてもよい。）
［１３］ ［１２］に記載の化合物を重合する工程を含み、かつ、遷移金属化合物を触媒として使用する、高分子化合物の製造方法。
［１４］ 下記式（６）で表される化合物と下記式（７）で表される化合物と、を反応させる工程を含む、下記式（８）で表される化合物の製造方法。

（式（６）中、
Ar^ｅは、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表す。
LGは、ハロゲン原子（但し、フッ素原子は除く。）、−Ｂ（ＯＨ）_２、−ＢＦ_４ ⁻Ｑ（Ｑはリチウム、ナトリウム、カリウム、ルビジウムまたはセシウムの一価の陽イオンを示す。）で表される基、ボロン酸エステル残基、または、―O―SO₂―Zで表される基を表す。Zは、無置換もしくは置換のアルキル基またはアリール基を表す。２個存在するLGは、同一であっても異なっていてもよい。）
（式（７）中、
Ar^ｃは、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
Ar^ｄは、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基または無置換もしくは置換のアルキル基を表す。２個存在するAr^ｄは、同一であっても異なっていてもよい。）
（式（８）中、
Ar^ｃ、Ar^ｄ、Ar^ｅおよびLGは、前記と同じ意味を表す。２個存在するAr^ｄ、Ar^ｅおよびLGはそれぞれ、同一であっても異なっていてもよい。
但し、２個存在するAr^eの少なくともひとつは、無置換もしくは置換のフェナントレンジイル基を表す。）
［１５］ ［１］〜［１１］のいずれか一つに記載の高分子化合物と、
正孔輸送材料、電子輸送材料および発光材料からなる群から選ばれる少なくとも一種類の材料と、を含有する組成物。
［１６］ ［１］〜［１１］のいずれか一つに記載の高分子化合物と、溶媒と、を含有する液状組成物。
［１７］ ［１］〜［１１］のいずれか一つに記載の高分子化合物を含有する有機薄膜。
［１８］ 陽極および陰極からなる電極と、該電極間に設けられた有機層と、を含む発光素子であって、
該有機層が、［１］〜［１１］のいずれか一つに記載の高分子化合物を含有する、発光素子。
［１９］ 前記有機層が、発光層または電荷輸送層である、［１８］に記載の発光素子。 [1] A polymer compound containing a structural unit represented by the following formula (1).

(In the formula (1),
Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group;
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
At least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )
[2] The polymer compound according to [1], wherein the structural unit represented by the formula (1) is a structural unit represented by the following formula (1-2).

(In the formula (1-2),
R ^a , R ^b and R ^c are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. When there are a plurality of R ^a , R ^b and R ^c , they may be the same or different.
Ar ^c and Ar ^d have the same meaning as described above.
h and j each independently represents an integer of 0 to 4, and i represents an integer of 0 to 2. Two h, i, and j may be the same or different. )
[3] The polymer compound according to [2], wherein the structural unit represented by the formula (1-2) is a structural unit represented by the following formula (1-2-1).

(In the formula (1-2-1),
Ar ^c , Ar ^d , R ^a , R ^b , R ^c and i represent the same meaning as described above.
k and l each independently represents an integer of 0 to 3. )
[4] the Ar ^c is an unsubstituted or substituted phenylene group or an unsubstituted or substituted biphenyl-diyl group, [1] - The polymer compound according to any one of [3].
[5] The polymer compound according to any one of [1] to [4], wherein Ar ^d is an unsubstituted or substituted phenyl group.
[6] Furthermore, it contains at least one kind of structural unit selected from the group consisting of a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4). The high molecular compound as described in any one of these.

(In formula (3),
Ar ⁵ represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or a divalent group having a metal complex structure. )
(In formula (4),
Ar ⁶ each independently represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group,
Ar ⁷ and Ar ⁸ are each independently an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent complex. Represents a divalent group in which two or more groups selected from the group consisting of cyclic groups are linked;
Two Ar ⁶ may be the same or different.
E ₁ , E ₂ and E ₃ 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.
a and p each independently represent 0 or 1, and 0 ≦ a + p ≦ 1.
Ar ⁶ , Ar ⁷ , Ar ⁸ and Ar ⁹ are each a group other than the group bonded to the nitrogen atom to which the group is bonded, a single bond, —O—, —CR ¹ R ² — or — It may be passed by S-. R ¹ and R ² each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. )
[7] The structural unit represented by the formula (3) is a structural unit represented by the following formula (3-1) or a structural unit represented by the following formula (3-2). The polymer compound described.

(In Formula (3-1),
R ³ and R ⁴ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or unsubstituted Alternatively, it represents a substituted alkyl group. When a plurality of R ³ and R ⁴ are present, they may be the same or different.
b and c each independently represent an integer of 0 to 3.
R ⁵ and R ⁶ are each independently a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. )

(In the formula (3-2),
R ⁷ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted alkyl group. . When a plurality of R ⁷ are present, they may be the same or different.
d represents an integer of 0 to 4. )
[8] The structural unit represented by the formula (4) is a structural unit represented by the following formula (4-1) or a structural unit represented by the following formula (4-2), [6] or [7] The polymer compound according to [7].

(In the formula (4-1),
Q represents a single bond, —O—, —C (R ¹ ) (R ² ) —, —S—, and R ¹ and R ² represent the same meaning as described above.
Ar ¹⁴ represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted arylalkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
R ⁸ and R ⁹ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or unsubstituted Alternatively, it represents a substituted alkyl group. When a plurality of R ⁸ and R ⁹ are present, they may be the same or different.
e and f are each independently an integer of 0 to 3. )

(In the formula (4-2),
Ar ¹³ is selected from the group consisting of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group Represents a divalent group in which two or more groups are linked.
R ¹⁰ and R ¹¹ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or Represents a substituted or substituted alkyl group. When a plurality of R ¹⁰ and R ¹¹ are present, they may be the same or different.
g represents an integer of 0 to 4, m represents an integer of 0 to 5, and n represents 0 or 1. Two of g and m may be the same or different. )
[9] The polymer compound according to any one of [6] to [8], wherein the structural unit represented by the formula (3) is a structural unit represented by the following formula (9).

(In Formula (9),
Ar ¹⁰ and Ar ¹¹ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹² represents a hydrogen atom, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group. )
[10] Furthermore, a structural unit represented by the following formula (3-3) (different from the structural unit represented by the formula (3) and the structural unit represented by the formula (3-1)) and It is selected from the group consisting of the structural unit represented by the following formula (4-3) (different from the structural unit represented by the formula (4) and the structural unit represented by the formula (4-2)). The polymer compound according to any one of [1] to [9], comprising at least one type of structural unit.

(In Formula (3-3),
R ²¹ represents a crosslinkable group.
R ²² represents a hydrogen atom, a crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group. )
(In Formula (4-3),
R ²³ represents a crosslinkable group.
R ²⁴ represents a crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
q represents 0 or 1; )
[11] The content of the structural unit represented by the formula (1) is
For the total content of structural units contained in the polymer compound,
The polymer compound according to any one of [1] to [10], which is 0.1 mol% or more and 50 mol% or less.
[12] A compound represented by the following formula (5).

(Where
LG is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - with Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) And a group represented by a boronic acid ester residue or —O—SO ₂ —Z. Z represents an unsubstituted or substituted alkyl group or aryl group. Two LGs may be the same or different.
Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group;
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
At least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )
[13] A method for producing a polymer compound, comprising a step of polymerizing the compound according to [12], and using a transition metal compound as a catalyst.
[14] A method for producing a compound represented by the following formula (8), comprising a step of reacting a compound represented by the following formula (6) and a compound represented by the following formula (7).

(In Formula (6),
Ar ^e represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
LG is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - with Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) And a group represented by a boronic acid ester residue or —O—SO ₂ —Z. Z represents an unsubstituted or substituted alkyl group or aryl group. Two LGs may be the same or different. )
(In formula (7),
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )
(In Formula (8),
Ar ^c , Ar ^d , Ar ^e and LG have the same meaning as described above. Two Ar ^d , Ar ^e and LG may be the same or different.
However, at least one of the two existing Ar ^e represents an unsubstituted or substituted phenanthrene diyl group. )
[15] 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.
[16] A liquid composition comprising the polymer compound according to any one of [1] to [11] and a solvent.
[17] An organic thin film containing the polymer compound according to any one of [1] to [11].
[18] A light emitting device comprising an electrode composed of an anode and a cathode, and an organic layer provided between the electrodes,
The light emitting element in which this organic layer contains the high molecular compound as described in any one of [1]-[11].
[19] The light emitting device according to [18], wherein the organic layer is a light emitting layer or a charge transport layer.

  ADVANTAGE OF THE INVENTION According to this invention, the high molecular compound useful for manufacture of the light emitting element which is excellent in luminous efficiency can be provided. Moreover, according to this invention, the composition, organic thin film, and light emitting element containing a high molecular compound can be provided. Furthermore, according to this invention, the raw material compound of a high molecular compound and its manufacturing method can be provided.

  Hereinafter, a preferred embodiment of the present invention will be described in detail. In the present specification, Me represents a methyl group, Et represents an ethyl group, i-Pr represents an isopropyl group, n-Bu represents a normal butyl group, and t-Bu and tBu represent a tert-butyl group. And Ph represents a phenyl group. THF represents tetrahydrofuran.

  In the present specification, the “structural unit” means a unit structure present 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).

  In the present specification, the “n-valent heterocyclic group” (n is 1 or 2) is a carbon atom constituting a ring from a heterocyclic compound (preferably a heterocyclic compound having aromaticity). Means a group formed by removing n hydrogen atoms directly bonded to. Here, the heterocyclic compound is an organic compound having a cyclic structure, and the elements constituting the ring include not only carbon atoms but also heteroatoms such as oxygen, sulfur, nitrogen, phosphorus and boron in the ring. Means a compound.

  In the present specification, the “arylene group” means an atomic group obtained by 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. The carbon number of the arylene group is usually 6 to 60 without including the carbon number of the substituent unless otherwise specified in each description in the present specification.

  In the present specification, the “aryl group” means an atomic group formed by removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon, and includes those having a condensed ring. The carbon number of the aryl group is usually 6 to 60 without including the carbon number of the substituent unless otherwise specified in each description in the present specification.

  In the present specification, the “transition metal compound” means a catalyst used for production of a polymer compound. The transition metal compound includes a transition metal complex having an organic ligand and a transition metal complex having no organic ligand supported on a carrier.

<Structural Unit Represented by Formula (1)>
The high molecular compound of this invention contains the structural unit represented by Formula (1). The structural unit represented by Formula (1) may be contained alone or in combination of two or more.

In the formula (1), Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group, and Ar ^c represents an unsubstituted or substituted arylene group. , An unsubstituted or substituted divalent heterocyclic group, or a divalent group in which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group are linked And at least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^a and Ar ^b are preferably an unsubstituted or substituted arylene group, and Ar ^c is preferably an unsubstituted or substituted arylene group, or two or more selected from the group consisting of an unsubstituted or substituted arylene group Is a divalent group linked, more preferably at least one selected from the group consisting of Ar ^a and Ar ^b is an unsubstituted or substituted phenanthrene diyl group, more preferably Ar ^a and Ar ^b Both are unsubstituted or substituted phenanthrene diyl groups.

The carbon number of the unsubstituted or substituted arylene group represented by Ar ^a , Ar ^b and Ar ^c does not include the carbon number of the substituent, and is usually 6 to 60, preferably 6 to 30, more preferably It is 6-18, More preferably, it is 6-14.

The arylene group represented by Ar ^a , Ar ^b and Ar ^c may have an unsubstituted or substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkylthio group, an unsubstituted or substituted group An aryl group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted arylthio group, an unsubstituted or substituted amino group, an unsubstituted or substituted silyl group, a halogen atom, an acyl group, an unsubstituted or substituted acyloxy group, Examples thereof include an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted carboxyl group, a cyano group and a nitro group.

As the substituent that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have, the stability of the polymer compound according to the present embodiment is improved, and the luminous efficiency of the light-emitting device using the polymer compound Is preferably 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, or a cyano group. Or a substituted alkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substituted aryloxy group is more preferred, and an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group is Further preferred.

The alkyl group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “alkyl group” in the present specification are straight-chain unless otherwise specified in each description in the present specification. , Branched or cyclic, and may have a substituent.
The alkyl group usually has 1 to 20 carbon atoms (in the case of a branched alkyl group and a cyclic alkyl group, usually 3 to 20), not including the carbon number of the substituent, for example, methyl group, ethyl group, propyl Group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, Examples include a lauryl group, a trifluoromethyl group, a pentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl group, and a perfluorooctyl group.

The alkoxy group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “alkoxy group” in this specification are linear unless otherwise specified in each description in the present specification. , Branched or cyclic, and may have a substituent.
The alkoxy group usually has 1 to 20 carbon atoms (in the case of a branched alkoxy group and a cyclic alkoxy group, usually 3 to 20), not including the carbon number of the substituent, for example, methoxy group, ethoxy group, propyl Oxy group, isopropyloxy group, butoxy group, isobutoxy group, t-butoxy group, pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, trifluoromethoxy group, pentafluoroethoxy group, perfluorobutoxy group, perfluorohexyloxy group, perfluorooctyloxy group, methoxymethyloxy group, 2-methoxyethyloxy Groups.

The alkylthio group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “alkylthio group” in this specification are straight-chain unless otherwise specified in each description in this specification. , Branched or cyclic, and may have a substituent.
The alkylthio group usually has 1 to 20 carbon atoms (in the case of a branched alkylthio group and a cyclic alkylthio group, usually 3 to 20), not including the carbon number of the substituent, for example, methylthio group, ethylthio group, propylthio group. Group, isopropylthio group, butylthio group, isobutylthio group, t-butylthio group, pentylthio group, hexylthio group, cyclohexylthio group, heptylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, 3,7- Examples thereof include a dimethyloctylthio group, a laurylthio group, and a trifluoromethylthio group.

An aryl group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “aryl group” in this specification are substituents unless otherwise specified in each description in this specification. You may have.
The aryl group usually has 6 to 60 carbon atoms, preferably 7 to 48, not including the carbon number of the substituent, and is, for example, a phenyl group, a C _{1 to} C ₁₂ alkoxyphenyl group (“C ₁ to C “C ₁₂ alkoxy” indicates that the alkoxy moiety has 1 to 12 carbon atoms. The same applies hereinafter.), A C _{1 to} C ₁₂ alkylphenyl group (“C _{1 to} C ₁₂ alkyl” is a carbon atom in the alkyl moiety. The number is 1 to 12. The same applies hereinafter.), 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, pentafluorophenyl group. is, C ₁ -C ₁₂ alkoxyphenyl group, is C ₁ -C ₁₂ alkylphenyl group are preferable.
The C ₁ -C ₁₂ alkoxyphenyl group, methoxyphenyl group, ethoxyphenyl group, propyloxyphenyl group, isopropyloxyphenyl group, butoxyphenyl group, isobutoxyphenyl group, tert- butoxyphenyl, pentyloxyphenyl group, hexyl Oxyphenyl group, cyclohexyloxyphenyl group, heptyloxyphenyl group, octyloxyphenyl group, 2-ethylhexyloxyphenyl group, nonyloxyphenyl group, decyloxyphenyl group, 3,7-dimethyloctyloxyphenyl group, lauryloxyphenyl group Etc.
The C ₁ -C ₁₂ alkylphenyl group include a methylphenyl group, ethylphenyl group, dimethylphenyl group, propylphenyl group, mesityl group, methylethylphenyl group, isopropylphenyl group, butylphenyl group, isobutylphenyl group, tert- butyl Examples thereof include a phenyl group, a pentylphenyl group, an isoamylphenyl group, a hexylphenyl group, a heptylphenyl group, an octylphenyl group, a nonylphenyl group, a decylphenyl group, and a dodecylphenyl group.

The aryloxy group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “aryloxy group” in the present specification, unless otherwise specified in each description in the present specification, It may have a substituent.
The aryloxy group usually has 6 to 60 carbon atoms, preferably 7 to 48, not including the carbon number of the substituent, such as phenoxy group, C _{1 to} C ₁₂ alkoxyphenoxy group, C ₁ to C ₁₂ alkylphenoxy groups, 1-naphthyloxy group, 2-naphthyloxy group, and a pentafluorophenyl group, C ₁ -C ₁₂ alkoxy phenoxy group, a C ₁ -C ₁₂ alkylphenoxy group are preferable.
Examples of the C ₁ -C ₁₂ alkoxyphenoxy group include methoxyphenoxy group, ethoxyphenoxy group, propyloxyphenoxy group, isopropyloxyphenoxy group, butoxyphenoxy group, isobutoxyphenoxy group, tert-butoxyphenoxy group, pentyloxyphenoxy group, hexyl Oxyphenoxy group, cyclohexyloxyphenoxy group, heptyloxyphenoxy group, octyloxyphenoxy group, 2-ethylhexyloxyphenoxy group, nonyloxyphenoxy group, decyloxyphenoxy group, 3,7-dimethyloctyloxyphenoxy group, lauryloxyphenoxy group Etc.
The C ₁ -C ₁₂ alkylphenoxy group, methylphenoxy group, ethylphenoxy group, dimethylphenoxy group, propylphenoxy group, 1,3,5-methylphenoxy group, methylethylphenoxy group, isopropylphenoxy group, butylphenoxy group, Examples thereof include isobutylphenoxy group, tert-butylphenoxy group, pentylphenoxy group, isoamylphenoxy group, hexylphenoxy group, heptylphenoxy group, octylphenoxy group, nonylphenoxy group, decylphenoxy group, dodecylphenoxy group and the like.

The arylthio group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “arylthio group” in the present specification are the substituents unless otherwise specified in each description in the present specification. You may have.
The arylthio group usually has 6 to 60 carbon atoms, not including the carbon number of the substituent, such as a phenylthio group, a C _{1 to} C ₁₂ alkoxyphenylthio group, a C _{1 to} C ₁₂ alkylphenylthio group, 1 -A naphthylthio group, 2-naphthylthio group, pentafluorophenylthio group is mentioned.

The arylalkyl group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “arylalkyl group” in the present specification, unless otherwise specified in each description in the present specification, It may have a substituent.
The arylalkyl group usually has 7 to 60 carbon atoms, not including the carbon number of the substituent, and examples thereof include a phenyl-C _{1 to} C ₁₂ alkyl group and a C _{1 to} C ₁₂ alkoxyphenyl-C _{1 to} C _12. alkyl group, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkyl group, 1-naphthyl -C ₁ -C ₁₂ alkyl group, a 2-naphthyl -C ₁ -C ₁₂ alkyl group.

The arylalkoxy group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “arylalkoxy group” in the present specification, unless otherwise specified in each description in the present specification, It may have a substituent.
The arylalkoxy group usually has 7 to 60 carbon atoms, not including the carbon number of the substituent, and examples thereof include a phenyl-C _{1 to} C ₁₂ alkoxy group and a C _{1 to} C ₁₂ alkoxyphenyl-C _{1 to} C _12. alkoxy groups, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkoxy groups, 1-naphthyl -C ₁ -C ₁₂ alkoxy group, a 2-naphthyl -C ₁ -C ₁₂ alkoxy group.

The arylalkylthio group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “arylalkylthio group” in the present specification, unless otherwise specified in each description in the present specification, It may have a substituent.
The arylalkylthio group usually has 7 to 60 carbon atoms, not including the carbon number of the substituent, and examples thereof include a phenyl-C _{1 to} C ₁₂ alkylthio group and a C _{1 to} C ₁₂ alkoxyphenyl-C _{1 to} C _12. alkylthio group, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkylthio group, 1-naphthyl -C ₁ -C ₁₂ alkylthio group, a 2-naphthyl -C ₁ -C ₁₂ alkylthio group.

The amino group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “amino group” in this specification are unsubstituted unless otherwise specified in each description in this specification. An amino group substituted with one or two groups selected from the group consisting of an alkyl group, an aryl group, an arylalkyl group, and a monovalent heterocyclic group (hereinafter referred to as “substituted amino group”) May be said.)
The substituted amino group generally has 1 to 60 carbon atoms, preferably 2 to 48 carbon atoms, such as a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, a propylamino group, a dipropylamino group, Isopropylamino group, diisopropylamino group, butylamino group, s-butylamino group, isobutylamino group, tert-butylamino group, pentylamino group, hexylamino group, cyclohexylamino group, heptylamino group, octylamino group, 2- Ethylhexylamino group, nonylamino group, decylamino group, 3,7-dimethyloctylamino group, laurylamino group, cyclopentylamino group, dicyclopentylamino group, dicyclohexylamino group, pyrrolidyl group, piperidyl group, ditrifluoromethylamino group, phenylamino Amino group, diphenylamino group, C ₁ -C ₁₂ alkoxyphenyl amino group, di (C ₁ -C ₁₂ alkoxyphenyl) amino group, di (C ₁ -C ₁₂ alkylphenyl) amino groups, 1-naphthylamino group, 2 - naphthylamino group, pentafluorophenylamino group, pyridylamino group, pyridazinylamino group, pyrimidylamino group, Pirajiruamino group, triazyl amino group, phenyl -C ₁ -C ₁₂ alkylamino group, C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkylamino group, C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkylamino group, di (C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkyl) amino group, di (C ₁ -C ₁₂ alkylphenyl -C ₁ -C ₁₂ alkyl) amino groups, 1-naphthyl -C ₁ -C ₁₂ alkylamino group, 2-naphthyl -C ₁ ~ It includes ₁₂ alkylamino group.

The silyl group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “silyl group” in this specification are unsubstituted unless otherwise specified in each description in this specification. The silyl group substituted with 1, 2 or 3 groups selected from the group consisting of alkyl groups, aryl groups, arylalkyl groups and monovalent heterocyclic groups (hereinafter referred to as “substituted silyl groups”). It may be referred to as “base”.
The substituted silyl group generally has 1 to 60 carbon atoms, preferably 3 to 48 carbon atoms, such as trimethylsilyl group, triethylsilyl group, tripropylsilyl group, tri-isopropylsilyl group, dimethyl-isopropylsilyl group, Diethyl-isopropylsilyl group, tert-butyldimethylsilyl group, pentyldimethylsilyl group, hexyldimethylsilyl group, heptyldimethylsilyl group, octyldimethylsilyl group, 2-ethylhexyl-dimethylsilyl group, nonyldimethylsilyl group, decyldimethylsilyl group , 3,7-dimethyl octyl - dimethylsilyl group, lauryldimethylsilyl group, a phenyl -C ₁ -C ₁₂ Akirushiriru group, C ₁ -C ₁₂ alkoxyphenyl -C ₁ -C ₁₂ alkylsilyl group, C ₁ -C ₁₂ alkyl phenyl -C ₁ -C ₁₂ alkyl Silyl group, 1-naphthyl -C ₁ -C ₁₂ alkylsilyl group, 2-naphthyl -C ₁ -C ₁₂ alkylsilyl group, a phenyl -C ₁ -C ₁₂ alkyldimethylsilyl group, triphenylsilyl group, tri -p- Examples include xylylsilyl group, tribenzylsilyl group, diphenylmethylsilyl group, t-butyldiphenylsilyl group, and dimethylphenylsilyl group.

As the halogen atom that the arylene group represented by Ar ^a , Ar ^b and Ar ^c may have as a substituent, and the “halogen atom” in the present specification, unless otherwise specified in each description in the present specification, for example, , Fluorine atom, chlorine atom, bromine atom and iodine atom, and fluorine atom is preferred.

The acyl group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “acyl group” in the present specification are the substituents unless otherwise specified in each description in the present specification. You may have.
The acyl group usually has 1 to 20 carbon atoms, preferably 2 to 18 carbon atoms not including the substituent, and is, for example, acetyl group, propionyl group, butyryl group, isobutyryl group, pivaloyl group, benzoyl group. Group, trifluoroacetyl group, and pentafluorobenzoyl group.

The acyloxy group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “acyloxy group” in the present specification are substituents unless otherwise specified in each description in the present specification. You may have.
The acyloxy group usually has 1 to 20 carbon atoms, preferably 2 to 18 carbon atoms not including the substituent carbon atoms, and examples thereof include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, Examples include a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.

The monovalent heterocyclic group that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have as a substituent, and the “monovalent heterocyclic group” in the present specification are each described in the description. Unless otherwise specified, may have a substituent.
The monovalent heterocyclic group usually has 2 to 60 carbon atoms, preferably 3 to 20 carbon atoms not including the carbon number of the substituent. Of the monovalent heterocyclic groups, monovalent aromatic heterocyclic groups are preferred. Examples of the monovalent heterocyclic group include thienyl group, C ₁ -C ₁₂ alkylthienyl group, pyrrolyl group, furyl group, pyridyl group, C ₁ -C ₁₂ alkylpyridyl group, piperidyl group, quinolyl group, and isoquinolyl group. the recited, a thienyl group, C ₁ -C ₁₂ alkyl thienyl group, a pyridyl group, a C ₁ -C ₁₂ alkyl pyridyl group are preferable.

The carboxyl group that the arylene group represented by Ar ^a , Ar ^b and Ar ^c may have as a substituent, and the “carboxyl group” in this specification are unsubstituted unless otherwise specified in each description in this specification. Even a carboxyl group substituted with an alkyl group, an aryl group, an arylalkyl group or a monovalent heterocyclic group (hereinafter referred to as a “substituted carboxyl group”. Also referred to as a “substituted carbonyl group”. It may be. The alkyl group, aryl group, arylalkyl group and monovalent heterocyclic group may have a substituent.
The substituted carboxyl group has usually 2 to 60 carbon atoms, preferably 2 to 48 carbon atoms. For example, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl group, isobutoxycarbonyl Group, tert-butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, cyclohexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group 3,7-dimethyloctyloxycarbonyl group, dodecyloxycarbonyl group, trifluoromethoxycarbonyl group, pentafluoroethoxycarbonyl group, perfluorobutoxycarbonyl group, Over-fluoro-hexyloxy group, perfluorooctyl group, phenoxycarbonyl group, naphthoxycarbonyl group, and pyridyloxycarbonyl group.

Examples of the unsubstituted or substituted arylene group represented by Ar ^a , Ar ^b and Ar ^c include groups represented by formula 2-001 to formula 2-018.

（式中、
Ｒは、水素原子または上述の置換基を表し、
Ｒ^aおよびＲ^ｂは、それぞれ独立に、アルキル基、アリール基または１価の複素環基を表す。
複数存在するＲは同一でも異なっていてもよい）。

(Where
R represents a hydrogen atom or the above-mentioned substituent,
R ^a and R ^b each independently represents an alkyl group, an aryl group, or a monovalent heterocyclic group.
A plurality of R may be the same or different).

Ar ^c represents the number of carbon atoms of the "divalent group in which two or more groups selected from the group consisting of divalent heterocyclic group unsubstituted or arylene group and an unsubstituted or substituted substitution linked" refers to a substituent It is 4-60 normally without including carbon number, Preferably it is 12-60. The divalent group is preferably a divalent group in which two groups are linked.
Examples of the divalent group in which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group are linked include the following formulas 2-201 to 2- Group represented by 208 is mentioned.

（式中、Ｒは、前記と同じ意味を表す。）

(In the formula, R represents the same meaning as described above.)

In the formula (2-001) to the formula (2-018) and the formula (2-201) to the formula (2-208), the polymer compound according to the present embodiment has good heat resistance and solubility in an organic solvent. Therefore, R is preferably a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent aromatic heterocyclic group, and a hydrogen atom or an unsubstituted or It is more preferably a substituted alkyl group. Further, since the luminance lifetime of the light-emitting element using a polymer compound of this embodiment is more excellent, as the R ^a and R ^b, both R ^a and R ^b are unsubstituted or alkyl or unsubstituted substituted Or a substituted aryl group, or R ^a is preferably an unsubstituted or substituted alkyl group and R ^b is preferably an unsubstituted or substituted aryl group, and both R ^a and R ^b are unsubstituted. Or R ^a is an unsubstituted or substituted alkyl group, R ^b is preferably an unsubstituted or substituted aryl group, and R ^a is an unsubstituted or substituted alkyl group. And R ^b is more preferably an unsubstituted or substituted aryl group.

The unsubstituted or substituted divalent heterocyclic group represented by Ar ^a , Ar ^b and Ar ^c does not include the carbon number of the substituent, and is preferably 2 to 60, and preferably 3 to 20. Examples of the substituent include the same substituents that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have.

Examples of the unsubstituted or substituted divalent heterocyclic group represented by Ar ^a , Ar ^b and Ar ^c include divalent groups represented by Formula 2-107 to Formula 2-117.

（式２−１０７〜２−１１７中、ＲおよびＲ^aは、前記と同じ意味を表す。）

(In formulas 2-107 to 2-117, R and R ^a have the same meaning as described above.)

Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different.
Ar ^d preferably represents an unsubstituted or substituted aryl group or an unsubstituted or substituted monovalent heterocyclic group, more preferably an unsubstituted or substituted aryl group. Examples of the substituent include the same substituents that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have.

The carbon number of the unsubstituted or substituted aryl group represented by Ar ^d does not include the carbon number of the substituent, is preferably 6 to 48, more preferably 6 to 20, and still more preferably 6 to 14. is there.

The aryl group represented by Ar ^d may have a substituent, for example, a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1 -Tetracenyl group, 2-tetracenyl group, 5-tetracenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-perylenyl group, 3-perylenyl group, 2-fluorenyl group, 3-fluorenyl group, 4 -Fluorenyl group, 2-phenanthrenyl group, 9-phenanthrenyl group, 6-chrycenyl group, 1-coronenyl group may be mentioned.

The carbon number of the unsubstituted or substituted monovalent heterocyclic group represented by Ar ^d does not include the carbon number of the substituent, and is usually 2 to 60, and preferably 3 to 20.

The monovalent heterocyclic group represented by Ar ^d may have a substituent, for example, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazole-2-yl Yl group, 2-thiazolyl group, 2-oxazolyl group, 2-thienyl group, 2-pyrrolyl group, 2-furyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-pyrazinyl group, 2- Pyrimidinyl group, 2-triazinyl group, 3-pyridazinyl group, 5-quinolyl group, 5-isoquinolyl group, 2-carbazolyl group, 3-carbazolyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 2-phenothiazinyl group, 3 -A phenothiazinyl group is mentioned.

The unsubstituted or substituted alkyl group represented by Ar ^d may be linear, branched or cyclic.
The carbon number of the alkyl group is usually 1 to 20 (in the case of a branched alkyl group and a cyclic alkyl group, usually 3 to 20), preferably 6 to 20 (cyclic alkyl group, not including the carbon number of the substituent. In this case, preferably 5 to 20), for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, cyclohexyl group, heptyl group, Octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, lauryl group, trifluoromethyl group, pentafluoroethyl group, perfluorobutyl group, perfluorohexyl group, perfluorooctyl group Can be mentioned.

  The structural unit represented by the formula (1) has good stability of the polymer compound according to the present embodiment, and light emission efficiency of the light emitting device using the polymer compound is improved. The structural unit represented by (1-2) is preferable, and the structural unit represented by the following formula (1-2-1) is more preferable.

（式（１−２）中、
R^a、R^bおよびR^cは、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R^a、R^bおよびR^cが複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
Ar^ｃおよびAr^ｄは、前記と同じ意味を表す。
hおよびjは、それぞれ独立に、０〜4の整数を表し、iは、０〜２の整数を表す。２個存在するｈ、ｉおよびｊは、それぞれ、同一であっても異なっていてもよい。）

(In the formula (1-2),
R ^a , R ^b and R ^c are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. When there are a plurality of R ^a , R ^b and R ^c , they may be the same or different.
Ar ^c and Ar ^d have the same meaning as described above.
h and j each independently represents an integer of 0 to 4, and i represents an integer of 0 to 2. Two h, i, and j may be the same or different. )

（式（１−２−１）中、
Ar^ｃ、Ar^ｄ、R^a、R^b、R^cおよびｉは、前記と同じ意味を表す。
kおよびlは、それぞれ独立に、０〜3の整数を表す。）

(In the formula (1-2-1),
Ar ^c , Ar ^d , R ^a , R ^b , R ^c and i represent the same meaning as described above.
k and l each independently represents an integer of 0 to 3. )

In formulas (1-2) and (1-2-1), R ^a , R ^b and R ^c are an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or A substituted alkyl group is preferred, and an unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group is more preferred.

  In formula (1-2), h and j are preferably an integer of 0 to 3, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably 0.

  In Formula (1-2), i is preferably 0 or 1, and more preferably 0.

  In formula (1-2-1), k and l are preferably integers of 0 to 2, more preferably 0 or 1, and still more preferably 0.

The Ar ^c, stability of the polymer compound of this embodiment is improved, and, since the emission efficiency of a light emitting element using the polymer compound becomes better, an unsubstituted or substituted arylene group or, , Preferably a divalent group in which two groups selected from the group consisting of unsubstituted or substituted arylene groups are linked, and are represented by the formula 2-001, formula 2-006, formula 2-201, formula 2-008, Formula 2-015 and Formula 2-010 are more preferable, Formula 2-001, Formula 2-006, Formula 2-201, Formula 2-008, Formula 2-010 are more preferable, and Formula 2- Particularly preferred are 001, Formula 2-006, and Formula 2-201.

The Ar ^d, stability of the polymer compound of this embodiment is improved, and, since the luminance lifetime of the light-emitting device using the polymer compound becomes better, is unsubstituted or substituted aryl group The group represented by the following formula (10) is more preferable.

（１０）
（式（１０）中、
Ｒ^5aおよびＲ^5eは、水素原子またはアルキル基を表し、
Ｒ^5b、Ｒ^5cおよびＲ^5dは、それぞれ独立に、水素原子、アルキル基またはアリール基を表す。）

(10)
(In the formula (10),
R ^5a and R ^5e represent a hydrogen atom or an alkyl group,
R ^5b , R ^5c and R ^5d each independently represents a hydrogen atom, an alkyl group or an aryl group. )

In formula (10), R ^5a is preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, or a butyl group from the viewpoint of ease of synthesis of the raw material compound of the polymer compound according to the present embodiment. Is more preferable.

In Formula (10), R ^5b has a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkyl group as a substituent from the viewpoint of ease of synthesis of the raw material compound of the polymer compound according to this embodiment. An aryl group (the carbon number of the alkyl group as a substituent is 4 to 20) is preferable, and a hydrogen atom is more preferable.

In formula (10), R ^5c is preferably a hydrogen atom or an alkyl group having 4 to 20 carbon atoms from the viewpoint of ease of synthesis of the raw material compound of the polymer compound according to this embodiment, and is preferably a methyl group or a butyl group. Is more preferable, and a butyl group is particularly preferable.

In Formula (10), R ^5d has a hydrogen atom, an alkyl group having 4 to 20 carbon atoms, or an alkyl group as a substituent from the viewpoint of ease of synthesis of the raw material compound of the polymer compound according to this embodiment. An aryl group (the carbon number of the alkyl group as a substituent is 4 to 20) is preferable, and a hydrogen atom is more preferable.

In Formula (10), R ^5e is preferably a hydrogen atom, a methyl group, an ethyl group, a propyl group, or a butyl group from the viewpoint of ease of synthesis of the raw material compound of the polymer compound according to the present embodiment. Is more preferable.

  As the structural unit represented by the formula (1), the following formula (1A-1) to formula (1A-8), formula (1B-1) to formula (1B-6), formula (1C-1) to formula (1C-6), Formula (1D-1) to Formula (1D-6), Formula (1E-1) to Formula (1E-4), Formula (1F-1) to Formula (1F-4), Formula ( 1G-1) to formula (1G-9), formula (1H-1) to formula (1H-4), formula (1I-1) to formula (1I-4), formula (1J-1) to formula (1J -4), Formula (1K-1) to Formula (1K-4), Formula (1L-1) to Formula (1L-6), Formula (1M-1) to Formula (1M-6), Formula (1N- 1) to formula (1N-4) and structural units represented by formula (1O-1) to formula (1O-4), and the luminance lifetime of the light-emitting element using the polymer compound according to this embodiment is high. Since it becomes more favorable, Formula (1A-1)-Formula (1A-8), Formula (1B- ) To formula (1B-6), formula (1D-1) to formula (1D-6), formula (1G-1) to formula (1G-9), formula (1I-1) to formula (1I-4) The structural units represented by formula (1K-1) to formula (1K-4), formula (1L-1) to formula (1L-6), and formula (1M-1) to formula (1M-6) are preferable. Formula (1A-1) to Formula (1A-4), Formula (1B-1) to Formula (1B-4), Formula (1D-1) to Formula (1D-4), Formula (1G-1) to The structural unit represented by Formula (1G-7), Formula (1K-1) to Formula (1K-4), Formula (1L-1) to Formula (1L-4) is more preferable, and Formula (1B-1) To Formula (1B-4), Formula (1D-1) to Formula (1D-4), Formula (1G-1) to Formula (1G-7), Formula (1K-1) to Formula (1K-4), The structural units represented by formula (1L-1) to formula (1L-4) are more preferred, and the formula (1B 1) to formula (1B-4), formula (1D-1) to formula (1D-4), formula (1G-1) to Formula (1G-7) structural units represented by is particularly preferred.

<Polymer compound>
Hereinafter, the polymer compound according to a preferred embodiment of the present invention will be described.

[First structural unit]
The polymer compound according to the present embodiment is a polymer compound including a structural unit represented by the formula (1) (hereinafter also referred to as “first structural unit”), and is represented by the formula (1). The unit is preferably a structural unit represented by the formula (1-2) or a structural unit represented by the formula (1-2-1).

[Second structural unit]
The polymer compound according to the embodiment further includes at least one structural unit selected from the group consisting of a structural unit represented by the following formula (3) and a structural unit represented by the following formula (4) (hereinafter, It is also preferably a polymer compound including “second structural unit”. This is because the stability and the light emission efficiency of the light-emitting element using the polymer compound are further improved. In addition, the structural unit represented by Formula (3) and the structural unit represented by Formula (4) may each be included alone or in combination of two or more.

（式（３）中、
Ar⁵は、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基または金属錯体構造を有する二価の基を表す。）
（式（４）中、
Ar⁶は、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表し、
Ar^７およびAr⁸は、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
２個存在するAr⁶は、同一であっても異なっていてもよい。
Ｅ_１、Ｅ_２およびＥ_３は、それぞれ独立に、水素原子、無置換もしくは置換アルキル基、無置換もしくは置換アリール基または無置換もしくは置換の一価の複素環基を表す。
aおよびｐは、それぞれ独立に、０または１を表し、０≦a＋ｐ≦１である。
Ａｒ^６、Ａｒ^７、Ａｒ^８およびＡｒ^９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、単結合、―O―、―CR¹R²―または―S―で渡環されていてもよい。R¹およびR²は、それぞれ独立に、水素原子、無置換もしくは置換アルキル基または無置換もしくは置換アリール基を表す。）

(In formula (3),
Ar ⁵ represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or a divalent group having a metal complex structure. )
(In formula (4),
Ar ⁶ each independently represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group,
Ar ⁷ and Ar ⁸ are composed of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group. Represents a divalent group in which two or more groups selected from the group are linked;
Two Ar ⁶ may be the same or different.
E ₁ , E ₂ and E ₃ 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.
a and p each independently represent 0 or 1, and 0 ≦ a + p ≦ 1.
Ar ⁶ , Ar ⁷ , Ar ⁸ and Ar ⁹ are each a group other than the group bonded to the nitrogen atom to which the group is bonded, a single bond, —O—, —CR ¹ R ² — or — It may be passed by S-. R ¹ and R ² each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. )

In the formula (3), examples of the unsubstituted or substituted arylene group represented by Ar ⁵ include the same unsubstituted or substituted arylene groups represented by Ar ^a , Ar ^b and Ar ^c described above. Examples of the substituent include the same substituents that the arylene group represented by Ar ^a , Ar ^b, and Ar ^c may have.

In formula (3), the unsubstituted or substituted divalent heterocyclic group represented by Ar ⁵ is the same as the unsubstituted or substituted divalent heterocyclic group represented by Ar ^a , Ar ^b and Ar ^c described above. Is mentioned. Examples of the substituent include the same substituents that the divalent heterocyclic group represented by Ar ^a , Ar ^b and Ar ^c can have.

In the formula (3), a divalent group in which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group represented by Ar ⁵ and an unsubstituted or substituted divalent heterocyclic group are linked is as described above. Examples thereof are the same as the divalent group represented by Ar ^{c in} which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group are linked. As the substituent, a divalent group in which two or more groups are linked are selected from the group consisting of unsubstituted or arylene group and an unsubstituted or substituted substituted divalent heterocyclic group represented by Ar ^c The thing similar to the substituent which is obtained is mentioned.

In the formula (3), the divalent group having a metal complex structure represented by Ar ⁵ is the removal of two hydrogen atoms directly bonded to the carbon atom constituting the organic ligand of the metal complex having an organic ligand. Is a divalent group.
The organic ligand usually has about 4 to 60 carbon atoms, such as 8-quinolinol and its derivatives, benzoquinolinol and its derivatives, 2-phenyl-pyridine and its derivatives, 2-phenyl-benzothiazole and its derivatives. 2-phenyl-benzoxazole and its derivatives, porphyrin and its derivatives.
Examples of the central metal of the metal complex include aluminum, zinc, beryllium, iridium, platinum, gold, europium, and terbium.
Examples of the metal complex having an organic ligand include metal complexes known as low-molecular fluorescent materials or phosphorescent materials.

In the formula (3), examples of the divalent group having a metal complex structure represented by Ar ⁵ include the following formulas 126 to 132.

（式１２６〜１３２中、Ｒは、前記と同じ意味を表す。）

(In formulas 126 to 132, R represents the same meaning as described above.)

As the unsubstituted or substituted arylene group represented by Ar ⁵ , the stability of the polymer compound according to the present embodiment is good, and the light emission efficiency of the light-emitting device using the polymer compound is further improved. Formula 2-001, Formula 2-002, Formula 2-003, Formula 2-004, Formula 2-005, Formula 2-006, Formula 2-008, Formula 2-009, Formula 2-010, Formula 2-011, Formula 2-012, Formula 2-016, and Formula 2-017 are preferred, Formula 2-001, Formula 2-002, Formula 2-004, Formula 2-006, Formula 2-007, Formula 2-008, Formula 2- 009, Formula 2-0011, Formula 2-016, and Formula 2-017 are more preferable, Formula 2-001, Formula 2-002, Formula 2-006, Formula 2-007, Formula 2-008, Formula 2-009, Formula 2-0011 is more preferable, Formula 2-001, Formula 2-006, Formula 2- 007 and formula 2-0011 are particularly preferred.

Examples of the divalent group in which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group represented by Ar ⁵ and an unsubstituted or substituted divalent heterocyclic group are linked include the polymer according to this embodiment. In order to improve the stability of the compound and to further improve the light emission efficiency of the light emitting device using the polymer compound, a divalent group in which two groups selected from the group consisting of unsubstituted or substituted arylene groups are linked. A group is preferred, Formula 2-201, Formula 2-202, Formula 2-204, and Formula 2-207 are more preferred, and Formula 2-201, Formula 2-202, and Formula 2-207 are even more preferred.

As an unsubstituted or substituted divalent heterocyclic group represented by Ar ⁵ , the stability of the polymer compound according to the present embodiment is improved, and the light emission efficiency of the light emitting device using the polymer compound is further improved. Therefore, Formula 2-110, Formula 2-111, Formula 2-112, Formula 2-113, Formula 2-114, Formula 2-115, Formula 2-116, and Formula 2-117 are preferable, and Formula 2-110 Formula 2-111 and Formula 2-115 are more preferable.

  The structural unit represented by the formula (3) is represented by the structural unit represented by the following formula (3-1) and the following formula (3-2) from the viewpoint of the luminance life of the light emitting device using the polymer compound. And a structural unit represented by the following formula (3-5) or a structural unit represented by the following formula (3-5). In addition, the structural unit represented by Formula (3-1), the structural unit represented by Formula (3-2), Formula (3-4), and the structural unit represented by Formula (3-5) These structural units may be included alone or in combination of two or more.

（式（３−１）中、
R³およびR⁴は、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R³およびR⁴が複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
bおよびｃは、それぞれ独立に、０〜３の整数を表す。
R⁵およびR⁶は、それぞれ独立に、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。）

(In Formula (3-1),
R ³ and R ⁴ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or unsubstituted Alternatively, it represents a substituted alkyl group. When a plurality of R ³ and R ⁴ are present, they may be the same or different.
b and c each independently represent an integer of 0 to 3.
R ⁵ and R ⁶ are each independently a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. )

（式（３−２）中、
R^７は、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R^７が複数存在する場合、それらは同一であっても異なっていてもよい。
dは、０〜４の整数を表す。）

(In the formula (3-2),
R ⁷ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted alkyl group. . When a plurality of R ⁷ are present, they may be the same or different.
d represents an integer of 0 to 4. )

（式（３−４）中、
R^１２は、水素原子、無置換もしくは置換のアルキル基を表す。２個存在するR^１２は、同一であっても異なっていてもよい。）

(In Formula (3-4),
R ¹² represents a hydrogen atom, an unsubstituted or substituted alkyl group. Two R ¹² may be the same or different. )

（式（３−５）中、
R^１３は、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換のアルキル基を表す。複数存在するR^１３は、同一であっても異なっていてもよい。）

(In the formula (3-5),
R ¹³ represents a hydrogen atom, an unsubstituted or substituted aryl group, or an unsubstituted or substituted alkyl group. A plurality of R ¹³ may be the same or different. )

In formula (3-1), R ³ and R ⁴ are preferably an unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group.

  In formula (3-1), b and c are preferably 0 or 1 and more preferably 0 from the viewpoint of ease of synthesis of the raw material compound of the polymer compound according to this embodiment.

In formula (3-1), R ⁵ and R ⁶ are preferably an unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group from the viewpoint of the luminance lifetime of the light emitting device using the polymer compound.

In formula (3-1), examples of the alkyl group represented by R ⁵ and R ⁶ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a pentyl group, 2- Examples include methylbutyl group, isoamyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, 3,7-dimethyloctyl group, and dodecyl group.

In formula (3-1), examples of the aryl group represented by R ⁵ and R ⁶ include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

In formula (3-1), examples of the monovalent heterocyclic group represented by R ⁵ and R ⁶ include the same monovalent heterocyclic groups represented by Ar ^d described above.

In formula (3-1), as R ⁵ and R ⁶ , the heat resistance of the polymer compound according to this embodiment and the solubility in organic solvents are improved,
An unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group is preferred,
More preferably, an unsubstituted aryl group or alkyl group, an alkoxy group, an aryl group, an aryl group substituted with a substituted amino group, or an unsubstituted alkyl group or alkyl group, an alkoxy group, an aryl group, or a substituted amino group A substituted alkyl group,
More preferably, it is an aryl group substituted with an alkyl group or an aryl group, or an unsubstituted alkyl group,
More preferably, 4-tolyl group, 4-butylphenyl group, 4-tert-butylphenyl group, 4-hexylphenyl group, 4-octylphenyl group, 4- (2-ethylhexyl) phenyl group, 4- (3, 7-dimethyloctyl) phenyl group, 3-tolyl group, 3-butylphenyl group, 3-tert-butylphenyl group, 3-hexylphenyl group, 3-octylphenyl group, 3- (2-ethylhexyl) phenyl group, 3 -(3,7-dimethyloctyl) phenyl group, 3,5-dimethylphenyl group, 3,5-di- (tert-butyl) phenyl group, 3,5-dihexylphenyl group, 3,5-dioctylphenyl group, 3,4-dihexylphenyl group, 3,4-dioctylphenyl group, 4-hexyloxyphenyl group, 4-octyloxyphenyl group, 4 (2-ethoxy) ethoxyphenyl group, 4- (4′-tert-butylbiphenylyl) group, 9,9-dihexylfluoren-2-yl group, 9,9-dioctylfluoren-2-yl group, pentyl group, A hexyl group, a 2-ethylhexyl group, an octyl group, or a 3,7-dimethyloctyl group.

In Formula (3-1), as R ⁵ and R ⁶ , since the luminance life of the light emitting device using the polymer compound according to this embodiment is more excellent, both R ⁵ and R ⁶ are unsubstituted or substituted. It is preferable that R ⁵ is an unsubstituted or substituted alkyl group and R ⁶ is an unsubstituted or substituted aryl group, and both R ⁵ and R ⁶ are Is more preferably an unsubstituted or substituted aryl group, or R ⁵ is an unsubstituted or substituted alkyl group and R ⁶ is an unsubstituted or substituted aryl group, and R ⁵ is an unsubstituted or substituted aryl group. More preferably, it is an alkyl group and R ⁶ is an unsubstituted or substituted aryl group.

  Examples of the structural unit represented by the formula (3-1) include structural units represented by the following formulas 2-501 to 2-520, and the luminance of the light-emitting element using the polymer compound according to the present embodiment. From the viewpoint of life, Formula 2-501 to Formula 2-512, Formula 2-517 to Formula 2-527 are preferable, Formula 2-505 to Formula 2-512, and Formula 2-517 to Formula 2-527 are more preferable. Formula 2-517 to Formula 2-527 are more preferable, and Formula 2-518 to Formula 2-520, Formula 2-523, Formula 2-526, and Formula 2-527 are particularly preferable.

In formula (3-2), R ⁷ is preferably because the stability of the polymer compound according to the present embodiment is improved and the luminance life of the light-emitting device using the polymer compound is further improved. An unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group.

  In formula (3-2), d is preferably an integer of 0 to 2, and more preferably 2.

  As the structural unit represented by the formula (3-2), structural units represented by the following formula (8A-1) to formula (8A-9), formula (8B-1) to formula (8B-12) And the luminance lifetime of the light emitting device using the polymer compound according to the present embodiment is improved, so that the formula (8A-1) to the formula (8A-9), the formula (8B-1) to the formula ( 8B-10) is preferable, and Formula (8A-1) to Formula (8A-9) are more preferable.

  Examples of the structural unit represented by the formula (3-4) include structural units represented by the following formulas 4-001 to 4-006, and the luminance of the light-emitting element using the polymer compound according to the present embodiment. Since the lifetime is more excellent, Formula 4-001, Formula 4-002, Formula 4-004, and Formula 4-005 are preferable, and Formula 4-001 and Formula 4-002 are more preferable.

  Examples of the structural unit represented by the formula (3-5) include structural units represented by the following formulas 4-010 to 4-019, and the luminance of the light-emitting element using the polymer compound according to the present embodiment. Since the lifetime is more excellent, Formula 4-010, Formula 4-011, Formula 4-013 to Formula 4-016 are preferable, Formula 4-013 to Formula 4-016 are more preferable, Formula 4-013, Formula 4-014 Is more preferable.

In the formula (4), the unsubstituted or substituted arylene group represented by Ar ⁶ , Ar ⁷ and Ar ⁸ is the same as the unsubstituted or substituted arylene group represented by Ar ^a , Ar ^b and Ar ^c described above. Can be mentioned.

In the formula (4), the unsubstituted or substituted divalent heterocyclic group represented by Ar ⁶ , Ar ⁷ and Ar ⁸ is an unsubstituted or substituted divalent heterocyclic group represented by the above-mentioned Ar ^a , Ar ^b and Ar ^c . The thing similar to a heterocyclic group is mentioned.

In formula (4), as a divalent group in which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group represented by Ar ⁷ and Ar ⁸ and an unsubstituted or substituted divalent heterocyclic group are linked Is the same as the divalent group in which two or more groups selected from the group consisting of the unsubstituted or substituted arylene group and the unsubstituted or substituted divalent heterocyclic group represented by Ar ^c are linked. In addition, since the polymer compound according to the present embodiment has good stability, and the light emitting device using the polymer compound has higher luminous efficiency, the polymer compound is selected from the group consisting of unsubstituted or substituted arylene groups. A divalent group in which two groups are linked is preferred.

In the formula (4), Ar ⁶ is not substituted or substituted because the stability of the polymer compound according to the present embodiment is improved and the luminous efficiency of the light emitting device using the polymer compound is further improved. Substituted arylene groups are preferred, with Formula 2-001, Formula 2-010, and Formula 2-015 being more preferred, and Formula 2-001 and Formula 2-010 being more preferred. As Ar ⁷ and Ar ⁸ , the stability of the polymer compound according to the present embodiment is improved, and the light emission efficiency of the light emitting device using the polymer compound is further improved. The arylene group is preferably Formula 2-001, Formula 2-010, Formula 2-015, or Formula 2-201, more preferably Formula 2-001, Formula 2-010, or Formula 2-201. Further preferred.

In the formula (4), the unsubstituted or substituted alkyl group, the unsubstituted or substituted aryl group and the unsubstituted or substituted monovalent heterocyclic group represented by E ₁ , E ₂ and E ₃ are represented by Ar ^d described above. The same thing as an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted monovalent | monohydric heterocyclic group is mentioned, respectively.

In formula (4), as E ₁ , E ₂ and E ₃ , the stability of the polymer compound according to the present embodiment is good, and the light emission efficiency of the light emitting device using the polymer compound is better. Therefore, a substituted aryl group is preferable.

Ar ⁶ , Ar ⁷ , Ar ⁸ and Ar ⁹ are each a group other than the group bonded to the nitrogen atom to which the group is bonded, a single bond, —O—, —CR ¹ R ² — or — When the ring is transferred with S-, the stability of the polymer compound according to the present embodiment is improved, and the light-emitting element using the polymer compound has better luminous efficiency. —Or —CR ¹ R ² — is preferable, a single bond or —O— is more preferable, and —O— is still more preferable.

  Examples of the structural unit represented by the formula (4) include structural units represented by the following formulas 3-001 to 3-006. Since the hole transportability becomes better, Formula 3-001, Formula 3-002, Formula 3-004, Formula 3-005, Formula 3-006, and Formula 3-007 are preferable, Formula 3-001, Formula 3-007 002, Formula 3-004, Formula 3-005, and Formula 3-006 are more preferable.

（式３−００１〜式３−００７中、Ｒ、Ｒ^aおよびＲ^ｂは、前記と同じ意味を表す。）

(In Formula 3-001 to Formula 3-007, R, R ^a and R ^b represent the same meaning as described above.)

  Since the structural unit represented by the formula (4) has a higher luminance life of the light emitting element using the polymer compound, the structural unit represented by the following formula (4-1) or the following formula (4-2) A structural unit represented by a structure is preferable.

（式（４−１）中、
Qは単結合、―O―、―C（R¹）（R²）―、―S―を表し、R¹およびR²は、前記と同じ意味を表す。
Ar¹⁴は、水素原子、無置換もしくは置換のアルキル基、無置換もしくは置換のアリールアルキル基、無置換もしくは置換のアリール基または無置換もしくは置換の一価の複素環基を表す。
R⁸およびR⁹は、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R⁸およびR⁹が複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
ｅおよびfは、それぞれ独立に、０〜３の整数である。）

(In the formula (4-1),
Q represents a single bond, —O—, —C (R ¹ ) (R ² ) —, —S—, and R ¹ and R ² represent the same meaning as described above.
Ar ¹⁴ represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted arylalkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
R ⁸ and R ⁹ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or unsubstituted Alternatively, it represents a substituted alkyl group. When a plurality of R ⁸ and R ⁹ are present, they may be the same or different.
e and f are each independently an integer of 0 to 3. )

（式（４−２）中、
Ａｒ^１３は、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表す。
R^１０およびR^１１は、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基、または無置換もしくは置換のアルキル基を表す。R^１０およびR^１１が複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
gは、０〜４の整数を表し、mは、０〜５の整数を表し、nは、０または１を表す。２個存在するｇおよびｍは、それぞれ同一であっても異なっていてもよい。）

(In the formula (4-2),
Ar ¹³ is selected from the group consisting of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group It represents a divalent group in which two or more groups are linked.
R ¹⁰ and R ¹¹ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or Represents a substituted or substituted alkyl group. When a plurality of R ¹⁰ and R ¹¹ are present, they may be the same or different.
g represents an integer of 0 to 4, m represents an integer of 0 to 5, and n represents 0 or 1. Two of g and m may be the same or different. )

  In Formula (4-1), Q is preferably a simple compound because the stability of the polymer compound according to this embodiment is improved and the luminance life of the light-emitting element using the polymer compound is further improved. It is a bond or —O—, more preferably —O—.

In Formula (4-1), R ⁸ and R ⁹ are excellent in the stability of the polymer compound according to this embodiment, and the luminance life of the light-emitting element using the polymer compound is further improved. An unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group is preferred, and an unsubstituted or substituted alkyl group is more preferred.

In formula (4-1), Ar ¹⁴ is not substituted because the stability of the polymer compound according to the present embodiment is improved and the luminance life of the light emitting device using the polymer compound is further improved. Or a substituted alkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group is preferred, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group is more preferred, an unsubstituted or A substituted aryl group is more preferred, and a substituted aryl group is particularly preferred.

  In the formula (4-1), e and f are 0 because the stability of the polymer compound according to this embodiment is improved and the luminance life of the light emitting device using the polymer compound is further improved. Or it is preferable that it is 1, and it is more preferable that it is 0.

  Examples of the structural unit represented by the formula (4-1) include structural units represented by the following formulas (10A-1) to (10A-17). Since stability becomes favorable and the luminance lifetime of the light emitting element using the said high molecular compound becomes more favorable, Formula (10A-1)-Formula (10A-14) are preferable, Formula (10A-4)- Formula (10A-11) is more preferable.

In Formula (4-2), R ¹⁰ and R ¹¹ are excellent in the stability of the polymer compound according to the present embodiment, and the luminance life of the light emitting device using the polymer compound is further improved. An unsubstituted or substituted aryl group or an unsubstituted or substituted alkyl group is preferred.

In Formula (4-2), Ar ¹³ is unsubstituted or substituted because the stability of the polymer compound according to this embodiment is improved and the luminance life of the light-emitting device using the polymer compound is more excellent. Or a divalent group in which two or more groups selected from the group consisting of an unsubstituted or substituted arylene group are connected, and an unsubstituted or substituted arylene group is more preferable.

  In Formula (4-2), g is 0 or 1 because the stability of the polymer compound according to the present embodiment is improved and the luminance life of the light emitting device using the polymer compound is further improved. Is preferable, and 0 is more preferable.

  In Formula (4-2), m is 0 to 4 because the stability of the polymer compound according to the present embodiment is improved and the luminance life of the light emitting device using the polymer compound is further improved. The integer of 1 is preferable, the integer of 1-3 is more preferable, and 1 or 3 is still more preferable.

  In formula (4-2), n is preferably 1 because the stability of the polymer compound according to the present embodiment is improved and the luminance life of the light-emitting device using the polymer compound is further improved. .

  Examples of the structural unit represented by the formula (4-2) include structural units represented by the following formulas (14A-1) to (14A-30). Since stability becomes favorable and the luminance life of the light emitting element using the polymer compound is more excellent, the formula (14A-2) to the formula (14A-7), the formula (14A-10), the formula (14A- 16) to formula (14A-19), formula (14A-23), formula (14A-27) to formula (14A-29) are preferable, and formula (14A-3) to formula (14A-7), formula (14A) −10), Formula (14A-19), Formula (14A-23), Formula (14A-27), and Formula (14A-29) are more preferable, Formula (14A-6), Formula (14A-7) Formula ( 14A-19) is more preferable.

  The polymer compound according to the present embodiment may include a structural unit represented by the following formula (9) as a structural unit represented by the formula (3). This is because by including the structural unit represented by the formula (9), the electron injecting and transporting property of the light emitting element using the polymer compound is further improved. In addition, the structural unit represented by Formula (9) may be contained only 1 type, or may be contained 2 or more types.

（式（９）中、
Ar^１０およびAr^１１は、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表す。
Ar^１２は、水素原子、無置換もしくは置換のアリール基または無置換もしくは置換の一価の複素環基を表す。）

(In Formula (9),
Ar ¹⁰ and Ar ¹¹ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹² represents a hydrogen atom, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group. )

In the formula (9), the unsubstituted or substituted arylene group represented by Ar ¹⁰ and Ar ¹¹ and the unsubstituted or substituted divalent heterocyclic group include the unsubstituted or represented by Ar ^a , Ar ^b and Ar ^c described above. Examples thereof include the same as the substituted arylene group and the unsubstituted or substituted divalent heterocyclic group.

In the formula (9), the unsubstituted or substituted aryl group represented by Ar ₁₂ and the unsubstituted or substituted monovalent heterocyclic group include the unsubstituted or substituted aryl group represented by Ar ^d described above, Examples thereof are the same as those of the substituted monovalent heterocyclic group.

In the formula (9), as Ar ¹⁰ and Ar ¹¹ , the stability of the polymer compound according to the present embodiment is improved, and the light emission efficiency of the light emitting device using the polymer compound is further improved. An unsubstituted or substituted arylene group is preferred, and Formula 2-001 is more preferred.

In Formula (9), Ar ¹² is not substituted or substituted because the stability of the polymer compound according to the present embodiment is improved, and the light emission efficiency of the light-emitting device using the polymer compound is further improved. A substituted aryl group is preferred.

  Examples of the structural unit represented by Formula (9) include structural units represented by Formula (13A-1) to Formula (13A-6), and light emission using the polymer compound according to the present embodiment. Since the electron transport property of the device becomes better, Formula (13A-2) to Formula (13A-5) are preferable, and Formula (13A-4) and Formula (13A-5) are more preferable.

[3rd structural unit]
Since the polymer compound according to this embodiment makes it easier to produce a light-emitting device obtained using the polymer compound, the structural unit represented by the following formula (3-3) (in the formula (3) above) And a structural unit represented by the following formula (4-3) (a structural unit represented by the formula (4)). And at least one kind of structural unit selected from the group consisting of the structural unit represented by formula (4-2). In addition, the structural unit represented by Formula (3-3) and the structural unit represented by Formula (4-3) may each be included alone or in combination of two or more.

（式（３−３）中、
Ｒ^２１は、架橋性基を表す。
Ｒ^２２は、水素原子、架橋性基、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基または非置換若しくは置換の一価の複素環基を表す。）
（式（４−３）中、
Ｒ^２３は、架橋性基を表す。
Ｒ^２４は、架橋性基、非置換若しくは置換のアルキル基、非置換若しくは置換のアリール基、または、非置換若しくは置換の一価の複素環基を表す。
ｑは、０または１を表す。）

(In Formula (3-3),
R ²¹ represents a crosslinkable group.
R ²² represents a hydrogen atom, a crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group. )
(In Formula (4-3),
R ²³ represents a crosslinkable group.
R ²⁴ represents a crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
q represents 0 or 1; )

In formula (3-3), R ²¹ represents a crosslinkable group. Here, examples of the crosslinkable group include groups represented by the following formulas (15A-1) to (15A-27). From the viewpoint of the luminance lifetime of the light emitting device using the polymer compound, groups represented by the formula (15A-3) to the formula (15A-15) are preferable, and the formula (15A-6) to the formula (15A-9) are preferable. Or the group represented by Formula (15A-12)-Formula (15A-14) is more preferable.

（式中、＊は結合手を表す。）

(In the formula, * represents a bond.)

In formula (3-3), R ²² is preferably a crosslinkable group or an unsubstituted or substituted aryl group, and more preferably a crosslinkable group.

Examples of the crosslinkable group represented by R ²² include the same crosslinkable groups represented by R ²¹ described above.

The unsubstituted or substituted alkyl group represented by R ²² , the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group include the unsubstituted or substituted alkyl group represented by R ₅ and R ₆ described above. And the same as the unsubstituted or substituted aryl group and the unsubstituted or substituted monovalent heterocyclic group.

  Examples of the structural unit represented by the formula (3-3) include structural units represented by the following formulas (15B-1) to (15B-8). From the viewpoint of the luminance lifetime of the light-emitting element using the polymer compound, structural units represented by the formula (15B-2) to the formula (15B-8) are preferable, and the formula (15B-2) or the formula (15B-4) is preferable. ) To (15B-6) are more preferable, and a structural unit represented by formula (15B-2), formula (15B-5) or (15B-6) is more preferable.

In formula (4-3), R ²³ represents a crosslinkable group. The crosslinkable group R ²³ represents, the same as the crosslinkable group represented by R ²¹ described above.

In formula (4-3), R ²⁴ represents a crosslinkable group, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group, preferably crosslinkable It is a group.

Examples of the crosslinkable group represented by R ²⁴ include the same crosslinkable groups represented by R ²¹ described above.

The unsubstituted or substituted alkyl group represented by R ²⁴ , the unsubstituted or substituted aryl group, and the unsubstituted or substituted monovalent heterocyclic group include the unsubstituted or substituted alkyl group represented by Ar ^d described above, and unsubstituted. Or the same thing as a substituted aryl group and an unsubstituted or substituted monovalent | monohydric heterocyclic group is mentioned, respectively.

  In formula (4-3), n is preferably 0.

  Examples of the structural unit represented by Formula (4-3) include structural units represented by the following Formula (16A-1) to Formula (16A-4). From the viewpoint of the luminance lifetime of the light-emitting element using the polymer compound, the structural unit represented by the formula (16A-2) or the formula (16A-4) is preferable, and the structural unit represented by the formula (16A-2) Is more preferable.

  The content of the structural unit represented by the formula (1) is high because the stability of the polymer compound according to the present embodiment is good and the light emission efficiency of the light emitting device using the polymer compound is more excellent. 0.1 mol% or more and 50 mol% or less is preferable, 0.1 mol% or more and 20 mol% or less is more preferable, and 5 mol% or more and 20 mol% or less is preferable with respect to the total content of the structural units contained in the molecular compound. Is more preferable.

  The content of the structural unit represented by the formula (1) is because the stability of the polymer compound according to this embodiment is good, and the hole transport property of the light-emitting device using the polymer compound is more excellent. , Preferably 5 mol% or more and 50 mol% or less, more preferably 10 mol% or more and 50 mol% or less, and further more preferably 30 mol% or more and 50 mol% or less, based on the total content of the structural units contained in the polymer compound. preferable.

  The total content of the structural unit represented by the formula (1), the structural unit represented by the formula (3), and the structural unit represented by the formula (4) is such that the stability of the polymer compound according to this embodiment is determined. Since the hole transport property of the light emitting device using the polymer compound is more excellent and 80% by mass or more is preferable with respect to the total content of the constituent units contained in the polymer compound, 90% by mass The above is more preferable and 99 mass% or more is still more preferable.

  The structural unit represented by Formula (1), the structural unit represented by Formula (3), the structural unit represented by Formula (4), the structural unit represented by Formula (3-3), and the formula (4- 3) The total content of the structural units represented by 3) is high because the stability of the polymer compound according to the present embodiment is good and the production of a light-emitting device using the polymer compound is easier. 80 mass% or more is preferable with respect to the total content of the structural unit contained in a molecular compound, 90 mass% or more is more preferable, and 99 mass% or more is still more preferable.

The number average molecular weight (Mn) in terms of polystyrene by gel permeation chromatography (hereinafter referred to as “GPC”) of the polymer compound according to this embodiment is usually 1 × 10 ³ to 1 × 10 ⁸ , From the viewpoint of film formation of a liquid composition to be described later, it is preferably 1 × 10 ⁴ to 1 × 10 ⁶ .
Moreover, the polystyrene-equivalent weight average molecular weight (Mw) of the polymer compound according to this embodiment is usually 1 × 10 ³ to 1 × 10 ⁸ , and from the viewpoint of film formation of the liquid composition described later, preferably ^{1 × 10 4 ~5 × 10 6} , more preferably ^{3 × 10 4 ~1 × 10 6} , still more preferably from ^{5 × 10 4 ~5 × 10 5} .

  The terminal group of the polymer compound according to the present embodiment is a stable group because if the polymerization active group remains as it is, the light emission characteristics and luminance life of the light emitting device using the polymer compound may decrease. It is preferable that The stable group as the terminal group is preferably a group that forms a conjugation with the main chain of the polymer compound, and specifically, an aryl group or a monovalent heterocyclic group (particularly a monovalent aromatic heterocyclic group). (Specifically, groups described in Chemical formula 10 of JP-A-9-45478).

  The polymer compound according to this embodiment may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or may be in another mode.

  Preferred embodiments of the polymer compound of the present invention include the following polymer compounds (P-1) to (P-40). In addition, Q2-Q35 represents the molar ratio of the repeating unit in parenthesis with respect to all the structural units of a high molecular compound.

  Polymer compound (P-1);

（式中、Ｑ３５=０．１〜２０、Ｑ４=１〜９０、Ｑ２=１〜９０であり、Ｑ３５＋Ｑ４＋Ｑ２＝１００である。）

(In the formula, Q35 = 0.1-20, Q4 = 1-90, Q2 = 1-90, and Q35 + Q4 + Q2 = 100.)

Polymer compound (P-2);

（式中、Ｑ３５=０．１〜２０、Ｑ１１=１〜９０、Ｑ１２=１〜９０であり、Ｑ３５＋Ｑ１１＋Ｑ１２＝１００である。）

(In the formula, Q35 = 0.1-20, Q11 = 1-90, Q12 = 1-90, and Q35 + Q11 + Q12 = 100.)

Polymer compound (P-3);

（式中、Ｑ３５=０．１〜２０、Ｑ３=１〜９０、Ｑ１１=１〜９０であり、Ｑ３５＋Ｑ３＋Ｑ１１＝１００である。）

(In the formula, Q35 = 0.1-20, Q3 = 1-90, Q11 = 1-90, and Q35 + Q3 + Q11 = 100.)

Polymer compound (P-4);

（式中、Ｑ３５=０．１〜２０、Ｑ１３=１〜９０、Ｑ２=１〜９０であり、Ｑ３５＋Ｑ１３＋Ｑ２＝１００である。）

(In the formula, Q35 = 0.1-20, Q13 = 1-90, Q2 = 1-90, and Q35 + Q13 + Q2 = 100.)

A high molecular compound (P-5);

（式中、Ｑ３５=０．１〜２０、Ｑ１９=０．１〜２０、Ｑ１１=１〜９０、Ｑ１７=１〜９０であり、Ｑ３５＋Ｑ１９＋Ｑ１１＋Ｑ１７＝１００である。）

(In the formula, Q35 = 0.1-20, Q19 = 0.1-20, Q11 = 1-90, Q17 = 1-90, and Q35 + Q19 + Q11 + Q17 = 100.)

A high molecular compound (P-6);

（式中、Ｑ２８=０．１〜２０、Ｑ１９=０．１〜２０、Ｑ１２=１〜９０、Ｑ２０=１〜９０であり、Ｑ２８＋Ｑ１９＋Ｑ１２＋Ｑ２０＝１００である。）

(In the formula, Q28 = 0.1-20, Q19 = 0.1-20, Q12 = 1-90, Q20 = 1-90, and Q28 + Q19 + Q12 + Q20 = 100.)

Polymer compound (P-7);

（式中、Ｑ３０=０．１〜１０、Ｑ６=１〜９０、Ｑ１１=１〜９０、Ｑ２１=０．１〜２０であり、Ｑ３０＋Ｑ６＋Ｑ１１＋Ｑ２１＝１００である。）

(In the formula, Q30 = 0.1 to 10, Q6 = 1 to 90, Q11 = 1 to 90, Q21 = 0.1 to 20, and Q30 + Q6 + Q11 + Q21 = 100.)

A high molecular compound (P-8);

（式中、Ｑ２９=０．１〜１０、Ｑ８=１〜９０、Ｑ２１=０．１〜２０、Ｑ９=１〜９０であり、Ｑ２９＋Ｑ８＋Ｑ２１＋Ｑ９＝１００である。）

(In the formula, Q29 = 0.1 to 10, Q8 = 1 to 90, Q21 = 0.1 to 20, Q9 = 1 to 90, and Q29 + Q8 + Q21 + Q9 = 100.)

A high molecular compound (P-9);

（式中、Ｑ３０=０．１〜１０、Ｑ２=１〜９０、Ｑ３=１〜９０、Ｑ２３=０．１〜２０であり、Ｑ３０＋Ｑ２＋Ｑ３＋Ｑ２３＝１００である。）

(In the formula, Q30 = 0.1 to 10, Q2 = 1 to 90, Q3 = 1 to 90, Q23 = 0.1 to 20, and Q30 + Q2 + Q3 + Q23 = 100.)

A high molecular compound (P-10);

（式中、Ｑ３５=０．１〜１０、Ｑ４=１〜９０、Ｑ５=１〜９０、Ｑ２２=０．１〜２０であり、Ｑ３５＋Ｑ４＋Ｑ５＋Ｑ２２＝１００である。）

(In the formula, Q35 = 0.1-10, Q4 = 1-90, Q5 = 1-90, Q22 = 0.1-20, and Q35 + Q4 + Q5 + Q22 = 100.)

A high molecular compound (P-11);

（式中、Ｑ３５=０．１〜４０、Ｑ１１=１〜９０、Ｑ１２=１〜９０、Ｑ２７=０．１〜２０であり、Ｑ３５＋Ｑ１１＋Ｑ１２＋Ｑ２７＝１００である。）

(In the formula, Q35 = 0.1-40, Q11 = 1-90, Q12 = 1-90, Q27 = 0.1-20, and Q35 + Q11 + Q12 + Q27 = 100.)

A high molecular compound (P-12);

（式中、Ｑ３５=０．１〜４０、Ｑ６=１〜９０、Ｑ７=１〜９０、Ｑ２４=０．１〜２０であり、Ｑ３５＋Ｑ６＋Ｑ７＋Ｑ２４＝１００である。）

(In the formula, Q35 = 0.1-40, Q6 = 1-90, Q7 = 1-90, Q24 = 0.1-20, and Q35 + Q6 + Q7 + Q24 = 100.)

A high molecular compound (P-13);

（式中、Ｑ３５=０．１〜４０、Ｑ３=１〜９０、Ｑ１１=１〜９０、Ｑ２５=０．１〜２０、Ｑ２４=０．１〜２０であり、Ｑ３５＋Ｑ３＋Ｑ１１＋Ｑ２５＋Ｑ２４＝１００である。）

(In the formula, Q35 = 0.1-40, Q3 = 1-90, Q11 = 1-90, Q25 = 0.1-20, Q24 = 0.1-20, and Q35 + Q3 + Q11 + Q25 + Q24 = 100.)

A high molecular compound (P-14);

（式中、Ｑ３０=０．１〜４０、Ｑ４=１〜９０、Ｑ５=１〜９０、Ｑ２６=０．１〜２０であり、Ｑ３０＋Ｑ４＋Ｑ５＋Ｑ２６＝１００である。）

(In the formula, Q30 = 0.1-40, Q4 = 1-90, Q5 = 1-90, Q26 = 0.1-20, and Q30 + Q4 + Q5 + Q26 = 100.)

A high molecular compound (P-15);

（式中、Ｑ３１=０．１〜２０、Ｑ４=１〜９０、Ｑ２=１〜９０であり、Ｑ３１＋Ｑ４＋Ｑ２＝１００である。）

(In the formula, Q31 = 0.1 to 20, Q4 = 1 to 90, Q2 = 1 to 90, and Q31 + Q4 + Q2 = 100.)

A high molecular compound (P-16);

（式中、Ｑ３２=０．１〜２０、Ｑ１１=１〜９０、Ｑ１２=１〜９０であり、Ｑ３２＋Ｑ１１＋Ｑ１２＝１００である。）

(In the formula, Q32 = 0.1-20, Q11 = 1-90, Q12 = 1-90, and Q32 + Q11 + Q12 = 100.)

A high molecular compound (P-17);

（式中、Ｑ２９=０．１〜２０、Ｑ３=１〜９０、Ｑ１１=１〜９０であり、Ｑ２９＋Ｑ３＋Ｑ１１＝１００である。）

(In the formula, Q29 = 0.1 to 20, Q3 = 1 to 90, Q11 = 1 to 90, and Q29 + Q3 + Q11 = 100.)

A high molecular compound (P-18);

（式中、Ｑ３４=０．１〜２０、Ｑ１３=１〜９０、Ｑ２=１〜９０であり、Ｑ３４＋Ｑ１３＋Ｑ２＝１００である。）

(In the formula, Q34 = 0.1 to 20, Q13 = 1 to 90, Q2 = 1 to 90, and Q34 + Q13 + Q2 = 100.)

A high molecular compound (P-19);

（式中、Ｑ２９=０．１〜２０、Ｑ１９=０．１〜２０、Ｑ１１=１〜９０、Ｑ１７=１〜９０であり、Ｑ２９＋Ｑ１９＋Ｑ１１＋Ｑ１７＝１００である。）

(In the formula, Q29 = 0.1-20, Q19 = 0.1-20, Q11 = 1-90, Q17 = 1-90, and Q29 + Q19 + Q11 + Q17 = 100.)

A high molecular compound (P-20);

（式中、Ｑ２９=０．１〜２０、Ｑ１９=０．１〜２０、Ｑ１２=１〜９０、Ｑ２０=１〜９０であり、Ｑ２９＋Ｑ１９＋Ｑ１２＋Ｑ２０＝１００である。）

(In the formula, Q29 = 0.1-20, Q19 = 0.1-20, Q12 = 1-90, Q20 = 1-90, and Q29 + Q19 + Q12 + Q20 = 100.)

A high molecular compound (P-21);

（式中、Ｑ３４=０．１〜１０、Ｑ６=１〜９０、Ｑ１１=１〜９０、Ｑ２１=０．１〜２０であり、Ｑ３４＋Ｑ６＋Ｑ１１＋Ｑ２１＝１００である。）

(In the formula, Q34 = 0.1 to 10, Q6 = 1 to 90, Q11 = 1 to 90, Q21 = 0.1 to 20, and Q34 + Q6 + Q11 + Q21 = 100.)

A high molecular compound (P-22);

（式中、Ｑ３０=０．１〜１０、Ｑ８=１〜９０、Ｑ２１=０．１〜２０、Ｑ９=１〜９０であり、Ｑ３０＋Ｑ８＋Ｑ２１＋Ｑ９＝１００である。）

(In the formula, Q30 = 0.1 to 10, Q8 = 1 to 90, Q21 = 0.1 to 20, Q9 = 1 to 90, and Q30 + Q8 + Q21 + Q9 = 100.)

A high molecular compound (P-23);

（式中、Ｑ２８=０．１〜１０、Ｑ２=１〜９０、Ｑ３=１〜９０、Ｑ２３=０．１〜２０であり、Ｑ２８＋Ｑ２＋Ｑ３＋Ｑ２３＝１００である。）

(In the formula, Q28 = 0.1 to 10, Q2 = 1 to 90, Q3 = 1 to 90, Q23 = 0.1 to 20, and Q28 + Q2 + Q3 + Q23 = 100.)

A high molecular compound (P-24);

（式中、Ｑ２８=０．１〜１０、Ｑ４=１〜９０、Ｑ５=１〜９０、Ｑ２２=０．１〜２０であり、Ｑ２８＋Ｑ４＋Ｑ５＋Ｑ２２＝１００である。）

(In the formula, Q28 = 0.1-10, Q4 = 1-90, Q5 = 1-90, Q22 = 0.1-20, and Q28 + Q4 + Q5 + Q22 = 100.)

A high molecular compound (P-25);

（式中、Ｑ３２=０．１〜４０、Ｑ１１=１〜９０、Ｑ１２=１〜９０、Ｑ２７=０．１〜２０であり、Ｑ３２＋Ｑ１１＋Ｑ１２＋Ｑ２７＝１００である。）

(In the formula, Q32 = 0.1-40, Q11 = 1-90, Q12 = 1-90, Q27 = 0.1-20, and Q32 + Q11 + Q12 + Q27 = 100.)

A high molecular compound (P-26);

（式中、Ｑ３２=０．１〜４０、Ｑ６=１〜９０、Ｑ７=１〜９０、Ｑ２４=０．１〜２０であり、Ｑ３２＋Ｑ６＋Ｑ７＋Ｑ２４＝１００である。）

(In the formula, Q32 = 0.1-40, Q6 = 1-90, Q7 = 1-90, Q24 = 0.1-20, and Q32 + Q6 + Q7 + Q24 = 100.)

A high molecular compound (P-27);

（式中、Ｑ３２=０．１〜４０、Ｑ３=１〜９０、Ｑ１１=１〜９０、Ｑ２５=０．１〜２０、Ｑ２４=０．１〜２０であり、Ｑ３２＋Ｑ３＋Ｑ１１＋Ｑ２５＋Ｑ２４＝１００である。）

(In the formula, Q32 = 0.1-40, Q3 = 1-90, Q11 = 1-90, Q25 = 0.1-20, Q24 = 0.1-20, and Q32 + Q3 + Q11 + Q25 + Q24 = 100.)

A high molecular compound (P-28);

（式中、Ｑ３２=０．１〜４０、Ｑ４=１〜９０、Ｑ５=１〜９０、Ｑ２６=０．１〜２０であり、Ｑ３２＋Ｑ４＋Ｑ５＋Ｑ２６＝１００である。）

(In the formula, Q32 = 0.1 to 40, Q4 = 1 to 90, Q5 = 1 to 90, Q26 = 0.1 to 20, and Q32 + Q4 + Q5 + Q26 = 100.)

A high molecular compound (P-29);

（式中、Ｑ２８=０．１〜４０、Ｑ１７=１〜９０、Ｑ１１=１〜９０、Ｑ２５=０．１〜２０、Ｑ２４=０．１〜２０であり、Ｑ２８＋Ｑ１７＋Ｑ１１＋Ｑ２５＋Ｑ２４＝１００である。）

(In the formula, Q28 = 0.1-40, Q17 = 1-90, Q11 = 1-90, Q25 = 0.1-20, Q24 = 0.1-20, and Q28 + Q17 + Q11 + Q25 + Q24 = 100.)

A high molecular compound (P-30);

（式中、Ｑ２８=０．１〜２０、Ｑ１７=１〜９０、Ｑ１６=０．１〜２０、Ｑ８=１〜９０であり、Ｑ２８＋Ｑ１７＋Ｑ１６＋Ｑ８＝１００である。）

(In the formula, Q28 = 0.1-20, Q17 = 1-90, Q16 = 0.1-20, Q8 = 1-90, and Q28 + Q17 + Q16 + Q8 = 100.)

A high molecular compound (P-31);

（式中、Ｑ３０=０．１〜４０、Ｑ４=１〜９０、Ｑ２=１〜９０であり、Ｑ３０＋Ｑ４＋Ｑ２＝１００である。）

(In the formula, Q30 = 0.1 to 40, Q4 = 1 to 90, Q2 = 1 to 90, and Q30 + Q4 + Q2 = 100.)

A high molecular compound (P-32);

（式中、Ｑ３０=０．１〜４０、Ｑ３=１〜９０、Ｑ１１=１〜９０、Ｑ２５=０．１〜２０、Ｑ２４=０．１〜２０であり、Ｑ３０＋Ｑ３＋Ｑ１１＋Ｑ２５＋Ｑ２４＝１００である。）

(In the formula, Q30 = 0.1-40, Q3 = 1-90, Q11 = 1-90, Q25 = 0.1-20, Q24 = 0.1-20, and Q30 + Q3 + Q11 + Q25 + Q24 = 100.)

A high molecular compound (P-33);

（式中、Ｑ２９=０．１〜４０、Ｑ１１=１〜９０、Ｑ１２=１〜９０であり、Ｑ２９＋Ｑ１１＋Ｑ１２＝１００である。）

(In the formula, Q29 = 0.1 to 40, Q11 = 1 to 90, Q12 = 1 to 90, and Q29 + Q11 + Q12 = 100.)

A high molecular compound (P-34);

（式中、Ｑ２９=０．１〜２０、Ｑ６=１〜９０、Ｑ７=１〜９０、Ｑ１４=０．１〜２０であり、Ｑ２９＋Ｑ６＋Ｑ７＋Ｑ１４＝１００である。）

(In the formula, Q29 = 0.1-20, Q6 = 1-90, Q7 = 1-90, Q14 = 0.1-20, and Q29 + Q6 + Q7 + Q14 = 100.)

A high molecular compound (P-35);

（式中、Ｑ３１=０．１〜４０、Ｑ１７=１〜９０、Ｑ１１=１〜９０、Ｑ２５=０．１〜２０、Ｑ２４=０．１〜２０であり、Ｑ３１＋Ｑ１７＋Ｑ１１＋Ｑ２５＋Ｑ２４＝１００である。）

(In the formula, Q31 = 0.1-40, Q17 = 1-90, Q11 = 1-90, Q25 = 0.1-20, Q24 = 0.1-20, and Q31 + Q17 + Q11 + Q25 + Q24 = 100.)

A high molecular compound (P-36);

（式中、Ｑ３１=０．１〜２０、Ｑ１７=１〜９０、Ｑ１６=０．１〜２０、Ｑ９=１〜９０であり、Ｑ３１＋Ｑ１７＋Ｑ１６＋Ｑ９＝１００である。）

(In the formula, Q31 = 0.1-20, Q17 = 1-90, Q16 = 0.1-20, Q9 = 1-90, and Q31 + Q17 + Q16 + Q9 = 100.)

A high molecular compound (P-37);

（式中、Ｑ３２=０．１〜４０、Ｑ４=１〜９０、Ｑ２=１〜９０であり、Ｑ３２＋Ｑ４＋Ｑ２＝１００である。）

(In the formula, Q32 = 0.1 to 40, Q4 = 1 to 90, Q2 = 1 to 90, and Q32 + Q4 + Q2 = 100.)

A high molecular compound (P-38);

（式中、Ｑ３２=０．１〜４０、Ｑ３=１〜９０、Ｑ１１=１〜９０、Ｑ２５=０．１〜２０、Ｑ２４=０．１〜２０であり、Ｑ３２＋Ｑ３＋Ｑ１１＋Ｑ２５＋Ｑ２４＝１００である。）

(In the formula, Q32 = 0.1-40, Q3 = 1-90, Q11 = 1-90, Q25 = 0.1-20, Q24 = 0.1-20, and Q32 + Q3 + Q11 + Q25 + Q24 = 100.)

A high molecular compound (P-39);

（式中、Ｑ３４=０．１〜４０、Ｑ１１=１〜９０、Ｑ１２=１〜９０であり、Ｑ３４＋Ｑ１１＋Ｑ１２＝１００である。）

(In the formula, Q34 = 0.1 to 40, Q11 = 1 to 90, Q12 = 1 to 90, and Q34 + Q11 + Q12 = 100.)

A high molecular compound (P-40);

（式中、Ｑ３４=０．１〜２０、Ｑ６=１〜９０、Ｑ７=１〜９０、Ｑ１４=０．１〜２０であり、Ｑ３４＋Ｑ６＋Ｑ７＋Ｑ１１４＝１００である。）

(In the formula, Q34 = 0.1-20, Q6 = 1-90, Q7 = 1-90, Q14 = 0.1-20, and Q34 + Q6 + Q7 + Q114 = 100.)

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

  The polymer compound of the present invention can be produced, for example, by subjecting a compound represented by the following formula (a) to condensation polymerization.

（式（ａ）中、
Y¹は、ハロゲン原子（但し、フッ素原子は除く。）、−Ｂ（ＯＨ）_２、−ＢＦ_４ ⁻Ｑ（Ｑはリチウム、ナトリウム、カリウム、ルビジウムまたはセシウムの一価の陽イオンを示す。）で表される基、ボロン酸エステル残基、下記式（ａ−１）で表される基、下記式（ａ−２）で表される基、下記式（ａ−３）で表される基、または、下記式（ａ−４）を表す。２個存在するY¹は、同一であっても異なっていてもよい。
Ar^aおよびAr^ｂは、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表し、
Ar^ｃは、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
Ar^aおよびAr^bからなる群から選ばれる少なくともひとつが無置換もしくは置換のフェナントレンジイル基を表す。
Ar^ｄは、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基または無置換もしくは置換のアルキル基を表す。２個存在するAr^ｄは、同一であっても異なっていてもよい。）

(In the formula (a),
Y ¹ is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) A group represented by the following formula (a-2), a group represented by the following formula (a-2), a group represented by the following formula (a-3) Or the following formula (a-4). Two Y ¹ may be the same or different.
Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group;
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
At least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )

（式（ａ−１）中、Ｒ^Tは、無置換もしくは置換のアルキル基または無置換もしくは置換のアリール基を表す。）

(In the formula (a-1), R ^T represents an unsubstituted or substituted alkyl group or an unsubstituted or substituted aryl group.)

（式（ａ−２）中、Ｘ_Aは、ハロゲン原子を表す。）

(In formula (a-2), X _A represents a halogen atom.)

（式（ａ−３）中、Ｘ_Aは、前記と同じ意味を表す。）

(In formula (a-3), X _A represents the same meaning as described above.)

（式（ａ−４）中、R^Tは、前記と同じ意味を表す。）

(In formula (a-4), ^RT represents the same meaning as described above.)

  In the case where the polymer compound of the present invention contains at least one kind of structural unit selected from the group consisting of the structural unit represented by the formula (3) and the structural unit represented by the formula (4), for example, One or more compounds selected from the group consisting of a compound represented by the above formula (a), a compound represented by the following formula (b-1) and a compound represented by the following formula (b-2) Can be produced by condensation polymerization.

（式（ｂ−１）中、Ar⁵およびY¹は、前記と同じ意味を表す。）

(In formula (b-1), Ar ⁵ and Y ¹ represent the same meaning as described above.)

（式（ｂ−２）中、Ar⁶、Ar⁷、Ar⁸、Ｅ_１、Ｅ_２、Ｅ_３、a、ｐおよびY¹は、前記と同じ意味を表す。）

(In formula (b-2), Ar ⁶ , Ar ⁷ , Ar ⁸ , E ₁ , E ₂ , E ₃ , a, p and Y ¹ represent the same meaning as described above.)

In the formula (a), formula (b-1), formula (b-2), formula (a-2) and formula (a-3), examples of the halogen atom represented by Y ¹ and X _A include chlorine. An atom, a bromine atom, and an iodine atom are mentioned, It is preferable that it is a bromine atom.

Formula (a), In the formula (b-1) and formula ^{_{(b-2), -BF 4}} Y 1 represents - Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium. ) Includes groups represented by the following formulas.

In the formula (a), formula (b-1), and formula (b-2), examples of the boronic acid ester residue represented by Y ¹ include groups represented by the following formulas.

In formula (a-1), the definition and examples of the unsubstituted or substituted alkyl group represented by R ^T are the same as the definitions and examples of the unsubstituted or substituted alkyl group represented by Ar ^d described above.

In formula (a-1), the definition and example of the unsubstituted or substituted aryl group represented by R ^T are the same as the definition and example of the unsubstituted or substituted aryl group represented by Ar ^d described above.

  The group represented by the formula (a-1) may be referred to as a sulfonate group, and examples thereof include a methanesulfonate group, a trifluoromethanesulfonate group, a phenylsulfonate group, and a 4-methylphenylsulfonate group.

In the formula (a-4), the definition of the unsubstituted or substituted alkyl group and the unsubstituted or substituted aryl group represented by R ^T , for example, the unsubstituted or substituted alkyl group in Ar ^d described above and the unsubstituted or substituted group The definition and examples of the aryl group are the same as each other.

  The group represented by the formula (a-4) may be referred to as a stannanyl group, and examples thereof include a trimethylstannanyl group, a triethylstannanyl group, and a tributylstannanyl group.

  As the compounds represented by the formulas (a), (b-1) and (b-2), those synthesized and isolated in advance can be used, or they can be prepared in a reaction system and used as they are.

In the formulas (a), (b-1) and (b-2), Y ¹ represents a compound represented by the formula (a), a compound represented by the formula (b-1) and a formula (b-2). in terms of convenience and easy handling of the synthesis of the compound represented by a halogen atom, -B (OH) 2, -BF 4 - Q (Q is lithium, sodium, potassium, rubidium or cesium monovalent cation And a boronic acid ester residue.

  As a method of condensation polymerization, a compound represented by the formula (a), a compound represented by the formula (b-1) and a compound represented by the formula (b-2) are mixed with an appropriate catalyst or an appropriate base. And a reaction method.

  Examples of the catalyst used for the condensation polymerization include transition metal compounds. Specifically, palladium [tetrakis (triphenylphosphine)], [tris (dibenzylideneacetone)] dipalladium, palladium complexes such as palladium acetate, nickel [tetrakis (triphenylphosphine)], [1,3-bis ( Catalysts comprising transition metal complexes such as diphenylphosphino) propane] dichloronickel, [bis (1,4-cyclooctadiene)] nickel, and the like, and these complexes and triphenylphosphine, tri (tert-butyl) Phosphine), tricyclohexylphosphine, diphenylphosphinopropane, bipyridyl and other catalysts. As the catalyst, one synthesized in advance can be used, or one prepared in a reaction system can be used as it is. These catalysts may be used alone or in combination of two or more.

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

  Bases used for condensation polymerization include inorganic bases such as sodium carbonate, potassium carbonate, cesium carbonate, potassium fluoride, cesium fluoride, tripotassium phosphate, tetrabutylammonium fluoride, tetrabutylammonium chloride, tetrabutylammonium bromide And organic bases such as tetrabutylammonium hydroxide. These bases may be used alone or in combination of two or more.

  When a base is used, the amount used is the sum of the number of moles of the compound represented by formula (a), the compound represented by formula (b-1) and the compound represented by formula (b-2). 0.5 to 20 molar equivalents are preferable, and 1 to 10 molar equivalents are more preferable.

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

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

  The amount of the organic solvent used is such that the total concentration of the compound represented by formula (a), the compound represented by formula (b-1) and the compound represented by formula (b-2) is usually 0.1. The amount used is ˜90 wt%, preferably 1 to 50 wt%, more preferably 2 to 30 wt%.

  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 the reaction temperature, but is usually 1 hour or longer, preferably 2 to 500 hours.

Condensation polymerization is performed under anhydrous conditions when Y ¹ in formula (a), formula (b-1), and formula (b-2) is a group represented by formula (a-2). It is desirable.

  Condensation polymerization methods include polymerization by the Suzuki reaction (Chemical Review (Chem. Rev.), Vol. 95, page 2457 (1995)), polymerization by the Grignard reaction (Kyoritsu Shuppan, Polymer Functional Materials Series) Volume 2, Polymer Synthesis and Reaction (2), pp. 432-433), Polymerization by Yamamoto Polymerization (Prog. Polym. Sci.), Volume 17, pages 1153-1205, 1992).

  The post-treatment of the condensation polymerization can be performed by a known method such as a method of adding a reaction solution obtained by condensation polymerization to a lower alcohol such as methanol and filtering and drying the deposited precipitate.

  By the post-treatment, the polymer compound of the present invention can be obtained. However, when the purity of the polymer compound is low, it can be purified by usual methods such as recrystallization, continuous extraction with a Soxhlet extractor, column chromatography, etc. .

<Compound>
The compound of the present invention is a compound represented by the following formula (5), and can be suitably used as a raw material compound of the polymer compound of the present invention.

（式中、
LGは、ハロゲン原子（但し、フッ素原子は除く。）、−Ｂ（ＯＨ）_２、−ＢＦ_４ ⁻Ｑ（Ｑはリチウム、ナトリウム、カリウム、ルビジウムまたはセシウムの一価の陽イオンを示す。）で表される基、ボロン酸エステル残基、または、―O―SO₂―Zで表される基を表す。Zは、無置換もしくは置換のアルキル基またはアリール基を表す。２個存在するLGは、同一であっても異なっていてもよい。
Ar^aおよびAr^ｂは、それぞれ独立に、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表し、
Ar^ｃは、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
Ar^aおよびAr^bからなる群から選ばれる少なくともひとつが無置換もしくは置換のフェナントレンジイル基を表す。
Ar^ｄは、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基または無置換もしくは置換のアルキル基を表す。２個存在するAr^ｄは、同一であっても異なっていてもよい。）

(Where
LG is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - with Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) And a group represented by a boronic acid ester residue or —O—SO ₂ —Z. Z represents an unsubstituted or substituted alkyl group or aryl group. Two LGs may be the same or different.
Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group;
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
At least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )

  Since the compound represented by the formula (5) has good stability of the polymer compound according to the present embodiment and the light emission efficiency of the light emitting device using the polymer compound, the following formula (5) -2) is preferable, and a compound represented by the following formula (5-2-1) is more preferable.

（式中、
LG、Ar^ｃおよびAr^ｄは、前記と同じ意味を表す。
R^a、R^bおよびR^cは、それぞれ独立に、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基、無置換もしくは置換のアリールオキシ基、無置換もしくは置換のアルコキシ基または無置換もしくは置換のアルキル基を表す。R^a、R^bおよびR^cが複数存在する場合、それらはそれぞれ、同一であっても異なっていてもよい。
hおよびjは、それぞれ独立に、０〜4の整数を表し、iは、０〜２の整数を表す。２個存在するｈ、ｉおよびｊは、それぞれ、同一であっても異なっていてもよい。）

(Where
LG, Ar ^c and Ar ^d are as defined above.
R ^a , R ^b and R ^c are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. When there are a plurality of R ^a , R ^b and R ^c , they may be the same or different.
h and j each independently represents an integer of 0 to 4, and i represents an integer of 0 to 2. Two h, i, and j may be the same or different. )

（式中、
LG、Ar^ｃ、Ar^ｄ、R^a、R^b、R^cおよびｉは、前記と同じ意味を表す。
kおよびlは、それぞれ独立に、０〜3の整数を表す。）

(Where
LG, Ar ^c , Ar ^d , R ^a , R ^b , R ^c and i represent the same meaning as described above.
k and l each independently represents an integer of 0 to 3. )

LG represents a halogen atom (provided that a fluorine atom is _{excluded.), - BF 4 - Q} (. Q is lithium, sodium, potassium, represents a monovalent cation of rubidium or cesium) a group represented by the boronic acid definition of the ester residue, examples are a halogen atom represented by Y ¹ in the above (however, the fluorine atom is _{excluded.), - BF 4 - Q} (Q is lithium, sodium, potassium, rubidium or cesium monovalent cation And the definition of the boronic acid ester group and examples are the same.

The definition and example of the group represented by —O—SO ₂ —Z represented by LG are the same as the definition and example of the above formula (a-1).

  A definition of a method for producing a polymer compound, which includes a step of polymerizing a compound represented by the formula (5) and uses a transition metal compound as a catalyst, an example is the compound represented by the above formula (a). This is the same as the definition and example of a method for producing a polymer compound, which comprises a step of polymerizing and uses a transition metal compound as a catalyst.

<Method for producing compound>
The compound represented by the above formula (5) is represented by the following formula (8) including a step of reacting a compound represented by the following formula (6) and a compound represented by the following formula (7). It can be obtained by a method for producing a compound.

Ar^eは、無置換もしくは置換のアリーレン基または無置換もしくは置換の二価の複素環基を表す。
LGは、ハロゲン原子（但し、フッ素原子は除く。）、−Ｂ（ＯＨ）_２、−ＢＦ_４ ⁻Ｑ（Ｑはリチウム、ナトリウム、カリウム、ルビジウムまたはセシウムの一価の陽イオンを示す。）で表される基、ボロン酸エステル残基、または、―O―SO₂―Zで表される基を表す。Zは、無置換もしくは置換のアルキル基またはアリール基を表す。２個存在するLGは、同一であっても異なっていてもよい。）
（式（７）中、
Ar^ｃは、無置換もしくは置換のアリーレン基、無置換もしくは置換の二価の複素環基、または、無置換もしくは置換のアリーレン基および無置換もしくは置換の二価の複素環基からなる群から選ばれる２以上の基が連結した２価の基を表し、
Ar^ｄは、水素原子、無置換もしくは置換のアリール基、無置換もしくは置換の一価の複素環基または無置換もしくは置換のアルキル基を表す。２個存在するAr^ｄは、同一であっても異なっていてもよい。）
（式（８）中、
Ar^ｃ、Ar^ｄ、Ar^ｅおよびLGは、前記と同じ意味を表す。２個存在するAr^ｄ、Ar^ｅおよびLGはそれぞれ、同一であっても異なっていてもよい。
但し、２個存在するAr^eの少なくともひとつは、無置換もしくは置換のフェナントレンジイル基を表す。）

Ar ^e represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
LG is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - with Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) And a group represented by a boronic acid ester residue or —O—SO ₂ —Z. Z represents an unsubstituted or substituted alkyl group or aryl group. Two LGs may be the same or different. )
(In formula (7),
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )
(In Formula (8),
Ar ^c , Ar ^d , Ar ^e and LG have the same meaning as described above. Two Ar ^d , Ar ^e and LG may be the same or different.
However, at least one of the two existing Ar ^e represents an unsubstituted or substituted phenanthrene diyl group. )

Defining unsubstituted or arylene group and an unsubstituted or substituted substituted divalent heterocyclic group represented by Ar ^e, example, Ar ^a and Ar ^b represents an unsubstituted or substituted arylene group and an unsubstituted or substituted two The definition of the valent heterocyclic group is the same as in the examples, and the light emission efficiency of the light emitting device obtained using the polymer compound is further improved. Therefore, an unsubstituted or substituted arylene group is preferable, and is represented by the formula 2-008. More preferred are phenanthrene diyl groups.

  In the method for producing a compound of the present invention, the reaction between the compound represented by formula (6) and the compound represented by formula (7) is carried out in the presence of palladium and / or a palladium compound (functioning as a catalyst). Preferably it is done. Here, the palladium compound refers to a palladium complex or palladium carbon supported on a carrier, but from the viewpoint of the yield of the compound represented by formula (8), in the presence of the palladium complex. Preferably it is done.

  Specific examples of the palladium complex include, for example, palladium acetate, [tris (dibenzylideneacetone)] dipalladium, bis (dibenzylideneacetone) palladium, palladium chloride, bis (acetonitrile) dichloropalladium, bis (benzonitrile) dichloropalladium, Palladium [tetrakis (triphenylphosphine)] is preferable, preferably palladium acetate, [tris (dibenzylideneacetone)] dipalladium, bis (dibenzylideneacetone) palladium, palladium chloride, bis (acetonitrile) dichloropalladium, bis (benzo Nitrile) dichloropalladium, 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex, 1,1'-bis (diphenylphosphino) ferrocene -Palladium (II) dichloride, more preferably palladium acetate, [tris (dibenzylideneacetone)] dipalladium, bis (dibenzylideneacetone) palladium, more preferably bis (ton) palladium, bis (benzonitrile) Dichloropalladium, 1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride-dichloromethane complex, 1,1′-bis (diphenylphosphino) ferrocene-palladium (II) dichloride.

  As these catalysts, those synthesized in advance may be used, or those prepared in the reaction system may be used as they are. Moreover, these catalysts may be used individually by 1 type, or may use 2 or more types together.

  In addition to palladium and / or a palladium compound, 1,1′-bis (diphenylphosphino) ferrocene is preferably used in combination from the viewpoint of suppressing side reactions.

  The amount of palladium and / or palladium compound is usually preferably 0.00001 to 3 equivalents, more preferably 0.0001 to 1 equivalents relative to the number of moles of LG in the compound represented by formula (6). More preferably, it is 0.001-0.5 equivalent, Most preferably, it is 0.005-0.1 equivalent.

  The palladium and / or the palladium compound, and the compound represented by the formula (6) and the compound represented by the formula (7) may be used as a solution (or suspension) prepared in advance only with these and a solvent. Good.

  In the method for producing a compound of the present invention, the reaction is carried out in the presence of a base in addition to palladium and / or a palladium compound, a compound represented by formula (6), and a compound represented by formula (7). Is preferred. Preferred bases include metal alkoxides. Examples of the metal alkoxide include sodium tert-butoxide, potassium tert-butoxide, and the like, and sodium tert-butoxide is more preferable.

  The amount of the base used is usually preferably 0.1 to 20 equivalents, more preferably 0.5 to 10 equivalents, relative to the number of moles of the reactive group of the aromatic compound having the reactive group as a raw material. And more preferably 0.9 to 4 equivalents.

  In the manufacturing method of the compound of this invention, it is preferable to react in presence of an organic solvent, and the organic solvent to be used may be used individually by 1 type, or may use 2 or more types together. Examples of the organic solvent include toluene, xylene (o-xylene, m-xylene, p-xylene, and mixtures thereof), mesitylene, p-cymene, ethylbenzene, chlorobenzene, nitrobenzene, tetrahydrofuran, 1,4-dioxane. THF, preferably toluene, xylene, mesitylene, ethylbenzene, chlorobenzene, nitrobenzene, THF, more preferably toluene, xylene, mesitylene, THF, and more preferably toluene and xylene, from the viewpoint of suppressing side reactions. A mixed solvent of THF, a mixed solvent of xylene and THF, and a mixed solvent of xylene and THF is particularly preferable. Of the xylenes, o-xylene is preferred. In order to suppress side reactions, the organic solvent is desirably subjected to deoxygenation treatment.

  When the organic solvent used in the method for producing a compound of the present invention is a two-type mixed solvent using THF in combination, THF has a volume ratio of 1 to 0.1 with respect to an organic solvent other than THF from the viewpoint of suppressing side reactions. It is preferable to use at a double ratio, and more preferable to use at a volume ratio of 0.6 to 0.1.

  From the viewpoint of the solubility of the compound represented by formula (6) and the compound represented by formula (7) in the organic solvent, the amount of the organic solvent used is based on the weight of the compound represented by formula (6). Preferably it is 0.1-100 weight times, More preferably, it is 1-50 weight times, More preferably, it is 10-40 weight times.

  The manufacturing method of the compound of this invention uses 2-20 equivalent of compounds represented by Formula (6) with respect to the number of moles of the compound represented by Formula (7) from a viewpoint of suppressing a side reaction. Preferably, 2 to 10 equivalents are used more preferably, and 4 to 6 equivalents are more preferably used.

  In the production method of the compound of the present invention, the reaction temperature is preferably 0 ° C. to 250 ° C., more preferably 25 ° C. to 200 ° C., further preferably 80 ° C. to 150 ° C., particularly preferably 100 ° C. ~ 135 ° C.

  In the method for producing the compound of the present invention, the reaction time depends on conditions such as the reaction temperature, but is usually 1 hour or longer, preferably 2 to 500 hours, more preferably 2 to 24 hours.

  In the method for producing the compound of the present invention, the reaction is preferably performed under anhydrous conditions.

<Composition>
The first 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.

  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 content ratio of 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 may be determined according to the use, but the use of the light emitting material In this case, the weight of the polymer compound of the present invention is usually 20 to 99 parts by weight, preferably 40 to 95 parts by weight with respect to 100 parts by weight of the whole composition.

  The second composition of the present invention is a liquid composition containing the polymer compound of the present invention and a solvent. This liquid 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 a coating method such as an inkjet printing method. In addition to the polymer compound and solvent of the present invention, the solution of the present invention contains 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 low molecular weight compound for decreasing the viscosity, a surfactant (for decreasing the surface tension), and an antioxidant.

  The ratio of the polymer compound of the present invention in the solution of the present invention is usually 0.1 to 99.9 parts by weight, preferably 0.1 to 10 parts by weight, with respect to 100 parts by weight of the solution. More preferably, it is 0.2-7 weight part, More preferably, it is 0.5-2 weight part.

  The viscosity of the solution of the present invention may be adjusted according to the type of coating method, but in the case of a solution such as an ink jet printing method passing through a discharge device, in order to prevent clogging and flight bending at the time of discharge, In 25 degreeC, it is preferable that it is the range of 1-20 mPa * s.

  The high molecular weight compound used as the thickener is not particularly limited as long as it is soluble in the same solvent as the high molecular compound of the present invention and does not inhibit light emission or charge transport. 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 parts by weight or less, and more preferably 30 parts by weight or less with respect to 100 parts by weight 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 of the present invention and does not inhibit light emission or charge transport, and 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 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, ether solvents such as tetrahydrofuran, dioxane and anisole, toluene and xylene. Aromatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone Ketone solvents such as cyclohexanone, benzophenone and acetophenone, ester solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate and phenyl acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol Polyethyl alcohol, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol and other polyhydric alcohols and derivatives thereof, methanol, ethanol, propanol, isopropanol And alcohol solvents such as 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. Among these, from the viewpoints of solubility of the polymer compound of the present invention, uniformity during film formation, viscosity characteristics, etc., aromatic hydrocarbon solvents, ether solvents, aliphatic hydrocarbon solvents, ester solvents Ketone solvents are preferred, toluene, xylene, ethylbenzene, diethylbenzene, trimethylbenzene, n-propylbenzene, isopropylbenzene, n-butylbenzene, isobutylbenzene, s-butylbenzene, n-hexylbenzene, cyclohexylbenzene, 1-methyl. Naphthalene, tetralin, anisole, ethoxybenzene, cyclohexane, bicyclohexyl, cyclohexenylcyclohexanone, n-heptylcyclohexane, n-hexylcyclohexane, decalin, methyl benzoate, cyclohexanone, 2-propylcyclohexa Down, 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, 2-nonanone, 2-decanone, dicyclohexyl ketone, acetophenone, benzophenone more preferable.

  The solvent contained in the solution of the present invention is preferably used in combination of two or more types, more preferably in combination of two or three types, and in combination of two types, from the viewpoint of manufacturing a light emitting device. Particularly preferred.

  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. From the viewpoint of film formability, one kind of solvent is preferably a solvent having a boiling point of 180 ° C. or higher, and more preferably 200 ° C. or higher. From the viewpoint of viscosity, it is preferable that the polymer compound of the present invention is dissolved in both of the two solvents at a concentration of 1% by weight or more at 60 ° C. The polymer compound of the present invention is preferably dissolved at a concentration of 1% by weight or more at 25 ° C.

  When two or more solvents are contained in the solution of the present invention, the solvent having the highest boiling point is preferably 40 to 90% by weight of the total solvent weight in the solution from the viewpoint of viscosity and film formability. 50 to 90% by weight, more preferably 65 to 85% by weight.

  The polymer compound of the present invention contained in the solution of the present invention may be one type or two or more types, and may contain a high molecular weight compound other than the polymer compound as long as the light emitting device characteristics and the like are not impaired.

  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. Further, 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 is formed by using the polymer compound of the present invention, and includes the polymer compound of the present invention as it is, and the polymer compound of the present invention is intramolecular and / or intermolecular. There exists an aspect formed by bridge | crosslinking. The organic thin film of the present invention is, for example, a light-emitting thin film, a conductive thin film, or an organic semiconductor thin film.

  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 prepared by flexographic printing, offset printing, ink jet printing, capillary-coating, nozzle coating, screen printing, flexographic printing, offset printing, ink jet printing, more preferably ink jet printing. It can be produced by the method.

  When an organic thin film is produced using the solution of the present invention, the polymer compound of the present invention contained in the solution has a high glass transition temperature, and thus can be heated at a temperature of 100 ° C. or higher, and a temperature of 130 ° C. Even when heated at, the degradation of the light emitting element characteristics is small. Moreover, depending on the kind of the high molecular compound of this invention, it can also heat at the temperature of 160 degreeC or more.

  The light-emitting thin film preferably has a light emission quantum yield of 30% or more, more preferably 50% or more, and still more preferably 60% or more, from the viewpoint of the luminance and light emission voltage of the light-emitting element. 70% or more is particularly preferable.

  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 also be fabricated by forming the 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 including an electrode composed of an anode and a cathode and an organic layer provided between the electrodes, and the organic layer contains the polymer compound of the present invention as it is. Embodiments include an embodiment in which the polymer compound of the present invention is crosslinked within a molecule and / or between molecules.

  The organic layer 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, and more preferably a light emitting layer. .

  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 plays a role of separating the light emitting layer and the anode, or the light emitting layer and the hole injection layer or the hole transport layer. It is a layer that plays a role of isolating the above. 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 and the electron injection layer may be composed of only one layer or two or more layers.

  When the organic layer containing the polymer compound of the present invention is a light emitting layer, the light emitting layer further contains a hole transport material, an electron transport material, a light emitting material, an additive for increasing the luminance life of the light emitting element, and the like. You may go out. Here, the light emitting material means a material exhibiting fluorescence and / or phosphorescence (excluding the polymer compound of the present invention).

  When the organic layer containing the polymer compound of the present invention contains the polymer compound of the present invention and a hole transport material, the total amount of the polymer compound of the present invention and the hole transport material is 100 parts by weight. The ratio of the hole transport material is usually 1 to 80 parts by weight, preferably 5 to 60 parts by weight.

  When the organic layer containing the polymer compound of the present invention contains the polymer compound of the present invention and an electron transport material, the electrons with respect to a total of 100 parts by weight of the polymer compound of the present invention and the electron transport material. The ratio of the transport material is usually 1 to 80 parts by weight, preferably 5 to 60 parts by weight.

  When the organic layer containing the polymer compound of the present invention contains the polymer compound of the present invention and a luminescent material, the amount of the luminescent material with respect to a total of 100 parts by weight of the polymer compound of the present invention and the luminescent material. The ratio is usually 1 to 80 parts by weight, preferably 5 to 60 parts by weight.

  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, JP-A-9-45478 discloses polymers and copolymers having a fluorenediyl group as a structural unit (hereinafter referred to as “(co) polymer”), and arylene groups as a structural unit (a common unit). ) A polymer, a (co) polymer having an arylene vinylene group as a structural unit, a divalent aromatic amine group as a structural unit Like to (co) polymer and the like and.

  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. .

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

  As additives, 2,2′-bipyridyl, 3,3′-bipyridyl, bipyridyl such as 4,4′-bipyridyl, 4-methyl-2,2′-bipyridyl, 5-methyl-2,2′-bipyridyl And bipyridyl derivatives such as 5,5′-dimethyl-2,2′-bipyridyl.

  The film thickness of the light-emitting layer varies depending on the material used, and may be selected so that the driving voltage and the light emission efficiency are moderate values, but is usually 1 nm to 1 μm, preferably 2 nm to 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 printing methods, offset printing methods, ink jet printing methods, capillary coating methods, and nozzle coating methods can be used. From the viewpoint of ease of pattern formation and multicolor coating, screen printing methods, flexographic methods, etc. Printing methods such as a printing method, an offset printing method, and an ink jet printing method are preferable.

  The light emitting device of the present invention includes a light emitting device in which an electron transport layer is provided between the cathode and the light emitting layer, a light emitting device in which a hole transport layer is provided between the anode and the light emitting layer, and a space between the cathode and the light emitting layer. And a light emitting element in which an electron transport layer is provided and a hole transport layer is provided between the anode and the light emitting layer.

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 the present invention has a hole transport layer, the hole transport layer usually contains the hole transport material (a high molecular weight compound, a low molecular weight compound). Examples of the hole transport material include polyvinyl carbazole 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, Those described in JP-A-63-175860, JP-A-2-135359, JP-A-2-135361, JP-A-2-209988, JP-A-3-37992, JP-A-3-152184, etc. Illustrated.

  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 its derivatives, poly (2,5-thienylene vinylene) and its derivatives, etc. are preferred, polyvinyl carbazole and its derivatives, polysilane and its derivatives, poly having aromatic amine in the side chain or main chain Siloxane derivatives are more preferred.

  Among these, as low molecular weight compounds, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, and triphenyldiamine derivatives 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. 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, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, and polysiloxane.

  Polyvinylcarbazole and derivatives thereof are obtained, for example, from a vinyl monomer by cation polymerization or radical polymerization.

  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, the methods described in these can be used, but the Kipping method is particularly preferably used.

  Since polysiloxane and its derivatives have almost no hole transporting property in the siloxane skeleton structure, a compound having the structure of the low molecular weight hole transporting material in the side chain or main chain is preferable, and the hole transporting aromatic compound is preferable. A compound having an amine in the side chain or main chain is more preferable.

  As a film formation method of the hole transport layer, when a low molecular weight compound is used, a method by film formation from a mixed solution with a polymer binder is exemplified, and when a high molecular weight compound is used, a solution is formed. The method by film formation from is illustrated.

  As a solvent used for film formation from a solution, a solvent capable of dissolving or uniformly dispersing the hole transport material is preferable. Examples of the solvent 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 and the like. Aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, cyclohexanone Such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether Polyhydric alcohols and derivatives thereof such as ethylene, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol, dimethyl Examples include sulfoxide solvents such as 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 film thickness of the hole transport layer varies depending on the material used, and it may be selected so that the driving voltage and the luminous efficiency are appropriate values, but it needs a thickness that does not cause pinholes. If it is too thick, the driving voltage of the light emitting element becomes high, which is not preferable. Therefore, the film thickness of the hole transport layer is usually 1 nm to 1 μm, preferably 2 to 500 nm, and more preferably 5 to 200 nm.

  When the light-emitting device of the present invention has an electron transport layer, the electron transport layer usually contains the electron transport material (a high molecular weight compound, a low molecular weight compound). As the electron transporting material, known materials can be used, but oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and Derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, polyfluorene and derivatives thereof, etc. -70257, JP-A-63-175860, JP-A-2-135359, JP-A-2-135361, JP-A-2-209998, JP-A-3-37992 And compounds described in JP-A-3-152184, such as oxadiazole derivatives, benzoquinone and derivatives thereof, anthraquinone and derivatives thereof, 8-hydroxyquinoline and metal complexes of derivatives thereof, polyquinoline and derivatives thereof, poly Quinoxaline and derivatives thereof, polyfluorene and derivatives thereof are preferred, and 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8- Quinolinol) aluminum and polyquinoline are more preferred.

  As a method for forming the electron transport layer, when a low molecular weight compound is used, a vacuum deposition method from powder or a method by film formation from a solution or a molten state is exemplified, and when a high molecular weight compound is used. Examples of the method include film formation from a solution or a molten state. In the method of 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. Examples of the solvent 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 and the like. Aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, cyclohexanone Such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether Polyhydric alcohols and derivatives thereof such as ethylene, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol, dimethyl Examples include sulfoxide solvents such as 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 film 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. If it is thick, the driving voltage of the light emitting element increases, which is not preferable. Therefore, the film thickness of the electron transport layer is usually 1 nm to 1 μm, preferably 2 to 500 nm, and more preferably 5 to 200 nm.

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

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

  The order and number of layers to be stacked and the thickness of each layer may be adjusted in consideration of luminous efficiency and luminance life.

In the present invention, as a light emitting device provided with a charge injection layer (electron injection layer, hole injection layer), a light emitting device provided with a charge injection layer adjacent to the cathode, and a charge injection layer provided adjacent to the anode. A light emitting element is mentioned. 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, and is provided between the anode and the hole transport layer and has an ionization potential that is an intermediate value between the anode material and the hole transport material contained in the hole transport layer. Examples thereof include a layer containing a material, a layer provided between a cathode and an electron transport layer, and a layer containing a material having an electron affinity of an intermediate value between the cathode material and the electron transport material contained 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 a leakage current between the light emitting pixels. for the smaller is more preferably ^{1 × 10 -5 ~1 × 10 2} S / cm, 1 × 10 -5 ~1 × 10 1 S / cm is more preferable. Usually, in order to set 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, camphor sulfonate ion and the like, and 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 material of the electrode and the adjacent layer. Polyaniline and its derivatives, polythiophene and its derivatives, polypyrrole and its derivatives, polyphenylene vinylene and its derivatives, polythienylene vinylene And derivatives thereof, polyquinoline and derivatives thereof, polyquinoxaline and derivatives thereof, 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 the 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 the 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.

  Regarding the structure in which the interlayer layer is applied to the structures a) to ab), the interlayer layer is provided between the anode and the light emitting layer, and the anode, the hole injection layer or the hole transport layer, and the light emitting layer. It is preferably composed of a material having an ionization potential intermediate to that of the polymer compound constituting

  Examples of the material used for the interlayer layer include polymers containing aromatic amines such as polyvinyl carbazole and derivatives thereof, polyarylene derivatives having an aromatic amine in the side chain or main chain, arylamine derivatives, and triphenyldiamine derivatives.

  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. Examples of the solvent 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 and the like. Aromatic hydrocarbon solvents, cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane and other aliphatic hydrocarbon solvents, acetone, methyl ethyl ketone, cyclohexanone Such as ketone solvents, ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxy ether Polyhydric alcohols and derivatives thereof such as ethylene, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, alcohol solvents such as methanol, ethanol, propanol, isopropanol, cyclohexanol, dimethyl Examples include sulfoxide solvents such as 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 film 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, and is usually 1 nm to 1 μm, preferably 2 to 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 light-emitting element. is there. When the light emitting layer is formed by the coating method after the interlayer layer is formed by the coating method, as a method for reducing the mixing of the two layers of materials, the interlayer layer is formed by the coating method and the 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, the 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. Furthermore, the number of polymerizable groups is preferably 5% or more with respect to the number of structural units in the molecule.

  The substrate on which the light emitting element of the present invention is formed may be any substrate that does not change when an electrode is formed and an organic layer is formed, and examples thereof include materials made of materials such as glass, plastic, polymer film, and silicon. The 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 device of the present invention is usually transparent or translucent, but the anode side is preferably transparent or translucent.

  Examples of the material of the anode include a conductive metal oxide film, a translucent metal thin film, and the like. Specifically, indium oxide, zinc oxide, tin oxide, and a composite thereof such as indium / tin / Films (NESA, etc.) made using conductive compounds made of oxide (ITO), indium, zinc, oxide, etc., gold, platinum, silver, copper, etc. are used, ITO, indium, zinc, oxide, tin oxide Is preferred. 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 derivatives thereof, polythiophene and derivatives thereof may be used. 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 electrical conductivity, and is, for example, 10 nm to 10 μm, preferably 20 nm to 1 μm, and more preferably 40 to 500 nm. .

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

  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, calcium-aluminum alloy and the like. The cathode may have a laminated structure of two or more layers.

  The film thickness of the cathode may be adjusted in consideration of electric conductivity and durability, and is usually 10 nm to 10 μm, preferably 20 nm to 1 μm, and 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 film 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 low water permeability treatment on the surface, or the like can be used. The protective cover is bonded to the element substrate with a thermosetting resin or a photocurable resin and sealed. The method 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 gas or argon gas is sealed in the space, oxidation of the cathode can be prevented, and further, a desiccant such as barium oxide is adsorbed in the manufacturing process by installing in the space. It becomes easy to suppress a minute amount of moisture entering through moisture or a cured resin from damaging the device. Among these, it is preferable to take one or more measures.

  The light emitting device of the present invention 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 of the present invention, the planar anode and 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 one of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display element capable of displaying numbers, letters, simple symbols and the like can be obtained. Further, in order to obtain a dot matrix element, both the anode and the cathode may be formed in a stripe shape and arranged so as to be orthogonal to each other. Partial color display and multi-color display are possible by a method of separately coating a plurality of types of polymeric fluorescent substances having different emission colors or a method using a color filter or a fluorescence conversion filter. The dot matrix element can be driven passively, or may be actively driven in combination with a TFT or the like. These display elements can be used in display devices such as 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 in detail, this invention is not limited to these.

  In this example, the polystyrene-equivalent number average molecular weight and weight average molecular weight were determined by gel permeation chromatography (GPC, Shimadzu Corporation, trade name: LC-10Avp). The polymer compound to be measured was dissolved in tetrahydrofuran 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.

  In this example, unless otherwise specified, NMR measurement is performed by dissolving 5 to 20 mg of a measurement sample in about 0.5 mL of an organic solvent, NMR (manufactured by Varian, Inc., trade name: MERCURY). 300).

<Synthesis Example 1> (Synthesis of Compound M-4)

  After making the gas in the reaction vessel an argon gas atmosphere, N-phenyl-N- (4-tert-butyl) -2,6-dimethylphenylamine (13 g, 73.9 mmol), tris (dibenzylideneacetone) dipalladium (0) (451 mg, 0.50 mmol), tri-tert-butylphosphonium tetrafluoroborate (572 mg, 1.97 mmol), sodium tert-butoxide (9.5 g, 98.5 mmol) and toluene (120 mL) were mixed. And heated to reflux. Thereafter, 4,4′-diiodobiphenyl (10 g, 24.6 mmol) was added in 5 portions, and then the mixture was further heated under reflux for 1 hour. Water was added to the obtained reaction solution, and the organic layer was washed. Then, hexane was added to the obtained organic layer, followed by filtration to obtain Compound M-3 (8.8 g, yield 71%, purity 98.8%).

  After making the gas in the reaction vessel an argon atmosphere, Compound M-3 (8.2 g, 16.2 mmol), 2,7-dibromophenanthrene (21.8 g, 64.7 mmol), tris (dibenzylideneacetone) dipalladium (0) (296 mg, 0.32 mmol), 1,1′-bis (diphenylphosphino) ferrocene (718 mg, 1.3 mmol), sodium tert-butoxide (6.2 g, 37.8 mmol) and xylene (324 mL). The mixture was mixed and heated and stirred at 135 ° C. for 24 hours. Water was added to the obtained reaction solution, and the organic layer was washed. Thereafter, the solvent of the obtained organic layer was distilled off under reduced pressure. The resulting reaction mixture was purified by column chromatography (alumina gel, developing solvent: methylene chloride / hexane = 1/20) to obtain Compound M-4 (4.0 g, yield 24%, purity 99%). . Thereafter, recrystallization was performed using a mixed solvent of THF and acetonitrile to improve purity, and 935 mg of Compound M-4 was obtained with a purity of 99.5%. The yield was 6%.

¹ H-NMR (270 MHz, CDCl ₃ ): δ (ppm) = 1.38 (s, 18H), 2.09 (s, 12H), 7.12-7.16 (m, 8H), 7.32 (S, 2H), 7.42 (d, 2H), 7.48 (d, 4H), 7.53 (s, 4H), 7.66 (s, 4H), 7.95 (s, 2H) , 8.38 (d, 2H).

<Synthesis Example 2> (Synthesis of Compound M-6)

  After making the gas in the reaction vessel an argon gas atmosphere, N-phenyl-N- (4-tert-butyl) -2,6-dimethylphenylamine (10 g, 30.3 mmol), tris (dibenzylideneacetone) dipalladium (0) (555 mg, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (704 mg, 2.42 mmol), sodium tert-butoxide (14.6 g, 151.6 mmol) and toluene (60 mL). Mix and heat to reflux. Thereafter, 4,4′-diiodobenzene (10 g, 24.6 mmol) was added in 5 portions, and then the mixture was further heated under reflux for 1 hour. Water was added to the obtained reaction solution, and the organic layer was washed. Thereafter, hexane was added to the obtained organic layer, followed by filtration to obtain Compound M-5 (6.2 g, yield 59%, purity 99.6%).

  After making the gas in the reaction vessel an argon gas atmosphere, Compound M-5 (3.2 g, 7.5 mmol), 2,7-dibromophenanthrene (15.2 g, 45.2 mmol), Tris (dibenzylideneacetone) Di-palladium (0) (138 mg, 0.15 mmol), 1,1′-bis (diphenylphosphino) ferrocene (334 mg, 0.60 mmol), sodium tert-butoxide (2.9 g, 30.1 mmol), xylene (90 mL) ) And THF (60 mL) were mixed and heated and stirred at 105 ° C. for 2 hours. Water was added to the obtained reaction solution, and the organic layer was washed. Thereafter, the solvent of the obtained organic layer was distilled off under reduced pressure. The resulting reaction mixture was purified by column chromatography (alumina gel, developing solvent: methylene chloride / hexane = 1/20) to obtain compound M-6 (4.5 g, yield 63%, purity 99%). . Then, recrystallization was performed using a mixed solvent of THF and acetonitrile to improve purity, and 2.5 g of Compound M-6 was obtained with a purity of 99.9%. The yield was 35%.

¹ H-NMR (270 MHz, THF-d ₈ ): δ (ppm) = 1.41 (s, 18H), 2.16 (s, 12H), 7.09 (s, 4H), 7.16-7 .33 (m, 6H), 7.41 (d, 2H), 7.58-7.65 (m, 4H), 7.72 (d, 2H), 8.05 (d, 2H), 8. 56-8.59 (m, 4H).

<Synthesis Example 3> (Synthesis of Compound 5-a)

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

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

<Synthesis Example 4> (Synthesis of Compound 5-b)

反応容器内をアルゴンガス気流下とし、化合物５−ａ（２７．７ｇ）およびトリフルオロ酢酸（３６ｍｌ）を加えた。得られた溶液に対して、トリメチルシラン（８．４ｍｌ）およびヘキサン（２５ｍｌ）の混合溶液を３０分間かけて滴下し、室温にて一晩撹拌した。その後、得られた反応溶液を１０℃に冷却し、ヘキサンと蒸留水を加え、１時間撹拌した後、分液を行った。その後、水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、濃縮することで溶媒を除去した。その後、得られた残渣をメタノールで洗浄することにより、目的とする化合物５−ｂ（１２．１ｇ）を得た。

The inside of the reaction vessel was placed under an argon gas stream, and compound 5-a (27.7 g) and trifluoroacetic acid (36 ml) were added. To the resulting solution, a mixed solution of trimethylsilane (8.4 ml) and hexane (25 ml) was added dropwise over 30 minutes and stirred overnight at room temperature. Thereafter, the obtained reaction solution was cooled to 10 ° C., hexane and distilled water were added, and the mixture was stirred for 1 hour, followed by liquid separation. Then, water was added and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent, and concentrated to remove the solvent. Then, the target compound 5-b (12.1g) was obtained by wash | cleaning the obtained residue with methanol.

<Synthesis Example 5> (Synthesis of Compound 5-c)

反応容器内をアルゴンガス気流下とし、化合物５−ｂ（１２．０ｇ）、ジメチルスルホキシド（６０ｍｌ）、水（２ｍｌ）および水酸化カリウム（４．８５ｇ）を加えた。得られた溶液にヨウ化メチル（４．１ｍｌ）を滴下し、室温にて一晩撹拌した。その後、得られた反応溶液に対して、室温においてヘキサンおよび蒸留水を加え、１時間撹拌した後、分液を行った。その後、得られた油層に水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、得られた残渣をメタノールおよび酢酸ブチルを用いて再結晶することにより、目的とする化合物５−ｃ（４．３ｇ）を得た。

The reaction vessel was placed under an argon gas stream, and compound 5-b (12.0 g), dimethyl sulfoxide (60 ml), water (2 ml) and potassium hydroxide (4.85 g) were added. Methyl iodide (4.1 ml) was added dropwise to the resulting solution and stirred overnight at room temperature. Thereafter, hexane and distilled water were added to the obtained reaction solution at room temperature, and the mixture was stirred for 1 hour, followed by liquid separation. Then, water was added to the obtained oil layer and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Then, the target compound 5-c (4.3g) was obtained by recrystallizing the obtained residue using methanol and butyl acetate.

<Synthesis Example 6> (Synthesis of Compound 5)

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

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

<Synthesis Example 7> (Synthesis of Compound 6-a)

反応容器内をアルゴンガス雰囲気とし、３−ｎ−ヘキシルブロモベンゼン（１１１．１ｇ）およびテトラヒドロフランを加え、均一溶液を調製し、−７５℃まで冷却した。得られた溶液に２．５Ｍのｎ−ブチルリチウム／ヘキサン溶液（１−ブロモ−３，５−ジ−ｎ−ヘキシルベンゼンに対して１モル当量）（１７６ｍｌ）を−７５℃で１．５時間かけて滴下し、得られた溶液をさらに−７０℃で１．５時間撹拌した。その後、２，７−ジブロモフルオレノン（１４２ｇ）およびテトラヒドロフランからなる溶液を−７５℃で１時間かけて滴下し、得られた反応溶液を室温まで昇温させた後、４時間撹拌した。その後、得られた溶液を０℃まで冷却し、アセトンおよび２ｍｏｌ％塩酸水をゆっくり加え撹拌した後、室温まで昇温し、室温にて静置した。その後、得られた反応液をろ過し、ろ液を濃縮し、ヘキサンおよび水を加え撹拌し、分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、化合物６−ａ（１６２ｇ）を得た。

The reaction vessel was filled with an argon gas atmosphere, and 3-n-hexyl bromobenzene (111.1 g) and tetrahydrofuran were added to prepare a homogeneous solution and cooled to -75 ° C. To the resulting solution was added 2.5M n-butyllithium / hexane solution (1 molar equivalent to 1-bromo-3,5-di-n-hexylbenzene) (176 ml) at -75 ° C for 1.5 hours. The resulting solution was further stirred at -70 ° C for 1.5 hours. Thereafter, a solution consisting of 2,7-dibromofluorenone (142 g) and tetrahydrofuran was added dropwise at −75 ° C. over 1 hour, and the resulting reaction solution was warmed to room temperature and stirred for 4 hours. Thereafter, the resulting solution was cooled to 0 ° C., slowly added with acetone and 2 mol% aqueous hydrochloric acid and stirred, then warmed to room temperature and allowed to stand at room temperature. Then, the obtained reaction liquid was filtered, the filtrate was concentrated, hexane and water were added and stirred, and liquid separation was performed. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Then, it refine | purified by the silica gel column chromatography using the mixed solvent of hexane and a dichloromethane as a developing solvent, and compound 6-a (162g) was obtained.

<Synthesis Example 8> (Synthesis of Compound 6-b))

反応容器内をアルゴンガス気流下とし、化合物６−ａ（１６２ｇ）およびトリフルオロ酢酸（２４５ｍｌ）を加えた。得られた溶液にトリメチルシラン（１１５ｍｌ）を３０分間かけて滴下し、室温にて一晩撹拌した。その後、得られた反応溶液を１０℃に冷却し、ヘキサンおよび蒸留水を加え、１時間撹拌した後、分液を行った。その後、得られた油層に水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、濃縮して溶媒を除去した。得られた残渣をメタノールで洗浄することにより、目的とする化合物６−ｂ（１３８ｇ）を得た。

The reaction vessel was placed under an argon gas stream, and compound 6-a (162 g) and trifluoroacetic acid (245 ml) were added. Trimethylsilane (115 ml) was added dropwise to the resulting solution over 30 minutes and stirred overnight at room temperature. Thereafter, the obtained reaction solution was cooled to 10 ° C., hexane and distilled water were added, and the mixture was stirred for 1 hour, followed by liquid separation. Then, water was added to the obtained oil layer and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent, and concentrated to remove the solvent. The obtained residue was washed with methanol to obtain the intended compound 6-b (138 g).

<Synthesis Example 9> (Synthesis of Compound 6)

反応容器内をアルゴンガス気流下とし、化合物６−ｂ（１３８ｇ）、１−ブロモオクタン（７５．４ｍｌ）、メチルトリオクチルアンモニウムクロライド（商品名：Ａｌｉｑｕａｔ（登録商標）３３６、アルドリッチ社製）（１．２ｇ）および４０％水酸化カリウム（６０ｍｌ）を加え、８５℃にて一晩撹拌した。その後、得られた反応溶液を室温まで冷却し、ジクロロメタンおよび蒸留水を加え、１時間撹拌した後、分液を行った。その後、得られた油層に水を加え撹拌し、再度分液を行った。得られた油層に飽和食塩水を加え撹拌し、再度分液を行った。得られた油層に硫酸マグネシウムを加え撹拌し、ろ過し、得られたろ液を濃縮した。その後、ヘキサンおよびジクロロメタンの混合溶媒を展開溶媒としてシリカゲルカラムクロマトグラフィーにて精製し、濃縮して溶媒を除去した。その後、得られた残渣に対して、メタノールおよびジクロロメタンを用いた再沈殿を行うことにより、目的とする化合物６（１４５ｇ）を得た。

The reaction vessel was placed under an argon gas stream, and the compound 6-b (138 g), 1-bromooctane (75.4 ml), methyl trioctyl ammonium chloride (trade name: Aliquat (registered trademark) 336, manufactured by Aldrich) (1 0.2 g) and 40% potassium hydroxide (60 ml) were added and stirred at 85 ° C. overnight. Then, the obtained reaction solution was cooled to room temperature, dichloromethane and distilled water were added, and after stirring for 1 hour, liquid separation was performed. Then, water was added to the obtained oil layer and stirred, and liquid separation was performed again. Saturated saline was added to the obtained oil layer and the mixture was stirred and separated again. Magnesium sulfate was added to the obtained oil layer, stirred and filtered, and the obtained filtrate was concentrated. Thereafter, the mixture was purified by silica gel column chromatography using a mixed solvent of hexane and dichloromethane as a developing solvent, and concentrated to remove the solvent. Then, the target compound 6 (145g) was obtained by performing reprecipitation using methanol and a dichloromethane with respect to the obtained residue.

<Comparative Example 1> (Synthesis of Polymer Compound 1)
After making the gas in the reaction vessel an inert gas atmosphere, the following formula:

で表される化合物１（３．２８３６ｇ、４．２７ｍｍｏｌ）、下記式：

Compound 1 (3.2836 g, 4.27 mmol) represented by the following formula:

で表される化合物２（１．０８１７ｇ、１．６８ｍｍｏｌ）、下記式：

Compound 2 represented by (1.0817 g, 1.68 mmol), the following formula:

で表される化合物３（３．１０７４ｇ、４．８０ｍｍｏｌ）、下記式：

Compound 3 (3.1074 g, 4.80 mmol) represented by the following formula:

で表される化合物４（０．９８６９ｇ、１．２０ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（４．３ｍｇ）、トリオクチルメチルアンモニウムクロライド（商品名：Ａｌｉｑｕａｔ３３６（アルドリッチ製）、０．７９ｇ）およびトルエン（６０ｍｌ）を混合し、１０５℃に加熱した。得られた反応溶液に２Ｍ 炭酸ナトリウム水溶液（１６．３ｍｌ）を滴下し、３時間１０分還流させた。反応後、そこに、フェニルボロン酸（７３ｍｇ）、ジクロロビス（トリフェニルホスフィン）パラジウム（４．１ｍｇ）およびトルエン（６０ｍL）を加え、更に１５．５時間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。冷却後、得られた有機層を、水（７８ｍｌ）で２回、３重量％酢酸水溶液（７８ｍｌ）で２回、水（７８ｍｌ）で２回洗浄し、得られた溶液をメタノール（１５００ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（１９０ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムへ順番に通すことにより精製した。得られた溶液をメタノール（９３０ｍｌ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物１を４．５０ｇ得た。高分子化合物１のポリスチレン換算の数平均分子量は９．４×１０^４であり、ポリスチレン換算の重量平均分子量は２．７×１０^５であった。

4 (0.9869 g, 1.20 mmol), dichlorobis (triphenylphosphine) palladium (4.3 mg), trioctylmethylammonium chloride (trade name: Aliquat 336 (manufactured by Aldrich), 0.79 g) and toluene (60 ml) was mixed and heated to 105 ° C. To the obtained reaction solution, 2M aqueous sodium carbonate solution (16.3 ml) was added dropwise and refluxed for 3 hours and 10 minutes. After the reaction, phenylboronic acid (73 mg), dichlorobis (triphenylphosphine) palladium (4.1 mg) and toluene (60 mL) were added thereto, and the mixture was further refluxed for 15.5 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the obtained organic layer was washed twice with water (78 ml), twice with a 3 wt% aqueous acetic acid solution (78 ml) and twice with water (78 ml), and the resulting solution was dissolved in methanol (1500 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (190 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 (930 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 4.50 g of polymer compound 1. The number average molecular weight of polystyrene conversion of the high molecular compound 1 was 9.4 * 10 < ⁴ >, and the weight average molecular weight of polystyrene conversion was 2.7 * 10 < ⁵ >.

  The polymer compound 1 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位とが、３６：１４：４０：１０のモル比で構成されてなる共重合体である。
＜比較例２＞（高分子化合物６の合成）
反応容器内の気体を不活性ガス雰囲気とした後、下記式：

Is a copolymer composed of a molar ratio of 36: 14: 40: 10.
<Comparative example 2> (Synthesis of polymer compound 6)
After making the gas in the reaction vessel an inert gas atmosphere, the following formula:

で表される化合物５（１．３３９５ｇ、１．９８ｍｍｏｌ）、下記式：

Compound 5 (1.3395 g, 1.98 mmol) represented by the following formula:

で表される化合物６（１．０４９８ｇ、１．７６ｍｍｏｌ）、下記式：

で表される化合物１２（０．１７７３ｇ、０．２４ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（１．５ｍｇ）およびトルエン（４７ｍｌ）を混合し、１０５℃に加熱した。得られた反応溶液に２０重量％水酸化テトラエチルアンモニウム水溶液（７．５ｍｌ）を滴下し、３．５時間還流させた。反応後、そこに、フェニルボロン酸（２５ｍｇ）およびジクロロビス（トリフェニルホスフィン）パラジウム（１.５ｍｇ）を加え、更に１９時間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。冷却後、得られた有機層を、水（２６ｍｌ）で２回、３重量％酢酸水溶液（２６ｍｌ）で２回、水（２６ｍｌ）で２回洗浄し、得られた溶液をメタノール（３１０ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（９３ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムへ順番に通すことにより精製した。得られた溶液をメタノール（３２７ｍｌ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物６を１.３ｇ得た。高分子化合物６のポリスチレン換算の数平均分子量は９．１×１０^４であり、ポリスチレン換算の重量平均分子量は２．２×１０^５であった。

Compound 6 (1.0498 g, 1.76 mmol) represented by the following formula:

Embedded image Compound 12 (0.1773 g, 0.24 mmol), dichlorobis (triphenylphosphine) palladium (1.5 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7.5 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3.5 hours. After the reaction, phenylboronic acid (25 mg) and dichlorobis (triphenylphosphine) palladium (1.5 mg) were added thereto, and the mixture was further refluxed for 19 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the organic layer obtained was washed twice with water (26 ml), twice with 3% by weight acetic acid aqueous solution (26 ml) and twice with water (26 ml), and the resulting solution was dissolved in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (93 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 (327 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 1.3 g of polymer compound 6. The polymer compound 6 had a polystyrene-equivalent number average molecular weight of 9.1 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.2 × 10 ⁵ .

  The polymer compound 6 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位とが、５０：４４：６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: 44: 6.

<Example 1> (Synthesis of polymer compound 2)
After making the gas in the reaction vessel an inert gas atmosphere, Compound 1 (1.0899 g, 1.42 mmol), Compound 2 (0.3615 g, 0.56 mmol), Compound 3 (1.0358 g, 1.60 mmol), Compound M-4 (0.4136 g, 0.40 mmol), dichlorobis (triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed and heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 2 hours. After the reaction, phenylboronic acid (24 mg) and dichlorobis (triphenylphosphine) palladium (1.4 mg) were added thereto, and the mixture was further refluxed for 19 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the organic layer obtained was washed twice with water (26 ml), twice with 3% by weight acetic acid aqueous solution (26 ml) and twice with water (26 ml), and the resulting solution was dissolved in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (62 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 1.49 g of polymer compound 2. The polymer compound 2 had a polystyrene-equivalent number average molecular weight of 8.2 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.0 × 10 ⁵ .

  The polymer compound 2 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位とが、３６：１４：４０：１０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 36: 14: 40: 10.

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

で表される化合物５（１．３４４２ｇ、１．９８ｍｍｏｌ）、下記式：

Compound 5 (1.3442 g, 1.98 mmol) represented by the following formula:

で表される化合物６（１．０５２３ｇ、１．７６ｍｍｏｌ）、化合物Ｍ−６（０．２２７１ｇ、０．２４ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（１．４ｍｇ）およびトルエン（４７ｍｌ）を混合し、１０５℃に加熱した。得られた反応溶液に２０重量％水酸化テトラエチルアンモニウム水溶液（７ｍｌ）を滴下し、２時間還流させた。反応後、そこに、フェニルボロン酸（２４ｍｇ）およびジクロロビス（トリフェニルホスフィン）パラジウム（１．４ｍｇ）を加え、更に１９時間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。冷却後、得られた有機層を、水（２６ｍｌ）で２回、３重量％酢酸水溶液（２６ｍｌ）で２回、水（２６ｍｌ）で２回洗浄し、得られた溶液をメタノール（３１０ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（６２ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムへ順番に通すことにより精製した。得られた溶液をメタノール（３１０ｍｌ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物３を１．０８ｇ得た。高分子化合物３のポリスチレン換算の数平均分子量は３．８×１０^４であり、ポリスチレン換算の重量平均分子量は２．０×１０⁵であった。

Compound 6 (1.0523 g, 1.76 mmol), Compound M-6 (0.2271 g, 0.24 mmol), dichlorobis (triphenylphosphine) palladium (1.4 mg) and toluene (47 ml) were mixed. , Heated to 105 ° C. A 20 wt% tetraethylammonium hydroxide aqueous solution (7 ml) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 2 hours. After the reaction, phenylboronic acid (24 mg) and dichlorobis (triphenylphosphine) palladium (1.4 mg) were added thereto, and the mixture was further refluxed for 19 hours. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the organic layer obtained was washed twice with water (26 ml), twice with 3% by weight acetic acid aqueous solution (26 ml) and twice with water (26 ml), and the resulting solution was dissolved in methanol (310 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (62 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 1.08 g of polymer compound 3. The number average molecular weight of polystyrene conversion of the high molecular compound 3 was 3.8 * 10 < ⁴ >, and the weight average molecular weight of polystyrene conversion was 2.0 * 10 < ⁵ >.

  The polymer compound 3 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位とが、５０：４４：６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: 44: 6.

<Synthesis Example 10> (Synthesis of Polymer Compound 4)
After making the gas in the reaction vessel an inert gas atmosphere, the following formula:

で表される化合物７（２．６８８２ｇ、２．９６ｍｍｏｌ）、下記式：

Compound 7 (2.6882 g, 2.96 mmol) represented by the following formula:

で表される化合物８（０．４２４５ｇ、０．７５ｍｍｏｌ）、下記式：

Compound 8 (0.4245 g, 0.75 mmol) represented by the following formula:

で表される化合物９（１．６３９６ｇ、１．８０ｍｍｏｌ）、下記式：

Compound 9 (1.6396 g, 1.80 mmol) represented by the following formula:

で表される化合物１０（０．２３７７ｇ、０．４５ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（２．１ｍｇ）およびトルエン（６２ｍｌ）を混合し、１０５℃に加熱した。得られた反応溶液に、２０重量％水酸化テトラエチルアンモニウム水溶液（１０ｍｌ）を滴下し、４．５時間還流させた。反応後、そこに、フェニルボロン酸（３６．８ｍｇ）およびジクロロビス（トリフェニルホスフィン）パラジウム（２．１ｍｇ）を加え、更に１６．５間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。冷却後、得られた有機層を、水（４０ｍｌ）で２回、３重量％酢酸水溶液（４０ｍｌ）で２回、水（４０ｍｌ）で２回洗浄し、得られた溶液をメタノール（５００ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（１００ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムへ順番に通すことにより精製した。得られた溶液をメタノール（５００ｍｌ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物４を３．１２ｇ得た。高分子化合物４のポリスチレン換算の数平均分子量は７．８×１０^４であり、ポリスチレン換算の重量平均分子量は２．６×１０^５であった。

Embedded image Compound 10 (0.2377 g, 0.45 mmol), dichlorobis (triphenylphosphine) palladium (2.1 mg) and toluene (62 ml) were mixed and heated to 105 ° C. To the resulting reaction solution, a 20 wt% tetraethylammonium hydroxide aqueous solution (10 ml) was added dropwise and refluxed for 4.5 hours. After the reaction, phenylboronic acid (36.8 mg) and dichlorobis (triphenylphosphine) palladium (2.1 mg) were added thereto, and the mixture was further refluxed for 16.5. Next, an aqueous sodium diethyldithiacarbamate solution was added thereto, and the mixture was stirred at 80 ° C. for 2 hours. After cooling, the obtained organic layer was washed twice with water (40 ml), twice with a 3% by weight aqueous acetic acid solution (40 ml) and twice with water (40 ml), and the resulting solution was dissolved in methanol (500 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (100 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 (500 ml) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 3.12 g of polymer compound 4. The polymer compound 4 had a polystyrene-equivalent number average molecular weight of 7.8 × 10 ⁴ and a polystyrene-equivalent weight average molecular weight of 2.6 × 10 ⁵ .

  The polymer compound 4 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

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

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

<Synthesis Example 11> (Synthesis of Polymer Compound 5)
After making the gas in the reaction vessel an inert gas atmosphere, the following formula:

で表される化合物１１（３．７０２ｇ、６．９８ｍｍｏｌ）、化合物１（１３．３８０ｇ、１７．４５ｍｍｏｌ）、化合物３（１６．１２１ｇ、２４．９３ｍｍｏｌ）、ジクロロビス（トリフェニルホスフィン）パラジウム（１７．５ｍｇ）およびトルエン（４７８ｍＬ）を混合し、１００℃に加熱した。得られた反応溶液に２０質量％水酸化テトラエチルアンモニウム水溶液（８３．７ｇ）を滴下し、４．５時間還流させた。反応後、そこに、フェニルボロン酸（３００ｍｇ）およびジクロロビス（トリフェニルホスフィン）パラジウム（１７．５ｍｇ）を加え、さらに１４時間還流させた。次いで、そこに、ジエチルジチアカルバミン酸ナトリウム水溶液を加え、８０℃で２時間撹拌した。冷却後、得られた有機層を、水（３２４ｍＬ）で２回、３質量％酢酸水溶液（３２４ｍＬ）で２回、水（３２４ｍＬ）で２回洗浄し、得られた溶液をメタノール（３８５９ｍＬ）に滴下、ろ取することで沈殿物を得た。この沈殿物をトルエン（７７８ｍＬ）に溶解させ、アルミナカラム、シリカゲルカラムへ順番に通すことにより精製した。得られた溶液をメタノール（３８５９ｍＬ）に滴下し、撹拌した後、得られた沈殿物をろ取し、乾燥させることにより、高分子化合物５を１４．７５ｇ得た。高分子化合物５のポリスチレン換算の数平均分子量は６．１×１０^４であり、ポリスチレン換算の重量平均分子量は２．１×１０^５であった。

Compound 11 (3.702 g, 6.98 mmol), Compound 1 (13.380 g, 17.45 mmol), Compound 3 (16.121 g, 24.93 mmol), dichlorobis (triphenylphosphine) palladium (17. 5 mg) and toluene (478 mL) were mixed and heated to 100 ° C. A 20 mass% tetraethylammonium hydroxide aqueous solution (83.7 g) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 4.5 hours. After the reaction, phenylboronic acid (300 mg) and dichlorobis (triphenylphosphine) palladium (17.5 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. After cooling, the obtained organic layer was washed twice with water (324 mL), twice with a 3% by mass acetic acid aqueous solution (324 mL) and twice with water (324 mL), and the resulting solution was dissolved in methanol (3859 mL). A precipitate was obtained by dropping and filtering. This precipitate was dissolved in toluene (778 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 (3859 mL) and stirred, and then the resulting precipitate was collected by filtration and dried to obtain 14.75 g of polymer compound 5. The number average molecular weight in terms of polystyrene of the polymer compound 5 was 6.1 × 10 ⁴ , and the weight average molecular weight in terms of polystyrene was 2.1 × 10 ⁵ .

  The polymer compound 5 has the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位と、下記式：

And the following formula:

で表される構成単位とが、３６：１４：５０のモル比で構成されてなる共重合体である。

Is a copolymer composed of a molar ratio of 36:14:50.

<Example D1> Production of Light-Emitting Element 1 A Plexcore AQ-1200 (manufactured by Prectronics) is used to form a film with a thickness of 35 nm on a glass substrate on which an ITO film is attached with a thickness of 45 nm by sputtering. Then, a hole injection layer was formed by heating at 170 ° C. for 15 minutes on a hot plate in an air atmosphere.

  Next, the polymer compound 4 was dissolved in xylene (solvent) to prepare a 0.7 wt% xylene solution. Using this xylene solution, a film having a thickness of 20 nm was formed by spin coating on a glass substrate on which Plexcore AQ-1200 (manufactured by Plextronics) was formed, and was heated at 180 ° C. on a hot plate in a nitrogen atmosphere. The hole transport layer was formed by heating for 60 minutes.

Next, the polymer compound 2 and the polymer compound 5 are separately dissolved in xylene (solvent), and a 1.3 wt% polymer compound 2 xylene solution and a 1.3 wt% polymer compound 5 are dissolved. A xylene solution was prepared. Next, 1.3% by weight of a xylene solution of polymer compound 2 and 1.3% by weight of a xylene solution of polymer compound 5 were mixed so as to be 70% by weight: 30% by mass.
Using the obtained xylene solution, a film having a thickness of 60 nm was formed by spin coating on a glass substrate on which the polymer compound 4 was formed, and heated at 130 ° C. for 10 minutes on a hot plate in a nitrogen atmosphere. Thus, a light emitting layer was formed. Then, 5 nm of sodium fluoride and then 120 nm of aluminum were vapor-deposited as a cathode, and the light emitting element 1 was produced. In addition, after the degree of vacuum reached 1 × 10 ⁻⁴ Pa or less, metal deposition was started.

<Comparative Example D1> Production of Light Emitting Element C1 Instead of the xylene solution containing polymer compound 2 and polymer compound 5 in Example D1, a xylene solution containing polymer compound 1 and polymer compound 5 (1 .3 wt%) was used to produce a light emitting device C1 in the same manner as in Example D1.

  Table 1 shows the characteristics of the light-emitting element 1 and the light-emitting element C1 that were manufactured in Example D1 and Comparative Example D1, respectively. Here, the luminous efficiency is the luminous efficiency at 1000 cd / m 2.

  As disclosed in Table 1, a light emitting device manufactured using the polymer compound of the present invention is excellent in luminous efficiency.

<Example D2> Production of Light-Emitting Element 2 Instead of the xylene solution containing polymer compound 2 and polymer compound 5 in Example D1, a xylene solution (1) in which polymer compound 3 was dissolved in xylene (solvent) .3 wt%) was used to produce a light emitting device 2 in the same manner as in Example D1.

<Comparative Example D2> Production of Light-Emitting Element C2 Except that a xylene solution containing a polymer compound 6 (1.3 wt%) was used instead of the xylene solution containing the polymer compound 3 in Example D2. A light emitting device C2 was produced in the same manner as in Example D2.

  Table 2 shows the characteristics of the light-emitting element 2 and the light-emitting element C2 that were manufactured in Example D2 and Comparative Example D2, respectively. Here, the luminous efficiency is the luminous efficiency at 1000 cd / m 2.

  As disclosed in Table 2, the light emitting device produced using the polymer compound of the present invention is excellent in luminous efficiency.

Claims (19)

The high molecular compound containing the structural unit represented by following formula (1).

(In the formula (1),
Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group;
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
At least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. ) The polymer compound according to claim 1, wherein the structural unit represented by the formula (1) is a structural unit represented by the following formula (1-2).

(In the formula (1-2),
R ^a , R ^b and R ^c are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. When there are a plurality of R ^a , R ^b and R ^c , they may be the same or different.
Ar ^c and Ar ^d have the same meaning as described above.
h and j each independently represents an integer of 0 to 4, and i represents an integer of 0 to 2. Two h, i, and j may be the same or different. ) The polymer compound according to claim 2, wherein the structural unit represented by the formula (1-2) is a structural unit represented by the following formula (1-2-1).

(In the formula (1-2-1),
Ar ^c , Ar ^d , R ^a , R ^b , R ^c and i represent the same meaning as described above.
k and l each independently represents an integer of 0 to 3. ) Wherein Ar ^c is an unsubstituted or substituted phenylene group or an unsubstituted or substituted biphenyl-diyl group, a polymer compound according to any one of claims 1 to 3. The polymer compound according to claim 1, wherein Ar ^d is an unsubstituted or substituted phenyl group. Furthermore, at least 1 type of structural unit chosen from the group which consists of a structural unit represented by following formula (3) and a structural unit represented by following formula (4) is included. The high molecular compound as described in.

(In formula (3),
Ar ⁵ represents an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or a group represented by any of formulas 126 to 132 . )
(In formula (4),
Ar ⁶ each independently represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group,
Ar ⁷ and Ar ⁸ are each independently an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent complex. Represents a divalent group in which two or more groups selected from the group consisting of cyclic groups are linked;
Two Ar ⁶ may be the same or different.
E ₁ , E ₂ and E ₃ 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.
a and p each independently represent 0 or 1, and 0 ≦ a + p ≦ 1.
Ar ⁶ , Ar ⁷ , Ar ⁸ and Ar ⁹ are each a group other than the group bonded to the nitrogen atom to which the group is bonded, a single bond, —O—, —CR ¹ R ² — or — It may be passed by S-. R ¹ and R ² each independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group. )

(In the formulas 126 to 132, R represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent aromatic heterocyclic group. They may be the same or different.) The structural unit represented by the formula (3) is a structural unit represented by the following formula (3-1) or a structural unit represented by the following formula (3-2). Molecular compound.

(In Formula (3-1),
R ³ and R ⁴ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or unsubstituted Alternatively, it represents a substituted alkyl group. When a plurality of R ³ and R ⁴ are present, they may be the same or different.
b and c each independently represent an integer of 0 to 3.
R ⁵ and R ⁶ are each independently a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group Or an unsubstituted or substituted alkyl group is represented. )

(In the formula (3-2),
R ⁷ represents an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or an unsubstituted or substituted alkyl group. . When a plurality of R ⁷ are present, they may be the same or different.
d represents an integer of 0 to 4. ) The structural unit represented by the formula (4) is a structural unit represented by the following formula (4-1) or a structural unit represented by the following formula (4-2). High molecular compound.

(In the formula (4-1),
Q represents a single bond, —O—, —C (R ¹ ) (R ² ) —, —S—, and R ¹ and R ² represent the same meaning as described above.
Ar ¹⁴ represents a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted arylalkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group.
R ⁸ and R ⁹ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or unsubstituted Alternatively, it represents a substituted alkyl group. When a plurality of R ⁸ and R ⁹ are present, they may be the same or different.
e and f are each independently an integer of 0 to 3. )

(In the formula (4-2),
Ar ¹³ is selected from the group consisting of an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or an unsubstituted or substituted arylene group and an unsubstituted or substituted divalent heterocyclic group Represents a divalent group in which two or more groups are linked.
R ¹⁰ and R ¹¹ are each independently an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, an unsubstituted or substituted aryloxy group, an unsubstituted or substituted alkoxy group, or Represents a substituted or substituted alkyl group. When a plurality of R ¹⁰ and R ¹¹ are present, they may be the same or different.
g represents an integer of 0 to 4, m represents an integer of 0 to 5, and n represents 0 or 1. Two of g and m may be the same or different. ) The polymer compound according to any one of claims 6 to 8, wherein the structural unit represented by the formula (3) is a structural unit represented by the following formula (9).

(In Formula (9),
Ar ¹⁰ and Ar ¹¹ each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
Ar ¹² represents a hydrogen atom, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent heterocyclic group. ) Furthermore, the structural unit represented by the following formula (3-3) (different from the structural unit represented by the formula (3) and the structural unit represented by the formula (3-1)) and the following formula ( 4-3) (at least one selected from the group consisting of the structural unit represented by the formula (4) and the structural unit represented by the formula (4-2)). The high molecular compound as described in any one of Claims 1-9 containing the structural unit of these.

(In Formula (3-3),
R ²¹ represents a group represented by any of the following formulas (15A-1) to (15A-27) .
R ²² represents a hydrogen atom, a group represented by any of the following formulas (15A-1) to (15A-27) , an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or unsubstituted or substituted Represents a monovalent heterocyclic group. )
(In Formula (4-3),
R ²³ represents a group represented by any of the following formulas (15A-1) to (15A-27) .
R ²⁴ represents a group represented by any of the following formulas (15A-1) to (15A-27) , an unsubstituted or substituted alkyl group, an unsubstituted or substituted aryl group, or an unsubstituted or substituted monovalent group. Represents a heterocyclic group.
q represents 0 or 1; )

The content of the structural unit represented by the formula (1) is
For the total content of structural units contained in the polymer compound,
The polymer compound according to claim 1, which is 0.1 mol% or more and 50 mol% or less. The compound represented by following formula (5).

(Where
LG is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - with Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) And a group represented by a boronic acid ester residue or —O—SO ₂ —Z. Z represents an unsubstituted or substituted alkyl group or aryl group. Two LGs may be the same or different.
Ar ^a and Ar ^b each independently represent an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group;
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
At least one selected from the group consisting of Ar ^a and Ar ^b represents an unsubstituted or substituted phenanthrene diyl group.
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )   The manufacturing method of a high molecular compound including the process of superposing | polymerizing the compound of Claim 12, and using a transition metal compound as a catalyst. The manufacturing method of the compound represented by following formula (8) including the process with which the compound represented by following formula (6) and the compound represented by following formula (7) are made to react.

(In Formula (6),
Ar ^e represents an unsubstituted or substituted arylene group or an unsubstituted or substituted divalent heterocyclic group.
LG is a halogen atom (provided that a fluorine atom is _{excluded.), - B (OH)} 2, -BF 4 - with Q (Q represents lithium, sodium, potassium, a monovalent cation rubidium or cesium.) And a group represented by a boronic acid ester residue or —O—SO ₂ —Z. Z represents an unsubstituted or substituted alkyl group or aryl group. Two LGs may be the same or different. )
(In formula (7),
Ar ^c is an unsubstituted or substituted arylene group, an unsubstituted or substituted divalent heterocyclic group, or selected from the group consisting of divalent heterocyclic group unsubstituted or substituted arylene group and an unsubstituted or substituted Represents a divalent group in which two or more groups are connected,
Ar ^d represents a hydrogen atom, an unsubstituted or substituted aryl group, an unsubstituted or substituted monovalent heterocyclic group, or an unsubstituted or substituted alkyl group. Two Ar ^d may be the same or different. )
(In Formula (8),
Ar ^c , Ar ^d , Ar ^e and LG have the same meaning as described above. Two Ar ^d , Ar ^e and LG may be the same or different.
However, at least one of the two existing Ar ^e represents an unsubstituted or substituted phenanthrene diyl group. ) The polymer compound according to any one of claims 1 to 11,
A composition containing at least one material selected from the group consisting of a hole transport material, an electron transport material, and a light emitting material.   The liquid composition containing the high molecular compound as described in any one of Claims 1-11, and a solvent.   The organic thin film containing the high molecular compound as described in any one of Claims 1-11. A light-emitting element comprising an electrode composed of an anode and a cathode, and an organic layer provided between the electrodes,
The light emitting element in which this organic layer contains the high molecular compound as described in any one of Claims 1-11.   The light emitting device according to claim 18, wherein the organic layer is a light emitting layer or a charge transport layer.