JP6572682B2 - Compound and light emitting device using the same - Google Patents

Description

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

  A light-emitting element such as an organic electroluminescence element can be suitably used for display and illumination applications because of its high luminous efficiency. As a material used for a light emitting layer of a light emitting element, for example, a compound represented by the following formula has been proposed (Patent Document 1).

JP 2006-199698 A

  However, a light-emitting element manufactured using this compound has a problem that the driving voltage is not sufficiently low.

  Therefore, an object of the present invention is to provide a compound useful for manufacturing a light emitting device having a low driving voltage. Another object of the present invention is to provide a light emitting device containing this compound.

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

[1]
The compound represented by Formula (1).

［式中、
Ｒ¹及びＲ²は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
ｎ¹は、２以上１４以下の整数を表す。
Ｌ¹は、単結合又は−Ｎ（Ｒ^Z1）−で表される基を表す。Ｒ^Z1は、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＬ¹は、同一でも異なっていてもよい。
Ａｒ¹は、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＡｒ¹は、同一でも異なっていてもよい。但し、少なくとも１つのＡｒ¹は、式（１−Ａ）で表される基であり、且つ、少なくとも１つのＡｒ¹は、式（１−Ｂ）で表される基である。］

[Where:
R ¹ and R ² each independently represents a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryloxy group, monovalent heterocyclic group, substituted amino group or halogen atom. These groups may have a substituent.
n ¹ represents an integer of 2 or more and 14 or less.
L ¹ represents a single bond or a group represented by —N (R ^Z1 ) —. R ^Z1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of L ¹ may be the same or different.
Ar ¹ represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. A plurality of Ar ¹ may be the same or different. However, at least one Ar ¹ is a group represented by the formula (1-A), and at least one Ar ¹ is a group represented by the formula (1-B). ]

［式中、
Ｒ^1A、Ｒ^2A、Ｒ^3A、Ｒ^4A、Ｒ^5A、Ｒ^6A、Ｒ^7A及びＲ^8Aは、それぞれ独立に、結合手、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。但し、Ｒ^1A、Ｒ^2A、Ｒ^3A及びＲ^4Aのうち、１つは結合手であり、且つ、Ｒ^5A、Ｒ^6A、Ｒ^7A及びＲ^8Aのうち、１つは結合手である。
Ｒ^1AとＲ^2A、Ｒ^2AとＲ^3A、Ｒ^3AとＲ^4A、Ｒ^4AとＲ^5A、Ｒ^5AとＲ^6A、Ｒ^6AとＲ^7A、及び、Ｒ^7AとＲ^8Aは、それぞれ結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｒ^91Aは、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。
Ｒ^92Aは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[Where:
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A are each independently a bond, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl Represents a group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups optionally have a substituent. However, one of R ^1A , R ^2A , R ^3A and R ^4A is a bond, and one of R ^5A , R ^6A , R ^7A and R ^8A is a bond.
R ^1A and R ^2A , R ^2A and R ^3A , R ^3A and R ^4A , R ^4A and R ^5A , R ^5A and R ^6A , R ^6A and R ^7A , and R ^7A and R ^8A are bonded to each other, You may form the ring with the carbon atom to which each couple | bonds.
R ^91A represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom, and these groups optionally have a substituent.
R ^92A represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]

［式中、
Ｚ^Bは、−Ｃ（Ｒ^ZB）₂−で表される基、−Ｎ（Ｒ^ZB）−で表される基、硫黄原子又は酸素原子を表す。Ｒ^ZBは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。Ｒ^ZBが複数存在する場合、それらは同一でも異なっていてもよく、互いに結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。
Ｒ^1B、Ｒ^2B、Ｒ^3B、Ｒ^4B、Ｒ^5B、Ｒ^6B、Ｒ^7B及びＲ^8Bは、それぞれ独立に、結合手、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基、アリールオキシ基、１価の複素環基、置換アミノ基又はハロゲン原子を表し、これらの基は置換基を有していてもよい。但し、Ｒ^B1、Ｒ^B2、Ｒ^B3及びＲ^B4のうち、１つは結合手であり、且つ、Ｒ^B5、Ｒ^B6、Ｒ^B7及びＲ^B8のうち、１つは結合手である。
Ｒ^9Bは、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。
Ｒ^1BとＲ^2B、Ｒ^2BとＲ^3B、Ｒ^3BとＲ^4B、Ｒ^4BとＲ^ZB、Ｒ^ZBとＲ^B5、Ｒ^5BとＲ^6B、Ｒ^6BとＲ^7B、Ｒ^7BとＲ^8B、Ｒ^8BとＲ^9B、Ｒ^1BとＲ^9Bは、それぞれ結合して、それぞれが結合する炭素原子とともに環を形成していてもよい。］
［２］
Ｒ^2A及びＲ^3Aのうち、１つが結合手であり、且つ、Ｒ^6A及びＲ^7Aのうち、１つが結合手である、［１］記載の化合物。
［３］
Ｒ^91Aが、置換基を有していてもよいアルキル基又は置換基を有していてもよいシクロアルキル基である、［１］又は［２］記載の化合物。
［４］
Ｒ^92Aが、置換基を有していてもよいアリール基である、［１］〜［３］のいずれか一項記載の化合物。
［５］
Ｒ^2B及びＲ^3Bのうち、１つが結合手であり、且つ、Ｒ^6B及びＲ^7Bのうち、１つが結合手である、［１］〜［４］のいずれか一項記載の化合物。
［６］
Ｒ^９Bが、式（Ｄ−Ａ）で表される基、式（Ｄ−Ｂ）で表される基又は式（Ｄ−Ｃ）で表される基である、［１］〜［５］のいずれか一項記載の化合物。

[Where:
Z ^B represents a group represented by —C (R ^ZB ) ₂ —, a group represented by —N (R ^ZB ) —, a sulfur atom or an oxygen atom. R ^ZB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group or a halogen atom, and these groups are a substituent. You may have. When a plurality of R ^ZB are present, they may be the same or different, and may be bonded to each other to form a ring together with the carbon atom to which each is bonded.
R ^1B , R ^2B , R ^3B , R ^4B , R ^5B , R ^6B , R ^7B and R ^8B are each independently a bond, a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl Represents a group, an aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom, and these groups optionally have a substituent. However, one of R ^B1 , R ^B2 , R ^B3 and R ^B4 is a bond, and one of R ^B5 , R ^B6 , R ^B7 and R ^B8 is a bond.
R ^9B represents an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent.
R ^1B and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , R ^4B and R ^ZB , R ^ZB and R ^B5 , R ^5B and R ^6B , R ^6B and R ^7B , R ^7B and R ^8B , R ^8B And R ^9B , R ^1B and R ^9B may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]
[2]
The compound according to [1], wherein one of R ^2A and R ^3A is a bond, and one of R ^6A and R ^7A is a bond.
[3]
The compound according to [1] or [2], wherein R ^91A is an ^optionally substituted alkyl group or an optionally substituted cycloalkyl group.
[4]
The compound according to any one of [1] to [3], wherein R ^92A is an aryl group which may have a substituent.
[5]
The compound according to any one of [1] to [4], wherein one of R ^2B and R ^3B is a bond, and one of R ^6B and R ^7B is a bond.
[6]
R ^9B is a group represented by the formula (DA), a group represented by the formula (D-B), or a group represented by the formula (D-C), [1] to [5] A compound according to any one of the above.

［式中、
ｍ^DA1、ｍ^DA2及びｍ^DA3は、それぞれ独立に、０以上の整数を表す。
Ｇ^DAは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^DA1、Ａｒ^DA2及びＡｒ^DA3は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^DA1、Ａｒ^DA2及びＡｒ^DA3が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^DAは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^DAは、同一でも異なっていてもよい。］

[Where:
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

［式中、
ｍ^DA1、ｍ^DA2、ｍ^DA3、ｍ^DA4、ｍ^DA5、ｍ^DA6及びｍ^DA7は、それぞれ独立に、０以上の整数を表す。
Ｇ^DAは、窒素原子、芳香族炭化水素基又は複素環基を表し、これらの基は置換基を有していてもよい。複数あるＧ^DAは、同一でも異なっていてもよい。
Ａｒ^DA1、Ａｒ^DA2、Ａｒ^DA3、Ａｒ^DA4、Ａｒ^DA5、Ａｒ^DA6及びＡｒ^DA7は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^DA1、Ａｒ^DA2、Ａｒ^DA3、Ａｒ^DA4、Ａｒ^DA5、Ａｒ^DA6及びＡｒ^DA7が複数ある場合、それらはそれぞれ同一でも異なっていてもよい。
Ｔ^DAは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数あるＴ^DAは、同一でも異なっていてもよい。］

[Where:
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more.
^GDA represents a nitrogen atom, an aromatic hydrocarbon group, or a heterocyclic group, and these groups may have a substituent. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

［式中、
ｍ^DA1は、０以上の整数を表す。
Ａｒ^DA1は、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。Ａｒ^DA1が複数ある場合、それらは同一でも異なっていてもよい。
Ｔ^DAは、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］
［７］
Ｒ¹及びＲ²が、前記式（Ｄ−Ａ）で表される基、前記式（Ｄ−Ｂ）で表される基又は前記式（Ｄ−Ｃ）で表される基である、［１］〜［６］のいずれか一項記載の化合物。
［８］
式（Ｄ−Ａ）で表される基が、式（Ｄ−Ａ１）で表される基、式（Ｄ−Ａ２）で表される基又は（Ｄ−Ａ３）で表される基である、［６］又は［７］記載の化合物。

[Where:
m ^DA1 represents an integer of 0 or more.
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^{DA1 s} , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]
[7]
R ¹ and R ² are a group represented by the formula (DA), a group represented by the formula (DB), or a group represented by the formula (D-C). ] The compound as described in any one of [6].
[8]
The group represented by the formula (DA) is a group represented by the formula (D-A1), a group represented by the formula (D-A2), or a group represented by (D-A3). The compound according to [6] or [7].

［式中、
Ｒ^p1、Ｒ^p2及びＲ^p3は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はハロゲン原子を表す。Ｒ^p1及びＲ^p2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。
ｎｐ１は、０〜５の整数を表し、ｎｐ２は、０〜３の整数を表し、ｎｐ３は、０又は１を表す。複数存在するｎｐ１は、同一でも異なっていてもよい。］
［９］
式（Ｄ−Ｂ）で表される基が、式（Ｄ−Ｂ１）で表される基、式（Ｄ−Ｂ２）で表される基又は（Ｄ−Ｂ３）で表される基である、［６］又は［７］記載の化合物。

[Where:
R ^p1 , R ^p2 and R ^p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 may be the same or different. ]
[9]
The group represented by the formula (D-B) is a group represented by the formula (D-B1), a group represented by the formula (D-B2), or a group represented by (D-B3). The compound according to [6] or [7].

［式中、
Ｒ^p1、Ｒ^p2及びＲ^p3は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はハロゲン原子を表す。Ｒ^p1及びＲ^p2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。
ｎｐ１は、０〜５の整数を表し、ｎｐ２は、０〜３の整数を表し、ｎｐ３は、０又は１を表す。複数存在するｎｐ１は、同一でも異なっていてもよい。］
［１０］
式（Ｄ−Ｃ）で表される基が、式（Ｄ−Ｃ１）で表される基、式（Ｄ−Ｃ２）で表される基、式（Ｄ−Ｃ３）で表される基又は式（Ｄ−Ｃ４）で表される基である、［６］又は［７］記載の化合物。

[Where:
R ^p1 , R ^p2 and R ^p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 may be the same or different. ]
[10]
The group represented by the formula (D-C) is a group represented by the formula (D-C1), a group represented by the formula (D-C2), a group represented by the formula (D-C3) or a formula The compound of [6] or [7], which is a group represented by (D-C4).

［式中、
Ｒ^p4及びＲ^p5は、それぞれ独立に、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基又はハロゲン原子を表す。Ｒ^p4及びＲ^p5が複数ある場合、それらはそれぞれ同一であっても異なっていてもよい。
ｎｐ４は、０〜５の整数を表し、ｎｐ５は、０〜４の整数を表す。］
［１１］
Ｌ¹が、単結合である、［１］〜［１０］のいずれか一項記載の化合物。
［１２］
Ａｒ¹が、式（１−Ａ）で表される基又は式（１−Ｂ）で表される基である、［１］〜［１１］のいずれか一項記載の化合物。
［１３］
［１］〜［１２］のいずれか一項記載の化合物と、
正孔輸送材料、正孔注入材料、電子輸送材料、電子注入材料、発光材料、酸化防止剤及び溶媒からなる群より選ばれる少なくとも１種とを含有する組成物。
［１４］
［１］〜［１２］のいずれか一項記載の化合物を含有する発光素子。

[Where:
R ^p4 and R ^p5 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p4 and R ^p5 , they may be the same or different.
np4 represents an integer of 0 to 5, and np5 represents an integer of 0 to 4. ]
[11]
The compound according to any one of [1] to [10], wherein L ¹ is a single bond.
[12]
The compound according to any one of [1] to [11], wherein Ar ¹ is a group represented by formula (1-A) or a group represented by formula (1-B).
[13]
[1] to the compound according to any one of [12],
A composition containing at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent.
[14]
The light emitting element containing the compound as described in any one of [1]-[12].

  ADVANTAGE OF THE INVENTION According to this invention, a compound useful for manufacture of the light emitting element with a low drive voltage can be provided. Moreover, according to this invention, the light emitting element containing this compound can be provided.

  Hereinafter, preferred embodiments of the present invention will be described in detail.

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

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

  The hydrogen atom may be a deuterium atom or a light hydrogen atom.

  In the formula representing the metal complex, the solid line representing the bond with the central metal means a covalent bond or a coordinate bond.

The “polymer compound” means a polymer having a molecular weight distribution and having a polystyrene-equivalent number average molecular weight of 1 × 10 ³ to 1 × 10 ⁸ .

  The polymer compound may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, or other embodiments.

  The terminal group of the polymer compound is preferably a stable group because if the polymerization active group remains as it is, there is a possibility that the light emission characteristics or the luminance life may be lowered when the polymer compound is used for the production of a light emitting device. It is. The terminal group is preferably a group that is conjugated to the main chain, and examples thereof include a group that is bonded to an aryl group or a monovalent heterocyclic group via a carbon-carbon bond.

“Low molecular weight compound” means a compound having no molecular weight distribution and a molecular weight of 1 × 10 ⁴ or less.

  “Structural unit” means one or more units present in a polymer compound.

The “alkyl group” may be linear or branched. The carbon atom number of a linear alkyl group is 1-50 normally without including the carbon atom number of a substituent, Preferably it is 3-30, More preferably, it is 4-20. The number of carbon atoms of the branched alkyl group is usually 3 to 50, preferably 3 to 30, and more preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkyl group may have a substituent, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, 2-butyl group, isobutyl group, tert-butyl group, pentyl group, isoamyl group, 2-ethylbutyl, hexyl, heptyl, octyl, 2-ethylhexyl, 3-propylheptyl, decyl, 3,7-dimethyloctyl, 2-ethyloctyl, 2-hexyldecyl, dodecyl And a group in which a hydrogen atom in these groups is substituted with a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, etc., for example, a trifluoromethyl group, a pentafluoroethyl group, a peroxy group, and the like. Fluorobutyl group, perfluorohexyl group, perfluorooctyl group, 3-phenylpropyl group, 3- (4-methylphenyl) propyl group, 3- Examples include (3,5-di-hexylphenyl) propyl group and 6-ethyloxyhexyl group.
The number of carbon atoms of the “cycloalkyl group” is usually 3 to 50, preferably 3 to 30 and more preferably 4 to 20 without including the number of carbon atoms of the substituent.
The cycloalkyl group may have a substituent, and examples thereof include a cyclohexyl group, a cyclohexylmethyl group, and a cyclohexylethyl group.

“Aryl group” means an atomic group remaining after removing one hydrogen atom directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The carbon atom number of an aryl group is 6-60 normally without including the carbon atom number of a substituent, Preferably it is 6-20, More preferably, it is 6-10.
The aryl group may have a substituent, for example, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 1-pyrenyl group, 2 -Pyrenyl group, 4-pyrenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group, 2-phenylphenyl group, 3-phenylphenyl group, 4-phenylphenyl group, and hydrogen atoms in these groups Are groups substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, a fluorine atom, or the like.

The “alkoxy group” may be linear or branched. The number of carbon atoms of a linear alkoxy group is 1-40 normally without including the carbon number of a substituent, Preferably it is 4-10. The number of carbon atoms of the branched alkoxy group is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The alkoxy group may have a substituent, for example, methoxy group, ethoxy group, propyloxy group, isopropyloxy group, butyloxy group, isobutyloxy group, tert-butyloxy group, pentyloxy group, hexyloxy group, Heptyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyloxy group, lauryloxy group, and the hydrogen atom in these groups is a cycloalkyl group, an alkoxy group, And a group substituted with a cycloalkoxy group, an aryl group, a fluorine atom, or the like.
The number of carbon atoms of the “cycloalkoxy group” is usually 3 to 40, preferably 4 to 10, not including the number of carbon atoms of the substituent.
The cycloalkoxy group may have a substituent, and examples thereof include a cyclohexyloxy group.

The number of carbon atoms of the “aryloxy group” is usually 6 to 60, preferably 6 to 48, not including the number of carbon atoms of the substituent.
The aryloxy group may have a substituent, for example, a phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 1-anthracenyloxy group, 9-anthracenyloxy group, 1- Examples include a pyrenyloxy group and a group in which a hydrogen atom in these groups is substituted with an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, a fluorine atom, or the like.

The “p-valent heterocyclic group” (p represents an integer of 1 or more) is p of hydrogen atoms directly bonded to a carbon atom or a hetero atom constituting a ring from a heterocyclic compound. This means the remaining atomic group excluding the hydrogen atom. Among the p-valent heterocyclic groups, it is the remaining atomic group obtained by removing p hydrogen atoms from the hydrogen atoms directly bonded to the carbon atoms or heteroatoms constituting the ring from the aromatic heterocyclic compound. A “p-valent aromatic heterocyclic group” is preferable.
`` Aromatic heterocyclic compounds '' are oxadiazole, thiadiazole, thiazole, oxazole, thiophene, pyrrole, phosphole, furan, pyridine, pyrazine, pyrimidine, triazine, pyridazine, quinoline, isoquinoline, carbazole, dibenzophosphole, etc. A compound in which the ring itself exhibits aromaticity, and a heterocyclic ring such as phenoxazine, phenothiazine, dibenzoborol, dibenzosilol, benzopyran itself does not exhibit aromaticity, but the aromatic ring is condensed to the heterocyclic ring Means a compound.

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

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

The “amino group” may have a substituent, and a substituted amino group is preferable. As a substituent which an amino group has, an alkyl group, a cycloalkyl group, an aryl group, or a monovalent heterocyclic group is preferable.
Examples of the substituted amino group include a dialkylamino group, a dicycloalkylamino group, and a diarylamino group.
Examples of the amino group include dimethylamino group, diethylamino group, diphenylamino group, bis (4-methylphenyl) amino group, bis (4-tert-butylphenyl) amino group, bis (3,5-di-tert- Butylphenyl) amino group.

The “alkenyl group” may be linear or branched. The number of carbon atoms of a linear alkenyl group is 2-30 normally without including the carbon atom number of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkenyl group is usually 3 to 30, and preferably 4 to 20, not including the number of carbon atoms of the substituent.
The number of carbon atoms of the “cycloalkenyl group” is usually 3 to 30, preferably 4 to 20, not including the number of carbon atoms of the substituent.
The alkenyl group and the cycloalkenyl group may have a substituent, for example, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 3-pentenyl group, a 4-pentenyl group, Examples include a pentenyl group, a 1-hexenyl group, a 5-hexenyl group, a 7-octenyl group, and groups in which these groups have a substituent.

The “alkynyl group” may be linear or branched. The carbon atom number of an alkynyl group is 2-20 normally without including the carbon atom of a substituent, Preferably it is 3-20. The number of carbon atoms of the branched alkynyl group is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The number of carbon atoms of the “cycloalkynyl group” is usually 4 to 30, preferably 4 to 20, not including the carbon atom of the substituent.
The alkynyl group and the cycloalkynyl group may have a substituent, for example, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-pentynyl group, 4- Examples include a pentynyl group, 1-hexynyl group, 5-hexynyl group, and groups in which these groups have a substituent.

The “arylene group” means an atomic group remaining after removing two hydrogen atoms directly bonded to a carbon atom constituting a ring from an aromatic hydrocarbon. The number of carbon atoms of the arylene group is usually 6 to 60, preferably 6 to 30 and more preferably 6 to 18 without including the number of carbon atoms of the substituent.
The arylene group may have a substituent, for example, phenylene group, naphthalenediyl group, anthracenediyl group, phenanthrene diyl group, dihydrophenanthenediyl group, naphthacene diyl group, fluorenediyl group, pyrenediyl group, perylene diyl group, Examples include chrysenediyl groups and groups in which these groups have substituents, and groups represented by formula (A-1) to formula (A-20) are preferable. The arylene group includes a group in which a plurality of these groups are bonded.

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

[Wherein, R and R ^a each independently represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group. A plurality of R and R ^a may be the same or different, and R ^a may be bonded to each other to form a ring together with the atoms to which they are bonded. ]

The carbon atom number of a bivalent heterocyclic group is 2-60 normally without including the carbon atom number of a substituent, Preferably, it is 3-20, More preferably, it is 4-15.
The divalent heterocyclic group may have a substituent, for example, pyridine, diazabenzene, triazine, azanaphthalene, diazanaphthalene, carbazole, dibenzofuran, dibenzothiophene, dibenzosilol, phenoxazine, phenothiazine, acridine, Divalent acridine, furan, thiophene, azole, diazole, and triazole include divalent groups obtained by removing two hydrogen atoms from hydrogen atoms directly bonded to carbon atoms or heteroatoms constituting the ring, and preferably Is a group represented by formula (AA-1) to formula (AA-34). The divalent heterocyclic group includes a group in which a plurality of these groups are bonded.

［式中、Ｒ及びＲ^aは、前記と同じ意味を表す。］

[Wherein, R and R ^a represent the same meaning as described above. ]

  The `` crosslinking group '' is a group capable of generating a new bond by being subjected to heating, ultraviolet irradiation, near ultraviolet irradiation, visible light irradiation, infrared irradiation, radical reaction, etc. B-1) is a group represented by any one of (B-17). These groups may have a substituent.

  “Substituent” means a halogen atom, cyano group, alkyl group, cycloalkyl group, aryl group, monovalent heterocyclic group, alkoxy group, cycloalkoxy group, aryloxy group, amino group, substituted amino group, alkenyl group. Represents a cycloalkenyl group, an alkynyl group or a cycloalkynyl group. The substituent may be a crosslinking group.

<Compound represented by Formula (1)>
Next, the compound represented by Formula (1) which is a compound of this invention is demonstrated.

As the aryl group represented by R ¹ and R ² , a phenyl group, a naphthyl group, an anthracenyl group, a fentrenyl group, a dihydrofentrenyl group, a fluorenyl group, or a pyrenyl group is preferable, and a phenyl group, a naphthyl group, or a fluorenyl group is more preferable. Preferably, a phenyl group is more preferable, and these groups may have a substituent.

Examples of the monovalent heterocyclic group represented by R ¹ and R ² include pyridyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, dibenzofuranyl group, dibenzothienyl group, carbazolyl group, azacarbazolyl group, diaza A carbazolyl group, a phenoxazinyl group or a phenothiazinyl group is preferable, a pyridyl group, a pyrimidinyl group, a triazinyl group, a carbazolyl group, an azacarbazolyl group or a diazacarbazolyl group is more preferable, and a pyridyl group, a pyrimidinyl group or a triazinyl group is more preferable. These groups may have a substituent.

In the substituted amino group represented by R ¹ and R ² , the substituent that the amino group has is preferably an aryl group or a monovalent heterocyclic group, and these groups may further have a substituent. The preferred range of the aryl group and monovalent heterocyclic group in the substituent of the amino group is the same as the preferred range of the aryl group and monovalent heterocyclic group represented by R ¹ and R ² .

As the substituent that R ¹ and R ² may have, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group, an alkoxy group, a cycloalkoxy group, an aryloxy group, or a substituted amino group is preferable. An alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group is more preferred, an alkyl group, a cycloalkyl group or an aryl group is more preferred, and these groups further have a substituent. Also good.

R ¹ and R ² are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, a monovalent heterocyclic group or a substituted amino group because the driving voltage of the light-emitting device containing the compound of the present invention is lowered. And more preferably an aryl group, a monovalent heterocyclic group or a substituted amino group, and still more preferably represented by the formula (DA), the formula (D-B) or the formula (D-C). These groups may have a substituent.

m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are usually an integer of 10 or less, preferably an integer of 5 or less, more preferably 0 or 1. m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 are preferably the same integer.

G ^DA is preferably a group represented by the formula (GDA-11) ~ formula (GDA-15), more preferably a group represented by the formula (GDA-11) ~ formula (GDA-14) More preferably, it is a group represented by the formula (GDA-11).

［式中、
＊は、式(D-A)におけるＡｒ^DA1、式(D-B)におけるＡｒ^DA1、式(D-B)におけるＡｒ^DA2、又は、式(D-B)におけるＡｒ^DA3との結合を表す。
＊＊は、式(D-A)におけるＡｒ^DA2、式(D-B)におけるＡｒ^DA2、式(D-B)におけるＡｒ^DA4、又は、式(D-B)におけるＡｒ^DA6との結合を表す。
＊＊＊は、式(D-A)におけるＡｒ^DA3、式(D-B)におけるＡｒ^DA3、式(D-B)におけるＡｒ^DA5、又は、式(D-B)におけるＡｒ^DA7との結合を表す。
Ｒ^DAは、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は更に置換基を有していてもよい。Ｒ^DAが複数ある場合、それらは同一でも異なっていてもよい。］

[Where:
* Is, Ar ^DA1 in the formula (DA), Ar ^DA1 in the formula (DB), Ar in formula (DB) ^DA2, or represents a bond between Ar ^DA3 in the formula (DB).
** is, Ar ^DA2 in the formula (DA), Ar ^DA2 in the formula (DB), Ar in formula (DB) ^DA4, or represents a bond between Ar ^DA6 in the formula (DB).
*** is, Ar ^DA3 in the formula (DA), Ar ^DA3 in the formula (DB), Ar in formula (DB) ^DA5, or represents a bond between Ar ^DA7 in formula (DB).
R ^DA represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may further have a substituent. When there are a plurality of ^RDA , they may be the same or different. ]

R ^DA is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group or a cycloalkoxy group, more preferably a hydrogen atom, an alkyl group or a cycloalkyl group, and these groups have a substituent. May be.

Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 are preferably a phenylene group, a ^fluorenediyl group or a carbazolediyl group, more preferably a formula (A-1) to a formula (A-3), Formula (A-8), Formula (A-9), Formula (AA-10), Formula (AA-11), Formula (AA-33) or Formula (AA-34) More preferably a group represented by formula (ArDA-1) to formula (ArDA-5), particularly preferably a group represented by formula (ArDA-1) to formula (ArDA-3). And particularly preferably a group represented by the formula (ArDA-1), and these groups optionally have a substituent.

［式中、
Ｒ^DAは前記と同じ意味を表す。
Ｒ^DBは、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^DBが複数ある場合、それらは同一でも異なっていてもよい。］

[Where:
R ^DA represents the same meaning as described above.
R ^DB represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are a plurality of ^RDBs , they may be the same or different. ]

R ^DB is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group or a monovalent heterocyclic group, still more preferably an aryl group, The group may have a substituent.

T ^DA is preferably a group represented by the formula (TDA-1) ~ formula (TDA-3), more preferably a group represented by the formula (TDA-1).

［式中、Ｒ^DA及びＲ^DBは前記と同じ意味を表す。］

[Wherein R ^DA and R ^DB represent the same meaning as described above. ]

  The group represented by formula (DA) is preferably a group represented by formula (D-A1) to formula (D-A3), more preferably a group represented by formula (D-A1). .

  The group represented by the formula (DB) is preferably a group represented by the formula (D-B1) to the formula (D-B3), more preferably a group represented by the formula (D-B1). .

  The group represented by the formula (DC) is preferably a group represented by the formula (D-C1) to the formula (D-C4), more preferably the formula (D-C1) to the formula (D-C3). More preferably a group represented by the formula (D-C1) or the formula (D-C2), particularly preferably a group represented by the formula (D-C1).

np1 is preferably 0 or 1, more preferably 1.
np2 is preferably 0 or 1, more preferably 0.
np3 is preferably 0.
np4 is preferably 0-2.
np5 is preferably 0 to 2, and more preferably 0.

R ^p1 , R ^p2 , R ^p3 , R ^p4 and R ^p5 are preferably an alkyl group or a cycloalkyl group.

  Examples of the group represented by the formula (D-A) include groups represented by the formula (DA-1) to the formula (DA-12).

［式中、Ｒ^Dは、メチル基、エチル基、イソプロピル基、ｔｅｒｔ−ブチル基、ヘキシル基、２−エチルヘキシル基、ｔｅｒｔ−オクチル基、シクロヘキシル基、メトキシ基、２−エチルヘキシルオキシ基又はシクロへキシルオキシ基を表す。Ｒ^Dが複数存在する場合、それらは同一でも異なっていてもよい。］

[Wherein, R ^D represents a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, a tert-octyl group, a cyclohexyl group, a methoxy group, a 2-ethylhexyloxy group, or a cyclohexyloxy group. Represents a group. When two or more ^RD exists, they may be the same or different. ]

  Examples of the group represented by the formula (D-B) include groups represented by the formula (D-B-1) to the formula (D-B-4).

［式中、Ｒ^Dは前記と同じ意味を表す。］

[Wherein, R ^D represents the same meaning as described above. ]

  Examples of the group represented by the formula (D-C) include groups represented by the formula (DC-1) to the formula (DC-13).

［式中、Ｒ^Dは前記と同じ意味を表す。］

[Wherein, R ^D represents the same meaning as described above. ]

R ^D is preferably a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a hexyl group, a 2-ethylhexyl group, or a tert-octyl group, and more preferably a tert-butyl group.

R ¹ and R ² are preferably an aryl group which may have a substituent since the driving voltage of the light-emitting device containing the compound of the present invention is lower, and more preferably a formula (D- A1), a group represented by Formula (D-B1) or Formula (D-C1) to Formula (D-C4), and more preferably Formula (D-A1), Formula (D-B1) or Formula A group represented by formula (D-C1) to formula (D-C3), particularly preferably a group represented by formula (D-A1), formula (D-B1) or formula (D-C1). Particularly preferred is a group represented by the formula (D-B1) or the formula (D-C1).

n < ¹ > becomes like this. Preferably it is an integer of 2-12, More preferably, it is an integer of 3-10, More preferably, it is an integer of 3-7.

L ¹ is preferably a single bond.

The preferred range of the aryl group and monovalent heterocyclic group represented by R ^Z1 is the same as the preferred range of the aryl group and monovalent heterocyclic group represented by R ¹ and R ² .

The preferred range of the substituent that R ^Z1 may have is the same as the preferred range of the substituent that R ¹ and R ² may have.

A preferred range of the arylene group and divalent heterocyclic group represented by Ar ¹ are the same as the preferable range of the heterocyclic group of the arylene group and divalent represented by the below-mentioned Ar ^Y1. However, at least one Ar ¹ is a group represented by the formula (1-A), and at least one Ar ¹ is a group represented by the formula (1-B).

The preferred range of the substituent that Ar ¹ may have is the same as the preferred range of the substituent that Ar ^Y1 described later may have.

When three or more Ar ¹ are present and two or more Ar ¹ are groups represented by the formula (1-A), they may be the same or different.

When three or more Ar ¹ are present and two or more Ar ¹ are groups represented by the formula (1-B), they may be the same or different.

If Ar ¹ is present three or more, than the number Ar ¹ is a group represented by the formula (1-B), Ar ¹ is found the following number is a group represented by the formula (1-A) A large amount is preferable.

When three or more Ar ¹ are present, it is preferable that two or more Ar ¹ is a group represented by the formula (1-A).

When three or more Ar ¹ are present, it is preferable that two or less Ar ¹ is a group represented by the formula (1-B), and one Ar ¹ is represented by the formula (1-B). More preferably, it is a group.

Ar ¹ is preferably a group represented by the formula (1-A) or a group represented by the formula (1-B) because the driving voltage of the light-emitting element containing the compound of the present invention is lowered.

[Group Represented by Formula (1-A)]
Next, the group represented by Formula (1-A) will be described.

Of R ^2A and R ^3A , one is preferably a bond, and R ^2A is more preferably a bond.

Of R ^6A and R ^7A , one is preferably a bond, and R ^7A is more preferably a bond.

One of R ^2A and R ^3A is preferably a bond, and one of R ^6A and R ^7A is preferably a bond, R ^2A is a bond, and R ^7A is a bond. It is more preferable that

When R ^{1A to} R ^8A are other than a bond, R ^{1A to} R ^8A are preferably a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an aryl group, or a monovalent heterocyclic group, more preferably A hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom, and these groups optionally have a substituent.

The preferred range of the aryl group represented by R ^{1A to} R ^8A is the same as the preferred range of the aryl group represented by R ¹ and R ² .

The preferred range of the monovalent heterocyclic group represented by R ^{1A to} R ^8A is the same as the preferred range of the monovalent heterocyclic group represented by R ¹ and R ² .

The preferred range of the substituted amino group represented by R ^{1A to} R ^8A is the same as the preferred range of the substituted amino group represented by R ¹ and R ² .

The preferred range of the substituent that R ^{1A to} R ^8A may have is the same as the preferred range of the substituent that R ¹ and R ² may have.

R ^1A and R ^2A , R ^2A and R ^3A , R ^3A and R ^4A , R ^4A and R ^5A , R ^5A and R ^6A , R ^6A and R ^7A , and R ^7A and R ^8A are bonded to each other, Preferably, each does not form a ring with the carbon atom to which it is attached.

R ^91A is preferably an alkyl group which may have a substituent or an cycloalkyl group which may have a substituent because the driving voltage of the light-emitting element containing the compound of the present invention is lowered. More preferably an alkyl group which may have a substituent, and still more preferably an alkyl group which has no substituent.

The preferred range of the substituent that R ^91A may have is the same as the preferred range of the substituent that R ¹ and R ² may have.

The preferred range of the aryl group represented by R ^92A is the same as the preferred range of the aryl group represented by R ¹ and R ² .

The preferred range of the monovalent heterocyclic group represented by R ^92A is the same as the preferred range of the monovalent heterocyclic group represented by R ¹ and R ² .

The preferred range of the substituent that R ^92A may have is the same as the preferred range of the substituent that R ¹ and R ² may have.

The aryl group and monovalent heterocyclic group represented by R ^92A are preferably groups represented by the formula (DA) to the formula (DC). However, when R ^92A is a group represented by the formula (DA) or the formula ( ^DB ) and m ^DA1 is 0, in the formula ( ^DA ) and the formula (D-B), G ^DA bonded to Ar ^DA1 , Ar ^DA2 and Ar ^DA3 is an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.

R ^92A is preferably an aryl group which may have a substituent since the driving voltage of the light-emitting device containing the compound of the present invention is lower, more preferably a formula (D-A1), A group represented by formula (D-B1) or formula (D-C1) to formula (D-C4), more preferably formula (D-A1), formula (D-B1) or formula (D- C1) to a group represented by formula (D-C3), particularly preferably a group represented by formula (D-A1), formula (D-B1) or formula (D-C1), and particularly preferred Is a group represented by the formula (D-C1).

  The group represented by the formula (1-A) preferably has the formula (1-A-A1) or the formula (1-A-A2) because the driving voltage of the light-emitting element containing the compound of the present invention is lowered. And a group represented by the formula (1-A-A1) is more preferable.

  Examples of the group represented by the formula (1-A) include groups represented by the formula (1-A-1) to the formula (1-A-19). Preferably, the group represented by the formula (1-A) -1) to groups represented by formula (1-A-16), more preferably groups represented by formula (1-A-1) to formula (1-A-11), and Preferably, it is group represented by a formula (1-A-1)-a formula (1-A-8).

[Group Represented by Formula (1-B)]
Next, the group represented by Formula (1-B) will be described.

Z ^B is preferably a sulfur atom or an oxygen atom, more preferably an oxygen atom.

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

Preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by R ^ZB are the preferred ranges of the aryl group, monovalent heterocyclic group and substituted amino group represented by R ¹ and R ^2. The same.

The preferred range of the substituent that R ^ZB may have is the same as the preferred range of the substituent that R ¹ and R ² may have.

Of R ^2B and R ^3B , one is preferably a bond, and R ^3B is more preferably a bond.

Of R ^6B and R ^7B , one is preferably a bond, and R ^6B is more preferably a bond.

One of R ^2B and R ^3B is preferably a bond, and one of R ^6B and R ^7B is preferably a bond, R ^3B is a bond, and R ^6B is a bond. It is more preferable that

Otherwise hand R ^1B to R ^8B are combined, the preferred range of R ^1B to R ^8B are the same as the preferred ranges of R ^1A to R ^8A when R ^1A to R ^8A is other than binding hand.

R ^1B and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , R ^4B and R ^ZB , R ^ZB and R ^B5 , R ^5B and R ^6B , R ^6B and R ^7B , R ^7B and R ^8B , R ^8B And R ^9B , R ^1B and R ^9B are preferably bonded to each other and do not form a ring with the carbon atom to which they are bonded.

The preferred range of the aryl group and monovalent heterocyclic group represented by R ^9B is the same as the preferred range of the aryl group and monovalent heterocyclic group represented by R ¹ and R ² .

The preferred range of the substituent that R ^9B may have is the same as the preferred range of the substituent that R ¹ and R ² may have.

R ^9B is preferably an aryl group which may have a substituent or a monovalent heterocyclic group which may have a substituent. The aryl group and monovalent heterocyclic group represented by R ^9B are preferably groups represented by formulas (DA) to (DC). However, when R ^9B is a group represented by the formula (DA) or the formula (D-B) and m ^DA1 is 0, in the formula ( ^DA ) and the formula (D-B), G ^DA bonded to Ar ^DA1 , Ar ^DA2 and Ar ^DA3 is an aromatic hydrocarbon group or a heterocyclic group, and these groups may have a substituent.

R ^9B is preferably an aryl group which may have a substituent since the driving voltage of the light-emitting device containing the compound of the present invention is lower, more preferably, the formula (D-A1), A group represented by formula (D-B1) or formula (D-C1) to formula (D-C4), more preferably formula (D-A1), formula (D-B1) or formula (D- C1) to a group represented by formula (D-C3), particularly preferably a group represented by formula (D-A1), formula (D-B1) or formula (D-C1), and particularly preferred Is a group represented by the formula (D-B1).

  The group represented by the formula (1-B) is preferably a group represented by the formula (1-B-B1) or the formula (1-B-B2) because the compound of the present invention can be easily synthesized. And more preferably a group represented by the formula (1-B-B1).

  Examples of the group represented by the formula (1-B) include groups represented by the formula (1-B-1) to the formula (1-B-27). Preferably, the group represented by the formula (1-B) -1) to groups represented by formula (1-B-21), more preferably groups represented by formula (1-B-1) to formula (1-B-14), and Preferably, it is group represented by Formula (1-B-1)-Formula (1-B-8).

  Examples of the compound represented by the formula (1) include compounds represented by the formula (1-1) to the formula (1-19), and preferably the formula (1-4) to the formula (1- It is a compound represented by 17), More preferably, it is a compound represented by Formula (1-6)-Formula (1-13).

<Method for Producing Compound Represented by Formula (1)>
The compound of the present invention can be synthesized using a known coupling reaction using a transition metal catalyst such as Suzuki reaction, Buchwald reaction, Stille reaction, Negishi reaction and Kumada reaction.

[Production Method of Compound (1 ′)]
First, in the compound represented by the formula (1), a method for producing a compound in which all of a plurality of L ¹ are single bonds (hereinafter referred to as “compound (1 ′)”) will be described.

  For example, the compound (1 ′) includes a compound represented by the formula (1′-1), a compound represented by the formula (1′-2), and a compound represented by the formula (1′-3). The compound represented by the formula (1′-4) can be synthesized by reacting it using a known coupling reaction or the like.

［式中、
Ａｒ¹、Ｒ¹及びＲ²は前記と同じ意味を表す。
Ｚ^C1〜Ｚ^C6は、それぞれ独立に、置換基Ａ群及び置換基Ｂ群からなる群から選ばれる基を表す。］

[Where:
Ar ¹ , R ¹ and R ² represent the same meaning as described above.
Z ^{C1 to} Z ^C6 each independently represent a group selected from the group consisting of the substituent group A and the substituent group B. ]

<Substituent group A>
Chlorine atom, bromine atom, iodine atom, —O—S (═O) ₂ R ^C1 (wherein R ^C1 represents an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. A group represented by:

<Substituent group B>
-B in (OR ^C2) ₂ (wherein, R ^C2 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. There exist a plurality of R ^C2 is Groups which may be the same or different and may be linked to each other to form a ring structure together with the oxygen atoms to which they are bonded.
A group represented by —BF ₃ Q ′ (wherein Q ′ represents Li, Na, K, Rb or Cs);
A group represented by —MgY ′ (wherein Y ′ represents a chlorine atom, a bromine atom or an iodine atom);
A group represented by —ZnY ″ (wherein Y ″ represents a chlorine atom, a bromine atom or an iodine atom); and
-Sn (R ^C3) ₃ (wherein, R ^C3 represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aryl group, these groups may have a substituent. More existing R ^C3 is The groups may be the same or different and may be linked to each other to form a ring structure together with the tin atoms to which they are bonded.

Examples of the group represented by —B (OR ^C2 ) ₂ include groups represented by the formula (W-1) -formula (W-10).

[Synthesis Methods 1 and 2]
For example, the compound represented by the formula (1′-1) and the compound represented by the formula (1′-2) are subjected to a coupling reaction once or twice or more to thereby form the formula (1′-5). Or a compound represented by the formula (1′-6) can be synthesized.

［式中、Ａｒ¹、Ｚ^C1、Ｚ^C2及びＺ^C3は前記と同じ意味を表す。］

[Wherein, Ar ¹ , Z ^C1 , Z ^C2 and Z ^C3 represent the same meaning as described above. ]

Next, for example, the compound represented by the formula (1′-5), the compound represented by the formula (1′-3), and the compound represented by the formula (1′-4) are once processed. Alternatively, compound (1 ′) can be synthesized by a coupling reaction two or more times (hereinafter referred to as “synthesis method 1”).
Alternatively, for example, the compound represented by the formula (1′-6), the compound represented by the formula (1′-3), and the compound represented by the formula (1′-4) are once or Compound (1 ′) can be synthesized by a coupling reaction two or more times (hereinafter referred to as “synthesis method 2”).

In the synthesis method 1, for example, when Z ^C1 and Z ^C2 are groups selected from the substituent group A, Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 select groups selected from the substituent group B. For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group B, Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 select groups selected from the substituent group A.

In Synthesis Method 2, for example, when Z ^C1 , Z ^C2 and Z ^C6 are groups selected from the substituent group A, Z ^C3 , Z ^C4 and Z ^C5 select a group selected from the substituent group B. For example, when Z ^C1 , Z ^C2 and Z ^C6 are groups selected from the substituent group B, Z ^C3 , Z ^C4 and Z ^C5 select a group selected from the substituent group A.

[Synthesis Methods 3 to 6]
For example, a compound represented by formula (1′-1) or a compound represented by formula (1′-2) and a compound represented by formula (1′-3) or formula (1′-4) A compound represented by the compounds represented by formula (1′-7) to formula (1′-10) can be synthesized by a coupling reaction with the represented compound.

［式中、Ａｒ¹、Ｚ^C2、Ｚ^C4、Ｒ¹及びＲ²は前記と同じ意味を表す。］

[Wherein, Ar ¹ , Z ^C2 , Z ^C4 , R ¹ and R ² represent the same meaning as described above. ]

Next, for example, a compound (1 ′) is synthesized by a coupling reaction between the compound represented by the formula (1′-7) and the compound represented by the formula (1′-10). (Hereinafter referred to as “synthesis method 3”).
Alternatively, for example, the compound represented by the formula (1′-7), the compound represented by the formula (1′-8), and the compound represented by the formula (1′-2) are once or Compound (1 ′) can be synthesized by a coupling reaction two or more times (hereinafter referred to as “synthesis method 4”).
Alternatively, for example, a compound represented by the formula (1′-7), a compound represented by the formula (1′-8), a compound represented by the formula (1′-1), and the formula (1 ′ -2), the compound (1 ′) can be synthesized by a coupling reaction once or twice or more (hereinafter referred to as “synthesis method 5”).
Alternatively, for example, a compound represented by the formula (1′-7), a compound represented by the formula (1′-10), a compound represented by the formula (1′-1), and the formula (1 ′ The compound (1 ′) can be synthesized by coupling the compound represented by -2) once or twice or more (hereinafter referred to as “synthesis method 6”).

In the synthesis method 3, for example, when Z ^C1 , Z ^C2 and Z ^C6 are groups selected from the substituent group A, Z ^C3 , Z ^C4 and Z ^C5 select groups selected from the substituent group B. For example, when Z ^C1 , Z ^C2 and Z ^C6 are groups selected from the substituent group B, Z ^C3 , Z ^C4 and Z ^C5 select a group selected from the substituent group A.

In Synthesis Method 4, for example, when Z ^C1 and Z ^C2 are groups selected from the substituent group A, Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 select a group selected from the substituent group B. For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group B, Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 select groups selected from the substituent group A.

In the synthesis method 5, for example, when Z ^C1 and Z ^C2 are groups selected from the substituent group A, Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 select groups selected from the substituent group B. For example, when Z ^C1 and Z ^C2 are groups selected from the substituent group B, Z ^C3 , Z ^C4 , Z ^C5 and Z ^C6 select groups selected from the substituent group A.

In the synthesis method 6, for example, when Z ^C1 , Z ^C2 and Z ^C6 are groups selected from the substituent group A, Z ^C3 , Z ^C4 and Z ^C5 select groups selected from the substituent group B. For example, when Z ^C1 , Z ^C2 and Z ^C6 are groups selected from the substituent group B, Z ^C3 , Z ^C4 and Z ^C5 select a group selected from the substituent group A.

[Method for Producing Compound of Formula (1 ″)]
Next, in the compound represented by the formula (1), a compound in which at least one of a plurality of L ¹ is a group represented by —N (R ^Z1 ) — (hereinafter referred to as “compound (1 ″)”). Will be described.

  For example, the compound (1 ″) is represented by the compound represented by the formula (1′-1) and / or the compound represented by the formula (1′-2) and the formula (1′-3). A compound, a compound represented by the formula (1′-4), and a compound represented by the formula (1′-11) can be synthesized by using a known coupling reaction or the like. it can.

［式中、Ｒ^Z1は前記と同じ意味を表す。］

[Wherein R ^Z1 represents the same meaning as described above. ]

[Synthesis Method 7]
For example, compound (1 ″) can be synthesized by a method similar to or similar to synthesis methods 1-6. In detail, for example, the compound represented by the formula (1′-1) and the compound represented by the formula (1′-11) are subjected to a coupling reaction once or twice or more to obtain the formula (1 A compound represented by '' -1) can be synthesized.

［式中、Ａｒ¹、Ｒ^Z1、ｎ¹及びＺ^C1は前記と同じ意味を表す。］

[Wherein, Ar ¹ , R ^Z1 , n ¹ and Z ^C1 represent the same meaning as described above. ]

  Next, the compound represented by the formula (1 ″ -1), the compound represented by the formula (1′-3), and the compound represented by the formula (1′-4) are once or Compound (1 ″) can be synthesized by a coupling reaction two or more times (hereinafter referred to as “synthesis method 7”).

In the synthesis method 7, for example, when Z ^C1 , Z ^C2 and Z ^C5 are groups selected from the substituent group A, Z ^C6 selects a group selected from the substituent group B.

[Common Description of Production Methods of Compound (1 ′) and Compound (1 ″)]
The group selected from the substituent group A is preferably a bromine atom, an iodine atom or a trifluoromethanesulfonyloxy group because the coupling reaction proceeds easily.

The group selected from the substituent group B is preferably a group represented by -B (OR ^C2 ) ₂ , more preferably a group represented by the formula (W-7).

  The coupling reaction is usually performed in a solvent. Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, ethylene glycol, glycerin, 2-methoxyethanol, and 2-ethoxyethanol; ethers such as diethyl ether, tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, and diglyme. Solvents: Halogen solvents such as methylene chloride and chloroform; Nitriles solvents such as acetonitrile and benzonitrile; Hydrocarbon solvents such as hexane, decalin, toluene, xylene and mesitylene; N, N-dimethylformamide, N, N- Amide solvents such as dimethylacetamide; acetone, dimethylsulfoxide, and water.

  In the coupling reaction, the reaction time is usually 30 minutes to 150 hours, and the reaction temperature is usually between the melting point and boiling point of the solvent present in the reaction system.

  In the coupling reaction, a catalyst such as a palladium catalyst may be used to accelerate the reaction. Examples of the palladium catalyst include palladium acetate, bis (triphenylphosphine) palladium (II) dichloride, tetrakis (triphenylphosphine) palladium (0), [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium ( II), tris (dibenzylideneacetone) dipalladium (0).

  The palladium catalyst may be used in combination with a phosphorus compound such as triphenylphosphine, tri (o-tolyl) phosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, 1,1′-bis (diphenylphosphino) ferrocene. .

  In the coupling reaction, if necessary, a palladium catalyst and a base may be used in combination.

  When the coupling reaction is performed twice or more, they may be reacted under the same conditions or may be reacted under different conditions.

  The compounds, catalysts and solvents used in each reaction described in <Method for producing compound represented by formula (1)> may be used alone or in combination of two or more.

  The compounds represented by formula (1'-1) to formula (1'-4) and formula (1'-11) can be obtained from Aldrich, Luminescence Technology Corp. Etc. are available.

  Moreover, it is also possible to manufacture by the well-known method as described in literatures, such as international publication 2002/045184, Unexamined-Japanese-Patent No. 2010-031259, Unexamined-Japanese-Patent No. 2012-144722, international publication 2002/066733. .

<Composition>
The composition of the present invention is at least selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material (different from the compound of the present invention), an antioxidant and a solvent. Contains one material and the compound of the present invention.

  In the composition of the present invention, the compound of the present invention may be contained singly or in combination of two or more.

[Host material]
The compound of the present invention is made into a composition with a host material having at least one function selected from the group consisting of hole injection property, hole transport property, electron injection property and electron transport property. The driving voltage of the light-emitting element obtained using is lower. In the composition of the present invention, the host material may be contained singly or in combination of two or more.

  In the composition containing the compound of the present invention and the host material, the content of the compound of the present invention is usually 0.05 to 80 parts by weight when the total of the compound of the present invention and the host material is 100 parts by weight. Yes, preferably 0.1 to 50 parts by weight, more preferably 1 to 30 parts by weight, and even more preferably 5 to 20 parts by weight.

Since the lowest excited singlet state (S ₁ ) of the host material has excellent external quantum efficiency of the light-emitting device obtained using the composition of the present invention, the energy level equivalent to S ₁ of the compound of the present invention, Or it is preferable that it is a higher energy level.

  As a host material, a light-emitting element obtained using a composition containing the compound of the present invention can be produced by a solution coating process, and therefore, exhibits solubility in a solvent capable of dissolving the compound of the present invention. Preferably there is.

  The host material is classified into a low molecular compound and a high molecular compound, and is preferably a high molecular compound.

  As a host material, the below-mentioned hole transport material and the below-mentioned electron transport material are mentioned, for example.

[Polymer host]
A polymer compound preferable as a host material (hereinafter referred to as “polymer host”) will be described.

  The polymer host is preferably a polyvinyl carbazole, a polyvinyl carbazole derivative, or a polymer compound containing a structural unit represented by the formula (Y), more preferably a structural unit represented by the formula (Y). It is a high molecular compound containing.

［式中、Ａｒ^Y1は、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。］

[In the formula, Ar ^Y1 represents an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded, and these This group may have a substituent. ]

The arylene group represented by Ar ^Y1 is more preferably a formula (A-1), a formula (A-6), a formula (A-7), a formula (A-9) to a formula (A-11), a formula (A A-14) or a group represented by formula (A-19), more preferably formula (A-1), formula (A-7), formula (A-9), formula (A-11) or A group represented by formula (A-19), and these groups each optionally have a substituent;

More preferably, the divalent heterocyclic group represented by Ar ^Y1 is represented by the formula (AA-4), formula (AA-10), formula (AA-13), formula (AA-15), formula (AA-18) ) Or a group represented by formula (AA-20), particularly preferably represented by formula (AA-4), formula (AA-10), formula (AA-18) or formula (AA-20) These groups may have a substituent.

More preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded, and further preferable. The ranges are the same as the more preferable ranges and further preferable ranges of the arylene group and divalent heterocyclic group represented by Ar ^Y1 described later.

The divalent group in which at least one arylene group represented by Ar ^Y1 and at least one divalent heterocyclic group are directly bonded to each other is at least represented by Ar ^X2 and Ar ^X4 in the formula (X). Examples thereof include the same divalent groups in which one kind of arylene group and at least one kind of divalent heterocyclic group are directly bonded.

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

  Examples of the structural unit represented by the formula (Y) include structural units represented by the formula (Y-1) to the formula (Y-7), and contain the polymer host and the compound of the present invention. Since the driving voltage of the light-emitting element using the composition is further reduced, it is preferably a structural unit represented by the formula (Y-1) or the formula (Y-2), and the electron transport property of the polymer host From the viewpoint, it is preferably a structural unit represented by formula (Y-3) or formula (Y-4), and from the viewpoint of hole transport properties of the polymer host, preferably from formula (Y-5) to It is a structural unit represented by Formula (Y-7).

［式中、Ｒ^Y1は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y1は、同一でも異なっていてもよく、隣接するＲ^Y1同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[Wherein, R ^Y1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. . A plurality of R ^Y1 may be the same or different, and adjacent R ^Y1 may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

R ^Y1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, and these groups optionally have a substituent.

  The structural unit represented by the formula (Y-1) is preferably a structural unit represented by the formula (Y-1 ′).

［式中、Ｒ^Y11は、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y11は、同一でも異なっていてもよい。］

[Wherein, R ^Y11 represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. A plurality of R ^Y11 may be the same or different. ]

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

［式中、
Ｒ^Y1は前記と同じ意味を表す。
Ｘ^Y1は、−Ｃ(Ｒ^Y2)₂−、−Ｃ(Ｒ^Y2)＝Ｃ(Ｒ^Y2)−又は−Ｃ(Ｒ^Y2)₂−Ｃ(Ｒ^Y2)₂−で表される基を表す。Ｒ^Y2は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。複数存在するＲ^Y2は、同一でも異なっていてもよく、Ｒ^Y2同士は互いに結合して、それぞれが結合する炭素原子と共に環を形成していてもよい。］

[Where:
R ^Y1 represents the same meaning as described above.
X ^{Y1 _{is, -C (R Y2) 2 -}} , - represents a group represented by ^{- C (R Y2) = C} (R Y2) - , or _{^{-C (R Y2) 2 -C (}} R Y2) 2. R ^Y2 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. A plurality of R ^Y2 may be the same or different, and R ^Y2 may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

R ^Y2 is preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an alkyl group, a cycloalkyl group or an aryl group, and these groups have a substituent. May be.

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ₂ — is preferably an alkyl group or a cycloalkyl group, both are aryl groups, and both are monovalent complex. A cyclic group, or one is an alkyl group or a cycloalkyl group, the other is an aryl group or a monovalent heterocyclic group, more preferably one is an alkyl group or a cycloalkyl group, and the other is an aryl group. May have a substituent. Two R ^{Y2 s} may be bonded to each other to form a ring together with the atoms to which they are bonded, and when R ^Y2 forms a ring, the group represented by —C (R ^Y2 ) ₂ — Is preferably a group represented by formula (Y-A1) to formula (Y-A5), more preferably a group represented by formula (Y-A4), and these groups have a substituent. You may do it.

In X ^Y1 , the combination of two R ^{Y2 in} the group represented by —C (R ^Y2 ) ═C (R ^Y2 ) — is preferably both an alkyl group or a cycloalkyl group, or one of which is an alkyl group Alternatively, a cycloalkyl group and the other is an aryl group, and these groups may have a substituent.

In X ^Y1 , four R ^Y2 in the group represented by —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — are preferably an alkyl group or a cycloalkyl group which may have a substituent. It is. A plurality of R ^Y2 may be bonded to each other to form a ring together with the atoms to which each is bonded. When R ^Y2 forms a ring, —C (R ^Y2 ) ₂ —C (R ^Y2 ) ₂ — The group represented is preferably a group represented by the formula (Y-B1) to the formula (Y-B5), more preferably a group represented by the formula (Y-B3), and these groups are It may have a substituent.

［式中、Ｒ^Y2は前記と同じ意味を表す。］

[Wherein, R ^Y2 represents the same meaning as described above. ]

  The structural unit represented by the formula (Y-2) is preferably a structural unit represented by the formula (Y-2 ′).

［式中、Ｒ^Y1及びＸ^Y1は前記と同じ意味を表す。］

[Wherein, R ^Y1 and X ^Y1 represent the same meaning as described above. ]

［式中、
Ｒ^Y1は前記と同じ意味を表す。
Ｒ^Y3は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[Where:
R ^Y1 represents the same meaning as described above.
R ^Y3 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups may have a substituent. ]

R ^Y3 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be.

［式中、
Ｒ^Y1は前記を同じ意味を表す。
Ｒ^Y4は、水素原子、アルキル基、シクロアルキル基、アルコキシ基、シクロアルコキシ基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。］

[Where:
R ^Y1 represents the same meaning as described above.
R ^Y4 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, or a monovalent heterocyclic group, and these groups optionally have a substituent. ]

R ^Y4 is preferably an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. May be.

  Examples of the structural unit represented by Formula (Y) include structural units represented by Formula (Y-11) to Formula (Y-55), and structural units derived from Compound CM1 and Compound CM2 described below. Can be mentioned.

The structural unit represented by the formula (Y), in which Ar ^Y1 is an arylene group, has a lower driving voltage of a light emitting device using a composition containing a polymer host and the compound of the present invention. Therefore, it is preferably 10 to 100 mol%, more preferably 50 to 100 mol%, based on the total amount of the structural units contained in the polymer compound.

A structural unit represented by the formula (Y), wherein Ar ^Y1 is a divalent heterocyclic group, or at least one arylene group and at least one divalent heterocyclic group are directly bonded. The structural unit which is a group is preferably 0.5 to 40 mol%, more preferably 3 to 30%, based on the total amount of the structural units contained in the polymer host, since the charge transport property of the polymer host is excellent. Mol%.

  One type of structural unit represented by the formula (Y) may be contained in the polymer host, or two or more types may be contained.

  Since the polymer host is excellent in hole transportability, it is preferable that the polymer host further includes a structural unit represented by the formula (X).

［式中、
ａ¹及びａ²は、それぞれ独立に、０以上の整数を表す。
Ａｒ^X1及びＡｒ^X3は、それぞれ独立に、アリーレン基又は２価の複素環基を表し、これらの基は置換基を有していてもよい。
Ａｒ^X2及びＡｒ^X4は、それぞれ独立に、アリーレン基、２価の複素環基、又は、少なくとも１種のアリーレン基と少なくとも１種の２価の複素環基とが直接結合した２価の基を表し、これらの基は置換基を有していてもよい。Ａｒ^X2及びＡｒ^X4が複数存在する場合、それらは同一でも異なっていてもよい。
Ｒ^X1、Ｒ^X2及びＲ^X3は、それぞれ独立に、水素原子、アルキル基、シクロアルキル基、アリール基又は１価の複素環基を表し、これらの基は置換基を有していてもよい。Ｒ^X2及びＲ^X3が複数存在する場合、それらは同一でも異なっていてもよい。］

[Where:
a ¹ and a ² each independently represent an integer of 0 or more.
Ar ^X1 and Ar ^X3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent.
Ar ^X2 and Ar ^X4 each independently represent an arylene group, a divalent heterocyclic group, or a divalent group in which at least one arylene group and at least one divalent heterocyclic group are directly bonded. And these groups may have a substituent. When there are a plurality of Ar ^X2 and Ar ^X4 , they may be the same or different.
R ^X1 , R ^X2 and R ^X3 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, and these groups may have a substituent. When there are a plurality of R ^X2 and R ^X3 , they may be the same or different. ]

a ^X1 is preferably 2 or less, more preferably 1 because the luminance life of the light-emitting device using the composition containing the polymer host and the compound of the present invention is more excellent.

a ^X2 is preferably 2 or less, more preferably 0, because the luminance life of a light emitting device using a composition containing a polymer host and the compound of the present invention is more excellent.

R ^X1 , R ^X2 and R ^X3 are preferably an alkyl group, a cycloalkyl group, an aryl group or a monovalent heterocyclic group, more preferably an aryl group, and these groups have a substituent. Also good.

The arylene group represented by Ar ^X1 and Ar ^X3 is more preferably a group represented by the formula (A-1) or the formula (A-9), and more preferably a formula (A-1). These groups may have a substituent.

The divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 is more preferably represented by Formula (AA-1), Formula (AA-2), or Formula (AA-7) to Formula (AA-26). These groups may have a substituent.

Ar ^X1 and Ar ^X3 are preferably an arylene group which may have a substituent.

More preferably, the arylene group represented by Ar ^X2 and Ar ^X4 is represented by formula (A-1), formula (A-6), formula (A-7), formula (A-9) to formula (A-11). Or it is group represented by a formula (A-19), and these groups may have a substituent.

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

More preferable range of the arylene group and the divalent heterocyclic group in the divalent group in which at least one kind of arylene group represented by Ar ^X2 and Ar ^X4 and at least one kind of divalent heterocyclic group are directly bonded. Further preferred ranges are the same as the more preferred ranges and further preferred ranges of the arylene group and divalent heterocyclic group represented by Ar ^X1 and Ar ^X3 , respectively.

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

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

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

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

Ar ^X2 and Ar ^X4 are preferably an arylene group which may have a substituent.

The substituents that the groups represented by Ar ^{X1 to} Ar ^X4 and R ^{X1 to} R ^X3 may have are preferably an alkyl group, a cycloalkyl group, or an aryl group, and these groups further have a substituent. You may do it.

  The structural unit represented by the formula (X) is preferably a structural unit represented by the formula (X-1) to the formula (X-7), more preferably the formula (X-3) to the formula (X -7), more preferably structural units represented by formula (X-3) to formula (X-6).

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

[Wherein, R ^X4 and R ^X5 each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, an aryl group, an aryloxy group, a halogen atom, a monovalent heterocyclic group or cyano. Represents a group, and these groups may have a substituent. A plurality of R ^X4 may be the same or different. A plurality of R ^X5 may be the same or different, and adjacent R ^X5 may be bonded to each other to form a ring together with the carbon atom to which each is bonded. ]

  The structural unit represented by the formula (X) is preferably 0.1 to 50 mol% with respect to the total amount of the structural units contained in the polymer host because the hole transport property of the polymer host is excellent. Preferably it is 1-40 mol%, More preferably, it is 5-30 mol%.

  Examples of the structural unit represented by the formula (X) include structural units represented by the formula (X1-1) to the formula (X1-19), preferably the formula (X1-6) to the formula (X1 -14).

  In the polymer host, the structural unit represented by the formula (X) may be included alone or in combination of two or more.

  Examples of the polymer host include polymer compounds (P-1) to (P-6). Here, the “other” structural unit means a structural unit other than the structural unit represented by the formula (Y) and the structural unit represented by the formula (X).

［表中、ｐ、ｑ、ｒ、ｓ及びｔは、各構成単位のモル比率を示す。ｐ＋ｑ＋ｒ＋ｓ＋ｔ＝100であり、かつ、100≧ｐ＋ｑ＋ｒ＋ｓ≧70である。］

[In the table, p, q, r, s and t represent the molar ratio of each constituent unit. p + q + r + s + t = 100 and 100 ≧ p + q + r + s ≧ 70. ]

  The polymer host may be any of a block copolymer, a random copolymer, an alternating copolymer, and a graft copolymer, and may be in other modes. A copolymer obtained by polymerization is preferred.

<Method for producing polymer host>
The polymer host can be produced by using a known polymerization method described in Chemical Review (Chem. Rev.), Vol. 109, pp. 897-1091 (2009), etc., and Suzuki reaction, Yamamoto reaction, Buchwald Examples thereof include a polymerization method by a coupling reaction using a transition metal catalyst such as a reaction, Stille reaction, Negishi reaction, and Kumada reaction.

  In the polymerization method, examples of the method for charging the monomer include, for example, a method in which the entire amount of the monomer is charged into the reaction system at once, a part of the monomer is charged and reacted, and then the remaining monomer is charged. Examples thereof include a method of charging in a lump, continuous or divided manner, and a method of charging monomers in a continuous or divided manner.

  Examples of the transition metal catalyst include a palladium catalyst and a nickel catalyst.

  Post-treatment of the polymerization reaction is a known method, for example, a method of removing water-soluble impurities by liquid separation, adding the reaction solution after polymerization reaction to a lower alcohol such as methanol, filtering the deposited precipitate, and then drying. These methods are performed alone or in combination. When the purity of the polymer host is low, it can be purified by usual methods such as crystallization, reprecipitation, continuous extraction with a Soxhlet extractor, column chromatography, and the like.

  A composition containing the compound of the present invention and a solvent (hereinafter referred to as “ink”) is suitable for production of a light-emitting element using a printing method such as an inkjet printing method or a nozzle printing method.

  The viscosity of the ink may be adjusted according to the type of printing method, but when a solution such as an ink jet printing method is applied to a printing method that passes through a discharge device, clogging and flight bending at the time of discharge are less likely to occur. Preferably, it is 1 to 20 mPa · s at 25 ° C.

  The solvent contained in the ink is preferably a solvent that can dissolve or uniformly disperse the solid content in the ink. Examples of the solvent include chlorine solvents such as 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; ether solvents such as THF, dioxane, anisole and 4-methylanisole; Aromatic hydrocarbon solvents such as xylene, mesitylene, ethylbenzene, n-hexylbenzene, cyclohexylbenzene; cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n- Aliphatic hydrocarbon solvents such as decane, n-dodecane, and bicyclohexyl; ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; esters such as ethyl acetate, butyl acetate, ethyl cellosolve acetate, methyl benzoate, and phenyl acetate Solvents: ethylene glycol, glycerin, 1,2-hex Examples include polyhydric alcohol solvents such as sundiol; alcohol solvents such as isopropyl alcohol and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide. It is done. A solvent may be used individually by 1 type, or may use 2 or more types together.

  In the ink, the amount of the solvent is usually 1000 to 100,000 parts by weight, preferably 2000 to 20000 parts by weight, with respect to 100 parts by weight of the compound of the present invention.

[Hole transport material]
The hole transport material is classified into a low molecular compound and a high molecular compound, preferably a high molecular compound, and more preferably a high molecular compound having a crosslinking group.

  Examples of the polymer compound include polyvinyl carbazole and derivatives thereof; polyarylene having an aromatic amine structure in the side chain or main chain and derivatives thereof. The polymer compound may be a compound to which an electron accepting site is bonded. Examples of the electron accepting site include fullerene, tetrafluorotetracyanoquinodimethane, tetracyanoethylene, and trinitrofluorenone, and fullerene is preferable.

  In the composition of the present invention, the compounding amount of the hole transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight with respect to 100 parts by weight of the compound of the present invention.

  A hole transport material may be used individually by 1 type, or may use 2 or more types together.

[Electron transport materials]
Electron transport materials are classified into low molecular compounds and high molecular compounds. The electron transport material may have a crosslinking group.

  Low molecular weight compounds include, for example, metal complexes having 8-hydroxyquinoline as a ligand, oxadiazole, anthraquinodimethane, benzoquinone, naphthoquinone, anthraquinone, tetracyanoanthraquinodimethane, fluorenone, diphenyldicyanoethylene, and diphenoquinone. As well as these derivatives.

  Examples of the polymer compound include polyphenylene, polyfluorene, and derivatives thereof. The polymer compound may be doped with a metal.

  In the composition of the present invention, the amount of the electron transport material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, based on 100 parts by weight of the compound of the present invention.

  An electron transport material may be used individually by 1 type, or may use 2 or more types together.

[Hole injection material and electron injection material]
The hole injection material and the electron injection material are classified into a low molecular compound and a high molecular compound, respectively. The hole injection material and the electron injection material may have a crosslinking group.

  Examples of the low molecular weight compound include metal phthalocyanines such as copper phthalocyanine; carbon; metal oxides such as molybdenum and tungsten; and metal fluorides such as lithium fluoride, sodium fluoride, cesium fluoride, and potassium fluoride.

  Examples of the polymer compound include polyaniline, polythiophene, polypyrrole, polyphenylene vinylene, polythienylene vinylene, polyquinoline and polyquinoxaline, and derivatives thereof; conductive polymers such as polymers containing an aromatic amine structure in the main chain or side chain. A functional polymer.

  In the composition of the present invention, the amount of the hole injection material and the electron injection material is usually 1 to 400 parts by weight, preferably 5 to 150 parts by weight, with respect to 100 parts by weight of the compound of the present invention. It is.

  Each of the hole injection material and the electron injection material may be used alone or in combination of two or more.

[Ion dope]
When the hole injection material or the electron injection material contains a conductive polymer, the electrical conductivity of the conductive polymer is preferably 1 × 10 ⁻⁵ S / cm to 1 × 10 ³ S / cm. In order to make the electric conductivity of the conductive polymer within such a range, the conductive polymer can be doped with an appropriate amount of ions.

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

  Doping ions may be used alone or in combination of two or more.

[Luminescent material]
Luminescent materials (different from the compounds of the present invention) are classified into low molecular compounds and high molecular compounds. The light emitting material may have a crosslinking group.

  Examples of the low molecular weight compound include naphthalene and derivatives thereof, anthracene and derivatives thereof, perylene and derivatives thereof, and triplet light-emitting complexes having iridium, platinum, or europium as a central metal.

  Examples of the polymer compound include a phenylene group, a naphthalenediyl group, a fluorenediyl group, a phenanthrene diyl group, a dihydrophenanthrene diyl group, a group represented by the formula (X), a carbazole diyl group, a phenoxazine diyl group, and a phenothiazine diyl. And polymer compounds containing a group, an anthracenediyl group, a pyrenediyl group, and the like.

  The light emitting material preferably contains a triplet light emitting complex and a polymer compound.

  Examples of the triplet luminescent complex include the metal complexes shown below.

  In the composition of the present invention, the content of the luminescent material is usually 0.1 to 400 parts by weight with respect to 100 parts by weight of the compound of the present invention.

[Antioxidant]
The antioxidant may be any compound that is soluble in the same solvent as the compound of the present invention and does not inhibit light emission and charge transport. Examples thereof include phenol-based antioxidants and phosphorus-based antioxidants.

  In the composition of the present invention, the blending amount of the antioxidant is usually 0.001 to 10 parts by weight with respect to 100 parts by weight of the compound of the present invention.

  Antioxidants may be used alone or in combination of two or more.

<Membrane>
The membrane contains a compound of the present invention.

  The film is suitable as a light emitting layer in a light emitting element.

  The film is made of ink, for example, 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 printing, offset printing, ink jet printing, capillary coating, and nozzle coating.

  The thickness of the film is usually 1 nm to 10 μm.

<Light emitting element>
The light emitting device of the present invention is a light emitting device containing the compound of the present invention.
As a structure of the light emitting element of this invention, it has the electrode which consists of an anode and a cathode, for example, and the layer containing the compound of this invention provided between this electrode.

[Layer structure]
The layer containing the compound of the present invention is usually one or more of a light emitting layer, a hole transport layer, a hole injection layer, an electron transport layer, and an electron injection layer, and is preferably a light emitting layer. Each of these layers includes a light emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material. Each of these layers is the same as the above-described film production, in which a light-emitting material, a hole transport material, a hole injection material, an electron transport material, and an electron injection material are dissolved in the above-described solvent and ink is prepared and used. It can be formed using a method.

  The light emitting element has a light emitting layer between an anode and a cathode. The light emitting device of the present invention preferably has at least one of a hole injection layer and a hole transport layer between the anode and the light emitting layer from the viewpoint of hole injection and hole transport. From the viewpoint of injection property and electron transport property, it is preferable to have at least one of an electron injection layer and an electron transport layer between the cathode and the light emitting layer.

  Examples of materials for the hole transport layer, the electron transport layer, the light emitting layer, the hole injection layer, and the electron injection layer include, for example, the above-described hole transport material, electron transport material, light emitting material, in addition to the compound of the present invention, respectively. Examples include hole injection materials and electron injection materials.

  The material of the hole transport layer, the material of the electron transport layer, and the material of the light emitting layer are used as solvents used in forming the layer adjacent to the hole transport layer, the electron transport layer, and the light emitting layer, respectively, in the production of the light emitting element. When dissolved, the material preferably has a cross-linking group in order to avoid dissolution of the material in the solvent. After forming each layer using a material having a crosslinking group, the layer can be insolubilized by crosslinking the crosslinking group.

  In the light emitting device of the present invention, as a method for forming each layer such as a light emitting layer, a hole transport layer, an electron transport layer, a hole injection layer, and an electron injection layer, when using a low molecular compound, for example, vacuum deposition from powder For example, a method using film formation from a solution or a molten state may be used.

  The order, number, and thickness of the layers to be laminated are adjusted in consideration of the external quantum efficiency and the luminance lifetime.

[Substrate / Electrode]
The substrate in the light-emitting element may be any substrate that can form electrodes and does not change chemically when the organic layer is formed. For example, the substrate is made of a material such as glass, plastic, or silicon. In the case of an opaque substrate, the electrode farthest from the substrate is preferably transparent or translucent.

  Examples of the material for the anode include conductive metal oxides and translucent metals, preferably indium oxide, zinc oxide, tin oxide; indium tin oxide (ITO), indium zinc oxide, etc. A conductive compound of silver, palladium and copper (APC); NESA, gold, platinum, silver and copper.

Examples of the material of the cathode include metals such as lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, zinc, indium; two or more kinds of alloys thereof; Alloys of at least one species and at least one of silver, copper, manganese, titanium, cobalt, nickel, tungsten, and tin; and graphite and graphite intercalation compounds. Examples of the alloy include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.
Each of the anode and the cathode may have a laminated structure of two or more layers.

[Usage]
In order to obtain planar light emission using the light emitting element, the planar anode and the cathode may be arranged so as to overlap each other. In order to obtain pattern-like light emission, a method in which a mask having a pattern-like window is provided 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. There is a method, a method of forming an anode or a cathode, or both electrodes in a pattern. By forming a pattern by any of these methods and arranging several electrodes so that they can be turned on and off independently, a segment type display device capable of displaying numbers, characters, and the like can be obtained. In order to obtain a dot matrix display device, both the anode and the cathode may be formed in stripes and arranged orthogonally. Partial color display and multicolor display are possible by a method of separately coating a plurality of types of polymer compounds having different emission colors, or a method using a color filter or a fluorescence conversion filter. The dot matrix display device can be driven passively, or can be driven active in combination with a TFT or the like. These display devices can be used for displays of computers, televisions, portable terminals and the like. The planar light emitting element can be suitably used as a planar light source for 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 and display device.

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

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

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

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

TLC-MS was measured by the following method.
A measurement sample is dissolved in any solvent of toluene, tetrahydrofuran, or chloroform at an arbitrary concentration, and coated on a TART plate for DART (manufactured by Techno Applications, trade name: YSK5-100), and TLC-MS (JEOL Ltd.) Product name: JMS-T100TD (The AccuTOF TLC)). The helium gas temperature at the time of measurement was adjusted in the range of 200 to 400 ° C.

NMR was measured by the following method.
About 0.5 mL of deuterated chloroform (CDCl ₃ ), deuterated tetrahydrofuran, deuterated dimethyl sulfoxide, deuterated acetone, deuterated N, N-dimethylformamide, deuterated toluene, deuterated methanol, deuterated ethanol, deuterated 2-propanol. Alternatively, it was dissolved in methylene chloride and measured using an NMR apparatus (manufactured by Agilent, trade name: INOVA300 or MERCURY 400VX).

  A high performance liquid chromatography (HPLC) area percentage value was used as an indicator of the purity of the compound. Unless otherwise specified, this value is a value at UV = 254 nm in HPLC (manufactured by Shimadzu Corporation, trade name: LC-20A). At this time, the compound to be measured was dissolved in tetrahydrofuran or chloroform so that the concentration was 0.01 to 0.2% by weight, and 1 to 10 μL was injected into the HPLC depending on the concentration. The HPLC mobile phase was used by changing the ratio of acetonitrile / tetrahydrofuran from 100/0 to 0/100 (volume ratio) and flowing at a flow rate of 1.0 mL / min. As the column, Kaseisorb LC ODS 2000 (manufactured by Tokyo Chemical Industry Co., Ltd.) or an ODS column having equivalent performance was used. As a detector, a photodiode array detector (manufactured by Shimadzu Corporation, trade name: SPD-M20A) was used.

<Synthesis Example 1> Synthesis of Polymer Compound HP-1 Compound CM1 (1.73 g) and Compound CM2 (synthesized according to the method described in JP 2012-144721 A were prepared after setting the inside of the reaction vessel to an inert gas atmosphere. 0.843 g), dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.2 mg) and toluene (40 ml) were added and heated to 105 ° C.

A 20 wt% tetraethylammonium hydroxide aqueous solution (8.7 g) was added dropwise to the resulting reaction solution, and the mixture was refluxed for 3 hours.
Thereafter, 9-bromoanthracene (64.1 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (8.8 g) and dichlorobis [tris (2-methoxyphenyl) phosphine] palladium (2.2 mg) were added thereto. Reflux for hours.
Thereafter, a sodium diethyldithiacarbamate aqueous solution was added thereto, followed by stirring at 80 ° C. for 2 hours. The obtained reaction solution was cooled, then washed twice with water, twice with a 3% by weight aqueous acetic acid solution and twice with water, and the resulting solution was added dropwise to methanol, resulting in precipitation. The precipitate was dissolved in toluene and purified by passing through an alumina column and a silica gel column in this order. When the obtained solution was added dropwise to methanol and stirred, precipitation occurred. The precipitate was collected by filtration and dried to obtain 0.91 g of the polymer compound HP-1. The number average molecular weight and weight average molecular weight in terms of polystyrene of the polymer compound HP-1 were Mn = 1.2 × 10 ⁵ and Mw = 4.8 × 10 ⁵ , respectively.

  The polymer compound HP-1 has a theoretical value obtained from the amount of the raw material charged, and the structural unit derived from the compound CM1 and the structural unit derived from the compound CM2 are configured in a molar ratio of 50:50. It is a copolymer.

<Synthesis Example 2> Synthesis of polymer compound HTL-1

  The polymer compound HTL-1 is compounded in Compound CM3 synthesized according to the method described in International Publication No. 2002/045184, Compound CM4 synthesized in accordance with the method described in International Publication No. 2002/045184, and International Publication No. 2011/049241. Using compound CM5 synthesized according to the described method, the compound was synthesized according to the method described in International Publication No. 2011/049241.

The number average molecular weight and weight average molecular weight in terms of polystyrene of the polymer compound HTL-1 were Mn = 8.9 × 10 ⁴ and Mw = 4.2 × 10 ⁵ , respectively.

  The theoretical value obtained from the amount of the raw material used for the polymer compound HTL-1 includes a structural unit derived from the compound CM3, a structural unit derived from the compound CM4, and a structural unit derived from the compound CM5. It is a copolymer composed of a molar ratio of 50: 42.5: 7.5.

Example 1 Synthesis of Compound EM1 (Synthesis of Compound EM1b)

After making the inside of the reaction vessel a nitrogen atmosphere, compound EM1a (50.0 g), bis (pinacolato) diboron (26.6 g), [1,1′-bis synthesized according to the method described in JP2010-031259A (Diphenylphosphino) ferrocene] palladium (II) dichloride / dichloromethane complex (PdCl ₂ (dppf) · CH ₂ Cl ₂ , 1.49 g), potassium acetate (26.8 g) and 1,4-dioxane (350 mL) were added. The mixture was stirred for 4 hours under heating to reflux. Then, after cooling to room temperature, ethyl acetate was added, and the reaction solution was washed with ion-exchanged water. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel column chromatography (mixed solvent of hexane and toluene), recrystallized using a mixed solvent of toluene and ethyl acetate, and dried to obtain compound EM1b (12.5 g, white solid). Obtained. The HPLC area percentage value of Compound EM1b was 99.5% or more.

LC-MS (ESI, positive): m / z = 1192 [M] ⁺

(Synthesis of Compound EM1e)

  After making the inside of reaction container argon atmosphere, compound EM1c (8.23g) synthesize | combined according to the method of Unexamined-Japanese-Patent No. 2012-144722, Compound EM1d synthesize | combined according to the method of Unexamined-Japanese-Patent No. 2012-144722 (2.44 g), tetrakis (triphenylphosphine) palladium (0) (0.204 g), 20 wt% tetraethylammonium hydroxide aqueous solution (1.56 g), toluene (45 mL), tert-butyl alcohol (25 mL), ion Exchange water (13 mL) and tetrahydrofuran (23 mL) were added, and the mixture was stirred at 85 ° C. for 2 hours. Thereafter, after cooling to room temperature, the reaction solution was washed with ion-exchanged water. The obtained organic layer was concentrated under reduced pressure to obtain a solid. The solid was purified by silica gel (ODS) column chromatography (mixed solvent of acetonitrile and tetrahydrofuran) to obtain Compound EM1e (2.74 g, yellow solid). The HPLC area percentage value of Compound EM1e was 99.5% or more.

¹ H-NMR (300 MHz, CDCl ₃ ): δ = 0.76-0.86 (m, 20H), 1.10-1.29 (m, 42H), 1.47-1.54 (m, 8H) ), 1.88 (s, 6H), 2.45-2.50 (m, 12H), 6.79-6.84 (m, 6H), 6.97-6.99 (m, 2H), 7.06-7.13 (m, 2H), 5.35 (d, 2H), 7.43-7.47 (m, 6H), 7.52-7.56 (m, 4H), 7. 61 (d, 2H), 7.74 (d, 4H).
LC-MS (ESI, positive): m / z = 1439 [M] ⁺

(Synthesis of Compound EM1f)

  After making the inside of reaction container argon atmosphere, compound EM1b (1.53g), compound EM1e (7.40g), tetrakis (triphenylphosphine) palladium (0) (74.2mg), 20 weight% tetraethylammonium hydroxide aqueous solution (0.76 g), toluene (15 mL), tert-butyl alcohol (9 mL), ion-exchanged water (4.5 mL) and tetrahydrofuran (7.5 mL) were added, and the mixture was stirred at 80 ° C. for 2 hours. Then, after cooling to room temperature, ethyl acetate was added, and the reaction solution was washed with ion-exchanged water. The obtained organic layer was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel (ODS) column chromatography (mixed solvent of acetonitrile and tetrahydrofuran) to obtain Compound EM1f (2.5 g, yellow solid). The HPLC area percentage value of Compound EM1f was 99.5% or more.

(Synthesis of Compound EM1)

  After making the inside of reaction container argon atmosphere, compound EM1f (0.50 g), phenylboronic acid (66.6 mg), tetrakis (triphenylphosphine) palladium (0) (7.89 mg), 20 wt% tetraethylammonium hydroxide An aqueous solution (80.4 mg), toluene (6 mL), tert-butyl alcohol (3 mL), ion-exchanged water (2 mL) and tetrahydrofuran (3 mL) were added, and the mixture was stirred at 90 ° C. for 2 hr. Then, after cooling to room temperature, ion-exchange water was added, and it filtered with the filter which spread | laid silica gel. The obtained filtrate was concentrated under reduced pressure to obtain a solid. The solid was purified by silica gel column chromatography (a mixed solvent of hexane and ethyl acetate), recrystallized using a mixed solvent of tetrahydrofuran and isopropanol, and dried to obtain Compound EM1 (450 mg, yellow solid). . The HPLC area percentage value of Compound EM1 was 99.5% or more.

¹ H-NMR (300 MHz, CDCl ₃ ): δ = 0.76-0.85 (m, 40H), 1.10-1.23 (m, 76H), 1.37 (s, 36H), 1. 43-1.53 (m, 24H), 1.91-1.94 (m, 12H), 2.44-2.50 (m, 24H), 6.19 (m, 2H), 6.81- 7.14 (m, 24H), 7.29-7.84 (m, 70H), 8.13 (s, 1H).

Example 2 Synthesis of Compound EM2 (Synthesis of Compound EM2b)

  After making the inside of the reaction vessel a nitrogen atmosphere, compound EM1c (5.00 g), compound EM2a (4.94 g), dichlorobis (triphenylphosphine) palladium (II) synthesized according to the method described in JP 2012-144722 A (0.121 g), 20 wt% tetraethylammonium hydroxide aqueous solution (2.53 g) and toluene (200 mL) were added, and the mixture was stirred at 55 ° C. for 2 hours. Then, after cooling to room temperature, ion-exchange water was added, and it filtered with the filter which spread celite. After removing the aqueous layer from the obtained filtrate, the obtained organic layer was concentrated under reduced pressure. Hexane, toluene, and activated carbon were added thereto, and the mixture was stirred at room temperature for 1 hour, filtered through a filter with celite, and the filtrate was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene, and a mixed solvent of hexane and ethyl acetate) to obtain a crude product. The crude product was washed with a mixed solvent of acetone and hexane to obtain a solid. To this solid was added hexane, toluene and activated carbon, and the mixture was stirred at room temperature for 1 hour, filtered through a filter with silica gel and celite, and the filtrate was concentrated under reduced pressure to obtain Compound EM2b (2.5 g). It was. The HPLC area percentage value of Compound EM2b was 99.25%.

LC-MS (ESI, positive): m / z = 1259 [M] ⁺

(Synthesis of Compound EM2)

  After making the inside of reaction container nitrogen atmosphere, compound EM2b (2.45 g), compound EM1b (1.16 g), dichlorobis (triphenylphosphine) palladium (II) (55 mg), 20 wt% tetraethylammonium hydroxide aqueous solution (1 .15 g) and toluene (25 mL) were added, and the mixture was stirred at 55 ° C. for 2 hours. Then, after cooling to room temperature, ion-exchange water was added, and it filtered with the filter which spread celite. After removing the aqueous layer from the obtained filtrate, the obtained organic layer was concentrated under reduced pressure. Toluene and activated carbon were added thereto, and the mixture was stirred at 40 ° C. for 1 hour, filtered through a filter with celite, and the filtrate was concentrated under reduced pressure to obtain a solid. This solid was purified by silica gel column chromatography (a mixed solvent of hexane and toluene), further washed with methanol, and dried to obtain Compound EM2 (0.83 g). The HPLC area percentage value of Compound EM2 was 99.5% or more.

¹ H-NMR (300 MHz, CDCl ₃ ): δ = 0.75 (t, 12H), 1.17-1.59 (m, 140H), 1.95 (s, 6H), 2.44 (t, 8H), 6.20 (d, 2H), 6.77-7.01 (m, 10H), 7.39-7.91 (m, 86H), 8.13 (s, 1H).
LC-MS (ESI, positive): m / z = 3297 [M] ⁺

<Example D1> Fabrication and evaluation of light-emitting element D1 (formation of anode and hole injection layer)
An anode was formed by attaching an ITO film with a thickness of 45 nm to the glass substrate by sputtering. AQ-1200 (manufactured by Plextronics), which is a polythiophene / sulfonic acid-based hole injecting agent, was formed on the anode at a thickness of 35 nm by a spin coating method, and 170 ° C. on a hot plate in an air atmosphere. The hole injection layer was formed by heating for 15 minutes.

(Formation of hole transport layer)
The polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm was formed on the hole injection layer by spin coating, and heated at 180 ° C. for 60 minutes on a hot plate in a nitrogen gas atmosphere. A transport layer was formed.

(Formation of light emitting layer)
To chlorobenzene, poly (9-vinylcarbazole) (polymer compound PVK) (manufactured by Sigma-Aldrich, weight average molecular weight to 1.1 × 10 ⁶ , powder) and compound EM1 (polymer compound PVK / compound EM1 = 90) % By weight / 10% by weight) was dissolved at a concentration of 1.3% by weight. Using the obtained chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coating method, and a light emitting layer was formed by heating at 150 ° C. for 10 minutes in a nitrogen gas atmosphere.

(Formation of cathode)
After depressurizing the substrate on which the light emitting layer is formed to 1.0 × 10 ⁻⁴ Pa or less in a vapor deposition machine, sodium fluoride is about 4 nm on the light emitting layer as a cathode, and then on the sodium fluoride layer. Aluminum was deposited at about 80 nm. After vapor deposition, the light emitting element D1 was produced by sealing using a glass substrate.

(Evaluation)
EL light emission was observed by applying a voltage to the light emitting element D1. The driving voltage at 400 cd / m ² was 7.1 V, and the CIE chromaticity coordinates (x, y) were (0.14, 0.12). The drive voltage at 5000 cd / m ² was 10.5 V, and the CIE chromaticity coordinates (x, y) were (0.14, 0.12).

<Example D2> Production and Evaluation of Light-Emitting Element D2 In place of polymer compound PVK and compound EM1 (polymer compound PVK / compound EM1 = 90% by weight / 10% by weight) in Example D1, polymer compound PVK and A light emitting device D2 was produced in the same manner as in Example D1, except that the compound EM2 (polymer compound PVK / compound EM2 = 90% by weight / 10% by weight) was used.

(Evaluation)
EL light emission was observed by applying a voltage to the light emitting element D2. The driving voltage at 400 cd / m ² was 6.5 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.14). The drive voltage at 5000 cd / m ² was 9.8 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.13).

<Example D3> Production and Evaluation of Light-Emitting Element D3 In Example D1 (formation of hole transport layer), “polymer compound HTL-1 was dissolved in xylene at a concentration of 0.6% by weight. Using the obtained xylene solution, a film having a thickness of 20 nm is formed on the hole injection layer by spin coating, and heated by heating at 180 ° C. for 60 minutes in a nitrogen gas atmosphere on a hot plate. Instead of “a layer was formed”, “the polymer compound HTL-1 was dissolved in chlorobenzene at a concentration of 0.6% by weight. Using the obtained chlorobenzene solution, spin was formed on the hole injection layer. A hole transport layer was formed by forming a film with a thickness of 20 nm by a coating method and heating on a hot plate at 180 ° C. for 60 minutes in a nitrogen gas atmosphere. ” In the formation of the layer, “polymer compound PVK and compound EM1 (polymer compound PVK / compound EM1 = 90 wt% / 10 wt%) were dissolved in chlorobenzene at a concentration of 1.3 wt%. Instead of using a chlorobenzene solution, a film having a thickness of 60 nm was formed on the hole transport layer by a spin coat method and heated at 150 ° C. for 10 minutes in a nitrogen gas atmosphere to form a light emitting layer. Thus, “polymer compound HP-1 and compound EM1 (polymer compound HP-1 / compound EM1 = 90 wt% / 10 wt%) were dissolved in chlorobenzene at a concentration of 0.8 wt%. Using a chlorobenzene solution, a film having a thickness of 60 nm is formed on the hole transport layer by spin coating, and heated at 130 ° C. for 10 minutes in a nitrogen gas atmosphere. A light emitting element D3 was produced in the same manner as in Example D1, except that a light emitting layer was further formed.

(Evaluation)
EL light emission was observed by applying a voltage to the light emitting element D3. The driving voltage at 400 cd / m ² was 5.1 V, and the CIE chromaticity coordinates (x, y) were (0.14, 0.14). The drive voltage at 5000 cd / m ² was 8.0 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.14).

<Example D4> Production and Evaluation of Light-Emitting Element D4 In place of polymer compound HP-1 and compound EM1 (polymer compound HP-1 / compound EM1 = 90% by weight / 10% by weight) in Example D3, high A light emitting device D4 was produced in the same manner as in Example D3, except that the molecular compound HP-1 and the compound EM2 (polymer compound HP-1 / compound EM2 = 90 wt% / 10 wt%) were used.

(Evaluation)
EL light emission was observed by applying a voltage to the light emitting element D4. The driving voltage at 400 cd / m ² was 5.3 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.14). The drive voltage at 5000 cd / m ² was 8.6 V, and the CIE chromaticity coordinates (x, y) were (0.15, 0.14).

<Comparative Example CD1> Fabrication and Evaluation of Light-Emitting Element CD1 In Example D1, “1.3 weight of polymer compound PVK and compound EM1 (polymer compound PVK / compound EM1 = 90 wt% / 10 wt%) was added to chlorobenzene. In place of “polymer compound PVK and compound EM3 synthesized according to the method described in JP-A-2006-199698 (polymer compound PVK / compound EM3 = 90”). (Wt% / 10 wt%) was dissolved at a concentration of 0.8 wt%. A light emitting device CD1 was fabricated in the same manner as in Example D1, except that the solution was dissolved.

(Evaluation)
EL light emission was observed by applying a voltage to the light emitting device CD1. The driving voltage at 400 cd / m ² was 7.8 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.17). The drive voltage at 5000 cd / m ² was 12.0 V, and the CIE chromaticity coordinates (x, y) were (0.17, 0.17).

Claims (8)

The compound represented by Formula (1).

[Where:
R ¹ and R ² each independently represent a group represented by the formula (DA), a group represented by the formula (D-B), or a group represented by the formula (D-C).
n ¹ represents an integer of 3 or more and 7 or less .
L ¹ represents a single binding.
Ar ¹ is to display the group represented by the formula (1-A) group or the formula (1-B) represented by. A plurality of Ar ¹ may be the same or different. However, at least one Ar ¹ is a group represented by the formula (1-A), and at least one Ar ¹ is a group represented by the formula (1-B). ]

[Where:
m ^DA1 , m ^DA2 and m ^DA3 each independently represent an integer of 0 or more.
G ^DA is a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, these groups may have a substituent.
Ar ^DA1 , Ar ^DA2 and Ar ^DA3 each independently represent an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^DA1 , Ar ^DA2 and Ar ^DA3 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

[Where:
m ^DA1 , m ^DA2 , m ^DA3 , m ^DA4 , m ^DA5 , m ^DA6 and m ^DA7 each independently represent an integer of 0 or more.
G ^DA is a nitrogen atom, an aromatic hydrocarbon group or a heterocyclic group, these groups may have a substituent. A plurality of ^GDAs may be the same or different.
Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 each independently represent an arylene group or a divalent heterocyclic group, and these groups may have a substituent. Good. When there are a plurality of Ar ^DA1 , Ar ^DA2 , Ar ^DA3 , Ar ^DA4 , Ar ^DA5 , Ar ^DA6 and Ar ^DA7 , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. The plurality of ^TDAs may be the same or different. ]

[Where:
m ^DA1 represents an integer of 0 or more.
Ar ^DA1 represents an arylene group or a divalent heterocyclic group, and these groups optionally have a substituent. When there are a plurality of Ar ^{DA1 s} , they may be the same or different.
T ^DA represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]

[Where:
^{R 1A, R 2A, R 3A} , R 4A, R 5A, R 6A, R 7A and R ^8A each independently represent a water atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, an aryl group, An aryloxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent. However, R ^2A is binding hand, and, R ^7A is binding hand.
R ^1A and R ^2A , R ^2A and R ^3A , R ^3A and R ^4A , R ^4A and R ^5A , R ^5A and R ^6A , R ^6A and R ^7A , and R ^7A and R ^8A are bonded to each other, You may form the ring with the carbon atom to which each couple | bonds.
R ^91A represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom, and these groups optionally have a substituent.
R ^92A represents an aryl group or a monovalent heterocyclic group, and these groups optionally have a substituent. ]

[Where:
Z ^B represents a sulfur atom or an oxygen atom.
R ^1B , R ^2B , R ^3B , R ^4B , R ^5B , R ^6B , R ^7B and R ^8B are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkoxy group, cycloalkoxy group, aryl group, aryl An oxy group, a monovalent heterocyclic group, a substituted amino group, or a halogen atom is represented, and these groups may have a substituent. However R ^3B is binding hand, and, R ^6B is binding hand.
R ^9B is represented by a group represented by the formula (D-A1), a group represented by the formula (D-B1), a group represented by the formula (D-C1), or a formula (D-C2). A group represented by formula (D-C3) or a group represented by formula (D-C4).
R ^1B and R ^2B , R ^2B and R ^3B , R ^3B and R ^4B , R ^4B and R ^ZB , R ^ZB and R ^B5 , R ^5B and R ^6B , R ^6B and R ^7B , R ^7B and R ^8B , R ^8B And R ^9B , R ^1B and R ^9B may be bonded to each other to form a ring together with the carbon atoms to which they are bonded. ]

[Where:
R ^p1 and R ^p2 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, and np2 represents an integer of 0 to 3. A plurality of np1 may be the same or different. ]

[Where:
R ^p1 and R ^p2 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group, or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, and np2 represents an integer of 0 to 3. A plurality of np1 may be the same or different. ]

[Where:
R ^p4 and R ^p5 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p4 and R ^p5 , they may be the same or different.
np4 represents an integer of 0 to 5, and np5 represents an integer of 0 to 4. ] R ^91A is, have an alkyl group or a substituted group which may have a substituent is also optionally cycloalkyl group, claim 1 Symbol placement compound. The compound according to claim 1 or 2 , wherein R ^92A is an aryl group which may have a substituent. The group represented by the formula (DA) is a group represented by the formula (D-A1), a group represented by the formula (D-A2), or a group represented by (D-A3). The compound according to any one of claims 1 to 3 .

[Where:
R ^p1 , R ^p2 and R ^p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 may be the same or different. ] The group represented by the formula (D-B) is a group represented by the formula (D-B1), a group represented by the formula (D-B2), or a group represented by (D-B3). The compound according to any one of claims 1 to 3 .

[Where:
R ^p1 , R ^p2 and R ^p3 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When a plurality of R ^p1 and R ^p2 are present, they may be the same or different.
np1 represents an integer of 0 to 5, np2 represents an integer of 0 to 3, and np3 represents 0 or 1. A plurality of np1 may be the same or different. ] The group represented by the formula (D-C) is a group represented by the formula (D-C1), a group represented by the formula (D-C2), a group represented by the formula (D-C3) or a formula The compound according to any one of claims 1 to 3 , which is a group represented by (D-C4).

[Where:
R ^p4 and R ^p5 each independently represents an alkyl group, a cycloalkyl group, an alkoxy group, a cycloalkoxy group or a halogen atom. When there are a plurality of R ^p4 and R ^p5 , they may be the same or different.
np4 represents an integer of 0 to 5, and np5 represents an integer of 0 to 4. ] A compound according to any one of claims 1 to 6 ;
A composition containing at least one selected from the group consisting of a hole transport material, a hole injection material, an electron transport material, an electron injection material, a light emitting material, an antioxidant, and a solvent. The light emitting element containing the compound as described in any one of Claims 1-6 .