JP2007291092A - New bipyridine derivative and organic electroluminescence element containing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an electron transport material contributing to extension of the life of an organic electroluminescence element, and to provide an electroluminescence element utilizing the electron transport material. <P>SOLUTION: The invention relates to the compound represented by formula (1), and to the organic EL element using the compound. In the formula, G is a linking group with n valency excluding single bond, n is an integer of 2-4; R<SP>1</SP>-R<SP>4</SP>are each independently a H, a mono valent group or a free atomic valence linking to G, R<SP>5</SP>-R<SP>8</SP>are each independently a H or a mono valent group, one of R<SP>1</SP>-R<SP>4</SP>is a group with free atomic valence linking to G; and n 3, 2'-bipyridyl groups are the same or different. <P>COPYRIGHT: (C)2008,JPO&INPIT

Description

The present invention relates to a novel electron transport material having a 3,2′-bipyridyl group, and an organic electroluminescence device using the electron transport material (hereinafter sometimes abbreviated as an organic EL device or simply a device).

In recent years, active research has been conducted on organic EL elements as next-generation full-color flat panel displays, and they have already been put into practical use. In order to further promote the spread of organic EL elements, it is necessary to improve the driving characteristics of the elements, and in particular, blue elements that are currently delayed in driving voltage reduction and longer life compared to red and green elements. Improvement is an issue. In order to achieve these, new electron transport materials have been developed. As a document related to an electron transport material that has been reported so far, Patent Document 1 (Japanese Patent Laid-Open No. 2003-123983) discloses that an organic EL element is driven at a low voltage by using a phenanthroline derivative as an electron transport material. Furthermore, it is described that the 2,2′-bipyridyl compound, which is an analog of phenanthroline, can also be used as an electron transport material to drive an organic EL device at a low voltage. Has been. However, the element characteristics (driving voltage, luminous efficiency, etc.) reported in the examples of this document are only relative values based on comparative examples, and no actual measurement values that can be judged as practical values are described. . As another literature, examples using 2,2'-bipyridyl compound to the electron-transporting material, non-patent document ^{1 (: Proceedings of the 10 th} International Workshop on Inorganic and Organic Electroluminescence), Patent Document 2 (: JP 2002-158093) and Patent Document 3 (Japanese Patent Publication No. 11-514143). The 2,2′-bipyridyl compound described in Non-Patent Document 1 has a low glass transition temperature (Tg) and is not practical. The 2,2′-bipyridyl compound described in Patent Document 2 can drive an organic EL device at a relatively low voltage, but further reduction in voltage is desired for practical use. Patent Document 3 does not disclose a specific compound. As for the isomers of bipyridyl groups, reports on 2,2′-bipyridyl compounds have disclosed uses in a wide range of fields such as the above-mentioned literature, but the isomers of compounds having a 3,2′-bipyridyl group have been disclosed. There is no disclosure relating to synthesis, and no report has been made on the use of this compound as an organic EL device.
JP 2003-123983 A JP 2002-158093 A Japanese National Patent Publication No. 11-514143 Proceedings of the 10th International Workshop on Inorganic and Organic Electroluminescence

As described above, in the development of materials related to organic EL elements, particularly blue light-emitting organic EL elements, there is a strong demand for the appearance of electron transport materials that contribute to reducing the driving voltage, extending the life of the elements, and increasing the light emission efficiency. . An object of the present invention is to provide an electron transport material that contributes to extending the lifetime of an organic EL device, particularly a blue light emitting device. Furthermore, this invention makes it a subject to provide the organic EL element using this electron transport material.

As a result of intensive studies, the present inventors have developed a compound having a 3,2′-bipyridyl group and used it in an electron transport layer of an organic EL device, so that the luminance retention rate during constant current driving is high, that is, a long lifetime. The present invention was completed by finding that an organic EL device emitting blue light was obtained.
Said subject is solved by each item shown below.

式中、Ｇは単結合ではないｎ価の連結基であり、ｎは２〜４の整数であり；Ｒ^１〜Ｒ^４は独立して水素、１価の基またはＧに結合する遊離原子価であり、Ｒ^５〜Ｒ^８は独立して水素または１価の基であるが、Ｒ^１〜Ｒ^４の１つはＧに結合する遊離原子価であり；そして、ｎ個の３，２’−ビピリジル基は同一でもよく、異なっていてもよい。

［２］Ｒ^１〜Ｒ^４の１つがＧに結合する遊離原子価であり、それ以外が水素であり、Ｒ^５〜Ｒ⁸が水素である、前記［１］項に記載の化合物。
[1] A compound represented by the following formula (1).

Wherein G is an n-valent linking group that is not a single bond, n is an integer from 2 to 4; R ^{1 to} R ⁴ are independently hydrogen, a monovalent group, or a free valence bonded to G. R ^{5 to} R ⁸ are independently hydrogen or a monovalent group, but one of R ^{1 to} R ⁴ is the free valence bound to G; and n 3,2 ′ The -bipyridyl groups may be the same or different.

[2] The compound according to [1], wherein one of R ^{1 to} R ⁴ is a free valence bonded to G, the other is hydrogen, and R ^{5 to} R ⁸ are hydrogen.

式中、Ｇは下記の式（Ｇ１）〜（Ｇ３）で表される基の群から選択される１つであり；Ｒ^９〜Ｒ^１２の１つはＧに結合する遊離原子価であり、それ以外は水素であり；そして、Ｒ^１３〜Ｒ^１６の１つはＧに結合する遊離原子価であり、それ以外は水素である。

式中、Ｇ^１は独立して、下記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基である。

上記の式中、Ｒは独立して水素、炭素数１〜８のアルキル、炭素数３〜１０のシクロアルキル、または炭素数６〜２０のアリールであり；式（Ａ−１）〜（Ａ−２３）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物から誘導される２価の基は、遊離原子価を持つ原子以外の位置に置換基を有していてもよい。 [3] The compound according to item [2], represented by the following formula (2).

In the formula, G is one selected from the group of groups represented by the following formulas (G1) to (G3); one of R ^{9 to} R ¹² is a free valence bonded to G; The other is hydrogen; and one of R ¹³ -R ¹⁶ is the free valence bonded to G, the other is hydrogen.

Wherein, ^{G 1} is independently one selected from the group of compounds represented by the following formula (A-1) ~ (A -24) and formula (B-1) ~ (B -41) Is a divalent group derived from

In the above formula, R is independently hydrogen, alkyl having 1 to 8 carbons, cycloalkyl having 3 to 10 carbons, or aryl having 6 to 20 carbons; formulas (A-1) to (A- 23) and the divalent group derived from the compounds represented by formulas (B-1) to (B-41) may have a substituent at a position other than an atom having a free valence.

式中、Ｇの定義は式（２）におけるＧと同じである。

［５］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基である、前記［４］項に記載の化合物。

［６］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される２価の基である、前記［４］項に記載の化合物。

［７］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が下記の式（Ｃ−１）〜（Ｃ−１３）で表される２価の基の群から選択される１つである、前記［４］項に記載の化合物。

上記の式中、Ｒは独立して水素、メチル、エチル、へキシル、シクロヘキシル、メシチル、キシリル、フェニル、１−ナフチルまたは２−ナフチルであり；式（Ｃ−１）〜（Ｃ−１３）で表される２価の基は、遊離原子価をもつ原子以外の位置に置換基を有していてもよい。

［８］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［４］項に記載の化合物。

［９］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［４］項に記載の化合物。

［１０］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が下記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基である、前記［４］項に記載の化合物。

上記の式中、Ｒは独立して水素、メチル、エチル、へキシル、シクロヘキシル、メシチル、キシリル、フェニル、１−ナフチルまたは２−ナフチルであり；式（Ｃ−１）〜（Ｃ−７）で表される２価の基は、遊離原子価をもつ原子以外の位置に置換基を有していてもよい。

［１１］Ｇが下記の式（Ｇ３−１）〜（Ｇ３−３）のいずれか１つで表される連結基である、前記［４］項に記載の化合物。

式中、Ｇ^１Ａは独立して、前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基であり；Ｇ^１Ｂは独立して、前記の式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基である。

［１２］Ｇが式（Ｇ３−１）で表される連結基であり；Ｇ^１Ｂが下記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［１１］項に記載の化合物。

上記の式中、Ｒは水素、メチル、エチル、へキシル、シクロヘキシル、メシチル、キシリル、フェニル、１−ナフチルまたは２−ナフチルであり；式（Ｄ−１）〜（Ｄ−１５）で表される２価の基は、遊離原子価をもつ原子以外の位置に置換基を有していてもよい。

［１３］Ｇが式（Ｇ３−２）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基であり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される１つである、前記［１１］項に記載の化合物。

［１４］Ｇが式（Ｇ３−３）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−４）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［１１］項に記載の化合物。

［１５］Ｇが下記の式（Ｇ３−４）で表される連結基である、前記［１１］項に記載の化合物。

式中、Ｇ^１Ｂ１は前記の式（Ｄ−１）〜（Ｄ−９）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂ２は前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である。
[4] The compound according to [3], which is represented by the following formula (2-1).

In the formula, the definition of G is the same as G in Formula (2).

[5] G is a linking group represented by the formula (G1), selected from the group of the formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -24) The compound of the above-mentioned item [4], which is a divalent group derived from one of the above.

[6] G is a linking group represented by the formula (G1), selected from the group of the formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -16) The compound of the above-mentioned item [4], which is a divalent group derived from one of the above.

[7] is a linking group G is represented by the formula (G1), wherein (G1), 2-valent ^{to G 1} is represented by formula (C-1) ~ (C -13) below The compound according to item [4], which is one selected from the group of groups.

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-13) The divalent group represented may have a substituent at a position other than the atom having a free valence.

[8] is a linking group G is represented by the formula (G2), wherein (G2), ^{G 1} has the formula (A-1) ~ (A -24) and formula (B-1) ~ ( The compound according to item [4], which is the same divalent group derived from one selected from the group of compounds represented by B-41).

[9] G is a linking group represented by the formula (G2), selected from the group of the formula (G2) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -16) The compound of the above-mentioned item [4], which is the same divalent group derived from one of

[10] G is a linking group represented by the above formula (G2), and in formula (G2), G ¹ is a divalent group represented by the following formulas (C-1) to (C-7). The compound according to item [4], which is the same group selected from the group of groups.

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-7) The divalent group represented may have a substituent at a position other than the atom having a free valence.

[11] The compound according to [4] above, wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by the above formulas (A-1) to (A-24); G ^1B Is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41).

[12] G is a linking group represented by the formula (G3-1); G ^1B is selected from the group of divalent groups represented by the following formulas (D-1) to (D-15) The compound according to [11] above, which is the same group.

In the above formula, R is hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; represented by formulas (D-1) to (D-15) The divalent group may have a substituent at a position other than an atom having a free valence.

[13] G is a linking group represented by the formula (G3-2); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). The above-mentioned [11], wherein G ^1B is one selected from the group of divalent groups represented by the formulas (D-1) to (D-15). Compound.

[14] G is a linking group represented by the formula (G3-3); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-4). And G ^1B is the same group selected from the group of divalent groups represented by the above formulas (D-1) to (D-15). Compound.

[15] The compound according to [11], wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the formulas (D-1) to (D-9), and G ^1B2 is the formula (D-1). It is the same group selected from the group of the bivalent group represented by-(D-15).

式中、Ｇの定義は式（２）におけるＧと同じである。

［１７］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基である、前記［１６］項に記載の化合物。

［１８］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される２価の基である、前記［１６］項に記載の化合物。

［１９］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ｃ−１）〜（Ｃ−１３）で表される２価の基の群から選択される１つである、前記［１６］項に記載の化合物。

［２０］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［１６］項に記載の化合物。

［２１］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［１６］項に記載の化合物。

［２２］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基である、前記［１６］項に記載の化合物。

［２３］Ｇが下記の式（Ｇ３−１）〜（Ｇ３−３）のいずれか１つで表される連結基である、前記［１６］項に記載の化合物。

式中、Ｇ^１Ａは独立して、前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基であり；Ｇ^１Ｂは独立して、前記の式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基である。

［２４］Ｇが式（Ｇ３−１）で表される連結基であり；Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［２３］項に記載の化合物。

［２５］Ｇが式（Ｇ３−２）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基であり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される１つである、前記［２３］項に記載の化合物。

［２６］Ｇが式（Ｇ３−３）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［２３］項に記載の化合物。

［２７］Ｇが下記の式（Ｇ３−４）で表される連結基である、前記［２３］項に記載の化合物。

式中、Ｇ^１Ｂ１は前記の式（Ｄ−１）〜（Ｄ−９）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂ２は前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である。
[16] The compound according to [3], which is represented by the following formula (2-2).

In the formula, the definition of G is the same as G in Formula (2).

[17] G is a linking group represented by the formula (G1), and in the formula (G1), G ¹ is a group of compounds represented by the formulas (A-1) to (A-24). The compound according to [16] above, which is a divalent group derived from one selected from:

[18] G is a linking group represented by the formula (G1), a group of formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -16) The compound according to the above [16], which is a divalent group derived from one selected from:

[19] a linking group G is represented by the formula (G1), wherein (G1), 2-valent ^{to G 1} is represented by the formula (C-1) ~ (C -13) The compound according to item [16], which is one selected from the group of groups.

[20] G is a linking group represented by the formula (G2), the formula (G2) in, ^{G 1} is the formula (A-1) ~ (A -24) and formula (B-1) The compound according to [16] above, which is the same divalent group derived from one selected from the group of compounds represented by (B-41).

[21] G is a linking group represented by the formula (G2), a group of formula (G2) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -16) The compound according to [16] above, which is the same divalent group derived from one selected from:

[22] G is a linking group represented by the above formula (G2), and in formula (G2), G ¹ is a divalent group represented by the above formulas (C-1) to (C-7). The compound according to the above item [16], which is the same group selected from the group of groups.

[23] The compound according to [16], wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by the above formulas (A-1) to (A-24); G ^1B Is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41).

[24] G is a linking group represented by the formula (G3-1); G ^1B is selected from the group of divalent groups represented by the formulas (D-1) to (D-15). The compound according to [23] above, which is the same group.

[25] G is a linking group represented by the formula (G3-2); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). The same group, and G ^1B is one selected from the group of divalent groups represented by formulas (D-1) to (D-15) above, Compound.

[26] G is a linking group represented by the formula (G3-3); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). And G ^1B is the same group selected from the group of divalent groups represented by the formulas (D-1) to (D-15). Compound.

[27] The compound according to [23], wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the formulas (D-1) to (D-9), and G ^1B2 is the formula (D-1). It is the same group selected from the group of the bivalent group represented by-(D-15).

式中、Ｇの定義は式（２）におけるＧと同じである。

［２９］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基である、前記［２８］項に記載の化合物。

［３０］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される２価の基である、前記［２８］項に記載の化合物。

［３１］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ｃ−１）〜（Ｃ−１３）で表される２価の基の群から選択される１つである、前記［２８］項に記載の化合物。

［３２］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［２８］項に記載の化合物。

［３３］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［２８］項に記載の化合物。

［３４］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基である、前記［２８］項に記載の化合物。

［３５］Ｇが下記の式（Ｇ３−１）〜（Ｇ３−３）のいずれか１つで表される連結基である、前記［２８］項に記載の化合物。

式中、Ｇ^１Ａは独立して、前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基であり；Ｇ^１Ｂは独立して、前記の式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基である。

［３６］Ｇが式（Ｇ３−１）で表される連結基であり；Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［３５］項に記載の化合物。

［３７］Ｇが式（Ｇ３−２）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基であり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される１つである、前記［３５］項に記載の化合物。

［３８］Ｇが式（Ｇ３−３）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［３５］項に記載の化合物。

［３９］Ｇが下記の式（Ｇ３−４）で表される連結基である、前記［３５］項に記載の化合物。

式中、Ｇ^１Ｂ１は前記の式（Ｄ−１）〜（Ｄ−９）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂ２は前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である。
[28] The compound according to item [3], represented by the following formula (2-3).

In the formula, the definition of G is the same as G in Formula (2).

[29] G is a linking group represented by the formula (G1), a group of formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -24) The compound according to [28] above, which is a divalent group derived from one selected from:

[30] G is a linking group represented by the formula (G1), a group of formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -16) The compound according to item [28], which is a divalent group derived from one selected from:

[31] a linking group G is represented by the formula (G1), wherein (G1), 2-valent ^{to G 1} is represented by the formula (C-1) ~ (C -13) The compound according to item [28], which is one selected from the group of groups.

[32] G is a linking group represented by the formula (G2), the formula (G2) in, ^{G 1} is the formula (A-1) ~ (A -24) and formula (B-1) The compound according to [28] above, which is the same divalent group derived from one selected from the group of compounds represented by (B-41).

[33] G is a linking group represented by the formula (G2), and in the formula (G2), G ¹ is a group of compounds represented by the formulas (A-1) to (A-16). The compound according to item [28], which is the same divalent group derived from one selected from:

[34] G is a linking group represented by the above formula (G2), and in formula (G2), G ¹ is a divalent group represented by the above formulas (C-1) to (C-7). The compound according to item [28], which is the same group selected from the group of groups.

[35] The compound according to [28], wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by the above formulas (A-1) to (A-24); G ^1B Is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41).

[36] G is a linking group represented by the formula (G3-1); G ^1B is selected from the group of divalent groups represented by the formulas (D-1) to (D-15). The compound of the above-mentioned [35], which is the same group.

[37] G is a linking group represented by the formula (G3-2); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). The above-mentioned [35], wherein G ^1B is one selected from the group of divalent groups represented by the formulas (D-1) to (D-15). Compound.

[38] G is a linking group represented by the formula (G3-3); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). And G ^1B is the same group selected from the group of divalent groups represented by the above formulas (D-1) to (D-15). Compound.

[39] The compound according to [35], wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the formulas (D-1) to (D-9), and G ^1B2 is the formula (D-1). It is the same group selected from the group of the bivalent group represented by-(D-15).

式中、Ｇの定義は式（２）におけるＧと同じである。

［４１］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基である、前記［４０］項に記載の化合物。

［４２］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される２価の基である、前記［４０］項に記載の化合物。

［４３］Ｇが前記の式（Ｇ１）で表される連結基であり、式（Ｇ１）中、Ｇ^１が前記の式（Ｃ−１）〜（Ｃ−１３）で表される２価の基の群から選択される１つである、前記［４０］項に記載の化合物。

［４４］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［４０］項に記載の化合物。

［４５］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ａ−１）〜（Ａ−１６）で表される化合物の群から選択される１つから誘導される同一の２価の基である、前記［４０］項に記載の化合物。

［４６］Ｇが前記の式（Ｇ２）で表される連結基であり、式（Ｇ２）中、Ｇ^１が前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基である、前記［４０］項に記載の化合物。

［４７］Ｇが下記の式（Ｇ３−１）〜（Ｇ３−３）のいずれか１つで表される連結基である、前記［４０］項に記載の化合物。

式中、Ｇ^１Ａは独立して、前記の式（Ａ−１）〜（Ａ−２４）で表される化合物の群から選択される１つから誘導される２価の基であり；Ｇ^１Ｂは独立して、前記の式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基である。

［４８］Ｇが式（Ｇ３−１）で表される連結基であり；Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［４７］項に記載の化合物。

［４９］Ｇが式（Ｇ３−２）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される同一の基であり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される１つである、前記［４７］項に記載の化合物。

［５０］Ｇが式（Ｇ３−３）で表される連結基であり；Ｇ^１Ａが前記の式（Ｃ−１）〜（Ｃ−７）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂが前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である、前記［４７］項に記載の化合物。

［５１］Ｇが下記の式（Ｇ３−４）で表される連結基である、前記［４７］項に記載の化合物。

式中、Ｇ^１Ｂ１は前記の式（Ｄ−１）〜（Ｄ−９）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂ２は前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である。
[40] The compound according to item [3], represented by the following formula (2-4).

In the formula, the definition of G is the same as G in Formula (2).

[41] a linking group G is represented by the formula (G1), a group of formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -24) The compound of the above-mentioned [40], which is a divalent group derived from one selected from:

[42] G is a linking group represented by the formula (G1), a group of formula (G1) in the ^{compound G 1} is represented by the formula (A-1) ~ (A -16) The compound of the above-mentioned [40], which is a divalent group derived from one selected from:

[43] a linking group G is represented by the formula (G1), wherein (G1), 2-valent ^{to G 1} is represented by the formula (C-1) ~ (C -13) The compound according to item [40], which is one selected from the group of groups.

[44] G is the formula is a linking group represented by (G2), the formula (G2) in the formula of ^{G 1} is the (A-1) ~ (A -24) and formula (B-1) The compound according to the above [40], which is the same divalent group derived from one selected from the group of compounds represented by (B-41).

[45] G is a linking group represented by the formula (G2), and in the formula (G2), G ¹ is a group of compounds represented by the formulas (A-1) to (A-16). The compound according to the above [40], which is the same divalent group derived from one selected from:

[46] G is a linking group represented by the above formula (G2), and in formula (G2), G ¹ is a divalent group represented by the above formulas (C-1) to (C-7). The compound according to the above [40], which is the same group selected from the group of groups.

[47] The compound according to [40], wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by the above formulas (A-1) to (A-24); G ^1B Is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41).

[48] G is a linking group represented by the formula (G3-1); G ^1B is selected from the group of divalent groups represented by the formulas (D-1) to (D-15). The compound of the above-mentioned [47], which is the same group.

[49] G is a linking group represented by the formula (G3-2); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). The above-mentioned [47] item, wherein G ^1B is one selected from the group of divalent groups represented by the formulas (D-1) to (D-15). Compound.

[50] G is a linking group represented by the formula (G3-3); G ^1A is selected from the group of divalent groups represented by the formulas (C-1) to (C-7). And G ^1B is the same group selected from the group of divalent groups represented by the formulas (D-1) to (D-15) above, Compound.

[51] The compound according to [47], wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the formulas (D-1) to (D-9), and G ^1B2 is the formula (D-1). It is the same group selected from the group of the bivalent group represented by-(D-15).

式中、Ｇは下記の式（Ｇ４）または（Ｇ５）で表される基であり；Ｒ^１７〜Ｒ^２０の１つはＧに結合する遊離原子価であり、それ以外は水素であり；Ｒ^２１〜Ｒ^２４の１つはＧに結合する遊離原子価であり、それ以外は水素であり；Ｒ^２５〜Ｒ^２８の１つはＧに結合する遊離原子価であり、それ以外は水素である。

式中、Ｇ^１は独立して、前記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基であり；Ｇ^２Ａは、下記の式（Ｅ−１）〜（Ｅ−９）で表される３価の基の群から選択される１つであり、Ｇ^２Ｂはホウ素、窒素、ホスホリル基、または式（Ｅ−１）〜（Ｅ−９）で表される３価の基の群から選択される１つである。

［５３］Ｇが式（Ｇ５）で表される連結基であり、式（Ｇ５）においてＧ^１が同一である前記［３２］項に記載の化合物。
[52] The compound according to item [2], which is represented by the following formula (3).

In the formula, G is a group represented by the following formula (G4) or (G5); one of R ^{17 to} R ²⁰ is a free valence bonded to G, and the other is hydrogen; ^{One of 21 to} R ²⁴ is a free valence bonded to G and the other is hydrogen; one of R ^{25 to} R ²⁸ is a free valence bonded to G and the other is hydrogen .

In the formula, G ¹ is independently one selected from the group of compounds represented by formulas (A-1) to (A-24) and formulas (B-1) to (B-41). G ^2A is one selected from the group of trivalent groups represented by the following formulas (E-1) to (E-9), and G ^2B Is one selected from the group of boron, nitrogen, phosphoryl groups, or trivalent groups represented by formulas (E-1) to (E-9).

[53] The compound according to [32], wherein G is a linking group represented by formula (G5), and G ¹ is the same in formula (G5).

式中、Ｇは下記の式（Ｇ６）または（Ｇ７）で表される基であり；Ｒ^２９〜Ｒ^３２の１つはＧに結合する遊離原子価であり、それ以外は水素であり；Ｒ^３３〜Ｒ^３６の１つはＧに結合する遊離原子価であり、それ以外は水素であり；Ｒ^３７〜Ｒ^４０の１つはＧに結合する遊離原子価であり、それ以外は水素であり；Ｒ^４１〜Ｒ^４４の１つはＧに結合する遊離原子価であり、それ以外は水素である。

式中、Ｇ^１は独立して、前記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基であり；Ｇ^３Ａは、下記の式（Ｆ−１）〜（Ｆ−８）で表される４価の基の群から選択される１つであり；Ｇ^３Ｂは炭素、ケイ素、または式（Ｆ−１）〜（Ｆ−８）で表される４価の基の群から選択される１つである。

［５５］Ｇが式（Ｇ７）で表される連結基であり、式（Ｇ７）においてＧ^１が同一である、前記［３４］項に記載の化合物。

［５６］Ｇ^１が式（Ｃ−１）で表される２価の基である、前記［７］項に記載の化合物。

［５７］Ｇ^１が１,１−ジメチル−３，４−ジメシチルシロール−２，５−ジイルである、前記［７］項に記載の化合物。

［５８］Ｇ^１が式（Ｃ−２）で表される２価の基である、前記［７］項に記載の化合物。

［５９］Ｇ^１がアントラセン−９，１０−ジイルである、前記［７］項に記載の化合物。
[54] The compound according to item [2], which is represented by the following formula (4).

In the formula, G is a group represented by the following formula (G6) or (G7); one of R ^{29 to} R ³² is a free valence bonded to G, and the other is hydrogen; ^{One of 33 to} R ³⁶ is a free valence bonded to G and the other is hydrogen; one of R ^{37 to} R ⁴⁰ is a free valence bonded to G and the other is hydrogen One of R ^{41 to} R ⁴⁴ is a free valence bonded to G, and the other is hydrogen.

In the formula, G ¹ is independently one selected from the group of compounds represented by formulas (A-1) to (A-24) and formulas (B-1) to (B-41). G ^3A is one selected from the group of tetravalent groups represented by the following formulas (F-1) to (F-8); G ^3B Is one selected from carbon, silicon, or a group of tetravalent groups represented by formulas (F-1) to (F-8).

[55] The compound according to [34], wherein G is a linking group represented by formula (G7), and G ¹ is the same in formula (G7).

[56] The compound according to [7], wherein G ¹ is a divalent group represented by formula (C-1).

[57] The compound according to [7], wherein G ¹ is 1,1-dimethyl-3,4-dimesitylsilol-2,5-diyl.

[58] The compound according to [7], wherein G ¹ is a divalent group represented by formula (C-2).

[59] The compound according to [7] above, wherein G ¹ is anthracene-9,10-diyl.

[60] An organic electroluminescent device comprising the compound according to any one of [1] to [59].
[61] In an organic electroluminescent device sandwiched between an anode and a cathode and having at least a hole transport layer, a light emitting layer, and an electron transport layer on a substrate, the electron transport layer includes the items [1] to [59]. Organic electroluminescent element containing the compound of any one of these.

The compound of the present invention is stable even when a voltage is applied in a thin film state, and can provide an organic EL device having a high charge transport capability. The compound according to a preferred embodiment of the present invention is suitable as a charge transport material in an organic EL device. By using the compound according to a preferred embodiment of the present invention for the electron transport layer of an organic EL device, a long-life organic EL device can be obtained. Since the compound according to the preferred embodiment of the present invention can realize a long lifetime of the blue light emitting element in particular, a high-performance display device such as a full color display can be produced by using the organic EL element of the present invention.

式中、Ｇは単結合ではないｎ価の連結基である。ｎ価の連結基とはｎ価の原子、ｎ価の基およびｎ個の遊離原子価をもつ環系を指す総称であり、かつ、ｎ価の連結基はこれらを組み合わせて構成されてもよい。ｎ価の連結基が非対称な構造である場合も、ｎ個の３，２’−ビピリジル基は該連結基の任意の位置に結合してよい。ｎ価の連結基Ｇについての詳しい説明は後述する。ｎは２〜４の整数である。 Hereinafter, the present invention will be described in more detail.
<Description of compound>
The first invention of the present application is a compound having a 3,2′-bipyridyl group represented by the following formula (1). Hereinafter, in the present specification, “compound represented by formula (1)” and “compound represented by formula (2)” are expressed as “compound (1)” and “compound (2)”. There is. Similarly, “compound represented by the formula (2-1-1)”, “compound represented by the formula (2-1-2)”, etc. are referred to as “compound (2-1-1)”, “compound ( 2-1-2) "or the like. In the chemical formula, Me represents methyl, t-Bu represents t-butyl, and Ph represents phenyl.

In the formula, G is an n-valent linking group that is not a single bond. An n-valent linking group is a generic term that refers to a ring system having an n-valent atom, an n-valent group, and n free valences, and the n-valent linking group may be formed by combining them. . Even when the n-valent linking group has an asymmetric structure, n 3,2′-bipyridyl groups may be bonded to any position of the linking group. Detailed description of the n-valent linking group G will be described later. n is an integer of 2-4.

In the present specification, a group formed by R ^{1 to} R ⁸ and a 3,2′-bipyridyl nucleus is referred to as a 3,2′-bipyridyl group. One of R ^{1 to} R ⁴ in the 3,2′-bipyridyl group is a free valence bonded to G, and the others are independently hydrogen or a monovalent group. R ^{5 to} R ⁸ are independently hydrogen or a monovalent group. The n 3,2′-bipyridyl groups may be the same or different. The notation “n free valences” in the linking group G and “free valence bonded to G” in the 3,2′-bipyridyl group indicate that G and 3,2′-bipyridyl group are free. It does not represent the presence of a group (radical). “Free valence” refers to a so-called “bond” that is bonded to another group or atom by a covalent bond. That is, the expression “ ^one of R ^{1 to} R ⁴ in the 3,2′-bipyridyl group is a free valence bonded to G” is any of R ^{1 to} R ⁴ in the 3,2′-bipyridyl group. 1 represents a state in which one is bonded to an atom having a free valence of the linking group G.

The monovalent group in R ^{1 to} R ⁸ is a nitro group, a cyano group, a dimesitylboryl group, an aryl having 6 to 12 carbon atoms, or an alkyl having 1 to 12 carbon atoms. The alkyl may be linear, branched or cyclic. Specific examples of the monovalent group are phenyl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, 2-naphthyl, methyl, t-butyl, and cyclohexyl. R ^{5 to} R ⁸ are preferably hydrogen.

In the 3,2′-bipyridyl group, R ¹ , R ² or R ³ is preferably bonded to G. R ^{1 to} R ^{4 that} are not involved in bonding with G are preferably hydrogen.

In formula (1), n is most preferably 2, then 3 is preferred, and then 4 is preferred. One reason is that the compound is easy to produce. Secondly, it is considered that the molecular weight does not become extremely large and the sublimation property is relatively improved, and an advantage that it is easy to form a film at the time of manufacturing the organic EL element can be expected.

Ｒ^９〜Ｒ^１２の１つはＧに結合する遊離原子価であり、それ以外は水素である。ここで、Ｒ¹⁰、Ｒ^１1またはＲ^１2がＧに結合することが好ましい。Ｒ^１３〜Ｒ^１６の１つはＧに結合する遊離原子価であり、それ以外は水素である。ここで、Ｒ^１4、Ｒ^１5またはＲ^１6がＧに結合することが好ましい。２つの３，２’−ビピリジル基は同一でもよく、異なっていてもよい。 <Compound with n = 2>
The compound in which n is 2 is specifically represented by the following formula (2).

One of R ^{9 to} R ¹² is a free valence bonded to G, and the other is hydrogen. Here, R ¹⁰ , R ¹¹ or R ¹² is preferably bonded to G. One of R ^{13 to} R ¹⁶ is a free valence bonded to G, and the other is hydrogen. Here, it is preferable that R ¹⁴ , R ¹⁵ or R ¹⁶ is bonded to G. The two 3,2′-bipyridyl groups may be the same or different.

Ｇ^１は独立して、下記の式（Ａ−１）〜（Ａ−２４）および式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群から選択される１つから誘導される２価の基である。以降、式（Ａ−１）〜（Ａ−２４）で表される化合物の群をＡ群、式（Ｂ−１）〜（Ｂ−４１）で表される化合物の群をＢ群と称することがある。 G is one selected from the group of linking groups represented by the following formulas (G1) to (G3). In formulas (G2) and (G3), G ¹ may be the same or different.

G ¹ is independently derived from one selected from the group of compounds represented by the following formulas (A-1) to (A-24) and formulas (B-1) to (B-41): A divalent group. Hereinafter, a group of compounds represented by formulas (A-1) to (A-24) is referred to as Group A, and a group of compounds represented by Formulas (B-1) to (B-41) is referred to as Group B. There is.

In the above formulas (A-1) to (A-21) and (B-1) to (B-40), R is independently hydrogen, alkyl having 1 to 8 carbons, or cyclohexane having 3 to 10 carbons. Alkyl or aryl having 6 to 20 carbon atoms. Alkyl may be linear or branched, and examples thereof include linear alkyl having 1 to 8 carbon atoms and branched alkyl having 3 to 8 carbon atoms. Examples of linear alkyl having 1 to 8 carbon atoms are methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl and n-octyl. Examples of branched alkyl having 3 to 8 carbon atoms are isopropyl, isobutyl, s-butyl, t-butyl, isopentyl, neopentyl, t-pentyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethyl. Butyl, 2-ethylbutyl, 1-methylhexyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl and the like. Examples of cycloalkyl having 3 to 10 carbon atoms are cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl and the like. Examples of aryl having 6 to 20 carbon atoms include phenyl, tolyl, xylyl, biphenylyl, naphthyl, anthracenyl, phenanthryl, terphenylyl, fluorenyl, pyrenyl and the like. Preferred R is hydrogen, methyl, ethyl, hexyl, cyclohexyl, phenyl, 1-naphthyl, and 2-naphthyl. Among these, phenyl, 1-naphthyl and 2-naphthyl may have a substituent. Specific examples of substituents are methyl, ethyl, hexyl, cyclohexyl, and phenyl, with methyl being preferred.

The divalent group derived from the compounds represented by formulas (A-1) to (A-24) and formulas (B-1) to (B-41) is located at a position other than an atom having a free valence. It may have a substituent. Specific examples of the substituent are methyl, ethyl, t-butyl, hexyl, cyclohexyl, phenyl, xylyl, mesityl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, and 2-naphthyl.

Ｒ^１７〜Ｒ^２０の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^１８、Ｒ^１９またはＲ^２０がＧに結合することが好ましい。Ｒ^２１〜Ｒ^２４の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^２２、Ｒ^２３またはＲ^２４がＧに結合することが好ましい。Ｒ^２５〜Ｒ^２８の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^２６、Ｒ^２７またはＲ^２８がＧに結合することが好ましい。３つの３，２’−ビピリジル基は同一でもよく、異なっていてもよい。 <Compound with n = 3>
The compound in which n is 3 is specifically represented by the following formula (3).

One of R ^{17 to} R ²⁰ is a free valence linked to G, and the other is hydrogen. Here, it is preferable that R ¹⁸ , R ¹⁹ or R ²⁰ is bonded to G. One of R ^{21 to} R ²⁴ is a free valence linked to G, and the other is hydrogen. Here, R ²² , R ²³ or R ²⁴ is preferably bonded to G. One of R ^{25 to} R ²⁸ is the free valence linked to G, the other is hydrogen. Here, it is preferable that R ²⁶ , R ²⁷ or R ²⁸ is bonded to G. The three 3,2′-bipyridyl groups may be the same or different.

Ｇ^１は独立して、前記のＡ群およびＢ群の化合物から選択される１つから誘導される２価の基である。 G is a linking group represented by the following formula (G4) or (G5). In formula (G5), G ¹ may be the same or different.

G ¹ is independently a divalent group derived from one selected from the group A and B compounds.

G ^2A is one selected from the group of trivalent groups represented by the following formulas (E-1) to (E-9), and G ^2B is boron, nitrogen, phosphoryl group, or the formula ( It is one selected from the group of trivalent groups represented by E-1) to (E-9).

Ｒ^２９〜Ｒ^３２の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^３０、Ｒ^３１またはＲ^３２がＧに結合することが好ましい。Ｒ^３３〜Ｒ^３６の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^３４、Ｒ^３５またはＲ^３６がＧに結合することが好ましい。Ｒ^３７〜Ｒ^４０の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^３８、Ｒ^３９またはＲ^４０がＧに結合することが好ましい。Ｒ^４１〜Ｒ^４４の１つはＧに連結する遊離原子価であり、それ以外は水素である。ここで、Ｒ^４２、Ｒ^４３またはＲ^４４がＧに結合することが好ましい。４つの３，２’−ビピリジル基は同一でもよく、異なっていてもよい。 <Compound with n = 4>
The compound in which n is 4 is specifically represented by the following formula (4).

One of R ^{29 to} R ³² is a free valence linked to G, and the other is hydrogen. Here, R ³⁰ , R ³¹ or R ³² is preferably bonded to G. One of R ^{33 to} R ³⁶ is a free valence linked to G, and the other is hydrogen. Here, it is preferable that R ³⁴ , R ³⁵ or R ³⁶ is bonded to G. One of R ^{37 to} R ⁴⁰ is a free valence linked to G, and the other is hydrogen. Here, R ³⁸ , R ³⁹ or R ⁴⁰ is preferably bonded to G. One of R ^{41 to} R ⁴⁴ is a free valence linked to G, and the other is hydrogen. Here, R ⁴² , R ⁴³ or R ⁴⁴ is preferably bonded to G. The four 3,2′-bipyridyl groups may be the same or different.

Ｇ^１は独立して、前記のＡ群およびＢ群の化合物から選択される１つから誘導される２価の基である。 G is a linking group represented by the following formula (G6) or (G7). In formula (G7), G ¹ may be the same or different.

G ¹ is independently a divalent group derived from one selected from the group A and B compounds.

G ^3A is one selected from the group of tetravalent groups represented by the following formulas (F-1) to (F-8), and G ^3B is carbon, silicon, or the formula (F-1). ) To (F-8), one selected from the group of tetravalent groups.

式（２−１）〜（２−４）においては、式（２−１）〜（２−２）が好ましく、次いで式（２−３）が好ましく、次いで式（２−４）が好ましい。式（２−１）〜（２−４）においては、Ｇは式（Ｇ１）であることが好ましく、次いで式（Ｇ３）であることが好ましく、次いで式（Ｇ２）であることが好ましい。 <More detailed description of the compound where n = 2>
Preferred compounds wherein n is 2 are represented by the following formulas (2-1) to (2-4).

In Formulas (2-1) to (2-4), Formulas (2-1) to (2-2) are preferable, then Formula (2-3) is preferable, and then Formula (2-4) is preferable. In the formulas (2-1) to (2-4), G is preferably the formula (G1), then preferably the formula (G3), and then preferably the formula (G2).

Ｒは独立して水素、メチル、エチル、へキシル、シクロヘキシル、メシチル、キシリル、フェニル、１−ナフチルまたは２−ナフチルである。式（Ｃ−１）〜（Ｃ−１３）で表される２価の基は、遊離原子価をもつ原子以外の位置に置換基を有していてもよい。置換基の具体例はメチル、エチル、ｔ−ブチル、へキシル、シクロヘキシル、フェニル、キシリル、メシチル、２−ビフェニリル、３−ビフェニリル、４−ビフェニリル、１−ナフチル、および２−ナフチルである。 When G in Formulas (2-1) to (2-4) is Formula (G1), G ¹ is a divalent group derived from one selected from the group A compounds described above. Preferably, among the group A, a divalent group derived from one selected from the group of compounds represented by formulas (A-1) to (A-16) is more preferable. More preferably, it is one selected from the group of divalent groups represented by C-1) to (C-13).

R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl. The divalent groups represented by formulas (C-1) to (C-13) may have a substituent at a position other than an atom having a free valence. Specific examples of the substituent are methyl, ethyl, t-butyl, hexyl, cyclohexyl, phenyl, xylyl, mesityl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, and 2-naphthyl.

In the formulas (2-1) to (2-4), when G is the formula (G2), G ¹ is the same divalent derivative derived from one selected from the group A and group B compounds. Are preferably the same divalent group derived from one selected from the group of compounds represented by formulas (A-1) to (A-11), More preferably, they are the same group selected from the group of divalent groups represented by the above formulas (C-1) to (C-13).

Ｇ^１Ａは独立して、前記のＡ群の化合物から選択される１つから誘導される２価の基であり、Ｇ^１Ｂは独立して、前記のＢ群の化合物から選択される１つから誘導される２価の基である。 In the formulas (2-1) to (2-4), when G is the formula (G3), it is more specifically represented by any one of the following formulas (G3-1) to (G3-3). A linking group is preferred.

G ^1A is independently a divalent group derived from one selected from the group A compounds, and G ^1B is independently from one selected from the group B compounds. A divalent group to be derived.

Ｒは水素、メチル、エチル、へキシル、シクロヘキシル、フェニル、１−ナフチルまたは２−ナフチルである。式（Ｄ−１）〜（Ｄ−１５）で表される２価の基は、遊離原子価をもつ原子以外の位置に置換基を有していてもよい。置換基の具体例はメチル、エチル、ｔ−ブチル、へキシル、シクロヘキシル、フェニル、キシリル、メシチル、２−ビフェニリル、３−ビフェニリル、４−ビフェニリル、１−ナフチル、および２−ナフチルである。 In Formulas (2-1) to (2-4), when G is a linking group represented by Formula (G3-1), G ^1B is represented by Formulas (D-1) to (D-15) below. It is preferably the same group selected from the group of divalent groups represented.

R is hydrogen, methyl, ethyl, hexyl, cyclohexyl, phenyl, 1-naphthyl or 2-naphthyl. The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence. Specific examples of the substituent are methyl, ethyl, t-butyl, hexyl, cyclohexyl, phenyl, xylyl, mesityl, 2-biphenylyl, 3-biphenylyl, 4-biphenylyl, 1-naphthyl, and 2-naphthyl.

In Formulas (2-1) to (2-4), when G is a linking group represented by Formula (G3-2), G ^1A is represented by Formulas (C-1) to (C-7). And G ^1B is selected from the group of divalent groups represented by the above formulas (D-1) to (D-15). One is preferred.

In Formulas (2-1) to (2-4), when G is a linking group represented by Formula (G3-3), G ^1A is represented by Formulas (C-1) to (C-7). And G ^1B is the same selected from the group of divalent groups represented by the above formulas (D-1) to (D-15). The group is preferably.

Ｇ^１Ｂ１は前記の式（Ｄ−１）〜（Ｄ−９）で表される２価の基の群から選択される１つであり、Ｇ^１Ｂ２は前記の式（Ｄ−１）〜（Ｄ−１５）で表される２価の基の群から選択される同一の基である。 In Formulas (2-1) to (2-4), when G is a linking group represented by Formula (G3-1), G is more specifically a linking group represented by Formula (G3-4). More preferably.

G ^1B1 is one selected from the group of divalent groups represented by the formulas (D-1) to (D-9), and G ^1B2 is the formula (D-1) to (D -15) is the same group selected from the group of divalent groups represented by

<Specific examples of compounds>
Specific examples of the compounds of the present invention are shown by the formulas listed below, but the present invention is not limited by the disclosure of these specific structures.

<Specific Example of Compound Represented by Formula (2-1)>
Specific examples of the compound represented by the formula (2-1) are represented by the following formulas (2-1-1) to (2-1-44). Among these, preferred compounds are formulas (2-1-1) to (2-1-30). Further preferred compounds are formulas (2-1-1) to (2-1-8).

<Specific Example of Compound Represented by Formula (2-2)>
Specific examples of the compound represented by the formula (2-2) are represented by the following formulas (2-2-1) to (2-229). Among these, preferred compounds are the formulas (2-2-1) to (2-2-12) and (2-226) to (2-229). More preferred compounds are formulas (2-2-1) to (2-2-4).

<Specific Example of Compound Represented by Formula (2-3)>
Specific examples of the compound represented by the formula (2-3) are represented by the following formulas (2-3-1) to (2-3-6).

<Specific Example of Compound Represented by Formula (2-4)>
Specific examples of the compound represented by the formula (2-4) are represented by the following formulas (2-4-1) to (2-4-6).

<Specific Example of Compound Represented by Formula (3)>
Specific examples of the compound represented by the formula (3) are represented by the following formulas (3-1) to (3-5).

Specific examples of the compound represented by the formula (4) are represented by the following formulas (4-1) to (4-4).

<Method of synthesizing compounds>
As a method of synthesizing a bipyridine derivative substituted with a halogen such as bromine, various coupling reactions such as a Suzuki coupling reaction, a Negishi coupling reaction, a reaction with a Grignard reagent, etc. are used using dibromopyridine and bromopyridine as raw materials. Can do. In addition, the reaction of lithiopyridine and 2-pyridyl sulfoxide (J. Org. Chem., 58 , 4382 (1993)) can also be applied (Scheme 1).

In the first step reaction of Scheme 1, 2,5-dibromopyridine is lithiated, but the 5-position out of two Br must be selectively lithiated. Here, it is described in Tetrahedron Letters, 41 , 4335 (2000) that, when 2,5-dibromopyridine is ligated in diethyl ether or THF, the 5-position can be selectively lithiated. A similar method can be used.

The electron transport material having a 3,2'-bipyridine skeleton can be synthesized using, for example, the Negishi coupling reaction or the Suzuki coupling reaction. It can also be synthesized by combining both reactions. First, taking the case where G is a divalent linking group as an example, a method for synthesizing compound (1) in which the same 3,2'-bipyridyl group is substituted for G is exemplified below.

上記式中、Ｇは２価の基または２個の遊離原子価をもつ環系である。Ｒは短鎖のアルキルであり、通常メチル、エチル、イソプロピルなどが好適に用いられる。Ｘは塩素、臭素、ヨウ素、またはトリフラートである。Ｒ^１〜Ｒ^８の定義は前記と同じである。

In the above formula, G is a divalent group or a ring system having two free valences. R is a short-chain alkyl, and usually methyl, ethyl, isopropyl and the like are preferably used. X is chlorine, bromine, iodine, or triflate. The definitions of R ^{1 to} R ⁸ are the same as described above.

An example of the Negishi coupling reaction is shown in Scheme 2. The reaction 1-1) is a method in which two sites of G are converted to a zinc complex, and then reacted with 3,2'-bipyridine having a 2-fold mole of a reactive group in the presence of a palladium catalyst. The reaction 1-2) is a method in which G having a reactive group at two sites is reacted with a zinc complex of 2,2 mol of 3,2'-bipyridine in the presence of a palladium catalyst.

An example of the Suzuki coupling reaction is shown in Scheme 3. The reaction of 2-1) is a method in which two portions of G are converted to boronic acid or boronic ester, and then reacted with 3,2'-bipyridine having a 2-fold mole of a reactive group in the presence of a palladium catalyst. The reaction of 2-2) is a method in which G having a reactive group at two positions is reacted with a double molar amount of a boronic acid derivative of 3,2'-bipyridine in the presence of a palladium catalyst.

When a plurality of divalent groups are connected to G, or when a ring system having a plurality of two free valences is connected, or a ring having a divalent group and two free valences In the case of a combination of the systems, for example, -G ¹ -G ^1- , a 3,2′-bipyridyl group is linked to each single G ¹ using the above coupling reaction, and then a known cup The target compound may be synthesized by linking G ¹ together in a ring reaction. Also in this coupling reaction, Negishi coupling reaction, Suzuki coupling reaction, etc. are preferably used.

上記式中、Ｘ、Ｒ^１〜Ｒ^８、Ｒ、および−Ｇ−の定義は前記と同じである。 Next, taking the case where G is a divalent linking group as described above as an example, a method for synthesizing compound (1) in which G is substituted with a different 3,2′-bipyridyl group will be exemplified below.

In the above formula, the definitions of X, R ^{1 to} R ⁸ , R, and —G— are the same as described above.

Scheme 4 shows a synthesis example of the reaction intermediate (0). The reaction of 4-1) is a method in which 3,2'-bipyridine having an equimolar reactive group is reacted with anthracene in which one portion of G is a zinc complex in the presence of a palladium catalyst. The reaction of 4-2) is a method in which an anthracene having a reactive group at two positions of G is reacted with an equimolar zinc complex of 3,2'-bipyridine in the presence of a palladium catalyst. The reaction 4-3) is a method in which an anthracene in which one portion of G is boronic acid is reacted with 3,2'-bipyridine having an equimolar reactive group in the presence of a palladium catalyst and a base. In the reaction 4-4), anthracene having a reactive group at two positions of G is reacted with an equimolar amount of 3,2'-bipyridine boronic acid in the presence of a palladium catalyst and a base. In these reactions, a boronic acid ester is also preferably used in place of the boronic acid.

上記式中、Ｘ、Ｒ^１〜Ｒ^８および−Ｇ−の定義は前記と同じである。

In the above formula, the definitions of X, R ^{1 to} R ⁸ and —G— are the same as described above.

Scheme 5 shows a method for synthesizing the compound represented by the formula (1) from the reaction intermediate (0). The reaction of 5-1) is a method in which the reactive group of (0) is converted to a zinc complex, and 3,2'-bipyridine having an equimolar reactive group is reacted in the presence of a palladium catalyst. The reaction of 5-2) is a method in which (0) is reacted with an equimolar zinc complex of 3,2'-bipyridine in the presence of a palladium catalyst. The reaction 5-3) is a method in which the reactive group (0) is converted to boronic acid, and 3,2'-bipyridine having an equimolar reactive group is reacted in the presence of a palladium catalyst and a base. In the reaction 5-4), (0) is reacted with an equimolar amount of 3,2'-bipyridine boronic acid in the presence of a palladium catalyst and a base. In these reactions, a boronic acid ester is also preferably used in place of the boronic acid.

G is connected to a plurality of divalent groups, or a ring system having a plurality of two free valences is connected, or a ring having a divalent group and two free valences In the case of a combination of the systems, for example, -G ¹ -G ^1- , a 3,2′-bipyridyl group is linked to a single G ¹ using the above coupling reaction, and then a known cup The target compound may be synthesized by linking G ¹ together in a ring reaction. Also in this coupling reaction, the Suzuki coupling reaction or the Negishi coupling reaction is preferably used.

Further, when G ¹ is a heterocycle such as oxadiazole, intramolecular cyclization dehydration reaction from hydrazide obtained by reacting a cyclic acid chloride having a 3,2′-bipyridyl group with hydrazine. It is also possible to use a method of synthesis via

The compound represented by Formula (3) or the compound represented by Formula (4) can also be synthesized by appropriately combining the above synthesis methods. As mentioned above, although the synthesis method of the compound of this invention was illustrated, this invention is not restrict | limited by these illustrations.

Specific examples of the palladium catalyst used in the Negishi coupling reaction are Pd (PPh ₃ ) ₄ , PdCl ₂ (PPh ₃ ) ₂ , Pd (OAc) ₂ , tris (dibenzylideneacetone) dipalladium (0), tris (di Benzylideneacetone) dipalladium (0) chloroform complex, bis (dibenzylideneacetone) dipalladium (0), bis (tri-t-butylphosphino) palladium (0), (1,1′-bis (diphenylphosphino) ferrocene ) Dichloropalladium (II) and the like. Furthermore, specific examples of the solvent used in this reaction are benzene, toluene, xylene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butylmethyl ether, 1,4-dioxane and the like. These solvents can be appropriately selected and may be used alone or as a mixed solvent.

Specific examples of the palladium catalyst used in the Suzuki coupling reaction are Pd (PPh ₃ ) ₄ , PdCl ₂ (PPh ₃ ) ₂ , Pd (OAc) ₂ , tris (dibenzylideneacetone) dipalladium (0), tris (di Benzylideneacetone) dipalladium (0) chloroform complex, bis (dibenzylideneacetone) dipalladium (0), and the like. In order to accelerate the reaction, a phosphine compound may be added to these palladium compounds in some cases. Specific examples of the phosphine compound include tri (t-butyl) phosphine, tricyclohexylphosphine, 1- (N, N-dimethylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (N, N -Dibutylaminomethyl) -2- (di-t-butylphosphino) ferrocene, 1- (methoxymethyl) -2- (di-t-butylphosphino) ferrocene, 1,1'-bis (di-t-butylphosphino) ) Ferrocene, 2,2′-bis (di-t-butylphosphino) -1,1′-binaphthyl, 2-methoxy-2 ′-(di-t-butylphosphino) -1,1′-binaphthyl, 2- And dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl. Specific examples of the base used in this reaction are sodium carbonate, potassium carbonate, cesium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, barium hydroxide, sodium ethoxide, sodium t-butoxide, sodium acetate, phosphoric acid. Tripotassium, potassium fluoride and the like. Furthermore, specific examples of the solvent used in this reaction are benzene, toluene, xylene, N, N-dimethylformamide, tetrahydrofuran, diethyl ether, t-butylmethyl ether, 1,4-dioxane, methanol, ethanol, Isopropyl alcohol and the like. These solvents can be appropriately selected and may be used alone or as a mixed solvent.

When the compound of the present invention is used for an electron injection layer or an electron transport layer in an organic EL device, it is stable when an electric field is applied, and light emission can be obtained at a low voltage. These represent that the compound of the present invention is excellent as an electron injecting material or an electron transporting material for an electroluminescent device. The electron injection layer mentioned here is a layer for receiving electrons from the cathode to the organic layer, and the electron transport layer is a layer for transporting the injected electrons to the light emitting layer. The electron transport layer can also serve as the electron injection layer. Materials used for each layer are referred to as an electron injection material and an electron transport material.

<Description of organic EL element>
In this invention, it is an organic EL element which contains the compound represented by Formula (1) of this invention in an electron injection layer or an electron carrying layer. The organic EL element of the present invention has a high luminance retention rate during constant current driving.

Although the structure of the organic EL device of the present invention has various modes, it is basically a multilayer structure in which at least a hole transport layer, a light emitting layer, and an electron transport layer are sandwiched between an anode and a cathode. Examples of the specific configuration of the device are (1) anode / hole transport layer / light emitting layer / electron transport layer / cathode, (2) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer. / Cathode, (3) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode, etc.

Since the compound of the present invention has high electron injecting property and electron transporting property, it can be used for an electron injecting layer or an electron transporting layer alone or in combination with other materials. The organic EL device of the present invention emits blue, green, red and white light by combining a hole injection layer, a hole transport layer, a light emitting layer, etc. using other materials with the electron transport material of the present invention. It can also be obtained.

The light-emitting material or light-emitting dopant that can be used in the organic EL device of the present invention is daylight fluorescence as described in the Polymer Society of Japan, Polymer Functional Materials Series “Optical Functional Materials”, Joint Publication (1991), P236. Materials, fluorescent brighteners, laser dyes, organic scintillators, various fluorescent analysis reagents and other luminescent materials, supervised by Koji Koji, “Organic EL materials and displays” published by CMC Publishing Co., Ltd. (2001) P155-156 And a light emitting material of a triplet material as described in P170 to 172.

The compounds that can be used as the light emitting material or the light emitting dopant are polycyclic aromatic compounds, heteroaromatic compounds, organometallic complexes, dyes, polymer light emitting materials, styryl derivatives, aromatic amine derivatives, coumarin derivatives, borane derivatives, oxazines. Derivatives, compounds having a spiro ring, oxadiazole derivatives, fluorene derivatives and the like. Examples of the polycyclic aromatic compound are anthracene derivatives, phenanthrene derivatives, naphthacene derivatives, pyrene derivatives, chrysene derivatives, perylene derivatives, coronene derivatives, rubrene derivatives, and the like. Examples of heteroaromatic compounds include oxadiazole derivatives, pyrazoloquinoline derivatives, pyridine derivatives, pyran derivatives, phenanthroline derivatives, silole derivatives, thiophene derivatives having a triphenylamino group, quinacridone derivatives having a dialkylamino group or a diarylamino group Etc. Examples of organometallic complexes are zinc, aluminum, beryllium, europium, terbium, dysprosium, iridium, platinum, osmium, gold, etc., quinolinol derivatives, benzoxazole derivatives, benzothiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, A complex with a benzimidazole derivative, a pyrrole derivative, a pyridine derivative, a phenanthroline derivative, or the like. Examples of dyes are xanthene derivatives, polymethine derivatives, porphyrin derivatives, coumarin derivatives, dicyanomethylenepyran derivatives, dicyanomethylenethiopyran derivatives, oxobenzanthracene derivatives, carbostyril derivatives, perylene derivatives, benzoxazole derivatives, benzothiazole derivatives, benzimidazoles And pigments such as derivatives. Examples of the polymer light-emitting material include polyparaphenyl vinylene derivatives, polythiophene derivatives, polyvinyl carbazole derivatives, polysilane derivatives, polyfluorene derivatives, polyparaphenylene derivatives, and the like. Examples of styryl derivatives are amine-containing styryl derivatives, styrylarylene derivatives, and the like.

Other electron transport materials used in the organic EL device of the present invention are arbitrarily selected from compounds that can be used as electron transport compounds in photoconductive materials and compounds that can be used in the electron transport layer and electron injection layer of organic EL devices. Can be used.

Specific examples of such electron transport materials include quinolinol metal complexes, 2,2′-bipyridyl derivatives, phenanthroline derivatives, diphenylquinone derivatives, perylene derivatives, oxadiazole derivatives, thiophene derivatives, triazole derivatives, thiadiazole derivatives, oxine derivatives. Metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinoline derivatives, imidazopyridine derivatives, borane derivatives, and the like.

Regarding the hole injection material and the hole transport material used in the organic EL device of the present invention, in a photoconductive material, a compound conventionally used as a charge transport material for holes or a hole injection of an organic EL device is used. Any known material used for the layer and the hole transport layer can be selected and used. Specific examples thereof are carbazole derivatives, triarylamine derivatives, phthalocyanine derivatives and the like.

Each layer constituting the organic EL element of the present invention can be formed by forming a material to constitute each layer into a thin film by a method such as a vapor deposition method, a spin coating method, or a casting method. The thickness of each layer formed in this way is not particularly limited and can be appropriately set according to the properties of the material, but is usually in the range of 2 nm to 5000 nm. Note that it is preferable to employ a vapor deposition method as a method of thinning the light emitting material from the standpoint that a homogeneous film can be easily obtained and pinholes are hardly generated. When thinning using the vapor deposition method, the vapor deposition conditions differ depending on the type of the light emitting material of the present invention. Deposition conditions generally include a boat heating temperature of 50 to 400 ° C., a degree of vacuum of 10 ⁻⁶ to 10 ⁻³ Pa, a deposition rate of 0.01 to 50 nm / second, a substrate temperature of −150 to + 300 ° C., and a film thickness of 5 nm to 5 μm. It is preferable to set appropriately within the range.

The organic EL device of the present invention is preferably supported by a substrate in any of the structures described above. The substrate only needs to have mechanical strength, thermal stability, and transparency, and glass, a transparent plastic film, and the like can be used. As the anode material, metals, alloys, electrically conductive compounds and mixtures thereof having a work function larger than 4 eV can be used. Specific examples thereof include metals such as Au, CuI, indium tin oxide (hereinafter abbreviated as ITO), SnO ₂ , ZnO, and the like.

Cathode materials can use metals, alloys, electrically conductive compounds, and mixtures thereof with work functions of less than 4 eV. Specific examples thereof are aluminum, calcium, magnesium, lithium, magnesium alloy, aluminum alloy and the like. Specific examples of the alloy include aluminum / lithium fluoride, aluminum / lithium, magnesium / silver, and magnesium / indium. In order to efficiently extract light emitted from the organic EL element, it is desirable that at least one of the electrodes has a light transmittance of 10% or more. The sheet resistance as the electrode is preferably several hundred Ω / □ or less. Although the film thickness depends on the properties of the electrode material, it is usually set in the range of 10 nm to 1 μm, preferably 10 to 400 nm. Such an electrode can be produced by forming a thin film by a method such as vapor deposition or sputtering using the electrode material described above.

Next, as an example of a method for producing an organic EL device using the light emitting material of the present invention, the organic material comprising the above-mentioned anode / hole injection layer / hole transport layer / light emitting layer / electron transport material of the present invention / cathode is used. A method for creating an EL element will be described. A thin film of an anode material is formed on a suitable substrate by vapor deposition to produce an anode, and then a thin film of a hole injection layer and a hole transport layer is formed on the anode. A light emitting layer thin film is formed thereon. On this light emitting layer, the electron transport material of this invention is vacuum-deposited, a thin film is formed and it is set as an electron carrying layer. Furthermore, the target organic EL element is obtained by forming the thin film which consists of a substance for cathodes by a vapor deposition method, and making it a cathode. In the production of the organic EL element described above, the production order can be reversed, and the cathode, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode can be produced in this order.

When a DC voltage is applied to the organic EL element thus obtained, the anode may be applied with a positive polarity and the cathode with a negative polarity. When a voltage of about 2 to 40 V is applied, a transparent or translucent electrode is applied. Luminescence can be observed from the side (anode or cathode and both). The organic EL element also emits light when an alternating voltage is applied. The alternating current waveform to be applied may be arbitrary.

<Example>
Hereinafter, the present invention will be described in more detail based on examples.

Synthesis Example 1: Synthesis of Compound (2-1-1) <Synthesis of 6-bromo-3,2′-bipyridine>
Under an argon atmosphere, 7.10 g of 2,5-dibromopyridine and 350 mL of diethyl ether were placed in a flask and cooled to -78 ° C. While stirring the solution, 23 mL of n-butyllithium (1.58 mol / L, hexane solution) was added dropwise, and the mixture was stirred at −78 ° C. for 30 minutes. Next, a solution obtained by dissolving 5.90 g of 2-ethanesulfinylpyridine in 20 mL of THF was added dropwise. After stirring for 10 minutes, distilled water was added to stop the reaction. The organic layer was washed 3 times with an aqueous sodium chloride solution and then dried over magnesium sulfate overnight. After filtration and evaporation of the solvent under reduced pressure, the concentrate was purified by silica gel column chromatography using a mixed solvent of n-heptane and ethyl acetate (3: 1), and then recrystallized from heptane. -2.36 g of bromo-3,2'-bipyridine was obtained.

<Synthesis of 2,5-bis (3,2′-bipyridin-6-yl) -1,1-dimethyl-3,4-dimesitylsilole>
In an argon atmosphere, 111 mg of lithium and 2.05 g of naphthalene were stirred in 5 mL of THF for 30 minutes, and then 15 mL of THF was added and stirred overnight at room temperature. After cooling to -46 ° C, 1.38 g of bis (mesitylethynyl) dimethylsilane dissolved in 5 mL of THF was added dropwise. Next, after adding 1.10 g of t-butyl bromide dissolved in 5 mL of THF dropwise, 3.03 g of ZnCl ₂ · TMEDA was added and stirred at 0 ° C. for 30 minutes. After adding 2.07 g of 6-bromo-3,2′-bipyridine and 300 mg of PdCl ₂ (PPh ₃ ) ₂ , the mixture was returned to room temperature and then refluxed for 24 hours. After cooling, water and toluene were added and stirred, the aqueous layer was removed, and the organic layer was dried over magnesium sulfate. After filtration and concentration, the concentrate was purified by silica gel column chromatography using a mixed solvent of n-heptane and ethyl acetate (5: 1), recrystallized from toluene, and further purified by sublimation. 200 mg of bis (3,2′-bipyridin-6-yl) -1,1-dimethyl-3,4-dimesitylsilole was obtained.
1H-NMR (CDCl ₃ ) δ 0.74 (s, 6H), 1.98 (s, 12H), 2.22 (s, 6H), 6.43-7.86 (m, 14H), 8.64-9.15 (m, 4H).
LC-MS: 655 (M ^<+> ).

Synthesis Example 2: Synthesis of Compound (2-1-3) <Synthesis of 9,10-bis (4,4,5,5-tetramethyl- [1,3,2] -dioxaborolanyl) anthracene>
9,10-Dibromoanthracene, bis (pinacolato) diboron, palladium (0) bis (dibenzylideneacetone), tricyclohexylphosphine, and potassium acetate are placed in a flask and dissolved in 1,4-dioxane. Stir at reflux temperature under an argon atmosphere. After confirming that the reaction is complete, the reaction solution is cooled to room temperature, and pure water is added to extract the organic layer. The organic layer is concentrated by an evaporator, and the crude product is purified by silica gel column chromatography to obtain 9,10-bis (4,4,5,5-tetramethyl- [1,3,2] -dioxaboro. Ranyl) anthracene can be obtained.

<Synthesis of 9,10-bis (3,2′-bipyridin-6-yl) anthracene>
9,10-bis (4,4,5,5-tetramethyl- [1,3,2] -dioxaborolanyl) anthracene, 6-bromo-3,2′-bipyridine, Pd (PPh ₃ ) ₄ , Tripotassium phosphate, 1,4-dioxane and pure water are placed in a flask and stirred overnight at reflux temperature under an argon atmosphere. After completion of the heating, the reaction solution is cooled to room temperature and pure water is added to extract the organic layer. The organic layer is concentrated by an evaporator, and the concentrate is purified by silica gel column chromatography to obtain 9,10-bis (3,2′-bipyridyl-6-yl) anthracene.

Synthesis Example 3 Synthesis of Compound of Formula (2-2-4) <Synthesis of 5-bromo-3,2′-bipyridine>
Under a nitrogen atmosphere, 30 mL of a tetrahydrofuran solution containing 7.11 g of 2-bromopyridine was cooled to −78 ° C., and 35 mL of a hexane solution of 1.6 mol / L of n-butyllithium was added. After stirring at −78 ° C. for 30 minutes, 60 mL of tetrahydrofuran and 15.91 g of zinc chloride tetramethylethylenediamine were added, and the mixture was stirred at 0 ° C. for 30 minutes. After adding 3.47 g of Pd (PPh ₃ ) ₄ and 14.21 g of 3,5-dibromopyridine, 50 mL of tetrahydrofuran was added, and the mixture was stirred at reflux temperature for 3 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated with an evaporator, and purified by silica gel column chromatography (mobile phase: heptane / ethyl acetate) to obtain 5.14 g of the desired product.

<Synthesis of 2-phenylanthracene>
A flask was charged with 5.00 g of 2-chloroanthracene, 4.3 g of phenylboronic acid, 538 mg of tris (dibenzylideneacetone) dipalladium (0), 494 mg of tricyclohexylphosphine, 9.98 g of tripotassium phosphate, and 75 mL of toluene. The mixture was stirred at reflux temperature for 2 hours under an atmosphere. After completion of heating, 1.5 L of toluene was added to the reaction solution, cooled to room temperature and filtered, and the filtrate was purified by silica gel column chromatography (mobile phase: heptane). The solvent was distilled off under reduced pressure, and the concentrate was recrystallized from toluene to obtain 5.0 g of 2-phenylanthracene.

<Synthesis of 9,10-dibromo-2-phenylanthracene>
In a flask under a nitrogen atmosphere, 3.32 g of 2-phenylanthracene was dissolved in 400 mL of dichloromethane. A solution prepared by dissolving 5.00 g of bromine in 30 mL of carbon tetrachloride was added dropwise over 15 minutes. After completion of the dropping, the mixture was stirred for 2 hours at room temperature, and the reaction was stopped with an aqueous sodium thiosulfate solution. The organic layer was extracted, the solvent was distilled off under reduced pressure, and the resulting concentrate was recrystallized from 50 mL of toluene to obtain 4.4 g of 9,10-dibromo-2-phenylanthracene.

<Synthesis of 9,10-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl) -2-phenylanthracene>
9,10-dibromo-2-phenylanthracene 10.0 g, bis (pinacolato) diboron 14.8 g, bis (dibenzylideneacetone) palladium (0) 838 mg, tricyclohexylphosphine 1.02 g, potassium acetate 7.15 g and 1, 4-Dioxane 50mL was put into the flask, and it stirred at reflux temperature under argon atmosphere for 8 hours. After the heating was completed, toluene was added to the reaction solution, and after cooling to room temperature, the solid was filtered off and the filtrate was concentrated. The concentrate was purified by silica gel column chromatography (mobile phase: toluene) and then recrystallized from a tetrahydrofuran / heptane mixed solution to give 9,10-bis (4,4,5,5-tetramethyl-1,3,2). -Dioxaborolanyl) -2-phenylanthracene 8.3 g was obtained.

<Synthesis of 9,10-bis (3,2′-bipyridin-5-yl) -2-phenylanthracene>
9,10-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl) -2-phenylanthracene, 2.00 g, 5-bromo-3,2′-bipyridine 07 g, tris (dibenzylideneacetone) dipalladium (0) 220 mg, tricyclohexylphosphine 202 mg, tripotassium phosphate 5.1 g, and toluene 40 mL were placed in a flask and stirred at reflux temperature for 15 and a half hours under an argon atmosphere. After completion of heating, the reaction solution was cooled to room temperature and washed with pure water. The organic layer was concentrated, and the concentrate was purified by activated alumina column chromatography (mobile phase: toluene / ethyl acetate). The solvent was distilled off under reduced pressure, and the concentrate was washed with ethyl acetate and recrystallized from toluene to obtain 240 mg of 9,10-bis (3,2′-bipyridin-5-yl) -2-phenylanthracene.
1H-NMR (CDCl ₃ ): 7.3-7.5 (m, 7H), 7.5-7.6 (d, 2H), 7.6-7.8 (m, 3H), 7.8-7.9 (m, 6H), 8.5 (m, 2H) , 8.7-8.8 (m, 2H), 8.8-8.9 (m, 2H), 9.4-9.5 (m, 2H).

By appropriately selecting a raw material compound, another light emitting material of the present invention can be synthesized by a method according to the above synthesis example.

真空槽を１×１０^−３Ｐａまで減圧し、銅フタロシアニンが入った蒸着用ボートを加熱して、膜厚２０ｎｍになるように蒸着して正孔注入層を形成し、次いで、ＮＰＤ入りの蒸着用ボートを加熱して、膜厚３０ｎｍになるようにＮＰＤを蒸着して正孔輸送層を形成した。次に、化合物（５）を入れたモリブデン製ボートと化合物（６）を入れたモリブデン製蒸着用ボートを同時に加熱して、膜厚３５ｎｍになるように蒸着して発光層を形成した。化合物（５）と化合物（６）の重量比がおよそ９５対５になるように蒸着速度を調節した。次に化合物（２−１−１）入りの蒸着用ボートを加熱して、膜厚１５ｎｍになるように蒸着して電子輸送層を形成した。以上の蒸着速度は０．１〜０．２ｎｍ／秒であった。その後、弗化リチウム入りの蒸着用ボートを加熱して、膜厚０．５ｎｍになるように０．００３〜０．０１ｎｍ／秒の蒸着速度で蒸着し、次いで、アルミニウム入りの蒸着用ボートを加熱して、膜厚１００ｎｍになるように０．２〜０．５ｎｍ／秒の蒸着速度で蒸着することにより、有機ＥＬ素子を得た。ＩＴＯ電極を陽極、弗化リチウム／アルミニウム電極を陰極として直流電圧を印加すると、波長４５６ｎｍの青色発光を得た。また、初期輝度１０００ｃｄ／ｍ^２を得るために印加した電圧は６．３４Ｖであった。この時の電流密度を保持して定電流駆動試験を実施したところ、４０時間経過時の輝度は９００ｃｄ／ｍ^２であり、初期の輝度を基準にした輝度保持率は９０．０％であった。 A 25 mm × 75 mm × 1.1 mm glass substrate (manufactured by Tokyo Sanyo Vacuum Co., Ltd.) on which ITO was deposited to a thickness of 150 nm was used as a transparent support substrate. This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Vacuum Kiko Co., Ltd.), and a molybdenum vapor deposition boat containing copper phthalocyanine, N, N′-diphenyl-N, N′-dinaphthyl-4 , 4'-diaminobiphenyl (hereinafter abbreviated as NPD), molybdenum vapor deposition boat, the following compound (5): 9-phenyl-10- [6- (1,1 ': 3', 1 " Terphenyl-5′-yl) naphthalen-2-yl] anthracene-containing molybdenum boat, the following styrylamine derivative (6): N, N, N ′, N′-tetra (4-biphenylyl) -4,4 ′ -Molybdenum vapor deposition boat containing diaminostilbene, molybdenum vapor deposition boat containing the compound (2-1-1) obtained in Example 1, molybdenum vapor deposition boat containing lithium fluoride, and Al The tungsten deposition boat containing the bromide was attached.

Depressurize the vacuum chamber to 1 × 10 ⁻³ Pa, heat the vapor deposition boat containing copper phthalocyanine, and form a hole injection layer by vapor deposition to a film thickness of 20 nm, and then vapor deposition with NPD The boat was heated and NPD was deposited to a film thickness of 30 nm to form a hole transport layer. Next, the molybdenum boat containing the compound (5) and the molybdenum vapor deposition boat containing the compound (6) were heated at the same time and evaporated to a film thickness of 35 nm to form a light emitting layer. The deposition rate was adjusted so that the weight ratio of compound (5) to compound (6) was approximately 95 to 5. Next, the evaporation boat containing the compound (2-1-1) was heated and evaporated to a film thickness of 15 nm to form an electron transport layer. The above deposition rate was 0.1 to 0.2 nm / second. Thereafter, the vapor deposition boat containing lithium fluoride is heated to deposit at a deposition rate of 0.003 to 0.01 nm / second so that the film thickness is 0.5 nm, and then the vapor deposition boat containing aluminum is heated. Then, an organic EL element was obtained by vapor deposition at a vapor deposition rate of 0.2 to 0.5 nm / second so as to have a film thickness of 100 nm. When a direct current voltage was applied using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, blue light emission with a wavelength of 456 nm was obtained. The voltage applied to obtain an initial luminance of 1000 cd / m ² was 6.34V. When a constant current driving test was conducted while maintaining the current density at this time, the luminance after 40 hours was 900 cd / m ² and the luminance retention rate based on the initial luminance was 90.0%. .

An organic EL device can be obtained according to the method of Example 4 using the compound (2-1-3) obtained in Example 2 instead of the compound (2-1-1).

An organic EL device was obtained according to the method of Example 4 except that the compound (2-1-1) was changed to the compound (2-2-4). A constant current driving test was performed using an ITO electrode as an anode and a lithium fluoride / aluminum electrode as a cathode at a current density for obtaining an initial luminance of 1000 cd / m ² . The driving test start voltage was 7.64 V, the luminance after 40 hours was 870 cd / m ² , and the luminance retention rate after 40 hours was 87.0% based on the initial luminance.

[Comparative Example 1]
The compound (2-1-1) is replaced with the following compound (7): 2,5-bis (2,2′-bipyridin-6-yl) -1,1-dimethyl-3,4-dimethylsylsilole An organic EL device was obtained according to the method of Example 4 except that. When a direct current voltage was applied using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, blue light emission with a wavelength of 469 nm was obtained. When a constant current driving test was performed with a current density for obtaining an initial luminance of 1000 cd / m ² , the luminance after 40 hours was 700 cd / m ² and the luminance retention rate based on the initial luminance was 70.0. %Met.

[Comparative Example 2]
An organic EL device was obtained according to the method of Example 4 except that the compound (2-1-1) was changed to tris (8-quinolinol) aluminum (Alq ₃ ). When a direct current voltage was applied using the ITO electrode as the anode and the lithium fluoride / aluminum electrode as the cathode, blue-green light emission with a wavelength of 520 nm was obtained. When a constant current driving test was performed with a current density to obtain an initial luminance of 1000 cd / m ² , the luminance after 40 hours was 750 cd / m ² , and the luminance was maintained after 40 hours with reference to the initial luminance. The rate was 75.0%.

[Comparative Example 3]
An organic EL device was obtained according to the method of Example 4 except that the compound (2-1-1) was changed to the following compound (8) (compound II-4 described in Patent Document 2). A constant current driving test was performed using an ITO electrode as an anode and a lithium fluoride / aluminum electrode as a cathode at a current density for obtaining an initial luminance of 1000 cd / m ² . The luminance after the lapse of 40 hours was 615 cd / m ² , and the luminance retention rate after the lapse of 40 hours based on the initial luminance was 61.5%.

According to a preferred aspect of the present invention, it is possible to provide an organic EL element with better performance over the lifetime of the element. In particular, since the element lifetime of blue light emitting elements can be improved, a high-performance display device including the elements can be provided.

Claims (61)

A compound represented by the following formula (1).

Wherein G is an n-valent linking group that is not a single bond, n is an integer from 2 to 4; R ^{1 to} R ⁴ are independently hydrogen, a monovalent group, or a free valence bonded to G. R ^{5 to} R ⁸ are independently hydrogen or a monovalent group, but one of R ^{1 to} R ⁴ is the free valence bound to G; and n 3,2 ′ The -bipyridyl groups may be the same or different.
The compound according to claim 1, wherein one of R ^{1 to} R ⁴ is a free valence bonded to G, the other is hydrogen, and R ^{5 to} R ⁸ are hydrogen.
The compound of Claim 2 represented by following formula (2).

In the formula, G is one selected from the group of groups represented by the following formulas (G1) to (G3); one of R ^{9 to} R ¹² is a free valence bonded to G; The other is hydrogen; and one of R ¹³ -R ¹⁶ is the free valence bonded to G, the other is hydrogen.

Wherein, ^{G 1} is independently one selected from the group of compounds represented by the following formula (A-1) ~ (A -24) and formula (B-1) ~ (B -41) Is a divalent group derived from

In the above formula, R is independently hydrogen, alkyl having 1 to 8 carbons, cycloalkyl having 3 to 10 carbons, or aryl having 6 to 20 carbons; formulas (A-1) to (A- 23) and the divalent group derived from the compounds represented by formulas (B-1) to (B-41) may have a substituent at a position other than an atom having a free valence.
The compound of Claim 3 represented by a following formula (2-1).

In the formula, the definition of G is the same as G in Formula (2).
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -24) 5. A compound according to claim 4 which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 5. A compound according to claim 4 which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -13) The compound according to claim 4, which is one selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-13) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G2) according to claim 3, and in the formula (G2), G ¹ is a formula (A-1) to (A-24) and a formula (B-1) to The compound according to claim 4, which is the same divalent group derived from one selected from the group of compounds represented by (B-41).
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 5. A compound according to claim 4 which is the same divalent group derived from one selected.
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -7) 5. A compound according to claim 4 which is the same group selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-7) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound according to claim 4, wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by formulas (A-1) to (A-24) according to claim 3. Yes; G ^1B is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41) according to claim 3 .
G is a linking group represented by the formula (G3-1); G ^1B is the same selected from the group of divalent groups represented by the following formulas (D-1) to (D-15) 12. A compound according to claim 11 which is a group.

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G3-2); G ^1A is the same selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) The compound according to claim 11, which is a group and G ^1B is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
G is a linking group represented by the formula (G3-3); G ^1A is one selected from the group of divalent groups represented by the following formulas (C-1) to (C-4) The compound according to claim 11, wherein G ^1B is the same group selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-4) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
The compound of Claim 11 whose G is a coupling group represented by a following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-9), and G ^1B2 is the following formula (D-1) It is the same group selected from the group of the bivalent group represented by-(D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound of Claim 3 represented by a following formula (2-2).

In the formula, the definition of G is the same as G in Formula (2).
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -24) 17. A compound according to claim 16, which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 17. A compound according to claim 16, which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -13) The compound according to claim 16, which is one selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-13) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G2) according to claim 3, and in the formula (G2), G ¹ is a formula (A-1) to (A-24) and a formula (B-1) to The compound according to claim 16, which is the same divalent group derived from one selected from the group of compounds represented by (B-41).
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 17. A compound according to claim 16 which is the same divalent group derived from one selected.
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -7) 17. A compound according to claim 16 which is the same group selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-7) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound according to claim 16, wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by formulas (A-1) to (A-24) according to claim 3. Yes; G ^1B is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41) according to claim 3 .
G is a linking group represented by the formula (G3-1); G ^1B is the same selected from the group of divalent groups represented by the following formulas (D-1) to (D-15) 24. A compound according to claim 23 which is a group.

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G3-2); G ^1A is the same selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) ^24. The compound according to claim 23, which is a group and G ^1B is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
G is a linking group represented by the formula (G3-3); G ^1A is one selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) The compound according to claim 23, wherein G ^1B is the same group selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
The compound according to claim 23, wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-9), and G ^1B2 is the following formula (D-1) It is the same group selected from the group of the bivalent group represented by-(D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound of Claim 3 represented by a following formula (2-3).

In the formula, the definition of G is the same as G in Formula (2).
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -24) 29. The compound of claim 28, which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 29. The compound of claim 28, which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -13) 29. The compound of claim 28, which is one selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-13) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), ^{G 1} has the formula (A-1) ~ (A -24) and formula (B-1) ~ 29. The compound according to claim 28, which is the same divalent group derived from one selected from the group of compounds represented by (B-41).
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 29. The compound of claim 28, wherein the compound is the same divalent group derived from one selected.
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -7) 29. The compound of claim 28, wherein the compound is the same group selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-7) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound according to claim 28, wherein G is a linking group represented by any one of the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by formulas (A-1) to (A-24) according to claim 3. Yes; G ^1B is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41) according to claim 3 .
G is a linking group represented by the formula (G3-1); G ^1B is the same selected from the group of divalent groups represented by the following formulas (D-1) to (D-15) 36. A compound according to claim 35 which is a group.

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G3-2); G ^1A is the same selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) 36. The compound according to claim 35, which is a group and G ^1B is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
G is a linking group represented by the formula (G3-3); G ^1A is one selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) 36. The compound according to claim 35, wherein G ^1B is the same group selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
36. The compound according to claim 35, wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-9), and G ^1B2 is the following formula (D-1) It is the same group selected from the group of the bivalent group represented by-(D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound of Claim 3 represented by a following formula (2-4).

In the formula, the definition of G is the same as G in Formula (2).
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -24) 41. The compound of claim 40, which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 41. The compound of claim 40, which is a divalent group derived from one selected.
G is a linking group represented by the formula (G1) according to claim 3, wherein (G1), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -13) 41. The compound of claim 40, which is one selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-13) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), ^{G 1} has the formula (A-1) ~ (A -24) and formula (B-1) ~ 41. The compound according to claim 40, which is the same divalent group derived from one selected from the group of compounds represented by (B-41).
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), from the group of ^{compounds G 1} is represented by the formula (A-1) ~ (A -16) 41. The compound of claim 40, which is the same divalent group derived from one selected.
G is a linking group represented by the formula (G2) as claimed in claim 3, wherein (G2), 2 ^{valent G 1} is represented by the following formula (C-1) ~ (C -7) 41. The compound of claim 40, which is the same group selected from the group of

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (C-1) to (C-7) The divalent group represented may have a substituent at a position other than the atom having a free valence.
41. The compound according to claim 40, wherein G is a linking group represented by the following formulas (G3-1) to (G3-3).

In the formula, G ^1A is independently a divalent group derived from one selected from the group of compounds represented by formulas (A-1) to (A-24) according to claim 3. Yes; G ^1B is independently a divalent group derived from one selected from the group of compounds represented by formulas (B-1) to (B-41) according to claim 3 .
G is a linking group represented by the formula (G3-1); G ^1B is the same selected from the group of divalent groups represented by the following formulas (D-1) to (D-15) 48. A compound according to claim 47 which is a group.

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
G is a linking group represented by the formula (G3-2); G ^1A is the same selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) ^48. The compound according to claim 47, which is a group, and G ^1B is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
G is a linking group represented by the formula (G3-3); G ^1A is one selected from the group of divalent groups represented by the following formulas (C-1) to (C-7) 48. The compound according to claim 47, wherein G ^1B is the same group selected from the group of divalent groups represented by the following formulas (D-1) to (D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; formulas (C-1) to (C-7) and The divalent groups represented by formulas (D-1) to (D-15) may have a substituent at a position other than an atom having a free valence.
48. The compound according to claim 47, wherein G is a linking group represented by the following formula (G3-4).

In the formula, G ^1B1 is one selected from the group of divalent groups represented by the following formulas (D-1) to (D-9), and G ^1B2 is the following formula (D-1) It is the same group selected from the group of the bivalent group represented by-(D-15).

In the above formula, R is independently hydrogen, methyl, ethyl, hexyl, cyclohexyl, mesityl, xylyl, phenyl, 1-naphthyl or 2-naphthyl; in formulas (D-1) to (D-15) The divalent group represented may have a substituent at a position other than the atom having a free valence.
The compound of Claim 2 represented by following formula (3).

In the formula, G is a group represented by the following formula (G4) or (G5); one of R ^{17 to} R ²⁰ is a free valence bonded to G, and the other is hydrogen; ^{One of 21 to} R ²⁴ is a free valence bonded to G and the other is hydrogen; one of R ^{25 to} R ²⁸ is a free valence bonded to G and the other is hydrogen .

In the formula, G ¹ is independently one selected from the group of compounds represented by the following formulas (A-1) to (A-24) and formulas (B-1) to (B-41) G ^2A is one selected from the group of trivalent groups represented by the following formulas (E-1) to (E-9), and G ^2B Is one selected from the group of boron, nitrogen, phosphoryl groups, or trivalent groups represented by formulas (E-1) to (E-9).

In the above formula, R is independently hydrogen, alkyl having 1 to 8 carbons, cycloalkyl having 3 to 10 carbons, or aryl having 6 to 20 carbons; formulas (A-1) to (A- 24) and the divalent group derived from the compounds represented by formulas (B-1) to (B-41) may have a substituent at a position other than an atom having a free valence.

G is a linking group represented by the formula (G5), ^{G 1} is the same in the formula (G5), compound of claim 52.
The compound of Claim 2 represented by following formula (4).

In the formula, G is a group represented by the following formula (G6) or (G7); one of R ^{29 to} R ³² is a free valence bonded to G, and the other is hydrogen; ^{One of 33 to} R ³⁶ is a free valence bonded to G and the other is hydrogen; one of R ^{37 to} R ⁴⁰ is a free valence bonded to G and the other is hydrogen One of R ^{41 to} R ⁴⁴ is a free valence bonded to G, and the other is hydrogen.

In the formula, G ¹ is independently one selected from the group of compounds represented by the following formulas (A-1) to (A-24) and formulas (B-1) to (B-41) G ^3A is one selected from the group of tetravalent groups represented by the following formulas (F-1) to (F-8); G ^3B Is one selected from carbon, silicon, or a group of tetravalent groups represented by formulas (F-1) to (F-8).

In the above formula, R is independently hydrogen, alkyl having 1 to 8 carbons, cycloalkyl having 3 to 10 carbons, or aryl having 6 to 20 carbons; formulas (A-1) to (A- 24) and the divalent group derived from the compounds represented by formulas (B-1) to (B-41) may have a substituent at a position other than an atom having a free valence.

G is a linking group represented by the formula (G7), ^{G 1} is the same in the formula (G7), the compound according to claim 54.
G ¹ is a divalent group represented by the formula (C-1), compound of Claim 7.
G ¹ is a 1,1-dimethyl-3,4-dimethyl cytidine Resid roll-2,5-diyl, A compound according to claim 7.
The compound according to claim 7, wherein G ¹ is a divalent group represented by the formula (C-2).
G ¹ is an anthracene-9,10-diyl, the compound according to claim 7.
The organic electroluminescent element containing the compound of any one of Claims 1-59.
The organic electroluminescence device having at least a hole transport layer, a light emitting layer, and an electron transport layer sandwiched between an anode and a cathode, the electron transport layer according to any one of claims 1 to 59. An organic electroluminescence device containing a compound.