JP6846263B2 - New compounds, organic electroluminescence devices, electronic devices - Google Patents

Description

The present invention relates to novel compounds, organic electroluminescent devices and electronic devices.

The organic electroluminescence device (hereinafter, may be referred to as "organic EL device") is expected to be used as an inexpensive large-area full-color display device of a solid-state light emitting type, and many developments have been made. Generally, an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When a voltage is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. The injected electrons and holes recombine in the light emitting layer to generate an excited state, and when the excited state returns to the ground state, energy is emitted as light.

The element performance of the conventional organic EL element has not been sufficient yet. In order to improve the device performance, the materials used for the organic EL device are being gradually improved (for example, Patent Documents 1 to 7), but further improvement in performance is required. In particular, improving the life of an organic EL element is an important issue that leads to the life of a practically used product, and therefore, a material capable of realizing an organic EL element having a long life is required.

Patent Documents 1 and 2 disclose compounds having a 2-fluoranthenyl group and a 2-benzimidazolyl group. Patent Document 3 discloses a compound having a 3-fluoranthenyl group and a 2-benzimidazolyl group. Patent Documents 4 and 5 disclose compounds having an 8-fluoranthenyl group and a 2-benzimidazolyl group. Patent Documents 6 and 7 disclose compounds having a 3- or 8-fluoranthenyl group and a 1,2-, 2-, or 5-benzimidazolyl group.

Chinese Patent Application Publication No. 1035432499 Chinese Patent Application Publication No. 103187531 U.S. Patent Application Publication No. 2014/0284580 International Publication No. 2013/182046 Korean Patent No. 2011-137897 International Publication No. 2011/086935 International Publication No. 2011/086941

An object of the present invention is to provide a compound capable of producing an organic EL device having a long life.

（式（１）中、Ａ及びＲ^１〜Ｒ^１３は、それぞれ、水素原子、ハロゲン原子、ヒドロキシ基、シアノ基、置換もしくは無置換の炭素数１〜２５のアルキル基、置換もしくは無置換の炭素数２〜２５のアルケニル基、置換もしくは無置換の炭素数２〜２５のアルキニル基、置換もしくは無置換の環形成炭素数３〜２５のシクロアルキル基、置換もしくは無置換の炭素数１〜２５のアルコキシ基、置換もしくは無置換の環形成炭素数６〜３０のアリール基、置換もしくは無置換の炭素数７〜３１のアラルキル基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリール基、置換もしくは無置換の環形成炭素数６〜３０のアリールオキシ基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリールオキシ基、置換もしくは無置換の炭素数１〜２５のアルキルチオ基、置換もしくは無置換の環形成炭素数６〜３０のアリールチオ基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリールチオ基、−ＳｉＺ^７ _３で表される基（Ｚ^７は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−ＢＺ^８ _２で表される基（Ｚ^８は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−ＮＺ^９ _２で表される基（Ｚ^９は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−（Ｃ＝Ｏ）Ｚ^１０で表される基（Ｚ^１０は、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、又は−Ｐ（＝Ｏ）Ｚ^１１ _２で表される基（Ｚ^１１は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）である。
Ｒ^１〜Ｒ^４のいずれか２つは互いに結合して環を形成してもよい。Ｒ^５〜Ｒ^１３のいずれか２つは互いに結合して環を形成してもよい。
Ｌは、置換もしくは無置換の環形成炭素数６〜３０のアリーレン基、又は置換もしくは無置換の環形成原子数５〜３０のヘテロアリーレン基である。
ｎは、０〜３の整数である。ｎが０の場合、（Ｌ）ｎは単結合である。ｎが２以上の場合、複数のＬはそれぞれ同一でも異なってもよい。） As a result of intensive studies to achieve the above object, the present inventors have obtained an organic EL element having an excellent life by using a specific compound having a 2-fluoranthenyl group and a 1-benzimidazolyl group. The present invention was completed.
According to the present invention, the following compounds and the like are provided.
A compound represented by the following formula (1).

(In formula (1), A and R 1 to R 13 are hydrogen atom, halogen atom, hydroxy group, cyano group, substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, substituted or unsubstituted carbon, respectively. An alkenyl group of number 2 to 25, a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted ring-forming group having 3 to 25 carbon atoms, a substituted or unsubstituted ring-forming group having 1 to 25 carbon atoms. Alkoxy groups, substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 31 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms, Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted ring-forming atomics with 5 to 30 heteroaryloxy groups, substituted or unsubstituted alkylthio groups with 1 to 25 carbon atoms, substituted or unsubstituted ring formation arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted ring atoms 5-30 heteroarylthio groups, group (Z 7 represented by -SiZ 7 3 are each hydrogen atom, an alkyl group having 1 to 25 carbon atoms, a heteroaryl group ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5-30,), -, a group represented by BZ 8 2 (Z 8 are each a hydrogen atom, an alkyl group, ring-forming aryl group having 6 to 30 carbon atoms or heteroaryl group having ring atoms of 5 to 30, 1 to 25 carbon atoms), - represented by NZ 9 2 (Z 9 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms, respectively),-( C = O) group (Z 10 represented by Z 10 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms or heteroaryl ring atoms 5 to 30, a group), or -P (= O) Z 11 2, a group represented by (Z 11 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms, Alternatively, it is a heteroaryl group having 5 to 30 ring-forming atoms).
Any two of R 1 to R 4 may be combined with each other to form a ring. Any two of R 5 to R 13 may be combined with each other to form a ring.
L is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms or a heteroarylene group having 5 to 30 substituted or unsubstituted ring-forming atoms.
n is an integer from 0 to 3. When n is 0, (L) n is a single bond. When n is 2 or more, the plurality of Ls may be the same or different. )

According to the present invention, it is possible to provide a compound capable of producing an organic EL device having a long life.

（式（１）中、Ａ及びＲ^１〜Ｒ^１３は、それぞれ、水素原子、ハロゲン原子、ヒドロキシ基、シアノ基、置換もしくは無置換の炭素数１〜２５のアルキル基、置換もしくは無置換の炭素数２〜２５のアルケニル基、置換もしくは無置換の炭素数２〜２５のアルキニル基、置換もしくは無置換の環形成炭素数３〜２５のシクロアルキル基、置換もしくは無置換の炭素数１〜２５のアルコキシ基、置換もしくは無置換の環形成炭素数６〜３０のアリール基、置換もしくは無置換の炭素数７〜３１のアラルキル基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリール基、置換もしくは無置換の環形成炭素数６〜３０のアリールオキシ基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリールオキシ基、置換もしくは無置換の炭素数１〜２５のアルキルチオ基、置換もしくは無置換の環形成炭素数６〜３０のアリールチオ基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリールチオ基、−ＳｉＺ^７ _３で表される基（Ｚ^７は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−ＢＺ^８ _２で表される基（Ｚ^８は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−ＮＺ^９ _２で表される基（Ｚ^９は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−（Ｃ＝Ｏ）Ｚ^１０で表される基（Ｚ^１０は、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、又は−Ｐ（＝Ｏ）Ｚ^１１ _２で表される基（Ｚ^１１は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）である。
Ｒ^１〜Ｒ^４のいずれか２つは互いに結合して環を形成してもよい。Ｒ^５〜Ｒ^１３のいずれか２つは互いに結合して環を形成してもよい。
Ｌは、置換もしくは無置換の環形成炭素数６〜３０のアリーレン基、又は置換もしくは無置換の環形成原子数５〜３０のヘテロアリーレン基である。
ｎは、０〜３の整数である。ｎが０の場合、（Ｌ）ｎは単結合である。ｎが２以上の場合、複数のＬはそれぞれ同一でも異なってもよい。） [New compound]
The compound according to one aspect of the present invention is represented by the following formula (1).

(In formula (1), A and R 1 to R 13 are hydrogen atom, halogen atom, hydroxy group, cyano group, substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, substituted or unsubstituted carbon, respectively. An alkenyl group of number 2 to 25, a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted ring-forming group having 3 to 25 carbon atoms, a substituted or unsubstituted ring-forming group having 1 to 25 carbon atoms. Alkoxy groups, substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 31 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms, Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted ring-forming atomics with 5 to 30 heteroaryloxy groups, substituted or unsubstituted alkylthio groups with 1 to 25 carbon atoms, substituted or unsubstituted ring formation arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted ring atoms 5-30 heteroarylthio groups, group (Z 7 represented by -SiZ 7 3 are each hydrogen atom, an alkyl group having 1 to 25 carbon atoms, a heteroaryl group ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5-30,), -, a group represented by BZ 8 2 (Z 8 are each a hydrogen atom, an alkyl group, ring-forming aryl group having 6 to 30 carbon atoms or heteroaryl group having ring atoms of 5 to 30, 1 to 25 carbon atoms), - represented by NZ 9 2 (Z 9 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms, respectively),-( C = O) group (Z 10 represented by Z 10 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms or heteroaryl ring atoms 5 to 30, a group), or -P (= O) Z 11 2, a group represented by (Z 11 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms, Alternatively, it is a heteroaryl group having 5 to 30 ring-forming atoms).
Any two of R 1 to R 4 may be combined with each other to form a ring. Any two of R 5 to R 13 may be combined with each other to form a ring.
L is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms or a heteroarylene group having 5 to 30 substituted or unsubstituted ring-forming atoms.
n is an integer from 0 to 3. When n is 0, (L) n is a single bond. When n is 2 or more, the plurality of Ls may be the same or different. )

By using the compound according to one aspect of the present invention, an organic EL device having a long life can be manufactured.

L is preferably a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms, and more preferably a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

n is preferably an integer of 1-3, more preferably 1 or 2.
When n is 2 or more, the plurality of Ls may be the same or different. The term "different L" includes not only the case where a plurality of L are different groups derived from different compounds, but also the case where they are derived from the same compound and differ only in the binding position. For example, (L) n is a biphenylene structure composed of an m-phenylene group and an m-phenylene group, a biphenylene structure composed of an m-phenylene group and a p-phenylene group, or a biphenylene structure composed of an m-phenylene group and an o-phenylene group. It may be.

A is preferably a group other than a hydrogen atom, more preferably a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group. A substituted heteroaryl group having 5 to 30 ring-forming atoms, more preferably a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Yes, more preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

R ^{1 to} R ¹³ are preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group, respectively. It is a heteroaryl group having 5 to 30 ring-forming atoms.
R ^{1 to} R ⁴ may be hydrogen atoms. R ^{5 to} R ⁹ may be hydrogen atoms. R ^{10 to} R ¹³ may be hydrogen atoms. R ^{5 to} R ¹³ may be hydrogen atoms. R ^{1 to} R ¹³ may be hydrogen atoms.

Any two of R ^{1 to} R ⁴ may or may not be bonded to each other to form a ring. Any two of R ^{5 to} R ¹³ (for example, R ¹¹ and R ¹² ) may or may not be bonded to each other to form a ring.

（式（１０）中、Ａ及びＲ^１〜Ｒ^１３は式（１）と同じである。ｍは１〜３の整数である。ｍが２以上の場合、複数のフェニレン基の構造は、それぞれ同一でも異なってもよい。）

（式（１１）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（１２）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（１３）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（１４）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（１５）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（１６）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（１７）中、Ａ及びＲ^１〜Ｒ^１３は式（１０）と同じである。）

（式（２０）中、Ｒ^１〜Ｒ^１３、Ｌ及びｎは、前記式（１）と同じである。
Ｒ^１４〜Ｒ^１８は、それぞれ、水素原子、ハロゲン原子、シアノ基、置換もしくは無置換の炭素数１〜２５のアルキル基、置換もしくは無置換の炭素数２〜２５のアルケニル基、置換もしくは無置換の炭素数２〜２５のアルキニル基、置換もしくは無置換の環形成炭素数３〜２５のシクロアルキル基、置換もしくは無置換の炭素数１〜２５のアルコキシ基、置換もしくは無置換の環形成炭素数６〜３０のアリール基、置換もしくは無置換の炭素数７〜３１のアラルキル基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリール基、置換もしくは無置換の環形成炭素数６〜３０のアリールオキシ基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリールオキシ基、置換もしくは無置換の炭素数１〜２５のアルキルチオ基、置換もしくは無置換の環形成炭素数６〜３０のアリールチオ基、置換もしくは無置換の環形成原子数５〜３０のヘテロアリールチオ基、−ＳｉＺ^７ _３で表される基（Ｚ^７は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−ＢＺ^８ _２で表される基（Ｚ^８は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−ＮＺ^９ _２で表される基（Ｚ^９は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、−（Ｃ＝Ｏ）Ｚ^１０で表される基（Ｚ^１０は、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）、又は−Ｐ（＝Ｏ）Ｚ^１１ _２で表される基（Ｚ^１１は、それぞれ、水素原子、炭素数１〜２５のアルキル基、環形成炭素数６〜３０のアリール基、もしくは環形成原子数５〜３０のヘテロアリール基である）である。）

（式（３０）中、Ｒ^１〜Ｒ^１８は、前記式（２０）と同じである。
ｍは１〜３の整数である。ｍが２以上の場合、複数のフェニレン基の構造は、それぞれ同一でも異なってもよい。） The compound according to one aspect of the present invention is preferably represented by the following formulas (10) to (17), (20) or (30).

(In the formula (10), A and R ^{1 to} R ¹³ are the same as those in the formula (1). M is an integer of 1 to 3. When m is 2 or more, the structures of the plurality of phenylene groups are different, respectively. It may be the same or different.)

(In the formula (11), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (12), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (13), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (14), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (15), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (16), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (17), A and R ^{1 to} R ¹³ are the same as the formula (10).)

(In the formula (20), R 1 to R 13 , L and n are the same as those in the formula (1).
R 14 to R 18 are hydrogen atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, substituted or unsubstituted, respectively. Alkinyl group having 2 to 25 carbon atoms, substituted or unsubstituted ring-forming carbon number 3 to 25 cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted ring-forming carbon number 6 to 30 aryl groups, substituted or unsubstituted aralkyl groups having 7 to 31 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms, substituted or unsubstituted ring-forming carbon atoms 6 to 30 Aryloxy groups, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring-forming atoms, substituted or unsubstituted alkylthio groups having 1 to 25 carbon atoms, substituted or unsubstituted ring-forming carbon atoms of 6 to 30 arylthio group, a substituted or unsubstituted ring atoms 5-30 heteroarylthio groups, group (Z 7 represented by -SiZ 7 3 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, the ring forming an aryl group having 6 to 30 carbon atoms, or a heteroaryl group ring atoms 5-30) - group (Z 8 represented by BZ 8 2 are each a hydrogen atom, a carbon number 1 to 25 alkyl group, a heteroaryl group ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5-30,), -, a group represented by NZ 9 2 (Z 9 are each a hydrogen atom, An alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms), and a group represented by − (C = O) Z 10 ( Z 10 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms), or −P (= O). group (Z 11 represented by Z 11 2 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5 to 30 heteroaryl group, Is). )

(In the formula (30), R ^{1 to} R ¹⁸ are the same as the above formula (20).
m is an integer of 1-3. When m is 2 or more, the structures of the plurality of phenylene groups may be the same or different. )

R ^{14 to} R ¹⁸ are preferably hydrogen atoms and substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, respectively.
R ^{14 to} R ¹⁸ may be hydrogen atoms. R ¹⁶ may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (protium), deuterium (deuterium), and tritium (tritium).

In the present specification, the ring-forming carbon number constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in an atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbons forming the ring. The "ring-forming carbon number" described below shall be the same unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridinyl group has 5 ring-forming carbon atoms, and a flanyl group has 4 ring-forming carbon atoms. When, for example, an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms. When, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms of the fluorene ring as a substituent is not included in the number of ring-forming carbon atoms.

In the present specification, the number of ring-forming atoms refers to a compound having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, or a ring assembly) (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, or a complex). It represents the number of atoms constituting the ring itself of the ring compound). Atoms that do not form a ring and atoms included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below shall be the same unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. Hydrogen atoms bonded to carbon atoms of the pyridine ring and quinazoline ring and atoms constituting substituents are not included in the number of ring-forming atoms. When, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.

In the present specification, the "carbon number XX to YY" in the expression "ZZ group having a substituted or unsubstituted carbon number XX to YY" represents the carbon number when the ZZ group is unsubstituted, and is substituted. If so, the carbon number of the substituent is not included.
In the present specification, the "atomic number XX to YY" in the expression "ZZ group of atomic number XX to YY substituted or unsubstituted" represents the number of atoms when the ZZ group is unsubstituted, and is substituted. If so, the number of atoms of the substituent is not included.
In the present specification, the term "unsubstituted" in the case of "substituent or unsubstituted" means that the substituent is not substituted and a hydrogen atom is bonded.

Each group represented by each of the above formulas will be described in detail below.

Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like, and a fluorine atom is preferable.

The alkyl group includes methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, pentyl group (including isomer group), and hexyl group (isomer). Group (including group), heptyl group (including isomer group), octyl group (including isomer group), nonyl group (including isomer group), decyl group (including isomer group), undecyl group (isomer) (Including group), dodecyl group (including isomer group) and the like.
The alkyl group preferably has 1 to 25 carbon atoms, more preferably 1 to 8 carbon atoms.

Examples of the alkenyl group include the above-mentioned group having a double bond in the molecule of the alkyl group.
The alkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
Examples of the alkenyl group include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a pentadienyl group, a hexenyl group, a hexadienyl group, a heptenyl group, an octenyl group, an octadienyl group, a 2-ethylhexenyl group and a decenyl group.

Examples of the alkynyl group include the above-mentioned group having a triple bond in the molecule of the alkyl group.
The alkynyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 6 carbon atoms.
Examples of the alkynyl group include an ethynyl group and a methylethynyl group.

Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, a norbornyl group and the like.
The ring-forming carbon number of the cycloalkyl group is preferably 3 to 25, more preferably 3 to 8, and even more preferably 3 to 6.

The alkoxy group is represented as ^{−OZ 1, and examples of Z 1} include the above-mentioned alkyl group.
Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a t-butoxy group and the like.

Examples of the aryl group include a phenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzoantryl group, an aceanthryl group, a phenalenyl group, a phenanthryl group, a naphthacenyl group, a pentasenyl group, a pisenyl group, a pentaphenyl group and a pyrenyl group. Chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, s-indacenyl group, as-indacenyl group, triphenylenyl group, fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, spirofluorenyl group , Biphenylyl group, biphenylenyl group, terphenyl group, fluoranthenyl group, benzofluoranthenyl group, perylenyl group and the like.
The ring-forming carbon number of the aryl group is preferably 6 to 30, more preferably 6 to 18.
Examples of the arylene group include a divalent group corresponding to the above-mentioned aryl group.

The aralkyl group is a group composed of a combination of an alkyl group and an aryl group, the aryl group portion of the aralkyl group is the same as the above aryl group, and the alkyl group portion of the aralkyl group is the same as the above alkyl group. ..
Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group and the like.

Examples of the heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazole pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazine group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group and an isooxazolyl group. , Isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindrill group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, indridinyl group, quinolidinyl group, quinolyl group. , Isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzthiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, dibenzofuranyl group, Naftbenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, carbazolyl group (N-carbazolyl group and C-carbazolyl group), benzocarbazolyl group (benzo-N-carbazolyl group and benzo-C-carbazolyl group) ), Phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxadinyl group, xanthenyl group and the like.
The number of ring-forming atoms of the heteroaryl group is preferably 5 to 30, more preferably 5 to 13.
Examples of the heteroarylene group include divalent groups corresponding to the above heteroaryl groups.

The above-mentioned "carbazolyl group" also includes the following structures.

（式中、Ｘ^１〜Ｘ^６，Ｙ^１〜Ｙ^６はそれぞれ酸素原子、硫黄原子、又は−ＮＲａ−基である。Ｒａは、上記Ｒ^１４〜Ｒ^１８と同じである。） The heteroaryl group also includes the following structures.

(In the formula, X ^{1 to} X ⁶ and Y ^{1 to Y 6} are oxygen atoms, sulfur atoms, or -NRa- groups, respectively. Ra is the same as ^{R 14 to} R ^{18 above.)}

The aryloxy group is represented as ^{-OZ 2, and examples of Z 2} include the above-mentioned aryl group.
Examples of the aryloxy group include a phenoxy group, a biphenyloxy group, a terphenyloxy group and the like.

The heteroaryloxy group is represented as ^{-OZ 3, and examples of Z 3} include the above heteroaryl groups.

The alkylthio group is represented as ^{−SZ 4, and examples of Z 4} include the above alkyl groups.
Examples of the alkylthio group include a methylthio group and an ethylthio group.

Arylthio group is represented as -SZ ^5, include the above aryl groups as examples of ^{Z 5.}
Examples of the arylthio group include phenylthio and the like.

The heteroarylthio group is represented as ^{-SZ 6, and examples of Z 6} include the heteroaryl group described above.

In the silyl group represented by -SiZ ⁷ _3, alkyl group, aryl group ^{Z 7,} the heteroaryl group is as described above. Z ⁷ may be the same or different. As Z ⁷ , an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms or a heteroaryl group having 5 to 30 ring-forming atoms is preferable, and an alkyl group having 1 to 25 carbon atoms or a ring is preferable. Aryl groups having 6 to 30 carbon atoms are more preferable.
Examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a propyldimethylsilyl group, a triisopropylsilyl group, a triphenylsilyl group, a phenyldimethylsilyl group, a t-butyldiphenylsilyl group and a tritrylsilyl group. The basis etc. can be mentioned.

In boryl group represented by -BZ ⁸ _2, alkyl groups, aryl groups Z ^8, the heteroaryl group is as described above. Z ⁸ may be the same or different. As Z ⁸ , an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms is preferable.

At the amino group represented by -NZ ⁹ _2, alkyl groups, aryl groups Z ^9, the heteroaryl group is as described above. Z ⁹ may be the same or different. As Z ⁹ , an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms or a heteroaryl group having 5 to 30 ring-forming atoms is preferable, and an aryl group having 6 to 30 ring-forming carbon atoms or an aryl group having 6 to 30 ring-forming atoms is preferable. Heteroaryl groups having 5 to 30 ring-forming atoms are preferable.

- In (C = ^O) a carbonyl-containing group represented by ^{Z 10,} alkyl group of ^{Z 10,} aryl, heteroaryl are as described above. As Z ¹⁰ , an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms is preferable.

In -P (= ^O) phosphoryl group represented by ^{Z 11 _2,} an alkyl group, an aryl group of ^{Z 11,} the heteroaryl group is as described above. Z ¹¹ may be the same or different. As Z ¹¹ , an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heteroaryl group having 5 to 30 ring-forming atoms is preferable, and an alkyl group having 1 to 25 carbon atoms or a ring is preferable. Aryl groups having 6 to 30 carbon atoms are more preferable.

These substituents may be further substituted by the above substituents. Further, a plurality of these substituents may be bonded to each other to form a ring.

The compound according to one aspect of the present invention can be synthesized by following the synthesis method described in Examples and using a known alternative reaction or raw material suitable for the desired product.

Examples of the compound according to one aspect of the present invention are shown below.

The above compounds can be used as materials for organic electroluminescence (EL) devices, preferably electron transport materials.

[Organic EL element]
In the organic EL device according to one aspect of the present invention, one or more organic thin film layers including at least a light emitting layer are sandwiched between the cathode and the anode, and at least one layer of the organic thin film layer is represented by the above formula (1). The compound is contained alone or as a component of a mixture.

The organic EL device preferably has an electron transport band between the light emitting layer and the cathode, has an organic thin film layer having one or more electron transport bands, and at least one layer of the organic thin film layer is a formula. Includes the compound represented by (1). The at least one layer is preferably an electron transport layer.

As a typical element configuration of the organic EL element, a structure in which the following structures (1) to (4) are laminated on a substrate is exemplified.
(1) Anode / light emitting layer / cathode (2) anode / hole transport band / light emitting layer / cathode (3) anode / light emitting layer / electron transport band / cathode (4) anode / hole transport band / light emitting layer / electron Transport band / cathode (“/” indicates that each layer is stacked adjacent to each other)

The electron transport band usually consists of one or more layers selected from an electron injection layer and an electron transport layer. The hole transport zone usually consists of one or more layers selected from a hole injection layer and a hole transport layer.
Hereinafter, each layer of the organic EL element will be described.

(substrate)
The substrate is used as a support for the light emitting element. As the substrate, for example, glass, quartz, plastic or the like can be used. Moreover, you may use a flexible substrate. The flexible substrate is a bendable (flexible) substrate, and examples thereof include a plastic substrate made of polycarbonate and polyvinyl chloride.

(anode)
For the anode formed on the substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , Graphene and the like. In addition, gold (Au), platinum (Pt), a nitride of a metallic material (for example, titanium nitride) and the like can be mentioned.

(Hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, renium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, etc. Examples thereof include tungsten oxides, manganese oxides, aromatic amine compounds, acceptor (electron-attracting) compounds or polymer compounds (oligoforms, dendrimers, polymers, etc.).

As the compound used for the hole injection layer, an aromatic amine derivative or an acceptor compound is preferable, and an acceptor compound is more preferable. As the acceptor compounds, heterocyclic derivatives having an electron-withdrawing group, quinone derivatives having an electron-withdrawing group, an aryl borane derivative is suitable heteroaryl borane derivatives, and, hexacyanohexaazatriphenylene hexaazatriphenylene, F ₄ TCNQ (2,3 , 5,6-Tetrafluoro-7,7,8,8-Tetracyanoquinodimethane), or 1,2,3-Tris [(cyano) (4-cyano-2,3,5,6-tetrafluoro) Phenyl) methylene] cyclopropane is preferred.
The layer containing the acceptor compound preferably further contains a matrix material. As the matrix material, a wide range of materials for organic EL devices can be used. As the matrix material used together with the acceptor compound, it is preferable to use a donor compound, and it is more preferable to use an aromatic amine compound.

As used herein, the term "derivative" refers to a compound containing the skeleton as the main skeleton, and also includes a compound in which a ring is condensed on the main skeleton and a compound in which substituents on the main skeleton form a ring. For example, a condensed polycyclic aromatic derivative is a compound containing a condensed polycyclic aromatic skeleton as a main skeleton, a compound in which a ring is condensed on the condensed polycyclic aromatic skeleton, and a substituent on the condensed polycyclic aromatic skeleton. It also contains compounds in which rings are formed with each other.

(Hole transport layer)
The hole transport layer is a layer containing a compound having a high hole transport property. Aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used for the hole transport layer, and poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation:: A polymer compound such as PVTPA) can also be used. However, any compound other than these may be used as long as it has a hole transport property higher than an electron transport property.
The hole transport layer may have a single-layer structure or a laminated structure of two or more layers.

式（Ｈ）中、Ｑ_１〜Ｑ_３は、それぞれ、置換もしくは無置換の環形成炭素数６〜５０のアリール基、置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基、又は置換もしくは無置換の環形成炭素数６〜５０のアリール基及び置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基からなる群から選択される２以上の基が単結合を介して結合した基を示す。
アリール基としては、フェニル基、ビフェニル基、ターフェニル基、フルオレニル基、スピロビフルオレニル基、インデノフルオレニル基、ナフチル基、フェナントリル基、アントリル基、トリフェニレニル基等が好ましく、ヘテロアリール基としては、ジベンゾフラニル基、ジベンゾチオフェニル基、カルバゾリル基等が好ましい。アリール基及びヘテロアリール基からなる群から選択される２以上の基が単結合を介して結合した基としては、ジベンゾフラニル基が置換したアリール基、ジベンゾチオフェニル基が置換したアリール基、カルバゾリル基が置換したアリール基等が好ましい。これら置換基はさらに置換基を有してもよい。 The material used for the hole transport layer is preferably a compound represented by the following formula (H).

Wherein _(H), Q 1 ~Q ₃ are each a substituted or unsubstituted ring aryl group having 6 to 50, a substituted or unsubstituted 5 to 50 ring atoms of the heteroaryl group, or a substituted Alternatively, two or more groups selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a heteroaryl group having a substituted or unsubstituted ring-forming atom number of 5 to 50 are bonded via a single bond. Indicates a group.
The aryl group is preferably a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, an indenofluorenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a triphenylenyl group or the like, and a heteroaryl group is preferable. As, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group and the like are preferable. Examples of the group in which two or more groups selected from the group consisting of an aryl group and a heteroaryl group are bonded via a single bond include an aryl group substituted with a dibenzofuranyl group, an aryl group substituted with a dibenzothiophenyl group, and carbazolyl. Aryl groups substituted with groups and the like are preferable. These substituents may further have a substituent.

In one aspect of the present invention, at least one of Q ₁ to Q ₃ in formula (H), preferably substituted by an arylamino group, i.e., a compound represented by the formula (H) is a diamine derivative, It is preferably a triamine derivative or a tetraamine derivative. Examples of the diamine derivative include a tetraaryl-substituted benzidine derivative and TPTE (4,5'-bis [N-phenyl-N- [4'-diphenylamino-1,1'-biphenyl-4-yl] amino] -1,1. '-Biphenyl) and the like are preferably used.

(Light emitting layer)
The light emitting layer is a layer containing a compound (dopant material) having high light emitting property, and various compounds can be used. The light emitting layer usually contains a dopant material and a host material for making it emit light efficiently. For example, as the dopant material, a fluorescent compound or a phosphorescent compound can be used. A fluorescent compound is a compound capable of emitting light from a singlet excited state, and a phosphorescent compound is a compound capable of emitting light from a triplet excited state. The light emitting layer containing a fluorescent compound is called a fluorescent light emitting layer, and the light emitting layer containing a phosphorescent compound is called a phosphorescent light emitting layer. In addition, one light emitting layer may contain a plurality of dopant materials and a plurality of host materials.

式（Ｊ）中、Ｑ_４〜Ｑ_７は、それぞれ、置換もしくは無置換の環形成炭素数６〜５０のアリール基又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリール基を表す。
環形成炭素数６〜５０のアリール基としては、環形成炭素数６〜１２のアリール基が好ましく、フェニル基が特に好ましい。環形成原子数５〜５０のヘテロアリール基としては、カルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基等が挙げられ、ジベンゾフラニル基が好ましい。
Ｑ_８は、置換もしくは無置換の環形成炭素数６〜５０のアリーレン基又は置換もしくは無置換の環形成原子数５〜５０のヘテロアリーレン基を表す。
環形成炭素数６〜５０のアリーレン基としては、ピレニレン基、クリセニレン基、アントラセニレン基、フルオレニレン基等が挙げられ、ピレニレン基が好ましい。環形成炭素数６〜５０のアリーレン基としては、ベンゾフロ縮合骨格を１つ以上有するフルオレニレン基が好ましい。
置換基を有する場合の置換基としては、上記式（１）で挙げた各基が挙げられ、例えば、炭素数１〜６のアルキル基であってもよい。 (Dopant material for light emitting layer)
A wide range of fluorescent compounds can be used as the dopant material for the fluorescent layer. As the dopant material of the fluorescent light emitting layer, a condensed polycyclic aromatic derivative, a styrylamine derivative, a condensed ring amine derivative, a boron-containing compound, a pyrrole derivative, an indole derivative, a carbazole derivative and the like are preferable. More preferably, the dopant material of the fluorescent light emitting layer includes a condensed ring amine derivative and a boron-containing compound. The condensed ring amine derivative is preferably a compound represented by the following formula (J).

Wherein _(J), Q 4 ~Q ₇ each represent a substituted or unsubstituted ring carbon 6 to 50 aryl group or a substituted or unsubstituted 5 to 50 ring atoms of heteroaryl groups.
As the aryl group having 6 to 50 ring-forming carbon atoms, an aryl group having 6 to 12 ring-forming carbon atoms is preferable, and a phenyl group is particularly preferable. Examples of the heteroaryl group having 5 to 50 ring-forming atoms include a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group and the like, and a dibenzofuranyl group is preferable.
Q ₈ represents a substituted or unsubstituted ring carbon 6-50 arylene group or a substituted or unsubstituted 5 to 50 ring atoms heteroarylene group.
Examples of the arylene group having 6 to 50 ring-forming carbon atoms include a pyrenylene group, a chrysenylene group, an anthracenylene group, a fluoreneylene group and the like, and a pyrenylene group is preferable. As the arylene group having 6 to 50 carbon atoms forming a ring, a fluorenylene group having one or more benzoflo condensed skeletons is preferable.
Examples of the substituent when having a substituent include each group listed in the above formula (1), and may be, for example, an alkyl group having 1 to 6 carbon atoms.

Examples of the boron-containing compound include a pyrromethene derivative and a triphenylborane derivative.

Examples of the phosphorescent material (lactone material) that can be used for the phosphorescent layer include metal complexes such as an iridium complex, an osmium complex, and a platinum complex.

式（Ｋ）中、Ｑ_９は、オスミウム、イリジウム、及び白金からなる群から選択される少なくとも１つの金属を示し、ｔは当該金属の価数を示し、ｕは１以上の整数である。環Ｑ_１０は、置換もしくは無置換の環形成炭素数６〜２４のアリール基又は環形成原子数５〜３０のヘテロアリール基を表し、環Ｑ_１１は、窒素を環形成ヘテロ原子として含有する置換もしくは無置換の環形成原子数５〜３０のヘテロアリール基を表す。Ｑ_１２〜Ｑ_１４は水素原子又は置換基である。ｕが２以上のとき、環Ｑ_１０、環Ｑ_１１はそれぞれ同一でも異なってもよい。ｔ−ｕが２以上のとき、Ｑ_１２〜Ｑ_１４はそれぞれ同一でも異なってもよい。 As the metal complex, an orthometalated complex of a metal selected from the group consisting of iridium, osmium, and platinum is preferable, and a complex represented by the following formula (K) is more preferable.

In formula (K), Q ₉ represents at least one metal selected from the group consisting of osmium, iridium, and platinum, t represents the valence of the metal, and u is an integer greater than or equal to 1. Ring Q ₁₀ represents a substituted or unsubstituted aryl group having 6 to 24 ring-forming carbon atoms or a heteroaryl group having 5 to 30 ring-forming atoms, and ring Q ₁₁ is a substitution containing nitrogen as a ring-forming heteroatom. Alternatively, it represents an unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. Q ₁₂ to Q ₁₄ is a hydrogen atom or a substituent. When u is 2 or more, the ring _{Q 10,} ring _{Q 11} may be the same or different. When t-u is 2 or _more, Q 12 _{to Q 14} may be the same or different.

Examples of the aryl group having a ring-forming carbon number of 6 to 24 include those having the carbon number among those listed in the formula (1).
The heteroaryl group having 5 to 30 ring-forming atoms is the same as that given in the formula (1).
Examples of the heteroaryl group having 5 to 30 ring-forming atoms containing nitrogen as a ring-forming heteroatom include those containing nitrogen as a ring-forming heteroatom among the heteroaryl groups listed in the formula (1).
Examples of the substituent when having a substituent include each group listed in the above formula (1).

式（Ｇ）中、Ｑ_９、環Ｑ_１０、環Ｑ_１１、ｔは、式（Ｋ）で定義した通りである。 When tu is zero, the equation (K) is represented by the following equation (G).

In the formula (G), Q ₉ , ring Q ₁₀ , ring Q ₁₁ , and t are as defined in the formula (K).

In addition, tris (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) 3 (Phen)), tris (1,3-diphenyl-1,3-propanedionat) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) 3 (Phen)), Tris [1- (2-tenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) Europium (III) (abbreviation: Eu (abbreviation: Eu) Rare earth metal complexes such as TTA) 3 (Phen)) can be used as a phosphorescent material because they emit light from rare earth metal ions (electron transition between different multiplicities).

式（Ｅ）において、Ａｒ_Ｘ１及びＡｒ_Ｘ２は、それぞれ、置換もしくは無置換の環形成炭素数６〜５０（好ましくは６〜３０）のアリール基、又は置換もしくは無置換の環形成原子数３〜５０（好ましくは５〜３０）のヘテロアリール基を示す。Ａｒ_Ｘ１及びＡｒ_Ｘ２は、それぞれ、置換もしくは無置換のフェニル基、置換もしくは無置換のナフチル基、置換もしくは無置換のビフェニル基、置換もしくは無置換のフェナントリル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のナフトベンゾフラニル基、又は置換もしくは無置換のカルバゾリル基であることがより好ましい。
Ｒ_Ｘ１〜Ｒ_Ｘ８は水素原子又は置換基である。
Ａｒ_Ｘ１及びＡｒ_Ｘ２が置換基を有する場合の置換基、及びＲ_Ｘ１〜Ｒ_Ｘ８の置換基としては、上記式（１）で挙げた各基が挙げられる。 (Host material of light emitting layer)
As the host material used for the fluorescent light emitting layer, a compound having a condensed polycyclic aromatic derivative as a main skeleton is preferable, and anthracene derivative, pyrene derivative, chrysene derivative, naphthacene derivative and the like are more preferable. Particularly suitable hosts as a blue host material (a host material used together with a blue fluorescent light emitting material) and a green host material (a host material used together with a green fluorescent light emitting material) are anthracene derivatives represented by the following formula (E). ..

In the formula (E), Ar _X1 and Ar _X2 are aryl groups having 6 to 50 (preferably 6 to 30) substituted or unsubstituted ring-forming carbon atoms, or 3 to 3 substituted or unsubstituted ring-forming atoms, respectively. It shows 50 (preferably 5-30) heteroaryl groups. Ar _X1 and Ar _X2 are substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted fluorenyl group, substitution, respectively. Alternatively, it is more preferably an unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, or a substituted or unsubstituted carbazolyl group.
R _X1 to R _X8 is hydrogen atom or a substituent.
Examples of the substituent, and substituents _R X1 _{to R X8} when Ar _X1 and _{Ar X2} has a substituent group, include each of the groups listed above formula (1).

The host material used for the phosphorescent layer is preferably a compound having a triplet level higher than that of the phosphorescent dopant, and a phosphorescent host material such as a known aromatic derivative, heterocyclic derivative, or metal complex may be used. it can. As the host material used for the phosphorescent layer, an aromatic derivative and a heterocyclic derivative are preferable. Examples of the aromatic derivative include naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, fluoranthene derivatives and the like. Examples of the heterocyclic derivative include indol derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, dibenzothiophene derivatives and the like.

The host material used together with the phosphorescent material includes a carbazole derivative having a carbazole substituent, a carbazole derivative having a benzo-condensed skeleton, a carbazole derivative having an indeno-condensed skeleton, a carbazole derivative having an indolo-condensed skeleton, and a benzoflo-condensed skeleton. Carbazole derivatives are preferred.

(Electronic transport layer)
The electron transport layer includes metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, heterocyclic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, condensed aromatic hydrocarbon derivatives, and High molecular weight compounds and the like can be used.
Preferably, a nitrogen-containing six-membered ring of an imidazole derivative (for example, benzimidazole derivative, imidazole pyridine derivative, benzimidazole phenanthridin derivative, etc.), an azine derivative (for example, pyrimidine derivative, triazine derivative, quinoline derivative, isoquinolin derivative, phenanthroline derivative, etc.) Examples thereof include compounds containing a structure, and these heterocycles may be substituted with phosphine oxide-based substituents), and aromatic hydrocarbon derivatives (for example, anthracene derivatives, fluorantene derivatives, etc.).

The electron transport layer may have a single layer structure or a laminated structure of two or more layers.
As described above, it is preferable that the electron transport layer contains the compound represented by the formula (1). In this case, the single electron transport layer may contain the compound represented by the formula (1), or the single electron transport layer may contain the compound represented by the formula (1) and other compounds (described above or described later). The compound) may be contained together, or the electron transporting layer containing the compound represented by the formula (1) (first electron transporting layer) and the electron transporting layer containing another compound (second electron transporting layer) are separately provided. It may be provided.

As one of the preferable forms, the electron transport layer is formed of an alkali metal (Li, Cs, etc.), an alkaline earth metal (Mg, etc.), an alloy containing at least two or more of these metals, and a derivative of the alkali metal (for example, 8). -It may contain at least one selected from the group consisting of quinolinolatrithium (Liq)) and derivatives of alkaline earth metals.
When the electron transport layer contains at least one selected from the group consisting of alkali metals, alkaline earth metals and alloys containing at least two or more of these metals, the content ratio in the electron transport layer is not particularly limited. However, it is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.
When the electron transport layer contains at least one selected from the group consisting of an alkali metal derivative and an alkaline earth metal derivative, the content ratio in the electron transport layer is not particularly limited, but is preferably 1 to 99. It is by mass%, more preferably 10 to 90% by mass.

As one of the preferred forms, the second electron transport layer is selected from the group consisting of alkali metals, alkaline earth metals, alloys containing at least two or more of these metals, alkali metal derivatives, and alkaline earth metal derivatives. It is mentioned that at least one kind is included. More preferably, the second electron transport layer contains 8-quinolinola tritium (Liq).
When the second electron transport layer contains at least one selected from the group consisting of alkali metals, alkaline earth metals and alloys containing at least two or more of these metals, the content ratio in the second electron transport layer is Although not particularly limited, it is preferably 0.1 to 50% by mass, more preferably 0.1 to 20% by mass, and further preferably 1 to 10% by mass.
When the second electron transport layer contains at least one selected from the group consisting of an alkali metal derivative and an alkaline earth metal derivative, the content ratio in the second electron transport layer is not particularly limited, but is preferable. , 1-99% by mass, more preferably 10-90% by mass.

The second electron transport layer includes at least one selected from the group consisting of the above-mentioned metal complex, heterocyclic compound, condensed aromatic hydrocarbon derivative and polymer compound, and the above-mentioned alkali metal and alkaline earth metal. Of these, at least one selected from the group consisting of an alloy containing at least two or more metals, an alkali metal derivative, and an alkaline earth metal derivative may be used in combination.

Further, the second electron transport layer may be composed of only 8-quinolinola tritium (Liq).

(Electron injection layer)
The electron injection layer is a layer containing a material having high electron injection properties. The electron injection layer includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. Alkali metals, alkaline earth metals, or compounds thereof (8-quinolinolatrithium (Liq), etc.) can be used.
In addition to the above, a material having electron transportability containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq or the like may be used. .. In this case, electron injection from the cathode can be performed more efficiently.

A composite material formed by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injection property and electron transport property because the organic compound receives electrons from the electron donor.
The organic compound is preferably a material excellent in transporting received electrons, and specifically, for example, a material (metal complex, complex aromatic compound, etc.) constituting the above-mentioned electron transport layer can be used. .. The electron donor may be any material that exhibits electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium and the like can be mentioned. Further, alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxides, calcium oxides, barium oxides and the like can be mentioned. A Lewis base such as magnesium oxide can also be used. Further, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

(cathode)
As the cathode, it is preferable to use a metal having a small work function (specifically, 3.8 eV or less), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements, that is, alkali metals such as lithium (Li) and cesium (Cs), magnesium (Mg), and calcium (Mg). Examples thereof include alkaline earth metals such as Ca) and strontium (Sr), and rare earth metals such as alloys containing them (for example, MgAg and AlLi), europium (Eu) and ytterbium (Yb), and alloys containing these.

When forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum vapor deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method, an inkjet method or the like can be used.

By providing the electron injection layer, a cathode is formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium tin oxide containing silicon oxide, regardless of the size of the work function. be able to. These conductive materials can be formed into a film by using a sputtering method, an inkjet method, a spin coating method, or the like.

(Insulation layer)
Since the organic EL element applies an electric field to the ultrathin film, pixel defects due to leaks and short circuits are likely to occur. In order to prevent this, an insulating layer made of an insulating thin film layer may be inserted between the pair of electrodes.
Materials used for the insulating layer include, for example, aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide. , Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide and the like. These mixtures and laminates may be used.

(Space layer)
The space layer is, for example, a fluorescent light emitting layer for the purpose of preventing the exciters generated in the phosphorescent light emitting layer from diffusing into the fluorescent light emitting layer or adjusting the carrier balance when the fluorescent light emitting layer and the phosphorescent light emitting layer are laminated. It is a layer provided between the phosphorescent layer and the phosphorescent layer. Further, the space layer can be provided between a plurality of phosphorescent light emitting layers.
Since the space layer is provided between the light emitting layers, it is preferable that the space layer is a material having both electron transport property and hole transport property. Further, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials used for the hole transport layer described above.

(Blocking layer)
A blocking layer such as an electron blocking layer, a hole blocking layer, or a triplet blocking layer may be provided in a portion adjacent to the light emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transporting layer, and the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to the electron transporting layer. The triplet blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing into surrounding layers and confining excitons in the light emitting layer.

Each layer of the above-mentioned organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, a vapor deposition method such as a vacuum vapor deposition method or a molecular beam vapor deposition method (MBE method), or a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, etc. using a solution of a compound forming a layer. It can be formed by a known method according to the coating method of.

The film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if the film thickness is too thick, a high driving voltage is required and efficiency deteriorates. Therefore, the film thickness is usually 1 nm to 10 μm. It may be 5 nm to 10 μm or 10 nm to 0.2 μm.

[Electronics]
The organic EL element according to one aspect of the present invention can be used for display parts such as organic EL panel modules, display devices such as televisions, mobile phones and personal computers, and electronic devices such as lighting and light emitting devices for vehicle lamps. ..

Example 1 (Synthesis of Compound 1)

2-Bromofluorantene (5.00 g, 17.8 mmol), [4- (2-phenylbenzimidazol-1-yl) phenyl] boric acid (6.16 g, 19.6 mmol), palladium acetate under an argon atmosphere. (0.160 g, 0.712 mmol), XPhos (2-dicyclohexylphosphino-2', 4', 6'-triisopropyl-1,1'-biphenyl) (0.678 g, 1.42 mmol), cesium carbonate (0.678 g, 1.42 mmol) A mixture of 11.6 g, 35.6 mmol) and 1,4-dioxane (70 mL) was stirred at 90 ° C. for 8 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give compound 1 (5.95 g, 71% yield). As a result of mass spectrometry of the compound, m / e = 470, so the compound was identified as Compound 1 (Exactmass: 470.18).

Synthesis Example 1 (Synthesis of Intermediate 1)

Under an argon atmosphere, 2-bromofluorantene (10.0 g, 35.6 mmol), (3-chlorophenyl) boronic acid (5.56 g, 35.6 mmol), (AMPHOS) ₂ PdCl ₂ (1.64 g, 1. A mixture of 42 mmol), 2M aqueous sodium carbonate solution (53.4 mL, 107 mmol) and toluene (150 mL) was stirred at 75 ° C. for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, the organic layer was extracted, and the solvent was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to obtain Intermediate 1 (11.1 g, 100% yield).
AMPHOS represents [4- (N, N-dimethylamino) phenyl] di-tert-butylphosphine.

Example 2 (Synthesis of Compound 2)

Under an argon atmosphere, intermediate 1 (1.00 g, 3.20 mmol), [4- (2-phenylbenzimidazol-1-yl) phenyl] boric acid (1.11 g, 3.52 mmol), palladium acetate (0. A mixture of 029 g, 0.128 mmol), XPhos (0.122 g, 0.256 mmol), cesium carbonate (2.08 g, 6.39 mmol) and 1,4-dioxane (13 mL) was stirred at 90 ° C. for 20 hours. After completion of the reaction, the mixture was cooled to room temperature and the solvent was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give compound 2 (1.05 g, 60% yield). As a result of mass spectrometry of the compound, m / e = 546, so the compound was identified as compound 2 (Exactmass: 546.21).

Example 3 (Manufacturing and evaluation of organic EL element)
A glass substrate (manufactured by Geomatic) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The film thickness of the ITO transparent electrode was 130 nm.
The glass substrate with the transparent electrode line after cleaning is attached to the substrate holder of the vacuum vapor deposition apparatus, and the compound HI-1 is first vapor-deposited on the surface on the side where the transparent electrode line is formed so as to cover the transparent electrode. A compound HI-1 film having a thickness of 5 nm was formed. The HI-1 membrane functions as a hole injection layer.
Following the film formation of the HI-1 film, the compound HT-1 was deposited to form an HT-1 film having a film thickness of 85 nm on the HI-1 film. The HT-1 membrane functions as a first hole transport layer.
Following the film formation of the HT-1 film, the compound HT-2 was deposited to form an HT-2 film having a film thickness of 15 nm on the HT-1 film. The HT-2 membrane functions as a second hole transport layer.
BH-1 (host material) and BD-1 (dopant material) are co-deposited on the HT-2 film so that the proportion (mass ratio) of BD-1 is 4%, and a light emitting layer having a film thickness of 25 nm is formed. A film was formed.
Compound 1 was deposited on the light emitting layer to form an electron transport layer having a film thickness of 20 nm. LiF was vapor-deposited on the electron transport layer to form a LiF film having a film thickness of 1 nm. Metal Al was vapor-deposited on the LiF film to form a metal cathode having a film thickness of 80 nm.
The organic EL element was manufactured as described above. The compounds used are shown below.

The drive voltage, external quantum efficiency (EQE), and device life (LT90) of the obtained organic EL device were measured as follows. The results are shown in Table 1.

(Drive voltage)
The voltage (unit: V) when energized between the ITO transparent electrode and the Al cathode was measured so that the current density was 10 mA / cm ^{2, and used as the drive voltage.}

(External Quantum Efficiency (EQE))
The spectral radiance spectrum when a voltage was applied to the element so that the current density was 10 mA / cm ² was measured with a spectral radiance meter (“CS-1000” manufactured by Konica Minolta Co., Ltd.). From the obtained spectral radiance spectrum, it was assumed that Lambasian radiation was performed, and the external quantum efficiency EQE (unit:%) was calculated.

(Element life)
A direct current continuous energization test is performed with the initial current density set to 50 mA / cm ² , and the time during which the brightness decreases to 90% of the brightness at the start of the test is measured, and the measured time is used as the life LT90 (lifetime LT90). The unit: time (h)).

Example 4 and Comparative Examples 1-5
In the electron transport layer, an organic EL device was produced and evaluated in the same manner as in Example 3 except that the compounds shown in Table 1 were used instead of the compound 1. The results are shown in Table 1.
The compounds used are shown below.

From Table 1, it can be seen that the organic EL device using the compound according to one aspect of the present invention has a long life.

Claims (22)

A compound represented by the following formula (1).

(In formula (1), A and R 1 to R 13 are hydrogen atom, halogen atom, hydroxy group, cyano group, substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, substituted or unsubstituted carbon, respectively. An alkenyl group of number 2 to 25, a substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, a substituted or unsubstituted ring-forming group having 3 to 25 carbon atoms, a substituted or unsubstituted ring-forming group having 1 to 25 carbon atoms. Alkoxy groups, substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 31 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms, Substituted or unsubstituted ring-forming aryloxy groups with 6 to 30 carbon atoms, substituted or unsubstituted ring-forming atomics with 5 to 30 heteroaryloxy groups, substituted or unsubstituted alkylthio groups with 1 to 25 carbon atoms, substituted or unsubstituted ring formation arylthio group having 6 to 30 carbon atoms, a substituted or unsubstituted ring atoms 5-30 heteroarylthio groups, group (Z 7 represented by -SiZ 7 3 are each hydrogen atom, an alkyl group having 1 to 25 carbon atoms, a heteroaryl group ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5-30,), -, a group represented by BZ 8 2 (Z 8 are each a hydrogen atom, an alkyl group, ring-forming aryl group having 6 to 30 carbon atoms or heteroaryl group having ring atoms of 5 to 30, 1 to 25 carbon atoms), - represented by NZ 9 2 (Z 9 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms, respectively),-( C = O) group (Z 10 represented by Z 10 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms or heteroaryl ring atoms 5 to 30, a group), or -P (= O) Z 11 2, a group represented by (Z 11 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms, Alternatively, it is a heteroaryl group having 5 to 30 ring-forming atoms).
Any two of R 1 to R 4 may be combined with each other to form a ring. Any two of R 5 to R 13 may be combined with each other to form a ring.
L is an arylene group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms or a heteroarylene group having 5 to 30 substituted or unsubstituted ring-forming atoms.
n is an integer from 0 to 3. When n is 0, (L) n is a single bond. When n is 2 or more, the plurality of Ls may be the same or different. ) The compound according to claim 1, wherein n is an integer of 1 to 3. The compound according to claim 1 or 2, wherein L is a substituted or unsubstituted ring-forming arylene group having 6 to 30 carbon atoms. The compound according to any one of claims 1 to 3, wherein L is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group. A is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms. The compound according to any one of claims 1 to 4. The compound according to any one of claims 1 to 5, wherein A is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms or a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms. R 1 to R 13 are hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 25 carbon atoms, substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted ring formation, respectively. The compound according to any one of claims 1 to 6, which is a heteroaryl group having 5 to 30 atoms. The compound according to any one of claims 1 to 7, wherein R 5 to R 9 are hydrogen atoms. The compound according to any one of claims 1 to 8, wherein R 5 to R 13 are hydrogen atoms. The compound according to any one of claims 1 to 9, wherein R 1 to R 13 are hydrogen atoms. The compound according to any one of claims 1 to 10, wherein any two of R 1 to R 4 do not bond with each other to form a ring, and any two of R 5 to R 13 do not bond with each other to form a ring. .. The compound according to claim 1, which is represented by the following formula (10).

(In the formula (10), A and R ^{1 to} R ¹³ are the same as the above formula (1). M is an integer of 1 to 3. When m is 2 or more, the structure of the plurality of phenylene groups is , Each may be the same or different.) The compound according to claim 12, which is represented by the following formula (11).

(In the formula (11), A and R ^{1 to} R ¹³ are the same as the above formula (10).) The compound according to claim 12, which is represented by the following formula (12).

(In the formula (12), A and R ^{1 to} R ¹³ are the same as the above formula (10).) The compound according to claim 1, which is represented by the following formula (20).

(In the formula (20), R 1 to R 13 , L and n are the same as those in the formula (1).
R 14 to R 18 are hydrogen atom, halogen atom, cyano group, substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, substituted or unsubstituted, respectively. Alkinyl group having 2 to 25 carbon atoms, substituted or unsubstituted ring-forming carbon number 3 to 25 cycloalkyl group, substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, substituted or unsubstituted ring-forming carbon number 6 to 30 aryl groups, substituted or unsubstituted aralkyl groups having 7 to 31 carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring-forming atoms, substituted or unsubstituted ring-forming carbon atoms 6 to 30 Aryloxy groups, substituted or unsubstituted heteroaryloxy groups having 5 to 30 ring-forming atoms, substituted or unsubstituted alkylthio groups having 1 to 25 carbon atoms, substituted or unsubstituted ring-forming carbon atoms of 6 to 30 arylthio group, a substituted or unsubstituted ring atoms 5-30 heteroarylthio groups, group (Z 7 represented by -SiZ 7 3 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, the ring forming an aryl group having 6 to 30 carbon atoms, or a heteroaryl group ring atoms 5-30) - group (Z 8 represented by BZ 8 2 are each a hydrogen atom, a carbon number 1 to 25 alkyl group, a heteroaryl group ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5-30,), -, a group represented by NZ 9 2 (Z 9 are each a hydrogen atom, An alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms), and a group represented by − (C = O) Z 10 ( Z 10 is a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, or a heteroaryl group having 5 to 30 ring-forming atoms), or −P (= O). group (Z 11 represented by Z 11 2 are each a hydrogen atom, an alkyl group having 1 to 25 carbon atoms, ring-forming aryl group having 6 to 30 carbon atoms or a ring atoms 5 to 30 heteroaryl group, Is). ) The compound according to claim 15, which is represented by the following formula (30).

(In the formula (30), R ^{1 to} R ¹⁸ are the same as the above formula (20).
m is an integer of 1-3. When m is 2 or more, the structures of the plurality of phenylene groups may be the same or different. ) The compound according to any one of claims 1 to 16, which is a material for an organic electroluminescence device. In an organic electroluminescence device in which at least one or more organic thin film layers including a light emitting layer are sandwiched between a cathode and an anode, at least one layer of the organic thin film layer is the compound according to any one of claims 1 to 17. Contains organic electroluminescence device. 18. Claim 18 having an electron transport band between the light emitting layer and the cathode, and at least one layer of the organic thin film layer included in the electron transport band contains the compound according to any one of claims 1 to 17. The organic electroluminescence device described in 1. The organic electroluminescence device according to claim 19, wherein the organic thin film layer containing the compound is an electron transport layer. The electron transport layer is further composed of alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth metal halide, and rare earth metal. Claim 20 containing one or more selected from the group consisting of oxides, halides of rare earth metals, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals. The organic electroluminescence element described in 1. An electronic device equipped with the organic electroluminescence element according to any one of claims 18 to 21.