JP2013177386A - Aromatic amine derivative, organic electroluminescent element, and electronic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic EL element with high efficiency and long life; an electronic device carrying the element; and a compound capable of providing such an organic EL element.SOLUTION: This compound is represented by formula (1). In the formula: Land Lare each a single bond, or a substituted or unsubstituted arylene group; Rand Rare each a hydrogen atom, an alkyl group, or an aryl group; and at least one of Ar-Aris a terphenyl group while the others are each independently a substituted or unsubstituted aryl group. When the compound is used as a hole transport material for an organic EL element wherein an acceptor layer is connected to an anode, a hole injection amount from the acceptor layer to the hole transport layer is increased and an effect is further improved.

Description

  The present invention relates to an aromatic amine derivative and an organic electroluminescence device (organic EL device) using the same. The present invention further relates to an electronic device equipped with the organic EL element.

  An organic EL element is a self-luminous element utilizing the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. Eastman Kodak's C.I. W. Organic materials have been constructed since Tang et al. Reported low-voltage driven organic EL devices using stacked devices (CW Tang, SA Vanslyke, Applied Physics Letters, 51, 913, 1987, etc.) Research on organic EL elements as materials has been actively conducted.

For example, Patent Literatures 1 to 4 disclose a diamine compound of central fluorene and use it as a hole transport layer adjacent to the light emitting layer, thereby improving stability and durability as compared with a diamine compound having a terminal phenyl group. Disclosed is an organic EL device.
Further, Patent Document 5 uses a compound having a specific diamine structure as a first hole transport material, and uses an aromatic amine derivative having a dibenzofuran structure and a carbazole structure as a second hole transport material to reduce the driving voltage. Discloses that an organic EL element having a long lifetime can be manufactured. Patent Document 6 employs a specific diphenyl-centered diamine compound in the first hole transport layer, and employs an amine compound having a specific heteroaryl structure in the second hole transport layer in the phosphorescent organic EL device. Thus, it is disclosed to solve the problem of the hole transport layer having electron block property, electron resistance and hole transport property. Patent Document 7 provides an organic EL device having high light emission efficiency and low driving voltage by employing a compound having a carbazole ring structure in a hole transport layer adjacent to the light emitting layer.
That is, in an organic EL element, particularly a phosphorescent element, the hole transport layer is composed of a first hole transport layer and a second hole transport layer, and a high-functional material is applied to the second hole transport layer. The device performance is improved.
The performance required for the second hole transport layer is high triplet energy (preferably 2.6 eV or more) to prevent diffusion of excitation energy of the phosphorescent light emitting layer, and electron resistance, light emitting layer because it is adjacent to the light emitting layer. In order to prevent electrons from leaking, the organic layer has a low affinity (preferably 2.4 eV or less), and a large ionization potential (5.5 eV or more is preferable) in order to promote hole injection into the light emitting layer. ) It is required to be an organic layer. As a material satisfying such characteristics, a molecular skeleton having high electron resistance in which a heteroaryl ring such as carbazole or dibenzofuran is bonded to a triphenylamine skeleton is preferred.

On the other hand, the first hole transport layer is generally required to have excellent hole injectability into the second hole transport layer.
Further, from the viewpoint of improving the hole injection property, it has been studied to contain a compound having p-type semiconductor properties (also referred to as an acceptor material or an electron accepting compound in the present invention) as the hole injection layer ( (See Patent Documents 8 to 9).

Japanese Patent No. 3813003 Japanese Patent No. 3801330 Japanese Patent No. 3792029 Japanese Patent No. 3,835,917 International Publication No. 2010/114017 International Publication No. 2009/041635 International Publication No. 2011/024451 International Publication No. 01/49806 (Special Table No. 2003-519432) International Publication No. 2011/090149

As research and development of the organic EL element as described above proceeds, it is indispensable for commercial devices to efficiently extract the light emitted internally for each emission color of the organic EL element. Therefore, it is necessary to adjust the optical path length of the entire device by controlling the film thickness of the hole transport layer having higher carrier transportability than other organic layers. At this time, there is a demand for a hole transport material having such a high mobility that the driving voltage does not increase even when the hole transport layer is thickened, and a large amount of carriers is generated due to the interaction with the acceptor material. There is a need to apply a hole transport material to the first hole transport layer.
The present invention has been made to solve the above-described problems, and provides an organic EL element with high efficiency and a long lifetime, an electronic device equipped with the organic EL element, and such an organic EL element. It is an object of the present invention to provide such a compound.

  As a result of intensive studies to develop an aromatic amine derivative having the above-mentioned preferable properties and an organic EL device using the same, the present inventors have used a compound represented by the general formula (1). We found that the problem could be solved. The present invention has been completed based on such findings.

［式中、Ｌ¹及びＬ²は、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数６〜１０のアリーレン基である。
Ｒ¹及びＲ²は、それぞれ独立に、水素原子、炭素数１〜１０のアルキル基又は環形成炭素数６〜３０のアリール基である。
Ａｒ¹〜Ａｒ⁴は、少なくとも１つが下記一般式（２）で表される基であり、そうでないものは、それぞれ独立に、置換もしくは無置換の環形成炭素数６〜３０のアリール基である。

（Ｒ³〜Ｒ⁵は、それぞれ独立に、炭素数１〜１０のアルキル基、環形成炭素数３〜１０のシクロアルキル基、炭素数１〜１０のアルコキシ基、炭素数７〜３０のアラルキル基、炭素数６〜３０のアリールオキシ基、環形成炭素数６〜３０のアリール基、ハロゲン原子又はシアノ基である。Ｒ³〜Ｒ⁵は、互いに結合して炭化水素環を形成してもよい。
ａ及びｂは、それぞれ独立に、０〜４の整数である。ｃは、０〜５の整数である。また、ａ、ｂ又はｃが２以上である場合、隣接するＲ³同士、隣接するＲ⁴同士又は隣接するＲ⁵同士は、互いに結合して炭化水素環を形成してもよい。）］ That is, one embodiment of the present invention provides a compound represented by the following general formula (1).

[Wherein, L ¹ and L ² are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
R ¹ and R ² are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms.
Ar ^{1 to} Ar ⁴ are at least one group represented by the following general formula (2), and the others are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. .

(R ^{3 to} R ⁵ are each independently an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. , An aryloxy group having 6 to 30 carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a halogen atom or a cyano group, R ^{3 to} R ⁵ may be bonded to each other to form a hydrocarbon ring. .
a and b are each independently an integer of 0 to 4; c is an integer of 0-5. When a, b or c is 2 or more, adjacent R ^{3 s} , adjacent R ^{4 s} or adjacent R ^{5 s} may be bonded to each other to form a hydrocarbon ring. ]]

In another aspect of the present invention, in an organic EL device in which a single organic layer or a plurality of organic thin film layers containing at least a light emitting layer is sandwiched between a cathode and an anode, at least one of the organic thin film layers is An organic EL device containing the compound represented by the general formula (1) alone or as a component of a mixture is provided.
Furthermore, another aspect of the present invention provides an electronic device equipped with the organic EL element.

The compound of the present invention is a high mobility hole transport material in which the driving voltage does not increase even when the hole transport layer of the organic EL element is thickened, and the optical path length of the organic EL element can be adjusted. It is possible to provide an organic EL element capable of improving the efficiency and extending the life.
In particular, when used as a hole transport material of an organic EL device having an acceptor layer bonded to an anode, the compatibility with the acceptor material is excellent, so that the amount of holes injected from the acceptor layer to the hole transport layer increases, The effect can be further enhanced.

In the present specification, it is possible to arbitrarily select a prescription that is preferable, and it can be said that a combination of prescriptions that are preferable is more preferable.
The compound of the present invention is represented by the following general formula (1).

In Formula (1), L ¹ and L ² are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
Examples of the arylene group include a phenylene group and a naphthylene group. The arylene group may have a substituent. Examples of the substituent include a methyl group, an ethyl group, various propyl groups (“various” indicates that all linear and branched groups are included, and the same shall apply hereinafter), and various butyl groups. An alkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms), such as a methoxy group, an ethoxy group, various propoxy groups, and various butoxy groups. Alkoxy group; fluorine atom and the like.
L ¹ and L ² are each preferably a single bond or an arylene group having 6 to 10 ring carbon atoms, one of which is a single bond and the other is substituted or unsubstituted.

In Formula (1), R ¹ and R ² are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms.
Examples of the alkyl group include a methyl group, an ethyl group, various propyl groups, various butyl groups, various octyl groups, and various decyl groups. Preferably carbon number of an alkyl group is 1-5.
Examples of the aryl group include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, and an anthryl group. The number of ring-forming carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12, Preferably it is 6-10.
R ¹ and R ² are preferably a hydrogen atom, a methyl group or a phenyl group, and more preferably a methyl group.

In formula (1), Ar ^{1 to} Ar ⁴ are at least one group represented by the following general formula (2) (preferably a group represented by the following general formula (3) or (4)), What is not so is each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms (excluding a terphenylyl group).

In formulas (2) to (4), R ^{3 to} R ⁵ are each independently an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. , An aralkyl group having 7 to 30 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a halogen atom, or a cyano group. R ^{3 to} R ⁵ may be bonded to each other to form a hydrocarbon ring.
Examples of the alkyl group and aryl group are the same as those for R ¹ and R ² , and preferred ones are also the same. Examples of the alkoxy group include a methoxy group, an ethoxy group, and a propoxy group, and an alkoxy group having 1 to 5 carbon atoms is preferable.
Examples of the cycloalkyl group include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and the like. The number of ring-forming carbon atoms of the cycloalkyl group is preferably 5-8.
The aralkyl group is preferably an alkylene group having 1 to 3 carbon atoms substituted with the aryl group, more preferably a methylene group substituted with the aryl group. Examples of the aryl group mentioned here are the same as those for R ¹ and R ² . The carbon number (total carbon number) of the aralkyl group is preferably 7 to 15, more preferably 7 to 11. The aryl group in the aralkyl group is preferably a phenyl group.
Examples of the aryl group in the aryloxy group are the same as those for R ¹ and R ² , and preferred ones are also the same. The ring-forming carbon number of the aryloxy group is preferably 6-20, more preferably 6-12, and still more preferably 6-10.
Examples of the halogen atom include a fluorine atom, and a fluorine atom is preferable.
When R ^{3 to} R ⁵ are bonded to each other to form a hydrocarbon ring, for example, R ³ and R ⁴ , or R ⁴ and R ⁵ are bonded to each other to form a hydrocarbon ring, the carbon Examples of the hydrogen ring include a fluorene ring. R ^{3 to} R ⁵ are preferably not bonded to each other.

In formulas (2) to (4), a and b are each independently an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. c is an integer of 0 to 5, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, still more preferably 0 or 1, and particularly preferably 0.
When a, b or c is 2 or more, adjacent R ^{3 s} , adjacent R ^{4 s} or adjacent R ^{5 s} may be bonded to each other to form a hydrocarbon ring. Examples of the hydrocarbon ring thus formed include a naphthalene ring.

As described above, Ar ^{1 to} Ar ⁴ which are not groups represented by the general formula (2) (also not groups represented by the general formulas (3) and (4)) are substituted or absent. A substituted aryl group having 6 to 30 ring carbon atoms (excluding terphenylyl group). Examples of the aryl group include a phenyl group, a biphenylyl group, a naphthyl group, an anthryl group, an aryl group having 6 to 20 ring carbon atoms is preferable, and an aryl group having 6 to 12 ring carbon atoms is more preferable. And a biphenylyl group are more preferred.
Examples of the substituent that the aryl group may have include, for example, a carbazolyl group (for example, 9-carbazolyl group, 9-phenyl-1-carbazolyl group, 9-phenyl-2-carbazolyl group, 9-phenyl-3). -Carbazolyl group, 9-phenyl-4-carbazolyl group, etc.), thiophenyl group, phenylthiophenyl group, benzothiophenyl group, dibenzothiophenyl group, furanyl group, phenylfuranyl group, benzofuranyl group, dibenzofuranyl group, etc. A heterocyclic group having 5 to 30 (preferably 5 to 20) ring-forming atoms is exemplified.

As the compound represented by the general formula (1), the following are preferable.
[I] A compound in which Ar ¹ and Ar ² are a group represented by the general formula (2).
[Ii] A compound in which Ar ¹ and Ar ³ are a group represented by the general formula (2).
[Iii] Compounds in which three or more of Ar ^{1 to} Ar ⁴ are different from each other.
[Iv] A compound in which three or more of Ar ^{1 to} Ar ⁴ are the same.
When the molecular structure of the compound represented by the general formula (1) is asymmetric, it is assumed that the amorphous property increases in the thin film, the crystallization of the thin film is suppressed, and the thin film stability is improved. When the organic EL element material is used for a thick film layer, the thin film stability is particularly important from the viewpoint of suppressing crystallization of the thin film. The compound of the present invention is often used in a thick hole transport layer for optical adjustment of an organic EL device, and an asymmetric structure is preferred from the viewpoint of thin film stability.
In addition, there is no restriction | limiting in particular in the manufacturing method of the compound of this invention, With reference to an Example, it can manufacture by a well-known method.

  Specific examples of the compound represented by the general formula (1) of the present invention are shown below, but are not limited to these exemplified compounds.

[Organic electroluminescence device]
Next, an embodiment of the organic electroluminescence element (organic EL element) of the present invention will be described.
The organic EL device of the present invention is an organic electroluminescence device having an organic thin film layer between an anode and a cathode facing each other, and includes one organic thin film layer containing the compound represented by the general formula (1). It has the above.
Among them, in particular, the organic EL device of the present invention is an organic EL device having at least two or more hole transport layers and a light emitting layer in sequence between an opposing anode and cathode, and among the hole transport layers, One of them contains the compound represented by the general formula (1), and is not adjacent to the light emitting layer.
For example, the at least two or more hole transport layers include a first hole transport layer on the anode side and a second hole transport layer on the light-emitting layer side, and the first hole transport layer has the general formula (1). It is preferable to contain the compound represented by these.
As described above, the present invention provides a hole transport material comprising a plurality of hole transport layers, wherein the hole transport layer not adjacent to the light emitting layer is a compound having a high mobility represented by the general formula (1). As a result, the driving voltage does not increase even if the hole transport layer is made thicker, the optical path length of the organic EL element can be adjusted, and the efficiency and life of the element can be increased. Also, it is compatible with acceptor materials with excellent hole-injecting properties, and by increasing the amount of carriers generated, more holes can be transported and injected into the light-emitting layer, leading to higher device efficiency. .

The organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit. A tandem type having a plurality of light emitting units may be used. Here, the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.
Hereinafter, the element structure of the organic EL element of the present invention will be described.
(1) Structure of organic EL element As a typical element structure of the organic EL element of the present invention,
(1) Anode / acceptor material-containing layer (acceptor layer) / first hole transport layer / second hole transport layer / light emitting layer / cathode
(2) Anode / acceptor material-containing layer (acceptor layer) / first hole transport layer / second hole transport layer / light emitting layer / electron injection layer / cathode
(3) Anode / acceptor material-containing layer (acceptor layer) / first hole transport layer / second hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(4) Anode / first hole transport layer / second hole transport layer / light emitting layer / electron injection layer / cathode
(5) Structures such as anode / first hole transport layer / second hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode can be mentioned.
Between the second hole transport layer and the light emitting layer, there may be further third, fourth,... Hole transport layers. Further, an electron barrier layer or an exciton barrier layer may be provided between the light emitting layer and the hole transport layer, and the hole transport layer in contact with the light emitting layer may be an electron barrier layer or an exciton barrier layer. .
Note that in the hole transport layer adjacent to the acceptor layer, for example, in the element configuration described in the above (1) to (3), the first hole transport layer adjacent to the acceptor layer is the acceptor layer adjacent hole transport layer. Sometimes called.

The organic EL device of the present invention preferably has an acceptor layer containing an acceptor material between the anode and the at least two or more hole transport layers.
Moreover, the positive hole transport layer containing the compound represented by the said General formula (1) may contain acceptor material.
As the acceptor material, since the bonding property with the hole transport layer containing the compound represented by the general formula (1) is improved and the device performance can be further improved, the following general formulas (A), ( A compound having a highly planar skeleton such as a compound represented by B) or (C) is preferable.

(In Formula (A), R ^{11 to} R ¹⁶ are each independently a cyano group, —CONH ₂ , a carboxyl group, or —COOR ¹⁷ (R ¹⁷ is an alkyl group having 1 to 20 carbon atoms). R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , or R ¹⁵ and R ¹⁶ are bonded to each other to represent a group represented by —CO—O—CO—.
Examples of the alkyl group for R ¹⁷ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.

｛式中、Ｘ¹及びＸ²は互いに同一でも異なっていてもよく、下記（ａ）〜（ｇ）に示す二価の基のいずれかである。 In the formula (B), R ^{21 to} R ²⁴ may be the same or different from each other, and are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring forming carbon number. 6-50 aryl group, substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, halogen atom, substituted or unsubstituted fluoroalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted 1 carbon atom An alkoxy group having 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group. R ^{21 to} R ²⁴ that are adjacent to each other may be bonded to each other to form a ring.
Y ^{1 to} Y ⁴ may be the same as or different from each other, and are —N═, —CH═, or C (R ²⁵ ) ═, and R ²⁵ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a halogen atom, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms , A substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group.
Ar ¹⁰ is a condensed ring having 6 to 24 ring carbon atoms or a heterocyclic ring having 6 to 24 ring atoms. ar ¹ and ar ² each independently represent a ring of the following general formula (i) or (ii).

{Wherein X ¹ and X ² may be the same or different from each other and are any of the divalent groups shown in the following (a) to (g).

（式中、Ｒ³¹〜Ｒ³⁴は、それぞれ互いに同一でも異なっていてもよく、水素原子、置換もしくは無置換の炭素数１〜２０のアルキル基、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の複素環基であり、Ｒ³²とＲ³³は互いに結合して環を形成してもよい。）｝

(Wherein R ^{31 to} R ³⁴ may be the same as or different from each other, and are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring forming carbon number of 6 to 50). Or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ³² and R ³³ may be bonded to each other to form a ring.)}

Examples of each group of R ^{21 to} R ²⁴ and R ^{31 to} R ³⁴ are as follows.
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
Examples of the aryl group include a phenyl group, a biphenyl group, and a naphthyl group.
Examples of the heterocyclic group include residues such as pyridine, pyrazine, furan, imidazole, benzimidazole, and thiophene.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
Examples of the alkoxy group include a methoxy group and an ethoxy group.
Examples of the aryloxy group include a phenyloxy group.
These may have a substituent, and as the substituted aryl group, an aryl group substituted with a halogen atom such as a monofluorophenyl group or a trifluoromethylphenyl group; a tolyl group, a 4-t-butylphenyl group And an aryl group substituted with an alkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms). Examples of the substituted alkyl group include alkyl groups substituted with a halogen atom, such as a trifluoromethyl group, a pentafluoroethyl group, a perfluorocyclohexyl group, and a perfluoroadamantyl group. As the substituted aryloxy group, an aryloxy group substituted with a halogen atom or substituted with a halogen atom-containing alkyl group (having 1 to 5 carbon atoms), such as 4-trifluoromethylphenyloxy group and pentafluorophenyloxy; Examples thereof include an aryloxy group substituted with an alkyl group having 1 to 10 carbon atoms (preferably 1 to 5 carbon atoms) such as a 4-t-butylphenoxy group.
R ^{21 to} R ²⁴ that are adjacent to each other may be bonded to each other to form a ring. Examples of the ring include a benzene ring, naphthalene ring, pyrazine ring, pyridine ring, furan ring and the like.

式（Ｃ）中、Ｚ¹〜Ｚ³は、それぞれ独立に、下記一般式（ｈ）で示される二価の基である。

式（ｈ）中、Ａｒ³¹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、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である。
アリール基としては、フェニル基、ナフチル基等が挙げられる。
ヘテロアリール基としては、ピリジン、ピラジン、ピリミジン、キノリン、イソキノリン等が挙げられる。
また、これらの置換基の例としては、シアノ基、フルオロ基、トリフルオロメチル基、クロロ基およびブロモ基等の電子吸引性の基が挙げられる。

In the formula (C), Z ^{1 to} Z ³ are each independently a divalent group represented by the following general formula (h).

In the formula (h), Ar ³¹ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
Examples of the aryl group include a phenyl group and a naphthyl group.
Examples of the heteroaryl group include pyridine, pyrazine, pyrimidine, quinoline, isoquinoline and the like.
Examples of these substituents include electron withdrawing groups such as a cyano group, a fluoro group, a trifluoromethyl group, a chloro group, and a bromo group.

(2) Translucent board | substrate The organic EL element of this invention is produced on a translucent board | substrate. Here, the translucent substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 to 700 nm of 50% or more.
Specifically, a glass plate, a polymer plate, etc. are mentioned. Examples of the glass plate include soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz. Examples of the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.

(3) Anode The anode of the organic EL device of the present invention has a function of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more. Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), indium-zinc oxide (IZO), gold, silver, platinum, copper and the like.
The anode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering.
Thus, when light emission from the light emitting layer is taken out from the anode, it is preferable that the transmittance of the anode for light emission is greater than 10%. The sheet resistance of the anode is preferably several hundred Ω / □ or less. Although the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 μm, preferably 10 to 200 nm.

(4) Hole transport layer As described above, at least two or more hole transport layers are used in the organic EL element in a more preferred embodiment of the organic EL element of the present invention.
The hole transport layer not adjacent to the light emitting layer is often used in a thick film for optical adjustment of the organic EL element, and is required to have a high hole mobility from the viewpoint of lowering the voltage. Furthermore, in order to generate | occur | produce a carrier efficiently, it is often laminated | stacked with an acceptor layer, and it is required that interaction with an acceptor layer is high.
Since the compound represented by the general formula (1) has a fluorene structure, the molecule has higher planarity than the biphenyl structure, and thus has a high hole mobility. Furthermore, since the amount of carriers generated is large because of generally excellent interaction with an acceptor material having high planarity, more holes can be transported and injected into the light emitting layer. That is, it satisfies the characteristics required for a hole transport layer that is not adjacent to the light emitting layer (in the case where there are two hole transport layers, it corresponds to the first hole transport layer).
On the other hand, the characteristics required for the hole transport layer adjacent to the light-emitting layer (when there are two hole transport layers, it corresponds to the second hole transport layer) include diffusion of excitation energy of the light-emitting layer. An organic layer having a high triplet energy (preferably 2.6 eV or more), an electron resistance because it is adjacent to the light emitting layer, and a low affinity (preferably 2.4 eV or less) to prevent electrons from leaking from the light emitting layer. In addition, an organic layer having a high ionization potential (preferably 5.5 eV or more) is required to promote hole injection into the light emitting layer. Examples of the material satisfying such characteristics include compounds represented by the following general formulas (4) to (8).

(In the formula (4), in Ar ¹¹ to Ar ^13, at least one is a group represented by the following general formula (4-2), not in Ar ¹¹ to Ar ^13, the general formula (4-2) group Is a group represented by the following general formula (4-3) or (4-4), or a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms.)

(In the formula, X ¹¹ is an oxygen atom or a sulfur atom.
L ^{1 to} L ³ each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the substituent that L ^{1 to} L ³ may have is a carbon number A linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl group having 6 to 30 ring carbon atoms, It is an alkylarylsilyl group having 8 to 15 carbon atoms (the aryl moiety has 6 to 14 ring carbon atoms), an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or a cyano group.
Ar ¹⁴ represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the substituent that Ar ¹⁴ may have is a linear or branched alkyl group having 1 to 10 carbon atoms, A cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl group having 6 to 30 ring carbon atoms, an alkylarylsilyl group having 8 to 15 carbon atoms (of the aryl moiety). The ring forming carbon number is 6 to 14), and the ring forming carbon number is 6 to 50 aryl group, halogen atom or cyano group.
R ^{51 to} R ⁵⁶ are each independently a substituted or unsubstituted linear or branched alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, substituted Or an unsubstituted trialkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted triarylsilyl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylarylsilyl group having 8 to 15 carbon atoms (aryl The number of ring-forming carbon atoms of the moiety is 6 to 14), and represents a substituted or unsubstituted aryl group, halogen atom or cyano group having 6 to 50 ring carbon atoms. A plurality of adjacent R ^{51 to} R ⁵⁶ may be bonded to each other to form a saturated or unsaturated divalent group forming a ring.
b and f each independently represent an integer of 0 to 3, and a, c, d and e each independently represents an integer of 0 to 4. )

When L ¹ in the formula (4-2) and L ³ in the formula (4-4) are an arylene group, an increase in the electron density of the compound represented by the formula (4) is suppressed, and Ip is large. Therefore, since the injection of holes into the light emitting layer is promoted, the voltage of the device is likely to be low, which is preferable. Further, when a dibenzofuran structure or a carbazole structure is bonded to a nitrogen atom via an arylene group, the amine is hardly oxidized, the compound is often stabilized, and the lifetime of the device is likely to be increased. In addition, when L ³ in the formula (4-4) is an arylene group, the compound is stable, so that the synthesis is easy.
Moreover, in said Formula (4), other groups except the group represented by Formula (4-2) among Ar < ¹¹ > -Ar < ¹³ > are represented by Formula (4-2)-(4-4). When it is not any of the groups, it is preferably independently represented by the following formulas (4-5) to (4-7).

[Wherein, R ^{61 to} R ⁶⁴ each independently represents a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, or a tricyclic group having 3 to 10 carbon atoms. An alkylsilyl group, a triarylsilyl group having 6 to 30 ring carbon atoms, an alkylarylsilyl group having 8 to 15 carbon atoms (the ring portion having 6 to 14 ring carbon atoms), an aryl having 6 to 50 ring carbon atoms Group, a halogen atom or a cyano group. A plurality of adjacent R ^{61 to} R ⁶⁴ may combine to form a saturated or unsaturated ring.
k, l, m, and n are each independently an integer of 0 to 4. ]

[In the formulas (5) to (7), Ar ^{15 to} Ar ²¹ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring carbon number 5 to 50. Aromatic heterocyclic group, a substituted or unsubstituted aryl group having 8 to 50 ring carbon atoms to which an aromatic amino group is bonded, or a substituted or unsubstituted ring forming carbon atom having 8 to 5 carbon atoms to which an aromatic heterocyclic group is bonded 50 aryl groups.
Ar ¹⁶ and Ar ¹⁷ , Ar ¹⁸ and Ar ¹⁹ , Ar ²⁰ and Ar ²¹ may be bonded to each other to form a ring.
L ⁴ represents a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the substituent that L ⁴ may have is a linear or branched group having 1 to 10 carbon atoms. An alkyl group, a cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl group having 6 to 30 ring carbon atoms, and an alkylarylsilyl group having 8 to 15 carbon atoms ( The aryl moiety has 6 to 14 ring-forming carbon atoms, an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or a cyano group.
R ^{67 to} R ⁷⁷ are each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms, a substituted or unsubstituted group. Non-condensed aryl group having 6 to 40 ring carbon atoms, substituted or unsubstituted condensed aryl group having 6 to 12 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms, substituted or unsubstituted carbon An alkenyl group having 2 to 40 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 40 carbon atoms, a substituted or unsubstituted aralkylamino group having 7 to 60 carbon atoms, and a substituted or unsubstituted alkyl group having 3 to 20 carbon atoms Silyl group, substituted or unsubstituted ring-forming carbon atoms having 8 to 40 arylsilyl groups, substituted or unsubstituted carbon atoms having 8 to 40 aralkylsilyl groups, substituted or unsubstituted Represents a halogenated alkyl group having 1 to 40 carbon atoms.
R ⁷⁸ and R ⁷⁹ are each independently a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 20 ring atoms, a substituted or unsubstituted ring forming carbon. A non-condensed aryl group having 6 to 40 carbon atoms, a substituted or unsubstituted condensed aryl group having 6 to 12 ring carbon atoms, and a substituted or unsubstituted aralkyl group having 7 to 20 carbon atoms.
g, i, p, q, r, s, w, and x are each independently an integer of 0 to 4.
h, y, and z are each independently an integer of 0 to 3. ]

(In Formula (8), A ¹ and A ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms. Represents.
Y ^{11 to} Y ²⁶ each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
L ¹¹ and L ¹² each independently represent a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and the arylene group that the arylene group may have has 1 to 10 carbon atoms. A linear or branched alkyl group, a cycloalkyl group having 3 to 10 ring carbon atoms, a trialkylsilyl group having 3 to 10 carbon atoms, a triarylsilyl group having 6 to 30 ring carbon atoms, and 8 carbon atoms. -15 alkylarylsilyl groups (the aryl moiety has 6 to 14 ring carbon atoms), an aryl group having 6 to 50 ring carbon atoms, a halogen atom, or a cyano group. )

(5) Light emitting layer When forming a phosphorescent light emitting layer with materials other than the organic EL element layer material of this invention, a well-known material can be used as a material of a phosphorescent light emitting layer. Specifically, Japanese Patent Application No. 2005-517938 may be referred to. Preferred examples of the phosphorescent material include ortho-metalated complexes of iridium (Ir), osmium (Os), or platinum (Pt) metal.
The organic EL element of the present invention may have a fluorescent light emitting layer. A known material can be used for the fluorescent light emitting layer. Specifically, suitable materials described in WO2010 / 134350 and WO2010 / 134352 are selected.

The light emitting layer may be a double host (also referred to as a host / cohost). Specifically, the carrier balance in the light emitting layer may be adjusted by combining an electron transporting host and a hole transporting host in the light emitting layer.
Moreover, it is good also as a double dopant. In the light emitting layer, each dopant emits light by adding two or more dopant materials having a high quantum yield. For example, a yellow light emitting layer may be realized by co-evaporating a host, a red dopant, and a green dopant.

Moreover, a light emitting layer may contain a positive hole transport material, an electron transport material, and a polymer binder as needed.
Furthermore, the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.

(6) Electron Injection / Transport Layer Next, the electron injection / transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a high electron mobility. Among these electron injecting / transporting layers, it is a layer made of a material having particularly good adhesion to the cathode.
In addition, since light emitted from an organic EL element is reflected by an electrode (in this case, a cathode), it is known that light emitted directly from the anode interferes with light emitted via reflection by the electrode. . In order to efficiently use this interference effect, the electron injecting / transporting layer is appropriately selected with a film thickness of several nanometers to several micrometers, but particularly when the film thickness is large, 10 ⁴ to 10 ^{6 in} order to avoid voltage increase. The electron mobility is preferably at least 10 ⁻⁵ cm ² / Vs or more when an electric field of V / cm is applied.
As a material used for the electron injection / transport layer, 8-hydroxyquinoline or a metal complex of its derivative or an oxadiazole derivative is preferable. As a specific example of the metal complex of 8-hydroxyquinoline or its derivative, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum, is injected. It can be used as a material.
Examples of the electron injection material include compounds represented by any of the following general formulas (31) to (36).

In formulas (31) to (33), Z ¹ , Z ² and Z ³ are each independently a nitrogen atom or a carbon atom.
R ¹ and R ² are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, and 1 to 20 carbon atoms. An alkyl group, an alkyl group having 1 to 20 carbon atoms substituted by a halogen atom, or an alkoxy group having 1 to 20 carbon atoms. R ¹ in formulas (31) to (32) may be substituted with either a 5-membered ring or a 6-membered ring, but is preferably substituted with a 6-membered ring. On the other hand, R ¹ in formula (33) is substituted with a 6-membered ring.
n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R ¹ may be the same or different from each other. Further, a plurality of adjacent R ¹ may be bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
Ar ¹ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
Ar ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms substituted by a halogen atom, an alkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring forming carbon atom having 6 to 6 carbon atoms. It is a 50 aryl group or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
However, ^one of Ar ¹ and Ar ² is a substituted or unsubstituted condensed ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted hetero condensed ring group having 9 to 50 ring atoms.
Ar ³ is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
L ¹ , L ² and L ³ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, a substituted or unsubstituted hetero condensed ring group having 9 to 50 ring atoms. Or a substituted or unsubstituted fluorenylene group. Incidentally, L ^2, L ³ in the formula (32) in the formula (31) may be substituted at any of the 5-membered ring and 6-membered ring, respectively, but that is substituted in 5-membered ring preferable.

Specific examples of the aryl group and alkyl group represented by R ¹ , R ² , Ar ¹ , Ar ² include the same examples as R ¹ and R ² in formula (1), and the alkoxy group includes its alkyl group. An example in which an oxygen atom is bonded to is given. Examples of heteroaryl groups represented by R ¹ , R ² , Ar ¹ and Ar ² include pyrrolyl, pyridinyl, pyrazinyl, pyrimidinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, A quinolinyl group, an isoquinolinyl group, a quinoxanyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, and the like can be given. Examples of the arylene group represented by Ar ³ , L ¹ , L ² and L ³ include a divalent example of the aryl group, and examples of the hetero condensed ring group include a condensed ring group in which the number of carbon atoms forming the heteroaryl group is suitable. It is done.

（式中、Ｘは窒素原子あるいは硫黄原子を含んだ縮合環であり、Ｙは単結合、アルキル鎖、アルキレン鎖、シクロアルキル鎖、アリール鎖、複素環鎖、シリル鎖、エーテル鎖、あるいはチオエーテル鎖のいずれかより単独又は組み合わせたものより選ばれる。ｑは２以上の自然数である。
また、一般式（３４）で表される化合物の分子量は４８０以上である。）

(Wherein X is a condensed ring containing a nitrogen atom or a sulfur atom, and Y is a single bond, alkyl chain, alkylene chain, cycloalkyl chain, aryl chain, heterocyclic chain, silyl chain, ether chain, or thioether chain. And q is a natural number of 2 or more.
Moreover, the molecular weight of the compound represented by General formula (34) is 480 or more. )

（式中、Ａはフェナントロリン骨格又はベンゾキノリン骨格を有する置換基である。Ｂは下記式（３５Ａ）で表される構造を有するｐ価の有機基である。ｐは２以上の自然数である。）

(In the formula, A is a substituent having a phenanthroline skeleton or a benzoquinoline skeleton. B is a p-valent organic group having a structure represented by the following formula (35A). P is a natural number of 2 or more. )

（式中、Ｒ⁴とＲ⁵はそれぞれ独立にアルキル基又はアリール基（フェニル基に縮合したアリール基を含む）のいずれかである。ｌとｍはそれぞれ独立に０〜５までの自然数である。Ｚは下記式（３５Ｂ）から選ばれた少なくとも１種である。）

(In the formula, R ⁴ and R ⁵ are each independently an alkyl group or an aryl group (including an aryl group condensed to a phenyl group). L and m are each independently a natural number from 0 to 5. Z is at least one selected from the following formula (35B).)

（式中、Ｒ⁶及びＲ⁷は同じでも異なっていてもよく、それぞれ、水素原子、アルキル基、シクロアルキル基、複素環基、アルケニル基、シクロアルケニル基、アルキニル基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、ヘテロアリール基、シアノ基、カルボニル基、エステル基、カルバモイル基、アミノ基、シリル基、並びに隣接置換基との間に形成される縮合環の中から選ばれる。Ａｒ⁴はアリール基又はヘテロアリール基を表す。）

(In the formula, R ⁶ and R ⁷ may be the same or different and are each a hydrogen atom, an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, Aryl ether group, aryl thioether group, aryl group, heteroaryl group, cyano group, carbonyl group, ester group, carbamoyl group, amino group, silyl group, and a condensed ring formed between adjacent substituents Ar ⁴ represents an aryl group or a heteroaryl group.)

It is also preferred that the organic EL device of the present invention has at least one of an electron donating dopant and an organometallic complex in the interface region between the cathode and the organic thin film layer.
According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
Examples of the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
Examples of the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.

Examples of the alkali metal include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV), and the like, and those having a work function of 2.9 eV or less are preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
Examples of the alkaline earth metal include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV). A work function of 2.9 eV or less is particularly preferable.
Examples of the rare earth metal include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
Among the above metals, preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.

Examples of the alkali metal compound include lithium oxide (Li ₂ O), cesium oxide (Cs ₂ O), alkali oxides such as potassium oxide (K ₂ O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine. Examples thereof include alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li ₂ O), and sodium fluoride (NaF) are preferable.
Examples of the alkaline earth metal compound include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba _x Sr _1-x O) (0 <x <1), Examples thereof include barium calcium oxide (Ba _x Ca _1-x O) (0 <x <1), and BaO, SrO, and CaO are preferable.
The rare earth metal compound, ytterbium fluoride (YbF _3), scandium fluoride (ScF _3), scandium oxide (ScO _3), yttrium oxide (Y ₂ O _3), cerium oxide (Ce ₂ O _3), gadolinium fluoride (GdF _3), include such terbium fluoride (TbF _{3) is, YbF 3, ScF 3, TbF} 3 are preferable.

  As described above, the organometallic complex is not particularly limited as long as it contains at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions. The ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl thiadiazole, hydroxydiaryl thiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines, and derivatives thereof are preferred, but are not limited thereto.

  The addition form of the electron donating dopant and the organometallic complex is preferably formed in a layered or island shape in the interface region. As a forming method, while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material as a light emitting material or an electron injection material for forming an interface region is simultaneously deposited, and an electron is deposited in the organic material. A method of dispersing at least one of the donor dopant and the organometallic complex is preferable. The dispersion concentration is usually an organic substance: electron-donating dopant and / or organometallic complex in a molar ratio of 100: 1 to 1: 100, preferably 5: 1 to 1: 5.

In the case where at least one of the electron donating dopant and the organometallic complex is formed in a layered form, after forming the light emitting material or the electron injecting material that is the organic layer at the interface in a layered form, at least one of the electron donating dopant and the organometallic complex is formed. These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
In the case where at least one of an electron donating dopant and an organometallic complex is formed in an island shape, a light emitting material or an electron injecting material which is an organic layer at the interface is formed in an island shape, and then the electron donating dopant and the organometallic complex are formed. At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
In the organic EL device of the present invention, the ratio of at least one of the main component and the electron donating dopant and the organometallic complex is, as a molar ratio, the main component: the electron donating dopant and / or the organometallic complex = 5. Is preferably 1: 1 to 1: 5, and more preferably 2: 1 to 1: 2.

(7) Cathode As the cathode, in order to inject electrons into the electron injecting / transporting layer or the light emitting layer, a material having a small work function (4 eV or less), an alloy, an electrically conductive compound and a mixture thereof are used as electrode materials. Used. Specific examples of such electrode materials include sodium, sodium / potassium alloy, magnesium, lithium, magnesium / silver alloy, aluminum / aluminum oxide, aluminum / lithium alloy, indium, and rare earth metals.
The cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
Here, when light emitted from the light emitting layer is taken out from the cathode, it is preferable that the transmittance with respect to the light emitted from the cathode is larger than 10%.
The sheet resistance as the cathode is preferably several hundred Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, preferably 50 to 200 nm.

(8) Insulating layer Since an organic EL element applies an electric field to an ultrathin film, pixel defects due to leakage or short-circuiting are likely to occur. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes.
Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, Examples thereof include germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and a mixture or a laminate thereof may be used.

(9) Manufacturing method of organic EL element An organic EL device is formed by forming an anode, a light emitting layer, a hole transport layer, and an electron injection / transport layer as required, and further forming a cathode by the materials and formation methods exemplified above. An element can be manufactured. Moreover, an organic EL element can also be produced from the cathode to the anode in the reverse order.
Hereinafter, an example of manufacturing an organic EL device having a structure in which an anode / hole transport layer / light emitting layer / electron injection / transport layer / cathode are sequentially provided on a light transmitting substrate will be described.
First, a thin film made of an anode material is formed on a suitable light-transmitting substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 μm or less, preferably 10 to 200 nm. Next, at least two or more hole transport layers are sequentially provided on the anode. The hole transport layer can be formed by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. However, it is easy to obtain a uniform film and pinholes are not easily generated. It is preferable to form by a vacuum evaporation method. When forming a hole transport layer by vacuum deposition, the deposition conditions vary depending on the compound used (the material of the hole transport layer), the crystal structure and recombination structure of the target hole transport layer, etc. The source temperature is preferably selected from the range of 50 to 450 ° C., the degree of vacuum of 10 ⁻⁷ to 10 ⁻³ Torr, the deposition rate of 0.01 to 50 nm / second, the substrate temperature of −50 to 300 ° C., and the thickness of 5 nm to 5 μm. .

Next, the formation of a light emitting layer in which a light emitting layer is provided on the hole transport layer is also performed by thinning the organic light emitting material using a desired organic light emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting. However, it is preferably formed by a vacuum deposition method from the viewpoint that a homogeneous film is easily obtained and pinholes are hardly generated. In the case of forming a light emitting layer by a vacuum vapor deposition method, the vapor deposition conditions vary depending on the compound used, but can generally be selected from the same condition range as that of the hole transport layer.
Next, an electron injection / transport layer is provided on the light emitting layer. As with the hole transport layer and the light emitting layer, it is preferable to form by a vacuum evaporation method because it is necessary to obtain a homogeneous film. Deposition conditions can be selected from the same condition ranges as the hole transport layer and the light emitting layer.
Finally, an organic EL element can be obtained by laminating a cathode.
The cathode is made of metal, and vapor deposition or sputtering can be used. However, vacuum deposition is preferred to protect the underlying organic layer from damage during film formation.
The organic EL element is preferably manufactured from the anode to the cathode consistently by a single vacuum.
When a direct current voltage is applied to the organic EL element, light emission can be observed by applying a voltage of 5 to 40 V with a positive polarity of the anode and a negative polarity of the cathode. Further, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Further, when alternating voltage is applied, uniform light emission is observed only when the anode has a positive polarity and the cathode has a negative polarity. The waveform of the alternating current to be applied may be arbitrary.
The organic EL device obtained by using the compound of the present invention can increase the thickness of the hole transport layer, can adjust the optical film thickness of the organic EL device, and can improve the light emission efficiency and life of the device. For this reason, it can be used in electronic devices such as display components such as organic EL panel modules; display devices such as televisions, mobile phones, personal computers; and light emitting devices for lighting and vehicular lamps. In particular, it is useful as a flat light emitter or a backlight of a display.

  EXAMPLES Next, although an Example demonstrates this invention still in detail, this invention is not limited at all by these examples.

Intermediate Synthesis Example 1 (Synthesis of Intermediate 1)
Under an argon atmosphere, 55 g (201.3 mmol) of 2-bromo-9,9-dimethylfluorene was added to 23 g (90.6 mmol) of iodine, 9.4 g (41.2 mmol) of periodic acid dihydrate, 42 ml of water, and 360 ml of acetic acid. And 11 ml of sulfuric acid were added and stirred at 65 ° C. for 30 minutes, and then stirred at 90 ° C. for 6 hours.
After completion of the reaction, the reaction product was poured into ice water, and the precipitated crystals were collected by filtration. By washing with water and then with methanol, 61 g of a white solid was obtained. The following intermediate body 1 was identified by analysis of FD-MS. (Yield 76%)

Intermediate Synthesis Example 2 (Synthesis of Intermediate 2)
Under an argon atmosphere, 30.9 g (100.0 mmol) of 4-bromo-p-terphenyl, 9.3 g (100.0 mmol) of aniline, 13.0 g (135.3 mmol) of t-butoxy sodium, tris (dibenzylideneacetone) 500 ml of dehydrated toluene was added to 460 mg (0.5 mmol) of dipalladium (0) and 210 mg (1.04 mmol) of tri-t-butylphosphine, and reacted at 80 ° C. for 8 hours.
After cooling, 2.5 l of water was added, the mixture was filtered through Celite, and the filtrate was extracted with toluene and dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, recrystallized from toluene, collected by filtration and dried to obtain 15.7 g of a pale yellow solid. The following intermediate body 2 was identified by analysis of FD-MS. (Yield 49%)

Intermediate Synthesis Example 3 (Synthesis of Intermediate 3)
A reaction was conducted in the same manner as in Synthesis Example 2 except that 39.9 g of Intermediate 1 was used instead of 4-bromo-p-terphenyl and 32.1 g of Intermediate 2 was used instead of aniline. Of a white solid was obtained. The following intermediate body 3 was identified by analysis of FD-MS. (Yield 65%)

Intermediate Synthesis Example 4 (Synthesis of Intermediate 4)
The same reaction as in Synthesis Example 2 except that 23.3 g of 4-bromobiphenyl was used instead of 4-bromo-p-terphenyl and 20.9 g of 9,9-dimethyl-2-aminofluorene was used instead of aniline. As a result, 20.6 g of a pale yellow solid was obtained. The following intermediate body 4 was identified by analysis of FD-MS. (Yield 57%)

Intermediate Synthesis Example 5 (Synthesis of Intermediate 5)
Under an argon atmosphere, 28.3 g (100.0 mmol) of 4-iodobromobenzene, 22.3 g (105.0 mmol) of dibenzofuran-4-boronic acid, 2.31 g (2.00 mmol) of Pd [PPh ₃ ] ₄ and 150 ml of toluene Then, 150 ml of dimethoxyethane, 150 ml (300.0 mmol) of 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated to reflux with stirring for 10 hours.
After completion of the reaction, the sample was transferred to a separatory funnel and extracted with dichloromethane. The organic layer was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 26.2 g of a white solid. The following intermediate body 5 was identified by analysis of FD-MS. (Yield 81%)

Intermediate Synthesis Example 6 (Synthesis of Intermediate 6)
A reaction was conducted in the same manner as in Synthesis Example 2 except that 32.3 g of Intermediate 5 was used instead of 4-bromo-p-terphenyl, to obtain 23.5 g of a pale yellow solid. The following intermediate body 6 was identified by analysis of FD-MS. (Yield 70%)

Intermediate Synthesis Example 7 (Synthesis of Intermediate 7)
Under an argon atmosphere, 28.3 g (100.0 mmol) of 4-iodobromobenzene, 18.7 g (105.0 mmol) of benzo [b] thiophen-2-ylboronic acid, 2.31 g (2.00 mmol) of Pd [PPh ₃ ] ₄ ) Were added 150 ml of toluene, 150 ml of dimethoxyethane, 150 ml (300.0 mmol) of 2M Na ₂ CO ₃ aqueous solution, and the mixture was heated to reflux with stirring for 10 hours.
The reaction solution was extracted with toluene / water and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, and the resulting crude product was subjected to column purification to obtain 11.3 g of white powder. The following intermediate body 7 was identified by analysis of FD-MS. (Yield 39%)

Intermediate Synthesis Example 8 (Synthesis of Intermediate 8)
The reaction was conducted in the same manner as in Synthesis Example 2 except that 28.9 g of Intermediate 7 was used instead of 4-bromo-p-terphenyl, to obtain 19.9 g of a pale yellow solid. The following intermediate body 8 was identified by analysis of FD-MS. (Yield 66%)

Intermediate synthesis example 9 (synthesis of intermediate 9)
Under argon stream, phenylboronic acid 750 g (6.15 mol), 2-bromothiophene 1000 g (6.13 mol), Pd [PPh ₃ ] ₄ 142 g (123 mmol), toluene 9 L, dimethoxyethane 9 L, 2 M Na ₂ CO ₃ aqueous solution 9 L (18 mol) was added, and the mixture was stirred with heating at 80 ° C. for 8 hours.
The reaction solution was extracted with toluene / water and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, and the resulting crude product was subjected to column purification to obtain 786 g of white powder.
Under an argon stream, 8 L of DMF (dimethylformamide) was added to 786 g of the compound obtained above, and then 960 g of NBS (N-bromosuccinimide) was gradually added, followed by reaction at room temperature for 12 hours.
Extracted with hexane / water and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, and the resulting crude product was purified by column to obtain 703 g of white powder. The following intermediate body 9 was identified by analysis of FD-MS. (Yield 48%)

Intermediate Synthesis Example 10 (Synthesis of Intermediate 10)
Under an argon stream, 7 L of dehydrated THF (tetrahydrofuran) was added to 703 g (2.94 mol) of the intermediate 9 and cooled to -30 ° C. n-Butyllithium (1.6M hexane solution) 2.3 L (3.68 mol) was gradually added and stirred at −30 ° C. for 1 hour. After cooling to -70 ° C, 1658 g (8.82 mol) of triisopropyl borate was added. Then, it heated up gradually and stirred at room temperature for 1 hour.
1.7 L of 10% hydrochloric acid solution was added and stirred. The mixture was extracted with ethyl acetate and water, and the organic layer was washed with water. It dried with the anhydrous sodium sulfate and the solvent was distilled off. By washing with hexane, 359 g of white powder was obtained.
Under an argon stream, 359 g (1.76 mol) of 5-phenyl-2-thiopheneboronic acid obtained above, 492 g (1.74 mol) of 4-iodobromobenzene, 402 g (348 mmol) of Pd [PPh ₃ ] ₄ and toluene 2 .6L, dimethoxyethane 2.6L, 2M Na ₂ CO ₃ aqueous solution 2.6L (5.2 mol) was added, and the mixture was heated and stirred at 80 ° C. for 8 hours.
The reaction solution was extracted with toluene / water and dried over anhydrous sodium sulfate. This was concentrated under reduced pressure, and the resulting crude product was purified by force to obtain 277 g of white powder. The following intermediate body 10 was identified by analysis of FD-MS. (Yield 30%)

Intermediate Synthesis Example 11 (Synthesis of Intermediate 11)
The reaction was conducted in the same manner as in Synthesis Example 2 except that 31.5 g of the intermediate 10 was used instead of 4-bromo-p-terphenyl. As a result, 18.3 g of a pale yellow solid was obtained. The following intermediate body 11 was identified by analysis of FD-MS. (Yield 56%)

Synthesis Example 1 (Production of Compound (H1))
Under an argon stream, 7.1 g of 2,7-dibromo-9,9-dimethylfluorene, 12.8 g of intermediate 2, 2.6 g of sodium t-butoxy, 92 mg of tris (dibenzylideneacetone) dipalladium (0), tri- 42 mg of t-butylphosphine and 100 mL of dehydrated toluene were added and reacted at 80 ° C. for 8 hours.
After cooling, 500 mL of water was added, the mixture was filtered through Celite, and the filtrate was extracted with toluene and dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting crude product was purified by column, recrystallized from toluene, filtered, and dried to obtain 8.3 g of a pale yellow powder. The following compound (H1) was identified by analysis of FD-MS. (Yield 50%)

Synthesis Example 2 (Production of compound (H2))
Under an argon stream, intermediate 3 11.9 g, N- (1-naphthyl) -N-phenylamine 4.4 g, t-butoxy sodium 2.6 g, tris (dibenzylideneacetone) dipalladium (0) 92 mg, tri- 42 mg of t-butylphosphine and 100 mL of dehydrated toluene were added and reacted at 80 ° C. for 8 hours.
After cooling, 500 mL of water was added, the mixture was filtered through Celite, and the filtrate was extracted with toluene and dried over anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the resulting crude product was purified by column, recrystallized from toluene, filtered, and dried to obtain 8.5 g of a pale yellow powder. The following compound (H2) was identified by analysis of FD-MS. (Yield 62%)

Synthesis Example 3 (Production of compound (H3))
In Synthesis Example 2, the reaction was performed in the same manner except that 4.9 g of N- (4-biphenyl) -N-phenylamine was used instead of N- (1-naphthyl) -N-phenylamine. Obtained 2 g of white crystals. The following compound (H3) was identified by analysis of FD-MS. (Yield 65%)

Synthesis Example 4 (Production of compound (H4))
In Synthesis Example 2, the reaction was performed in the same manner except that 6.4 g of N, N-bis (4-biphenyl) amine was used instead of N- (1-naphthyl) -N-phenylamine, and 10.0 g Of white crystals were obtained. The following compound (H4) was identified by analysis of FD-MS. (Yield 60%)

Synthesis Example 5 (Production of compound (H5))
A reaction was conducted in the same manner as in Synthesis Example 2 except that 7.2 g of Intermediate 4 was used instead of N- (1-naphthyl) -N-phenylamine to obtain 10.0 g of white crystals. The following compound (H5) was identified by analysis of FD-MS. (Yield 52%)

Synthesis Example 6 (Production of compound (H6))
A reaction was conducted in the same manner as in Synthesis Example 2 except that 6.7 g of intermediate 6 was used instead of N- (1-naphthyl) -N-phenylamine, to obtain 8.0 g of white crystals. The following compound (H6) was identified by analysis of FD-MS. (Yield 45%)

Synthesis Example 7 (Production of compound (H7))
A reaction was conducted in the same manner as in Synthesis Example 2 except that 6.0 g of Intermediate 8 was used instead of N- (1-naphthyl) -N-phenylamine, to obtain 10.6 g of white crystals. The following compound (H7) was identified by analysis of FD-MS. (Yield 65%)

Synthesis Example 8 (Production of compound (H8))
In Synthesis Example 2, a reaction was performed in the same manner except that 6.5 g of intermediate 11 was used instead of N- (1-naphthyl) -N-phenylamine, to obtain 6.7 g of white crystals. The following compound (H8) was identified by analysis of FD-MS. (Yield 40%)

  In addition, if it refers to the manufacturing method of the said intermediate body 1-the intermediate body 11, the manufacturing method of the said intermediate body 2-1-intermediate body 2-3, and the manufacturing method of compound (H1)-(H8), it is Claim Various compounds contained in can also be produced by using raw materials suitable for the purpose.

Example 1
(Production of organic EL element)
A 25 mm × 75 mm × 1.1 mm glass substrate with an ITO transparent electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and further UV (Ultraviolet) ozone cleaned for 30 minutes.
A glass substrate with a transparent electrode line after cleaning is attached to a substrate holder of a vacuum deposition apparatus, and the following acceptor material (A) is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, An acceptor layer having a thickness of 5 nm was formed. On this acceptor layer, the compound (H1) obtained in Synthesis Example 1 was vapor-deposited as a first hole transport material to form a first hole transport layer having a thickness of 65 nm. Following the formation of the first hole transport layer, the following aromatic amine derivative (X1) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
On this second hole transport layer, the phosphorescent host compound (B) and the phosphorescent dopant Ir (ppy) ₃ were co-evaporated at a thickness of 25 nm to obtain a phosphorescent light emitting layer. The concentration of Ir (ppy) ₃ was 10% by mass.
Subsequently, a compound (C) having a thickness of 35 nm, LiF having a thickness of 1 nm, and metal Al having a thickness of 80 nm were sequentially laminated on the phosphorescent light emitting layer to form a cathode. Note that LiF, which is an electron injecting electrode, was formed at a deposition rate of 1 Å / min. The obtained organic EL device was caused to emit light by direct current driving, and the luminance (L) and current density were measured, and the current efficiency (L / J) and driving voltage (V) at a current density of 10 mA / cm ² were obtained. Furthermore, the lifetime of the element at a current density of 50 mA / cm ² (the time during which the luminance is reduced to 80%) was determined. The results are shown in Table 1.

Examples 2-8
In Example 1, an organic EL device was produced in the same manner as in Example 1 except that the compound shown in Table 1 was used instead of the compound (H1) as the first hole transport material. The obtained organic EL device was caused to emit light by direct current driving, and the luminance (L) and current density were measured, and the current efficiency (L / J) and driving voltage (V) at a current density of 10 mA / cm ² were obtained. Furthermore, the lifetime of the element at a current density of 50 mA / cm ² (the time during which the luminance is reduced to 80%) was determined. The results are shown in Table 1.

Comparative Examples 1-4
In Example 1, the organic EL element was produced like Example 1 except having used the following comparative compounds 1-4 instead of the compound (H1) as a 1st hole transport material. The obtained organic EL device was caused to emit light by direct current driving, and the luminance (L) and current density were measured, and the current efficiency (L / J) and driving voltage (V) at a current density of 10 mA / cm ² were obtained. Furthermore, the lifetime of the element at a current density of 50 mA / cm ² (the time during which the luminance is reduced to 80%) was determined. The results are shown in Table 1.

Claims (17)

A compound represented by the following general formula (1).

[Wherein, L ¹ and L ² are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 10 ring carbon atoms.
R ¹ and R ² are each independently a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms.
Ar ^{1 to} Ar ⁴ are at least one group represented by the following general formula (2), and the others are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. .

(R ^{3 to} R ⁵ are each independently an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. , An aryloxy group having 6 to 30 ring carbon atoms, an aryl group having 6 to 30 ring carbon atoms, a halogen atom, or a cyano group, and R ^{3 to} R ⁵ are bonded to each other to form a hydrocarbon ring. Also good.
a and b are each independently an integer of 0 to 4; c is an integer of 0-5. When a, b or c is 2 or more, adjacent R ^{3 s} , adjacent R ^{4 s} or adjacent R ^{5 s} may be bonded to each other to form a hydrocarbon ring. ]] The compound according to claim 1, wherein the group represented by the general formula (2) is represented by the following general formula (3) or (4).

(Wherein R ^{3 to} R ⁵ and a to c are as defined above.) The compound according to claim 1 or 2, wherein Ar ¹ and Ar ² are a group represented by the general formula (2). The compound according to claim 1 or 2, wherein Ar ¹ and Ar ³ are a group represented by the general formula (2). The compound according to claim 1 or 2, wherein three or more of Ar ^{1 to} Ar ⁴ are different from each other. The compound according to claim 1 or 2, wherein three of Ar ^{1 to} Ar ⁴ are the same. The compound according to any one of claims 1 to 6, wherein both L ¹ and L ² are a single bond. The compound according to any one of claims 1 to 6, wherein L ¹ is a single bond, and L ² is a phenylene group. 2. A compound according to claim 1 selected from the group of compounds below.

  The hole transport material for organic electroluminescent elements which has an acceptor layer adjacent hole transport layer which consists of a compound in any one of Claims 1-9.   It is an organic electroluminescent element which has an organic thin film layer between the anode and cathode which oppose, Comprising: It has one or more organic thin film layers containing the compound in any one of Claims 1-9, It is characterized by the above-mentioned. Organic electroluminescence device.   It is an organic electroluminescent element which has an at least 2 or more positive hole transport layer and a light emitting layer in order between the anode and cathode which oppose, Comprising: One of this positive hole transport layer is any one of Claims 1-9 An organic electroluminescence device comprising the compound according to 1 and not adjacent to the light emitting layer.   The at least two or more hole transport layers comprise a first hole transport layer on the anode side and a second hole transport layer on the light emitting layer side, and the first hole transport layer is any one of claims 1 to 8. The organic electroluminescent element of Claim 12 containing the compound of Claim 12.   The organic electroluminescent element according to claim 12 or 13, further comprising an acceptor layer containing an acceptor material between the anode and the at least two or more hole transport layers.   The at least two or more hole transport layers are composed of a first hole transport layer on the anode side and a second hole transport layer on the light emitting layer side, and the first hole transport layer contains an acceptor material. Or the organic electroluminescent element of 13. The organic electroluminescent element according to claim 14 or 15, wherein the acceptor material is represented by any one of the following general formulas (A) to (C).

(In Formula (A), R ^{11 to} R ¹⁶ are each independently a cyano group, —CONH ₂ , a carboxyl group, or —COOR ¹⁷ (R ¹⁷ is an alkyl group having 1 to 20 carbon atoms). R ¹¹ and R ¹² , R ¹³ and R ¹⁴ , or R ¹⁵ and R ¹⁶ are bonded to each other to represent a group represented by —CO—O—CO—.

[In formula (B), R ^{21 to} R ²⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. Group, substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, halogen atom, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 50 ring carbon atoms An oxy group or a cyano group. R ²¹ and R ²² , and R ²³ and R ²⁴ may be bonded to each other to form a ring.
Y ^{1 to} Y ⁴ are each independently —N═, —CH═, or —C (R ²⁵ ) ═. R ²⁵ represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. A group, a halogen atom, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, or a cyano group.
Ar ¹⁰ represents a condensed ring having 6 to 24 ring carbon atoms or a heterocyclic ring having 6 to 24 ring atoms. ar ¹ and ar ² each independently represent a ring of the following general formula (i) or (ii).

In the above formulas, X ¹ and X ² each independently represents any of divalent groups of the following (a) ~ (g).

(Wherein R ^{31 to} R ³⁴ may be the same as or different from each other, and are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring forming carbon number of 6 to 50). Or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and R ³² and R ³³ may be bonded to each other to form a ring.

(In the formula, Z ^{1 to} Z ³ are each independently a divalent group represented by the following general formula (h).)

(In the formula, Ar ³¹ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.)   The electronic device carrying the organic electroluminescent element in any one of Claims 11-16.