WO2014073307A1 - Organic electroluminescent element and electronic device - Google Patents

Abstract

This organic electroluminescent element is characterized by including: a positive electrode; a negative electrode that is provided so as to face the positive electrode; a light-emitting layer that is provided between the positive electrode and the negative electrode, and that contains a compound represented by general formula (1); and an electron transport layer that is provided between the light-emitting layer and the negative electrode, and that contains a compound represented by general formula (21).

Description

Organic electroluminescence device and electronic device

The present invention relates to an organic electroluminescence element and an electronic device.

Organic electroluminescence devices using organic substances (hereinafter sometimes abbreviated as “organic EL devices”) are promising for use as solid light-emitting, inexpensive, large-area full-color display devices, and many developments have been made. ing. In general, an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.

Conventional organic EL elements have a higher driving voltage and lower luminance and luminous efficiency than inorganic light emitting diodes. Further, the characteristic deterioration has been remarkably not put into practical use. Although recent organic EL devices have been gradually improved, further higher light emission efficiency, longer life, improved color reproducibility, and the like are required.

The performance of organic EL elements has been gradually improved by improving the light emitting material for organic EL. In particular, improving the color purity of blue organic EL elements (shortening the emission wavelength) is an important technique that leads to improved color reproducibility of displays.
Patent Document 1 describes an organic EL element including a light-emitting layer containing an aryl-substituted anthracene derivative as a host material and a fluoranthene derivative as a dopant material. Patent Document 1 describes that an organic EL element including the light emitting layer has a long lifetime, high light emission efficiency, and blue light emission.

International Publication No. 2007/100010

However, the efficiency of the organic EL element described in Patent Document 1 is not sufficient, and further improvement in efficiency is required when the organic EL element is used as a light source of an electronic device such as a lighting device or a display device.

Therefore, an object of the present invention is to provide an organic electroluminescence element that emits light with high efficiency and an electronic device equipped with the organic electroluminescence element.

An organic electroluminescence device according to one embodiment of the present invention includes an anode, a cathode provided to face the anode, a compound provided between the cathode and the anode, and represented by the following general formula (1) And a light-emitting layer including: an electron-transporting layer that is provided between the light-emitting layer and the cathode and includes a compound represented by the following general formula (21).

[In the general formula (1),
a, b and c each represents an integer of 1 to 4;
Any one of R ¹⁰¹ to R ¹¹⁰ is a single bond and is used for bonding to L ¹ ;
R ¹⁰¹ to R ¹¹⁰ not used for bonding to L ¹ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon number of 1 to 20 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring carbon atoms, and substituted or unsubstituted arylthio groups having 6 to 20 ring carbon atoms. Selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L ¹ is selected from either a single bond or a linking group, and when L ¹ is a linking group, L ¹ is a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 50 ring carbon atoms. (A + 1) hydrogen atoms can be removed (a + 1) valent residues, substituted or unsubstituted heterocyclic structures with 5 to 50 ring atoms (a + 1) hydrogen atoms can be removed (a + 1) A (a + 1) valence obtained by removing (a + 1) hydrogen atoms from a valent residue or a structure formed by bonding 2 to 4 at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure Is the residue. If L ¹ is a linking group, ^R 101 ^{~ R 110} which is not used in binding to ^{L 1} may also form a substituent and the ring ^{L 1} or ^{L 1.} When c is an integer of 2 to 4, L ¹ may be the same or different. When a or c is an integer of 2 to 4, Z ¹ may be the same or different.
Z ¹ represents a structure represented by the following general formula (2). ]

[In the general formula (2),
1 one of R ¹¹¹ ~ ^{R 120} are used for binding to ^{L 1} represents a single bond, ^R 111 ^{~ R 118} which is not used in binding to ^{L 1} are each independently a bond between ^{L 1} It is synonymous with R ¹⁰¹ to R ¹¹⁰ that are not used in the above. R ¹¹⁹ to R ^{120 which} are not used for bonding to L ¹ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trialkyl having 1 to 30 carbon atoms. A silyl group, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 to 50 Are selected from the group consisting of Further, at least one pair of adjacent two of the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ Two substituents may form a ring structure represented by the following general formula (3). Also, ^R 111 ^{~ R 120} which is not used in binding to ^{L 1} may also form a substituent and the ring ^{L 1} or ^{L 1.} ]

[In the general formula (3),
y ¹ and y ² represent bonding positions with adjacent groups in R ¹¹¹ to R ¹¹⁸ of the general formula (2).
R ¹²¹ to R ¹²⁴ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring forming carbon It is selected from the group consisting of aromatic hydrocarbon groups of 6 to 50 and substituted or unsubstituted heterocyclic groups of 5 to 50 ring-forming atoms.
Any one of R ¹¹¹ to R ¹²⁰ that does not form a ring in the general formula (2) and R ¹²¹ to R ^{124 in} the general formula (3) is used for bonding to L ^{1 in the} general formula (1). Single bond. ]

[In the general formula (21),
X ¹ to X ³ are each independently a nitrogen atom or CR ²⁰¹ . However, at least one of X ¹ to X ³ is a nitrogen atom. R ²⁰¹ has the same ^meaning as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1). Ar ²⁰¹ is represented by the following general formula (22). Ar ²⁰² and Ar ²⁰³ are each independently represented by the following general formula (22), a substituted or unsubstituted aromatic group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring-forming atom. It is a heterocyclic group of several 5-30. ]

[In the general formula (22),
HAr is represented by the following general formula (23).
d is 1 or 2.
L ² is a single bond or a linking group comprising a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms. When d is 1, L ² is a single bond or a divalent linking group. When d is 2, L ² is a trivalent linking group, and HAr is the same or different. ]

[In the general formula (23),
X ¹¹ to X ¹⁸ are each independently a carbon atom bonded to the nitrogen atom, CR ²⁰² , or L ² with a single bond.
Y ¹ represents an oxygen atom, a sulfur ^{atom, N-R 203, CR 204} R 205, nitrogen atom bonded by a single bond to ^{L 2,} or, in ^{CR 206} for coupling with a single bond to ^{L 2} is there.
R ²⁰² to R ²⁰⁶ have the same ^meanings as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1).
However, the bond to L ² is any ^one of carbon atoms from X ¹¹ to X ¹⁸ , carbon atoms from R ²⁰³ to R ²⁰⁵ , nitrogen atoms in Y ¹ , and carbon atoms in Y ¹ . is there. ]

An electronic apparatus according to one embodiment of the present invention includes the above-described organic electroluminescence element.

According to the present invention, it is possible to provide an organic electroluminescence element that emits light with high efficiency, and an electronic device including the organic electroluminescence element.

It is a figure which shows schematic structure of an example of the organic electroluminescent element which concerns on embodiment of this invention.

[Organic EL device]
(Element structure of organic EL element)
Hereinafter, the element configuration of the organic EL element according to the present invention will be described.
The organic EL device of the present invention includes an organic layer between a pair of electrodes. This organic layer has at least two layers composed of an organic compound. The organic layer may contain an inorganic compound.
In the organic EL device of the present invention, at least one of the organic layers is a light emitting layer, and at least one layer is an electron transport layer. Therefore, the organic layer may be composed of, for example, one light emitting layer and one electron transport layer, and further includes a hole injection layer, a hole transport layer, an electron injection layer, a hole barrier layer, and an electron barrier. You may have the layer employ | adopted with organic EL elements, such as a layer.

As a typical element configuration of the organic EL element,
(A) Anode / light emitting layer / cathode (b) Anode / light emitting layer / electron injection / transport layer / cathode (c) Anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode (d) Anode Examples include / hole injection / transport layer / light emitting layer / barrier layer / electron injection / transport layer / cathode structure.
Among the above, the configuration (c) is preferably used, but of course is not limited thereto.
The “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed. At this time, the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function. In the case of a phosphorescent element, the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
The above “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “electron transport layer” or “electron injection layer”. "Layer and electron transport layer". Here, when it has a positive hole injection layer and a positive hole transport layer, it is preferable that the positive hole injection layer is provided in the anode side. Moreover, when it has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided in the cathode side.

In the present invention, the term “electron transport layer” refers to an organic layer in an electron transport region existing between a light emitting layer and a cathode. When the electron transport region is composed of one layer, the layer is an electron transport layer. In addition, in the phosphorescent organic EL device, as shown in the configuration (e), a barrier layer that does not necessarily have high electron mobility is used to prevent diffusion of excitation energy generated in the light emitting layer. The organic layer adjacent to the light emitting layer does not necessarily correspond to the electron transport layer.

In FIG. 1, schematic structure of an example of the organic EL element in embodiment of this invention is shown.
The organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
The organic layer 10 has a light emitting layer 5 containing a host material and a dopant material. The organic layer 10 has a hole transport layer 6 between the light emitting layer 5 and the anode 3. Further, the organic layer 10 has an electron transport layer 7 between the light emitting layer 5 and the cathode 4.

(Light emitting layer)
-Host material As a host material used for the organic EL element of this invention, the compound represented by following General formula (1) can be used.

[In the general formula (1), a, b and c each represent an integer of 1 to 4. Any c number of R ¹⁰¹ ~ ^{R 110} are used for binding to ^{L 1} a single bond, ^R 101 ^{~ R 110} which is not used in binding to ^{L 1} are each independently a hydrogen atom, a halogen atom , Hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted ring formation Aryloxy group having 6 to 20 carbon atoms, substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and substituted or unsubstituted selected from the group consisting of heterocyclic group ring atoms 5 ~ 50, L ¹ is selected from either a single bond, or a linking group, if the L ¹ is a linking group, L ¹ is also substituted It An (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from an unsubstituted aromatic hydrocarbon ring structure having 6 to 50 carbon atoms, substituted or unsubstituted ring atoms having 5 to 50 ring atoms (A + 1) -valent residue formed by removing (a + 1) hydrogen atoms from the heterocyclic structure, or at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure is bonded to form 2-4. (A + 1) -valent residue formed by removing (a + 1) hydrogen atoms from the structure. If L ¹ is a linking group, ^R 101 ^{~ R 110} which is not used in binding to ^{L 1} may also form a substituent and the ring ^{L 1} or ^{L 1.} When c is an integer of 2 to 4, L ¹ may be the same or different. When a or c is an integer of 2 to 4, Z ¹ may be the same or different. Z ¹ represents a structure represented by the following general formula (2). ]

[In the general formula ^(2), one one of R 111 ^{~ R 120} are used for binding to ^{L 1} represents a single bond, ^R 111 ^{~ R 118} which is not used in binding to ^{L 1} is, Each independently has the same meaning as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ . R ¹¹⁹ to R ^{120 which} are not used for bonding to L ¹ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trialkyl having 1 to 30 carbon atoms. A silyl group, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 to 50 Are selected from the group consisting of Further, at least one pair of adjacent two of the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ Two substituents may form a ring structure represented by the following general formula (3). Also, ^R 111 ^{~ R 120} which is not used in binding to ^{L 1} may also form a substituent and the ring ^{L 1} or ^{L 1.} ]

[In the general formula (3), y ¹ and y ² represent bonding positions with adjacent groups in R ¹¹¹ to R ¹¹⁸ of the general formula (2). R ¹²¹ to R ¹²⁴ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring forming carbon It is selected from the group consisting of aromatic hydrocarbon groups of 6 to 50 and substituted or unsubstituted heterocyclic groups of 5 to 50 ring-forming atoms. Any one of R ¹¹¹ to R ¹²⁰ that does not form a ring in the general formula (2) and R ¹²¹ to R ^{124 in} the general formula (3) is used for bonding to L ^{1 in the} general formula (1). Single bond. ]

In the general formula (1), L ¹ bonded to Z ¹ is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group-substituted or unsubstituted naphthylene group, and a substituted or unsubstituted group. It is preferably selected from the group consisting of fluorenylene groups.
Among these, L ¹ bonded to Z ¹ is more preferably a single bond or a substituted or unsubstituted phenylene group.

In the general formula (1), L ¹ bonded to Z ¹ is selected from a single bond or a linking group, and when L ¹ is a linking group, L ¹ is represented by the following formula (111) to It is preferably selected from the group consisting of groups represented by (117).

L ¹ in the general formula (1) is selected from either a single bond or a linking group, and when L ¹ is a linking group, L ¹ is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. It is preferably an (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from the group hydrocarbon ring structure. Further, L ¹ is more preferably an (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from an unsubstituted aromatic hydrocarbon ring structure having 6 to 12 ring carbon atoms.

In the general formula (1), it is preferable that at least one of R ¹⁰² , R ¹⁰³ , R ¹⁰⁶ , R ¹⁰⁷ , R ¹⁰⁹ and R ¹¹⁰ is a single bond used for bonding to L ^1. In (1), it is more preferable that at least one of R ¹⁰⁹ and R ¹¹⁰ is a single bond used for bonding to L ¹ .

Among these, in the general formula (1), R ¹⁰⁹ is preferably a single bond used for bonding to L ^1, and the general formula (1) is represented by the following general formula (1a). Is preferred.

In [Formula ^{(1a), R 101 ~ R} 108, R 110, L 1, and ^{Z 1} in ^{R 101 ~ R 108, R 110} , L 1, and ^{Z 1} and interchangeably Formula (1) is there. ]

Further, in the general formula (1), R ¹¹⁰ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. And a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms is more preferable.

In the general formula (1), R ¹⁰¹ to R ¹⁰⁸ are hydrogen atoms, R ¹⁰⁹ is a single bond used for bonding to L ^1, and R ¹¹⁰ is a substituted or unsubstituted ring-forming carbon number of 6 to It is preferably a group selected from 50 aromatic hydrocarbon groups, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and particularly preferably represented by the following general formula (1b): .

[In the general formula (1b), ^{L 1} and ^{Z 1} have the same meanings as ^{L 1,} and ^{Z 1} in the general formula (1). ]

In the general formula (1), R ¹¹⁰ is preferably represented by the following general formula (11). Therefore, it is preferable that the (1b) is represented by the following general formula (1c).

[In the general formula (11), Ar ¹ represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. Indicates the group to be selected. Each Ra has the same meaning as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding with L ¹ in the general formula (1). e represents an integer of 1 to 4. When e is 2 to 4, a plurality of Ra are the same or different. ]

[In the general formula (1c), ^{L 1} and ^{Z 1} have the same meanings as ^{L 1,} and ^{Z 1} in the general formula (1). Further, in the general formula ^(1c), Ar 1, Ra, and d have the same meanings as ^Ar 1, Ra, and d in the general formula (11). ]

In the general formula (1), R ¹¹⁰ is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
The aromatic hydrocarbon group having 6 to 50 ring carbon atoms includes a phenyl group and a condensed aromatic hydrocarbon group having 10 to 50 ring carbon atoms. That is, in the general formula (1), R ¹¹⁰ is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 50 ring carbon atoms.

Furthermore, R ^{110 in the} general formula (1) is preferably selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted fluorenyl group.

In the general formula (1), R ¹¹⁰ is preferably selected from the group consisting of groups represented by the following formulas (121) to (134).

Any one of R ¹¹² to R ¹¹⁴ and R ¹¹⁵ to R ^{117 in} the general formula (2) is preferably a single bond used for bonding to L ^1, and among these, R ¹¹² or R ¹¹⁷ is preferably selected from L ¹ . It is more preferably a single bond used for bonding.

Further, in the general formula (1), Z ¹ is preferably selected from the group consisting of groups represented by the following formulas (141) to (146).

In Formula (1), at least one of ^{L 1} is a linking group, ^R 101 ^{~ R 110} which is not used in binding to ^{L 1} forms a substituent and the ring of ^{L 1} or ^{L 1} and are, or, ^R 111 ^{~ R 120} which is not used in binding to ^{L 1} is preferably also form a substituent and the ring of ^{L 1} or ^{L 1.
R} 101 ^{~ R 110} which is not used in binding to L ¹ is, as a structure forming a substituent and the ring of ^{L 1} or ^{L 1,} for ^example, consider the ^{structure R 101} was formed ^{L 1} and the ring It is done. For example, when L ¹ is represented by the following general formula (L-1), the compound represented by the general formula (1) is a compound having the following general formula (101a) or (101b) as a partial structure. May be.

[In the general formula (L-1), L ¹⁰¹ is selected from a single bond or a linking group, and the linking group is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms. A divalent residue formed by removing two hydrogen atoms from the structure, a divalent residue formed by removing two hydrogen atoms from a substituted or unsubstituted heterocyclic structure having 5 to 50 ring atoms, or It is a divalent residue formed by removing two hydrogen atoms from a structure formed by bonding 2 to 3 of at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure.
R _L ¹⁰¹ is a hydrogen atom or a substituent. ]

[In the general formula (101a) and (101b), R 102 ~ R 108 and R 110 have the same meanings as R 102 ~ R 108 and R 110 in formula (1).
L 101 has the same meaning as L 101 in formula (L-1).
R L 101 ~ R L 103 has the same meaning as R L 101 in formula (L-1). ]

As the ^{structure R} 111 ^{~ R 120} which is not used in binding to ^{L 1} is, forms a substituent and the ring ^{L 1} or ^{L 1,} for example, ^{L 1} is formula (L-1) Can be considered the following partial structures (102a) to (102f).

[In the general formulas (102a) to (102f), R ¹³¹ to R ¹³⁸ and R ¹⁴¹ to R ¹⁴⁶ have the same ^{meanings as} R ¹¹¹ to R ¹²⁰ in the general formula (2).
However, one of R ¹⁴¹ to R ¹⁴⁶ is a single bond bonded to L ¹⁰¹ in the general formula (L-1). ]

In the general formula (2), at least one of a combination of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ When one set of two adjacent substituents forms a ring structure represented by the general formula (3), the general formula (2) is any of the following general formulas (2a) to (2c): It is preferably represented.

Ar ¹⁶¹ to Ar ^{162 in} the general formula (2a), Ar ¹⁷¹ to Ar ¹⁷² in the general formula (2b), and Ar ¹⁸¹ to Ar ¹⁸² in the general formula (2c) each independently represent the general formula (2) The same as R ¹¹⁹ to R ^{120 in the} middle.
1 one of ^R 161 ^{~ R 170} in the formula (2a) is used for binding to ^{L 1} represents a single bond, ^R 161 ^{~ R 170} which is not used in binding to ^{L 1} are each independently Are the same as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ .
 1 one of ^R 171 ^{~ R 180} in the formula (2b) is used for binding to ^{L 1} represents a single bond, ^R 171 ^{~ R 180} which is not used in binding to ^{L 1} are each independently Are the same as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ .
 1 one of ^R 181 ^{~ R 190} in the formula (2c) is used for binding to ^{L 1} represents a single bond, ^R 181 ^{~ R 190} which is not used in binding to ^{L 1} are each independently Are the same as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ .

Next, the general formulas (1) to (3), (1a) to (1c), (101a) to (101b), (102a) to (102f), (2a) to (2c), (11), ( L-1) (hereinafter also referred to as the general formula (1) etc.) will be described.
Specific examples of the substituent described in the general formula (1) and the like include a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted straight chain having 1 to 20 carbon atoms, Branched or cyclic alkyl group, substituted or unsubstituted straight chain, branched chain or cyclic haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted straight chain or branched chain with 1 to 20 carbon atoms Or cyclic alkoxy group, substituted or unsubstituted linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted Or an unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. But It is below.

Examples of the halogen atom in the general formula (1) include fluorine, chlorine, bromine, iodine and the like, and is preferably fluorine.

Examples of the substituted or unsubstituted amino group in the general formula (1) include an amino group substituted with each substituent, and an arylamino group substituted with an aromatic hydrocarbon group is preferable, and a phenyl group is substituted. More preferred is an amino group. Examples of the aromatic hydrocarbon group substituted for the amino group include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the following aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.

The alkyl group having 1 to 20 carbon atoms in the general formula (1) or the like may be linear, branched or cyclic, and examples of the linear or branched alkyl group include a methyl group, Ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl Group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl group, hydroxymethyl Group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2 , 3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro- t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, -Iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl Group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2 , 3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t -Butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 1,2-dinitroethyl group, 2,3-di Nitro-t-butyl group, 1,2,3-trinitropropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,1,3,3,3-hexafluoro-2 -Propyl group and the like.
Examples of the cyclic alkyl group (cycloalkyl group) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 4-methylcyclohexyl group, and 3,5-tetramethylcyclohexyl. Group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
Among the above alkyl groups, an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and an alkyl group having 1 to 4 carbon atoms is particularly preferable. Of these, a methyl group, an isopropyl group, a t-butyl group, and a cyclohexyl group are preferable.

Examples of the linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms include those in which the alkyl group having 1 to 20 carbon atoms is substituted with one or more halogen atoms. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, and a trifluoromethylmethyl group.

The linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms in the general formula (1) or the like is represented by —OY ¹ . Examples of Y ¹ include the alkyl group having 1 to 20 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group. Among the alkoxy groups, an alkoxy group having 1 to 10 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms is more preferable. Particularly preferred is an alkoxy group having 1 to 4 carbon atoms.
Examples of the linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms in the general formula and the like include those in which the alkoxy group having 1 to 20 carbon atoms is substituted with one or more halogen groups. Can be mentioned.

The aryloxy group having 6 to 30 ring carbon atoms in the general formula (1) and the like is represented by —OZ ² . Examples of the Z ² include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the following aromatic hydrocarbon groups having 6 to 50 ring carbon atoms. Examples of the aryloxy group include a phenoxy group.
The arylthio group having 6 to 30 ring carbon atoms in the above general formula and the like is represented by —SZ ³ . Examples of the Z ³ include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the following aromatic hydrocarbon groups having 6 to 50 ring carbon atoms.

Examples of the aromatic hydrocarbon group having 6 to 50 ring carbon atoms in the general formula (1) and the like include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group, and more specifically, a phenyl group. , Naphthyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, pyrenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzo [ c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] phenanthrenyl group, naphtho [1,2-a] triphenylenyl group, dibenzo [a, c] triphenylenyl group, benzo [b] fluoranthenyl Group, and the like. Among the above aromatic hydrocarbon groups, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms is preferable, an aromatic hydrocarbon group having 6 to 20 ring carbon atoms is more preferable, and an aromatic hydrocarbon group having 6 to 12 ring carbon atoms is more preferable. Aromatic hydrocarbon groups are particularly preferred.

Examples of the heterocyclic group having 5 to 50 ring atoms in the general formula (1) include a non-condensed heterocyclic ring and a condensed heterocyclic ring, and more specifically, a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group. Group, isoindolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthate Lorinyl group, thienyl group, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring , Furan ring, thiophene ring, oxazole ring, oxy Diazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, a group formed from benzo [c] dibenzofuran ring and the like. Among the above heterocyclic groups, a heterocyclic group having 5 to 30 ring atoms is preferable, a heterocyclic group having 5 to 20 ring atoms is more preferable, and a heterocyclic group having 5 to 12 ring atoms is particularly preferable. .

In the general formula (1), R ¹⁰¹ to R ¹¹⁰ that are not used for bonding with L ¹ are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
When R ¹⁰⁹ is a condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms, more preferably, a 1-naphthyl group, a 2-naphthyl group, a 1-anthryl group, a 2-anthryl group, a 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group and 4-methyl-1-anthryl group.

In the general formula (1), when L ¹ is a linking group, a substituted or unsubstituted (a + 1) -valent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, a substituted or unsubstituted (a + 1) -valent Or a divalent group formed by combining 2 to 4 of these aromatic hydrocarbon groups or heterocyclic groups.
Specific examples of the (a + 1) -valent aromatic hydrocarbon group having 6 to 50 ring carbon atoms include those listed above as the aromatic hydrocarbon group having 6 to 50 ring carbon atoms. Based on this.
Further, specific examples of the (a + 1) -valent heterocyclic group having 5 to 50 ring atoms include the above-mentioned heterocyclic groups having 5 to 50 ring-forming atoms as the (a + 1) -valent group. The thing which was done is mentioned.
When L ¹ is an (a + 1) -valent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, more preferred aromatic hydrocarbon groups are phenyl, biphenyl, naphthyl, 9,9-dimethylfurane. The thing which made the oleenyl group into bivalent group is mentioned.
When L ¹ is an (a + 1) -valent heterocyclic group having 6 to 50 ring atoms, more preferable heterocyclic group is a pyridyl group, pyrimidyl group, dibenzofuranyl group, or carbazolyl group as a divalent group. Things.

R ¹¹¹ to R ¹¹⁸ that are not used for bonding with L ¹ in the general formula (2) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.
R ¹¹⁹ to R ¹²⁰ in the general formula (2) are preferably alkyl groups, more preferably methyl groups, and even more preferably R ¹¹⁹ and R ¹²⁰ are both methyl groups.
R ¹²¹ to R ¹²⁴ in the general formula (3) are more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

In the general formula (11), Ar ¹ is particularly preferably a phenyl group, a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, or a biphenyl group.
Ra is particularly preferably a hydrogen atom, an aromatic hydrocarbon group, or a heterocyclic group.

In the present invention, “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. “Ring-forming atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
In the present invention, the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).

In the case of “substituted or unsubstituted”, examples of the substituent include the aromatic hydrocarbon group, the heterocyclic group, and the alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group) as described above. , Alkoxy group, aryloxy group, aralkyl group, haloalkoxy group, alkylsilyl group, dialkylarylsilyl group, alkyldiarylsilyl group, triarylsilyl group, halogen atom, cyano group, hydroxyl group, nitro group, and carboxy group Can be mentioned. In addition, an alkenyl group and an alkynyl group are also included.
Among the substituents mentioned here, an aromatic hydrocarbon group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and more preferable in the description of each substituent. The specific substituents are preferred.
The term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
In the present specification, the “carbon number ab” in the expression “substituted or unsubstituted XX group having carbon number ab” represents the number of carbons when the XX group is unsubstituted. The number of carbon atoms of the substituent when the XX group is substituted is not included.
In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

In the organic EL device of the present invention, among the compounds represented by the general formulas (1) and (1a) to (1c), Z ¹ , L ¹ , R ¹¹⁰ , Ar ¹ and Ra do not contain a hetero atom. It is preferable to consist only of hydrocarbons. Accordingly, among the substituents described in the general formula (1) and the like, a group that does not contain a heteroatom is preferable, and a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring formation. An aromatic hydrocarbon group having 6 to 50 carbon atoms is more preferable.
In addition, when Z ¹ , L ¹ , R ¹¹⁰ , Ar ¹ , and Ra have a substituent, the skeleton of the substituent preferably does not include a hetero atom and consists only of a hydrocarbon group.
Furthermore, it is particularly preferable that the compounds represented by the general formulas (1) and (1a) to (1c) are hydrocarbon compounds composed only of hydrocarbons.

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

-Dopant material As a dopant material used for the organic EL element of this invention, a fluoranthene derivative, a chrysene derivative, and a pyrene derivative can be used, for example.
As the fluoranthene derivative, a compound represented by the following general formula (31) can be used.

[In the general formula (31),
R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ³¹¹ are each independently a hydrogen atom, hydroxyl group, cyano group, nitro group, carboxyl group, substituted or unsubstituted silyl group, substituted or unsubstituted An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, and a substituted or unsubstituted ring forming carbon number having 6 to 30 carbon atoms. Aryloxy group, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms An amino group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 to 5 Selected from the first group of 50 heterocyclic groups.
In the general formula (31), R ³⁰³ is selected from the second group constituted by removing hydrogen atoms from the first group shown for R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ^311. It is.
In the general formula (31), R ³⁰⁴ is constituted by removing an aromatic hydrocarbon group and a heterocyclic group from the first group shown for R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ^311. Selected from the third group.
In the general formula (31), R ³⁰⁷ and R ³¹² are each independently a hydrogen atom or a hydroxyl group from the first group shown for R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ^311. , A cyano group, a nitro group, a carboxyl group, and a silyl group.
In the general formula (31), R ³⁰¹ and R ³⁰² , R ³⁰² and R ³⁰³ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ³⁰⁷ , R ³⁰⁷ and R ³⁰⁸ , R ³⁰⁸ and R ³⁰⁹ , R ³⁰⁹ and R ³¹⁰ , R ³¹⁰ and R ³¹¹ , and R ³¹¹ and R ³¹² may combine with each other to form a saturated or unsaturated ring, or may not form a saturated or unsaturated ring, Substituted or unsubstituted. ]

In the general formula (31),
The second group is a group constituted by removing a hydrogen atom from the first group, that is, the second group is a hydroxyl group, a cyano group, a nitro group, a silyl group, a carboxyl group, a substituted or unsubstituted group. Silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted An aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, a substituted or unsubstituted ring An arylamino group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 Consisting heterocyclic group 50.

In the general formula (31),
The third group is a group constituted by removing the aromatic hydrocarbon group and the heterocyclic group from the first group, that is, the third group includes a hydrogen atom, a hydroxyl group, a cyano group, a nitro group, a silyl group. Group, carboxyl group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon number 7 to 30 aralkyl groups, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted arylthio groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 2 to 50 carbon atoms It consists of a carbonyl group and a substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms.

In the general formula (31),
The fourth group is a group constituted by removing the hydrogen atom, hydroxyl group, cyano group, nitro group, carboxyl group and silyl group from the first group, that is, the fourth group is substituted or unsubstituted. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted ring structure having 6 to 30 carbon atoms Aryloxy group, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms And a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

R ^{304 in the} general formula (31) is preferably a hydrogen atom.
R ³⁰⁷ and R ^{312 in} the general formula (31) are preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms. Further, R ³⁰⁷ and R ^{312 in} the general formula (31) are preferably substituted or unsubstituted phenyl groups.

^{Alternatively} , R ³⁰¹ to R ³⁰² , R ³⁰⁴ to R ³⁰⁶ and R ³⁰⁸ to R ^{311 in the} general formula (31) are hydrogen atoms, and R ³⁰³ , R ³⁰⁷ and R ^{312 in the} general formula (31) are substituted. Alternatively, it is preferably an unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.

R ³⁰¹ to R ³⁰² , R ³⁰⁴ to R ³⁰⁶ and R ³⁰⁸ to R ^{311 in the} general formula (31) are hydrogen atoms, and R ³⁰⁷ and R ^{312 in} the general formula (31) are substituted or unsubstituted ring formation. An aromatic hydrocarbon group having 6 to 50 carbon atoms, wherein R ^{303 in the} general formula (31) is —Ar ³¹ —Ar ³² , and Ar ³¹ and Ar ³² are each independently substituted or unsubstituted. An aromatic hydrocarbon group having 6 to 50 ring carbon atoms is preferable.
In this case, it is preferable that Ar ³¹ or Ar ³² is an aromatic hydrocarbon group having a cyano group as a substituent.

Alternatively, R ³⁰¹ to R ³⁰² , R ³⁰⁴ to R ³⁰⁶ and R ³⁰⁸ to R ³¹¹ in the general formula (31) are hydrogen atoms, and R ³⁰⁷ and R ^{312 in} the general formula (31) are substituted or not. A substituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, R ^{303 in the} general formula (31) is —Ar ³¹ —Ar ³² —Ar ³³ , and Ar ³¹ , Ar ³² and Ar ³³ are Independently, it is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms.
In this case, Ar ³¹ , Ar ³² or Ar ³³ is preferably an aromatic hydrocarbon group having a cyano group as a substituent.

Specific examples of the groups listed in the first to fourth groups selected for R ³⁰¹ to R ³¹² of the general formula (31) include those exemplified in the description of the general formula (1) and the like, and the following. The following are mentioned.

The aralkyl group having 7 to 30 carbon atoms is represented by —R ^X —R ^Y. Examples of this R ^X include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms. Examples of this R ^Y include aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the above aromatic hydrocarbon groups having 6 to 50 ring carbon atoms. In this aralkyl group, the aromatic hydrocarbon group moiety has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. In this aralkyl group, the alkyl group moiety has 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms, and still more preferably 1 to 6 carbon atoms. Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- (1-pyrrolyl) ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group P-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o -Cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group.

Examples of the silyl group include an unsubstituted silyl group, an alkylsilyl group having 1 to 30 carbon atoms, and an arylsilyl group having 6 to 60 carbon atoms.

Examples of the alkylsilyl group having 1 to 30 carbon atoms include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, specifically, a trimethylsilyl group, a triethylsilyl group, a tri-n group. -Butylsilyl group, tri-n-octylsilyl group, triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t-butylsilyl group, diethyl Examples include isopropylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triisopropylsilyl group and the like. The three alkyl groups may be the same or different from each other.
Examples of the arylsilyl group having 6 to 60 ring carbon atoms include arylsilyl group, alkylarylsilyl group, dialkylarylsilyl group, diarylsilyl group, alkyldiarylsilyl group, and triarylsilyl group. A plurality of aromatic hydrocarbon groups or alkyl groups may be the same or different.

The dialkylarylsilyl group has, for example, two alkyl groups exemplified as the alkyl group having 1 to 20 carbon atoms, and among the aromatic hydrocarbon groups having 6 to 50 ring carbon atoms, the ring forming carbon number is 6 And a dialkylarylsilyl group having 1 to 30 aromatic hydrocarbon groups. The carbon number of the dialkylarylsilyl group is preferably 8-30. The two alkyl groups may be the same or different.
The alkyldiarylsilyl group has, for example, one alkyl group exemplified as the alkyl group having 1 to 20 carbon atoms, and among the aromatic hydrocarbon groups having 6 to 50 ring carbon atoms, the ring forming carbon number is 6 And alkyldiarylsilyl groups having 2 to 30 aromatic hydrocarbon groups. The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms. The two aromatic hydrocarbon groups may be the same or different from each other.
Examples of the triarylsilyl group include a triarylsilyl group having three aromatic hydrocarbon groups having 6 to 30 ring carbon atoms among the above aromatic hydrocarbon groups having 6 to 50 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30. The three aromatic hydrocarbon groups may be the same or different from each other.
Examples of such an arylsilyl group include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl-t-butylsilyl group, and a triphenylsilyl group.

The alkoxycarbonyl group is represented as —COOY ′, and examples of Y ′ include the same as the alkyl group.
The arylamino group is represented by —NAr ¹ Ar ^2, and specific examples of Ar ¹ and Ar ² include, independently of each other, an aromatic hydrocarbon group having 6 to 50 ring carbon atoms and 6 to 6 ring forming carbon atoms. This is the same as the group explained for the 30 aromatic hydrocarbon group. One of Ar ¹ and Ar ² may be a hydrogen atom.

Specific examples of the fluoranthene derivative represented by the general formula (31) are shown below, but the present invention is not limited to these exemplified compounds.

As a dopant material used in the organic EL device of the present invention, a chrysene derivative represented by the following general formula (41) can also be used.

[In the general formula (41),
R ⁴⁰⁰ to R ⁴⁰⁹ are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring forming carbon number. 6 to 50 aromatic hydrocarbon groups are shown.
Ar ⁴⁰¹ to Ar ⁴⁰⁴ each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. When Ar ⁴⁰¹ to Ar ⁴⁰⁴ have an alkyl group as a substituent, each of them has at least two alkyl groups. ]

In the general formula (41), R ⁴⁰⁰ to R ⁴⁰⁹ are preferably hydrogen atoms.
In the general formula (41), each of Ar ⁴⁰¹ to Ar ⁴⁰⁴ preferably has two or more substituents.

It is preferable that the general formula (41) is further represented by the following general formula (42).

In general formula (42),
A ₁ to A ₄ each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted group; Aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or unsubstituted ring-forming carbon It is selected from the first group consisting of an aromatic hydrocarbon group of 6 to 50 and a substituted or unsubstituted heterocyclic group of 5 to 50 ring-forming atoms.
p, q, r and s are each independently an integer of 0 to 3, and when p, q, r and s are each 2 or more, A ₁ to A ₄ are the same or different.

In the general formula (42),
A ₅ to A ₁₂ each independently represent a halogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, or a substituted or unsubstituted ring-forming carbon. An aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a substituted or unsubstituted ring carbon number of 6 to 6 It is selected from 50 aromatic hydrocarbon groups and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms.
A ₅ and A ₆ , A ₇ and A ₈ , A ₉ and A ₁₀ , A ₁₁ and A ₁₂ may be connected to each other to form a saturated or unsaturated ring.

In the general formula (42), it is more preferable that A ₅ to A ₁₂ are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In the general formulas (41) and (42), the halogen atom, alkyl group, alkoxy group, aryloxy group, aralkyl group, amino group, silyl group, aromatic hydrocarbon group, and heterocyclic group may be the above general formula (1). ) And the groups described in the general formula (31).

Specific examples of the chrysene derivatives represented by the general formula (41) and the general formula (42) are shown below, but the present invention is not limited to these exemplified compounds.

As a dopant material used in the organic EL device of the present invention, a pyrene derivative represented by the following general formula (51) can also be used.

[In the general formula (51),
R ⁵⁰¹ to R ⁵⁰⁸ are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring forming carbon number. Represents an aromatic hydrocarbon group having 6 to 50, and Ar ⁵⁰¹ to Ar ⁵⁰⁴ each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number. 5 to 50 heterocyclic groups are shown.
However, at least one of Ar ⁵⁰¹ to Ar ⁵⁰⁴ is a heterocyclic group represented by the following formula (52). ]

[In the general formula (52),
R ⁵¹¹ to R ⁵¹⁷ are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted An alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 50 ring atoms. The heterocyclic group of is shown.
R ⁵¹¹ and R ⁵¹² , R ⁵¹² and R ⁵¹³ , R ⁵¹³ and R ⁵¹⁴ , R ⁵¹⁵ and R ⁵¹⁶ , and R ⁵¹⁶ and R ⁵¹⁷ may be bonded to each other to form a saturated or unsaturated ring. These rings may be substituted.
X ⁵¹ is selected from either an oxygen atom or a sulfur atom.
y ⁵¹ is a single bond bonded to the nitrogen atom of the general formula (51). ]

In the general formula (51), Ar ⁵¹ and Ar ⁵³ are preferably a heterocyclic group represented by the general formula (52).
In the general formula (51), R ⁵⁰¹ to R ⁵⁰⁸ are preferably hydrogen atoms.
Or R ⁵⁰² and R ^{506 in} the general formula (51) are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, R ⁵⁰¹ , R ⁵⁰³ , R ⁵⁰⁴ , R ⁵⁰⁵ , R ⁵⁰⁷ , and R ⁵⁰⁸ are more preferably hydrogen atoms.
Further, it is preferable that the ^{X 51} in formula (52) is an oxygen atom.
Particularly preferably, Ar ⁵¹ to Ar ⁵⁴ are represented by the general formula (52), and X ⁵¹ is an oxygen atom.

In the general formulas (51) and (52), the halogen atom, aromatic hydrocarbon group, heterocyclic group, alkyl group, alkoxy group, aryloxy group, arylthio group, arylamino group, and silyl group may be the above general formula ( Examples thereof include groups described in 1) and the like and the general formula (31).

The alkenyl group having 2 to 20 carbon atoms in the general formula (52) may be linear, branched or cyclic, such as vinyl, propenyl, butenyl, oleyl, eicosapentaenyl, docosahexa Examples include enyl, styryl, 2,2-diphenylvinyl, 1,2,2-triphenylvinyl, 2-phenyl-2-propenyl and the like. Among the alkenyl groups described above, a vinyl group is preferable.

The alkynyl group having 2 to 20 carbon atoms in the general formula (52) may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like. Of the alkynyl groups described above, an ethynyl group is preferred.

The saturated or unsaturated ring formed by combining R ⁵¹¹ and R ⁵¹² , R ⁵¹² and R ⁵¹³ , R ⁵¹³ and R ⁵¹⁴ , R ⁵¹⁵ and R ⁵¹⁶ , and R ⁵¹⁶ and R ⁵¹⁷ together includes cyclobutane, cyclo Cycloalkanes having 4 to 12 ring carbon atoms such as pentane, cyclohexane, adamantane and norbornane, cycloalkens having 4 to 12 ring carbon atoms such as cycloalkane, cyclobutene, cyclopentene, cyclohexene, cycloheptene and cyclootaten, cyclohexadiene, etc. Such as cyclohexadiene, cyclooctadiene, and the like, and cycloannolecadiens having 6 to 12 ring carbon atoms, aromatic rings having 6 to 50 ring carbon atoms such as benzene, naphthalene, phenanthrene, anthracene, pyrene, thalicene, and acenaphthylene. Can be mentioned. In addition, examples of the substituent are the same as those described above.

Specific examples of the pyrene derivative represented by the general formula (51) are shown below, but the present invention is not limited to these exemplified compounds.

(Hole injection / transport layer)
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and a compound having a high hole mobility and a low ionization energy is used.
As a material for forming the hole injecting / transporting layer, a material that transports holes to the light emitting layer with lower electric field strength is preferable. For example, an aromatic amine compound is preferably used.

(Electron injection / transport layer)
The electron injection / transport layer is a layer that assists injection of electrons into the light emitting layer and transports it to the light emitting region, and a compound having a high electron mobility is used.
As the compound used for the electron injecting / transporting layer, in the present embodiment, it is preferable to use a compound represented by the following general formula (21).

[In the general formula (21),
X ¹ to X ³ are each independently a nitrogen atom or CR ²⁰¹ . However, at least one of X ¹ to X ³ is a nitrogen atom. R ²⁰¹ has the same ^meaning as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1). Ar ²⁰¹ is represented by the following general formula (22). Ar ²⁰² and Ar ²⁰³ are each independently represented by the following general formula (22), a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring It is a heterocyclic group having 5 to 50 atoms. ]

The substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and the substituted or unsubstituted heterocyclic group having 5 to 5 ring atoms in the general formula (21) are represented by the general formula (1) and the like. It is synonymous with the specific example of the substituent as described in above.

[In the general formula (22),
HAr is represented by the following general formula (23). d is 1 or 2. L ² is a single bond or a linking group comprising a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms. When d is 1, L ² is a single bond or a divalent linking group. When d is 2, L ² is a trivalent linking group, and HAr is the same or different. ]

[In the general formula (23), X ¹¹ to X ¹⁸ are each independently a carbon atom bonded to the nitrogen atom, CR ²⁰² , or L ² with a single bond.
Y ¹ represents an oxygen atom, a sulfur ^{atom, N-R 203, CR 204} R 205, nitrogen atom bonded by a single bond to ^{L 2,} or, in ^{CR 206} for coupling with a single bond to ^{L 2} is there.
R ²⁰² to R ²⁰⁶ have the same ^meanings as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1).
However, the bond to L ² is any ^one of carbon atoms from X ¹¹ to X ¹⁸ , carbon atoms from R ²⁰³ to R ²⁰⁵ , nitrogen atoms in Y ¹ , and carbon atoms in Y ¹ . is there. ]

When Y ¹ is a nitrogen atom bonded to N—R ²⁰³ and L ² with a single bond, a carbazole skeleton is formed. The carbazole skeleton bonded to L ² with a single bond is particularly easy to make a structure bonded at the 9-position, and it is difficult to make a structure in the order of the 3-position, 2-position, 4-position, and 1-position.
When Y ¹ is an oxygen atom, a dibenzofuran skeleton is formed. A dibenzofuran skeleton bonded to L ² by a single bond is particularly easy to make a structure bonded at the 2-position and a structure bonded at the 4-position, respectively, and it is difficult to make them in the order of the 3-position and the 1-position.

In the general formula (21), it is preferable that at least two of X ¹ to X ³ are nitrogen atoms.
Further, the above general formula (21), more preferably ^{X 1} and ^{X 2} is a nitrogen atom. The general formula in this case is represented by the following general formula (21a).

Ar ²⁰² , Ar ²⁰³ , L ² , HAr, and d in the general formula (21a) have the same meanings as the substituents in the general formula (21) and the general formula (22).

In the general formula (21a), when d is 1, it is represented by the following general formula (21b).

Ar ²⁰² , Ar ²⁰³ , L ² and HAr in the general formula (21b) have the same meanings as the substituents in the general formula (21) and the general formula (22).

In the general formula (21a), when d is 2, it is represented by the following general formula (21c).

Ar ²⁰² , Ar ²⁰³ , and L ² in the general formula (21c) have the same meanings as the substituents in the general formula (21) and the general formula (22). Further, in the above general formula (21c), HAr ^1, and, HAr ² are the same as HAr in formula (22), HAr ¹ and HAr ² may be the same or different.

Further, ^{Y 1} in the general formula (23) is preferably an oxygen atom. At this time, CR ²⁰² is preferable for X ¹¹ to X ¹⁸ other than the carbon atom bonded to L ² . Furthermore, ^{X 18} from ^{X 11} other than carbon atom bonded to the ^{L 2 is} more preferably ^{R 202} of ^{CR 202} is a hydrogen atom.

In addition, L ² in the general formula (22) is preferably a divalent or trivalent residue of a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 12 ring carbon atoms.
Among these, L ² is more preferably a divalent or trivalent residue of benzene, biphenyl or naphthalene.

Moreover, it is preferable that d in the said General formula (22) is 1 or 2, and each Y < ¹ > in the said General formula (23) is a nitrogen atom. Of these, when d is 1, Y ^{1 in the} general formula (23) is bonded to L ² with a single bond when d is 2 and Y ¹ in the general formula (23) is bonded to L ² . More preferably, it is a nitrogen atom.

Moreover, it is preferable that d in the said General formula (22) is 1 or 2, and each Y < ¹ > in the said General formula (23) is an oxygen atom. Among these, when d is 1, any one of X ¹¹ , X ¹⁴ , X ¹⁵ or X ^{18 in} the general formula (23), and when d is 2, one X of the general formula (23) ¹¹ , X ¹⁴ , X ^15, or X ¹⁸ , and the other carbon of any one of X ¹¹ , X ¹⁴ , X ^15, or X ^{18 in} the general formula (23) are bonded to L ² with a single bond. More preferably it is an atom.

Further, the HAr of the general formula (22) is preferably selected from the group consisting of groups represented by the following formulas (221a) to (221d).

In the general formula (21), Ar ²⁰² is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms.

Ar ²⁰² in the general formula (21) is preferably a substituted or unsubstituted phenyl group. In the case where Ar ²⁰² in the general formula (21) is a substituted or unsubstituted phenyl group, X ¹ and X ² are more preferably nitrogen atoms, and Ar ²⁰² is a phenyl group. More preferably, it is represented by the following general formula (21d).

Ar ²⁰³ , L ² and HAr in the general formula (21d) have the same meanings as the substituents in the general formula (21) and the general formula (22).

Ar ²⁰³ in the general formula (21) is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring carbon atoms. preferable.
Among these, it is preferable that Ar ²⁰³ in the general formula (21) is a phenyl group, a biphenyl group, or a naphthyl group.

In addition, Ar ²⁰³ in the general formula (21) is preferably selected from the group consisting of groups represented by the following formulas (211a) to (211n).

Among these, Ar ²⁰³ in the general formula (21) is preferably selected from the group consisting of groups represented by the following formulas (212a) to (212h).

Ar ²⁰³ in the general formula (21) is preferably a substituted or unsubstituted nitrogen-containing heterocyclic group having 5 to 30 ring atoms.

The general formula (22) is preferably selected from the group consisting of groups represented by the following formulas (222a) to (222f).

The general formula (22) is preferably selected from the group consisting of groups represented by the following formulas (223a) to (223g).

Examples of the compound represented by the general formula (21) include the following compounds.

In the present embodiment, the electron injection / transport layer including the compound represented by the general formula (21) is preferably provided adjacent to the light emitting layer.
Further, a plurality of electron injection / transport layers may be provided, and even in that case, the electron injection / transport layer containing the compound represented by the general formula (21) may be provided adjacent to the light emitting layer. Is preferred.

In the organic EL device of the present invention, an organic compound other than the light emitting layer can be used by selecting any compound from the materials used in the conventional organic EL device in addition to the compounds exemplified above.

(substrate)
The organic EL element of the present invention is produced on a light-transmitting substrate. Here, the light-transmitting 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 nm to 700 nm of 50% or more.
Specifically, a glass plate, a polymer plate, etc. are mentioned.
Examples of the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
Examples of the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.

(Anode and cathode)
The anode of the organic EL element plays a role of injecting holes into the hole injection layer, 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 include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
The anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
When light emitted from the light emitting layer is extracted from the anode as in the present embodiment, it is preferable that the light transmittance in the visible region of the anode be greater than 10%. The sheet resistance of the anode is preferably several hundred Ω / □ (ohm / square) or less. The film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 μm, preferably 10 nm to 200 nm.

As the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer, the electron transport layer, or the light emitting layer.
The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
Similarly to the anode, the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, the aspect which takes out light emission from a cathode side is also employable. Moreover, the aspect which takes out light emission from a light emitting layer from a cathode side is also employable. When light emitted from the light emitting layer is extracted from the cathode side, it is preferable that the light transmittance in the visible region of the cathode be greater than 10%.
The sheet resistance of the cathode is preferably several hundred Ω / □ or less.
The layer thickness of the cathode depends on the material, but is usually selected in the range of 10 nm to 1 μm, preferably 50 nm to 200 nm.

(Method for forming each layer of organic EL element)
The formation method of each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. The organic layer used in the organic EL device of the present invention is formed by a vacuum deposition method, a molecular beam deposition method (MBE method, MBE; Molecular Beam Epitaxy), a solution dipping method in a solvent, a spin coating method, a casting method, or a bar coating method. It can be formed by a known method using a coating method such as a roll coating method.

(Thickness of each layer of organic EL element)
The thickness of the light emitting layer is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. By setting the thickness of the light emitting layer to 5 nm or more, it becomes easy to form the light emitting layer and adjust the chromaticity. By setting the film thickness of the light emitting layer to 50 nm or less, an increase in driving voltage can be suppressed.
The film thickness of each of the other organic layers is not particularly limited, but is usually preferably in the range of several nm to 1 μm. By making such a film thickness range, defects such as pinholes caused by the film thickness being too thin are prevented, and an increase in driving voltage caused by the film thickness being too thick is suppressed, resulting in deterioration of efficiency. Can be prevented.

[Modification of Embodiment]
In addition, this invention is not limited to the above-mentioned embodiment, The change in the range which can achieve the objective of this invention, improvement, etc. are included in this invention.

The light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer contains the compound represented by the general formula (1), and the other light emitting layers are fluorescent light emitting layers. Alternatively, a phosphorescent light emitting layer may be used.
In addition, when the organic EL element has a plurality of light emitting layers, these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.

In the present invention, it is also preferable that the light emitting layer contains a charge injection auxiliary material.
When a light emitting layer is formed using a host material having a wide energy gap, the difference between the ionization potential (Ip) of the host material and Ip of the hole injection / transport layer, etc. increases, and holes are injected into the light emitting layer. This may make it difficult to increase the driving voltage for obtaining sufficient luminance.
In such a case, by adding a hole injection / transport charge injection auxiliary material to the light emitting layer, hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.

As the charge injection auxiliary material, for example, a general hole injection / transport material or the like can be used.
Specific examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, fluorenone derivatives, hydrazone derivatives, stilbenes. Derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), and the like can be given.

Examples of the hole-injecting material include those described above, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds are preferred.

In addition, for example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter abbreviated as NPD) having two condensed aromatic rings in the molecule, or triphenylamine 4,4 ′, 4 ″ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA), etc., in which three units are connected in a starburst type. it can.
A hexaazatriphenylene derivative or the like can also be suitably used as the hole injecting material.
In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.

[Electronics]
The organic EL element of the present invention can be suitably used by being mounted on an electronic device such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicle lamp.

Next, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to the description of these examples.

[Example of manufacturing organic EL element]
Example 1
A glass substrate with an ITO transparent electrode of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
The glass substrate with the ITO transparent electrode line after washing is attached to the substrate holder of the vacuum evaporation apparatus, and the following compound (HA) is first coated so as to cover the transparent electrode on the surface on which the ITO transparent electrode line is formed. A HA film having a thickness of 5 nm was formed by vapor deposition to form a hole injection layer.
Next, the following compound HT1 was deposited as a first hole transport material on this HA film to form an HT1 film having a thickness of 80 nm, thereby forming a first hole transport layer.
Next, on the HT1 film, the following compound HT2 was deposited as a second hole transport material to form an HT2 film having a thickness of 15 nm, thereby forming a second hole transport layer.
Further, a compound BH2 was vapor-deposited on the HT2 film to form a light emitting layer having a thickness of 25 nm. At the same time, the following compound BD was co-deposited as a fluorescent material. The concentration of Compound BD was 5.0% by mass. This co-deposited film functions as a light emitting layer.
And on this light emitting layer, the following compound ET1 was vapor-deposited and the ET1 film | membrane with a film thickness of 20 nm was formed into a film, and the 1st electron carrying layer was formed.
Subsequently, the following compound ET2 was vapor-deposited on the ET1 film to form an ET2 film having a thickness of 5 nm, thereby forming a second electron transport layer.
Next, LiF was deposited on the ET2 film at a deposition rate of 0.1 angstrom / min to form a 1 nm-thick LiF film to form an electron injecting electrode (cathode).
And metal Al was vapor-deposited on this LiF film | membrane, the metal Al film | membrane with a film thickness of 80 nm was formed into a film, and the metal Al cathode was formed.

The compounds used for the production of organic EL devices are shown below.

Comparative examples 1 to 3
The organic EL elements of Comparative Examples 1 to 3 are at least one of the host material for the light emitting layer, the second hole transport material for the second hole transport layer, and the first electron transport material for the first electron transport layer in Example 1. Was prepared in the same manner as in Example 1 except that the compound was changed to the compounds shown in Table 1.

[Evaluation of organic EL elements]
A voltage was applied to the produced organic EL device so that the current density was 10 mA / cm ^2, and CIE 1931 chromaticity, current efficiency L / J, external quantum efficiency EQE, and main peak wavelength λ _p were evaluated. The results are shown in Table 2. Each evaluation item of drive voltage, current efficiency L / J, and external quantum efficiency EQE is represented by the ratio of the values of Example 1 and Comparative Examples 2 to 3 to the value of Comparative Example 1.

The luminance when a voltage was applied to the device so that the current density was 10 mA / cm ² was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta).

CIE1931 chromaticity CIE1931 chromaticity coordinates (x, y) when a voltage was applied to the device so that the current density was 10 mA / cm ² were measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta).

・ Current efficiency L / J
The spectral radiance spectrum when a voltage was applied to the device so that the current density was 10 mA / cm ² was measured with the above spectral radiance meter, and the current efficiency (unit: cd / A) was calculated from the obtained spectral radiance spectrum. ) Was calculated.

・ External quantum efficiency EQE
From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit:%) was calculated on the assumption that Lambtian radiation was performed.

・ Main peak wavelength λ _p
The main peak wavelength λ _p was determined from the obtained spectral radiance spectrum.

As shown in Table 2, the organic EL device of Example 1 was found to be an organic EL device having higher luminous efficiency than the organic EL devices of Comparative Examples 1 to 3. For example, the organic EL device of Example 1 has an external quantum efficiency EQE of about 1.275 times that of the organic EL device of Comparative Example 1, that is, about 27.5%.

DESCRIPTION OF SYMBOLS 1 ... Organic EL element 2 ... Substrate 3 ... Anode 4 ... Cathode 5 ... Light emitting layer 6 ... Hole transport layer 7 ... Electron transport layer 10 ... Organic layer

Claims (38)

The anode,
A cathode provided opposite to the anode;
A light emitting layer provided between the cathode and the anode and containing a compound represented by the following general formula (1);
An organic electroluminescence device comprising: an electron transport layer that is provided between the light emitting layer and the cathode and includes a compound represented by the following general formula (21).

[In the general formula (1),
a, b and c each represents an integer of 1 to 4;
Any one of R ¹⁰¹ to R ¹¹⁰ is a single bond and is used for bonding to L ¹ ;
R ¹⁰¹ to R ¹¹⁰ not used for bonding to L ¹ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon number of 1 to 20 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring carbon atoms, and substituted or unsubstituted arylthio groups having 6 to 20 ring carbon atoms. Selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
L ¹ is selected from either a single bond or a linking group, and when L ¹ is a linking group, L ¹ is a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 50 ring carbon atoms. (A + 1) hydrogen atoms can be removed (a + 1) valent residues, substituted or unsubstituted heterocyclic structures with 5 to 50 ring atoms (a + 1) hydrogen atoms can be removed (a + 1) A (a + 1) valence obtained by removing (a + 1) hydrogen atoms from a valent residue or a structure formed by bonding 2 to 4 at least one of the aromatic hydrocarbon ring structure and the heterocyclic structure Is the residue. If L ¹ is a linking group, ^R 101 ^{~ R 110} which is not used in binding to ^{L 1} may also form a substituent and the ring ^{L 1} or ^{L 1.} When c is an integer of 2 to 4, L ¹ may be the same or different. When a or c is an integer of 2 to 4, Z ¹ may be the same or different.
Z ¹ represents a structure represented by the following general formula (2). ]

[In the general formula (2),
1 one of R ¹¹¹ ~ ^{R 120} are used for binding to ^{L 1} represents a single bond, ^R 111 ^{~ R 118} which is not used in binding to ^{L 1} are each independently a bond between ^{L 1} It is synonymous with R ¹⁰¹ to R ¹¹⁰ that are not used in the above. R ¹¹⁹ to R ^{120 which} are not used for bonding to L ¹ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted trialkyl having 1 to 30 carbon atoms. A silyl group, a substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted ring atom number of 5 to 50 Are selected from the group consisting of Further, at least one pair of adjacent two of the combinations of R ¹¹¹ and R ¹¹² , R ¹¹² and R ¹¹³ , R ¹¹³ and R ¹¹⁴ , R ¹¹⁵ and R ¹¹⁶ , R ¹¹⁶ and R ¹¹⁷ , and R ¹¹⁷ and R ¹¹⁸ Two substituents may form a ring structure represented by the following general formula (3). Also, ^R 111 ^{~ R 120} which is not used in binding to ^{L 1} may also form a substituent and the ring ^{L 1} or ^{L 1.} ]

[In the general formula (3),
y ¹ and y ² represent bonding positions with adjacent groups in R ¹¹¹ to R ¹¹⁸ of the general formula (2).
R ¹²¹ to R ¹²⁴ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring forming carbon It is selected from the group consisting of aromatic hydrocarbon groups of 6 to 50 and substituted or unsubstituted heterocyclic groups of 5 to 50 ring-forming atoms.
Any one of R ¹¹¹ to R ¹²⁰ that does not form a ring in the general formula (2) and R ¹²¹ to R ^{124 in} the general formula (3) is used for bonding to L ^{1 in the} general formula (1). Single bond. ]

[In the general formula (21),
X ¹ to X ³ are each independently a nitrogen atom or CR ²⁰¹ . However, at least one of X ¹ to X ³ is a nitrogen atom. R ²⁰¹ has the same ^meaning as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1). Ar ²⁰¹ is represented by the following general formula (22). Ar ²⁰² and Ar ²⁰³ are each independently represented by the following general formula (22), a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring It is a heterocyclic group having 5 to 50 atoms. ]

[In the general formula (22),
HAr is represented by the following general formula (23).
d is 1 or 2.
L ² is a single bond or a linking group comprising a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms. When d is 1, L ² is a single bond or a divalent linking group. When d is 2, L ² is a trivalent linking group, and HAr is the same or different. ]

[In the general formula (23),
X ¹¹ to X ¹⁸ are each independently a carbon atom bonded to the nitrogen atom, CR ²⁰² , or L ² with a single bond.
Y ¹ represents an oxygen atom, a sulfur ^{atom, N-R 203, CR 204} R 205, nitrogen atom bonded by a single bond to ^{L 2,} or, in ^{CR 206} for coupling with a single bond to ^{L 2} is there.
R ²⁰² to R ²⁰⁶ have the same ^meanings as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding to L ¹ in the general formula (1).
However, the bond to L ² is any ^one of carbon atoms from X ¹¹ to X ¹⁸ , carbon atoms from R ²⁰³ to R ²⁰⁵ , nitrogen atoms in Y ¹ , and carbon atoms in Y ¹ . is there. ] L ¹ bonded to Z ¹ in the general formula (1) is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted naphthylene group, and a substituted or unsubstituted group. 2. The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is selected from the group consisting of fluorenylene groups. The organic electroluminescence device according to claim 2, wherein L ¹ bonded to Z ¹ in the general formula (1) is a single bond or a substituted or unsubstituted phenylene group. L ¹ bonded to Z ¹ in the general formula (1) is selected from a single bond or a linking group, and when L ¹ is a linking group, L ¹ is represented by the following formulas (111) to (117) The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is selected from the group consisting of groups represented by:

L ¹ in the general formula (1) is selected from either a single bond or a linking group, and when L ¹ is a linking group, L ¹ is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. 2. The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is a (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from a group hydrocarbon ring structure. L ¹ in the general formula (1) is an (a + 1) -valent residue formed by removing (a + 1) hydrogen atoms from an unsubstituted aromatic hydrocarbon ring structure having 6 to 12 ring carbon atoms. The organic electroluminescent element according to claim 5. Claim 1 wherein at least one of ^{R 102, R 103, R 106} , R 107, R 109 and ^{R 110} in formula (1), characterized in that it is a single bond for use in binding to ^{L 1} The organic electroluminescent element of description. 2. The organic electroluminescence device according to claim 1, wherein at least one of R ¹⁰⁹ and R ¹¹⁰ in the general formula (1) is a single bond used for bonding with L ¹ . In the general formula (1), R ¹¹⁰ is selected from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms. 2. The organic electroluminescence device according to claim 1, wherein the organic electroluminescence device is a group. 10. The organic electroluminescent device according to claim 9, wherein R ¹¹⁰ in the general formula (1) is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms. The organic electroluminescent device according to claim 1, wherein R ¹¹⁰ in the general formula (1), characterized by being represented by the following general formula (11).

[In the general formula (11),
Ar ¹ represents a group selected from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Each Ra has the same meaning as R ¹⁰¹ to R ¹¹⁰ that are not used for bonding with L ¹ in the general formula (1).
e represents an integer of 1 to 4.
When e is 2 to 4, a plurality of Ra are the same or different. ] The R ^{110 in the} general formula (1) is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 30 ring carbon atoms. The organic electroluminescent element of description. The R ^{110 in the} general formula (1) is selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted fluorenyl group. The organic electroluminescent element of description. 2. The organic electroluminescence device according to claim 1, wherein R ¹¹⁰ in the general formula (1) is selected from the group consisting of groups represented by the following formulas (121) to (134).

2. The organic electroluminescence device according to claim 1, wherein any one of R ¹¹² to R ¹¹⁴ and R ¹¹⁵ to R ^{117 in} the general formula (2) is a single bond used for bonding to L ^1. . 16. The organic electroluminescence device according to claim 15, wherein R ¹¹² or R ¹¹⁷ in the general formula (2) is a single bond used for bonding to L ¹ . 2. The organic electroluminescence device according to claim 1, wherein in the general formula (1), Z ¹ is selected from the group consisting of groups represented by the following formulas (141) to (146).

At least one of ^{L 1} in the general formula (1) is a linking group, ^R 101 ^{~ R 110} which is not used in binding to ^{L 1} is, by forming a substituent and the ring ^{L 1} or ^{L 1} dolphins, or, R ^{111 ~} R ¹²⁰ which is not used in binding to L ¹ an organic electroluminescence device according to claim 1, characterized in that it forms a substituent and the ring of L ¹ or L ¹ . In the general formula (21), of the X ¹ to X ^3, the organic electroluminescent device according to claim 1, wherein at least two are nitrogen atoms. In Formula (21) The organic electroluminescent device according to claim 19, wherein X ¹ and X ² is a nitrogen atom. ^2. The L2 in the general formula (22) is a divalent or trivalent residue of a substituted or unsubstituted aromatic hydrocarbon ring structure having 6 to 12 ring carbon atoms. The organic electroluminescent element of description. The organic electroluminescence device according to claim 19, wherein L ² in the general formula (22) is a divalent or trivalent residue of benzene, biphenyl or naphthalene. Formula (22) d is 1 or 2 in the organic electroluminescent device according to claim 1, wherein each of Y ¹ in the general formula (23) is a nitrogen atom. Wherein when d is 1 in the general formula (22) wherein the general formula ^{Y 1} in (23), d each ^{Y 1} is in the formula (23) in the case of 2, with respect to ^{L 2} The organic electroluminescence device according to claim 23, wherein the organic electroluminescence device is a nitrogen atom bonded by a single bond. 2. The organic electroluminescent device according to claim 1, wherein d in the general formula (22) is 1 or 2, and each Y ¹ in the general formula (23) is an oxygen atom. When d in the general formula (22) is 1, any one of X ¹¹ , X ¹⁴ , X ¹⁵ or X ^{18 in} the general formula (23) and when d is 2, ^X 11 ^23), one of X ^{14, X} 11 of one and the other of the general formula ^{X 15} or ^{X 18 (23), X 14} , X 15 or ^{X 18} is a single bond to ^{L 2} 26. The organic electroluminescence device according to claim 25, wherein the organic electroluminescence device is a carbon atom bonded together by the method. 2. The organic electroluminescence device according to claim 1, wherein the HAr of the general formula (22) is selected from the group consisting of groups represented by the following formulas (221a) to (221d).

2. The organic electroluminescence device according to claim 1, wherein Ar ²⁰² in the general formula (21) is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms. Ar ²⁰² in the said General formula (21) is a substituted or unsubstituted phenyl group, The organic electroluminescent element of Claim 1 characterized by the above-mentioned. Ar ²⁰³ in the general formula (21) is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring carbon atoms. The organic electroluminescent element according to claim 1, wherein The organic electroluminescence device according to claim 30, wherein Ar ²⁰³ in the general formula (21) is a phenyl group, a biphenyl group, or a naphthyl group. The organic electroluminescence device according to claim 30, wherein Ar ²⁰³ in the general formula (21) is selected from the following group consisting of groups represented by the following formulas (211a) to (211n).

The organic electroluminescent device according to claim 32, wherein Ar ²⁰³ in the general formula (21) is selected from the group consisting of groups represented by the following formulas (212a) to (212h).

2. The organic electroluminescent device according to claim 1, wherein Ar ²⁰³ in the general formula (21) is a substituted or unsubstituted nitrogen-containing heterocyclic group having 5 to 20 ring atoms. 2. The organic electroluminescence device according to claim 1, wherein the general formula (22) is selected from the group consisting of groups represented by the following formulas (222a) to (222f).

2. The organic electroluminescence device according to claim 1, wherein the general formula (22) is selected from the group consisting of groups represented by the following formulas (223a) to (223g).

The organic light-emitting device according to claim 1, further comprising any one of compounds represented by the following general formulas (31), (41), and (51) in the light emitting layer.

[In the general formula (31), R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ³¹¹ are each independently a hydrogen atom, hydroxyl group, cyano group, nitro group, carboxyl group, substituted or Substituted silyl group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted Substituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxycarbonyl group having 2 to 50 carbon atoms, substituted or unsubstituted An arylamino group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and substitution Alternatively, it is selected from the first group consisting of unsubstituted heterocyclic groups having 5 to 30 ring atoms.
In the general formula (31), R ³⁰³ is selected from the second group constituted by removing hydrogen atoms from the first group shown for R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ^311. It is.
In the general formula (31), R ³⁰⁴ is constituted by removing an aromatic hydrocarbon group and a heterocyclic group from the first group shown for R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ^311. Selected from the third group.
In the general formula (31), R ³⁰⁷ and R ³¹² are each independently a hydrogen atom or a hydroxyl group from the first group shown for R ³⁰¹ , R ³⁰² , R ³⁰⁵ , R ³⁰⁶ and R ³⁰⁸ to R ^311. , A cyano group, a nitro group, a carboxyl group, and a silyl group.
In the general formula (31), R ³⁰¹ and R ³⁰² , R ³⁰² and R ³⁰³ , R ³⁰⁵ and R ³⁰⁶ , R ³⁰⁶ and R ³⁰⁷ , R ³⁰⁷ and R ³⁰⁸ , R ³⁰⁸ and R ³⁰⁹ , R ³⁰⁹ and R ³¹⁰ , R ³¹⁰ and R ³¹¹ , and R ³¹¹ and R ³¹² may combine with each other to form a saturated or unsaturated ring, or may not form a saturated or unsaturated ring, Substituted or unsubstituted. ]

[In the general formula (41),
R ⁴⁰⁰ to R ⁴⁰⁹ are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring forming carbon number. 6 to 30 aromatic hydrocarbon groups are shown.
Ar ⁴⁰¹ to Ar ⁴⁰⁴ each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. When Ar ⁴⁰¹ to Ar ⁴⁰⁴ have an alkyl group as a substituent, each of them has at least two alkyl groups. ]

[In the general formula (51),
R ⁵⁰¹ to R ⁵⁰⁸ are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted silyl group, or a substituted or unsubstituted ring forming carbon number. Represents an aromatic hydrocarbon group having 6 to 30; Ar ⁵⁰¹ to Ar ⁵⁰⁴ each represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number; 5 to 30 heterocyclic groups are shown.
However, at least one of Ar ⁵⁰¹ to Ar ⁵⁰⁴ is a heterocyclic group represented by the following formula (52). ]

[In general formula (52),
R ⁵¹¹ to R ⁵¹⁷ are each a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, substituted or unsubstituted An alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 30 ring atoms. The heterocyclic group of is shown.
R ⁵¹¹ and R ⁵¹² , R ⁵¹² and R ⁵¹³ , R ⁵¹³ and R ⁵¹⁴ , R ⁵¹⁵ and R ⁵¹⁶ , and R ⁵¹⁶ and R ⁵¹⁷ may be bonded to each other to form a saturated or unsaturated ring. These rings may be substituted.
X ⁵¹ is selected from either an oxygen atom or a sulfur atom.
y ⁵¹ is a single bond bonded to the nitrogen atom of the general formula (51). ] An electronic device equipped with the organic electroluminescence element according to claim 1.

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