JP2015065325A - Organic electroluminescent element, and electronic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide: an organic EL element which enables the increase in light emission efficiency, and the achievement of a longer life and a lower drive voltage; and an electronic device having such an organic EL element.SOLUTION: An organic electroluminescent element comprises a light-emitting layer which includes a first compound expressed by the general formula (1) below and a second compound expressed by the general formula (2) below. In the general formula (1), Rand Rare each a predetermined aromatic hydrocarbon group or a heterocyclic group. In the general formula (2), A is represented by the general formula (2a) below.

Description

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

  Organic electroluminescence elements using organic substances (hereinafter sometimes abbreviated as organic EL elements) are expected to be used as solid-state, inexpensive, large-area, full-color display elements, 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 than inorganic light-emitting diodes, and their characteristic deterioration has not been practically achieved. Although recent organic EL devices have been gradually improved, higher light emission efficiency is required.

  For example, Patent Document 1 and Patent Document 2 describe an organic electroluminescent device including a light-emitting layer containing a benzofluorene compound substituted with a diarylamino group as a dopant material and an anthracene derivative as a host material. Yes. According to Patent Document 1, an attempt is made to obtain sufficient performance in terms of current efficiency and device life by using such an organic electroluminescent device. According to Patent Document 2, such an organic electroluminescence element attempts to emit blue light with high color purity while maintaining a conventional driving voltage.

JP 2008-291006 A JP2011-225546A

  However, in order to employ the organic EL element in an electronic device such as a lighting device or a display device, it is required to further improve the light emission efficiency, extend the lifetime, and lower the driving voltage.

  An object of the present invention is to provide an organic electroluminescence element capable of improving luminous efficiency, extending the lifetime, and reducing a driving voltage, and to provide an electronic device including the organic electroluminescence element. It is.

The organic electroluminescence device according to one embodiment of the present invention is
A cathode,
The anode,
Having one or more organic layers disposed between the cathode and the anode;
The organic layer includes a light emitting layer,
The light emitting layer includes a first compound represented by the following general formula (1) and a second compound represented by the following general formula (2).

(In the general formula (1),
R _{101 to} R ₁₀₈ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by -Si (R ₁₁₁ ) ₃ ;
R ₁₁₁ is independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
R ₁₀₉ and R ₁₁₀ are each independently
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 R ₁₀₉ and R ₁₁₀ are substituted or unsubstituted condensed aromatic hydrocarbon groups, they are condensed aromatic hydrocarbon groups in which two or three six-membered rings are condensed.
In some cases, adjacent groups out of R _{101 to} R ₁₀₈ may be bonded to each other to form a ring.

However, when R ₁₀₉ is an unsubstituted phenyl group and R ₁₁₀ is a group represented by the following general formula (10), R ₁₁₃ in the following general formula (10) is substituted or unsubstituted. Or an aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. )

(When R ₁₀₉ is an unsubstituted phenyl group and R ₁₁₀ is a group represented by the following general formula (11), R ₁₁₄ in the following general formula (11) is an unsubstituted group. It is an aromatic hydrocarbon group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.)

(When R ₁₀₉ is an unsubstituted phenyl group and R ₁₁₀ is a group represented by the following general formula (12), R ₁₁₅ in the following general formula (12) is an unsubstituted group. It is an aromatic hydrocarbon group having 12 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.)

(In addition, when R ₁₀₉ is an unsubstituted 1-naphthyl group, R ₁₁₀ is
A group represented by the following general formula (13):
A group represented by the following general formula (14):
It is a substituted or unsubstituted aromatic hydrocarbon group having 12 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. )

(In the general formula (13), m is 5, and R ₁₁₆ is independently synonymous with R _{101 to} R _108. However, at least one of the five R ₁₁₆ is substituted or unsubstituted. An aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and R ₁₁₆ is a benzene ring represented by the general formula (13). Bond to a carbon atom.
In the general formula (14), n is 7, and R ₁₁₇ is independently the same as R _{101 to} R ₁₀₈ . However, at least one of the seven R ₁₁₇ is 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. . R ₁₁₇ is bonded to the carbon atom of the naphthalene ring of the general formula (14). )

[In the general formula (2),
Ar ²¹ and Ar ²² are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. However, Ar ²¹ and Ar ²² may be bonded to each other to form a ring or not form a ring.
L ^{20 to} L ²² are each independently a single bond or a linking group,
As the linking group in L ^{20 to} L ²² ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
n ₂ is an integer of 1 to 4, and when n ₂ is 2 or more, the plurality of Ar ²¹ , Ar ²² , and L ^{20 to} L ²² may be the same as or different from each other.
A is represented by the following general formula (2a). ]

[In the general formula (2a),
R ^{231 to} R ²³⁸ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms or a silyl group represented by —Si (R ²⁴¹ ) ₃ .
One set of R ²³¹ and R ²³² , R ²³² and R ²³³ , R ²³³ and R ²³⁴ , R ²³⁵ and R ²³⁶ , R ²³⁶ and R ²³⁷ , and R ²³⁷ and R ²³⁸ is represented by the following general formula (2b). A carbon atom that binds to the structure represented.
R ²³⁹ and R ²⁴⁰ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by —Si (R ²⁴² ) ₃ .
R ²⁴¹ and R ²⁴² are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. ]

[In the general formula (2b),
* Is any of R ²³¹ and R ²³² , R ²³² and R ²³³ , R ²³³ and R ²³⁴ , R ²³⁵ and R ²³⁶ , R ²³⁶ and R ²³⁷ , and R ²³⁷ and R ^{238 in} the general formula (2a), respectively. Represents the bond position to a set of carbon atoms.
R ^{251 to} R ²⁵⁴ are independently the same as R ^{231 to} R ²³⁸ in the general formula (2).
In addition, n ₂ out of R ^{231 to} R ^{238 in the} general formula (2a) and R ^{251 to} R ^{254 in} the general formula (2b) are bonds that are bonded to L ²⁰ in the general formula (2). . ]

  An electronic device according to one embodiment of the present invention includes the organic electroluminescence element according to one embodiment of the present invention.

  ADVANTAGE OF THE INVENTION According to this invention, the organic EL element which can improve luminous efficiency, prolong a lifetime, and can reduce a drive voltage can be provided. Moreover, according to this invention, the electronic device provided with the said organic EL element can be provided.

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

  Hereinafter, embodiments of the organic EL element which is one embodiment of the present invention will be described.

[First embodiment]
(Element structure of organic EL element)
The configuration of the organic EL element according to the first embodiment of the present invention will be described.
The organic EL element includes an organic layer between both an anode and a cathode. This organic layer has one or more layers composed of an organic compound. The organic layer may further contain an inorganic compound.
In the organic EL device of the present embodiment, at least one of the organic layers has a light emitting layer. Therefore, the organic layer may be composed of, for example, a single light emitting layer, or an organic layer such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, or an electron barrier layer. You may have the layer employ | adopted with an EL element.

As a typical element configuration of the organic EL element,
(A) Anode / light emitting layer / cathode (b) Anode / hole injection / transport layer / light emitting layer / cathode (c) Anode / light emitting layer / electron injection / transport layer / cathode (d) Anode / hole injection / transport Examples of the structure include layer / light emitting layer / electron injection / transport layer / cathode (e) anode / hole injection / transport layer / light emitting layer / barrier layer / electron injection / transport layer / cathode.
Among the above, the configuration (d) is preferably used, but it is of course 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 “an electron injection layer and an electron transport layer”. "At least one of them". 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.
As for the organic layer in the electron transport region existing between the light emitting layer and the cathode, all of the layers exhibit electron transport properties, but in general, the barrier layer serves to prevent the diffusion of excitation energy, and the electron injection layer. Serves to reduce the electron injection barrier.

In FIG. 1, schematic structure of an example of the organic EL element in this embodiment 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 includes a light emitting layer 5, a hole injection / transport layer 6 provided between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 provided between the light emitting layer 5 and the cathode 4. It consists of
The hole injection / transport layer 6 means at least one of a hole injection layer and a hole transport layer. The electron injection / transport layer 7 means at least one of an electron injection layer and an 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 3 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 4 side. Further, each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of a single layer, or a plurality of layers may be laminated.

(Light emitting layer)
In the organic EL device of the present embodiment, the light emitting layer 5 includes a first compound represented by the following general formula (1) and a second compound represented by the following general formula (2).

-1st compound First, the 1st compound represented by following General formula (1) is demonstrated. In the present embodiment, it is preferable to use the first compound represented by the following general formula (1) as the host material.

In the general formula (1), R _{101 to} R ₁₀₈ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by -Si (R ₁₁₁ ) ₃ ;
R ₁₁₁ is independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
R ₁₀₉ and R ₁₁₀ are each independently
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 R ₁₀₉ and R ₁₁₀ are substituted or unsubstituted condensed aromatic hydrocarbon groups, they are condensed aromatic hydrocarbon groups in which two or three six-membered rings are condensed.
In some cases, adjacent groups out of R _{101 to} R ₁₀₈ may be bonded to each other to form a ring.

Note that R ₁₀₉ and R ₁₁₀ in the first compound represented by the general formula (1) are each independently a phenyl group, a biphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, or a terphenyl group. These groups may have a substituent. In this case, the substituent is preferably an aromatic hydrocarbon group having 6 to 14 ring carbon atoms.

In this embodiment, in the general formula (1), when the R ₁₀₉ is an unsubstituted phenyl group and the R ₁₁₀ is a group represented by the following general formula (10), the following general formula ( R ₁₁₃ in 10) is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

In the general formula (1), when the R ₁₀₉ is an unsubstituted phenyl group and the R ₁₁₀ is a group represented by the following general formula (11), the following general formula (11) R ₁₁₄ is an unsubstituted aromatic hydrocarbon group having 6 to 14 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

In the general formula (1), when the R ₁₀₉ is an unsubstituted phenyl group and the R ₁₁₀ is a group represented by the following general formula (12), the following general formula (12) R ₁₁₅ is an unsubstituted aromatic hydrocarbon group having 12 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

In the general formula (1), when R ₁₀₉ is an unsubstituted 1-naphthyl group, R ₁₁₀ is
A group represented by the following general formula (13):
A group represented by the following general formula (14):
It is a substituted or unsubstituted aromatic hydrocarbon group having 12 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

M in the general formula (13) is 5, and R ₁₁₆ is independently synonymous with R _{101 to} R ₁₀₈ . However, at least one of the five R ₁₁₆ is 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. . Each R ₁₁₆ is bonded to a carbon atom of the benzene ring of the general formula (13).
In the general formula (14), n is 7, and R ₁₁₇ is independently the same as R _{101 to} R ₁₀₈ . However, at least one of the seven R ₁₁₇ is 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. . R ₁₁₇ is bonded to the carbon atom of the naphthalene ring of the general formula (14).

  In the present embodiment, the first compound represented by the general formula (1) is preferably represented by the following general formula (15).

In the general formula (15), R _{101 to} R ₁₀₈ , R _{121 to} R ₁₂₇ , and R _{131 to} R ₁₃₇ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
However, at least one of R _{121 to} R ₁₂₇ and R _{131 to} R ₁₃₇ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 ~ 30 heterocyclic groups,
R ₁₂₁ and R ₁₂₂ , R ₁₂₂ and R ₁₂₃ , R ₁₂₃ and R ₁₂₄ , R ₁₂₄ and R ₁₂₅ , R ₁₂₅ and R ₁₂₆ , and at least one combination of R ₁₂₆ and R ₁₂₇ A ring structure fused to the naphthalene ring may be constructed.

In the general formula (15), at least one of R _{121 to} R ₁₂₇ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 A heterocyclic group having -30, and at least one of R _{131 to} R ₁₃₇ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number It is preferably a 5-30 heterocyclic group.

  In the present embodiment, the first compound represented by the general formula (1) is preferably represented by the following general formula (16).

In the general formula (16), R _{101 to} R ₁₀₈ , R _{141 to} R ₁₄₅ , and R _{151 to} R ₁₅₅ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
However, at least one of R _{141 to} R ₁₄₅ and R _{151 to} R ₁₅₅ is
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,
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,
A ring structure in which at least one of R ₁₄₁ and R ₁₄₂ , R ₁₄₂ and R ₁₄₃ , R ₁₄₃ and R ₁₄₄ , and R ₁₄₄ and R ₁₄₅ is bonded to each other and condensed to a benzene ring is constructed. Also good.

In the general formula (16), at least one of R _{141 to} R ₁₄₅ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon group having 1 to 10 carbon atoms. An alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and at least one of R _{151 to} R ₁₅₅ Are substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 10 ring carbon atoms. It is preferably a group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.

  In the present embodiment, the first compound represented by the general formula (1) is preferably represented by the following general formula (17).

In the general formula (17), R _{101 to} R ₁₀₈ are independently the same as R _{101 to} R ₁₀₈ in the general formula (1),
R _{161 to} R ₁₆₅ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by -Si (R ₁₁₁ ) ₃ ;
R ₁₁₁ is independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
However, at least one of R _{161 to} R ₁₆₅ is 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. It is.

  In the present embodiment, the first compound represented by the general formula (1) is preferably represented by the following general formula (18).

In the general formula (18), R _{101 to} R ₁₀₈ , R _{171 to} R ₁₇₇ , R _{181 to} R ₁₈₅ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
However, when one of R _{171 to} R ₁₇₇ is a substituted or unsubstituted aromatic hydrocarbon group, the number of ring-forming carbons of the aromatic hydrocarbon group is 10 or more and 30 or less.

  The first compound represented by the general formula (18) is preferably represented by the following general formula (181).

In the general formula (181), R _{101 to} R ₁₀₈ , R _{175 to} R ₁₇₇ , and R _{181 to} R ₁₈₅ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
However, at least one of R _{175 to} R ₁₇₇ is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. It is.

  The first compound represented by the general formula (181) is preferably represented by any one of the following general formulas (182) to (186).

In the general formulas (182) to (186), R _{101 to} R ₁₀₈ and R _{191 to} R ₁₉₇ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
R < ₁₇₅ > -R <_177> is respectively independently synonymous with R _{< 175} > -R < ₁₇₇ > in the said General formula (181).

  In the present embodiment, the first compound represented by the general formula (18) is preferably represented by the following general formula (187).

In the general formula (187), R _{101 to} R ₁₀₈ , R _{171 to} R ₁₇₄ , and R _{181 to} R ₁₈₅ are independently the same as R _{101 to} R ₁₀₈ in the general formula (1),
However, at least one of R _{171 to} R ₁₇₄ is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. It is.

In this embodiment, R ₁₀₉ and R ₁₁₀ in the first compound represented by the general formula (1) are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Preferably there is. That is, the 9th and 10th carbon atoms of the anthracene ring represented by the general formula (1) and an aromatic hydrocarbon ring of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms are formed. It is preferable that the constituent carbon atoms are bonded by a single bond. Furthermore, the aromatic hydrocarbon group having 6 to 30 ring carbon atoms is preferably a phenyl group or an aromatic condensed hydrocarbon group constructed by condensing only a 6-membered ring.

In the present embodiment, R _{101 to} R ₁₀₈ in the first compounds represented by the general formulas (1), (15) to (18), (181) to (187) are preferably hydrogen atoms. .

In the present embodiment, R ₁₀₁ , R ₁₀₄ , R ₁₀₅ , and R ₁₀₈ in the first compounds represented by the general formulas (1), (15) to (18), (181) to (187) are: , A hydrogen atom, and at least one of R ₁₀₂ , R ₁₀₃ , R ₁₀₆ , and R ₁₀₇ is a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted carbon number of 3 to 10 cycloalkyl groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring carbon atoms, substituted or unsubstituted 6 to 30 ring carbon atoms An aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by —Si (R ₁₁₁ ) ₃ is preferable.

In the present embodiment, R ₁₀₁ , R ₁₀₄ , R ₁₀₅ , and R ₁₀₈ in the first compounds represented by the general formulas (1), (15) to (18), (181) to (187) are: , A hydrogen atom, and at least one of R ₁₀₂ , R ₁₀₃ , R ₁₀₆ , and R ₁₀₇ is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted ring carbon number of 6 to 6 30 aromatic hydrocarbon group, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by —Si (R ₁₁₁ ) ₃ , and the others being hydrogen atoms. preferable.

In this specification, the number of ring-forming carbon atoms refers to a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among atoms constituting the ring itself. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The “ring-forming carbon number” described below is the same unless otherwise specified.
The number of ring-forming atoms refers to the ring itself of a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of atoms to be played. An atom that does not constitute a ring (for example, a hydrogen atom that terminates the dangling bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is included in the number of ring-forming atoms Absent. The “number of ring-forming atoms” described below is the same unless otherwise specified.
Next, each substituent described in the general formula will be described.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, Fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrycenyl group, benzo [b] triphenylenyl group, picenyl group, perylenyl group Etc.
As an aromatic hydrocarbon group in this embodiment, it is preferable that ring forming carbon number is 6-20, More preferably, it is still more preferable that it is 6-12. Of the aromatic hydrocarbon groups, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable. For the 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group, the 9-position carbon atom is substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the present embodiment described later. It is preferable that

Examples of the heterocyclic group having 5 to 30 ring atoms in the present embodiment include a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl Group, benzothiazolyl group, benzisoxazolyl group, benzoisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, piperidinyl group, pyrrolidinyl group, piperazinyl group, morpholyl Group, phenazinyl group, phenothiazinyl group, phenoxazinyl group and the like.
The number of ring-forming atoms of the heterocyclic group in this embodiment is preferably 5-20, and more preferably 5-14. Among the above heterocyclic groups, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group are particularly preferable. As for the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the substituted or unsubstituted aromatic hydrocarbon having 6 to 30 ring carbon atoms in the present embodiment is attached to the 9th-position nitrogen atom. The group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.

In the present embodiment, the alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic. Examples of the linear or branched alkyl group include a methyl group, ethyl group, n-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, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1- A heptyloctyl group and a 3-methylpentyl group.
The linear or branched alkyl group in the present embodiment preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Among the linear or branched alkyl groups, 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 , An amyl group, an isoamyl group, and a neopentyl group are particularly preferable.
Examples of the cycloalkyl group in this embodiment include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. The ring-forming carbon number of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8. Among the cycloalkyl groups, a cyclopentyl group and a cyclohexyl group are particularly preferable.
Examples of the halogenated alkyl group in which the alkyl group is substituted with a halogen atom include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.

  Examples of the alkylsilyl group having 3 to 30 carbon atoms in the present embodiment include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group. , Tri-n-butylsilyl group, tri-n-octylsilyl group, triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t- Examples thereof include a butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. The three alkyl groups in the trialkylsilyl group may be the same or different.

Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
The dialkylarylsilyl group has, for example, two alkyl groups exemplified as the alkyl group having 1 to 30 carbon atoms, and one dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Is mentioned. The carbon number of the dialkylarylsilyl group is preferably 8-30.
Examples of the alkyldiarylsilyl group include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. . The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
Examples of the triarylsilyl group include a triarylsilyl group having three aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30.

Alkoxy group having 1 to 30 carbon atoms in the present embodiment is represented as -OZ _1. Examples of _{Z 1,} include alkyl groups of 1 to 30 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.
Examples of the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include those in which the C 1-30 alkoxy group is substituted with one or more halogen groups.

Aryloxy group ring forming C6-30 in this embodiment is expressed as -OZ _2. Examples of this Z ₂ include the aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. Examples of the aryloxy group include a phenoxy group.

Alkylamino group having 2 to 30 carbon atoms is represented as -NHR _V or -N _{(R V) 2,.} Examples of _{R V,} include alkyl groups of 1 to 30 carbon atoms.

The arylamino group having 6 to 60 ring carbon atoms is represented as —NHR _W or —N (R _W ) ₂ . Examples of R _W, and an aromatic hydrocarbon group of the ring-forming C6-30.

Alkylthio group having 1 to 30 carbon atoms is represented as -SR _V. Examples of _{R V,} include alkyl groups of 1 to 30 carbon atoms.
Ring formation arylthio group having 6 to 30 carbon atoms is expressed as -SR _W. Examples of R _W, and an aromatic hydrocarbon group of the ring-forming C6-30.

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 this embodiment, the substituent in the case of “substituted or unsubstituted” includes the aromatic hydrocarbon group, heterocyclic group, alkyl group (straight chain or branched chain alkyl group, cycloalkyl group) as described above. Group, haloalkyl group), alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylamino group, arylamino group, alkylthio group, arylthio group, alkenyl group, alkynyl group, aralkyl group, halogen atom, A cyano group, a hydroxyl group, a nitro group, and a carboxy group are mentioned.
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 alkenyl group is preferably an alkenyl group having 2 to 30 carbon atoms, which may be linear, branched or cyclic, for example, vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group. , Docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, 2-phenyl-2-propenyl group, cyclopentadienyl group, cyclopentenyl group, cyclohexenyl group And cyclohexadienyl group.

  The alkynyl group is preferably an alkynyl group having 2 to 30 carbon atoms, and may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.

As the aralkyl group, an aralkyl group having 6 to 30 ring carbon atoms is preferable and represented by -Z ₃ -Z ₄ . Examples of Z ₃ include alkylene groups corresponding to the alkyl groups having 1 to 30 carbon atoms. Examples of this Z ₄ include the above aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. This aralkyl group is an aralkyl group having 7 to 30 carbon atoms (the aryl moiety is 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), and the alkyl moiety is 1 to 30 carbon atoms (preferably 1 to 1 carbon atoms). 20, more preferably 1-10, still more preferably 1-6). 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- Examples include naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

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

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, “carbon number ab” in the expression “XX group having a substituted or unsubstituted carbon number ab” represents the number of carbon atoms 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.

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

-2nd compound Next, the 2nd compound represented by following General formula (2) is demonstrated. In this embodiment, it is preferable to use the 2nd compound represented by following General formula (2) as a dopant material.

{[In the general formula (2),
Ar ²¹ and Ar ²² are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. However, Ar ²¹ and Ar ²² may be bonded to each other to form a ring or not form a ring.
L ^{20 to} L ²² are each independently a single bond or a linking group,
As the linking group in L ^{20 to} L ²² ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
n ₂ is an integer of 1 to 4, and when n ₂ is 2 or more, the plurality of Ar ²¹ , Ar ²² , and L ^{20 to} L ²² may be the same as or different from each other.
A is represented by the following general formula (2a). ]

[In the general formula (2a),
R ^{231 to} R ²³⁸ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms or a silyl group represented by —Si (R ²⁴¹ ) ₃ .
One set of R ²³¹ and R ²³² , R ²³² and R ²³³ , R ²³³ and R ²³⁴ , R ²³⁵ and R ²³⁶ , R ²³⁶ and R ²³⁷ , and R ²³⁷ and R ²³⁸ is represented by the following general formula (2b). A carbon atom that binds to the structure represented.
R ²³⁹ and R ²⁴⁰ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by —Si (R ²⁴² ) ₃ .
R ²⁴¹ and R ²⁴² each independently represent a hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. ]

[In the general formula (2b),
* Is any of R ²³¹ and R ²³² , R ²³² and R ²³³ , R ²³³ and R ²³⁴ , R ²³⁵ and R ²³⁶ , R ²³⁶ and R ²³⁷ , and R ²³⁷ and R ^{238 in} the general formula (2a), respectively. Represents the bond position to a set of carbon atoms.
R ^{251 to} R ²⁵⁴ are independently the same as R ^{231 to} R ²³⁸ in the general formula (2). ]
In addition, n ₂ out of R ^{231 to} R ^{238 in the} general formula (2a) and R ^{251 to} R ^{254 in} the general formula (2b) are bonds that are bonded to L ²⁰ in the general formula (2). . }

  The general formula (2a) is preferably represented by any one of the following general formulas (2a-1) to (2a-3). Especially, it is more preferable that the general formula (2a) is represented by the following general formula (2a-3).

[In the general formula (2a-1) ~ (2a -3), R 231 ~R 238, R 239, R 240 is a ^{R 231 ~R 238, R 239,} R 240 at each general formula (2a) It is synonymous.
R ²⁵¹ to R ²⁵⁴ are each independently the same meaning as ^R 251 ^{to R 254} in the general formula (2b). ]

In the general formula (2a-3), R ²³³ and R ²³⁶ are preferably a bond that bonds to L ²⁰ of the general formula (2).

  In the present embodiment, the general formula (2) is preferably represented by the following general formula (21).

[In the general formula ^{(21), A, Ar 22} , L 20 ~L 22, and _{n 2,} ^A in each of the general formula ^{(2), Ar 22, L} 20 ~L 22, and _{n 2} and interchangeably is there.
R ^{211 to} R ²¹⁵ are each independently
Hydrogen atom,
A cyano group,
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a silyl group represented by —Si (R ²¹⁶ ) ₃ .
R ²¹⁶ is independently the same as R ²⁴¹ and R ²⁴² in the general formula (2a). ]

  In the present embodiment, the general formula (2) is more preferably represented by the following general formula (22).

[In the general formula ^{(22), A, L 20} ~L 22, and _{n 2} is an ^A in each of the general formula ^{(2), L 20 ~L 22} , and the _{n 2} synonymous.
R ^{211 to} R ²¹⁵ and R ^{221 to} R ²²⁵ are each independently
Hydrogen atom,
A cyano group,
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a silyl group represented by —Si (R ²¹⁶ ) ₃ .
R ²¹⁶ is independently the same as R ²⁴¹ and R ²⁴² in the general formula (2a). ]

  In the present embodiment, the general formula (2) is preferably represented by the following general formula (23).

[In the general formula ^{(23), A, Ar 22} , L 20 ~L 22, and _{n 2,} ^A in each of the general formula ^{(2), Ar 22, L} 20 ~L 22, and _{n 2} and interchangeably is there.
R ^{211 to} R ²¹⁵ and R ^{261 to} R ²⁶⁸ have the same meanings as R ^{211 to} R ²¹⁵ in the general formula (21), respectively. ]

In the general formulas (2) and (21) to (23), it is preferable that all of L ^{20 to} L ²² are single bonds.
In the general formulas (2) and (21) to (23), n ₂ is preferably 1 or 2, and n ₂ is more preferably 2.
In the general formulas (21) to (23), A is preferably represented by the general formula (2a-3), and R ²³³ and R ²³⁶ are preferably bonds that bind to L ²⁰ . In this case, L ²⁰ is more preferably a single bond.

  In the present embodiment, the second compound represented by the general formula (2) is preferably represented by the following general formula (27).

Formula ^{(27) Ar 21, Ar 22} , L 20 ~L 22 in, respectively, have the same meaning as ^{Ar 21, Ar 22, L 20} ~L 22 in the general formula (2), the two ^{Ar 21} is The two Ar ²² may be the same or different from each other, and two L ²⁰ , two L ²¹ , and two L ²² may be the same or different from each other. .
In the general formula (27), R ²³¹ , R ²³² , R ²³⁴ , R ²³⁵ , R ²³⁷ , and R ²³⁸ are each independently synonymous with R ^{231 to} R ²³⁸ in the general formula (2a).
In the general formula (27), R ²³⁹ and R ²⁴⁰ are each independently synonymous with R ²³⁹ and R ²⁴⁰ in the general formula (2a).
In the general formula (27), L ²⁰ is preferably a single bond.
In the general formula (27), each of L ²⁰ , L ²¹ and L ²² is preferably a single bond.

  The general formula (2) is more preferably represented by any of the following general formulas (24) to (26).

[In the general formula (24) ~ (26), ^{Ar 22} has the same meaning as ^{Ar 22} in the general formula (2). When there are a plurality of Ar ^{22 s} , they may be the same or different.
R ^{239, R 240} are each the same meaning as ^{R 239, R 240} in the formula (2b).
R ^{211 to} R ²¹⁵ , R ^{221 to} R ²²⁵ , and R ^{261 to} R ²⁶⁸ are each independently synonymous with R ^{211 to} R ²¹⁵ in the general formula (21). ]

In the general formulas (21) to (26), R ^{211 to} R ²²⁵ and R ^{261 to} R ²⁶⁸ are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted C 1-30. An alkyl group or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms is preferable. R ^{211 to} R ²²⁵ and R ^{261 to} R ²⁶⁸ are more preferably each independently a hydrogen atom, a fluorine atom, a cyano group, a methyl group, a tertiary butyl group, a phenyl group, or a trimethylsilyl group.
In the general formulas (2a), (2a-1) to (2a-3) and (24) to (26), R ²³⁹ and R ²⁴⁰ are preferably a methyl group or a phenyl group.
Furthermore, in the general formulas (21), (23), (24), and (26), Ar ²² is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthylene group.
In the general formula (26), R ^{261 to} R ²⁶⁸ are preferably all hydrogen atoms, or R ²⁶³ and R ²⁶⁶ are preferably a methyl group or a phenyl group.

  In this embodiment, each substituent described in the general formulas (2), (2a), (2b), (2a-1) to (2a-3), and (21) to (26) It is the same.

  In the present embodiment, a multiple linking group formed by bonding 2 to 4 groups selected from aromatic hydrocarbon groups, and a multiple linking group formed by bonding 2 to 4 groups selected from heterocyclic groups. Or an example of a multiple linking group formed by bonding two to four groups selected from an aromatic hydrocarbon group and the heterocyclic group is selected from the aromatic hydrocarbon group and the heterocyclic group; And divalent groups formed by bonding from 1 to 4 groups. Examples of the multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group include heterocyclic group-aromatic hydrocarbon group, aromatic hydrocarbon group-heterocycle Group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group-heterocycle Group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, and the like. Preferably, a divalent group formed by bonding the aromatic hydrocarbon group and the heterocyclic group one by one, that is, a heterocyclic group-aromatic hydrocarbon group, and an aromatic hydrocarbon group-heterocyclic group. . Specific examples of the aromatic hydrocarbon group and the heterocyclic group in these multiple linking groups include the groups described for the aromatic hydrocarbon group and the heterocyclic group.

Specific examples of the compound represented by the general formula (2) are shown below, but the present invention is not limited to these exemplified compounds.
In the following exemplary compounds, TMS represents a trimethylsilyl group, t-Bu represents a tertiary butyl group, and Me represents a methyl group.

(substrate)
The substrate is used as a support for the organic EL element. For example, glass, quartz, plastic, or the like can be used as the substrate. Further, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. . Moreover, an inorganic vapor deposition film can also be used.

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO): indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide And graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a metal material nitride (for example, titanium nitride).
These materials are usually formed by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1% by mass to 10% by mass of zinc oxide is added to indium oxide. For example, indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide. By using a target, it can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method, etc.
Since the hole injection layer formed in contact with the anode among the EL layers formed on the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode, Materials that can be used as the electrode material (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, and other elements belonging to Group 1 or Group 2 of the periodic table of elements) can be used.
An element belonging to Group 1 or Group 2 of the periodic table, which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. Note that when an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

(cathode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
Note that in the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.
By providing an electron injection layer, a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

(Hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
As a substance having a high hole injection property, 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, which is a low molecular organic compound, is used. , 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N ′-(3-methylphenyl) -N′-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N -F Enylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- An aromatic amine compound such as [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) can also be used.
As the substance having a high hole injecting property, a high molecular compound (an oligomer, a dendrimer, a polymer, or the like) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.

(Hole transport layer)
The hole transport layer is a layer containing a substance having a high hole transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) or N, N′-bis (3-methylphenyl) -N, N′— Diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (Spiro-9,9'-Biff Oren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB) can be used aromatic amine compounds such as. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / Vs or higher.
For the hole transport layer, a carbazole derivative such as CBP, CzPA, or PCzPA, or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds Can be used. Specifically, as a low-molecular organic compound, Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), A metal complex such as BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Pert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4- Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4- Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: B) Heteroaromatic compounds such as zOs) can also be used. The substances mentioned here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that any substance other than the above substances may be used for the electron-transport layer as long as the substance has a higher electron-transport property than the hole-transport property. Further, the electron-transport layer is not limited to a single layer, and two or more layers including the above substances may be stacked.
Moreover, a high molecular compound can also be used for an electron carrying layer. For example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like can be used.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. For the electron injection layer, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. An alkali metal, an alkaline earth metal, or a compound thereof can be used. In addition, a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property, specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer described above is used. be able to. The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

(Layer formation method)
The method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, but a dry film forming method such as a vacuum evaporation method, a sputtering method, a plasma method, an ion plating method, a spin method, Known methods such as a coating method, a dipping method, a flow coating method, and a wet film forming method such as an ink jet method can be employed.

(Film thickness)
The film thickness of each organic layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, it is high. Since an applied voltage is required and the efficiency is deteriorated, the range of several nm to 1 μm is usually preferable.

[Electronics]
The organic EL element according to the present embodiment can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, a tablet, or a personal computer, and electronic devices such as lighting or a light emitting device for a vehicle lamp. .

[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 satisfies the conditions described in the above embodiment, and phosphorescence is performed even if the other light emitting layers are fluorescent light emitting layers. A 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.
As a case where a plurality of light emitting layers are laminated, for example, an organic EL element 1A shown in FIG. The organic EL element 1A includes an organic layer 10A. The organic layer 10A includes a first light-emitting layer 51 and a second light-emitting layer 52 between the hole injection / transport layer 6 and the electron injection / transport layer 7. The organic EL element 1 shown in FIG. 1 is different from the organic EL element 1 shown in FIG. At least one of the first light-emitting layer 51 and the second light-emitting layer 52 contains the first compound represented by the general formula (1) and the second compound represented by the general formula (2). Yes. In other respects, the organic EL element 1 </ b> A is configured similarly to the organic EL element 1.

  In addition, the specific structure and shape in the implementation of the present invention may be other structures as long as the object of the present invention can be achieved.

  Hereinafter, examples according to the present invention will be described, but the present invention is not limited to these examples.

  The compounds used in this example are shown.

<Evaluation of compound>
Next, the physical properties of the compounds used in this example were measured. The measurement method and calculation method are shown below, and the measurement results and calculation results are shown in Table 5.

-Ionization potential It measured using the photoelectron spectrometer (the Riken Keiki Co., Ltd. product: AC-3) in air | atmosphere. Specifically, the measurement was performed by irradiating the material with light and measuring the amount of electrons generated by charge separation at that time. The results are shown in Table 1.

・ Singlet energy Substituting the wavelength value λ _edge [nm] at the intersection of the long-wavelength side tangent and the baseline (zero absorption) of the diluted toluene solution of the compound to be measured into the following conversion formula 1 Singlet energy was calculated. The results are shown in Table 1.
Conversion formula 1: EgS [eV] = 1239.85 / λ _edge
In this example, the absorption spectrum was measured with a Hitachi spectrofluorometer (device name: F-4500).

・ Affinity (electron affinity)
Using the measured values of the ionization potential Ip and singlet energy EgS of the compound measured by the method described above, the calculation was performed from the following formula. The results are shown in Table 1.
Af = Ip-EgS

  As shown in Table 1, the affinity of Compound BD1, which is an example of the second compound represented by General Formula (2), was greater than that of Compound BD-C1. Therefore, the affinity difference between compound BH1 and compound BD1, which is an example of the first compound represented by the general formula (1), is smaller than the affinity difference between compound BH1 and compound BD-C1.

<Production of organic EL element>
An organic EL element was produced as follows.

Example 1
A glass substrate (manufactured by Geomatic) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HI is first deposited on the surface on which the transparent electrode line is formed so as to cover the transparent electrode. A 10 nm compound HI film was formed to form a hole injection layer.
Following the formation of this HI film, Compound HT-1 was vapor-deposited, and an HT-1 film having a thickness of 75 nm was formed on the HI film to form a first hole transport layer.
Subsequent to the formation of the HT-1 film, the compound HT-2 was vapor-deposited, and an HT-2 film having a thickness of 15 nm was formed on the HT-1 film to form a second hole transport layer.
Further, a compound BH1 as a host material and a compound BD1 as a dopant material were co-deposited on the HT-2 film. Thus, a light emitting layer having a thickness of 25 nm was formed. The dopant material concentration was 4% by mass.
On this light emitting layer, the compound ET-1 was vapor-deposited to form an ET-1 film having a thickness of 25 nm to form a first electron transport layer.
Furthermore, the compound ET-2 was vapor-deposited on the ET-1 film to form a 10 nm-thick ET-2 film, thereby forming a second electron transport layer.
LiF was vapor-deposited on this ET-2 film to form a 1-nm thick LiF layer.
Metal Al was vapor-deposited on this LiF film to form a metal cathode having a thickness of 80 nm.
A device arrangement of the organic EL device of Example 1 is schematically shown as follows.
ITO (130) / HI (10) / HT-1 (75) / HT-2 (15) / BH1: BD1 (25, 4%) / ET-1 (25) / ET-2 (10) / LiF ( 1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the parentheses, the number expressed as a percentage indicates the ratio (mass%) of the component to be added, such as the dopant material in the light emitting layer. The same applies to the case where the element configurations of the following organic EL elements are schematically displayed.

(Comparative Example 1)
The organic EL device of Comparative Example 1 was produced in the same manner as in Example 1 except that the host material in the light emitting layer of the organic EL device of Example 1 was changed to Compound BH-C1.
A device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows.
ITO (130) / HI (10) / HT-1 (75) / HT-2 (15) / BH-C1: BD1 (25, 4%) / ET-1 (25) / ET-2 (10) / LiF (1) / Al (80)

(Comparative Example 2)
The organic EL device of Comparative Example 2 was the same as Example 1 except that the host material in the light emitting layer of the organic EL device of Example 1 was changed to Compound BH-C1, and the dopant material was changed to Compound BD-C1. Made.
A device arrangement of the organic EL device of Comparative Example 2 is schematically shown as follows.
ITO (130) / HI (10) / HT-1 (75) / HT-2 (15) / BH-C1: BD-C1 (25, 4%) / ET-1 (25) / ET-2 (10 ) / LiF (1) / Al (80)

(Comparative Example 3)
The organic EL device of Comparative Example 3 was produced in the same manner as in Example 1 except that the dopant material in the light emitting layer of the organic EL device of Example 1 was changed to Compound BD-C1.
A device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows.
ITO (130) / HI (10) / HT-1 (75) / HT-2 (15) / BH1: BD-C1 (25, 4%) / ET-1 (25) / ET-2 (10) / LiF (1) / Al (80)

<Evaluation of organic EL element>
The following evaluation was performed about the organic EL element which concerns on Example 1 and Comparative Examples 1-3. The evaluation results are shown in Table 2.

- As the drive voltage the current density is 10 mA / cm ^2, voltage when energized between the ITO and Al (Unit: V) was measured.

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 was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta). .

・ Current efficiency L / J and power efficiency η
The spectral radiance spectrum when a voltage was applied to the device so that the current density was 10.00 mA / cm ² was measured with the spectral radiance meter, and the current efficiency (unit: cd / A) and power efficiency η (unit: lm / W) were calculated.

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

・ Lifetime LT80
A voltage was applied to the device so that the current density was 50 mA / cm ^2, and the time (unit: h) until the luminance became 80% with respect to the initial luminance was measured.

As shown in Table 2, the organic EL device according to Example 1 includes a light emitting layer containing compound BH1 and compound BD1, and as a result, compared to the organic EL devices according to Comparative Examples 1 to 3. As a result, the luminous efficiency was improved, the life was extended, and the driving voltage was lowered.
The affinity of the compound BD1, which is an example of the second compound represented by the general formula (2), is larger than that of the compound BD-C1 used as a comparison. Therefore, it is considered that the organic EL element according to Example 1 has good electron injecting property to the light emitting layer and can reduce the driving voltage of the organic EL element. In the organic EL device according to Example 1, the difference between the affinity of compound BH1, which is an example of the first compound represented by the general formula (1), and the affinity of compound BD1 is small. Therefore, electron transfer from the dopant material to the host material is likely to occur, and it is considered that the recombination probability of electrons and holes has increased in the molecules of the host material. Furthermore, it is considered that the excitation energy from the host material to the dopant material is efficiently generated, and the light emission efficiency of the organic EL element is improved. In addition, since the compound BD1 has a higher affinity than the compound BD-C1, it is considered that recombination of electrons and holes easily occurs in the molecule of the dopant material. Also from this viewpoint, it is considered that the light emission efficiency of the organic EL element according to Example 1 could be improved.
In the organic EL device according to Comparative Example 1, the host material is the compound BH-C1, which is different from the first compound represented by the general formula (1). Therefore, compared with Example 1, the light emission efficiency is low, the lifetime is short, and the drive voltage is high.
Compared with Example 1, the organic EL elements according to Comparative Example 2 and Comparative Example 3 had a higher driving voltage and a shorter lifetime, but their luminous efficiency was particularly low. This is probably because the affinity difference between the compound BD-C1 used as the dopant material and the compound BH1 or compound BH-C1 used as the host material was large. In addition, it is considered that the compound BD-C1 has a singlet energy larger than that of the compound BH1 or the compound BH-C1 used as the host material, and the excitation energy did not efficiently transfer from the host material to the dopant material.

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

Claims (25)

A cathode,
The anode,
Having one or more organic layers disposed between the cathode and the anode;
The organic layer includes a light emitting layer,
The said light emitting layer contains the 1st compound represented by following General formula (1), and the 2nd compound represented by following General formula (2). The organic electroluminescent element characterized by the above-mentioned.

(In the general formula (1),
R _{101 to} R ₁₀₈ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by -Si (R ₁₁₁ ) ₃ ;
R ₁₁₁ is independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
R ₁₀₉ and R ₁₁₀ are each independently
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 R ₁₀₉ and R ₁₁₀ are substituted or unsubstituted condensed aromatic hydrocarbon groups, they are condensed aromatic hydrocarbon groups in which two or three six-membered rings are condensed.
In some cases, adjacent groups out of R _{101 to} R ₁₀₈ may be bonded to each other to form a ring.
However, when R ₁₀₉ is an unsubstituted phenyl group and R ₁₁₀ is a group represented by the following general formula (10), R ₁₁₃ in the following general formula (10) is substituted or unsubstituted. Or an aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. )

(When R ₁₀₉ is an unsubstituted phenyl group and R ₁₁₀ is a group represented by the following general formula (11), R ₁₁₄ in the following general formula (11) is an unsubstituted group. It is an aromatic hydrocarbon group having 6 to 14 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.)

(When R ₁₀₉ is an unsubstituted phenyl group and R ₁₁₀ is a group represented by the following general formula (12), R ₁₁₅ in the following general formula (12) is an unsubstituted group. It is an aromatic hydrocarbon group having 12 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.)

(In addition, when R ₁₀₉ is an unsubstituted 1-naphthyl group, R ₁₁₀ is
A group represented by the following general formula (13):
A group represented by the following general formula (14):
It is a substituted or unsubstituted aromatic hydrocarbon group having 12 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. )
(In the general formula (13), m is 5, and R ₁₁₆ is independently synonymous with R _{101 to} R _108. However, at least one of the five R ₁₁₆ is substituted or unsubstituted. An aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, and R ₁₁₆ is a benzene ring represented by the general formula (13). Bond to a carbon atom.
In the general formula (14), n is 7, and R ₁₁₇ is independently the same as R _{101 to} R ₁₀₈ . However, at least one of the seven R ₁₁₇ is 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. . R ₁₁₇ is bonded to the carbon atom of the naphthalene ring of the general formula (14). )

{[In the general formula (2),
Ar ²¹ and Ar ²² are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. However, Ar ²¹ and Ar ²² may be bonded to each other to form a ring or not form a ring.
L ^{20 to} L ²² are each independently a single bond or a linking group,
As the linking group in L ^{20 to} L ²² ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
n ₂ is an integer of 1 to 4, and when n ₂ is 2 or more, the plurality of Ar ²¹ , Ar ²² , and L ^{20 to} L ²² may be the same as or different from each other.
A is represented by the following general formula (2a). ]

[In the general formula (2a),
R ^{231 to} R ²³⁸ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms or a silyl group represented by —Si (R ²⁴¹ ) ₃ .
One set of R ²³¹ and R ²³² , R ²³² and R ²³³ , R ²³³ and R ²³⁴ , R ²³⁵ and R ²³⁶ , R ²³⁶ and R ²³⁷ , and R ²³⁷ and R ²³⁸ is represented by the following general formula (2b). Is a carbon atom that bonds to the structure.
R ²³⁹ and R ²⁴⁰ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by —Si (R ²⁴² ) ₃ .
R ²⁴¹ and R ²⁴² are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. ]

[In the general formula (2b),
* Is any of R ²³¹ and R ²³² , R ²³² and R ²³³ , R ²³³ and R ²³⁴ , R ²³⁵ and R ²³⁶ , R ²³⁶ and R ²³⁷ , and R ²³⁷ and R ^{238 in} the general formula (2a), respectively. Represents the bond position to a set of carbon atoms.
R ^{251 to} R ²⁵⁴ are independently the same as R ^{231 to} R ²³⁸ in the general formula (2). ]
In addition, n ₂ out of R ^{231 to} R ^{238 in the} general formula (2a) and R ^{251 to} R ^{254 in} the general formula (2b) are bonds that are bonded to L ²⁰ in the general formula (2). . } 2. The organic electroluminescence device according to claim 1, wherein the first compound represented by the general formula (1) is represented by the following general formula (15).
(In the general formula (15), R _{101 to} R ₁₀₈ , R _{121 to} R ₁₂₇ , R _{131 to} R ₁₃₇ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
However, at least one of R _{121 to} R ₁₂₇ and R _{131 to} R ₁₃₇ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 ~ 30 heterocyclic groups,
R ₁₂₁ and R ₁₂₂ , R ₁₂₂ and R ₁₂₃ , R ₁₂₃ and R ₁₂₄ , R ₁₂₄ and R ₁₂₅ , R ₁₂₅ and R ₁₂₆ , and at least one combination of R ₁₂₆ and R ₁₂₇ A ring structure fused to the naphthalene ring may be constructed. ) The organic electroluminescence device according to claim 2,
At least one of R _{121 to} R ₁₂₇ is 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. ,
At least one of R _{131 to} R ₁₃₇ is 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. An organic electroluminescence device characterized by that. 2. The organic electroluminescence device according to claim 1, wherein the first compound represented by the general formula (1) is represented by the following general formula (16).
(In the general formula (16), R _{101 to} R ₁₀₈ , R _{141 to} R ₁₄₅ , R _{151 to} R ₁₅₅ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1),
However, at least one of R _{141 to} R ₁₄₅ and R _{151 to} R ₁₅₅ is
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 10 ring carbon atoms,
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,
A ring structure in which at least one of R ₁₄₁ and R ₁₄₂ , R ₁₄₂ and R ₁₄₃ , R ₁₄₃ and R ₁₄₄ , and R ₁₄₄ and R ₁₄₅ is bonded to each other and condensed to a benzene ring is constructed. Also good. ) In the organic electroluminescent element according to claim 4,
At least one of R _{141 to} R ₁₄₅ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted group A cycloalkyl group having 3 to 10 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
At least one of R _{151 to} R ₁₅₅ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted group. An organic electroluminescence device, which is a cycloalkyl group having 3 to 10 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms which is substituted or unsubstituted. 2. The organic electroluminescence device according to claim 1, wherein the first compound represented by the general formula (1) is represented by the following general formula (17).
(In the general formula (17), R _{101 to} R ₁₀₈ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1);
R _{161 to} R ₁₆₅ are each independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a silyl group represented by -Si (R ₁₁₁ ) ₃ ;
R ₁₁₁ is independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
However, at least one of R _{161 to} R ₁₆₅ is 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. It is. ) 2. The organic electroluminescence device according to claim 1, wherein the first compound represented by the general formula (1) is represented by the following general formula (18).
(In the general formula (18), R _{101 to} R ₁₀₈ , R _{171 to} R ₁₇₇ , and R _{181 to} R ₁₈₅ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1).
However, when one of R _{171 to} R ₁₇₇ is a substituted or unsubstituted aromatic hydrocarbon group, the number of ring-forming carbons of the aromatic hydrocarbon group is 10 or more and 30 or less. ) The organic electroluminescent element according to claim 7, wherein the first compound represented by the general formula (18) is represented by the following general formula (181).
(In the general formula (181), R _{101 to} R ₁₀₈ , R _{175 to} R ₁₇₇ , and R _{181 to} R ₁₈₅ are independently the same as R _{101 to} R ₁₀₈ in the general formula (1).
However, at least one of R _{175 to} R ₁₇₇ is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. It is. ) The organic electroluminescence device according to claim 8, wherein the first compound represented by the general formula (181) is represented by any one of the following general formulas (182) to (186). Organic electroluminescence device.
(In the general formulas (182) to (186), R _{101 to} R ₁₀₈ and R _{191 to} R ₁₉₇ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1).
R < ₁₇₅ > -R <_177> is respectively independently synonymous with R _{< 175} > -R < ₁₇₇ > in the said General formula (181). ) The organic electroluminescence device according to claim 7,
The 1st compound represented by the said General formula (18) is represented by the following general formula (187), The organic electroluminescent element characterized by the above-mentioned.
(In the general formula (187), R _{101 to} R ₁₀₈ , R _{171 to} R ₁₇₄ , R _{181 to} R ₁₈₅ are each independently synonymous with R _{101 to} R ₁₀₈ in the general formula (1);
However, at least one of R _{171 to} R ₁₇₄ is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. It is. ) The organic electroluminescent device according to claim 1,
When at least one of R _{101 to} R ₁₁₀ is an aromatic hydrocarbon group, R _{101 to} R ₁₁₀ are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, Fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrysenyl group, benzo [b Selected from the group consisting of triphenylenyl, picenyl, and perylenyl groups;
When at least one of R _{101 to} R ₁₁₀ is a heterocyclic group, R _{101 to} R ₁₁₀ are each independently a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, Naphthyridinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl Group, imidazopyridinyl group, benztriazolyl group, carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, benzofuranyl group Benzothiophenyl group, benzoxazolyl group, benzothiazolyl group, benzisoxazolyl group, benzisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, piperidinyl An organic electroluminescence device characterized by being selected from the group consisting of a group, a pyrrolidinyl group, a piperazinyl group, a morpholyl group, a phenazinyl group, a phenothiazinyl group, and a phenoxazinyl group. The organic electroluminescent device according to claim 1,
When at least one of R _{101 to} R ₁₁₀ is an aromatic hydrocarbon group, R _{101 to} R ₁₁₀ are each independently selected from the group consisting of a phenyl group, a biphenyl group, and a naphthyl group;
When at least one of R _{101 to} R ₁₁₀ is a heterocyclic group, R _{101 to} R ₁₁₀ are each independently a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, Naphthyridinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl Group, imidazopyridinyl group, benztriazolyl group, carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, benzofuranyl group Benzothiophenyl group, benzoxazolyl group, benzothiazolyl group, benzisoxazolyl group, benzisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, piperidinyl An organic electroluminescence device characterized by being selected from the group consisting of a group, a pyrrolidinyl group, a piperazinyl group, a morpholyl group, a phenazinyl group, a phenothiazinyl group, and a phenoxazinyl group. The organic electroluminescent device according to claim 1,
When at least one of R _{101 to} R ₁₁₀ is an aromatic hydrocarbon group, R _{101 to} R ₁₁₀ are each independently a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group. Selected from the group consisting of
When at least one of R _{101 to} R ₁₁₀ is a heterocyclic group, R _{101 to} R ₁₁₀ are each independently 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3-dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, An organic electroluminescence device characterized by being selected from the group consisting of a 4-carbazolyl group and a 9-carbazolyl group. The organic electroluminescent element according to any one of claims 1 to 13, wherein the general formula (2a) is represented by any one of the following general formulas (2a-1) to (2a-3). An organic electroluminescence device characterized by comprising:

[In the general formula (2a-1) ~ (2a -3), R 231 ~R 238, R 239, R 240 is a ^{R 231 ~R 238, R 239,} R 240 at each general formula (2a) It is synonymous.
R ²⁵¹ to R ²⁵⁴ are each independently the same meaning as ^R 251 ^{to R 254} in the general formula (2b). ]   The organic electroluminescent element of Claim 14 WHEREIN: The said general formula (2a) is represented by the said general formula (2a-3), The organic electroluminescent element characterized by the above-mentioned. The organic electroluminescent element according to any one of claims 1 to 15, wherein R ²³³ and R ²³⁶ are a bond that bonds to L ²⁰ of the general formula (2). Organic electroluminescence device. The organic electroluminescence device according to any one of claims 1 to 16, wherein the general formula (2) is represented by the following general formula (21).

[In the general formula ^{(21), A, Ar 22} , L 20 ~L 22, and _{n 2,} ^A in each of the general formula ^{(2), Ar 22, L} 20 ~L 22, and _{n 2} and interchangeably is there.
R ^{211 to} R ²¹⁵ are each independently
Hydrogen atom,
A cyano group,
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a silyl group represented by —Si (R ²¹⁶ ) ₃ .
R ²¹⁶ is independently the same as R ²⁴¹ and R ²⁴² in the general formula (2a). ] The organic electroluminescent element according to any one of claims 1 to 16, wherein the general formula (2) is represented by the following general formula (22).

[In the general formula ^{(22), A, L 20} ~L 22, and _{n 2} is an ^A in each of the general formula ^{(2), L 20 ~L 22} , and the _{n 2} synonymous.
R ^{211 to} R ²¹⁵ and R ^{221 to} R ²²⁵ are each independently
Hydrogen atom,
A cyano group,
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a silyl group represented by —Si (R ²¹⁶ ) ₃ .
R ²¹⁶ is independently the same as R ²⁴¹ and R ²⁴² in the general formula (2a). ] The organic electroluminescent element according to any one of claims 1 to 16, wherein the general formula (2) is represented by the following general formula (23).

[In the general formula ^{(23), A, Ar 22} , L 20 ~L 22, and _{n 2,} ^A in each of the general formula ^{(2), Ar 22, L} 20 ~L 22, and _{n 2} and interchangeably is there.
R ^{211 to} R ²¹⁵ and R ^{261 to} R ²⁶⁸ are each independently
Hydrogen atom,
A cyano group,
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a silyl group represented by —Si (R ²¹⁶ ) ₃ .
R ²¹⁶ is independently the same as R ²⁴¹ and R ²⁴² in the general formula (2a). ] 20. The organic electroluminescence device according to claim 17, wherein R ^{211 to} R ²¹⁵ are each independently a hydrogen atom, a fluorine atom, a cyano group, a methyl group, a tertiary butyl group, An organic electroluminescence device characterized by being a phenyl group or a trimethylsilyl group. In the organic electroluminescent device according to any one of claims 1 to 20, L ²⁰ ~L ²² is an organic electroluminescent device, characterized in that both a single bond. In the organic electroluminescent device according to any one of claims 1 to 21, n ₂ is an organic electroluminescent device which is a 1 or 2.   23. The organic electroluminescence device according to claim 1, further comprising an electron transport layer between the light emitting layer and the cathode.   The organic electroluminescence device according to any one of claims 1 to 23, further comprising a hole transport layer between the light emitting layer and the anode.   An electronic device comprising the organic electroluminescence element according to any one of claims 1 to 24.