JP2015122379A - Organic electroluminescent element and electronic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide: an organic electroluminescent element which enables the reduction in drive voltage; and an electronic device having such an organic electroluminescent element.SOLUTION: An organic electroluminescent element comprises: an anode; a cathode; and a light-emitting layer. The light-emitting layer includes: a first compound expressed by the general formula (1); and a second compound expressed by the general formula (20). In the general formula (1), at least part of Rto Ris a substituted or unsubstituted aromatic hydrocarbon group with 6C-30C forming a ring, or a substituted or unsubstituted heterocyclic group with 5C-30C forming a ring, provided that Ris never an unsubstituted 2-naphthyl group.

Description

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

  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 includes 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.

  In recent years, a technique has been studied in which a light-emitting layer contains a host material and a dopant material, and the function is separated from the host material for excitation and the dopant material for light emission. For example, Patent Document 3 discloses an organic EL element using an anthracene compound as a host material and an aminopyrene compound as a dopant material.

Special table 2009-518831 JP2011-225546A International Publication No. 2010/122810

  However, in order to put the organic EL element into practical use, further reduction in driving voltage is required.

  The objective of this invention is providing the organic electroluminescent element which can reduce a drive voltage, and the electronic device provided with this organic electroluminescent element.

  An organic electroluminescence device according to one embodiment of the present invention includes an anode, a cathode, and a light emitting layer, and the light emitting layer includes a first compound represented by the following general formula (1), and the following general formula ( And a second compound represented by 20).

(In said general formula (1), R < ₁₀₁ > -R < ₁₀₅ > is a hydrogen atom or a substituent each independently, The substituent in R < ₁₀₁ > -R < ₁₀₅ > is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A silyl group represented by -Si (R ₁₀₀ ) ₃ ,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
R ₁₀₀ is independently a hydrogen atom or a substituent, and the substituent in R ₁₀₀ is
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
However, at least one of R _{101 to} R ₁₀₅ 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. Yes, R ₁₀₄ is not an unsubstituted 2-naphthyl group. )

(In the general formula (20),
L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ are each independently a single bond or a linking group,
As the linking group in L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ ,
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 formed by bonding two to three groups selected from the aromatic hydrocarbon groups;
A multiple linking group formed by bonding 2 to 3 groups selected from the heterocyclic group, or a group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon group and the heterocyclic group A multiple linking group;
Ar ²¹ and Ar ²³ are each independently a monovalent group derived from a ring structure represented by the following general formula (2b),
Ar ²² and Ar ²⁴ are each independently
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
It is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent group derived from a ring structure represented by the following general formula (2b). )

(In the general formula (2b),
X ²¹ is an oxygen atom or a sulfur atom,
R ²¹¹ to R ²¹⁸ are each independently
Hydrogen atom,
A single bond or a substituent bonded to L ²¹ , L ²² , L ²⁴ , or L ²⁵ ;
The substituents in R ²¹¹ to R ²¹⁸ have the same meanings as the substituents exemplified as the substituents in R _{101 to} R ₁₀₅ .
Among R ²¹¹ to R ²¹⁸ , substituents of two carbon atoms may be bonded to each other to form a ring structure.
However, one of R ²¹¹ to R ²¹⁸ in Ar ²¹ is a single bond bonded to L ²¹ in the general formula (20), and one of R ²¹¹ to R ²¹⁸ in Ar ²³ is the above a single bond to bond to ^{L 24} in the general formula (20).
In the general formula (20), when Ar ²² is a monovalent group derived from the ring structure represented by the general formula (2b), one of R ²¹¹ to R ²¹⁸ is , L ²² , and Ar ²⁴ is a monovalent group derived from the ring structure represented by the general formula (2b), among R ²¹¹ to R ²¹⁸ one ^is a single bond to bind to ^{L 25.} )

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

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which can reduce a drive voltage can be provided.

It is a figure which shows schematic structure of an example of the organic EL element which concerns on one Embodiment of this invention.

[Organic EL device]
The organic EL device in the first embodiment of the present invention includes a cathode, an anode, and an organic layer disposed between the cathode and the anode. The organic layer is composed of one layer or a plurality of layers.
In the organic EL device of the first embodiment of the present invention, at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, a single light emitting layer, or a known hole injection layer, hole transport layer, electron injection layer, electron transport layer, hole barrier layer, electron barrier layer, or the like. It may have a layer employed in the organic EL element. The organic layer may contain an inorganic compound.

As typical element configurations of the organic EL element, for example, the following configurations (a) to (e) can be given.
(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 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 of (d) is preferably used. However, of course, it is not limited to these.
The “light emitting layer” is an organic layer having a light emitting function.
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.
In the embodiment of the present invention, the term “electron transport layer” refers to an organic layer having the highest electron mobility among the organic layers in the electron transport region existing between the light emitting layer and the cathode. When the electron transport region is composed of one layer, the layer is an electron transport layer.

In FIG. 1, schematic structure of an example of the organic EL element in embodiment of this invention is shown.
An organic EL element 1 shown in FIG. 1 includes a 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 is configured by laminating a hole injection / transport layer 6, a light emitting layer 5, and an electron injection / transport layer 7 in order from the anode 3 side.

(Light emitting layer)
The light emitting layer 5 according to the present embodiment includes a first compound and a second compound.

-1st compound A 1st compound is represented by following General formula (1).

(In said general formula (1), R < ₁₀₁ > -R < ₁₀₅ > is a hydrogen atom or a substituent each independently, The substituent in R < ₁₀₁ > -R < ₁₀₅ > is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A silyl group represented by -Si (R ₁₀₀ ) ₃ ,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
R ₁₀₀ is independently a hydrogen atom or a substituent, and the substituent in R ₁₀₀ is
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
However, at least one of R _{101 to} R ₁₀₅ 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. Yes, R ₁₀₄ is not an unsubstituted 2-naphthyl group. )

In this embodiment, the substituent in R _{101 to} R ₁₀₅ is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, —Si (R ₁₀₀ ) It is a silyl group represented by ₃ , 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 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 is more preferable.

In the present embodiment, the aromatic hydrocarbon group in R _{101 to} R ₁₀₅ is more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 ring carbon atoms, and a substituted or unsubstituted ring. More preferably, it is an aromatic hydrocarbon group having 6 to 12 carbon atoms formed.

In this embodiment, the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R _{101 to} R ₁₀₅ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, or a pyrenyl group. Group, 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, It is preferably an aromatic hydrocarbon group selected from the group consisting of a picenyl group and a perylenyl group. Further, the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R _{101 to} R ₁₀₅ is selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group. It is more preferably an aromatic hydrocarbon group. These aromatic hydrocarbon groups may have a substituent.

In this embodiment, R ₁₀₄ or R ₁₀₃ 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 preferable that

In the present embodiment, when R ₁₀₄ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, R ₁₀₄ is a phenyl group, a biphenyl group, a terphenyl group, or 1-naphthyl. Group, anthryl group, 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] An aromatic hydrocarbon group selected from the group consisting of a chrycenyl group, a benzo [b] triphenylenyl group, a picenyl group, and a perylenyl group is preferable. R ₁₀₄ is more preferably an aromatic hydrocarbon group selected from the group consisting of a phenyl group, a biphenyl group, a 1-naphthyl group, a phenanthryl group, and a fluorenyl group. These aromatic hydrocarbon groups may have a substituent.
Thus, if _{R 104} is an aromatic hydrocarbon group in the first _{compound, R 104} is not a 2-naphthyl group.
In this embodiment, when R ₁₀₄ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, R _{101 to} R ₁₀₃ and R ₁₀₅ may be a hydrogen atom. preferable. In this case, the first compound is represented by the following general formula (10), and R ₁₀₄ has the same meaning as R ₁₀₄ .

In the present embodiment, R ₁₀₄ is preferably not a substituted or unsubstituted 2-naphthyl group, and more preferably not a substituted or unsubstituted naphthyl group.

  In the present embodiment, the first compound is also preferably represented by the following general formula (12).

In (Formula _{(12), R} 111 ~R ₁₁₅ are each independently a hydrogen atom or a _substituent, the substituent in R 111 _{to R 115} is mentioned as the substituent in the _R 101 _{to R 105} Synonymous with the substituents
In the general formula (12), among R _{111 to} R ₁₁₅ , substituents of two carbon atoms may be bonded to each other to form a ring structure. )

In the present embodiment, when R ₁₀₃ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, R ₁₀₃ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, Anthryl, phenanthryl, fluorenyl, pyrenyl, chrysenyl, fluoranthenyl, benzo [a] anthryl, benzo [c] phenanthryl, triphenylenyl, benzo [k] fluoranthenyl, benzo [g] It is preferably an aromatic hydrocarbon group selected from the group consisting of a chrycenyl group, a benzo [b] triphenylenyl group, a picenyl group, and a perylenyl group. R ₁₀₃ is more preferably an aromatic hydrocarbon group selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, and a fluorenyl group. These aromatic hydrocarbon groups may have a substituent.
In this embodiment, when R ₁₀₃ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, R ₁₀₁ , R ₁₀₂ , R ₁₀₄ , and R ₁₀₅ are hydrogen atoms. Preferably there is. In this case, the first compound is represented by the following general formula (11), and R ₁₀₃ has the same meaning as R ₁₀₃ .

  In the present embodiment, the first compound is also preferably represented by the following general formula (13).

(In said general formula (13), R < ₁₂₁ > -R < ₁₂₅ > is a hydrogen atom or a substituent each independently, and the substituent in R < ₁₂₁ > -R < ₁₂₅ > is mentioned as a substituent in said R < ₁₀₁ > -R < ₁₀₅ >. Synonymous with the substituents
In the general formula (13), among R _{121 to} R ₁₂₅ , substituents of two carbon atoms may be bonded to each other to form a ring structure. )

  Specific examples of the first compound are shown below, but the present invention is not limited to these exemplified compounds.

-Second compound The second compound according to this embodiment is represented by the following general formula (20).

(In the general formula (20),
L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ are each independently a single bond or a linking group,
As the linking group in L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ ,
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 formed by bonding two to three groups selected from the aromatic hydrocarbon groups;
A multiple linking group formed by bonding 2 to 3 groups selected from the heterocyclic group, or a group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon group and the heterocyclic group A multiple linking group;
Ar ²¹ and Ar ²³ are each independently a monovalent group derived from a ring structure represented by the following general formula (2b),
Ar ²² and Ar ²⁴ are each independently
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
It is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent group derived from a ring structure represented by the following general formula (2b). )

(In the general formula (2b),
X ²¹ is an oxygen atom or a sulfur atom,
R ²¹¹ to R ²¹⁸ are each independently
Hydrogen atom,
A single bond or a substituent bonded to L ²¹ , L ²² , L ²⁴ , or L ²⁵ ;
The substituents in R ²¹¹ to R ²¹⁸ have the same meanings as the substituents exemplified as the substituents in R _{101 to} R ₁₀₅ .
Among R ²¹¹ to R ²¹⁸ , substituents of two carbon atoms may be bonded to each other to form a ring structure.
However, one of R ²¹¹ to R ²¹⁸ in Ar ²¹ is a single bond bonded to L ²¹ in the general formula (20), and one of R ²¹¹ to R ²¹⁸ in Ar ²³ is the above a single bond to bond to ^{L 24} in the general formula (20).
In the general formula (20), when Ar ²² is a monovalent group derived from the ring structure represented by the general formula (2b), one of R ²¹¹ to R ²¹⁸ is , L ²² , and Ar ²⁴ is a monovalent group derived from the ring structure represented by the general formula (2b), among R ²¹¹ to R ²¹⁸ one ^is a single bond to bind to ^{L 25.} )

  As represented by the general formula (20), in the second compound according to this embodiment, the substituted amino group is bonded to the 1st and 6th positions of the pyrene ring, and the other 2nd to 5th positions of the pyrene ring. , 7 to 10 positions are not substituted.

In the general formula (2b), the structure of the general formula (2b) when one of R ²¹¹ to R ²¹⁸ is a single bond bonded to L ²¹ , L ²² , L ²⁴ , L ^25, etc. The following general formula (2b-1) to general formula (2b-4). Here, the following general formula (2b-1) indicates that R ²¹¹ in the general formula (2b) is a single bond, and does not indicate that it is a methyl group. The same applies to the other general formulas (2b-2) to (2b-4).

[In the general formulas (2b-1) to (2b-4), X ²¹ and R ^{211 to} R ²¹⁸ are each independently X ^{21 in the} general formula (2b) and R ²¹¹ in the general formula (2b). ~R ²¹⁸ as synonymous. ]

Further, in the general formula (2b), as an example in which the substituents of adjacent carbon atoms among R ²¹¹ to R ²¹⁸ are bonded to each other to form a ring structure, the following general formula (2b- 5) to (2b-7).

(In the general formulas (2b-5) to (2b-7), X ²¹ and R ^{211 to} R ²¹⁸ each independently represent X ^{21 in the} general formula (2b) and R ²¹¹ in the general formula (2b). ~R ²¹⁸ as synonymous.
R ^{221 to} R ²²⁴ are each independently synonymous with R ^{211 to} R ²¹⁸ in the general formula (2b). )

In the general formulas (2b) and (2b-1) to (2b-7), at least one of R ²¹¹ to R ²¹⁸ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. preferable.

In the present embodiment, at least one of R ²¹¹ to R ²¹⁸ is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

R ²¹¹ or R ²¹³ in Ar ²¹ of the general formula (20) is preferably bonded to L ²¹ with a single bond. Among these, Ar ²¹ is preferably represented by the general formula (2b-1) or (2b-3), and Ar ²¹ is more preferably represented by the general formula (2b-1).
In the present embodiment, R ²¹¹ in Ar ²¹ is preferably bonded to L ²¹ with a single bond. In this case, for example, it is represented by the following general formula (2a-1). In addition, R ²¹¹ in Ar ²³ is preferably bonded to L ²⁴ with a single bond. More preferably, R ²¹¹ in Ar ²¹ is bonded to L ²¹ with a single bond, and R ²¹¹ in Ar ²³ is bonded to L ²⁴ with a single bond.

In the general formula (2a-1), R ^{212 to} R ²¹⁸ , X ²¹ , Ar ²² , L ²¹ , L ^22, and L ²³ are R ^{212 to} R ²¹⁸ , X ²¹ , Ar ²² in the general formula (20). , L ²¹ , L ²² and L ²³ .
In the general formula (2a-1), a wavy line portion represents a bonding site with the pyrene ring represented by the general formula (20).

In this embodiment, at least one of ^{R 218} in ^{R 218,} and the ^{Ar 23} in the ^{Ar 21} is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or comb nothingness It is more preferably a substituted alkyl group having 1 to 10 carbon atoms.
Further, ^{R 218} in ^{Ar 21} and ^{Ar 23} in the general formula (20), i.e., that the ^{R 218} in formula (2b-1) is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Preferably, the substituted comb is an unsubstituted alkyl group having 1 to 10 carbon atoms.

In this embodiment, it is preferable that at least one of Ar ²² and Ar ²⁴ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

In the present embodiment, it is preferable that all of L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ are single bonds.
In this case, for example, the general formula (20) is represented by the following general formula (20a).

In the general formula (20a), Ar ²¹ , Ar ²² , Ar ²³ and Ar ²⁴ are each independently synonymous with Ar ²¹ , Ar ²² , Ar ²³ and Ar ²⁴ in the general formula (20).

In the general formula (20a), R ²¹¹ in Ar ²¹ is bonded to L ²¹ with a single bond, R ²¹¹ in Ar ²³ is bonded to L ²⁴ with a single bond, and L ^{21 to} L ^{When 26} is a single bond, the general formula (20a) is represented by the following general formula (20b), for example.

In the general formula (20b), R ^{212 to} R ²¹⁸ and R ^{232 to} R ²³⁸ are independently the same as R ^{212 to} R ²¹⁸ in the general formula (2b).
In the general formula (20b), X ²¹ and X ²² are independently the same as X ²¹ in the general formula (2b).
In the general formula (20b), Ar ²² and Ar ²⁴ are independently the same as Ar ²² and Ar ²⁴ in the general formula (20).

In the present embodiment, X ²¹ is preferably an oxygen atom. In the general formula (20b), X ²¹ and X ²² are preferably oxygen atoms.

  In the present embodiment, the general formula (20) is preferably represented by the following general formula (21).

In the general formula (21), Ar ²² and Ar ²⁴ are each independently the same as Ar ²² and Ar ²⁴ in the general formula (20), and R ²¹⁸ and R ²³⁸ are each independently the R ₁₀₁ it is synonymous with the substituent listed as a substituent in to R _105.

In the present embodiment, Ar ²² and Ar ²⁴ are preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and more preferably a substituted or unsubstituted phenyl group. .

  In the present embodiment, the general formula (20) is preferably represented by the following general formula (22).

(In the general formula (22), R ²²⁰ and R ²²¹ are each independently a hydrogen atom or a substituent, and the substituents in R ²²⁰ and R ²²¹ are listed as the substituents in R _{101 to} R ₁₀₅ . And is synonymous with the substituent
R ²¹⁸ and R ²³⁸ are each independently synonymous with the substituents exemplified as the substituent in R _{101 to} R ₁₀₅ ,
s and t are 5,
R ²²⁰ are each attached to a carbon atom building a 6-membered ring, substituent R ²²⁰ together two carbon atoms may be bonded to the ring structure is constructed together, R ²²¹ are each A ring structure may be constructed by bonding to a carbon atom constituting a 6-membered ring, and the substituents R ²²¹ of two carbon atoms are bonded to each other. )

In the present embodiment, R ²¹⁸ and R ²³⁸ are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. Is more preferable. R ²¹⁸ and R ²³⁸ are 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, amyl group, More preferably, it is an isoamyl group, a neopentyl group, a cyclopentyl group, or a cyclohexyl group.

  Specific examples of the second compound according to this embodiment are shown below, but the present invention is not limited to these exemplified compounds.

-Film thickness of light emitting layer The film thickness of the light emitting layer in the organic EL device of the present embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer and the adjustment of chromaticity may be difficult, and if it exceeds 50 nm, the driving voltage may increase.

-Content rate of the material in a light emitting layer The content rate of the 2nd compound in a light emitting layer does not have a restriction | limiting in particular, Although it can select suitably according to the objective, For example, 0.1 mass% or more and 70 mass% or less are It is preferably 1% by mass or more and 30% by mass or less. When the content of the second compound is 0.1% by mass or more, sufficient light emission can be obtained, and when it is 70% by mass or less, concentration quenching can be avoided.

-Combination of the first compound and the second compound In the present embodiment, the light emitting layer 5 includes the first compound represented by the general formula (1) and the first compound represented by the general formula (20). Contains two compounds. It is considered that the combination of the first compound and the second compound improves carrier injectability into the light emitting layer and lowers the driving voltage of the organic EL element. In the light emitting layer 5, it is preferable to employ a doping system in which the first compound is used as a host material and the second compound is used as a dopant material. When employing a doping system, the host material mainly has the function of encouraging recombination of electrons and holes and confining excitons in the light-emitting layer, and the dopant material is efficient for excitons obtained by recombination. It has a function to emit light. It can be said that the combination of the specific compound of the first compound as the host material is a suitable combination with the specific compound of the second compound as the dopant material.

(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 is made of, for example, polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, or polyethylene naphthalate. Examples include a plastic substrate. 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.
Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode. Any material that can be used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) 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- Aromatic amine compounds such as [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino [2,3-f: 20 , 30-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
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, CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] A carbazole derivative such as -9H-carbazole (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.
When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap on the side closer to the light emitting layer. An example of such a material is HT-2 used in Examples described later.

(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. In this embodiment, a benzimidazole compound can be suitably 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.

In this specification, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom. 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. For example, the benzene ring has 6 ring carbon atoms, the naphthalene ring has 10 ring carbon atoms, the pyridinyl group has 5 ring carbon atoms, and the furanyl group has 4 ring carbon atoms. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. In addition, for example, when a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons. In this specification, the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly) Of the ring compound) represents the number of atoms constituting the ring itself. An atom that does not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the pyridine ring has 6 ring atoms, the quinazoline ring has 10 ring atoms, and the furan ring has 5 ring atoms. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
Next, each substituent described in the general formula will be described.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms (sometimes referred to as an aryl group) in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, and 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 [g b] A triphenylenyl group, a picenyl group, a perylenyl group, and the like.
As an aryl group in this embodiment, it is preferable that ring formation carbon number is 6-20, More preferably, it is still more preferable that it is 6-12. Among the aryl 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 this embodiment (sometimes referred to as a heteroaryl group, a heteroaromatic cyclic group, or an aromatic heterocyclic group) include a pyridyl group, a 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, benztriazolyl group, carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, Oxadiazoli Group, thiadiazolyl group, benzofuranyl group, benzothiophenyl group, benzoxazolyl group, benzothiazolyl group, benzoisoxazolyl group, benzisothiazolyl group, benzooxadiazolyl 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. With respect to the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the present embodiment or substitution on the 9th-position nitrogen atom Alternatively, an unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.

  In this embodiment, the heterocyclic group may be a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18), for example.

  In the general formulas (XY-1) to (XY-18), X and Y are each independently a hetero atom, preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom. . The partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.

  In the present embodiment, the substituted or unsubstituted carbazolyl group may include, for example, a group obtained by further condensing a ring with a carbazole ring represented by the following formula. Such a group may also have a substituent. Also, the position of the joint can be changed as appropriate.

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 includes, for example, a dialkylarylsilyl group having two alkyl groups exemplified for the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. . 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 aryl 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 the Z ₂ include the aryl group 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 aryl group 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 aryl group 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 addition, examples of the substituent in the present embodiment such as a substituent in the case of “substituted or unsubstituted”, a ring structure A, a ring structure B, a ring structure E, a ring structure F, a substituent in the ring structure G, etc. Aryl group, heterocyclic group, alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group), alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylamino group, arylamino In addition to groups, alkylthio groups, and arylthio groups, alkenyl groups, alkynyl groups, aralkyl groups, halogen atoms, cyano groups, hydroxyl groups, nitro groups, and carboxy groups are exemplified.
Among the substituents mentioned here, an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and further, specific examples that are preferable in the description of each substituent Are preferred.
These substituents may be further substituted with the above substituents. A plurality of these substituents may be bonded to each other to form a ring.

  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 aryl group 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 XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms when the ZZ group is unsubstituted. The carbon number of the substituent when substituted is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
In the present specification, “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted, In this case, the number of substituent atoms is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

  In the present embodiment, a multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon group are bonded, and a multiple in which 2 to 4 groups selected from the heterocyclic group are bonded. Examples of a linking group or a multiple linking group formed by bonding two to four groups selected from the aromatic hydrocarbon group and the heterocyclic group include the aromatic hydrocarbon group and the heterocyclic group. Examples thereof include a divalent group formed by bonding 2 to 4 groups selected. 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 above for the aromatic hydrocarbon group and the heterocyclic group.

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

The light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer contains the first compound and the second compound. For example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state to a direct ground state.
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.

Further, for example, a barrier layer may be provided adjacent to the anode side or the cathode side of the light emitting layer. The barrier layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes, electrons, and excitons.
For example, when a barrier layer is disposed in contact with the cathode side of the light emitting layer, the barrier layer transports electrons, and the holes reach a layer (for example, an electron transport layer) on the cathode side of the barrier layer. Stop that.
In addition, when a barrier layer is disposed in contact with the anode side of the light emitting layer, the barrier layer transports holes, and the electrons reach a layer on the anode side of the barrier layer (for example, a hole transport layer). To stop doing.
Further, a barrier layer may be provided adjacent to the light emitting layer so that excitation energy does not leak from the light emitting layer to the peripheral layer. The excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer.
The light emitting layer and the barrier layer are preferably joined.

(Electronics)
An organic EL element according to an embodiment of the present invention is a display component such as an organic EL panel module, a display device such as a television, a mobile phone, a tablet or a personal computer, and an electronic device such as a light emitting device for lighting or a vehicle lamp. Can be used for

  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 as follows.

[Synthesis example]
A synthesis scheme of compound BH1 is shown below.

1,2-dimethoxyethane and toluene were added to Intermediate 1 (17 mmol) and Intermediate 2 (17 mmol), and tetrakis (triphenylphosphine) palladium (0) (0.84 mmol) and 2M aqueous sodium carbonate solution were added. The mixture was heated to reflux for 7 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, water was added and the resulting solid was collected by filtration, washed with water and methanol, and dried under reduced pressure. The obtained crude product was purified by silica gel column chromatography (toluene), and the obtained solid was washed with methanol and then dried under reduced pressure to obtain compound BH1 as a solid. Compound BH1 was identified by analysis of FD-MS (field desorption mass spectrum).
By following the above reaction and using a known alternative reaction or raw material tailored to the object, a compound within the scope of the claims can be synthesized.

[Example of manufacturing organic EL element]
Example 1
A glass substrate with an ITO transparent electrode of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
The glass substrate with the ITO transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and first, the compound HI-1 is deposited so as to cover the transparent electrode on the surface on which the ITO transparent electrode line is formed. Then, a HI-1 film having a film thickness of 5 nm was formed to form a hole injection layer.
Next, on this HI-1 film | membrane, compound HT-1 was vapor-deposited as a positive hole transport material, the HT-1 film | membrane with a film thickness of 110 nm was formed into a film, and the 1st positive hole transport layer was formed.
Subsequently, on this HT-1 film | membrane, compound HT-2 was vapor-deposited as a 2nd hole transport material, HT-2 film | membrane with a film thickness of 55 nm was formed into a film, and the 2nd hole transport layer was formed.
Further, on this HT-2 film, compound BH-1 as the first compound and compound BD1 as the second compound were co-evaporated. Thereby, a light emitting layer having a thickness of 25 nm was formed. In addition, the density | concentration of the 2nd compound in a light emitting layer was 5 mass%.
And on this light emitting layer, compound ET-1 was vapor-deposited and the ET-1 film | membrane with a film thickness of 25 nm was formed into a film, and the hole-blocking layer was formed.
Subsequently, the compound ET-2 and Liq (8-hydroxy-quinolinato-lithium) were co-evaporated on the ET-1 film to form an electron transport layer having a thickness of 15 nm. The concentration of Liq was 50% by mass.
Next, on this electron transport layer, Liq was vapor-deposited at a film formation rate of 0.1 angstrom / min to form a 1 nm-thick Liq film to form an electron injecting electrode (cathode).
And metal Al was vapor-deposited on this Liq film | membrane, the metal Al film | membrane with a film thickness of 80 nm was formed into a film, and the metal Al cathode was formed.
A device arrangement of the organic EL device of Example 1 is schematically shown as follows.
ITO (130) / HI-1 (5) / HT-1 (110) / HT-2 (55) / BH-1: BD1 (25, 95%: 5%) / ET-1 (25) / ET- 2: Liq (15, 50%: 50%) / Liq (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm). Similarly, in the parentheses, the number displayed as a percentage indicates the ratio (mass%) of each material in the light emitting layer.

Example 2
The organic EL device of Example 2 was produced in the same manner as in Example 1 except that the first compound in the light emitting layer of Example 1 was changed to Compound BH-2.
A device arrangement of the organic EL device of Example 2 is schematically shown as follows.
ITO (130) / HI-1 (5) / HT-1 (110) / HT-2 (55) / BH-2: BD1 (25, 95%: 5%) / ET-1 (25) / ET- 2: Liq (15, 50%: 50%) / Liq (1) / Al (80)

Example 3
The organic EL device of Example 3 was produced in the same manner as in Example 1 except that the first compound in the light emitting layer of Example 1 was changed to Compound BH-3.
A device arrangement of the organic EL device of Example 3 is schematically shown as follows.
ITO (130) / HI-1 (5) / HT-1 (110) / HT-2 (55) / BH-3: BD1 (25, 95%: 5%) / ET-1 (25) / ET- 2: Liq (15, 50%: 50%) / Liq (1) / Al (80)

Comparative example 1
The organic EL device of Comparative Example 1 was produced in the same manner as in Example 1 except that Compound BH-C was used instead of Compound BH-1 in the light emitting layer of Example 1.
A device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows.
ITO (130) / HI-1 (5) / HT-1 (110) / HT-2 (55) / BH-C: BD1 (25, 95%: 5%) / ET-1 (25) / ET- 2: Liq (15, 50%: 50%) / Liq (1) / Al (80)

[Evaluation of organic EL elements]
The organic EL elements produced in Examples 1 to 3 and Comparative Example 1 were evaluated as follows. The evaluation results are shown in Table 1.

-Driving voltage The voltage (unit: V) when electricity was passed between the ITO transparent electrode and the metal Al cathode so that the current density was 10 mA / cm ² 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 were measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta).

・ Main peak wavelength λ _p
The spectral radiance spectrum when a voltage was applied to the device so that the current density was 10 mA / cm ² was measured with the spectral radiance meter, and the main peak wavelength λ _p was obtained from the obtained spectral radiance spectrum.

・ 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 mA / cm ² was measured with the above spectral radiance meter, and the current efficiency (unit: cd / A) was calculated from the obtained spectral radiance spectrum. ) And power efficiency η (unit: lm / W).

  As shown in Table 1, the organic EL elements of Examples 1 to 3 in which the light emitting layer is configured by combining the first compound and the second compound according to the present invention are the same as the organic EL element of Comparative Example 1. Compared with this, the drive voltage could be reduced. The organic EL elements of Examples 1 to 3 emitted blue light as shown in Table 1, and were able to provide a blue light emitting organic EL element with a low driving voltage. In the organic EL device of Comparative Example 1, the light emitting layer was formed by combining a compound having a structure different from that of the first compound and the second compound, but the driving voltage was high. Furthermore, the organic EL elements of Examples 1 to 3 achieve a low driving voltage while exhibiting high power efficiency as compared with Comparative Example 1. Furthermore, the organic EL elements of Examples 1 and 2 achieve a low driving voltage while exhibiting higher current efficiency than that of Comparative Example 1.

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 (26)

An anode, a cathode, and a light emitting layer;
The said light emitting layer contains the 1st compound represented by the following general formula (1), and the 2nd compound represented by the following general formula (20), The organic electroluminescent element characterized by the above-mentioned.
(In said general formula (1), R < ₁₀₁ > -R < ₁₀₅ > is a hydrogen atom or a substituent each independently, The substituent in R < ₁₀₁ > -R < ₁₀₅ > is
Halogen atoms,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A silyl group represented by -Si (R ₁₀₀ ) ₃ ,
A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
R ₁₀₀ is independently a hydrogen atom or a substituent, and the substituent in R ₁₀₀ is
A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
However, at least one of R _{101 to} R ₁₀₅ 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. Yes, R ₁₀₄ is not an unsubstituted 2-naphthyl group. )
(In the general formula (20),
L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ are each independently a single bond or a linking group,
As the linking group in L ²¹ , L ²² , L ²³ , L ²⁴ , L ²⁵ and L ²⁶ ,
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 formed by bonding two to three groups selected from the aromatic hydrocarbon groups;
A multiple linking group formed by bonding 2 to 3 groups selected from the heterocyclic group, or a group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon group and the heterocyclic group A multiple linking group;
Ar ²¹ and Ar ²³ are each independently a monovalent group derived from a ring structure represented by the following general formula (2b),
Ar ²² and Ar ²⁴ are each independently
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
It is a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent group derived from a ring structure represented by the following general formula (2b). )
(In the general formula (2b),
X ²¹ is an oxygen atom or a sulfur atom,
R ²¹¹ to R ²¹⁸ are each independently
Hydrogen atom,
A single bond or a substituent bonded to L ²¹ , L ²² , L ²⁴ , or L ²⁵ ;
The substituents in R ²¹¹ to R ²¹⁸ have the same meanings as the substituents exemplified as the substituents in R _{101 to} R ₁₀₅ .
Among R ²¹¹ to R ²¹⁸ , substituents of two carbon atoms may be bonded to each other to form a ring structure.
However, one of R ²¹¹ to R ²¹⁸ in Ar ²¹ is a single bond bonded to L ²¹ in the general formula (20), and one of R ²¹¹ to R ²¹⁸ in Ar ²³ is the above a single bond to bond to ^{L 24} in the general formula (20).
In the general formula (20), when Ar ²² is a monovalent group derived from the ring structure represented by the general formula (2b), one of R ²¹¹ to R ²¹⁸ is , L ²² , and Ar ²⁴ is a monovalent group derived from the ring structure represented by the general formula (2b), among R ²¹¹ to R ²¹⁸ one ^is a single bond to bind to ^{L 25.} ) The organic electroluminescent device according to claim 1,
The organic hydrocarbon element, wherein the aromatic hydrocarbon group in R _{101 to} R ₁₀₅ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 20 ring carbon atoms. The organic electroluminescent device according to claim 1,
The organic hydrocarbon element, wherein the aromatic hydrocarbon group in R _{101 to} R ₁₀₅ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring carbon atoms. The organic electroluminescent device according to claim 1,
The aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R _{101 to} R ₁₀₅ is 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, and perylenyl An organic electroluminescence device, which is an aromatic hydrocarbon group selected from the group consisting of groups. The organic electroluminescent device according to claim 1,
The aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R _{101 to} R ₁₀₅ is an aromatic selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group. An organic electroluminescence device characterized by being a hydrocarbon group. In the organic electroluminescent element according to any one of claims 1 to 5,
R ₁₀₄ is a phenyl group, biphenyl group, terphenyl group, 1-naphthyl group, anthryl group, phenanthryl group, fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c ] An aromatic hydrocarbon group selected from the group consisting of a phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrysenyl group, benzo [b] triphenylenyl group, picenyl group, and perylenyl group An organic electroluminescence device characterized by that. In the organic electroluminescent element according to any one of claims 1 to 6,
The organic electroluminescent device, wherein R ₁₀₄ is an aromatic hydrocarbon group selected from the group consisting of a phenyl group, a biphenyl group, a 1-naphthyl group, a phenanthryl group, and a fluorenyl group. The organic electroluminescent device according to claim 1,
Said 1st compound is represented by following General formula (10), The organic electroluminescent element characterized by the above-mentioned.
(In the general formula (10), R ₁₀₄ has the same meaning as R ₁₀₄ in the general formula (1), but may not be an unsubstituted 2-naphthyl group.) In the organic electroluminescent element according to any one of claims 1 to 8,
R ₁₀₄ is not a substituted or unsubstituted 2-naphthyl group, and is an organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 8,
R ₁₀₄ is not a substituted or unsubstituted naphthyl group, and is an organic electroluminescence element. The organic electroluminescent device according to claim 1,
Said 1st compound is represented by following General formula (12), The organic electroluminescent element characterized by the above-mentioned.
In (Formula _{(12), R} 111 ~R ₁₁₅ are each independently a hydrogen atom or a _substituent, the substituent in R 111 _{to R 115} is mentioned as the substituent in the _R 101 _{to R 105} Synonymous with the substituents
In the general formula (12), among R _{111 to} R ₁₁₅ , substituents of two carbon atoms may be bonded to each other to form a ring structure. ) In the organic electroluminescent element according to any one of claims 1 to 7,
R ₁₀₃ is phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group, fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl. An aromatic hydrocarbon group selected from the group consisting of a group, a triphenylenyl group, a benzo [k] fluoranthenyl group, a benzo [g] chrysenyl group, a benzo [b] triphenylenyl group, a picenyl group, and a perylenyl group. An organic electroluminescence device characterized. In the organic electroluminescent element according to any one of claims 1 to 7,
R ₁₀₃ is an aromatic hydrocarbon group selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, and a fluorenyl group. The organic electroluminescent device according to claim 1,
Said 1st compound is represented by following General formula (11), The organic electroluminescent element characterized by the above-mentioned.
(In the general formula _{(11), R 103} has the same meaning as _{R 103} in the formula (1).) The organic electroluminescent device according to claim 1,
Said 1st compound is represented by following General formula (13), The organic electroluminescent element characterized by the above-mentioned.
(In said general formula (13), R < ₁₂₁ > -R < ₁₂₅ > is a hydrogen atom or a substituent each independently, and the substituent in R < ₁₂₁ > -R < ₁₂₅ > is mentioned as a substituent in said R < ₁₀₁ > -R < ₁₀₅ >. Synonymous with the substituents
In the general formula (13), among R _{121 to} R ₁₂₅ , substituents of two carbon atoms may be bonded to each other to form a ring structure. ) In the organic electroluminescent element according to any one of claims 1 to 15,
At least one of R ²¹¹ to R ^{218 in} the general formula (2b) is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the organic electroluminescence element. In the organic electroluminescent element according to any one of claims 1 to 16,
The organic electroluminescence device, wherein R ²¹¹ in Ar ²¹ is bonded to L ²¹ with a single bond, and R ²¹¹ in Ar ²³ is bonded to L ²⁴ with a single bond. In the organic electroluminescent element according to any one of claims 1 to 17,
Wherein ^{R 218} in ^{R 218} and the ^{Ar 23} in the ^{Ar 21} The organic electroluminescent device which is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. In the organic electroluminescent element according to any one of claims 1 to 18,
The organic electroluminescence device, wherein Ar ²² and Ar ²⁴ are substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms. In the organic electroluminescent element according to any one of claims 1 to 19,
The L ²¹ , the L ²² , L ²³ , L ²⁴ , L ²⁵ and the L ²⁶ are all single bonds. In the organic electroluminescent element according to any one of claims 1 to 20,
The said general formula (20) is represented by the following general formula (21), The organic electroluminescent element characterized by the above-mentioned.
(In the general formula (21), Ar ²² and Ar ²⁴ are independently the same as Ar ²² and Ar ²⁴ in the general formula (20), and R ²¹⁸ and R ²³⁸ are each independently the R it is synonymous with the substituent listed as a substituent in the ₁₀₁ to R _105.) In the organic electroluminescent element according to any one of claims 1 to 21,
Said general formula (20) is represented by the following general formula (22), The organic electroluminescent element characterized by the above-mentioned.
(In the general formula (22), R ²²⁰ and R ²²¹ are each independently a hydrogen atom or a substituent, and the substituents in R ²²⁰ and R ²²¹ are listed as the substituents in R _{101 to} R ₁₀₅ . R ²¹⁸ and R ²³⁸ are each independently synonymous with the substituents exemplified as the substituents in R _{101 to} R ₁₀₅ , and
s and t are 5,
R ²²⁰ are each attached to a carbon atom building a 6-membered ring, substituent R ²²⁰ together two carbon atoms may be bonded to the ring structure is constructed together, R ²²¹ are each A ring structure may be constructed by bonding to a carbon atom constituting a 6-membered ring, and the substituents R ²²¹ of two carbon atoms are bonded to each other. ) In the organic electroluminescent element according to any one of claims 1 to 22,
R ²¹⁸ is a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, amyl group, isoamyl group. , An organic electroluminescence device, wherein the organic electroluminescence device is a substituent selected from the group consisting of a neopentyl group, a cyclopentyl group, and a cyclohexyl group. In the organic electroluminescent element according to any one of claims 1 to 23,
An organic electroluminescence device comprising an electron transport layer between the light emitting layer and the cathode. In the organic electroluminescent element according to any one of claims 1 to 24,
An organic electroluminescence device comprising a hole transport layer between the light emitting layer and the anode.   The electronic device provided with the organic electroluminescent element as described in any one of Claim 1- Claim 25.