WO2014024880A1

WO2014024880A1 - Organic electroluminescent element and electronic apparatus

Info

Publication number: WO2014024880A1
Application number: PCT/JP2013/071248
Authority: WO
Inventors: 池田　剛; 裕勝伊藤
Original assignee: 出光興産株式会社
Priority date: 2012-08-10
Filing date: 2013-08-06
Publication date: 2014-02-13
Also published as: TW201412938A; JP2015216135A

Abstract

This organic electroluminescent element is characterized by: having a positive electrode, a negative electrode provided facing the positive electrode, and an organic layer provided between the positive electrode and the negative electrode; the organic layer being provided in the given order from the positive electrode side with a hole-transporting layer and a light-emitting layer; the hole-transporting layer containing a compound represented by general formula (1); and the light-emitting layer containing either a compound represented by general formula (10) or a compound represented by general formula (11).

Description

ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE

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

When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as an organic EL element), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin. When classified according to the light emission principle, the fluorescence type uses light emission by singlet excitons. On the other hand, in the phosphorescent type, since light emission by triplet excitons is used, it is known that the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.

Conventionally, in an organic EL element, an optimal element design has been made according to a light emission mechanism of a fluorescent type and a phosphorescent type.
For example, Patent Document 1 attempts to provide a fluorescent organic EL element having high emission efficiency and a long lifetime by setting an anthracene derivative as a host material of the light emitting layer to a specific structure.

JP 2009-40776 A

However, in recent years, an organic EL device having higher efficiency and longer life than the organic EL device described in Patent Document 1 has been desired.

An object of the present invention is to provide an organic EL element with high luminous efficiency and long life. Another object of the present invention is to provide an electronic apparatus provided with the organic EL element of the present invention.

The organic electroluminescence device according to one embodiment of the present invention is
The anode,
A cathode provided opposite to the anode;
An organic layer provided between the anode and the cathode,
The organic layer includes a hole transport layer and a light emitting layer in this order from the anode side,
The hole transport layer includes a compound represented by the following general formula (1),
The light emitting layer includes a light emitting material, a compound represented by the following general formula (10), and a compound represented by the following general formula (11).

(In the general formula (1), A ₁ and A ₂ each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon 2 Represents 30 to 30 aromatic heterocyclic groups.
Y ₁ to Y ₁₆ each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
L ₁ and L ₂ each independently represent a single bond or a divalent linking group.
However, at least one of A ₁ , A ₂ and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted Benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, substituted or unsubstituted benzo [b ] Fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl Group, substituted or unsubstituted phenanthrenyl group, It represents a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted binaphthyl group.
When Y ₁ to Y ₁₆ are all C (R), Y ₆ and Y ₁₁ are bonded by a single bond, L ₁ and L ₂ are a single bond, and A ₁ is a phenanthrenyl group, A ₂ Is not a phenanthrenyl group.
Furthermore, when Y ₁ to Y ₁₆ are all C (R), Y ₆ and Y ₁₁ are bonded by a single bond, and L ₁ and L ₂ are a single bond, R is not a fluorenyl group. In addition, when A ₁ is a fluorenyl group, A ₂ is not a phenyl group, a naphthyl group, or a fluorenyl group. )

(In the general formula (10) and the general formula (11), R ¹⁰¹ to R ¹⁰⁸ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted group. Substituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted ring forming carbon atoms An arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms,
Ar ³¹ to Ar ³³ , R ¹⁰⁹ , R ¹¹⁰ , and R ²¹ to R ²⁸ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, or a substituted or unsubstituted carbon number. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring carbon number having 6 to 20 carbon atoms Arylthio group, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms It is a hydrocarbon group or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and adjacent R ²¹ to R ²⁸ may form a ring.
However, at least one of Ar ³¹ to Ar ³³ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
In the general formula (10) and the general formula (11), when Ar ³¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, Ar ³¹ is substituted or unsubstituted. Substituted fluorenyl group.
In the general formula (11), when Ar ³¹ , Ar ³³ , R ¹⁰⁹ , and R ¹¹⁰ are hydrogen atoms, Ar ³² is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms. is there. )

In addition, the organic electroluminescence element according to one embodiment of the present invention is
The anode,
A cathode provided opposite to the anode;
An organic layer provided between the anode and the cathode,
The organic layer includes a hole transport layer and a light emitting layer in this order from the anode side,
The hole transport layer includes a compound represented by the following general formula (30), and the light emitting layer includes a compound represented by the following general formula (2A) and a light emitting material.

(In the general formula (30), A ₁ and A ₂ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5; Represents 30 to 30 aromatic heterocyclic groups.
Any two adjacent R ₄₁ to R ₄₄ are bonded to a partial structure represented by the following general formula (31). Any two adjacent R ₅₁ to R ₅₄ may be bonded to a partial structure represented by the following general formula (31). )

(R ₄₁ to R ₄₄ and R ₅₁ to R ₅₄ not bonded to the partial structure represented by the general formula (31) are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted A substituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, Substituted or unsubstituted arylthio group having 6 to 20 carbon atoms, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted A substituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
p and q are 3,
L ₁ and L ₂ each independently represents a single bond or a divalent linking group.
In the general formula (31), * represents a bonding site with the ring structure represented by the general formula (30),
One of Z ₁ and Z ₂ is a single bond, and the other is —O—, —S—, —CR ₆₅ R ₆₆ —, or —NR ₆₇ —;
R ₆₁ to R ₆₇ are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ˜40 trialkylsilyl group, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring formation It is a heterocyclic group having 5 to 50 atoms. )

(In the general formula (2A), R ¹⁰¹ to R ¹⁰⁸ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon number of 1 to 20 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring carbon atoms, and substituted or unsubstituted arylthio groups having 6 to 20 ring carbon atoms. A substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms,
Ar ¹⁰⁰¹ and Ar ¹⁰¹ 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. . Ar ¹⁰⁰ may form a ring with R ¹⁰¹ or R ^108, and Ar ¹⁰¹ may form a ring with R ¹⁰⁴ or R ¹⁰⁵ . )

According to the present invention, it is possible to provide an organic EL element with high luminous efficiency and long life.

It is a figure which shows schematic structure of an example of the organic EL element in 1st embodiment of this invention.

Hereinafter, the present invention will be specifically described.
[First Embodiment]
(Configuration of organic EL element)
First, the element configuration of the organic EL element will be described.
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, 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 “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 present invention, the 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 addition, in the phosphorescent organic EL device, as shown in the configuration (e), a barrier layer that does not necessarily have high electron mobility is used to prevent diffusion of excitation energy generated in the light emitting layer. The organic layer adjacent to the light emitting layer does not necessarily correspond to the electron transport layer.

In FIG. 1, schematic structure of an example of the organic EL element in embodiment of this invention is shown.
The organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
The organic layer 10 includes a hole transport layer 5 and a light emitting layer 6 in this order from the anode 3 side. In the present embodiment, the hole transport layer 5 and the light emitting layer 6 are adjacent to each other. Further, the organic EL element 1 includes a hole injection layer 7 between the anode 3 and the hole transport layer 5, and includes an electron injection / transport layer 8 between the cathode 4 and the light emitting layer 6. . Note that another hole transport layer different from the hole transport layer 5 may be provided between the hole injection layer 7 and the hole transport layer 5.
The light emitting layer 6 includes a host material and a fluorescent dopant material as a fluorescent light emitting material.
Further, an electron barrier layer may be provided on the phosphorescent light emitting layer 5 on the anode 3 side, and a hole barrier layer may be provided on the phosphorescent light emitting layer 5 on the cathode 4 side. With such a barrier layer, electrons and holes can be confined in the light emitting layer 6 and the exciton generation probability in the light emitting layer 6 can be increased.
The organic layer 10 may contain an inorganic compound.

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

(Anode and cathode)
The anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
The anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
When light emitted from the light emitting layer is extracted from the anode as in the present embodiment, it is preferable that the light transmittance in the visible region of the anode be greater than 10%. The sheet resistance of the anode is preferably several hundred Ω / □ (Ω / sq. Ohm per square) or less. The film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 μm, preferably 10 nm to 200 nm.

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

(Hole transport layer)
The hole transport layer 5 of the present embodiment is adjacent to the light emitting layer 6 on the anode 3 side and includes a compound represented by the following general formula (1).

In the general formula (1), A ₁ and A ₂ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 Represents 30 to 30 aromatic heterocyclic groups.

In the general formula (1), Y ₁ to Y ₁₆ each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent, or a carbazole skeleton. Represents. That is, the compound represented by the general formula (1) includes a case where it has a carbazole skeleton and a case where it has an azalated carbazole skeleton.

In the general formula (1), L ₁ and L ₂ each independently represent a single bond or a divalent linking group.
However, in the general formula (1), at least one of A ₁ , A ₂ and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenant. Renyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, Substituted or unsubstituted benzo [b] fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl Group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted Conversion of phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted binaphthyl group.

In the general formula (1), Y ₁ to Y ₁₆ are all C (R), Y ₆ and Y ₁₁ are bonded by a single bond, L ₁ and L ₂ are a single bond, and A ₁ Is a phenanthrenyl group, A ₂ is not a phenanthrenyl group.

Furthermore, in the general formula (1), when Y ₁ to Y ₁₆ are all C (R), Y ₆ and Y ₁₁ are bonded by a single bond, and L ₁ and L ₂ are a single bond, R Are not fluorenyl groups, and when A ₁ is a fluorenyl group, A ₂ is not a phenyl group, a naphthyl group, or a fluorenyl group.

In the general formula (1), at least one of Y ₁ to Y ₄ is C (R), at least one of Y ₅ to Y ₈ is C (R), and Y ₉ at least one of ~ _{Y 12} is a C _(R), at least one of Y 13 _{~ Y 16} is C (R).
One of Y ₅ to Y ₈ is C (R) and one of Y ₉ to Y ₁₂ is C (R), and these Rs represent bonds that are bonded to each other.
Several R in the said General formula (1) may mutually be same or different.

The compound represented by the general formula (1) contained in the hole transport layer 5 is represented by the following general formula (1-2), the following general formula (1-3), or the following general formula (1-4). It is preferable.

In the general formulas (1), (1-2) to (1-4), at least one of A ₁ and A ₂ is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, substituted or Unsubstituted benzophenanthrenyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or An unsubstituted picenyl group, a substituted or unsubstituted benzo [b] fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, substituted or Unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl group, substituted Properly is preferably unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted binaphthyl group.

In the general formulas (1), (1-2) to (1-4), A ₁ and A ₂ are each independently a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group. Substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or substituted or unsubstituted A carbazolyl group is preferred.

Moreover, the general formula (1), (1-2) ~ (1-4), _{A 1} and _{A 2} each independently represent a substituted or unsubstituted dibenzofuranyl group, Jibenzochio substituted or unsubstituted It is preferably a phenyl group or a substituted or unsubstituted carbazolyl group.

Further, in the general formulas (1), (1-2) to (1-4), the structure of the portion represented by L ₁ -A ₁ and the structure of the portion represented by L ₂ -A ₂ Are preferably different from each other.

Specific examples of the substituent of A ₁ and A ₂ in this embodiment and the substituent represented by R include a halogen atom, a cyano group, a substituted or unsubstituted straight chain or branched chain having 1 to 20 carbon atoms. A linear or branched alkyl group, a substituted or unsubstituted linear, branched or cyclic haloalkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms A linear, branched or cyclic divalent unsaturated hydrocarbon group having 1 to 20 carbon atoms, a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, A substituted or unsubstituted linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring forming carbon An arylthio group of formula 6-30, Or an unsubstituted linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted ring carbon number of 6 to 30 aromatic hydrocarbon groups and substituted or unsubstituted aromatic heterocyclic groups having 2 to 30 ring carbon atoms. These substituents may be plural, and when plural, they may be the same as or different from each other.
Note that R on adjacent ring-forming carbons may be bonded to each other to form a ring structure together with the ring-forming carbon.

Examples of the halogen atom in this embodiment include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In the present embodiment, the alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic, and examples of the linear or branched alkyl group include a methyl group, an ethyl group, and a propyl group. 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, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl Group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl group, hydroxymethyl group, 1 Hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-tri Hydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3- Dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodine Ethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2, 3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t- Butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 1,2-dinitroethyl group, 2,3-dinitro- t-butyl group, 1,2,3-trinitropropyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,1,3,3,3-hexafluoro-2-propyl Groups and the like.
Examples of the cyclic alkyl group (cycloalkyl group) include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a 4-methylcyclohexyl group, and 3,5-tetramethylcyclohexyl. Group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.

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

Examples of the linear, branched or cyclic alkylene group having 1 to 20 carbon atoms in the present embodiment include an ethylene group, a propylene group, and a butylene group.
Examples of the linear, branched or cyclic divalent unsaturated hydrocarbon group having 1 to 20 carbon atoms in the present embodiment include a 1,3-butadiene-1,4-diyl group.

The linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms in the present embodiment is represented as —OZ ¹ . Examples of Z ¹ include the alkyl group having 1 to 20 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
The aryloxy group having 6 to 30 ring carbon atoms in the present embodiment is represented by —OZ ² . Examples of Z ² include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. Examples of the aryloxy group include a phenoxy group.
The arylthio group having 6 to 30 ring carbon atoms in the general formulas (1) and (1-2) to (1-4) is represented by —SZ ³ . Examples of Z ³ include the following aromatic hydrocarbon groups having 6 to 30 ring carbon atoms.

Examples of the linear, branched or cyclic haloalkoxy group having 1 to 20 carbon atoms in the present embodiment include those in which the alkoxy group having 1 to 20 carbon atoms is substituted with one or more halogen groups. It is done.

Examples of the linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms in the present embodiment include a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group, a dimethylethylsilyl group, a dimethylisopropylsilyl group, and dimethyl Examples thereof include a propylsilyl group, a dimethylbutylsilyl group, a dimethyltertiarybutylsilyl group, and a diethylisopropylsilyl group.

Examples of the arylsilyl group having 6 to 30 carbon atoms in the present embodiment include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl tertiary butylsilyl group, and a triphenylsilyl group.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the present embodiment include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group. More specifically, a phenyl group, a naphthyl group, Phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, 9,9-dimethylfluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] phenanthrenyl group, naphtho [1,2-a] triphenylenyl group, dibenzo [a, c] triphenylenyl group, benzo [b] fluoranthenyl group, and the like.

Examples of the aromatic heterocyclic group having 2 to 30 ring carbon atoms or the aromatic heterocyclic group having 5 to 30 ring atoms in the present embodiment include a non-condensed aromatic heterocyclic ring and a condensed aromatic heterocyclic ring, More specifically, pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl Group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, thienyl group, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring , Dioxane ring, piperidine ring, morpholine ring, piperazine ring, carba Ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzimidazole ring, pyran ring, dibenzofuran ring, benzo [ c] A group formed from a dibenzofuran ring.

Examples of the divalent linking group represented by L ₁ and L ₂ in the present embodiment include a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent group. And an aromatic heterocyclic group having 2 to 10 ring carbon atoms.
Specific examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms include those having a divalent group as the aromatic hydrocarbon group having 6 to 30 ring carbon atoms described above. Can be mentioned.
Further, specific examples of the divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms include those mentioned above as the aromatic heterocyclic group having 2 to 30 ring carbon atoms. Things.

In the general formulas (1) and (1-2) to (1-4), Y ₁ to Y ₁₆ are preferably all C (R). That is, the compound represented by the general formula (1) contained in the hole transport layer 5 preferably has a structure in which two carbazole skeletons that are not azalated are connected. Furthermore, the compound represented by the general formula (1) preferably has two carbazole skeletons in the molecule.

In each of Y ₁ to Y ₈ and Y ₉ to Y _{16 in} the general formulas (1), (1-2) to (1-4), the number of substituents represented by R is 0 to 2 Preferably, it is 0 or 1, more preferably.
In addition, the compounds represented by the general formulas (1), (1-2) to (1-4) include a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group at a specific position. Selected from the group consisting of a substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, and a substituted or unsubstituted dibenzothiophenyl group Are preferably bonded.

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

In the case of “substituted or unsubstituted”, examples of the substituent include the aromatic hydrocarbon group, aromatic heterocyclic group, alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, haloalkyl group). Group), alkoxy group, aryloxy group, aralkyl group, haloalkoxy group, alkylsilyl group, dialkylarylsilyl group, alkyldiarylsilyl group, triarylsilyl group, halogen atom, cyano group, hydroxyl group, nitro group, and carboxy group Groups. In addition, an alkenyl group and an alkynyl group are also included.
Among the substituents mentioned here, an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable. Further, in the description of each substituent, Specific substituents that are preferred are preferred.
The term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

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.
In the present specification, the “carbon number ab” in the expression “substituted or unsubstituted XX group having carbon number ab” represents the number of carbons when the XX group is unsubstituted. The number of carbon atoms of the substituent when the XX group is substituted is not included.
In the compound described below or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

In the present embodiment, examples of the compound contained in the hole transport layer 5 include the following compounds. In the following structural formula, D represents deuterium.

(Light emitting layer)
The light emitting layer of the organic EL element has the following functions.
That is,
(1) injection function; a function capable of injecting holes from the anode or hole injection layer when an electric field is applied, and a function of injecting electrons from the cathode or electron injection layer;
(2) Transport function; function to move injected charges (electrons and holes) by the force of electric field,
(3) Luminescent function; a function to provide a field for recombination of electrons and holes and connect this to light emission,
There is.

However, there may be a difference in the ease with which holes are injected and the ease with which electrons are injected, and the transport capability represented by the mobility of holes and electrons may be large or small.
As a method for forming the light emitting layer, for example, a known method such as an evaporation method, a spin coating method, or an LB method can be applied.

The light emitting layer is preferably a molecular deposited film.
Here, the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state. Can be classified from a thin film (accumulated film) formed by the LB method according to a difference in an agglomerated structure and a higher-order structure and a functional difference resulting therefrom.
The light emitting layer can also be formed by dissolving a binder such as a resin and a material compound in a solvent to form a solution, and then thinning the solution by a spin coating method or the like.

-Host material The host material contained in the light emitting layer of this embodiment is a compound represented by following General formula (2).

In the general formula (2), R ¹⁰¹ to R ¹⁰⁸ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon group having 1 to 20 carbon atoms. An alkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, A substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.

In the general formula (2), any one of R ¹⁰⁹ to R ¹¹³ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom. A heterocyclic group of formula 5 to 30, and other R ¹⁰⁹ to R ¹¹³ are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted group An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring carbon number 6 Arylthio group having ˜20, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted Aromatic hydrocarbon group formed having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group ring atoms 5-50.

In the general formula (2), Ar ¹⁰¹ 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. .

In this embodiment, the host material included in the light emitting layer is preferably either a compound represented by the following general formula (10) or a compound represented by the following general formula (11).

In the general formula (10) and the general formula (11), R ¹⁰¹ to R ¹⁰⁸ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted group. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring carbon number. A 6-20 arylthio group, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.
Ar ³¹ to Ar ³³ , R ¹⁰⁹ , R ¹¹⁰ , and R ²¹ to R ²⁸ each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, or a substituted or unsubstituted carbon number. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring carbon number having 6 to 20 carbon atoms Arylthio group, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms It is a hydrocarbon group or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and adjacent R ²¹ to R ²⁸ may form a ring.
However, at least one of Ar ³¹ to Ar ³³ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
In the general formulas (10) and (11), when Ar ³¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, Ar ³¹ is substituted or unsubstituted fluorenyl. It is a group.

In this embodiment, in the general formula (11), when Ar ³¹ , Ar ³³ , R ¹⁰⁹ , and R ¹¹⁰ are hydrogen atoms, Ar ³² is a substituted or unsubstituted aromatic group having 10 to 30 ring carbon atoms. Group hydrocarbon group. In this case, Ar ³² is preferably a substituted or unsubstituted naphthyl group.

In this embodiment, in the general formula (10) and the general formula (11), when Ar ³¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, the following general formula ( 12) and the following general formula (13) are preferable.

In the general formula (12) and the general formula (13), R ³¹ and R ³² are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
R ³³ to R ³⁷ are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ˜40 trialkylsilyl group, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring formation It is a heterocyclic group having 5 to 50 atoms.
m is 4.

Next, a specific example of the compound contained in the light emitting layer of the present embodiment is shown, but the present invention is not limited to this specific example.

(Dopant material)
The dopant material is selected from fluorescent materials that exhibit fluorescent emission.
Specific examples of the dopant material include naphthalene derivatives, anthracene derivatives, pyrene derivatives, chrysene derivatives, fluoranthene derivatives, indenoperylene derivatives, pyromethene boron complex compounds, compounds having a pyromethene skeleton or metal complexes thereof, diketopyrrolo Examples include pyrrole derivatives and perylene derivatives.
Examples of naphthalene derivatives include bisarylaminonaphthalene derivatives and aryl-substituted naphthalene derivatives, and examples of anthracene derivatives include bisarylaminoanthracene derivatives and aryl group-substituted anthracene derivatives. Examples of the pyrene derivative include bisarylaminopyrene derivatives and aryl group-substituted pyrene derivatives. Examples of the chrysene derivatives include bisarylaminochrysene derivatives and aryl-substituted chrysene derivatives. It is selected from fluoranthene derivatives, pyrene derivatives, arylacetylene derivatives, fluorene derivatives, boron complexes, perylene derivatives, oxadiazole derivatives, anthracene derivatives, chrysene derivatives, and the like. Preferably, a fluoranthene derivative, a pyrene derivative, and a boron complex are used.

There is no restriction | limiting in particular in content in the light emitting layer of dopant material, Although it can select suitably according to the objective, For example, 0.1 to 70 mass% is preferable, and 1 to 30 mass% is preferable. Is more preferable. When the content of the dopant material 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.

In the present embodiment, the emission color of the dopant material contained in the light emitting layer is not particularly limited, but is preferably a fluorescent light emitting dopant material that emits blue light having a main peak wavelength of 480 nm or less. The main peak wavelength refers to the peak wavelength of the emission spectrum that maximizes the emission intensity in the emission spectrum measured in a toluene solution having a concentration of 10 ⁻⁵ mol / liter to 10 ⁻⁶ mol / liter.
A dopant material having such a main peak wavelength is doped into the host material represented by the general formula (2) to form a light emitting layer, and the hole transport layer adjacent to the anode side of the light emitting layer has the general formula By including the compound represented by (1), the organic EL device has high efficiency and long life.

(Hole injection / transport layer)
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a low ionization energy.
In the present embodiment, the hole injection / transport layer has at least a hole transport layer containing a compound represented by the general formula (2), and may have a hole injection layer in addition to this. Or may have another hole transport layer. Further, the hole injection / transport layer is formed from the anode side, the hole injection layer, the first hole transport layer, the second hole transport layer (a hole transport layer containing a compound represented by the general formula (2)) ) May be laminated in this order.
As a material for forming the hole injection layer and the hole transport layer, a material that transports holes to the light emitting layer with lower electric field strength is preferable. For example, an aromatic amine compound is preferably used. As the material for the hole injection layer, a porphyrin compound, an aromatic tertiary amine compound or a styrylamine compound is preferably used. It is preferable to use it.
As the aromatic amine compound, for example, an aromatic amine derivative represented by the following general formula (A1) is preferably used.

In the general formula (A1), Ar ¹ to Ar ⁴ are each independently an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, an aromatic heterocyclic group having 2 to 40 ring carbon atoms, It represents a group in which the aromatic hydrocarbon group and the aromatic heterocyclic group are bonded, or a group in which the aromatic hydrocarbon group and the aromatic heterocyclic group are bonded. However, the aromatic hydrocarbon group and aromatic heterocyclic group mentioned here may have a substituent.

In the general formula (A1), L is a linking group, a divalent aromatic hydrocarbon group having 6 to 50 ring carbon atoms, and a divalent aromatic heterocyclic ring having 5 to 50 ring carbon atoms. A group, or two or more aromatic hydrocarbon groups or aromatic heterocyclic groups, a single bond, an ether bond, a thioether bond, an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or amino Represents a divalent group obtained by bonding with a group. However, the divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group mentioned here may have a substituent.

Specific examples of the compound represented by the general formula (A1) are shown below, but are not limited thereto.

An aromatic amine represented by the following general formula (A2) is also preferably used for forming the hole injection / transport layer.

In the general formula (A2), the definitions from Ar ¹ to Ar ³ are the same as the definitions from Ar ¹ to Ar ^{4 in} the general formula (A1). Although the specific example of a compound represented by general formula (A2) below is described, it is not limited to these.

(Electron injection / transport layer)
The electron injection / transport layer is a layer that assists injection of electrons into the light emitting layer, and has a high electron mobility. The electron injection layer is provided to adjust the energy level, for example, to alleviate a sudden change in the energy level. The electron injection / transport layer includes at least one of an electron injection layer and an electron transport layer.
This embodiment preferably has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer preferably contains a nitrogen-containing ring derivative as a main component. Here, the electron injection layer may be a layer that functions as an electron transport layer.
“As a main component” means that the electron injection layer contains 50% by mass or more of a nitrogen-containing ring derivative.

As the electron transporting material used for the electron injection layer, an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable. Further, as the nitrogen-containing ring derivative, an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton is preferable.
As this nitrogen-containing ring derivative, for example, a nitrogen-containing ring metal chelate complex represented by the following general formula (B1) is preferable.

R ² to R ⁷ in formula (B1) are independently a hydrogen atom, a halogen atom, an oxy group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, an alkoxy group, an aryloxy group, or an alkoxycarbonyl group. Or an aromatic heterocyclic group, which may have a substituent.
Examples of the halogen atom include fluorine, chlorine, bromine and iodine. Examples of the optionally substituted amino group include an alkylamino group, an arylamino group, and an aralkylamino group.

The alkoxycarbonyl group is represented as —COOY ′, and examples of Y ′ include the same as the alkyl group. The alkylamino group and the aralkylamino group are represented as —NQ ¹ Q ² . Specific examples of Q ¹ and Q ² are independently the same as those described for the alkyl group and the aralkyl group, and preferred examples are also the same. One of Q ¹ and Q ² may be a hydrogen atom. The aralkyl group is a group in which a hydrogen atom of the alkyl group is substituted with the aryl group.
The arylamino group is represented by —NAr ¹ Ar ^2, and specific examples of Ar ¹ and Ar ² are the same as those described for the non-condensed aromatic hydrocarbon group and the condensed aromatic hydrocarbon group, respectively. . One of Ar ¹ and Ar ² may be a hydrogen atom.

M is aluminum (Al), gallium (Ga) or indium (In), and is preferably In.
L in the general formula (B1) is a group represented by the following general formula (B2) or (B3).

In the general formula (B2), R ⁸ to R ¹² are independently a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure. . This hydrocarbon group may have a substituent.
In the general formula (B3), R ¹³ to R ²⁷ are independently a hydrogen atom or a hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other form a cyclic structure. Also good. This hydrocarbon group may have a substituent.
Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R ⁸ to R ¹² and R ¹³ to R ^{27 in the} general formula (B2) and the general formula (B3) include those in the general formula (B1). those from R ² similar to the specific examples to R ⁷ can be exemplified.
In addition, when the groups adjacent to each other from R ⁸ to R ¹² and R ¹³ to R ²⁷ form a cyclic structure, examples of the divalent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, diphenylmethane- Examples include 2,2′-diyl group, diphenylethane-3,3′-diyl group, and diphenylpropane-4,4′-diyl group.

The electron transport layer preferably contains at least one of nitrogen-containing heterocyclic derivatives represented by the following general formulas (B4) to (B6).

In the general formulas (B4) to (B6), R is a hydrogen atom, an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, or a condensed aromatic hydrocarbon having 6 to 60 ring carbon atoms. Group, a pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.
n is an integer of 0 or more and 4 or less.

In the general formulas (B4) to (B6), R ¹ is an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.

In the general formulas (B4) to (B6), R ² and R ³ independently represent a hydrogen atom, an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, or 6 to 60 ring carbon atoms. The following condensed aromatic hydrocarbon groups, pyridyl groups, quinolyl groups, alkyl groups having 1 to 20 carbon atoms, or alkoxy groups having 1 to 20 carbon atoms.

In the general formulas (B4) to (B6), L represents an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, and pyridinylene. Group, quinolinylene group, or fluorenylene group.

In the general formulas (B4) to (B6), Ar ¹ represents an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridinylene group and a quinolinylene group;

In the general formulas (B4) to (B6), Ar ² is an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.

In the general formulas (B4) to (B6), Ar ³ represents an aromatic hydrocarbon group having 6 to 60 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 60 ring carbon atoms, A pyridyl group, a quinolyl group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or a group represented by “—Ar ¹ —Ar ² ” (Ar ¹ and Ar ² are The same).

Further, the condensed aromatic hydrocarbons mentioned in the description of R, R ¹ , R ² , R ³ , L, Ar ¹ , Ar ² , and Ar ^{3 in} the formulas (B4) to (B6) The group, pyridyl group, quinolyl group, alkyl group, alkoxy group, pyridinylene group, quinolinylene group and fluorenylene group may have a substituent.

As the electron transport compound used for the electron injection layer or the electron transport layer, 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable. As a specific example of the metal complex of 8-hydroxyquinoline or a derivative thereof, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used. Can do. And as an oxadiazole derivative, the following can be mentioned.

In each general formula of these oxadiazole derivatives, Ar ¹⁷ , Ar ¹⁸ , Ar ¹⁹ , Ar ²¹ , Ar ²² and Ar ²⁵ are each an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, or a ring forming carbon number. 6 or more and 40 or less condensed aromatic hydrocarbon group.
However, the aromatic hydrocarbon group and condensed aromatic hydrocarbon group mentioned here may have a substituent. Ar ¹⁷ and Ar ¹⁸ , Ar ¹⁹ and Ar ²¹ , Ar ²² and Ar ²⁵ may be the same as or different from each other.
Examples of the aromatic hydrocarbon group or condensed aromatic hydrocarbon group mentioned here include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group. And as a substituent to these, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyano group, etc. are mentioned.

In each of the general formulas of these oxadiazole derivatives, Ar ²⁰ , Ar ^23, and Ar ²⁴ are divalent aromatic hydrocarbon groups having 6 to 40 ring carbon atoms, or 2 having 6 to 40 ring carbon atoms. Valent condensed aromatic hydrocarbon group.
However, the aromatic hydrocarbon group and condensed aromatic hydrocarbon group mentioned here may have a substituent.
Ar ²³ and Ar ²⁴ may be the same as or different from each other.
Examples of the divalent aromatic hydrocarbon group or the divalent condensed aromatic hydrocarbon group mentioned here include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group. And as a substituent to these, a C1-C10 alkyl group, a C1-C10 alkoxy group, a cyano group, etc. are mentioned.

As these electron transport compounds, those having good thin film forming properties are preferably used. Specific examples of these electron transfer compounds include the following.

The nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following general formula, and includes a nitrogen-containing compound that is not a metal complex. For example, a 5-membered or 6-membered ring containing a skeleton represented by the following general formula (B7) and a structure represented by the following general formula (B8) can be given.

In the general formula (B8), X represents a carbon atom or a nitrogen atom. Z ₁ and Z ₂ each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.

The nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, a skeleton obtained by combining the general formulas (B7) and (B8) or the general formula (B7) with the following general formula (B9) is used. The nitrogen-containing aromatic polycyclic organic compound having is preferable.

The nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following general formula.

In each general formula of these nitrogen-containing heterocyclic groups, R represents an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and a ring forming carbon number. An aromatic heterocyclic group having 2 to 40 carbon atoms, a condensed aromatic heterocyclic group having 2 to 40 ring carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms.
In each general formula of these nitrogen-containing heterocyclic groups, n is an integer of 0 or more and 5 or less, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.

Furthermore, preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following general formula (B10).
HAr-L ¹ -Ar ¹ -Ar ² (B10)
In the general formula (B10), HAr is a nitrogen-containing heterocyclic group having 1 to 40 ring carbon atoms.
In the general formula (B10), L ¹ represents a single bond, an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and a ring forming carbon number. An aromatic heterocyclic group having 2 or more and 40 or less, or a condensed aromatic heterocyclic group having 2 to 40 ring carbon atoms.

In General Formula (B10), Ar ¹ is a divalent aromatic hydrocarbon group having 6 to 40 ring carbon atoms.
In General Formula (B10), Ar ² represents an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and 2 to 40 ring carbon atoms. The following aromatic heterocyclic groups or condensed aromatic heterocyclic groups having 2 to 40 ring carbon atoms.

In addition, the nitrogen-containing heterocyclic group, the aromatic hydrocarbon group, the condensed aromatic hydrocarbon group, and the aromatic complex mentioned in the description of HAr, L ¹ , Ar ¹ , and Ar ^{2 in} the general formula (B10) The ring group and the condensed aromatic heterocyclic group may have a substituent.

HAr in the formula of the general formula (B10) is selected from the following group, for example.

L ¹ in the formula (B10) is, for example, selected from the following group.

Ar ¹ in the formula (B10) is, for example, selected from the following arylanthranyl groups.

In the general formula of the arylanthranyl group, R ¹ to R ¹⁴ are independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or ring-forming carbon. An aryloxy group having 6 to 40 carbon atoms, an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and 2 to 40 ring carbon atoms. It is an aromatic heterocyclic group or a condensed aromatic heterocyclic group having 2 to 40 ring carbon atoms.

In the general formula of the arylanthranyl group, Ar ³ represents an aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a condensed aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and 2 or more ring carbon atoms. An aromatic heterocyclic group having 40 or less or a condensed aromatic heterocyclic group having 2 to 40 ring carbon atoms.

However, R ¹ to R ^{14 in} the general formula of the arylanthranyl group, and the aromatic hydrocarbon group, condensed aromatic hydrocarbon group, aromatic heterocyclic group, and condensed aromatic heterocyclic group mentioned in the description of Ar ³ The cyclic group may have a substituent.
Further, any of R ¹ to R ⁸ may be a nitrogen-containing heterocyclic derivative which is a hydrogen atom.

In the general formula of the arylanthranyl group, Ar ² is selected from the following group, for example.

In addition to the nitrogen-containing aromatic polycyclic organic compound as the electron transfer compound, the following compounds (see JP-A-9-3448) are also preferably used.

In the general formula of the nitrogen-containing aromatic polycyclic organic compound, R ¹ to R ⁴ independently represent a hydrogen atom, an aliphatic group, an aliphatic cyclic group, a carbocyclic aromatic cyclic group, or a heterocyclic group. To express. However, the aliphatic group, aliphatic cyclic group, carbocyclic aromatic ring group, and heterocyclic group mentioned here may have a substituent.
In the general formula of this nitrogen-containing aromatic polycyclic organic compound, X ¹ and X ² independently represent an oxygen atom, a sulfur atom, or a dicyanomethylene group.

In addition, the following compounds (see JP 2000-173774 A) are also preferably used as the electron transfer compound.

In the general formula, R ¹ , R ² , R ^3, and R ⁴ are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following general formula.

In the above general formula, R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are the same or different groups, and hydrogen atom or at least one of them is a saturated or unsaturated alkoxyl group, alkyl group, amino group A group or an alkylamino group.

Furthermore, the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.

The thickness of the electron injection layer or the electron transport layer is not particularly limited, but is preferably 1 nm or more and 100 nm or less.
Moreover, as a constituent component of the electron injection layer, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.

As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved. Specifically, preferred alkali metal chalcogenides include, for example, lithium oxide (Li ₂ O), potassium oxide (K ₂ O), sodium sulfide (Na ₂ S), sodium selenide (Na ₂ Se), and sodium oxide (Na ₂ O). Preferred alkaline earth metal chalcogenides include, for example, calcium oxide (CaO), barium oxide (BaO), strontium oxide (SrO), beryllium oxide (BeO), barium sulfide (BaS), and calcium selenide (CaSe). . Examples of preferable alkali metal halides include lithium fluoride (LiF), sodium fluoride (NaF), potassium fluoride (KF), lithium chloride (LiCl), potassium chloride (KCl), and sodium chloride (NaCl). ) And the like. Examples of preferable alkaline earth metal halides include calcium fluoride (CaF ₂ ), barium fluoride (BaF ₂ ), strontium fluoride (SrF ₂ ), magnesium fluoride (MgF ₂ ), and beryllium fluoride. Examples thereof include fluorides such as (BeF ₂ ) and halides other than fluorides.

Moreover, as a semiconductor, barium (Ba), calcium (Ca), strontium (Sr), ytterbium (Yb), aluminum (Al), gallium (Ga), indium (In), lithium (Li), sodium (Na) , Cadmium (Cd), magnesium (Mg), silicon (Si), tantalum (Ta), antimony (Sb), oxide containing at least one element of zinc (Zn), nitride or oxynitride alone Or the combination of 2 or more types is mentioned. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, so that pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
When such an insulator or semiconductor is used, the preferable thickness of the layer is about 0.1 nm to 15 nm. Moreover, even if the electron injection layer in this invention contains the above-mentioned reducing dopant material, it is preferable.

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

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

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

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

The addition form of the electron donating dopant and the organometallic complex is preferably formed in a layered or island shape in the interface region. As a forming method, while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material which is a light-emitting material or an electron injection material for forming an interface region is vapor-deposited at the same time. A method of dispersing at least one of a donor dopant and an organometallic complex reducing dopant is preferable. The dispersion concentration is organic substance: electron-donating dopant, organometallic complex = 100: 1 to 1: 100, preferably 5: 1 to 1: 5 in molar ratio.
When forming at least one of the electron donating dopant and the organometallic complex in a layered form, after forming the light emitting material or the electron injecting material as the organic layer at the interface in a layered form, at least one of the electron donating dopant and the organometallic complex is formed. These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
In the case where at least one of the electron donating dopant and the organometallic complex is formed in an island shape, after the light emitting material or the electron injecting material, which is the organic layer at the interface, is formed in an island shape, the electron donating dopant and the organometallic complex At least one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm to 1 nm.
In the organic EL device of the present invention, the ratio of the main component to at least one of the electron donating dopant and the organometallic complex is, as a molar ratio, the main component: the electron donating dopant, the organometallic complex = 5: 1 to 1. Is preferably up to 5, more preferably from 2: 1 to 1: 2.

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

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

[Second Embodiment]
In the second embodiment of the present invention, the compound contained in the hole transport layer is different from the above-described first embodiment, and the compound contained in the light-emitting layer has more types than the above-described first embodiment. The other points are the same as in the first embodiment.
In the second embodiment, the same materials, compounds, device configurations, and definitions as those described in the first embodiment can be applied unless otherwise specified.

(Compounds contained in the hole transport layer)
The hole transport layer of the organic EL device according to this embodiment contains a compound represented by the following general formula (30).

In the general formula (30), A ₁ and A ₂ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 5 ring atoms. 30 aromatic heterocyclic groups are represented.
Any two adjacent R ₄₁ to R ₄₄ are bonded to a partial structure represented by the following general formula (31). Any two adjacent R ₅₁ to R ₅₄ may be bonded to a partial structure represented by the following general formula (31).

R ₄₁ to R ₄₄ and R ₅₁ to R ₅₄ not bonded to the partial structure represented by the general formula (31) are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, substituted or unsubstituted. Amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, substituted Or an unsubstituted arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted Or an aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
p and q are 3.
L ₁ and L ₂ each independently represents a single bond or a divalent linking group.
In the general formula (31), * represents a binding site with the ring structure represented by the general formula (30).
One of Z ₁ and Z ₂ is a single bond, and the other is —O—, —S—, —CR ₆₅ R ₆₆ —, or —NR ₆₇ —. In the present embodiment, it is preferable that _one of Z ₁ and Z ₂ is a single bond, and the other is —O— or —CR ₆₅ R ₆₆ —. Alternatively, either _one of Z ₁ and Z ₂ is preferably a single bond, and the other is preferably —S— or —NR ₆₇ —.
R ₆₁ to R ₆₇ are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ˜40 trialkylsilyl group, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring formation It is a heterocyclic group having 5 to 50 atoms.

In this embodiment, the compound represented by the general formula (30) is preferably represented by the following general formula (32).

In the general formula (32), A ₁ , A ₂ , L ₁ , L ₂ , R ₄₁ to R ₄₅ , R ₅₁ to R ₅₅ , p, q, Z ₁ and Z ₂ , R ₆₁ to R ₆₇ are It is synonymous with the thing in General formula (30), (31).

In this embodiment, the compound represented by the general formula (30) is preferably represented by the following general formula (33) or the following general formula (34).

A ₁ , A ₂ , L ₁ , L ₂ , R ₄₁ to R ₄₅ , R ₅₁ to R ₅₅ , p, q, Z ₁ and Z ₂ , R _{61 in the} general formula (33) and the general formula (34) R ₆₇ is as defined in the general formulas (30) and (31).

The compound represented by the general formula (30) is preferably represented by any one of the following general formula (35), general formula (36), and general formula (37).

A ₁ , A ₂ , L ₁ , L ₂ , R ₄₁ to R ₄₅ , R ₅₁ to R ₅₅ , p, q, Z ₁ and Z ₂ , R ₆₁ to R _{67 in the} general formulas (35) to (37). Are synonymous with those in the general formulas (30) and (31), respectively.

In the present embodiment, it is preferable that Z ₁ in the general formulas (35) to (37) is —O— or —CR ₆₅ R ₆₆ —, and Z ₂ is a single bond.
Alternatively, in the present embodiment, it is preferable that Z ₁ in the general formulas (35) to (37) is a single bond, and Z ₂ is —O— or —CR ₆₅ R ₆₆ —.

In the present embodiment, it is preferable that Z ₁ in the general formulas (35) to (37) is —CR ₆₅ R ₆₆ — and Z ₂ is a single bond.

In the present embodiment, it is preferable that Z ₁ in the general formulas (35) to (37) is —S— or —NR ₆₇ —, and Z ₂ is a single bond.
Alternatively, it is preferable that Z ₁ in the general formulas (35) to (37) is a single bond, and Z ₂ is —S— or —NR ₆₇ —.

In the present embodiment, it is preferable that A ₁ and A ₂ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
In the present embodiment, when R ₅₁ to R ₅₄ are not bonded to the partial structure represented by the general formula (31), the A ₂ is preferably a substituted or unsubstituted phenyl group.

In the present embodiment, A ₂ is preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
In this embodiment, the A ₂ is more preferably a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 2-dibenzothiophenyl group, or a substituted or unsubstituted 4-dibenzothiophenyl group. More preferably.
In the present embodiment, A ₂ is more preferably a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted 2-dibenzofuranyl group, or a substituted or unsubstituted 4-dibenzofuranyl group. More preferably.

In the present embodiment, L ₂ is preferably a substituted or unsubstituted phenylene group, more preferably a substituted or unsubstituted m-phenylene group, or a substituted or unsubstituted p-phenylene group. It is more preferably a substituted or unsubstituted m-phenylene group.
In this embodiment, the A ₂ is a substituted or unsubstituted 2-dibenzothiophenyl group or a substituted or unsubstituted 4-dibenzothiophenyl group, and the L ₂ is a substituted or unsubstituted m-phenylene group. Or a substituted or unsubstituted p-phenylene group. More preferably, A ₂ is a substituted or unsubstituted 4-dibenzothiophenyl group, and L ₂ is a substituted or unsubstituted m-phenylene group.

In the present embodiment, L ₂ is preferably a single bond.
In the present embodiment, it is preferable that A ₂ is a substituted or unsubstituted 2-dibenzothiophenyl group or a substituted or unsubstituted 4-dibenzothiophenyl group, and L ₂ is a single bond. More preferably, A ₂ is a substituted or unsubstituted 4-dibenzothiophenyl group, and L ₂ is a single bond.

Examples of the compound contained in the hole transport layer of the present embodiment include the following compounds, but the present invention is not limited to this specific example.

(Light emitting layer)
The light emitting layer of the present embodiment includes a compound represented by the following general formula (2A) and a light emitting material.

In the general formula (2A), R ¹⁰¹ to R ¹⁰⁸ each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon group having 1 to 20 carbon atoms. An alkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, A substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.
Ar ¹⁰¹ and Ar ¹⁰¹ 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. .

The compound described in the first embodiment can also be used in the light emitting layer of the present embodiment.

In this embodiment, the host material is preferably a compound represented by the following general formula (3), the following general formula (4), or the following general formula (5).

In the general formula (3), Ar ¹¹¹ and Ar ¹¹² are each independently 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.
In the general formula (3), R ¹²¹ to R ¹³² each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon group having 1 to 20 carbon atoms. An alkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, A substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.

In the present embodiment, the Ar ¹¹¹ and the Ar ¹¹² in the general formula (3) are preferably naphthyl groups. In the general formula (3), the Ar ¹¹¹ and the Ar ¹¹² are 2-naphthyl groups, or the Ar ¹¹¹ is a 1-naphthyl group, and the Ar ¹¹² is a 2-naphthyl group. More preferred.

In the general formula (4), Ar ¹²¹ and Ar ¹²² each independently represent 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.
In the general formula (4), R ¹⁴¹ to R ¹⁵² each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon group having 1 to 20 carbon atoms. An alkyl group, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, A substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms.

In the general formula (5), Ar ¹³¹ is a substituted or unsubstituted phenyl group, Ar ¹³² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted group. The number of ring-forming atoms is 5-30.
R ¹⁶¹ to R ¹⁷² are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 A trialkylsilyl group of ˜40, or a substituted or unsubstituted arylsilyl group of 8 to 50 carbon atoms.

In the present embodiment, it is preferable that Ar ¹³¹ and Ar ¹³² in the general formula (5) are naphthyl groups. Further, the Ar ¹³¹ is a 2-naphthyl group and the Ar ¹³² is a 1-naphthyl group, or the Ar ¹³¹ is a 2-naphthyl group, and the Ar ¹³² is 1-naphthyl group. More preferably, it is a group.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the compound included in the light emitting layer of this embodiment include the aromatic hydrocarbon groups exemplified in the above embodiment. Among these, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted phenanthryl group are particularly preferable, and more specifically, a phenyl group, 2- A biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a 1-naphthyl group, a 2-naphthyl group, and a 9-phenanthryl group are preferable.

Examples of the heterocyclic group having 5 to 30 ring atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the aromatic heterocyclic groups exemplified in the above embodiment.

Examples of the alkyl group having 1 to 20 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the alkyl groups exemplified in the above embodiment.

The linear or branched alkyl group in the compound represented by the general formula (2A) contained in the light emitting layer of the present embodiment preferably has 1 to 10 carbon atoms, and preferably 1 to 6 carbon atoms. Further preferred. 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 Is preferred.

The number of ring-forming carbon atoms of the cycloalkyl group in the compound represented by the general formula (2A) contained in the light emitting layer of the present embodiment is preferably 3 to 10, and more preferably 5 to 8. Among the cycloalkyl groups, a cyclopentyl group and a cyclohexyl group are preferable.

Examples of the alkoxy group having 1 to 20 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the alkoxy groups exemplified in the above embodiment.

Examples of the aryloxy group having 6 to 30 ring carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the aryloxy groups exemplified in the above embodiment.

Examples of the arylthio group having 6 to 30 ring carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the arylthio groups exemplified in the above embodiment.

Examples of the trialkylsilyl group having 3 to 40 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of this embodiment include the trialkylsilyl groups exemplified in the above embodiment.

Examples of the arylsilyl group having 8 to 60 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. It is done.
Examples of the dialkylarylsilyl group having 8 to 50 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include, for example, the alkyl groups exemplified as the alkyl group having 1 to 20 carbon atoms. And a dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 20 ring carbon atoms. The carbon number of the dialkylarylsilyl group is preferably 8-30. The two alkyl groups in the dialkylarylsilyl group may be the same or different.
Examples of the alkyldiarylsilyl group having 13 to 50 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include, for example, the alkyl groups exemplified as the alkyl group having 1 to 20 carbon atoms. And an alkyldiarylsilyl group having two aromatic hydrocarbon groups having 6 to 20 ring carbon atoms. The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms. In the alkyldiarylsilyl group, the two aryl groups may be the same or different from each other.
Examples of the triarylsilyl group having 18 to 60 carbon atoms in the compound represented by the general formula (2A) included in the light emitting layer of the present embodiment include, for example, the aromatic hydrocarbon group having 6 to 30 ring carbon atoms. And a triarylsilyl group having three groups. The carbon number of the triarylsilyl group is preferably 18-30. In the triarylsilyl group, the three aromatic hydrocarbon groups may be the same or different.

Specific examples of the compound represented by the general formula (2A) contained in the light emitting layer of the present embodiment include the following compounds in addition to the compounds described in the first embodiment.

In the present embodiment, the light emitting material described in the first embodiment can be used as the light emitting material.

[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, at least one light emitting layer may be a combination of the compound contained in the hole transport layer described in the above embodiment and the compound contained in the light emitting layer. The light emitting layer may be a fluorescent light emitting layer or a phosphorescent light emitting layer.
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.

Other compounds described in the above embodiment can also be synthesized in accordance with the synthesis methods described in the following examples by using raw materials suitable for the compound to be synthesized.

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

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

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

In addition, for example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter abbreviated as NPD) having two condensed aromatic rings in the molecule, or

triphenylamine

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

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

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

[Synthesis Example]
(Synthesis of Compound 1)

Synthesis of intermediate 1-2 Under an argon atmosphere, 4-iodobromobenzene (28.3 g, 100.0 mmol), dibenzofuran-4-boronic acid (22.3 g, 105 mmol), tetrakis (triphenylphosphine) palladium ( 0) (2.31 g, 2.00 mmol) was added toluene (150 mL), dimethoxyethane (150 mL), and 2M aqueous sodium carbonate (150 mL), and the mixture was heated at reflux for 10 hours.
After completion of the reaction, the mixture was immediately filtered and the aqueous layer was removed. The organic layer was dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to obtain intermediate 1-2 (26.2 g, yield 81%).
According to the FD-MS analysis, the molecular weight 322 was m / e = 322.

Synthesis of Compound 1 In a three-necked flask under an argon atmosphere, Intermediate 1-2 (2.36 g, 7.3 mmol), Intermediate 1-1 (3.0 g, 7.3 mmol), CuI (1.4 g , 7.3 mmol), tripotassium phosphate (2.3 g, 11 mmol), anhydrous dioxane (30 mL) and cyclohexanediamine (0.84 g, 7.3 mmol) were added in this order, and the mixture was stirred at 100 ° C. for 8 hours. Water was added to the reaction solution to precipitate a solid, which was washed with hexane and then with methanol. Furthermore, the obtained solid was purified by silica gel column chromatography to obtain compound 1 (2.9 g, yield 60%).
As a result of FD-MS analysis, m / e = 650 with respect to the molecular weight of 650.

[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 the following compound (HI-1) is first formed so as to cover the transparent electrode on the surface where the ITO transparent electrode line is formed. ) Was deposited to form a 5 nm thick HI-1 film, and a hole injection layer was formed.
Next, on this HI-1 film, the following compound HT-1 was deposited as a first hole transporting material to form an HT-1 film having a thickness of 80 nm to form a first hole transporting layer.
Next, on this HT-1 film, the following compound HT-2 (compound 1 obtained in Synthesis Example 1) is deposited to form a 15 nm-thick HT-2 film, and the second hole transport A layer was formed.
Further, Compound BH-1 was vapor-deposited on this HT-2 film to form a light emitting layer having a thickness of 25 nm. At the same time, the following compound (BD1) was co-deposited as a fluorescent material. The concentration of Compound BD1 was 5.0% by mass. This co-deposited film functions as a light emitting layer.
Then, on this light emitting layer, the following compound ET-1 was deposited to form an ET-1 film having a thickness of 20 nm to form a first electron transport layer.
Next, the following compound ET-2 was vapor-deposited on this ET-1 film to form an ET-2 film having a thickness of 5 nm, thereby forming a second electron transport layer.
Next, LiF was deposited on the ET-2 film at a deposition rate of 0.1 angstrom / min to form a 1-nm-thick LiF film to form an electron injecting electrode (cathode).
And metal Al was vapor-deposited on this LiF film | membrane, the metal Al film | membrane with a film thickness of 80 nm was formed into a film, and the metal Al cathode was formed.

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

Examples 2 to 3
The organic EL devices of Examples 2 to 3 were produced in the same manner as in Example 1 except that the compounds in the second hole transport layer and the light emitting layer in Example 1 were changed to the compounds shown in Table 1. .

Comparative examples 1 to 3
In the organic EL elements of Comparative Examples 1 to 3, except that at least one of the compound HT-2 of the second hole transport layer and the compound BH-1 of the light emitting layer in Example 1 was changed to the compounds shown in Table 1. Was prepared in the same manner as in Example 1.

[Evaluation of organic EL elements]
About the produced organic EL element, brightness | luminance (unit: cd / m < ² >), CIE1931 chromaticity, current efficiency L / J, external quantum efficiency EQE, main peak wavelength (lambda) _p , and lifetime were evaluated. Table 2 shows the results when the current density is 1.00 mA / cm ² for each evaluation item. The values of brightness, current efficiency L / J, external quantum efficiency EQE, and lifetime shown in Table 2 are the evaluation items of Examples 1 to 3 and Comparative Examples 1 to 3 with respect to the values of the evaluation items of Comparative Example 1. This is a value obtained by calculating the ratio of the values.

-CIE1931 chromaticity CIE1931 chromaticity coordinates (x, y) when a voltage is applied to the element so that the current density is 1.00 mA / cm ² are measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta). did.

・ Current efficiency L / J
The spectral radiance spectrum when a voltage is applied to the device so that the current density is 1.00 mA / cm ² is measured by the spectral radiance meter, and the current efficiency (unit: cd) is obtained from the obtained spectral radiance spectrum. / A) was calculated.

・ Main peak wavelength λ _p
The main peak wavelength λ _p (unit: nm) was determined from the obtained spectral radiance spectrum.

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

・ Lifetime LT80
A voltage was applied to the device so that the current density was 50.00 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, it was found that the organic EL element of Example 1 was higher in luminous efficiency and longer in life than the organic EL elements of Comparative Examples 1 to 3. For example, the organic EL element of Example 1 has an external quantum efficiency EQE of 2.3 times, a lifetime LT80 of 1.3 times, a high luminous efficiency, and a long lifetime compared to the organic EL element of Comparative Example 1. It turns out that.
Further, as shown in Table 2, it was found that the organic EL elements of Examples 2 and 3 were higher in luminous efficiency and longer in life than the organic EL elements of Comparative Examples 1 to 3. .

The organic EL element of the present invention has high luminous efficiency and can be used for electronic devices such as lighting devices and display devices as long-life organic EL elements.

DESCRIPTION OF SYMBOLS 1 ... Organic electroluminescent element 2 ... Substrate 3 ... Anode 4 ... Cathode 5 ... Phosphorescent light emitting layer 6 ... Hole injection / transport layer 7 ... Electron injection / transport layer 10 ... Organic thin film layer

Claims

The anode,
A cathode provided opposite to the anode;
An organic layer provided between the anode and the cathode,
The organic layer includes a hole transport layer and a light emitting layer in this order from the anode side,
The hole transport layer includes a compound represented by the following general formula (1),
The said light emitting layer contains either a luminescent material, the compound represented by following General formula (10), and the compound represented by following General formula (11), The organic electroluminescent element characterized by the above-mentioned.

(In the general formula (1), A 1 and A 2 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted ring carbon 2 Represents 30 to 30 aromatic heterocyclic groups.
Y 1 to Y 16 each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
L 1 and L 2 each independently represent a single bond or a divalent linking group.
However, at least one of A 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted Benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, substituted or unsubstituted benzo [b ] Fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted carbazolyl Group, substituted or unsubstituted phenanthrenyl group, It represents a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted binaphthyl group.
When Y 1 to Y 16 are all C (R), Y 6 and Y 11 are bonded by a single bond, L 1 and L 2 are a single bond, and A 1 is a phenanthrenyl group, A 2 Is not a phenanthrenyl group.
Furthermore, when Y 1 to Y 16 are all C (R), Y 6 and Y 11 are bonded by a single bond, and L 1 and L 2 are a single bond, R is not a fluorenyl group. In addition, when A 1 is a fluorenyl group, A 2 is not a phenyl group, a naphthyl group, or a fluorenyl group. )

(In the general formula (10) and the general formula (11), R 101 to R 108 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted group. Substituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, substituted or unsubstituted ring forming carbon atoms An arylthio group having 6 to 20 carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms,
Ar 31 to Ar 33 , R 109 , R 110 , and R 21 to R 28 each independently represent a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, or a substituted or unsubstituted carbon number. An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring carbon number having 6 to 20 carbon atoms Arylthio group, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms It is a hydrocarbon group or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and adjacent R 21 to R 28 may form a ring.
However, at least one of Ar 31 to Ar 33 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
In the general formula (10) and the general formula (11), when Ar 31 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, Ar 31 is substituted or unsubstituted. Substituted fluorenyl group.
In the general formula (11), when Ar 31 , Ar 33 , R 109 , and R 110 are hydrogen atoms, Ar 32 is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 30 ring carbon atoms. is there. )
2. The organic electroluminescence device according to claim 1, wherein in the general formula (1), at least one of A 1 and A 2 is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or Unsubstituted benzophenanthrenyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or An unsubstituted picenyl group, a substituted or unsubstituted benzo [b] fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted benzothiophenyl group, substituted or Unsubstituted dibenzothiophenyl group, substituted Ku unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group organic electroluminescent device, characterized in that, or a substituted or unsubstituted binaphthyl group.
3. The organic electroluminescence device according to claim 1, wherein in the general formula (1), at least one of A 1 and A 2 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzo. An organic electroluminescence device characterized by being a thiophenyl group or a substituted or unsubstituted carbazolyl group.
4. The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) contained in the hole transport layer is represented by the following general formula (1-2): An organic electroluminescence device represented by the formula:
4. The organic electroluminescence device according to claim 1, wherein the compound represented by the general formula (1) contained in the hole transport layer is represented by the following general formula (1-3): Or an organic electroluminescence device represented by the following general formula (1-4).
The organic electroluminescence device according to any one of claims 1 to 5, represented by L 1 -A 1 of the compound represented by the general formula (1) contained in the hole transport layer. And the structure of the portion represented by L 2 -A 2 are different from each other.
The organic electroluminescent element according to any one of claims 1 to 6, wherein the light-emitting layer includes a compound represented by the general formula (11), and Ar 31 , Ar 33 , R 109 , And when R 110 is a hydrogen atom, Ar 32 is a substituted or unsubstituted naphthyl group.
The organic electroluminescent element according to any one of claims 1 to 6, wherein Ar 31 is a substituted or unsubstituted ring-forming carbon number in the general formula (10) and the general formula (11). An organic electroluminescence device characterized by being represented by the following general formula (12) and the following general formula (13) when it becomes a 6-30 aromatic hydrocarbon group.

(In the general formula (12) and the general formula (13),
R 31 and R 32 are each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, and R 33 to R 37 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, Substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 20 ring carbon atoms An oxy group, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, m is It is. )
The anode,
A cathode provided opposite to the anode;
An organic layer provided between the anode and the cathode,
The organic layer includes a hole transport layer and a light emitting layer in this order from the anode side,
The hole transport layer includes a compound represented by the following general formula (30), and the light emitting layer includes a compound represented by the following general formula (2A) and a light emitting material. Luminescence element.

(In the general formula (30), A 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5; Represents 30 to 30 aromatic heterocyclic groups.
Any two adjacent R 41 to R 44 are bonded to a partial structure represented by the following general formula (31). Any two adjacent R 51 to R 54 may be bonded to a partial structure represented by the following general formula (31). )

(R 41 to R 44 and R 51 to R 54 not bonded to the partial structure represented by the general formula (31) are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted A substituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, Substituted or unsubstituted arylthio group having 6 to 20 carbon atoms, substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted A substituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
p and q are 3,
L 1 and L 2 each independently represents a single bond or a divalent linking group.
In the general formula (31), * represents a bonding site with the ring structure represented by the general formula (30),
One of Z 1 and Z 2 is a single bond, and the other is —O—, —S—, —CR 65 R 66 —, or —NR 67 —;
R 61 to R 67 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 ˜40 trialkylsilyl group, substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or substituted or unsubstituted ring formation It is a heterocyclic group having 5 to 50 atoms. ))

(In the general formula (2A), R 101 to R 108 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted carbon number of 1 to 20 Alkyl groups, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 20 ring carbon atoms, and substituted or unsubstituted arylthio groups having 6 to 20 ring carbon atoms. A substituted or unsubstituted trialkylsilyl group having 3 to 40 carbon atoms, or a substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms,
Ar 1001 and Ar 101 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. . Ar 100 may form a ring with R 101 or R 108, and Ar 101 may form a ring with R 104 or R 105 . )
The organic electroluminescence device according to claim 9, wherein the compound represented by the general formula (30) is represented by the following general formula (32).

(In the general formula (32), A 1 , A 2 , L 1 , L 2 , R 41 to R 45 , R 51 to R 55 , p, q, Z 1 and Z 2 , R 61 to R 67 are respectively (It has the same meaning as in the general formulas (30) and (31).)
The organic electroluminescence device according to claim 9, wherein the compound represented by the general formula (30) is represented by the following general formula (33) or the following general formula (34). element.

(A 1 , A 2 , L 1 , L 2 , R 41 to R 45 , R 51 to R 55 , p, q, Z 1 and Z 2 , R in the general formula (33) and the general formula (34) 61 to R 67 have the same meanings as in the general formulas (30) and (31), respectively.
The organic electroluminescence device according to any one of claims 9 to 11, wherein any one of Z 1 and Z 2 in the general formula (31) is a single bond, and the other is -O-, or -CR 65 R 66 - organic electroluminescent device which is a.
12. The organic electroluminescence device according to claim 9, wherein one of Z 1 and Z 2 is a single bond, and the other is —S— or —NR 67 —. An organic electroluminescence device characterized in that there is.
The organic electroluminescence device according to claim 9, wherein the compound represented by the general formula (30) is represented by any one of the following general formula (35), general formula (36), and general formula (37). An organic electroluminescence device characterized by that.

(A 1 , A 2 , L 1 , L 2 , R 41 to R 45 , R 51 to R 55 , p, q, Z 1 and Z 2 , R 61 to R in the general formulas (35) to (37)) 67 is synonymous with that in the general formulas (30) and (31).)
15. The organic electroluminescence device according to claim 14, wherein Z 1 in the general formulas (35) to (37) is —O— or —CR 65 R 66 —, and Z 2 is a single bond. An organic electroluminescence element.
15. The organic electroluminescence device according to claim 14, wherein Z 1 in the general formulas (35) to (37) is a single bond, and Z 2 is —O— or —CR 65 R 66 —. An organic electroluminescence element.
15. The organic electroluminescence device according to claim 14, wherein Z 1 in the general formulas (35) to (37) is —CR 65 R 66 —, and Z 2 is a single bond. element.
15. The organic electroluminescence device according to claim 14, wherein Z 1 in the general formulas (35) to (37) is —S— or —NR 67 —, and Z 2 is a single bond. Organic electroluminescence device.
15. The organic electroluminescence device according to claim 14, wherein Z 1 in the general formulas (35) to (37) is a single bond, and Z 2 is —S— or —NR 67 —. Organic electroluminescence device.
The organic electroluminescence device according to any one of claims 9 to 19, wherein A 1 and A 2 are each independently substituted or unsubstituted aromatic carbon atoms having 6 to 30 ring carbon atoms. An organic electroluminescence element characterized by being a hydrogen group.
The organic electroluminescence device according to any one of claims 9 to 19, wherein A 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted group. An organic electroluminescence device characterized by being a dibenzothiophenyl group.
The organic electroluminescence device according to claim 21, wherein the A 2 is a substituted or unsubstituted dibenzothiophenyl group.
23. The organic electroluminescence device according to claim 22, wherein the A 2 is a substituted or unsubstituted 2-dibenzothiophenyl group or a substituted or unsubstituted 4-dibenzothiophenyl group. Luminescence element.
The organic electroluminescent element according to claim 21, wherein the A 2 is a substituted or unsubstituted dibenzofuranyl group.
25. The organic electroluminescence device according to claim 24, wherein the A 2 is a substituted or unsubstituted 2-dibenzofuranyl group, or a substituted or unsubstituted 4-dibenzofuranyl group. Luminescence element.
The organic electroluminescent element according to any one of claims 9 to 25, wherein the L 2 is a substituted or unsubstituted phenylene group.
27. The organic electroluminescence device according to claim 26, wherein the L 2 is a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted p-phenylene group.
27. The organic electroluminescence device according to claim 26, wherein the L 2 is a substituted or unsubstituted m-phenylene group.
The organic electroluminescent element according to any one of claims 9 to 25, wherein the L 2 is a single bond.
The organic electroluminescence device according to any one of claims 9 to 29, wherein the compound represented by the general formula (2A) is represented by the following general formula (2). Organic electroluminescence device.

(In the general formula (2), any one of R 109 to R 113 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, and other R 109 to R 113 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted ring carbon number. 6-20 arylthio groups, substituted or unsubstituted trialkylsilyl groups having 3 to 40 carbon atoms, substituted or unsubstituted arylsilyl groups having 8 to 50 carbon atoms, substituted or unsubstituted Ring aromatic hydrocarbon group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group ring atoms 5-50,
Ar 101 and R 101 to R 108 have the same meanings as those in the general formula (2A). )
31. The organic electroluminescence device according to claim 30, wherein the compound represented by the general formula (2) is represented by the following general formula (3).

(In the general formula (3), Ar 111 and Ar 112 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted number of ring atoms. 5-30 heterocyclic groups,
R 121 to R 132 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 A trialkylsilyl group of ˜40, or a substituted or unsubstituted arylsilyl group of 8 to 50 carbon atoms. )
32. The organic electroluminescence device according to claim 31, wherein the Ar 111 and the Ar 112 are naphthyl groups.
33. The organic electroluminescence device according to claim 32, wherein the Ar 111 and the Ar 112 are 2-naphthyl groups.
33. The organic electroluminescent device according to claim 32, wherein the Ar 111 is a 1-naphthyl group and the Ar 112 is a 2-naphthyl group.
31. The organic electroluminescence device according to claim 30, wherein the compound represented by the general formula (2) is represented by the following general formula (4).

(In the general formula (4), Ar 121 and Ar 122 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted number of ring forming atoms. 5-30 heterocyclic groups,
R 141 to R 152 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted amino group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group. An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 A trialkylsilyl group of ˜40, or a substituted or unsubstituted arylsilyl group of 8 to 50 carbon atoms. )
31. The organic electroluminescence device according to claim 30, wherein the compound represented by the general formula (2) is represented by the following general formula (5).

(In the general formula (5), Ar 131 is a substituted or unsubstituted phenyl group, Ar 132 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted group. A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
R 161 to R 172 are each independently a hydrogen atom, halogen atom, hydroxyl group, cyano group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 20 ring carbon atoms, a substituted or unsubstituted arylthio group having 6 to 20 ring carbon atoms, a substituted or unsubstituted carbon number of 3 A trialkylsilyl group of ˜40, or a substituted or unsubstituted arylsilyl group of 8 to 50 carbon atoms. )
37. The organic electroluminescence device according to claim 36, wherein the Ar 131 and the Ar 132 are naphthyl groups.
38. The organic electroluminescence device according to claim 37, wherein the Ar 131 is a 2-naphthyl group, and the Ar 132 is a 1-naphthyl group.
39. The organic electroluminescence device according to claim 38, wherein the Ar 131 is a 2-naphthyl group, and the Ar 132 is a 1-naphthyl group.
An electronic apparatus comprising the organic electroluminescence element according to any one of claims 1 to 39.