JP2015065248A - Organic electroluminescent element, and electronic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide: an organic EL element which is driven by a low voltage, and has a high light emission efficiency and a long life, and which can be mass-produced with stability at low cost; and an electronic device having such an organic EL element.SOLUTION: An organic EL element comprises: an anode; a light-emitting layer; a hole transport layer provided to be adjacent to the light-emitting layer between the anode and the light-emitting layer; and a hole injection layer provided between the anode and the hole transport layer. The hole transport layer and the hole injection layer are adjacent to each other. The hole transport layer includes a compound expressed by the general formula (1) below. The hole injection layer includes a condensed compound formed by the condensation of two to three structures each expressed by the general formula (2a) below to a first ring structure selected from a substituted or unsubstituted aromatic hydrocarbon group, of which the number of carbon atoms forming a ring is 6-24, and a substituted or unsubstituted heterocyclic group, of which the number of carbon atoms forming a ring 6-24.

Description

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

  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.
In order to meet the demand for low voltage drive and high efficiency, organic layers are stacked so that the ionization potential is on the staircase, and materials adjacent to the light-emitting layer have high ionization potential and low electron affinity. Organic EL devices in which conventional layers are stacked have been designed. As such an organic EL element, an organic EL element in which a hole injection layer, a hole transport layer, and an electron block layer are laminated in this order from the anode side between the anode and the light emitting layer is known.

For example, in Patent Document 1, a hole injection layer, a first hole transport layer, and a second hole transport layer are sequentially stacked between an anode and a light emitting layer, and a second hole transport layer adjacent to the light emitting layer is formed. That is, an organic EL device having high emission efficiency using a layer made of a biscarbazole derivative having a large ionization potential and a small electron affinity as an electron blocking layer is disclosed. In this organic EL element, the first hole transport layer reduces the energy barrier necessary for hole injection in a series of hole injection processes from the anode to the electron blocking layer, and contributes to low voltage driving of the organic EL element. doing.
In addition, HAT-CN6 (1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile) has been generally used as a material for forming a hole injection layer of an organic EL element. . As other materials, indenofluorangeone derivatives described in Patent Documents 2 to 4 are also known.

International Publication No. 2012/108389 International Publication No. 2009/069717 International Publication No. 2009/011327 International Publication No. 2010/064655

  However, in recent years, in organic EL elements, in addition to low voltage driving and high efficiency, cost reduction and mass productivity improvement at the time of manufacture are desired, and it is required to reduce the number of layers of organic EL elements. ing.

  An object of the present invention is to provide an organic electroluminescence element that can be driven at a low voltage, has high luminous efficiency and long life, and can be stably mass-produced at low cost, and an electronic apparatus including the organic electroluminescence element. It is.

  First, in order to reduce the number of layers of the organic EL element, the present inventors omit the first hole transport layer from the organic EL element described in Patent Document 1, and provide a biscarbazole derivative that is the second hole transport layer. As a sole hole transport layer, the layer consisting of was laminated adjacent to the hole injection layer containing HAT-CN6. In this case, as described above, the energy barrier necessary for injecting holes into the hole transport layer having a large ionization potential is large, and the organic EL device is increased in voltage, so that practical device performance cannot be obtained. As a result of further research, the inventors of the present invention, unlike the conventional case, use a material with a high electron affinity for the hole injection layer and a material with a high ionization potential for the hole transport layer. As a result, the present inventors have found that the device performance can be maintained while reducing the thickness of the device, thereby completing the present invention.

An organic electroluminescence device according to an embodiment of the present invention is
The anode,
A cathode provided opposite to the anode;
A light emitting layer provided between the anode and the cathode;
A hole transport layer provided adjacent to the light emitting layer between the anode and the light emitting layer;
A hole injection layer provided between the anode and the hole transport layer,
The hole transport layer and the hole injection layer are adjacent,
The hole transport layer includes a compound represented by the following general formula (1),
The hole injection layer is a first ring selected from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 6 to 24 ring atoms. The structure includes a condensed compound formed by condensing 2 or more and 3 or less structures represented by the following general formula (2a).

(In the general formula (1),
A ¹ and A ² are independent of each other
It represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹ , L ² and L ³ are each independently a single bond or a divalent linking group,
As the linking group in L ¹ , L ² and L ³ ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
The aromatic hydrocarbon group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may form a ring when adjacent groups are bonded to each other or may not form a ring. .
Y ^{1 to} Y ¹⁶ each independently represent C (R) or a nitrogen atom,
Each R is independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
It is.
However, one of Y ^{5 to} Y ⁸ and one of Y ^{9 to} Y ¹² are carbon atoms bonded to L ³ .
One or more sets of Y ¹ and Y ² , Y ² and Y ³ , Y ³ and Y ⁴ , Y ¹³ and Y ¹⁴ , Y ¹⁴ and Y ¹⁵ , and Y ¹⁵ and Y ¹⁶ are represented by the following general formula (1a ) May bond to a carbon atom. )

(In the general formula (1a),
Each * is any of Y ¹ and Y ² , Y ² and Y ³ , Y ³ and Y ⁴ , Y ¹³ and Y ¹⁴ , Y ¹⁴ and Y ¹⁵ , and Y ¹⁵ and Y ^{16 in} the general formula (1). Or a bond position to a set of carbon atoms.
X ¹ is an oxygen atom, a sulfur atom, CR ⁵ R ⁶ , or NR ⁷ .
R ^{1 to} R ⁷ have the same meaning as R in the general formula (1). )

(In the general formula (2a),
a is a ring structure condensed to the first ring structure, and is represented by the following general formula (2b).
X ²¹ and X ²² are each independently C (R) or a nitrogen atom.
R ²¹ and R ²² are independently the same as R in the general formula (1). )

(In the general formula ^{(2b), X 20} is represented by any one of the following formulas (2b-1) ~ (2b -12).)

(In the general formulas (2b-1) to (2b-12), R ²⁰ has the same meaning as R in the general formula (1).)

In addition, the organic EL element according to an embodiment of the present invention is
The anode,
A cathode provided opposite to the anode;
A light emitting layer provided between the anode and the cathode;
A hole transport layer provided between the anode and the light emitting layer;
A hole injection layer provided between the anode and the hole transport layer,
The hole transport layer and the hole injection layer are adjacent,
The hole injection layer has an electron affinity (Af) of 4.8 eV to 5.8 eV.

  According to the present invention, it is possible to provide an organic EL element that can be driven at a low voltage, has high luminous efficiency and long life, and can be mass-produced stably at low cost, and an electronic device including the organic EL element. .

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

[Organic EL device]
The organic EL device according to the first embodiment of the present invention includes a cathode, an anode, and an organic layer disposed between the cathode and the anode.
In the organic EL device of the present invention, the organic layer includes at least a hole injection layer, a hole transport layer, and a light emitting layer. In addition to these layers, a layer employed in a known organic EL device such as an electron injection layer, an electron transport layer, and a hole barrier layer may be further provided between the light emitting layer and the cathode. The organic layer may contain an inorganic compound.

As typical element configurations of the organic EL element in the present embodiment, for example, the following configurations (a) to (e) can be given.
(A) Anode / hole injection layer / hole transport layer / light emitting layer / cathode (b) Anode / hole injection layer / hole transport layer / light emitting layer / electron injection / transport layer / cathode (c) Anode / positive Hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (d) Anode / hole injection layer / hole transport layer / light emitting layer / barrier layer / electron injection / transport layer / cathode e) Anode / hole injection layer / hole transport layer / light emitting layer / barrier layer / electron transport layer / electron injection layer / cathode Among the above, the configuration of (d) is preferably used, but of course, it is limited to these. It is not a thing.
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 “electron injection / transport layer” means “at least one of an electron injection layer and an electron transport layer”. Moreover, when it has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided in the cathode side.
As for the organic layer in the electron transport region existing between the light emitting layer and the cathode, all of the layers exhibit electron transport properties, but in general, the barrier layer serves to prevent the diffusion of excitation energy, and the electron injection layer. Serves to reduce the electron injection barrier.

The above light-emitting layer is a laminate in which a plurality of light-emitting layers are stacked, so that electrons and holes are accumulated at the light-emitting layer interface, and the recombination region is concentrated at the light-emitting layer interface to improve quantum efficiency. Can do.
The ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.

In FIG. 1, schematic structure of an example of the organic EL element in this embodiment is shown.
An organic EL element 1 shown in FIG. 1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
The organic layer 10 includes a hole injection layer 7, a hole transport layer 5, a light emitting layer 6, and an electron injection / transport layer 8 in this order from the anode 3 side. The hole transport layer 5 is adjacent, and the hole transport layer 5 and the light emitting layer 6 are adjacent.

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

(In the general formula (1),
A ¹ and A ² are independent of each other
It represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹ , L ² and L ³ are each independently a single bond or a divalent linking group,
As the linking group in L ¹ , L ² and L ³ ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
The aromatic hydrocarbon group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may form a ring when adjacent groups are bonded to each other or may not form a ring. .
Y ^{1 to} Y ¹⁶ each independently represent C (R) or a nitrogen atom,
Each R is independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
It 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.
However, one of Y ^{5 to} Y ⁸ and one of Y ^{9 to} Y ¹² are carbon atoms bonded to L ³ .
One or more sets of Y ¹ and Y ² , Y ² and Y ³ , Y ³ and Y ⁴ , Y ¹³ and Y ¹⁴ , Y ¹⁴ and Y ¹⁵ , and Y ¹⁵ and Y ¹⁶ are represented by the following general formula (1a ) May bond to a carbon atom. )

(In the general formula (1a),
Each * is any of Y ¹ and Y ² , Y ² and Y ³ , Y ³ and Y ⁴ , Y ¹³ and Y ¹⁴ , Y ¹⁴ and Y ¹⁵ , and Y ¹⁵ and Y ^{16 in} the general formula (1). Or a bond position to a set of carbon atoms.
X ¹ is an oxygen atom, a sulfur atom, CR ⁵ R ⁶ , or NR ⁷ .
R ^{1 to} R ⁷ have the same meaning as R in the general formula (1). )

  The compound represented by the general formula (1) is preferably represented by either the following general formula (1-1) or (1-2).

(In the general formulas (1-1) and (1-2), A ¹ , A ² , L ¹ , L ² , L ³ , Y ^{1 to} Y ¹⁶ are respectively A ¹ in the general formula (1). , A ² , L ¹ , L ² , L ³ , Y ^{1 to} Y ¹⁶ .

  The compound represented by the general formula (1) is preferably represented by any one of the following general formulas (1-A) to (1-G).

(In the general formulas (1-A) to (1-G), A ¹ , A ² , L ¹ , L ² , L ³ are respectively A ¹ , A ² , L ¹ in the general formula (1). , L ² and L ³ .
X ¹ has the same meaning as ^{X 1} in the general formula (1a).
Z ^{11 to} Z ¹⁸ are carbon atoms, one of Z ^{11 to} Z ¹⁴ , and one of Z ^{15 to} Z ¹⁸ are carbon atoms bonded to L ³ .
Several R < ¹¹ > -R < ¹⁵ > is synonymous with R in the said General formula (1) each independently.
p is 4, q is 2, n is 4, s is 3, and t is 3. )

L ³ in the general formulas (1-A) to (1-G) is a bond that bonds Z ¹³ and Z ¹⁷ , a bond that bonds Z ¹³ and Z ¹⁶ , or Z ¹² and Z ^17. Is preferably a bond that bonds Z ¹³ and Z ¹⁶ , or a bond that bonds Z ¹² and Z ¹⁷ .

Further, L ³ is more preferably a single bond.

In the general formulas (1), (1-1), (1-2), and (1-A) to (1-G), at least one of A ¹ and A ² is a substituted or unsubstituted ring-forming carbon. It is preferably a C10-24 aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group having 9-24 ring atoms.

Further, in the general formulas (1), (1-1), (1-2) and (1-A) to (1-G), at least one of A ¹ and A ² is a substituted or unsubstituted full Oranthenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted benzophenanthrenyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted A chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, a substituted or unsubstituted benzo [b] fluoranthenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted dibenzofuranyl Group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted dibenzothiophenyl group, Or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, or preferably represents a substituted or unsubstituted binaphthyl group.
More preferably, at least one of A ¹ and A ² is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group. Represents.

In the general formulas (1), (1-1), (1-2), and (1-A) to (1-G), a partial structure represented by L ¹ -A ¹ and L ² — The partial structures represented by A ² are preferably different from each other.
L ¹ and L ² are preferably each independently a single bond or a phenylene group.

  Next, each substituent described in the general formulas (1), (1a), (1-1), (1-2) and (1-A) to (1-G) will be described.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, Fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrycenyl group, benzo [b] triphenylenyl group, picenyl group, perylenyl group Etc.
As an aromatic hydrocarbon group in this embodiment, it is preferable that ring forming carbon number is 6-20, and it is still more preferable that it is 6-12. Of the aromatic hydrocarbon groups, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable. For the 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group, the 9-position carbon atom is substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the present embodiment described later. It is preferable that
In addition, as the aromatic hydrocarbon group having 6 to 24 ring carbon atoms in the first ring structure of the present embodiment, a group having 6 to 24 ring carbon atoms among the aromatic hydrocarbon groups described above is used. be able to.

Examples of the heterocyclic group having 5 to 30 ring atoms in the present embodiment include a pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl, benzoxazolyl Group, benzothiazolyl group, benzisoxazolyl group, benzoisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothiophenyl group, piperidinyl group, pyrrolidinyl group, piperazinyl group, morpholyl Group, phenazinyl group, phenothiazinyl group, phenoxazinyl group and the like.
The number of ring-forming atoms of the heterocyclic group in the present embodiment is preferably 5-20, and more preferably 5-14. Among the above heterocyclic groups, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, 4-dibenzothiophenyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group are particularly preferable. As for the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the substituted or unsubstituted aromatic hydrocarbon having 6 to 30 ring carbon atoms in the present embodiment is attached to the 9th-position nitrogen atom. The group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.
In addition, as the heterocyclic group having 6 to 24 ring atoms in the first ring structure of the present embodiment, a group having 6 to 24 ring atoms among the above-described heterocyclic groups can be used.

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

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

Examples of the arylsilyl group having 6 to 60 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
The dialkylarylsilyl group has, for example, two alkyl groups exemplified as the alkyl group having 1 to 30 carbon atoms, and one dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 30 ring carbon atoms. Is mentioned. The carbon number of the dialkylarylsilyl group is preferably 8-30.
The alkyldiarylsilyl group has, for example, one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms, and two alkyldiarylsilyl groups having the two aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. Is mentioned. The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
Examples of the triarylsilyl group include a triarylsilyl group having three aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30.

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

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

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

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

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

  As a halogen atom in this embodiment, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, Preferably it is a fluorine atom.

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

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

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

(Hole injection layer)
The hole injection layer 7 is adjacent to the hole transport layer 5 on the anode 3 side of the hole transport layer 5, and is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms and a substituted or unsubstituted group. A condensed compound formed by condensing 2 or more and 3 or less of the structure represented by the following general formula (2a) to the first ring structure selected from the heterocyclic groups having 6 to 24 ring atoms of .

(In the general formula (2a),
a is a ring structure condensed to the first ring structure, and is represented by the following general formula (2b).
X ²¹ and X ²² are each independently C (R) or a nitrogen atom.
R ²¹ and R ²² are independently the same as R in the general formula (1). )

(In the general formula ^{(2b), X 20} is represented by any one of the following formulas (2b-1) ~ (2b -12).)

(In the general formulas (2b-1) to (2b-12), R ²⁰ has the same meaning as R in the general formula (1).)

Incidentally, the general formula (2b), for ^example, if ^{X 20} is the general formula (2b-1), the structure below.

  The condensation compound is preferably represented by the following general formula (2-1) or (2-2).

(In the general formulas (2-1) and (2-2),
Ar ²¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 6 to 24 ring atoms,
a ^{21 to} a ²³ are each independently synonymous with a in the general formula (2a).
X ^{23 to} X ²⁸ are independently the same as X ²¹ and X ²² in the general formula (2a).
R ^{23 to} R ²⁸ are each independently synonymous with R ²¹ and R ²² in the general formula (2a). )

In the general formulas (2-1) and (2-2), Ar ²¹ is a substituted or unsubstituted benzene ring, or a substituted or unsubstituted heterocyclic group having 6 ring-forming atoms. Is preferred.
That is, the general formula (2-1) is represented by the following general formula (2-1-1), and the general formula (2-2) is represented by the following general formula (2-2-1). It is preferable.

(In the general formulas (2-1-1) and (2-2-1),
a ^{21 to} a ²³ are each independently synonymous with a in the general formula (2a).
X ^{23 to} X ²⁸ are independently the same as X ²¹ and X ²² in the general formula (2a).
R ^{23 to} R ²⁸ are each independently synonymous with R ²¹ and R ²² in the general formula (2a).
In the general formula (2-1-1),
Z ²¹ and Z ²² are each independently CH or a nitrogen atom. )

In the general formula (2b), X ²⁰ is preferably represented by the general formula (2b-1).
The dicyanomethylene group represented by the general formula (2b-1) has strong electron withdrawing property and low molecular symmetry, and therefore increases the dipole moment in the molecule. As a result, the molecule has a large electron affinity and can be suitably used as a material for the hole injection layer of the present embodiment.

Moreover, it is preferable that at least one of R ²¹ and R ²² in the general formula (2a) is a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group.
The condensation compound is more preferably represented by the following general formulas (2-F) to (2-J).

(In the general formulas (2-F) to (2-J), A ²⁰¹ represents a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group.)

In the general formula (2a), at least one of R ²¹ and R ²² is a substituted ring having at least one group selected from a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group as a substituent. An aromatic hydrocarbon group having 6 to 24 carbon atoms or a substituted heterocyclic group having 6 to 24 ring atoms is also preferable.

  The condensation compound is particularly preferably represented by any one of the following general formulas (2-A) to (2-E).

(In General Formulas (2-A) to (2-E), Ar ²⁰¹ is a substituted ring-forming carbon number having at least one group selected from a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group. 6 to 24 aromatic hydrocarbon groups or substituted heterocyclic groups having 6 to 24 ring atoms.)

  In the condensed compound, the structures represented by the general formula (2a) are preferably the same.

  The general formulas (2a), (2b), (2b-1) to (2b-12), (2-1), (2-2), (2-1-1), (2-2-1) And the substituents described in (2-A) to (2-E) have the general formulas (1), (1a), (1-1), (1-2), and (1-A) to This is the same as described in (1-G).

  Specific examples of the condensation compound contained in the hole injection layer 7 are shown below, but the present invention is not limited to these exemplified compounds.

(Relationship between hole injection layer and hole transport layer)
In the present embodiment, by using the compound represented by the general formula (1) for the hole transport layer and using the specific condensation compound described above for the hole injection layer, the hole injection property from the anode to the light emitting layer is achieved. Can be raised.
Conventionally, in order to increase the efficiency of an organic EL element, an electron block layer for an electron block and an exciton block has been provided between the hole transport layer and the light emitting layer. In order to increase the exciton blocking effect, it is necessary to use a compound having a large singlet and triplet excitation energy for the material used for the electron blocking layer, and the ionization potential (Ip) of the material tends to increase. As a result, the hole injection barrier from the conventional hole injection layer having a relatively low electron affinity (Af) to the electron blocking layer is increased, and the energy barrier is reduced between the hole injection layer and the electron blocking layer. It was necessary to separately form a hole transport layer having a relatively small Ip.
However, the hole injection layer of this embodiment can easily inject holes into a conventional electron block layer having a relatively large Ip by using a material having a large electron affinity (Af). Therefore, the electron blocking layer can also serve as a hole transporting layer, and the performance of the organic EL element (low voltage driving, without providing the hole transporting layer conventionally provided between the hole injection layer and the electron blocking layer) High efficiency and long life) can be maintained. By eliminating the need to provide a hole transport layer and an electron blocking layer separately, the number of depositions is reduced, manufacturing costs are reduced, and performance degradation and dark spots are prevented from occurring due to contamination between layers during deposition. And an organic EL element capable of stable mass production can be provided.

In this embodiment, the electron affinity (Af) of the hole injection layer is preferably 4.8 eV or more and 5.8 eV or less.
Further, the ionization potential (Ip) of the hole transport layer is preferably 5.5 eV or more and 6.0 eV or less. Furthermore, the electron affinity (Af) of the hole transport layer is preferably 2.0 eV or more and 2.4 eV or less.

Electron affinity (Af, electron affinity) means the energy released or absorbed when one electron is given to the molecule of the host material, and is defined as positive in the case of emission and negative in the case of absorption. To do.
The electron affinity is defined by the ionization potential (Ip) and singlet energy (Eg (S): energy level difference between the lowest excited singlet state and the ground state) as follows.
Af = Ip-Eg (S)
Here, the ionization potential (Ip) means the energy required to remove ions from the compound and ionize, and is a value measured by, for example, an ultraviolet photoelectron spectrometer (AC-3, Riken Keiki Co., Ltd.). .
Singlet energy (Eg (S)) refers to the optical energy difference between the conduction level and the valence level. For example, the long-wavelength side tangent of the absorption spectrum of the diluted toluene solution of each material and the baseline (zero absorption) Obtained by converting the wavelength value of the intersection into energy.

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

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO): indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide And graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a metal material nitride (for example, titanium nitride).

  These materials are usually formed by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1% by mass to 10% by mass of zinc oxide is added to indium oxide. For example, indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide. By using a target, it can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method, etc.

Of the organic layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode. Any material that can be used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) can be used.
An element belonging to Group 1 or Group 2 of the periodic table, which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. Note that when an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

(Light emitting layer)
-Dopant material A light emitting layer is a layer containing a highly luminescent substance, and can use various materials. For example, as the substance having high light-emitting property, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.
As a blue fluorescent material that can be used for the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used. Specifically, N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine (abbreviation: PCBAPA) and the like.
An aromatic amine derivative or the like can be used as a green fluorescent material that can be used for the light emitting layer. Specifically, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1′-biphenyl-2-yl)]-N- [4- (9H-carbazole) -9-yl) phenyl ] -N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N, N, 9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.
Tetracene derivatives, diamine derivatives, and the like can be used as red fluorescent materials that can be used for the light emitting layer. Specifically, N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

Examples of phosphorescent materials that can be used for the light emitting layer include ortho metalated complexes of metal atoms selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt).
As a blue phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used. Specifically, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6), bis [2- (4 ′ , 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ′, 5′bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium (III ) Picolinate (abbreviation: Ir (CF ₃ ppy) ₂ (pic)), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) acetylacetonate (abbreviation: FIracac) Etc.
An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer. Tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) 3), bis (2-phenylpyridinato-N, C2 ′) iridium (III) acetylacetonate ( Abbreviations: Ir (ppy) ₂ (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) ₂ (acac)), bis (benzo [ h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) ₂ (acac)) and the like.
As a red phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used. Specifically, bis [2- (2′-benzo [4,5-α] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (btp) ₂ (acac)), Bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) ₂ (acac)), (acetylacetonato) bis [2,3-bis (4-fluoro Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) ₂ (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation) : PtOEP) and the like.
In addition, tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) ₃ (Phen)), tris (1,3-diphenyl-1,3-propanedionate) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) ₃ (Phen)), tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Since rare earth metal complexes such as TTA) ₃ (Phen)) emit light from rare earth metal ions (electron transition between different multiplicity), they can be used as phosphorescent compounds.
In the present embodiment, among these, it is preferable to use a phosphorescent material having an emission peak wavelength of 530 nm or more and 620 nm.

-Host material As a light emitting layer, it is good also as a structure which disperse | distributed the high luminescent substance (dopant material) mentioned above to another substance (host material). Various materials can be used as a material for dispersing a highly luminescent substance. The lowest unoccupied orbital level (LUMO level) is higher than that of a highly luminescent substance, and the highest occupied orbital level ( It is preferable to use a substance having a low HOMO level.
Substances (host materials) for dispersing highly luminescent substances include 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives, etc. Heterocyclic compounds, 3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 3) aromatic amine compounds such as triarylamine derivatives, or condensed polycyclic aromatic amine derivatives used.

Specifically, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h Quinolinato) beryllium (II) (abbreviation: BeBq ₂ ), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) ) (Abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) ) And the like, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadi Azole (abbreviation: PBD), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- ( 4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 2,2 ′, 2 ″-(1,3,5-benzene Heterocyclic compounds such as triyl) tris (1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 9- [4- (10-phenyl) -9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole Abbreviations: DPCzPA), 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2-tert-butyl-9, 10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9′-bianthryl (abbreviation: BANT), 9,9 ′-(stilbene-3,3′-diyl) diphenanthrene (abbreviation: DPNS) ), 9,9 ′-(stilbene-4,4′-diyl) diphenanthrene (abbreviation: DPNS2), 3,3 ′, 3 ″-(benzene-1,3,5-triyl) tripylene (abbreviation: TPB3) ), 9,10-diphenylanthracene (abbreviation: DPAnth), condensed aromatic compounds such as 6,12-dimethoxy-5,11-diphenylchrysene, N, N-diphenyl- 9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10-phenyl-9-anthryl) triphenylamine (abbreviation: DPhPA), N, 9-diphenyl-N- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA), N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) phenyl] phenyl} -9H-carbazol-3-amine (abbreviation: PCAPBA), N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazole Aromatic amine compounds such as -3-amine (abbreviation: 2PCAPA), NPB (or α-NPD), TPD, DFLDPBi, and BSPB Etc. can be used. In addition, a plurality of kinds of substances (host materials) for dispersing a substance having high luminescence (dopant material) can be used.

  In this embodiment, when an anthracene derivative is used as the host material, it is either a compound represented by the following general formula (3-1) or a compound represented by the following general formula (3-2). It is preferable.

(In the general formulas (3-1) and (3-2),
R ^{301 to} R ³⁰⁸ are each independently
Hydrogen atom,
Halogen atoms,
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 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 ^{31 to} Ar ³³ , R ³⁰⁹ , R ³¹⁰ , R ^{311 to} R ³¹⁸ are each independently
Hydrogen atom,
Halogen atoms,
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 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,
A substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms,
It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Adjacent R ^{311 to} R ³¹⁸ 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 (3-2), when Ar ³¹ , Ar ³³ , R ³⁰⁹ , and R ³¹⁰ are hydrogen atoms, Ar ³² is a substituted or unsubstituted aromatic hydrocarbon having 10 to 30 ring carbon atoms. It is a group. )

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

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. For the electron injection layer, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. An alkali metal, an alkaline earth metal, or a compound thereof can be used. In addition, a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property, specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.

  Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer described above is used. be able to. The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

(cathode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.

Note that in the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.
By providing an electron injection layer, a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

(Method for forming each layer of organic EL element)
The method for forming each layer of the organic EL element 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 element is a known method by a coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, an ink jet method, etc., in which the organic EL element material is dissolved in a solvent. Can be formed.

(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.

[Electronics]
The organic EL element of the present embodiment 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 vehicle lamp.

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

The light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL element has a plurality of light emitting layers, each of the plurality of light emitting layers 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.

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

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

  Examples of the hole-injecting material include those described above, and 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) and the like 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.

EXAMPLES Next, although an Example is given and this invention is demonstrated in more detail, this invention is not restrict | limited at all to the content of description of these Examples.
The compound used for manufacture of an organic EL element is shown below.

[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 100 nm.
The glass substrate with the ITO transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and first, the compound HI-1 is deposited so as to cover the transparent electrode on the surface on which the ITO transparent electrode line is formed. Then, a HI-1 film having a thickness of 10 nm was formed to form a hole injection layer.
Next, on this HI-1 film | membrane, compound HT-1 was vapor-deposited as a positive hole transport material, the HT-1 film | membrane with a film thickness of 50 nm was formed into a film, and the positive hole transport layer was formed.
Further, on this HT-1 film, a compound PG-1 as a first host material, a compound PG-2 as a second host material, and Ir (bzq) ₃ as a phosphorescent dopant material were co-evaporated. Thus, a light emitting layer having a thickness of 30 nm showing yellow light emission was formed. The concentration of the first host material and the second host material was 45% by mass, and the dopant concentration was 10% by mass.
And on this light emitting layer, compound ET was vapor-deposited and the 35-nm-thick ET film | membrane was formed into a film, and the electron carrying layer was formed.
Next, on this ET film, LiF was deposited 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.

-Examples 2-3
The organic EL elements of Examples 2 to 3 were produced in the same manner as in Example 1 except that the compound HT-1 of the hole transport layer in Example 1 was changed to the compounds described in Table 1.

・ Comparative Examples 1-9
The organic EL elements of Comparative Examples 1 to 3 were the same as Example 1 except that the compound HI-1 of the hole injection layer and the compound HT-1 of the hole transport layer in Example 1 were changed to the compounds shown in Table 1. It produced similarly.
In addition, in the organic EL elements of Comparative Examples 4 to 9, the hole transport layer was changed from the compound HI of the hole injection layer and the compound HT-1 of the hole transport layer in Example 1 to the compounds shown in Table 1. Was provided with a thickness of 40 nm, and an electron blocking layer with a thickness of 10 nm was provided between the hole transport layer and the light emitting layer. Table 1 shows the compounds used in the electron blocking layer.

[Evaluation of organic EL elements]
About the produced organic EL element, voltage, current efficiency L / J, and lifetime were evaluated. The results are shown in Table 2.

・ Voltage V
The voltage (unit: V) was measured when current was applied between ITO and Al so that the current density was 10.0 mA / cm ² .
・ Current efficiency L / J
Spectral radiance spectrum when voltage was applied to the device so that the current density was 10.0 mA / cm ² was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta), and the obtained spectral radiance spectrum From this, the current efficiency (unit: cd / A) was calculated.

・ 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 can be seen that the organic EL elements of Examples 1 to 3 are significantly lower in voltage and higher in efficiency than the organic EL elements of Comparative Examples 1 to 3. When the example using the same compound for the hole transport layer and the comparative example were compared (that is, Example 1 and Comparative Example 1, Example 2 and Comparative Example 2, Example 3 and Comparative Example 3), the lifetime It can also be seen that the life has been significantly extended.
The organic EL elements of Comparative Examples 1 to 3 are provided with an electronic block layer as shown in Comparative Examples 7 to 9, whereby the voltage is lowered, and the organic EL elements have high efficiency and long life. On the other hand, the organic EL elements of Examples 1 to 3 exhibit the same voltage, luminous efficiency, and life as Comparative Examples 7 to 9 without providing an electron blocking layer. Moreover, the organic EL element of Examples 1-3 shows the voltage, luminous efficiency, and lifetime equivalent to the organic EL element which provided the electronic block layer, as shown in Comparative Examples 4-6. That is, it can be seen that the organic EL elements of Examples 1 to 3 are organic EL elements that are driven at a sufficiently low voltage and have a high efficiency and a long life even without an electronic block layer. That is, the number of layers of the organic EL element can be reduced.

Example 4
A glass substrate with an ITO transparent electrode of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.
The glass substrate with the ITO transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and first, the compound HI-1 is deposited so as to cover the transparent electrode on the surface on which the ITO transparent electrode line is formed. Then, a HI-1 film having a thickness of 10 nm was formed to form a hole injection layer.
Next, on this HI-1 film | membrane, compound HT-1 was vapor-deposited as a positive hole transport material, and HT-1 film | membrane with a film thickness of 90 nm was formed into a film, and the positive hole transport layer was formed.
Further, Compound BH was vapor-deposited on this HT-1 film to form a light emitting layer having a thickness of 25 nm. At the same time, compound BD was co-evaporated as a fluorescent material. The concentration of Compound BD was 4.0% by mass. This co-deposited film functions as a light emitting layer.
And on this light emitting layer, compound EEL was vapor-deposited and the EEL film | membrane with a film thickness of 25 nm was formed into a film, and the electronic barrier was formed.
Next, on this EEL film, a compound ET was vapor-deposited to form an ET film having a thickness of 10 nm to form an electron transport layer.
Next, on this ET film, LiF was deposited 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 voltage and current efficiency of the produced organic EL element were evaluated in the same manner as in Example 1. The lifetime (LT90) was measured by applying a voltage to the device so that the current density was 50.00 mA / cm ² and measuring the time (unit: h) until the luminance reached 90% with respect to the initial luminance. . The evaluation results are shown in Table 4.

-Examples 5-12
The organic EL elements of Examples 5 to 12 were produced in the same manner as in Example 4 except that the compound HT-1 in the hole transport layer in Example 4 was changed to the compounds described in Table 3.

Comparative Examples 10-18
The organic EL elements of Comparative Examples 10 to 18 were the same as Example 4 except that the compound HI-1 of the hole injection layer and the compound HT-1 of the hole transport layer in Example 4 were changed to the compounds shown in Table 3. It produced similarly.

Comparative Examples 19-36
The organic EL devices of Comparative Examples 19 to 36 were prepared by changing the compound HI of the hole injection layer and the compound HT-1 of the hole transport layer in Example 4 to the compounds shown in Table 3, and forming the hole transport layer into a film. An electron blocking layer having a thickness of 10 nm was provided between the hole transport layer and the light emitting layer. Table 3 shows the compounds used in the electric blocking layer.

As Table 4 shows, the organic EL elements of Examples 4 to 12 have a significantly lower voltage and higher efficiency than the organic EL elements of Comparative Examples using the same hole transport material in Comparative Examples 10 to 18. It can be seen that the life is extended.
As shown in Comparative Examples 28 to 36, the organic EL elements of Comparative Examples 10 to 18 are provided with an electron blocking layer between the hole transport layer and the light emitting layer, thereby lowering the voltage and providing high efficiency and long life. It becomes an organic EL element. On the other hand, the organic EL elements of Examples 4 to 12 exhibit the same voltage, luminous efficiency, and lifetime as Comparative Examples 28 to 36 without providing an electronic block layer. Moreover, the organic EL element of Examples 4-12 shows the voltage, luminous efficiency, and lifetime equivalent to the organic EL element which provided the electronic block layer, as shown in Comparative Examples 10-18. That is, it can be seen that the organic EL elements of Examples 4 to 12 are organic EL elements that are driven at a sufficiently low voltage and have a high efficiency and a long life even without an electronic block layer. That is, the number of layers of the organic EL element can be reduced.

DESCRIPTION OF SYMBOLS 1 ... Organic EL element 2 ... Substrate 3 ... Anode 4 ... Cathode 5 ... Light emitting layer 6 ... Hole transport layer 7 ... Hole injection layer 8 ... Electron injection / transport layer 10 ... Organic layer

Claims (24)

The anode,
A cathode provided opposite to the anode;
A light emitting layer provided between the anode and the cathode;
A hole transport layer provided adjacent to the light emitting layer between the anode and the light emitting layer;
A hole injection layer provided between the anode and the hole transport layer,
The hole transport layer and the hole injection layer are adjacent,
The hole transport layer includes a compound represented by the following general formula (1),
The hole injection layer is a first ring selected from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 6 to 24 ring atoms. An organic electroluminescence device characterized in that the structure contains a condensed compound formed by condensing 2 or more and 3 or less of the structure represented by the following general formula (2a).

(In the general formula (1),
A ¹ and A ² are independent of each other
It represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹ , L ² and L ³ are each independently a single bond or a divalent linking group,
As the linking group in L ¹ , L ² and L ³ ,
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms;
A multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded;
A multiple linking group in which 2 to 4 groups selected from the heterocyclic group are bonded, or a group in which 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group are bonded It is a multiple linking group.
The aromatic hydrocarbon group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may form a ring when adjacent groups are bonded to each other or may not form a ring. .
Y ^{1 to} Y ¹⁶ each independently represent C (R) or a nitrogen atom,
Each R is independently
Hydrogen atom,
Halogen atoms,
Hydroxyl group,
A cyano group,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
A substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms,
A substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
It 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.
However, one of Y ^{5 to} Y ⁸ and one of Y ^{9 to} Y ¹² are carbon atoms bonded to L ³ .
One or more sets of Y ¹ and Y ² , Y ² and Y ³ , Y ³ and Y ⁴ , Y ¹³ and Y ¹⁴ , Y ¹⁴ and Y ¹⁵ , and Y ¹⁵ and Y ¹⁶ are represented by the following general formula (1a ) May bond to a carbon atom. )

(In the general formula (1a),
Each * is any of Y ¹ and Y ² , Y ² and Y ³ , Y ³ and Y ⁴ , Y ¹³ and Y ¹⁴ , Y ¹⁴ and Y ¹⁵ , and Y ¹⁵ and Y ^{16 in} the general formula (1). Or a bond position to a set of carbon atoms.
X ¹ is an oxygen atom, a sulfur atom, CR ⁵ R ⁶ , or NR ⁷ .
R ^{1 to} R ⁷ have the same meaning as R in the general formula (1). )

(In the general formula (2a),
a is a ring structure condensed to the first ring structure, and is represented by the following general formula (2b).
X ²¹ and X ²² are each independently C (R) or a nitrogen atom.
R ²¹ and R ²² are independently the same as R in the general formula (1). )

(In the general formula ^{(2b), X 20} is represented by any one of the following formulas (2b-1) ~ (2b -12).)

(In the general formulas (2b-1) to (2b-12), R ²⁰ has the same meaning as R in the general formula (1).) The organic electroluminescent device according to claim 1,
The said condensation compound is represented by the following general formula (2-1) or (2-2), The organic electroluminescent element characterized by the above-mentioned.

(In the general formulas (2-1) and (2-2),
Ar ²¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 6 to 24 ring atoms,
a ^{21 to} a ²³ are each independently synonymous with a in the general formula (2a).
X ^{23 to} X ²⁸ are independently the same as X ²¹ and X ²² in the general formula (2a).
R ^{23 to} R ²⁸ are each independently synonymous with R ²¹ and R ²² in the general formula (2a). ) In the organic electroluminescent element according to claim 1 or 2,
The compound represented by the general formula (1) is represented by any one of the following general formulas (1-1) and (1-2).

(In the general formulas (1-1) and (1-2), A ¹ , A ² , L ¹ , L ² , L ³ , Y ^{1 to} Y ¹⁶ are respectively A ¹ in the general formula (1). , A ² , L ¹ , L ² , L ³ , Y ^{1 to} Y ¹⁶ . In the organic electroluminescent element according to claim 1 or 2,
The compound represented by the general formula (1) is represented by any one of the following general formulas (1-A) to (1-G).


(In the general formulas (1-A) to (1-G), A ¹ , A ² , L ¹ , L ² , L ³ are respectively A ¹ , A ² , L ¹ in the general formula (1). , L ² and L ³ .
X ¹ has the same meaning as ^{X 1} in the general formula (1a).
Z ^{11 to} Z ¹⁸ are carbon atoms, one of Z ^{11 to} Z ¹⁴ , and one of Z ^{15 to} Z ¹⁸ are carbon atoms bonded to L ³ .
Several R < ¹¹ > -R < ¹⁵ > is synonymous with R in the said General formula (1) each independently.
p is 4, q is 2, n is 4, s is 3, and t is 3. ) In the organic electroluminescent element according to claim 4,
L ³ in the general formulas (1-A) to (1-G) is
A bond that connects Z ¹³ and Z ¹⁷ , a bond that connects Z ¹³ and Z ¹⁶ , or
An organic electroluminescence element, which is a bond that bonds Z ¹² and Z ¹⁷ together. In the organic electroluminescent element according to claim 5,
L ³ in the general formulas (1-A) to (1-G) is a bond that bonds Z ¹³ and Z ¹⁶ or a bond that bonds Z ¹² and Z ^17. Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 6,
At least one of A ¹ and A ² is a substituted or unsubstituted aromatic hydrocarbon group having 10 to 24 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 9 to 24 ring atoms. An organic electroluminescence device characterized. In the organic electroluminescent element according to any one of claims 1 to 7,
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,
A substituted or unsubstituted benzotriphenylenyl group,
A substituted or unsubstituted dibenzotriphenylenyl group,
A substituted or unsubstituted chrysenyl group,
A substituted or unsubstituted benzocrisenyl group,
A substituted or 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,
A substituted or unsubstituted dibenzothiophenyl group,
A substituted or unsubstituted carbazolyl group,
A substituted or unsubstituted phenanthrenyl group,
An organic electroluminescence device, which represents a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted binaphthyl group. The organic electroluminescent device according to claim 8, wherein
At least one of A ¹ and A ² is
A substituted or unsubstituted dibenzofuranyl group,
A substituted or unsubstituted dibenzothiophenyl group,
An organic electroluminescence device, which represents a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted fluorenyl group. In the organic electroluminescent element according to any one of claims 1 to 9,
The organic electroluminescent device characterized by L ³ is a single bond. In the organic electroluminescent element according to any one of claims 1 to 10,
L ¹ and partial structure represented by -A ^1, a partial structure represented by L ² -A ^2, the organic electroluminescent element being different from each other in the general formula (1). In the organic electroluminescent element according to any one of claims 1 to 11,
L ¹ and L ² are each independently a single bond or a phenylene group, The organic electroluminescent element characterized by the above-mentioned. In the organic electroluminescent element according to any one of claims 2 to 12,
Ar ²¹ is a substituted or unsubstituted benzene ring or a substituted or unsubstituted heterocyclic group having 6 ring-forming atoms. In the organic electroluminescent element according to any one of claims 1 to 13,
Wherein X ²⁰ is an organic electroluminescent device characterized by being represented by the formula (2b-1). In the organic electroluminescent element according to any one of claims 1 to 14,
In the general formula (2a), at least one of R ²¹ and R ²² is
Fluorine atom,
A fluoroalkyl group,
An organic electroluminescence device characterized by being a fluoroalkoxy group or a cyano group. The organic electroluminescence device according to claim 15,
The said condensation compound is represented by either of the following general formula (2-F)-(2-J), The organic electroluminescent element characterized by the above-mentioned.

(In the general formulas (2-F) to (2-J), A ²⁰¹ represents a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group.) In the organic electroluminescent element according to any one of claims 1 to 14,
In the general formula (2a), at least one of R ²¹ and R ²² is
As a substituent,
Fluorine atom,
A fluoroalkyl group,
A substituted aromatic hydrocarbon group having 6 to 24 ring carbon atoms or a heterocyclic group having 6 to 24 ring atoms having at least one group selected from a fluoroalkoxy group or a cyano group; An organic electroluminescence device characterized. The organic electroluminescence device according to claim 17,
The said condensed compound is represented by either of the following general formula (2-A)-(2-E), The organic electroluminescent element characterized by the above-mentioned.

(In the general formulas (2-A) to (2-E), Ar ²⁰¹ is a substituted group having at least one group selected from a fluorine atom, a fluoroalkyl group, a fluoroalkoxy group, or a cyano group as a substituent. It is an aromatic hydrocarbon group having 6 to 24 ring carbon atoms or a substituted heterocyclic group having 6 to 24 ring atoms.) In the organic electroluminescent element according to any one of claims 1 to 18,
The structure represented by the said General formula (2a) in the said condensation compound is mutually the same, The organic electroluminescent element characterized by the above-mentioned. In the organic electroluminescent element according to any one of claims 1 to 19,
The light-emitting layer contains a phosphorescent material that is an orthometalated complex of metal atoms selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt) as a light-emitting material. Organic electroluminescence device. 21. The organic electroluminescence device according to claim 20, wherein an emission peak wavelength of the phosphorescent material is 530 nm or more and 620 nm. In the organic electroluminescent element according to any one of claims 1 to 19,
The said light emitting layer contains a light emitting material and the compound represented by the following general formula (3-1), or the compound represented by the following general formula (3-2), The organic electroluminescent element characterized by the above-mentioned.

(In the general formulas (3-1) and (3-2),
R ^{301 to} R ³⁰⁸ are each independently
Hydrogen atom,
Halogen atoms,
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 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 ^{31 to} Ar ³³ , R ³⁰⁹ , R ³¹⁰ , R ^{311 to} R ³¹⁸ are each independently
Hydrogen atom,
Halogen atoms,
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 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,
A substituted or unsubstituted arylsilyl group having 8 to 50 carbon atoms,
It is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Adjacent R ^{311 to} R ³¹⁸ 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 (3-2), when Ar ³¹ , Ar ³³ , R ³⁰⁹ , and R ³¹⁰ are hydrogen atoms, Ar ³² is a substituted or unsubstituted aromatic hydrocarbon having 10 to 30 ring carbon atoms. It is a group. ) The anode,
A cathode provided opposite to the anode;
A light emitting layer provided between the anode and the cathode;
A hole transport layer provided between the anode and the light emitting layer;
A hole injection layer provided between the anode and the hole transport layer,
The hole transport layer and the hole injection layer are adjacent,
The organic electroluminescence device, wherein the hole injection layer has an electron affinity (Af) of 4.8 eV to 5.8 eV.   An electronic device comprising the organic electroluminescence element according to any one of claims 1 to 23.