JP2018182007A - Material for organic electroluminescent element and organic electroluminescent element - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a material which can increase luminous efficiency of an organic electroluminescent element having a structure where a cathode is formed on a substrate and which can provide an element with a long element lifetime.SOLUTION: There is provided a material for an organic electroluminescent element, which contains a compound having a skeleton derived from fluoranthene, the compound being represented by the following formula (1); (in the formula, R-R, which may be the same or different from each other, each represent one of a hydrogen atom, and an alkyl group, an aromatic hydrocarbon ring group, or a heteroaromatic ring group which may have a substituent.).SELECTED DRAWING: None

Description

The present invention relates to a material for an organic electroluminescent device and an organic electroluminescent device. More particularly, the present invention relates to an organic electroluminescent device material and an organic electroluminescent device used in an organic electroluminescent device having a structure in which a plurality of layers are stacked between an anode and a cathode formed on a substrate.

Organic electroluminescent devices (organic EL devices) are expected as new light emitting devices applicable to thin, flexible and flexible display devices and illuminations, and various studies have been made on materials for further enhancing the device performance.
One of such materials is a compound having a fluoranthene skeleton in its structure, and various studies have been conducted as materials of organic electroluminescent devices (see Patent Documents 1 to 3).

Patent No. 5150731 gazette Patent No. 3961200 gazette JP, 2009-40723, A

The organic electroluminescent device has a structure in which a plurality of layers such as an electron transport layer, a light emitting layer, a hole transport layer and the like are laminated between a cathode and an anode, and the organic electroluminescent device is formed on the anode disposed on the substrate. It is divided into a so-called forward structure organic electroluminescent device in which such a laminated structure is formed, and a so-called reverse structure organic electroluminescent device in which such a laminated structure is formed on a cathode disposed on a substrate. Be In the organic electroluminescent element having the reverse structure, injection of electrons from the cathode is slower than injection of holes from the anode, and there is a problem that holes injected from the anode can not be sufficiently used for light emission. This is one of the problems to be solved in order to increase the light emission efficiency in the organic electroluminescent device of reverse structure. In addition, since it is also required that the organic electroluminescent element can emit light for a long time, one of the problems is to make the element have a long element life.

The present invention has been made in view of the above-mentioned present situation, and provides a material capable of enhancing the luminous efficiency of an organic electroluminescent device having a structure in which a cathode is formed on a substrate and making the device a long lifetime. The purpose is to

The inventors of the present invention have investigated various materials capable of enhancing the luminous efficiency of the so-called reverse structure organic electroluminescent device and providing a device having a long lifetime, and as a result, a compound having a specific structure having a fluoranthene skeleton. When used as a material of a reverse structure organic electroluminescent device, the luminous efficiency of the device can be enhanced, and it is found that the device lifetime will be long, and it is conceived to be able to solve the above problems clearly. The present invention has been achieved.

That is, the present invention is a material used for an organic electroluminescent device having a structure in which a plurality of layers are stacked between an anode and a cathode formed on a substrate, and the material is represented by the following formula (1) ;

(Wherein, R ^{1 to} R ¹⁰ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon ring group, or an aromatic heterocyclic group And a compound having a fluoranthene-derived skeleton represented by

The material for an organic electroluminescent device of the present invention has the above-described structure, and is a material capable of making a reverse structure organic electroluminescent device a device having high luminous efficiency and a long device life. In addition, since the material for an organic electroluminescent element of the present invention can be formed into a film by coating, the unevenness of the oxide layer is flattened by using it as a material of a buffer layer of an element having an oxide layer and crystallized as a light emitting layer or the like. Even in the case of using a material which easily causes the leakage, the leakage current is suppressed, and an element capable of obtaining uniform surface emission can be obtained.

FIG. 7 is an NMR chart of the compound synthesized in step 2 of Example 1. FIG. 7 is an NMR chart of fluoranthene A synthesized in step 3 of Example 1. FIG. 7 is an NMR chart of fluoranthene B synthesized in Example 2. FIG. It is the schematic which showed an example of the structure of the organic electroluminescent element of this invention.

The present invention will be described in detail below.
In addition, what combined two or more of each preferable form of this invention described below is also a preferable form of this invention.

The compound having a framework derived from fluoranthene (hereinafter also referred to as a fluoranthene compound) contained in the material for an organic electroluminescent device of the present invention has the following formula (1);

(Wherein, R ^{1 to} R ¹⁰ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon ring group, or an aromatic heterocyclic group It is a compound represented by.).
The material for an organic electroluminescent device of the present invention is preferably used as a material for forming an electron injection layer of a reverse structured organic electroluminescent device, and when it is used as such, the luminous efficiency of the reverse structured organic electroluminescent device And the element life can be made long. The reason is considered as follows.
Materials used for the electron injection layer and the electron transport layer of the reverse structure organic electroluminescent device include (1) low energy level of LUMO (lowest unoccupied orbital), (2) LUMO and HOMO (highest occupied orbital) It is considered necessary that the difference in energy levels (band gap) is large, and (3) the redox tolerance is high. Generally, an electron-withdrawing substituent such as pyridine is often introduced to lower the LUMO level, but the electron-withdrawing site is often susceptible to oxidation. In addition, since oxidation is caused by holes, molecular design is important such that HOMO is not localized to the electron-withdrawing substituent. Since fluoranthene is a material consisting only of carbon and hydrogen and is free from nitrogen and the like, it is considered to be relatively stable to redox. In addition, it has a wide band gap and a low LUMO level. Furthermore, since both HOMO and LUMO are localized at the central site, HOMO will not be localized there even if an electron-withdrawing substituent is introduced to further lower LUMO. From these points, by using a compound having a fluoranthene-derived skeleton represented by the above formula (1) as a material of a reverse structure organic electroluminescent device, the device can have high luminous efficiency and a long device life. it is conceivable that.
Further, in the fluoranthene compound represented by the above formula (1), the fluoranthene having a ring structure at the center, even when any one of R ^{1 to} R ¹⁰ is an aromatic hydrocarbon ring group or an aromatic heterocyclic group. Since the compound can be arranged not to be coplanar with the condensed ring structure of the skeleton, the crystallinity of the compound is low, which is also suitable as the material of the organic electroluminescent device.

In the above formula (1), R ^{1 to} R ¹⁰ are the same or different and any of a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon ring group or an aromatic heterocyclic group Represents

As said alkyl group, a C1-C18 linear alkyl group, a C3-C18 branched alkyl group, a C3-C18 cycloalkyl group is mentioned as a suitable thing, for example.
Specific examples of the linear alkyl group having 1 to 18 carbon atoms include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group and n-heptyl group, n-octyl group, n-nonyl group etc. are mentioned.
Specific examples of the above branched alkyl group having 3 to 18 carbon atoms include isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, isohexyl, isoheptyl, isooctyl and isononyl groups. Can be mentioned.
Specifically as said C3-C18 cycloalkyl group, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group etc. are mentioned.
The above alkyl group is preferably a linear alkyl group having 1 to 18 carbon atoms or a branched alkyl group having 3 to 18 carbon atoms, and among these, the upper limit of the carbon number is preferably 14 and 10 is preferable. More preferred is, for example, methyl group, ethyl group, isopropyl group, isobutyl group or octyl group.

As said aromatic hydrocarbon ring group, a C6-C18 thing is mentioned as a suitable thing, Specifically, a benzene, naphthalene, anthracene etc. are mentioned as a more preferable thing.
The upper limit of the carbon number of the aromatic hydrocarbon ring group is preferably 14, more preferably 10, still more preferably 9, and specifically, benzene is particularly preferred.

As the above-mentioned aromatic heterocyclic group, a hetero atom which is an atom other than carbon and hydrogen is contained as a ring constituting atom, and one having a carbon number of 0 to 10 is mentioned as a preferable example, and specifically, it is a pentazole -Membered ring heterocyclic group such as triazole, tetrazole, imidazole, oxazole, isoxazole, thiazole, isothiazole, pyrazole, pyrrole, oxadiazole, oxazoline, furan, thiophene, etc .; pyridine, pyrazine, quinoline, isoquinoline, phenanthroline, thiazine And 6-membered ring heterocyclic groups are preferable. Among these, the upper limit of the carbon number of the aromatic heterocyclic group is preferably 12, more preferably 9, and still more preferably 5, among these. The lower limit of the number of carbon atoms is preferably 1, more preferably 2, and still more preferably 3. As the above-mentioned aromatic heterocyclic group, those having a nitrogen atom such as pyridine, pyrazine, furan, thiophene and imidazole are particularly preferable.

The alkyl group of R ^{1 to} R ¹⁰ , the aromatic hydrocarbon ring group, and the aromatic heterocyclic group may have a substituent.
Examples of the substituent include an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and 6 to 12 carbon atoms. And an alkylamino group having 1 to 12 carbon atoms or an arylamino group having 6 to 18 carbon atoms.

The alkyl group as the substituent, the aromatic hydrocarbon ring and the aromatic heterocyclic group are preferably the same as those described above.
As said halogen atom, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom is mentioned, Especially, a fluorine atom is preferable.

The above-mentioned alkoxy group having 1 to 12 carbon atoms is methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, n-pentyloxy group, n-hexyloxy group And linear or branched ones such as n-heptyloxy group and n-octyloxy group.
The carbon number of the alkoxy group having 1 to 12 carbon atoms is preferably 1 to 8, more preferably 1 to 6, and still more preferably 1 to 3.

As said C6-C12 aryloxy group, a phenyloxy group, a benzyloxy group, etc. are mentioned.
Among the above-mentioned aryloxy groups having 6 to 12 carbon atoms, those having 6 to 10 carbon atoms are preferable. More preferably, it is 6-8. More preferably, it is 6.

Examples of the alkylamino group having 1 to 12 carbon atoms include monoalkylamino groups having 1 to 12 carbon atoms such as a methylamino group and an ethylamino group; and 2 carbon atoms such as a dimethylamino group, a diethylamino group, a pyridinyl group and a morpholinyl group. -12 acyclic or cyclic dialkylamino groups are mentioned as suitable.
The carbon number of the alkylamino group having 1 to 12 carbon atoms is preferably 1 to 8, more preferably 1 to 6, and still more preferably 1 to 4.

As said C6-C18 arylamino group, C6-C18 monoaryl amino groups, such as a phenylamino group and a benzylamino group; N-alkyl-N-, such as N-methyl-N- phenylamino group Preferable examples include an arylamino group; a diarylamino group having a carbon number of 12 to 18, such as a diphenylamino group, a carbazolyl group, a phenoxazinyl group, and a phenothiazinyl group.
The carbon number of the arylamino group having 6 to 18 carbon atoms is preferably 8 to 18, more preferably 12 to 18, and still more preferably 12.

In addition, the above substituents include acyl groups such as acetyl, propionyl and butyryl; N, N-dialkylcarbamoyl such as N, N-dimethylcarbamoyl and N, N-diethylcarbamoyl; thioacetyl and thiobenzoyl Group, thiocarbonyl group such as methoxythiocarbonyl group; dioxaborolanyl group, stannyl group, silyl group, ester group, formyl group, thioether group, epoxy group, isocyanate group, hydroxyl group, sulfo group, sulfonyl group, phosphoryl It may be a group, a carboxyl group or the like.

The above substituent may be further substituted by a halogen atom, a hetero atom, an alkyl group, an alkoxy group, an alkenyl group, an alkynyl group, an aromatic ring or the like as long as the effects of the present invention can be exhibited. There are no particular limitations on the position or number at which the substituent is attached.

In the present invention, it is preferable that at least one of R ^{7 to} R ^{10 in} the above formula (1) is an aromatic hydrocarbon ring group which may have a substituent, or an aromatic heterocyclic group. If it is such a structure, a conjugated structure will spread and it will become a more stable compound.
More preferably, two to four of R ^{7 to} R ¹⁰ are an aromatic hydrocarbon ring group which may have a substituent or an aromatic heterocyclic group, and more preferably R ⁷ all aromatic optionally substituted hydrocarbon ring group to R ^10, or is that it is an aromatic heterocyclic group.

In the above formula (1), at least one of R ⁷ to R ¹⁰ is an aromatic hydrocarbon ring group as a substituent, or is preferably an aromatic hydrocarbon ring having aromatic heterocyclic group. If it is such a structure, a conjugated structure will further spread and it will become a compound with high stability. It is preferable that the number of the aromatic hydrocarbon ring group and the aromatic heterocyclic group having an aromatic hydrocarbon ring group and an aromatic heterocyclic group as a substituent is larger, and it is preferable that 2 to 4 have such a structure.

Although the manufacturing method in particular of the compound which has a framework derived from fluoranthene represented by the said Formula (1) is not restrict | limited, For example, it can manufacture by reaction formula (2), (3) shown to a following formula.

The present invention is also an organic electroluminescent device having a structure in which a plurality of layers are laminated between an anode and a cathode formed on a substrate, which is configured using the material for an organic electroluminescent device of the present invention. is there. As described above, by using the material for an organic electroluminescent device of the present invention, the light emitting efficiency of the organic electroluminescent device having the reverse structure is high, and the device life can be made long.

The layers constituting the organic electroluminescent device include an anode, a cathode, a light emitting layer, an electron injecting layer, an electron transporting layer, a hole transporting layer, a hole injecting layer and the like, and these layers are appropriately selected. The layers are stacked to form an organic electroluminescent device.
The structure of the layers to be laminated is not particularly limited as long as the organic electroluminescent device of the present invention has a structure in which a plurality of layers are laminated between the anode and the cathode formed on the substrate. It is preferable that the element is a device in which layers of a cathode, an electron injection layer, an electron transport layer, a light emitting layer, and if necessary, a hole transport layer, a hole injection layer, and an anode are adjacently stacked in this order.
When the organic electroluminescent element of the present invention has a buffer layer described later, the buffer layer preferably functions as an electron injection layer. When the organic electroluminescent device of the present invention has a buffer layer functioning as an electron injection layer, a cathode, a buffer layer, if necessary, an electron transport layer, a light emitting layer, if necessary, a hole transport layer, a hole injection layer, It is preferable that it is an element (element of a first element structure) in which each layer of the anode is stacked adjacent to this in this order.
In addition, the organic electroluminescent device of the present invention may have an electron injection layer as an independent layer separately from the buffer layer, in which case a cathode, an electron injection layer, a buffer layer, an electron transport layer as needed, It is preferable that the light-emitting layer, and the hole transport layer, the hole injection layer, and the anode, if necessary, be an element (element of a second element structure) stacked adjacent to each other in this order.
Each of these layers may be composed of one layer or two or more layers.

In the organic electroluminescent device of the present invention, as the anode and the cathode, known conductive materials can be appropriately used, but at least one of them is preferably transparent for light extraction. Examples of known transparent conductive materials include ITO (tin-doped indium oxide), ATO (antimony-doped indium oxide), IZO (indium-doped zinc oxide), AZO (aluminum-doped zinc oxide), FTO (fluorine-doped indium oxide), etc. Is raised. Examples of opaque conductive materials include calcium, magnesium, aluminum, tin, indium, copper, silver, gold, platinum and alloys thereof.
Among these, ITO, IZO and FTO are preferable as the cathode.
Among these, Au, Ag and Al are preferable as the anode.
As described above, since metals generally used for the anode can be used for the cathode and the anode, the case where light extraction from the upper electrode is assumed (in the case of the top emission structure) can be easily realized, and Various types can be selected and used for each electrode. For example, Al is used as the lower electrode, and ITO or the like is used for the upper electrode.

The average thickness of the cathode is not particularly limited, but is preferably 10 to 500 nm. More preferably, it is 100 to 200 nm. The average thickness of the cathode can be measured by a stylus profilometer, spectroscopic ellipsometry.
Although the average thickness of the said anode is not specifically limited, It is preferable that it is 10-1000 nm. More preferably, it is 30 to 150 nm. In addition, even when using an opaque material, for example, by setting the average thickness to about 10 to 30 nm, it can be used as a top emission type and transparent type anode.
The average thickness of the anode can be measured at the time of film formation by a quartz oscillator film thickness meter.

The organic electroluminescent device of the present invention preferably has a metal oxide layer between the anode and the cathode.
When a metal oxide is used as the material of the laminated structure between the anode and the cathode, the continuous driving life and storage stability become excellent as compared with the organic electroluminescent device having no layer made of a metal oxide.
More preferably, a first metal oxide layer is provided between the cathode and the light emitting layer, and a second metal oxide layer is provided between the anode and the light emitting layer.
The importance of the metal oxide layer is higher in the first metal oxide layer, and the second metal oxide layer is also replaced with an organic material extremely deep in the lowest unoccupied molecular orbital, for example, HATCN. Can.

The first metal oxide layer functions as a part of a cathode or an electron injection layer, and the second metal oxide layer functions as a hole injection layer.
If the first metal oxide layer is considered to be part of the cathode, the device having the first metal oxide layer is preferably a device having the first device structure described above, and the first metal oxide layer If the element is considered to be an electron injection layer, the element having the first metal oxide layer is preferably an element of the second element structure described above.
The first metal oxide layer is a layer formed of a single metal oxide film, or a layer obtained by laminating and / or mixing one or more metal oxides, and a layer of a semiconductor or insulator laminated thin film It is. The metal elements constituting the metal oxide include magnesium, calcium, strontium, barium, titanium, zirconium, hafnium, vanadium, niobium, tantalum, chromium, molybdenum, tungsten, manganese, indium, gallium, iron, cobalt, nickel, copper And zinc, cadmium, aluminum and silicon. Among these, it is preferable that at least one of the metal elements constituting the laminated or mixed metal oxide layer is a layer consisting of magnesium, aluminum, calcium, zirconium, hafnium, silicon, titanium, zinc, and among them, a single metal If it is an oxide, it is preferable to include a metal oxide selected from the group consisting of magnesium oxide, aluminum oxide, zirconium oxide, hafnium oxide, silicon oxide, titanium oxide and zinc oxide.

Examples of layers obtained by laminating and / or mixing one or more metal oxides described above include titanium oxide / zinc oxide, titanium oxide / magnesium oxide, titanium oxide / zirconium oxide, titanium oxide / aluminum oxide, titanium oxide / Lamination and / or combination of metal oxides such as hafnium oxide, titanium oxide / silicon oxide, zinc oxide / magnesium oxide, zinc oxide / zirconium oxide, zinc oxide / hafnium oxide, zinc oxide / silicon oxide, calcium oxide / aluminum oxide Mixtures, titanium oxide / zinc oxide / magnesium oxide, titanium oxide / zinc oxide / zirconium oxide, titanium oxide / zinc oxide / aluminum oxide, titanium oxide / zinc oxide / hafnium oxide, titanium oxide / zinc oxide / silicon oxide, Such as indium oxide / gallium oxide / zinc oxide Like those laminating and / or mixing a combination of species of metal oxides. Among these, IGZO which is an oxide semiconductor exhibiting good characteristics as a special composition and 12CaO 7 Al ₂ O ₃ which is an electride are also included.
In the present invention, a material having a sheet resistance of less than 100 Ω / □ is classified as a conductor, and a material having a sheet resistance of more than 100 Ω / □ is classified as a semiconductor or an insulator. Therefore, ITO (tin-doped indium oxide), ATO (antimony-doped indium oxide), IZO (indium-doped zinc oxide), AZO (aluminum-doped zinc oxide), FTO (fluorine-doped indium oxide), etc. known as transparent electrodes The thin film is not included in the layer constituting the first metal oxide layer of the present invention because it has high conductivity and is not included in the category of semiconductor or insulator.

The metal oxide for forming the second metal oxide layer is not particularly limited, but vanadium oxide (V ₂ O ₅ ), molybdenum oxide (MoO ₃ ), tungsten oxide (WO ₃ ), ruthenium oxide (RuO ₂₎ Etc. can be used alone or in combination of two or more. Among these, those containing vanadium oxide or molybdenum oxide as the main component are preferable. When the second metal oxide layer is composed of vanadium oxide or molybdenum oxide as a main component, the second metal oxide layer injects holes from the anode and transports it to the light emitting layer or the hole transport layer The function as a hole injection layer is better. In addition, vanadium oxide or molybdenum oxide has an advantage that it can suitably prevent the injection efficiency of holes from the anode to the light emitting layer or the hole transport layer from being lowered because the hole transportability of itself is high. There is. More preferably, it is composed of vanadium oxide and / or molybdenum oxide.

The average thickness of the first metal oxide layer is preferably 1 nm to several μm, but is preferably 1 to 1000 nm from the viewpoint of forming an organic electroluminescent device which can be driven at a low voltage. More preferably, it is 2 to 100 nm.
The average thickness of the second metal oxide layer is not particularly limited, but is preferably 1 to 1000 nm. More preferably, it is 5 to 50 nm.
The average thickness of the first metal oxide layer can be measured by a stylus profilometer, spectroscopic ellipsometry.
The average thickness of the second metal oxide layer can be measured at the time of film formation by a quartz oscillator film thickness meter.

The organic electroluminescent device of the present invention has a buffer layer formed by applying a solution containing an organic compound such as a fluoranthene compound represented by the above formula (1) between the metal oxide layer and the light emitting layer. Is preferred.
The metal oxide layer of the organic electroluminescent element is formed by a method such as a spray pyrolysis method, a sol-gel method, a sputtering method or the like as described later, and the surface is not smooth but has unevenness. When the light emitting layer is formed on this metal oxide layer by vacuum evaporation or the like, the unevenness of the surface of the metal oxide layer becomes a crystal nucleus depending on the kind of the component to be the raw material of the light emitting layer. The crystallization of the material forming the light emitting layer in contact with the object layer is promoted. For this reason, even if the organic electroluminescent device is completed, a large leak current may flow, the light emitting surface may become nonuniform, and a device that can withstand practical use may not be obtained.
However, when a solution is applied to form a buffer layer, a smooth layer can be formed on the surface, so that if a buffer layer is formed by application between the metal oxide layer and the light emitting layer, the light emitting layer is formed. Even when the material whose crystallization is suppressed and thereby the organic electroluminescent device having a metal oxide layer uses a material which is easily crystallized as a light emitting layer or the like, the leakage current is suppressed and uniform surface light emission is obtained. It will be possible.
As described above, the compound having a fluoranthene-derived skeleton represented by the above formula (1) can be used as the material of the electron injection layer to make the organic electroluminescent device excellent in luminous efficiency and life. Since it is a material and a compound capable of forming a film by coating, the organic electroluminescent device material of the present invention containing this compound is coated to form a buffer layer, whereby an organic electroluminescent device is obtained. Not only the light emission efficiency and the life can be excellent, but also the leak current can be suppressed, and an element of uniform surface light emission can be obtained.
Thus, it is one of the preferred embodiments of the present invention that the organic electroluminescent device of the present invention has a buffer layer which is a layer of the coating of the material for organic electroluminescent device of the present invention.

The buffer layer preferably has an average thickness of 5 to 100 nm. When the average thickness is in such a range, the effect of suppressing the crystallization of the light emitting layer can be sufficiently exhibited. If the average thickness of the buffer layer is smaller than 5 nm, the irregularities present on the oxide surface can not be sufficiently smoothed, and the leak current may be increased, and the effect of forming the buffer layer may not be sufficiently exhibited. There is. In addition, when the average thickness of the buffer layer is larger than 100 nm, the driving voltage is increased, which is not preferable in practical use. When the material for an organic electroluminescent device of the present invention is used as the material of the buffer layer, the buffer layer can sufficiently exhibit the function as an electron injection layer. The average thickness of the buffer layer is more preferably 10 to 60 nm. Further, in view of the continuous driving life of the organic electroluminescent device of the present invention, the average thickness of the buffer layer is more preferably 10 to 30 nm.
The average thickness of the buffer layer can be measured by a stylus type profilometer and spectroscopic ellipsometry.

In the organic electroluminescent device of the present invention, as a material for forming the light emitting layer, either a low molecular weight compound or a high molecular weight compound may be used, and these may be mixed and used.
In the present invention, the low molecular weight material means a material which is not a polymer material (polymer), and does not necessarily mean an organic compound having a low molecular weight.

Examples of the polymer material forming the light emitting layer include polyacetylene-based compounds such as trans-type polyacetylene, cis-type polyacetylene, poly (di-phenylacetylene) (PDPA), and poly (alkyl, phenylacetylene) (PAPA); Poly (para-phenvinylene) (PPV), poly (2,5-dialkoxy-para-phenylenevinylene) (RO-PPV), cyano-substituted-poly (para-phenvinylene) (CN-PPV), poly ( Polyparaphenylene vinylenes such as 2-dimethyloctylsilyl-para-phenylenevinylene) (DMOS-PPV), poly (2-methoxy 5- (2'-ethylhexoxy) -para-phenylenevinylene) (MEH-PPV) Compound; poly (3-alkylthiophene) (PAT); Polythiophene-based compounds such as propylene) triol (POPT); poly (9,9-dialkylfluorene) (PDAF), poly (dioctylfluorene-alto-benzothiadiazole) (F8BT), α, ω-bis [N, N ′ -Di (methylphenyl) aminophenyl] -poly [9,9-bis (2-ethylhexyl) fluorene-2,7-dyl] (PF2 / 6am4), poly (9,9-dioctyl-2,7-divinylene) Polyfluorene-based compounds such as fluorenyl-ortho-co (anthracene-9,10-diyl)); poly (para-phenylene) (PPP), poly (1,5-dialkoxy-para-phenylene) (RO) -PPP) -like polyparaphenylene compounds; poly (N-vinylcarbazole) (PVK) -like polycarba Compounds; polysilane compounds such as poly (methylphenylsilane) (PMPS), poly (naphthylphenylsilane) (PNPS), poly (biphenylylphenylsilane) (PBPS), and further JP-A-2011-184430 And a boron compound-based polymer material described in JP 2012-151148 A, and the like.

As the low molecular weight material forming the light emitting layer, 8-hydroxyquinoline aluminum (Alq ₃ ), tris (4-methyl-8 quinolinolate) aluminum other than metal complex functioning as a host described later and phosphorescent light emitting material described later (III) (Almq ₃ ), 8-hydroxyquinoline zinc (Znq ₂ ), (1,10-phenanthroline) -tris- (4,4,4-trifluoro-1- (2-thienyl) -butane-1, 3-Gionate) Europium (III) (Eu (TTA) ₃ (phen)), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphine Various compounds such as platinum (II) Metal complexes; benzene compounds such as distyryl benzene (DSB), diamino distyryl benzene (DADSB), naphthalene Naphthalene compounds such as nile red, phenanthrene compounds such as phenanthrene, chrysene, chrysene compounds such as 6-nitrochrysene, perylene, N, N'-bis (2,5-di-t-butylphenyl) Perylene compounds such as -3,4,9,10-perylene-di-carboximide (BPPC), coronene compounds such as coronene, anthracene compounds such as anthracene and bisstyrylanthracene, pyrene such as pyrene Compounds, pyran compounds such as 4- (di-cyanomethylene) -2-methyl-6- (para-dimethylaminostyryl) -4H-pyran (DCM), acridine compounds such as acridine, stilbene Stilbene compounds, 4,4'-bis [9-dicarbazolyl] -2,2'-bif Carbazole compounds such as phenynyl (CBP), 4,4'-bis (9-ethyl-3-carbazovinylene) -1,1'-biphenyl (BCzVBi), thiophene compounds such as 2,5-dibenzoxazole thiophene, Benzoxazole compounds such as benzoxazole, benzoimidazole compounds such as benzimidazole, benzothiazole compounds such as 2,2 '-(para-phenylenedivinylene) -bisbenzothiazole, bistyryl (1,4- Butadiene compounds such as diphenyl-1,3-butadiene), tetraphenyl butadiene, naphthalimide compounds such as naphthalimide, coumarin compounds such as coumarin, perinone compounds such as perinone, oxadiazole Oxadiazole systemization , Aldazine compounds, cyclopentadiene compounds such as 1,2,3,4,5-pentaphenyl-1,3-cyclopentadiene (PPCP), quinacridones, quinacridone compounds such as quinacridone red, pyrrolopyridines, Pyridine compounds such as thiadiazolopyridine, spiro compounds such as 2,2 ', 7,7'-tetraphenyl-9,9'-spirobifluorene, such as phthalocyanine (H ₂ Pc) and copper phthalocyanine Metal or metal-free phthalocyanine compounds, and further, boron compound materials described in JP2009-155325A and Patent No. 5660371, and the like can be mentioned, and one or more of these can be used.

As a material of the above-mentioned hole transport layer, any compound which can usually be used as a material of a hole transport layer can be used, and various p-type polymer materials and various p-type low molecular materials can be used alone or It can be used in combination.
Examples of p-type polymer materials (organic polymers) include polyarylamines, fluorene-arylamine copolymers, fluorene-bithiophene copolymers, poly (N-vinylcarbazole), polyvinylpyrene, polyvinylanthracene, polythiophenes, and the like. Polyalkylthiophene, polyhexylthiophene, poly (p-phenylenevinylene), polyvinylenevinylene, pyreneformaldehyde resin, ethylcarbazoleformaldehyde resin or derivatives thereof, and the like can be mentioned.
These compounds can also be used as a mixture with other compounds. As an example, poly (3,4-ethylenedioxythiophene / styrene sulfonic acid) (PEDOT / PSS) etc. are mentioned as a mixture containing polythiophene.

Examples of the p-type low molecular weight material include 1,1-bis (4-di-para-triaminophenyl) cyclohexane and 1,1′-bis (4-di-para-tolylaminophenyl) -4-4. Aryl cycloalkane compounds such as phenyl-cyclohexane, 4,4 ′, 4 ′ ′-trimethyltriphenylamine, N, N, N ′, N′-tetraphenyl-1,1′-biphenyl-4,4 ′ -Diamine, N, N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine (TPD1), N, N'-diphenyl-N, N '-Bis (4-methoxyphenyl) -1,1'-biphenyl-4,4'-diamine (TPD2), N, N, N', N'-tetrakis (4-methoxyphenyl) -1,1'- Biphenyl-4,4'-diamine (TPD 3), N, N'-di 1-naphthyl) -N, N'-diphenyl-1,1'-biphenyl-4,4'-diamine (α-NPD), arylamine compounds such as TPTE, N, N, N ', N'- Tetraphenyl-para-phenylenediamine, N, N, N ', N'-tetra (para-tolyl) -para-phenylenediamine, N, N, N', N'-tetra (meta-tolyl) -meta-phenylene Phenylenediamine compounds such as diamine (PDA), carbazole compounds such as carbazole, N-isopropylcarbazole, N-phenylcarbazole compounds, stilbene compounds such as stilbene and 4-di-para-tolylaminostilbene compounds, OxZ Oxazole compounds, triphenylmethane, triphenylmethane compounds such as m-MTDATA, 1-phenyl-3 Pyrazoline compounds such as (para-dimethylaminophenyl) pyrazoline, benzine (cyclohexadiene) compounds, triazole compounds such as triazole, imidazole compounds such as imidazole, 1,3,4-oxadiazole, Oxadiazole compounds such as 2,5-di (4-dimethylaminophenyl) -1,3,4-oxadiazole, anthracene compounds such as anthracene, 9- (4-diethylaminostyryl) anthracene, fluorenone Fluorinone compounds such as 2,4,7-trinitro-9-fluorenone, 2,7-bis (2-hydroxy-3- (2-chlorophenylcarbamoyl) -1-naphthylazo) fluorenone, anilines such as polyaniline Compounds, silane compounds, 1,4 Pyrrole compounds such as dithioketo-3,6-diphenyl-pyrrolo- (3,4-c) pyrrolopyrrole, fluorene compounds such as fluorene, porphyrins, porphyrin compounds such as metal tetraphenyl porphyrin, quinacridone Metals such as quinacridone compounds, phthalocyanines, copper phthalocyanines, tetra (t-butyl) copper phthalocyanines, iron phthalocyanines or metal free metal phthalocyanine compounds; metals such as copper naphthalocyanines, vanadyl naphthalocyanines, monochlorogallium naphthalocyanines or Metal-free naphthalocyanine compounds, benzidine compounds such as N, N'-di (naphthalen-1-yl) -N, N'-diphenyl-benzidine, N, N, N ', N'-tetraphenylbenzidine Etc. , It can be used alone or in combination of two or more thereof.
Among these, arylamine compounds such as α-NPD and TPTE are preferable.

When the organic electroluminescent element of the present invention has a hole transport layer as an independent layer, the average thickness of the hole transport layer is not particularly limited, but is preferably 10 to 150 nm. More preferably, it is 40-100 nm.
The average thickness of the hole transport layer can be measured by a quartz oscillator film thickness meter in the case of a low molecular weight compound and by a contact step meter in the case of a high molecular weight compound.

As materials for the electron transport layer, pyridine derivatives such as tris-1,3,5- (3 ′-(pyridine-3 ′ ′-yl) phenyl) benzene (TmPyPhB), (2- (3- (9 (9) Quinoline derivatives such as -carbazolyl) phenyl) quinoline (mCQ)), pyrimidine derivatives such as 2-phenyl-4,6-bis (3,5-dipyridylphenyl) pyrimidine (BPyPPM), pyrazine derivatives, bathophenanthroline (BPhen) And phenanthroline derivatives such as 2,4-bis (4-biphenyl) -6- (4 '-(2-pyridinyl) -4-biphenyl)-[1,3,5] triazine (MPT) Derivatives, triazole derivatives such as 3-phenyl-4- (1′-naphthyl) -5-phenyl-1,2,4-triazole (TAZ) Oxazole derivatives, such as 2- (4-biphenylyl) -5- (4-tert-butylphenyl-1,3,4-oxadiazole) (PBD), 2,2 ′, 2 ′ Imidazole derivatives such as'-(1,3,5-bentlyyl) -tris (1-phenyl-1-H-benzimidazole) (TPBI), aromatic tetracarboxylic acid anhydrides such as naphthalene and perylene, bis [2 -(2-hydroxyphenyl) benzothiazolato] zinc (Zn (BTZ) ₂ ), various metal complexes represented by tris (8-hydroxyquinolinato) aluminum (Alq ₃ ), etc., 2,5-bis (6 ′-( Organic sila represented by silole derivatives such as 2 ′, 2 ′ ′-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole (PyPySPyPy) Derivatives and the like, can be used alone or in combination of two or more thereof.
Among these, metal complexes such as Alq ₃ and pyridine derivatives such as TmPyPhB are preferable.

When the organic electroluminescent element of the present invention has an electron transport layer, the average thickness of the electron transport layer is not particularly limited, but is preferably 10 to 150 nm. More preferably, it is 40-100 nm.
The average thickness of the electron transport layer can be measured by a quartz crystal thickness meter in the case of a low molecular weight compound, and by a contact step meter in the case of a polymer compound.

The method of forming the metal oxide layer, the cathode, the anode, the light emitting layer, the hole transporting layer, and the electron transporting layer in the organic electroluminescent device of the present invention is not particularly limited, and plasma CVD, thermal vapor deposition, thermal Chemical vapor deposition (CVD) such as CVD and laser CVD, dry plating such as vacuum deposition, sputtering, and ion plating, thermal spraying, and liquid phase film formation such as electrolytic plating, immersion plating, and wet plating such as electroless plating Plating method, sol-gel method, MOD method, spray thermal decomposition method, doctor blade method using fine particle dispersion, printing method such as spin coating method, ink jet method, screen printing method, etc. can be used, according to the material Any suitable method can be selected and used.
It is preferable to select these methods according to the characteristics of the material of each layer, and the preparation method may be different for each layer. Among these, the second metal oxide layer is more preferably formed using a vapor phase film forming method. According to the vapor phase film forming method, the organic compound layer can be formed cleanly and in good contact with the anode without breaking the surface, and as a result, the effect by having the second metal oxide layer as described above Become more prominent.

In the organic electroluminescent device of the present invention, the above-mentioned buffer layer is preferably a layer formed by applying a solution containing an organic compound. By forming the buffer layer having a predetermined thickness by coating, it is possible to effectively suppress the crystallization of the material for forming the layer to be formed on the buffer layer.
The method of applying the solution containing the above organic compound is not particularly limited, and spin coating method, casting method, microgravure coating method, gravure coating method, wire bar coating method, bar coating method, bar coating method, slit coating method, roll coating method, dip Various coating methods such as a coating method, a spray coating method, a screen printing method, a flexo printing method, an offset printing method, and an ink jet printing method can be used. Among these, spin coating and slit coating are preferred in that the film thickness can be more easily controlled.
By forming the buffer layer by coating, unevenness on the surface of the oxide layer is smoothed, so crystallization of a material for forming a layer to be formed next on the buffer layer is suppressed.

Examples of the solvent used to prepare the solution containing the organic compound include inorganic solvents such as nitric acid, sulfuric acid, ammonia, hydrogen peroxide, water, carbon disulfide, carbon tetrachloride, ethylene carbonate, etc., methyl ethyl ketone (MEK) ), Ketone solvents such as acetone, diethyl ketone, methyl isobutyl ketone (MIBK), methyl isopropyl ketone (MIPK), cyclohexanone etc., alcohol solvents such as methanol, ethanol, isopropanol, ethylene glycol, diethylene glycol (DEG), glycerin etc, diethyl Ether, diisopropyl ether, 1,2-dimethoxyethane (DME), 1,4-dioxane, tetrahydrofuran (THF), tetrahydropyran (THP), anisole, diethylene glycol dimethyl ether Ether solvents such as diglyme) and diethylene glycol ethyl ether (carbitol), cellosolve solvents such as methyl cellosolve, ethyl cellosolve and phenyl cellosolve, aliphatic hydrocarbon solvents such as hexane, pentane, heptane and cyclohexane, toluene, xylene, Aromatic hydrocarbon solvents such as benzene, aromatic heterocyclic compound solvents such as pyridine, pyrazine, furan, pyrrole, thiophene and methyl pyrrolidone, N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA) Amide solvents such as chlorobenzene, dichloromethane, chloroform, dichloromethane, 1,2-dichloroethane, etc., ester solvents such as ethyl acetate, methyl acetate, ethyl formate, dimethyl sulfoxide (DM O), Sulfur compound solvents such as sulfolane, nitrile solvents such as acetonitrile, propionitrile, acrylonitrile, various organic solvents such as organic acid solvents such as formic acid, acetic acid, trichloroacetic acid, trifluoroacetic acid or the like, or And the like.

The solution containing the organic compound preferably has a concentration of the organic compound in the solvent of 0.05 to 10% by mass. With such a concentration, it is possible to suppress the occurrence of coating unevenness and unevenness when applied. The concentration of the organic compound in the solvent is more preferably 0.1 to 5% by mass, still more preferably 0.1 to 3% by mass.

The luminescent color of the organic electroluminescent device of the present invention can be changed by appropriately selecting the material of the organic compound layer, and a desired luminescent color can be obtained by using a color filter or the like in combination. For this reason, it can be suitably used as a material of a display device or a lighting device.
Such a display device formed using the organic electroluminescent device of the present invention is also one of the present invention, and a lighting device formed using the organic electroluminescent device of the present invention is also the present invention. It is one of the

EXAMPLES The present invention will be described in more detail by way of the following examples, but the present invention is not limited to these examples. In addition, unless there is particular notice, "part" shall mean "weight part" and "%" shall mean "mass%."

Example 1
(Step 1) Synthesis of 7,9-bis (3-bromophenyl) -8H-cyclopenta [a] acenaphthylene-8-one In a 300 mL three-necked flask, 1,3-bis (3-bromophenyl) propan-2-one ( 7.2 g (19.6 mmol), acenaphthenequinone (3.56 g, 19.6 mmol) and ethanol (196 mL) were added, and while heating and stirring, a solution of potassium hydroxide in ethanol (1.1 g dissolved in 20 mL) ) Is dropped. After completion of the dropwise addition, the mixture was heated and stirred for 2 hours while refluxing. The mixture was cooled to 0 ° C., and the precipitated solid was collected by filtration to give 7.75 (17.0 mmol) of 7,9-bis (3-bromophenyl) -8H-cyclopenta [a] acenaphthylen-8-one (yield) 87%).
Since this compound was insoluble in the solvent, identification was not performed, and the process proceeded to the next step.
The reaction of step 1 is expressed as the following reaction formula (4).

(Step 2) Synthesis of 7,10-bis (3-bromophenyl) -8,9-diphenylfluoranthene 7,9-bis (3-bromophenyl) -8H-cyclopenta [a] acenaphthylene-8-one 2.2 g (4.3 mmol) and diphenylacetylene (1.68 g, 5.1 mmol) were suspended in diphenyl ether (21 mL) and reacted for 8 hours while irradiating the micro. After cooling to room temperature, hexane was added and the precipitated solid was collected by filtration to obtain 2.2 g (3.31 mmol) of 7,10-bis (3-bromophenyl) -8,9-diphenylfluoranthene (collection) 77%).
The NMR chart of the obtained compound is shown in FIG.
The reaction of step 2 is expressed as the following reaction formula (5).

(Step 3) Synthesis of 7,10-bis [3- (3-pyridyl) phenyl] -8,9-diphenylfluoranthene (fluoranthene A) 7,10-bis (3-bromophenyl) in a 100 mL two-necked flask Add 8,9-diphenylfluoranthene (1.20 g, 1.80 mmol), 3-pyridineboronic acid (738 mg, 6.9 mmol), Pd (PPh3) 4 (116 mg, 0.10 mmol), and add toluene (30 mL) ) And ethanol (7.2 mL). To this was added 2.0 M aqueous sodium carbonate solution (7.2 mL, 14.4 mmol), and the mixture was heated and stirred overnight under reflux. After cooling to room temperature, water was added and extraction was performed with ethyl acetate, and then the organic layer was washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by column chromatography to obtain 773 mg (1.17 mmol) of fluoranthene A. (65% yield)
The NMR chart of the obtained compound is shown in FIG.
The reaction of step 3 is expressed as the following reaction formula (6).

Example 2: Synthesis of 7,10-bis (3-bromophenyl) -8,9-diphenylfluoranthene (fluoranthene B) in a 100 mL two-necked flask 7,10-bis (3-bromophenyl) -8,9 Add diphenylfluoranthene (1.0 g, 1.51 mmol), phenylboronic acid (551 mg, 5.52 mmol), Pd (PPh3) 4 (87 mg, 0.075 mmol), toluene (15 mL) and ethanol (5. 5). It was dissolved in 4 mL). To this was added 2.0 M aqueous sodium carbonate solution (5.4 mL, 10.8 mmol), and the mixture was heated and stirred overnight under reflux. After cooling to room temperature, water is added and the mixture is extracted with chloroform, and then the organic layer is washed with saturated brine and dried over magnesium sulfate. After filtration, the filtrate was concentrated and the residue was purified by column chromatography to obtain 696 mg (1.06 mmol) of fluoranthene B. (70% yield)
The NMR chart of the obtained compound is shown in FIG.
The reaction of Example 2 is expressed as the following reaction formula (7).

Example 3 Physical Property Evaluation of Fluoranthene Compounds The HOMO and LUMO values of fluoranthene A and fluoranthene B synthesized in Examples 1 and 2 were calculated from cyclic voltammetry measurement and optical band gap measurement. The cyclic voltammetry was measured by BAS's electrochemical analyzer, and the optical band gap was measured by Shimadzu Corporation UV-1800. The measured values are shown in Table 1. It was revealed that fluoranthenes A and B had a deep and wide band gap with LUMO.

Example 4 Production and Evaluation of Organic Electroluminescent Device The organic electroluminescent device 1 shown in FIG. 4 was produced by the method described below.
[Step 1]
A commercially available transparent glass substrate with an average thickness of 0.7 mm on which a 150 nm thick patterned electrode (cathode 3) made of ITO is formed was prepared as the substrate 2. Then, the substrate 2 having the cathode 3 was subjected to ultrasonic cleaning in acetone and isopropanol, and then UV ozone cleaning was performed for 20 minutes.
[Step 2]
On this ITO electrode (cathode 3), a zinc oxide (ZnO) layer with an average thickness of 10 nm was formed by sputtering using zinc metal as a target and using oxygen as a carrier gas and argon as a carrier gas. After that, washing was performed with isopropanol and acetone. Furthermore, this substrate is set in a spin coater, and a 1 wt% magnesium acetate solution (water / ethanol = 1/3) is spin coated at 1600 rpm for 60 seconds, and annealed at 400 ° C. for 1 hour by a hot plate under air. went. Subsequently, the substrate was washed with water and then dried on a hot plate at 250 ° C. for 30 minutes under the atmosphere to form an oxide layer 4.
[Step 3]
Next, the electron injection layer 5 containing an organic compound was formed on the oxide layer by the method described below. First, fluoranthene A synthesized in Example 1 was dissolved in cyclopentanone to prepare a 1 wt% cyclopentanone solution. Next, the substrate 2 on which the cathode 3 and the oxide layer 4 formed in [Step 2] were formed was placed in a spin coater. Then, while a 1 wt% cyclopentanone solution of fluoranthene A was dropped onto the oxide layer 4, the substrate 2 was rotated at 3000 rotations per minute for 90 seconds to form the electron injection layer 5. The cyclopentanone solution concentration and spin coating conditions were set so that the film thickness of the electron injection layer 5 was about 10 nm.
[Step 4]
Next, the substrate 2 on which each layer up to the electron injection layer 5 was formed was fixed to the substrate holder of the vacuum evaporation system. Moreover, bis [2- (2-benzothiazolyl) phenolato] zinc (II) (Zn (BTZ) ₂ ) represented by the following formula (8) and tris [1-phenylisoquinoline] iridium represented by the following formula (9) (III) (Ir (piq) ₃ ) and N, N′-di (1-naphthyl) -N, N′-diphenyl-1,1′-biphenyl-4,4 ′ represented by the following formula (10) -Diamine (α-NPD) and N4, N4'-bis (dibenzo [b, d] thiophen-4-yl) -N4, N4'-diphenylbiphenyl-4,4'- represented by the following formula (11) The diamine (DBTPB) and Al were respectively put in an alumina crucible and set as a deposition source. Then, the pressure in the vacuum deposition apparatus is reduced to a pressure of about 1 × 10 ⁻⁵ Pa, and Zn (BTZ) ₂ is co-deposited with the host and Ir (piq) ₃ as a dopant to form a light emitting layer 6 did. At this time, the doping concentration was such that Ir (piq) ₃ was 6% by weight with respect to the entire light emitting layer 6. Next, on the substrate 2 on which the light emitting layer 6 was formed, DBTPB and α-NPD were deposited by 10 nm and 30 nm, respectively, to form a hole transport layer 7. Further, molybdenum trioxide MoO ₃ was deposited by vacuum vapor deposition to form a hole injection layer 8 having a thickness of 10 nm.
[Step 5]
Next, aluminum (anode 9) was vapor-deposited to a film thickness of 100 nm on the substrate 2 on which the hole injection layer 8 was formed, to obtain “element 1” which is an example of the present invention.

Example 5
In the above [Step 3], instead of using the 1 wt% cyclopentanone solution of fluoranthene A synthesized in Example 1, a 1 wt% cyclopentanone solution of fluoranthene B synthesized in Example 2 was used. In the same manner as in Example 4 except for the above, "Element 2" which is an example of the present invention was obtained.

Comparative Example 1
A “device 3” was obtained using, in place of fluoranthene A in step 3 of Example 4, a bathocuproin (BCP) represented by the following formula (12), which is a commercially available electron injection layer material. Here, in order to make the film thickness of the BCP layer about 10 nm, the cyclopentanone solution was 0.1% by weight, and the spin coating was performed at 1000 rotations per minute for 120 seconds.

Measurement of Luminescent Properties and Lifetime of Organic Electroluminescent Device Voltage application to the device and current measurement were performed using a “2400 source meter” manufactured by Keithley. The light emission luminance was measured by "BM-7" manufactured by Topcon Corporation. Moreover, the uniformity of the light emission surface was confirmed visually. Further, the lifetime was measured using a photodiode and the change in luminance due to driving under a constant current with an initial luminance of 1000 cd / m 2, in which the luminance transition to 80% of the initial luminance was measured.
Leakage current values, luminous efficiencies and device life results of the devices 1, 2 and 3 manufactured in Examples 4 and 5 and Comparative Example 1 are shown in Table 2. Each result is shown as a relative value when the BCP value is 1. In addition, the leak current value was a current value when 2 V was applied to the device as a current flowing when light was not emitted.

The devices using fluoranthene A and B were confirmed to be devices having excellent leak suppression ability, luminous efficiency and long device life.

1: Organic electroluminescent device (reverse structure organic electroluminescent device)
2: Substrate 3: Cathode 4: Inorganic oxide layer 5: Electron injection layer 6: Light emitting layer 7: Hole transport layer 8: Hole injection layer 9: Anode

Claims (8)

A material used for an organic electroluminescent device having a structure in which a plurality of layers are stacked between an anode and a cathode formed on a substrate,
The material has the following formula (1):

(Wherein, R ^{1 to} R ¹⁰ are the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon ring group, or an aromatic heterocyclic group The material for organic electroluminescent elements characterized by including the compound which has the frame derived from fluoranthene represented by these.). In the above formula (1), at least one of R ^{7 to} R ¹⁰ is an aromatic hydrocarbon ring group which may have a substituent, or an aromatic heterocyclic group. The material for organic electroluminescent elements as described in 1. In the above formula (1), at least one of R ^{7 to} R ¹⁰ is an aromatic hydrocarbon ring group as a substituent or an aromatic hydrocarbon ring having an aromatic heterocyclic group. Item 2. A material for an organic electroluminescent device according to item 2. A structure in which a plurality of layers are laminated between an anode and a cathode formed on a substrate, characterized by using the material for an organic electroluminescent element according to any one of claims 1 to 3. An organic electroluminescent device having 5. The organic electroluminescent device according to claim 4, wherein the organic electroluminescent device has a metal oxide layer between an anode and a cathode. The organic electroluminescent device according to claim 4 or 5, wherein the organic electroluminescent device has a buffer layer which is a layer of a coating film of the material for an organic electroluminescent device. The display apparatus containing the organic electroluminescent element in any one of Claims 4-6. The illuminating device containing the organic electroluminescent element in any one of Claims 4-6.

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